Winthrop

By

Pamela

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Note: Some plot elements have been borrowed from the film, “The Graduate.”

Winthrop was home for the summer after his freshman year at Princeton. He was approaching his nineteenth birthday and was still a virgin. Definitely not for the lack of trying! He was pretty sure that his problem was shyness more than anything else. He had dated a few women during the year and he even thought that they liked his wit and quiet charm, but they uniformly lost interest in him after a few dates. As far as he could tell they dumped him because he didn’t know when the right moment was to seek a kiss. Their frustration with his prudery led them to move on to boys who weren’t so slow off the mark.

“So tell us Winthrop, are you dating?” his dad asked.

“Do you have a girlfriend?” his mom asked.

“Not quite. I’ve dated a bit. Just haven’t met the right girl yet.”

“You know that the Hutchinson’s daughter will be back from college next week.”

“That’s great.” Once again with the Hutchinson’s daughter, Kathleen. She was talented and pretty and Winthrop was sure that she would never go out with a guy like him. Yes, Winthrop was smart and not bad looking, but he had a very low social IQ. Coolness eluded him like water in a desert. He had never had a cool guy friend who could show him the ropes. He didn’t know what cool books to read or what cool music to listen to. He didn’t know how to dress cool or act cool. Kathleen dripped coolness and Winthrop did not see the point of opening himself up for rejection that would surely come. On top of that the Hutchinson’s were best friends with his parents and it would be too embarrassing for him to be rejected by the daughter of a couple that so often came over to the house. Better to leave that alone.

“You should go out with her when she’s back.”

“I’ll keep it in mind.”

“The Hutchinson’s are coming over tonight. You should ask Etta to let Kathleen know that you want to ask her out.”

Etta was Lou Hutchinson’s wife. Etta was voluptuous. Despite being in her forties she had an absolutely beautiful womanly figure and a gorgeous face. Ever since Winthrop was thirteen he’d been swooning over her. She was the heroine of his daydreams. She’d beckon him to come over to her and then she’d hug him and have him sit on her lap. He was sure that once he saw her tonight he’d be reminded of how delightful her ample bosom was, he’d be thinking about it all summer long.

Etta’s husband Lou was an absolute beast. One of those guys with broad shoulders, a perfect muscular manly chest, and a six pack. When he flexed his arms his biceps popped out like large rocks. Winthrop on numerous occasions had seen him and his muscles in his bathing suit poolside at the house when his mom and dad were barbequing.

Of course, Winthrop was more interested in gazing at Etta in her bikini or one-piece bathing suits with her lovely over-sized breasts and perfectly shaped rear end. A favorite view of Winthrop’s was the flat place in Etta’s front where her legs met. Behind the smooth fabric of her bathing suit must be the entrance to that most magical of caverns. One that he had never visited in the real world but had seen in his mind’s eye during feverish sessions locked in the bathroom.

“Okay, okay,” Winthrop said while his mind was refamiliarizing itself with the memories of Etta’s body that he had carried around in his head prior to leaving for Princeton the past fall.

***

That evening Etta and Lou came over wearing their swimming attire. Winthrop’s dad was grilling chicken on the barbecue. His parents had insisted Winthrop join them for the barbeque and swimming. Winthrop resisted the swimming part because he worried that the sight of Etta in her bathing suit might cause him to get a boner. That was so uncool. Wearing his shorts and tight boxers he could pretty well hide one if it formed. In his swimming trunks his boner would stick out like a telephone pole.

As Winthrop predicted, Etta was even more gorgeous than he had remembered her. Lou hadn’t changed much at all though he was wearing a little speedo for the first time. The outline of his penis was visible. This was too much information as far as Winthrop was concerned. He wondered if Lou was trying to seduce his own mom. Could she actually be comfortable looking at this hunky, muscular guy with little of his private part left to the imagination?

Winthrop looked to see if he could get a sense that his dad was scandalized by Lou’s appearance but he didn’t pick up that vibe. Winthrop decided that the two couples were such good friends there was no need for modesty or room for jealousy.

Lou went over to the grill to chat and Winthrop’s mom went into the house to get drinks. Etta sat down on a chaise lounge and invited Winthrop to take the chair next to her. His eyes were soaking up every part of Etta so that it would be available later in his imagination when he was alone in his room. Etta asked him about Princeton, about his studies, about his social life. She seemed quite interested in him. “You’re becoming a man, aren’t you Winthrop?” she said.

“I guess so. It can’t be stopped can it?”

“I suppose not,” Etta said smiling at him.

It occurred to Winthrop that Etta could probably see the hunger in his eyes. This was dangerous territory. One word from Etta and Winthrop was sure that Lou could break him in two like a bread stick. He’d have to be disciplined around Etta. Keep the sexual fantasies entirely internalized.

Remembering what his mom wanted him to talk about, Winthrop asked Etta about Kathleen. Etta gave him just the bare essentials about how her year at college had gone. He had no sense that she wanted to fix him up with her daughter. After a pause in the conversation, Etta smiled and said, “Do you have a girlfriend at Princeton?”

“I dated some.”

“But no girlfriend?”

“I’m afraid not.”

“I remember you saying that you hoped to get a girlfriend in college because you never had one in high school.”

“Yeah, I was optimistic, but I haven’t had any luck. Now I’m beginning to worry …”

“Worry?”

“I’m sorry. I shouldn’t have said that.”

“It’s okay Winthrop. I’m happy to be a receptive ear if you need someone to talk to about your troubles. I’ve always been fond of you.”

“Thank you Mrs. Hutchinson I really appreciate that. To tell you the truth I’m starting to think that I’ll never get a girlfriend. All the guys I meet at school talk about their – what should I say ‘conquests’ – while I’ve barely ever even kissed a girl.”

“You poor dear.” Etta smiled and said, “I’m sure your luck will change. You’re a very attractive young man! I imagine that many girls would love to be your girlfriend.”

Winthrop’s mother came outside and handed out drinks and then joined Etta and Winthrop. The two women began talking about a dress sale at a local department store and Winthrop took the opportunity to scrutinize Etta’s body. She still had the most wonderful shape. God would he love to touch her breasts! And her wonderful bikini bottom. It was a treat to look at. Winthrop must have let his guard down because when he looked up he saw that Etta was watching him stare at her body. Oh boy, he thought to himself. I hope she doesn’t complain to my mom about it.

A short while later Winthrop’s mom got up to help out at the grill. When she left, Etta said, “If you’re not too busy next week, I wonder if you could help me hang some new curtains I ordered? Lou is leaving town on business for a couple of weeks and the curtains will be delivered Monday. I would love for them to be up before Kathleen comes home.”

“Sure, I guess I could help. I don’t know much about curtains.”

“We just have to add the hardware and hang them. It’s easy. I’ll show you what to do.”

“Okay. Give me a call and I’ll come over.”

“Thank you so much, Winthrop.”

The more Winthrop thought about the invitation from Mrs. Hutchinson the more he thought that maybe she just wanted to create an opportunity where they could talk more openly about his problems. It would be nice to listen to the perspective of a smart woman on his love troubles. Who knows. Maybe she even could give him some pointers that helped him get a girlfriend.

***

Early Monday afternoon Winthrop answered the phone. Etta was ready for him to come over. He told his mom that he’d be helping Mrs. Hutchinson hang some curtains. It shouldn’t take too long. He walked the few blocks that separated their houses. Winthrop was surprised to see that Etta was dressed as if she had just come back from a wedding or some other fancy occasion. She was wearing a tight-fitting floral dress, stockings,, and heels. Before he could speculate as to what that meant, Etta said, “I’ve been at a charity board meeting and haven’t yet had a chance to change into something more comfortable. I thought you’d take more time getting here.”

“It’s okay Mrs. Hutchinson. I can wait while you change or come back later.”

“No, you’re here. It will be all right. Call me Etta, will you?”

“Okay, Etta.”

“Could you carry these curtains up to the bedroom?”

“Sure.”

Winthrop picked up a large package and followed Etta up the stairs to her master bedroom suite. He put the curtains down next to the window. “Tell me what you’re planning to do this summer,” Etta said.

“I guess I need to look for a …”

“Please be a dear and lower my zipper,” Etta said interrupting him. She turned so he was facing her back.

Shocked, Winthrop said, “On your dress?”

Etta laughed, “Of course, Winthrop. You were saying that you were looking for a job?”

Winthrop’s fingers trembled as they touched the zipper. To pull it down he realized that he had to use his other hand to hold the fabric against Etta’s back. When his hand touched her warm skin below her neck he felt rockets shooting off inside him. He tugged gently on the zipper until it began to move down her back. “How far would you like it?”

Etta laughed again. “All the way Winthrop, if you don’t mind.”

Winthrop continued lowering the zipper until he saw Etta’s exposed bra strap. The zipper ended just above the swell of her rear end where he saw the waistline of her panties. He stepped back nervously. He realized that a boner had formed in his shorts. Discretely he put his hands in his pockets and redirected his penis to an angle that wouldn’t be visible.

Etta turned around and faced him. “You’re looking for a job?”

“Oh, yes,” Winthrop said. “Maybe a grocery store. I don’t …” Winthrop lost his train of thought and abruptly stopped speaking. He had expected Etta to take off the dress out of his sight, but instead she let it fall off her shoulders in front of him exposing her bra with her massive breasts safely tucked within the cups. The bra was black, lacy, and feminine.

“A grocery store, what else?” Etta let the dress slip further down to the floor and then stepped out of it.

“Grocery …” Winthrop said. Holy smokes. He wondered if he should tell her to stop. His eyes didn’t know whether to stare at her bra or her garter belt holding up her stockings and the sexy black panty underneath.

Etta stood in front of him gazing quizzically at him. “Yes, you said grocery store. Any other kinds of jobs?”

“But Mrs. Hutchinson, I mean Etta! You’re …”

“You’re what? Winthrop?”

“You’re in your underwear!”

“Said Sherlock Holmes!”

“But you’re my mom and dad’s friend! What about Mr. Hutchinson?”

“Lou? What about him?”

“You know what I mean, don’t you? I can see your bra, your garter belt, and stockings! Lou’s your husband!”

“Winthrop, I know who he is. If you’re worried about him coming home, he’s on a business trip and won’t be back for almost two weeks. You have nothing to fear.”

“What about my mom and dad?”

“What about them?”

“I’m sure they don’t want me to see you in your underwear.”

Etta laughed, “They don’t?”

“If they found out they’d be …”

“They’d be what, Winthrop?”

“Scandalized!”

“Perhaps. Anyway, how will they know?”

“I still don’t understand why you’re letting me see you in your underwear.”

“When you said that you haven’t had a girlfriend yet, I felt sorry for you. As I said yesterday, I’ve always been fond of you and I think that there’s a lot I can do to help you boost your self-confidence with women. If you give me the opportunity I’ll try and help you.”

“That’s why you took your dress off?”

“Yes, Winthrop. By exposing you to the intimate side of women you’ll find that you’ll be less inhibited around them. In a word, you need experience. Familiarity with all things female. Once you obtain that experience you’ll be so much better able to feel comfortable with the coeds on campus.”

“You really think that’s true?”

“I do. Your almost complete lack of experience of girls’ bodies, their underwear, the way they think and behave has contributed toward your shyness around girls. I’ve taken my dress off so you can make a start toward becoming comfortable with women’s bodies and clothing.”

“So what you’re saying is that if you work on the curtains in your underwear, it’ll help me see women in a more relaxed way.”

Etta burst into laughter. “You’re an absolute delight, Winthrop.”

“I am?”

“Please let me worry about the curtains. Working on them in my underwear is not the issue. The focus right now is on getting you comfortable with the physical aspects of girls.”

“By being exposed to them?”

“Yes. You’ve been gawking at my bra, garter belt, and panties ever since I took off my dress. That shows how novel they are for you. You’re not yet sufficiently familiar with them so that you look at them without gawking.”

“I’m sorry, Mrs. Hutchinson. I tried to look away!”

“There was no need to. I should also add that despite five or six years of you staring at me in my swimsuits, you’re still unable to be relaxed next to me at the pool.”

“How did you know that?”

“Subtlety is not your strong suit. Gawking at my bathing suit or my bra and garter belt is a sign that you aren’t comfortable with what you’re seeing. With more experience I expect that you’ll no longer gawk. Instead you’ll have the self-confidence to take note of female beauty in stride. That’s what will help you acquire a girlfriend.”

“I sure hope that’s true!”

“One obvious first step we can take is to give you an opportunity to do an up close and personal exploration of my more intimate side.”

“What does that entail?”

“I’ll show you. Let’s start with bras,” Etta said. “How familiar are you with them?”

“I guess I’ve only seen them on TV or in magazines.”

“Now you’re seeing one up close doing its job.”

“Yes, I see,” Winthrop said, reveling in his view of Etta’s bra.

“Come take a good look.”

Etta stood facing Winthrop and signaled him to come close to her. He took a few steps until, trembling, he was next to her.

“See how the bra holds my breasts?”

“Yeah.” Winthrop was weak in the knees and thought he might faint.

“Don’t be shy, Winthrop.” Etta took his hand and placed it against her bra cup. “Run your fingers over the fabric holding up the bottom of my breasts.” Winthrop felt the weight of her breast. “Do you feel the heft? The bra cup is really being stressed by my boob, is it not?”

“Yeah,” Winthrop said.

“Take a close look, Winthrop. Do you know that hidden in the fabric at the bottom of the cups is the underwire?”

“Really? They put a wire in there?”

“Yes.”

“What’s it do?”

“It helps to hold up my breasts.”

Winthrop leaned in so his face was close to the bra. The reality of Etta’s breasts sitting inches from his face within the bra tormented him. Winthrop touched the bottom of the bra. “I can feel the underwire. Do all bras have underwire?”

“No Winthrop. Some are wireless bras.”

“They can hold breasts without a wire?”

“Yes.”

“Do you wear wireless bras too?”

“I might have one. My breasts are pretty big. It’s a lot of work for a wireless bra to hold them up.”

“I can imagine. I think you’re wearing a really nice bra Mrs. Hutchinson.”

“Thank you, Winthrop.”

“Oh, my God, Mrs. Hutchinson, Etta, I have to say this is so …”

“So what?”

“So unbelievable. So intense!” Winthrop’s loins were red hot with desire. He couldn’t recall ever before being so wildly stimulated as he was.

“That’s exactly why this is so necessary. One can draw a straight line between your heated reaction and your lack of familiarity with girls’ bodies and clothes. I really want to help you with this.”

“Okay, yeah, you’re right. This probably really is essential. I have to be desensitized by first getting to feel these strong emotions.”

“Very good, Winthrop. I can see why you got into Princeton. You’re very smart.” Etta raised her arm and said, “Now take a look at the bra strap as it runs around my side. I know men like looking at women’s breasts from this angle.”

“Oh yeah. You’re so beautiful Mrs. Hutchinson!” Etta was right. The angle did catch the remarkable projection of her breasts at the sexiest possible perspective. “I really love the way your bra cup seems to just pop up out of your chest. It’s a very nice thing. Do you like wearing a bra?”

“I don’t mind wearing bras, Winthrop.”

“Your bra is comfortable to wear?”

“Yeah. When you’re a girl you get used to wearing bras.”

“I’m glad girls like their bras.”

“It’s considerate of you to say that, and I like the fact that a young man such as yourself is interested in what girls think about bras. Moreover, if you derive pleasure from the fact that girls like them, all the better.”

“Thank you.”

“What do you think of the lace designs in my bra?”

Etta directed Winthrop’s attention back to the top, lacy part of the cups. “It’s pretty, so pretty.”

“So when you meet a coed at Princeton that you like, when you look at her blouse or tee-shirt you now have a good idea of what might be going on underneath.”

“Yeah. I see what you’re saying.”

“She’s a girl. She wears a bra. You now know what bras look like up close and personal. A little bit less mystery to cause you anxiety!”

“Thank you, Etta.” Winthrop was so aroused that he was having trouble listening to her. With some desperation he said, “Do you think you could show me what’s inside your bra?”

“My tits? You want to see my tits?”

“I’m sorry Mrs. Hutchinson. Very sorry…”

“In due course Winthrop. We’ll get to that. Be patient. Right now we’re doing the underwear. Now let’s get you acquainted with my garter belt, panties, and stockings.”

“Get acquainted?”

“Yes. Slip down to your knees so you can get a good look.”

Winthrop did as she said so her garter belt was at his eye level.

“Do you know why I’m wearing a garter belt?”

Winthrop was transfixed by Etta’s thighs. What was there about them that was so pretty? To see the garters attached to Etta’s stockings splayed over her thighs was heavenly. “To hold up your stockings?”

“Very good, Winthrop. Aren’t you clever. Can you see that my panties are underneath the garter belt?”

“Yeah, sure.”

“Do you notice that my panties match my bra?”

Winthrop studied the front of Etta’s black panties that was visible beneath the garter belt. Most obvious was the way her pubic hair was evident behind the fabric. There was black lace in a pattern edging the leg holes and the waist band of the panty. He looked up at Etta’s bra and saw a similarity in the lace pattern. “Yeah, I see they match.” Looking upward to Etta’s bra was a mistake. The image of two large breasts from below in a bra caused an electrical storm of desire in Winthrop. He had to quickly look down.

“Help me take off my garter belt so you can get a better view of my panty.”

“Sure. What do I do?”

“First undo the garters from my stockings.”

“Undo them?”

“Slide the tab upwards in each garter and they’ll be released.”

Just inches from his face was the front of Etta’s panty. Winthrop stared at it in fascination.

“Winthrop? Have you dozed off?”

“Oh, sorry!” Winthrop used two hands to undo one of the garters. “What an incredibly ingenious invention!” he exclaimed.

Etta rolled her eyes. “Isn’t it? Very good, Winthrop. Continue with the other garters.” He undid the remaining garters.

“Three on each leg. I love that! The garter belt must be quite secure in holding up your stockings.”

“Definitely Winthrop. Now unhook the garter belt. The clasp is in the back.” Winthrop went behind Etta and unhooked the garter belt. As it came off her, he held it in his hand with the garters dangling down.

Winthrop stood up and handed it to Etta. “Here it is. Thank you for letting me help you off with it.”

“My pleasure, Winthrop.” Etta took the garter belt from Winthrop and put it on her dresser. “Now you’re welcome to admire my panty.”

Winthrop quickly got on his knees again to gaze at the front of Etta’s panty. “I really love your panty. The black lace is pretty. The panty is such a nice shape too.”

“You a very agreeable young man.”

“Thank you, Etta. I think this is such a great idea. Learning about woman so up close and personal! The front of your panty is flat. I guess girls don’t have a bulge there like boys do.”

“I’m glad you’ve got that figured out.”

Etta slowly rotated in front of Winthrop’s gaze. “Now you see my tushy in the panty. Feel how smooth the fabric is over my bottom.”

Winthrop gently touched the panty covering Etta’s derriere. “I love it! It’s so silky.” The shape was otherworldly smooth and rounded. “I have to say that I love the beautiful shape of your thighs and how they merge with your rear end. I mean it’s all just so perfect.”

“It’s nice to be appreciated like that, Winthrop.”

“I wonder what your tush looks like. It would be interesting to hold it in my hands.”

“All in due time, Winthrop,” Etta said.

“I’ll look forward to that.”

“I’ll take off my stockings now,” Etta said. She sat on the bed and gently eased them off her legs from the top down while Winthrop watched mesmerized.

“I love how you take off your stockings.”

“Do you?”

“Do you like wearing stockings? Do they feel nice on your legs?”

“I don’t mind stockings at all. Stockings can feel nice on one’s legs, especially sheer ones.”

“Sheer stockings?”

“Stockings with thin material. It’s thin enough to be able to see the skin color underneath.”

“Gosh, Etta, there are so many fascinating things about being a woman. Your bra, garter belt, panty, and stockings are complicated. It amazes me how a woman can know so much.”

“You’re adorable Winthrop. I guess if you spend enough years as a woman you pick up a lot of knowledge about women’s underwear.”

“Yeah, that makes sense. I’d like to know everything that you know about women’s underwear.”

“You would?” Etta handed her stockings to Winthrop. “You may put my stockings next to the garter belt.” Winthrop got up and placed them on the dresser and walked back to her.

Winthrop looked at Etta wearing just her bra and panties. “I think that bras and panties make a very interesting and enjoyable subject.”

Their eyes met and Etta said, “So now, just like with bras, when you meet a girl you can envision what her panties look like within her dress, skirt, or pants.”

“I see, yes, definitely. Does changing into something more comfortable mean wearing just a bra and panty?”

“No, that’s not what I meant. By getting into something more comfortable I mean wearing a pretty outfit that is not too tight. For example, my favorite pink babydoll.”

“Babydoll?”

“Yes, that’s a short frilly nightie with ruffles and lace. It’s meant to be very feminine. When a woman wears something like that she’s usually being flirtatious, though the softness of the material is an attraction all its own. You can fetch my pink babydoll from the closet. It’s hanging with some other nighties on the left-hand side. You can’t miss it. There’s a matching pink panty on the hangar with it. Bring that too.”

Winthrop entered Etta’s walk-in closet. “Wow, you have so many clothes.” He had never seen so much ladies clothing in one place.

“Do you see it Winthrop?” Etta called out to him.

“One second!” He saw a relatively short, bright pink babydoll and took it off the hangar together with a matching panty. He looked at them for a second fascinated by the frilly features and then carried them back to Etta.

“I see what you said about being pretty. There so much intricate lace on the babydoll and panty. The fabric is very soft.”

“I won’t need to wear a bra with the babydoll. Do you know how to take a bra off of a lady?”

“Take off your bra?”

“Yes.”

“No, I’ve never done that. Though I’d like to learn how so I could see your … breasts?”

“You amaze me sometimes with your wisdom. I’ll teach you. The first thing you do is unhook it.”

“Unhook it?”

“In the back, you’ll see the hooks. Undo them.”

Winthrop went behind Etta and unclipped her bra. “I’ve released the two ends.”

“To take the bra off me, slide the straps off my shoulders and then gently pull the bra off of my boobs.”

Winthrop released the shoulder straps and then gently pulled on the cups. He watched as Etta’s large breasts were released to rest perfectly on her chest. “Great, Winthrop. You really know your way around a bra, don’t you?”

“Thanks Etta. It really wasn’t that hard to take your bra off. But man, your breasts are so beautiful. I love the delicious shade of ivory and your large, pointed, red nipples.”

“Thank you, Winthrop.”

“No. They’re really neat. I’ve never seen real breasts before – just in magazines and movies – but I’m certain that you have an amazing pair of breasts.”

“That is so sweet, Winthrop.”

“I can’t thank you enough for allowing me to see them!”

“It’s the kind of exposure you need if you’re going to feel comfortable with girls.”

Looking at Etta’s breasts it was hard for Winthrop to imagine he’d ever be comfortable around girls. “I was wondering, are your breasts heavy to carry around? I mean do you feel their weight?”

“You mean without my bra?”

“Yes. Like the way they are now on your chest.”

“I suppose I can feel their weight. For example if I lean over like this.” Etta leaned forward so her breasts swung free of her chest.

“Wow, that’s amazing,” Winthrop said. “They’re the most amazing things. The nipple is for babies to get milk?”

“Yeah.”

“What does that feel like?”

“You mean when I nursed Kathleen?”

“Yeah.”

“Well, I had a pretty good time with Kathleen. She didn’t suck so hard at the start as to give me sore nipples. So I was lucky that I got into a nursing routine with her that felt pretty good. Sometimes the nipples get sore and then it hurts when the baby starts sucking on them. I don’t envy mothers who have to deal with that situation.”

“Is it only babies who get to suck on nipples?”

“No. Sometimes grownups, especially men like to suck on nipples.”

“Wow.”

“Winthrop, would you like to suck on my nipples?”

“You mean you’d let me suck on your nipples?”

“I would if you want to. That is certainly something that we can arrange. The nursing fantasy has some interesting dynamics. Some women love providing their tits to men, some men love having tits to suck on. But some women don’t want to offer their tits and some men don’t care about sucking. What do you think fits us?”

“I think that you’d like me to suck on your breasts, and I know for sure that I’d love to do that.”

“Then at the right moment we’ll try that.”

“You mean you will let me suck on your breasts?”

“Yes Winthrop. But for right now we’ve just finishing up our discussion of breasts. Like previously with bras and panties, you now have some familiarity with tits. The girls you see on campus will usually have tits and you can now have some kind of mental image of what’s underneath their top and bra. The point is, Winthrop, that girls are not magical creatures that exist in your fantasy world. They’re living breathing humans with some physical differences from men.”

“I see what you’re trying to teach me. If I see girls as human I won’t be so afraid of them.”

“Yes, that’s generally the idea. I think you should touch my breasts for a minute or two. That will help remove some of the mystery.”

“I can touch them?”

“Yes, go ahead, Winthrop.”

“Oh my God, Etta! Thank you so much!”

Winthrop raised his hands and cupped Etta’s breasts. He gently swept his palms and fingers over their surfaces. His fingers played with her erect nipples.

“I like that you’re gentle. It’s good not to be rough with a ladies tits. Later, if we can arrange for you to suck on my tits, you’ll have to learn how to be firm with a nipple but not too strong or too weak. My feedback should help you find a happy medium.”

Winthrop smiled appreciatively at Etta. It was great to know that eventually he’ll get to suck Etta’s tits, but frustrating not to be able to do it that very second.

After a few more minutes of playing with Etta’s breasts she said, “Help me with my babydoll.”

“Sure.” Winthrop picked up the babydoll and arranged it so Etta could put her arms into the armholes. She lowered it over her head.

“Very good, Winthrop.”

“Pink is such a nice color,” Winthrop said. “Girls like it, don’t they?”

“Winthrop, you ask a lot of questions. Are you always this inquisitive?”

“Oh no! Am I doing that? Am I being really annoying?” Winthrop said.

“It’s all right Winthrop. I’m not criticizing you. Don’t be so sensitive. I’m just curious about your questioning. Do you always ask many questions, or is it just the subject we’re talking about?”

“I guess I do ask questions about lots of things. Sometimes I drive my parents and teachers crazy. Especially my mom since I spend a lot of time with her when I’m home.”

“Sometimes you might want to just enjoy things without asking questions.”

“I know you’re right. But … the thing is, Etta, that what you’re showing me today is all new to me. Every bit of it. I think that’s why I have so many questions.”

“You’re right, I understand. Part of my concern is that you miss out on enjoying my body. I want you to get all the pleasure that can come from engaging with my female body. Some of those pleasures are simply to be felt and not necessarily analyzed.”

“I’ll try, Mrs. Hutchinson.”

“Good, Winthrop. So, you were asking me if girls prefer pink?”

“Yes. They do, don’t they?”

“That’s the stereotype. Boys prefer blue, girls prefer pink. I’ll bet, however, that you prefer pink. Am I right?”

“Yeah, that’s true. I’ve always like pink and pink things.”

“I’ll bet the reason you prefer pink is because it is the stereotypical girl color. You like identifying with girls.”

Winthrop thought about what Etta had said. “I never thought about it that way, Etta, but I guess I do feel a little special titillation at the thought that I share my love of pink with girls.”

“With some girls. Remember it’s a stereotype. Now, I love pink also, though I wouldn’t say it’s my favorite color.”

“The pink in your babydoll is so beautiful. I love how the babydoll rests gently on your breasts. I can even see them through the fabric.”

“It’s a soft, sheer fabric on this babydoll. I bought it a few years ago thinking that Lou would get excited by it, but I don’t think he even notices it when I wear it. You have so much more appreciation for the babydoll than Lou does.”

“Gosh, I don’t understand why anyone wouldn’t fall in love with the pretty lace and ruffles.”

“We think alike, Winthrop. Now I need to switch my panty to the matching panty. So help me take off my black panty.”

“You’ll let me do that! Thank you Etta. That means that I’ll get to see what’s inside your panty. I’ve always been interested in that.”

“Have you now?” Etta laughed.

Winthrop kneeled down again and studied the lower lacy edge of the babydoll that sat at Etta’s waist. It was indeed a pretty sight. He worked his fingers under the babydoll to reveal the waist band of Etta’s black panty. He hooked his fingers under either side of the panty. “I’m going to pull down your panty now.”

Etta laughed again. “Go ahead, Winthrop.”

He tugged on the panty and his hands slid over Etta’s butt. “I’m feeling your rear end! It’s so smooth and round. Oh my goodness, I can see your pubic hair now!”

“Thanks for the blow-by-blow reporting,” Etta said.

“It’s black! Your pubic hair is a lovely shade of black. Oh my goodness!” Winthrop continued to pull and the panties dropped down Etta’s legs to the floor. “And your panties are off!”

Etta stepped out of them. “A job well done, Winthrop.” He stared at Etta’s pubic bush and the slit in the middle with great concentration.

“Before you help me put on the pink panties, would you like some time to explore my bush and tush?”

“Oh my God, would I ever, Etta! Thank you so much.”

Winthrop was hypnotized by the bush of curly black hair in front of him. “It’s so amazing. A vagina. The first vagina I’ve ever seen and it’s so beautiful. Can I touch it?”

“Yes, Winthrop.”

Winthrop gently put his fingers on the pubic hair. “Your hair feels so nice and it’s warm. I can feel the heat that it gives off.” Winthrop placed a finger directly over the slit that was visible through the pubic hair and gently pushed it in. “Oh God, Mrs. Hutchinson, my finger is at the entrance to your hole. The two sides are pressed against each other. I’m going to try and move my finger in there.”

Etta laughed. “You sound like my OBGYN.”

“I’m sorry.”

“Just go ahead and play with it Winthrop. I don’t mind. It’s kind of fun and charming to listen to your chatter.”

“I’ve wanted for a long time to see a vagina. This is so nice. I think I’d like to kiss it! May I?”

“Of course.”

Winthrop moved his face toward the bush until his mouth was buried in Etta’s pubic hair and touching the lips of her vagina. “Mmmmmm,” he said. “It’s so warm.” Winthrop gently kissed Etta’s pussy and looked up dreamily at Etta looking down on him. “I really like vaginas! And it has such a nice scent. I don’t know what it is about the scent but it thrills me in some strange way.”

“Many men like women’s natural scents. It’s an aphrodisiac.”

Winthrop held tightly to Etta’s buttocks to gain leverage and pushed his mouth more forcefully against the warm bush. “I’m just crazy about this. Such pretty pubic hair!”

“It’s so sweet of you to find so much comfort in my pussy.”

“I do.” Winthrop turned his attention now to Etta’s butt. He held the two cheeks in his hand and then kissed them. He pushed his face against her flesh. “Your butt is so nice, Mrs. Etta.”

Etta laughed and said, “You poor dear. Let it all hang out, Winthrop. Enjoy my tush and pussy to your heart’s content.”

“I can’t thank you enough, Etta.” Winthrop busied himself fondling Etta’s rear end. He held the cheeks, he stroked them. He explored between Etta’s legs and put his head through them so that she had to step wider. His lips came upon her bush from this angle and he kissed her vagina again. After a few minutes he said, “I’ve longed for this for so long. I’m so … what can I say … I’m so unbelievably … aroused …there is magic in your pussy and tush!”

“You’re a dear, Winthrop. Help me on with my pink panties. Later I’ll give you more opportunities with my vagina and breasts. How’s that?”

“Fine, Mrs. Hutchinson. Whatever you think is best.”

Winthrop fetched the panty and Etta stepped into it and pulled it up to her waist. The panty was made with ruffles and lace that matched the babydoll. Winthrop took a good look at Etta and said, “You’re just so pretty in that. I can’t believe that I’m lucky enough to see you wearing this outfit.”

“Thank you, Winthrop. This is what I meant by changing into something more comfortable.”

“I think I understand now.”

Etta sat down again on the bed and said, “Sit with me, Winthrop.” He sat on the bed next to her and she put her arm across his back. “You’re trembling, Winthrop. It’s as if I’ve caught a little bird in my hand.”

Winthrop laughed. “I’m just so excited. This has been the greatest day of my life. I don’t know what to think about – there are so many wonderful things. Your bra, your panties, your breasts, your vagina, your rear end, your babydoll. Gosh. I have so many beautiful memories of them!”

“It’s that enthusiasm I want to talk to you about now. You see, Winthrop, just as you’ve gotten to know me better today, I’ve also gotten to know you better. And I’ve learned some things about you I didn’t know before. When I invited you here I was thinking that you were a shy boy who could use some guidance with girls so that you might have better luck finding a girlfriend. Now …” Etta paused.

“Now?” Winthrop prompted.

“I want to say this right, Winthrop. Now I see you differently. What I took to be your shyness around girls is really more about your inability to project a male persona when you’re with a girl. In other words, your passivity isn’t because you’re a shy boy. No, it’s because your natural inclination is to make a girl-to-girl connection: in your mind, you, and the girl you’re with are really two girls. In the same way that you love pink, you get titillated from feeling that you and girls share a feminine passivity.”

“You really think this is true?”

“Yes. We can perform a little experiment in order to demonstrate the truth to you.”

“What’s that?”

“Bear with me and I’ll show you.” Etta went into her closet and emerged with a delicate yellow babydoll and matching panty and handed it to Winthrop. “Look at this pretty babydoll set.”

“It’s as lacy and ruffly as the one you’re wearing, though the design is different. It also has some ribbons that yours doesn’t have.”

“Correct! Would you like to wear it?”

“What?” Winthrop exclaimed. “Me wear it?”

“So, I’ve proved my point.”

“You lost me.”

“If a normal boy is asked if he wants to wear a babydoll and panties, he’ll say without hesitation: ‘NO!’” Instead, you responded: ‘What? Me wear it?’” In other words, your reflexive response is to consider the possibility of wearing the babydoll. You left the door open to wearing it. Your mind made a fast calculation along the lines of ‘Sure I’d like to wear it. Is there some way I can wear it even though boys aren’t supposed to wear babydolls.’”

Winthrop stared at Etta and then looked down at the babydoll. What she said was true. He knew that there was a part of him that had jumped with excitement at the thought he’d be given a chance to wear it. “I don’t know how you know me so well, but that’s right. I didn’t want to say no. I was hoping that you were serious about letting me wear the babydoll.”

“But I am serious, Winthrop. I do not want you to feel that you shouldn’t wear it you want to. I’m giving you permission to wear my yellow babydoll and panty. If you do, I won’t think any less of you.”

“To be honest. I like the idea that wearing the babydoll means that I’m sharing a love of lace, ruffles, and soft fabric with girls. It gives me a connection that is kind of thrilling.”

“So, you’ll wear it?”

“Yes, Etta. I’d like to wear it.”

“You should also wear a bra with it.”

“A bra?”

“Yes. With falsies in the cups you’ll feel like you have breasts and most importantly it will give the babydoll the same kind of look that mine has with my real breasts.”

“Okay. I see your point.”

“Good. So the first thing is for you to take off your shirt and pants.”

“Undress in front of you?”

“I undressed in front of you, didn’t I?”

“Yeah, but if I do it, then Lou could blame me for becoming naked in front of you. That might justify his killing me!”

Etta laughed. “Besides your having a fertile imagination, I don’t see Lou here anywhere. Do you?”

“No, you’re right.”

“How about I tell you what to do, Winthrop? This way, if Lou ever finds out about you stripping in front of me, all you have to do is tell him that I forced you to do it.”

“I guess that’s a good idea.”

“Wonderful, Winthrop. So, let’s get you undressed. First, take off your shirt.”

Winthrop took off his shirt. “My shirt is off.”

“Now I order you to take off your pants.”

“Oh, Etta, there’s a problem if I take off my shorts.”

“A problem? I’ll see your underwear?”

“No, yes, no, it’s not the underwear, it’s what’s …”

“You’re not making sense, Winthrop.”

“Inside. It’s what’s inside!”

“What’s inside?”

“My you-know-what.”

Etta laughed. “Oh, your you-know-what. You have a you-know-what inside?”

“I don’t want to offend you.”

“Seriously, Winthrop. You amaze me. Tell me what that thing between your legs is called.”

Winthrop hesitated and finally said, “A penis?”

“Are you asking me or telling me?”

“I obviously know it’s my … penis.”

“I’ve seen quite a few you-know-what’s in my lifetime Winthrop. I don’t mind looking at them and I won’t be offended looking at yours.”

“You won’t?”

“Undo your belt and button, Winthrop.” Winthrop obeyed. “Now pull down your zipper and take off your shorts.” Winthrop took the shorts off. “Very good, Winthrop.”

Out of modesty, Winthrop bent over with his hands in front of himself. “Stand up straight and keep your hands to your sides,” Etta said. Winthrop did as he was told. “My goodness, Winthrop, you have an Olympic sized boner in there.”

“I do?”

She stared at the tent in his boxers and laughed. “You don’t know that? You’re obviously blessed.”

“I am?”

“Judging by the size, it must be a blessing.”

“Size is important?”

“It’s not essential, but it’s a welcome bonus.”

“Gosh, I …”

“Pull down your boxers, Winthrop, so I can see what we’re dealing with here.”

“Well, okay, but you’re sure that Lou won’t find out about this.”

“Enough about Lou, okay?”

“Sorry.” Winthrop hesitated in order to gain some extra time to brace himself for the shock of exposing himself.

“Do you need help removing your underwear?” Etta said.

“No.”

“Then get on with it Winthrop. Show me what you’ve got!”

Winthrop lowered his boxers and his straight penis broke free, bounced up and down a bit and settled into a position pointing towards Etta at about fifteen degrees above horizontal. Etta walked up to him and said, “My, my, Winthrop, that is a treat.” She used a finger to pull his cock to the side and let it go. It bounced sideways a few gyrations and came to a halt. “Nothing like a stiff cock, Winthrop. It’s a nice size, it’s actually quite handsome. The stubby shape of your glans is the kind I’ve always liked. You should be quite proud of your penis.”

“I had no idea …”

“Because you’ve haven’t had an opportunity for girls to admire it,” Etta cut him off. “It looks like I’m the first girl lucky enough to see it – and soon to enjoy it!”

At Etta’s last remark Winthrop felt his penis pulse. She seemed to be implying that she was somehow going to use his penis in some way. Up to this point in his life, he had been the only one to use his cock and that was for the obvious reasons any boy uses it. “I can’t thank you enough for leading me out of my shell.”

“The pleasure is all mine. Let’s get you dressed and comfortable and then we can return to your marvelous cock,” Etta said. “First I’ll help you on with your bra. Hold your arms out.” Winthrop raised his arms and Etta put his hands through the bra straps and fastened it behind his back. She made some adjustments, and then put the falsies in the cups. “How’s that, Winthrop?”

“It feels a bit strange… but I don’t mind it. It is a pretty bra – thank you for picking out a pink one. I also feel kind of proud to have breasts now. Is that a weird feeling?”

Etta laughed. “What you’re feeling is no different than what many girls feel the first time they wear a bra. Moreover, just like with girls, in a short time you won’t even notice you’re wearing a bra.”

“Yeah, I see what you’re saying.” Winthrop looked at his bra from every angle. It took his mind off his rigid boner and he relaxed a bit.

“Now let’s get you into the babydoll!”

Etta lifted the yellow babydoll over Winthrop’s head and arms and pulled it down to his waist. “Now the pretty panty.” As Winthrop put the panty on he said, “What do I do about my …”

“Penis? What do you suggest?”

“I guess I could keep it in the panties but pointing up but there would still be a bulge. Or I could let it stick out through a leg hole.”

“Do whichever choice is best for you.”

“Okay.” Winthrop moved his penis so that it pointed outwards through a leg hole.

“So what do you think Winthrop? You’re all prettied up now. How does that feel?”

“I feel girlish dressed like this – but in a good way. A nice way. I mean I like feeling girlish. Is that weird?”

“Not if that’s who you are.”

Winthrop smiled at Etta. “I guess this is me. I’m feeling really happy. This is such a great idea. Wearing a babydoll with you is so much fun. You’re pink and I’m yellow. I confess that I kind of feel like I’m also a woman. Well, maybe a girl. You’re my mom and I’m your daughter. Something like that.”

“You’re a very sweet boy, Winthrop. Or should I say girl? Would you prefer that I call you a girl?”

“I never thought about it … sure, I guess so. It probably makes sense since I’m feeling like one.”

“You deserve to get a good look at yourself.” Etta led Winthrop to a mirror where he was enthralled with how sexy he looked in the yellow, frilly outfit. The interplay of his boobs with the fabric was similar to the way that Etta’s breasts and babydoll interacted with each other.

Winthrop’s eyes met Etta’s in the mirror and she said, “You have the body of a young maiden, Winthrop. The babydoll accentuates your femininity.”

“Thank you, Etta, it’s very nice of you to say that. I can’t believe how well you know me. I’m especially relieved to discover that my problem with girls is not due to my being shy.”

“I think we can take your rehabilitation further, Winthrop. You’re still a virgin and that has to be solved. Since you’re dressed as a young maiden, and, in fact, a virginal maiden, you’re ripe for having your cherry plucked.”

“Pluck my cherry?”

“Deflower you.”

“Deflower me? Oh, oh yeah.”

“It’s when a guy takes away the virginity of a girl.”

“Right. You put your … I mean, I put my penis inside your vagina. That’s how it works, right?”

“Are you teasing me, Winthrop? You’re really asking me this question?”

“I’m sorry, I sort of know that that is what boys and girls do, but I was afraid of being wrong about it.”

“It’s called fucking. You ever hear of that?”

“Yes, I have, but I never let myself focus too much on what it means – it seemed kind of scary and weird.”

“Weird it’s not. Scary it might be for someone who’s never done it. So I’ll fuck you and take care of your virginity problem.”

“Two girls can do that?”

Etta laughed. “Winthrop, in case you might have forgotten because of the pretty outfit you’re wearing, you do have the essential equipment needed for us to successfully fuck. I’m assuming here that your boner isn’t going away any time soon.”

“Right. I see what you mean. Even though I’m acting like a young maiden, I have the boy’s equipment. At the same time, you have the girls’ equipment but will be the boy who deflowers me.”

“Very good, Winthrop. There’s really no other way to do this is there? You obviously can’t take charge of our fuck. You wouldn’t know what to do.”

“Yes, Etta. I agree. I think I’d rather be a maiden even if I did know what to do. It seems to be a lot of fun to be prettily dressed. Also, I like the thought that you find me pretty so you want to make love to me.”

“I was going to suggest that you concentrate on imagining yourself to be a girl while we fuck, but it seems like you’re way ahead of me in that department. A moment ago you seemed confused as to which one of us has the penis. That’s good. It’s definitely appropriate for you to imagine you have a vagina and breasts.”

“I’ll try to do that. So how do we do this? How do boys and girls arrange themselves when they have sex?”

“Since you’re a virgin we’ll fuck the most common way for new brides. You lie on your back with your legs spread apart and I then put my pretend penis up inside of your pretend vagina.”

Winthrop lay on the bed and spread his legs apart with his boner pointing straight up. “So now you’ll aim your pretend penis so it goes into my pretend vagina, just like that?”

“Yes. That’s the idea. It’s helped a lot if you’re so excited that your pretend pussy is wet.”

“Wet? How does it get wet?”

“If a girl is excited about having sex then her vagina will naturally get wet. A natural lubrication to help a penis get inside her. Are you wet?”

“Yeah, I think so. Definitely.” Winthrop giggled. “Mrs. Hutchinson it’s so much fun learning about this.”

“I climb on top of you and aim my pretend penis for your pretend vagina.” Etta climbed on the bed, straddled Winthrop, and aimed her vagina toward the tip of his penis.

Noticing the proximity of Etta’s breasts, Winthrop said, “Do you mind if I touch your breasts again?”

“Knock yourself out, Winthrop.”

Winthrop reached inside the pink nightie and gently held Etta’s breasts.

“Put some of your spittle on your pretend pussy and on the end of my pretend dick,” Etta said.

“Spittle?”

“Saliva.”

“Right. You mean I should wet my pretend vagina with my saliva?”

“Yes, and my pretend dick.”

“Okay, but I’ll have to touch you there.”

“Ya think?”

Winthrop gingerly applied some of his saliva to Etta’s vagina and to the end of his penis. “Now what?” Winthrop asked.

“Just be still while I ram my pretend dick into your pretend pussy.”

“It can go in all the way?”

“Why not?”

“I thought that maybe my pretend hole isn’t deep enough.”

“It’s plenty deep. Okay, I’m going ahead.”

“It won’t hurt?”

“Hurt?”

“I heard it can hurt the first time.”

“If you were a girl losing her virginity it might hurt for a little bit.”

“Okay. I’m ready now.”

Etta slowly lowered herself onto Winthrop’s dick. When his penis touched her opening she gently wiggled her hips to help moisten the area. Then Etta settled herself onto Winthrop’s cock absorbing it to the hilt in her vagina.

Winthrop shrieked, “You’re inside me! Oh my goodness! It totally fit! I feel like I’m impaled! The pleasure is so intense. OH MY GOD, MRS. HUTCHINSON!”

Etta shook her head and said, “My ears, Winthrop.”

“I’m sorry! I just never felt such strong pleasure before! I can’t begin to describe it.”

“You don’t have to describe it.”

“I could stay like this forever. This is so neat. What’s next? Do we just stay like this? This is what is considered intercourse? I’ve lost my virginity now? Is that true?”

“You really don’t know what fucking is all about?”

“The man puts his penis in the woman. We’ve done that, haven’t we? Am I missing something?”

“Have you ever jerked off?”

“Yeah.”

“How do you do it?”

“I rub on it until it cums.”

“Right, so …”

“Oh my God, am I supposed to move my pretend vagina a bit? Is that what’s done?”

“Since I’m on top, which means that you can’t really move, I’ll ram my pretend penis into your pretend vagina over and over again until your orgasm takes place.”

“That makes a lot of sense. When do you start doing that?”

“Five minutes ago, Winthrop, if we hadn’t stopped for your analysis. With your permission I’m now going to continue our fuck.”

“Yes, definitely. Please do!”

Etta pulled her hips up slowly away from Winthrop’s penis causing him to cry out in pleasure once again. Before he knew what hit him, Etta began moving her hips in and out so her vagina alternately smothered and released Winthrop’s organ. Winthrop shook violently with each of Etta’s thrusts and cried out, “OH, MY GOD!” over and over again. A few seconds later Winthrop shrieked followed by a sound like a death rattle as his penis convulsed a half-dozen or more times releasing his jizz into Etta. She pulled herself off of his now collapsing dick and lay on her back next to him.

“Mrs. Hutchinson, that was the greatest thing that ever happened to me in my life!”

“I hope my hearing recovers,” Etta said. “You scream like a girl in a porno film, except twice as loud.”

“I do?” Winthrop gasped.

“I’m afraid so.”

“I’m sorry. The pleasure was slaying me. It’s so intense.”

“I’m not killing you am I? You don’t have a heart condition?” Etta asked.

“No. Not that I know of.”

“I’m glad to hear that Winthrop.”

“I can’t thank you enough Etta for that experience. Now I know why people like doing it. It’s so much more pleasurable than touching myself.”

“That’s the way nature wants and needs it – if we’re going to promulgate the species.”

“I love how you know so much, Etta. You’re a very smart person.”

Etta laughed. “Now that we’ve had our fuck, there’s one more important lesson for you, Winthrop.”

“What’s that?”

“When two people fuck, it’s virtually guaranteed that the boy will have his orgasm. You certainly did, right? But what about the girl? She is entitled to one also. Considerate boys make sure that their girlfriends get their orgasm.”

“Oh my God, Mrs. Hutchinson. Did you not get an orgasm? I’m so sorry. Gosh I feel terrible. Tell me what to do. I’ll do anything to get you one!”

“It’s all right, Winthrop, you don’t have to get so upset.”

“But Etta, I can’t stand the thought of you missing out on what you want.”

“I know that Winthrop. I mentioned this because this provides a nice opportunity for you to learn how to pleasure a woman without fucking her.”

“I can do that?”

“Sure. There are many ways boys and girls can have satisfying sexual relations without intercourse. In this particular case where we had sex but you orgasmed so fast that I never got a chance to have an orgasm there’s an ideal way that you can finish me off.”

“What is that?”

“You lick and suck on my vagina until I orgasm.”

“You mean with my mouth and tongue I lick and suck on your vagina. That’s great because I can get totally close to it. Wow. I’m sure I’m really going to like this.”

“Many boys enjoy doing this. It’ll be fun for both of us. I’ll guide you through it.”

“Thank you.”

Etta moved to the end of the bed and raised her legs up exposing her vagina. “Winthrop, I want you to kneel on the floor facing my vagina. This position gives you complete and easy access to my pussy. You can bury your face in it, revel in it, just have a lot of fun with it. I’ll steer you to the places I want you to lick and suck. Do you think you can do this for me?”

“I’ll try my best, Mrs. Hutchinson.”

“Great, Winthrop.”

Winthrop got into position and saw that he did have a nice angle and vantage point with which to lick on Etta’s pussy. “All right!”

“Go ahead.”

Winthrop leaned in and said, “There’s a white substance in your pubic hair. It seems to be leaking from your vagina.”

“I wonder what that could be?”

“I don’t know.”

“Winthrop. When you jerk yourself off …”

“Oh, how stupid of me. That’s my sperms!”

“Yes. Now go ahead and start licking me.”

“But what about the white …”

“Winthrop, just start licking. You can either ignore the jism or you can eat it. It doesn’t matter. Just start please.”

“Oh sure, no problem.”

Winthrop took a tentative lick across the opening of Etta’s vagina and noted the somewhat unusual taste of his semen. He liked how his tongue both felt Etta’s skin and pubic hair. “How’s that?” Winthrop said.

“That’s a nice lick, Winthrop.”

Winthrop licked her pussy again and said, “How’s that compare?”

“Winthrop. Just lick me without talking. Use your tongue to stimulate different parts of my vagina. If you’re doing a good job you’ll feel a place in the middle that gets hard very much like the way a boy’s penis gets hard. Find that hard spot and rub it with your tongue. The harder your tongue can rub it the better.”

“Okay, Etta,” Winthrop said, and now got down to making a point of using his tongue to explore all aspects of her pussy as he licked on it.

“That’s good, Winthrop, keep that up. I’m going to move your head from time to time to get you to the best places. Besides licking, you can also suck on my vagina – sort of gently nibble on it.”

Winthrop got absorbed in the job at hand. It was fun. It was definitely something that he enjoyed doing. Perhaps it was the giving aspect of it. Giving pleasure to Etta made him happy in a way he had never felt before. At the same time he felt himself zoning in on Etta’s pussy. His desire for it was rising with each lick. Her pussy was his friend and he’d do everything he could think of to give it pleasure.

As he attended to the vagina in front of him, he sensed that Etta’s pleasure was growing. She moaned softly in response to his tongue’s movements. Then he felt her thighs tensing up. Without warning her legs captured his head in a vice-like grip and Etta found a way to force his face tightly against her pussy. She rocked her hips up and back and her vagina pushed up against and along his mouth. Then she let out a small sound like “ahhhh” and the grip of her legs softened.

“Was that an orgasm?” Winthrop asked cheerfully with the pussy still an inch from his mouth.

“Yes, Winthrop. Now we go for another.”

“Another?”

“Winthrop, girls can get many orgasms in a row.”

“Really? I never knew that. But that makes me happy because I really want to continue doing this.”

“I knew you would Winthrop.”

Winthrop excitedly resumed his affectionate licking and sucking of Etta’s vagina. In a short while he once again sensed that she was about to have an orgasm when the phone rang. Winthrop stopped his licking and waited while Etta answered the phone.

“Hi Lou.” Etta said putting the phone on speaker.

Winthrop panicked and tried to move his head away from Etta’s vagina as if Lou could see him but Etta’s legs caught and held him. He saw Etta looking at him and simulating a lick with her tongue as if to tell him to continue what he had been doing. Evidently she was going to multi-task by having Winthrop lick on her vagina while talking to her husband.

“Hey babes,” Lou said. “How’s it going there. What are you doing?”

“I’ve got Winthrop helping me with the curtains. He’s doing a great job.”

“Good for him.”

“We’re on speaker phone and Winthrop is right here.”

“Hey Winthrop!”

Etta relaxed her legs and Winthrop nervously said, “Hey Mr. Hutchinson.”

“Etta isn’t working you too hard, is she?”

“No, not at all.”

“I’m glad you’re pleasing her.”

“I’m trying to.”

“No time for modesty, Winthrop. It’s great that you’re doing a job for Etta that I don’t like doing.”

“Winthrop is giving me great pleasure, Lou. There’s no doubt about that!”

Etta pointed to her vagina again and Winthrop resumed licking on her. Etta and Lou talked about an upcoming wedding they planned to attend. A short time later Winthrop felt the muscles in Etta’s thighs contract. He kept up his licking, all the while wondering how she could talk calmly with Lou while having an orgasm. Yet another orgasm came and went. This time Winthrop distinctly heard Etta moan.

“What’s that?” Lou asked.

“Winthrop hit himself with a curtain rod,” Etta said.

“Be careful, Winthrop!” Lou called out.

“I will,” Winthrop said.

A minute later the phone call wound down and Lou said goodbye.

Once again Etta loosened her grip on Winthrop and he said, “Goodbye, Mr. Hutchinson.”

After Etta hung up, Winthrop said, “Etta … “

“Hold that thought, Winthrop. I’ve got another orgasm in me. Her hips moved forcefully up and down a few times. She stopped to adjust her position and Winthrop managed to say, “But Etta, I think you can use my pretend vagina again!”

Etta sat up and looked at Winthrop’s penis and said, “You’re right! Do you think you can be on top this time?”

“I don’t know Etta. I don’t think I’m ready for that. I think its best if you are in control.”

“Fair enough. Lie down.”

Winthrop lay down as he had before and once again Etta mounted him. She was a bit more aggressive than before. It seemed to Winthrop that she knew that her next orgasm would be the best and to get to it she had to push her pretend penis into him as hard and fast as she could. He had started out worried that he’d orgasm too soon, but he managed to hold out until he was quite sure that Etta was in the throes of a large, final orgasm.

Etta didn’t immediately climb off of Winthrop. She lay on top of him, her large breasts in her pink babydoll pressed hard up against his own breasts in his bra underneath his yellow babydoll. Winthrop wrapped his arms around Etta and held her tightly. This was a terribly happy moment. To be pinned to the bed by the beautiful female presence of Etta. He was lucky that she had been so concerned about his troubles with girls that she had taken the matter into her own hands to straighten him out.

After a while Etta said, “I must be crushing you” and she slid off of him.

“No, not at all. I was so happy to lie under you.”

“Good.”

Winthrop wondered what would happen next. Would he see Etta again? The thought that he might not suddenly scared him and he said, “What’s going to happen now?”

“What do you mean?”

“I’m wondering …”

“Wondering what Winthrop?”

“I’m so scared that you won’t see me again,” Winthrop blurted out.

“That’s what you’re worried about?”

“Will I see you again?”

“You want to?”

“More than anything.”

“Well, we haven’t finished the curtains.”

“You mean you just want to see me to work on the curtains?”

“What did you have in mind?”

“You know. More of what we did today?”

“You mean you enjoyed our two fucks. I never would have guessed,” Etta said laughing.

“I loved them and I loved licking on you and I love wearing this pretty yellow outfit.”

“Well, I don’t know Winthrop. Part of me thinks that I’ve taught you all you really need to know about girls.”

“There’s nothing more?” Winthrop sounded desperate. “There must be something I need to know. You don’t want to teach me anymore?”

“Winthrop. This was fun. I had no idea that shyness wasn’t your problem with girls. Like you said before, your parents are unlikely to approve of what we did today. Your mom is my best friend. Of course, there’s also Lou who would be hurt if he found out about today.”

“I guess you’re right,” Winthrop said. His voice was low and sad. He wanted now to be alone and have a good cry.

Etta looked at Winthrop and said, “Look, Winthrop, I can’t make any promises, but come by tomorrow afternoon and we can at least talk about whether or not we should fuck again. We’ll both sleep on it and tomorrow we’ll probably have a clear idea of what we should do. How’s that?”

“Thank you, Mrs. Hutchinson. Thank you.”

“Good.” Etta got up and began taking off her babydoll and putting on her bra again. “You can put the babydoll set and bra on my dresser.”

For some reason Winthrop had been hoping that Etta would let him keep the babydoll. He really had to regain control of himself. He was going crazy.

After Winthrop was dressed and Etta had put on a top and jeans she had him hang the curtains in the bedroom. “Very good, Winthrop.” She took out her purse and handed five twenty-dollar bills to Winthrop.

“But Etta. I was happy to help you for free.”

“I know that Winthrop, but I feel that I perhaps took advantage of you.”

“Not at all. Please don’t give me any money.”

“You’re a wonderful child,” Etta said.

***

Walking home, Winthrop’s thoughts alternated between the profound joy he had felt that afternoon and unbearable worry that Etta might not agree to have sex with him again. He prayed that after sleeping on it, Etta would decide that she wanted to continue their sexual friendship.

By objecting to the money Winthrop hoped that Etta might see the extent of his love for her. Despite Lou, despite his parents and Kathleen and everything else, he was sure that he had fallen in love with Etta. He’d do anything to have more time with her.

When Winthrop got home his mom asked him, “How was the curtain hanging?”

“Not too hard. Mrs. Hutchinson liked my help. She asked me to help her again tomorrow.”

“You were away for quite some time; I’m surprised that there are more curtains to hang.”

“No. I just helped her a short time. Then I walked into town to see what kinds of jobs are available.”

“That’s marvelous. What did you find?”

“There might be a grocery job I could get. I have to go back tomorrow.”

“How nice. Keep your dad and me posted.”

Winthrop did not enjoy lying to his parents but considering the circumstances he had to do the best he could to keep them in the dark. The last thing he wanted to do was ruin the relationship between his mom and Etta.

Over dinner, Winthrop’s mom said that she had heard from Etta that Kathleen was coming home in a few days. She had proposed a date between him and Kathleen and Etta seemed agreeable to it. “It’s all set Winthrop. There’s no weaseling out of it. It’s about time that the two of you got to really know each other.”

“Okay, mom. Whatever you say.” Winthrop could not imagine how Etta allowed this to happen. It was one more thing that would make his life difficult.

The night passed slowly and interminably for Winthrop as he waited his fate. He felt like he was facing execution with a small hope for a last second reprieve.

***

The next day Winthrop walked to Etta’s and arrived at one o’clock. She answered the doorbell right away. Winthrop had decided ahead of time that what Etta was wearing would be a clue as to whether or not she was willing to have sex with him again. She was wearing a blue sundress with short sleeves, and white high heels. He could not figure out what that meant.

“Come in Winthrop. You look so dejected and scared.”

“I’m sorry Mrs. Hutchinson. I had nothing to do with the date with Kathleen. Please don’t blame me.”

Etta laughed. “I’m not blaming you, Winthrop. Your mom is very persistent about the two of you getting together and I decided that it probably wasn’t a bad idea.”

“I thought you didn’t want me to see her.”

“Yes, I’m not in favor of it – but not because you aren’t a wonderful boy, you are. As I’ve said before I’m quite fond of you but my fantasy husband for Kathleen is a more dynamic and mature man. After our time together yesterday, I think you’ll agree that even though you do have a penis, your proclivity is much more toward a young teenage girl than a man. Am I wrong about that?”

“I guess not.”

“Please don’t feel badly about it! You have nothing to be ashamed of. You’re entitled to be you. Obviously, I like you the way you are. My daughter, however, will not be attracted to a boy who sees himself as a young girl. I’m very certain of that. For that reason I haven’t stopped your mom from setting up a date between you. You’ll meet, you’ll talk and knowing Kathleen she’ll realize that you’re not the kind of boy she enjoys dating.”

“I see what you’re saying.” Etta’s comments made Winthrop see how complicated life was. His own desires for Etta and the part of him that she had seen yesterday that he had loved so much was actually the reason why Kathleen and he would be incompatible. That is, unless Kathleen was secretly like her mother! Anyway, he’d find out a lot on his date with her. “I guess what I’m most worried about is if I really do have a chance to see you again.”

“Let’s talk about that. Would you like something to drink?”

Winthrop looked at her fearfully wondering if offering him a drink was a way of letting him down more gracefully.

“I can offer you an Orangina.”

“Sure. That sounds good. Thank you.”

“Come sit in the living room.”

Winthrop took a seat on the sofa and waited until Etta returned with two Orangina’s.

She sat down far from Winthrop on a plush chair and Winthrop’s low spirits sagged even more. “I’ve been thinking Winthrop …” Winthrop spontaneously began to cry. “Oh, God, Winthrop, get a hold of yourself.”

“I’m sorry. Last night I realized that I love you, Mrs. Hutchinson,” Winthrop said.

“No, Winthrop, you don’t love me. You might have a crush on me, but it’s not love.”

“Well, I guess you’re right I don’t know. I’ve never loved a woman before. Anyway, what I’m trying to say is that I can’t stand the thought of not seeing you anymore. Yesterday was the best day of my life.”

Etta laughed. “You’re very young, Winthrop. Days will come in the future that you will also think are the greatest of your life. Anyway I want to tell you what I’m thinking.”

“I’m sorry for interrupting.”

“It’s okay, Winthrop. So what I’ve been thinking is that yesterday I was convinced that teaching you about girls and taking your virginity were acts of kindness on my part even if they were liable to not sit so well with Lou, your parents and Kathleen. The ends justified the means if you will. If we’re to continue to do what we did, I no longer have a simple moral justification. Thus, we need to think differently about our relationship.’

“What can that be?”

“It has to be based on a mutual agreement. A mutual guilt. To put it more simply, you have to be just as much a seducer of me as I am of you. I should be able to say: ‘Gosh, that Winthrop was so sexy and seductive, I couldn’t resist.’ So today I want you to seduce me.”

“But my not knowing how to seduce girls is my problem.”

“As a boy, yes, but as a girl you shouldn’t have that difficulty, should you?”

Winthrop realized that Etta was right. The previous day had taught him that if he made himself pretty it would overwhelm Etta’s defenses. If she had any vulnerability it was in resisting a boy masquerading as a young girl. “If you don’t mind could we go to your bedroom?” Winthrop asked.

“Finish your drink and we’ll go up,” Etta said. Winthrop took his last sip and followed her up the stairs and into her bedroom.

Once they were there Winthrop lifted his shirt up over his head and off. Then he took off his socks and then his pants and underpants so he was naked. His cock was rapidly rising with the excitement of what he was doing. He glanced over at Etta and saw she was smiling. “Can I look in your panty drawer?” Winthrop asked.

Etta nodded and Winthrop opened it up and looked at the large collection of Etta’s panties. He saw a pair of cute lacy pink panties and took it out. “I’d like to wear these, Etta,” Winthrop said.

“Sure, Winthrop,” Etta said.

Winthrop put on the panties. Then he opened Etta’s bra drawer and looked through her bras. He pulled out a pink one that matched the panties and asked, “May I please wear this bra?”

“Sure,” Etta said, “come here and I’ll help you put it on.”

While Etta helped him on with the bra he noticed her looking at his penis. He figured this was a hopeful sign, considering how much she liked it yesterday. Winthrop found the falsies and put them in the bra cups. He opened the drawer beneath the bra drawer and looked inside. There were various colorful apparel with straps, garters, lace designs. Winthrop’s eye landed on a bright pink garment and he took it out. It sorted of looked like a panty but it had garters dangling from it. “Etta, what is this pretty thing?”

“It’s a panty girdle. You wear it to improve your figure while it holds up your stockings.”

“May I wear it?”

“If you want to.”

“Thanks, Etta.” Winthrop stepped into the panty girdle and pulled it up to his waist. It required some tugging to get over his tush. “It fits snuggly,” Winthrop said. “How do I look?”

Etta laughed. “You look darling. Go to the bathroom mirror.”

Winthrop went to the bathroom and admired himself in the panty girdle and bra. They were his favorite shade of pink. He returned to Etta and asked her, “Do you have stockings I can wear with the panty girdle?”

“In the same drawer, on the right side. Take out two matching stockings.”

Winthrop found two nude-colored stockings and stared at them trying to figure out how to put them on.

“Come here,” Etta said. “I’ll show you how to put them on.”

Etta carefully rolled up each stocking and slipped them over Winthrop’s toes and up his legs. “I think I can attach the garters,” Winthrop said, “or at least try.”

“Be my guest.”

With some effort Winthrop figured out how to secure the garters to the stockings. When he was done he stood in front of Etta and said, “This is my underwear for this afternoon. I hope you find it pretty.”

Etta laughed. “Oh, I do, I do.”

“When I was in your closet yesterday I saw a pretty dress I want to wear if you don’t mind.”

“Show me which one,” Etta said.

They walked into the closet and Winthrop pointed to a pink dress with a wide skirt and fancy bodice made of a stretchy, lace material. “One of my oldest cocktail dresses. You can wear it but it requires a petticoat or two underneath to give it the proper pouf. That was the style back then.”

“Do you have the petticoats?”

Etta searched through the back of her closet and said, “Here are the two pink petticoats that I used to wear with that dress.”

“Can I wear them too?”

“Sure. First you put on the petticoats and then the dress goes on over your head.”

“I understand. Can you wait for me downstairs in the living room?”

“Wait for you …? Okay, sure, Winthrop.”

When Etta had gone, Winthrop put on the petticoats and the dress. He looked among Etta’s shoes and found a pair of open-toed heels and put them on. He walked back into the bedroom with wobbling ankles and looked at the perfume bottles on the top of the dresser. A bottle of Chanell No. 5 caught his eye and he put a few drops on either side of his neck. Then he went into the bathroom and looked through Etta’s cosmetics. He saw a tube of red lipstick and, looking in the mirror, put some on his lips. He had often seen his mom put on lipstick and he did his best to imitate what he remembered she had done. It was fun even if he could see that his hand had slipped in a couple of places.

Winthrop looked at himself in the mirror. While he could see a number of flaws in the image in front of him, he was nevertheless cute enough and feminine enough that he had a fighting chance of getting Etta interested in having sex with him. He planned in his mind’s eye how his seduction would unfold. He was definitely a novice but the previous day had made him see what he had to do to please Etta. Winthrop braced himself and descended the stairs to the living room to begin his quest for Etta’s affection.

Walking down the stairs in heels was no easy task. Winthrop had to steady himself on the handrail and a couple of times he thought he might plunge head-first down the stairs. Luckily, he made it to the bottom and then putting a smile on his face and attempting to walk like he’d seen models do on a runway he glided into the living room. Etta was sitting on the sofa reading a magazine that she put to the side when Winthrop appeared. He saw her stifling a laugh but to her credit she didn’t react in a way that would have made a mockery of his ardor.

Winthrop came up to Etta and stood in front of her. He held his voluminous skirts in his hand and swayed back and forth while batting his eyelids. Then he lifted up his skirts higher and put one knee and then the other on the sofa so he was straddling Etta’s legs. He arranged his skirts evenly on both sides of Etta and then leaned in wrapping his arms around her head so her face was in the gap between his breasts. Then he lowered himself so he was sitting on her thighs. He held her and kissed Etta on the lips. She put her arms around him and held him tightly. She pressed her mouth hard on his and Winthrop felt her tongue powerfully enter his mouth and he sucked on it. This was all new to him. Etta kissed him hard for the longest time until she removed her tongue and leaned back. Winthrop was breathing hard.

“Oh my God, Etta. That was so magical. I love you so much,” Winthrop said.

“Perfume and lipstick. High heels! Such a pretty dress. So sexy, Winthrop. How can any girl resist?”

Winthrop laughed triumphantly and continued to clutch Etta. He felt her hands working their way under his skirt and petticoats until they reached his thighs. Then they explored the outside of his girdle feeling the boner within. After a while, Winthrop got up and slid his knees onto the floor in front of Etta. He lifted her skirt and put his head inside up to her panties. He reached his arms in and attempted to pull Etta’s panties down causing her to slide forward to help him. When her hips reached the edge of the sofa, Winthrop was able to remove her panties. Etta spread her legs apart and Winthrop eagerly began to once again lick and suck on Etta’s lovely vagina.

“There’s something magical about having one’s pussy licked by a feminine girl dressed so prettily,” Etta said. “I’m sure you look better in that dress than I ever did. You look so good in heels, Winthrop. Your legs are perfectly graced by them.”

“Thank you,” Winthrop mumbled.

Etta put her hand on the back of Winthrop’s head and pushed his face harder against her pussy. “That’s good. Right there. Wonderful spot, Winthrop.” Etta and Winthrop fell into a rhythm with his tongue and slight movement of his head controlled by her tight grip. In short order, she came, and without missing a beat came again a few minutes later. “Now I’m wonderfully warmed up, Winthrop. It’s time for us to fuck.”

Etta took Winthrop’s hand and led him upstairs to her bedroom. Laughing, she pushed Winthrop so that he fell backward onto her bed. Etta lifted up his dress and petticoats, pulled down his panty girdle and panty freeing up his penis. She then proceeded to have her way with him. Etta was able to secure more orgasms before Winthrop shot off himself.

After they rested awhile, Winthrop said, “So I successfully seduced you?”

“Yes, Winthrop. You’ve found my Achilles heel. I can’t resist the seduction of a pretty, girl like yourself.”

“So we can keep on meeting?”

“Yes, Winthrop, I’d like that.”

“I’m so relieved.”

“Going forward I believe we’re equal partners in our dalliances.”

“Partners? I like that. I’ll like being your partner. I love you and being your partner is pretty neat!”

“I should tell you that I’ll be unavailable for several days since Kathleen is returning home. As soon as she’s settled into her summer routine I’ll call you to make an appointment for us to fuck.”

“Okay. I’ll try and be patient.” The truth was that having to wait many days to be with Etta was going to be hard.

When Winthrop was ready to return home an hour later, Etta spontaneously took off her panties and gave them to him.

“Enjoy these until we see each other again. Don’t show them to your mom and dad. If you do, don’t tell them they’re mine.” Etta laughed.

“You mean I can wear these?”

“You can wear them or, you also might want to cuddle with them at night next to your nose. Vaginas produce odors that are intoxicating to boys as I think you’ve already found out from licking me.”

It was true. The thought of Etta’s pussy and its sweet smell was one of the reasons Winthrop was so smitten with her.

“Lie there at night enjoying my vaginal siren song and it’ll take away your sadness.”

“I can’t thank you enough, Etta. I’ll definitely do that.”

“My pleasure.”

***

That night, with the lights out, Winthrop held Etta’s panty up to his face. He inhaled her pheromones and felt renewed happiness in his heart. Etta’s pussy produced a mysterious and exotic scent that was addictive.

Two days later Winthrop’s mom informed him that Kathleen was back from college. “Etta says that in about a week you and Kathleen could have a date together.”

“Can’t wait,” Winthrop said, sarcastically.

“Don’t be like that.”

“Kathleen is too pretty for me and too smart and talented. There’s nothing about me that will attract her.”

“You don’t know the truth until you actually go out on a date with her.”

There was nothing Winthrop could do to change his mother’s mind. He’d have his disastrous date with Kathleen and that would be that!

Winthrop expected to hear from Etta any day which kept him listening for the phone. Finally she called. Etta said, “Kathleen’s off to work and Lou doesn’t return until tomorrow. Can you come this afternoon at one?”

“You bet!”

“I’m going to dress you a little more sophisticated this time. A slinky tight-fitting dress to show off your curves. We’ll go with one of my open bottom girdles so I have easy access.”

“That sounds wonderful!” Winthrop exclaimed. He was so looking forward to dressing up as a girl again. He had taken to wearing Etta’s panties, which was nice, but he longed to wear a bra again and have breasts. He wondered if Etta would give him one of her old bras so he could practice wearing it when his parents weren’t home.

***

When Winthrop arrived at Etta’s house she ushered him up to her bedroom. “We’ve got the whole afternoon to reacquaint ourselves with each other.”

“I’m so excited. I’ve missed you so much. Should I get undressed?” Winthrop asked.

“You’re eager, aren’t you! Sure. Strip down, I’ve got your outfit waiting for you.” Etta fetched a light blue dress from her closet and showed it to Winthrop.

“It’s pretty,” Winthrop said.

When he was naked, Etta said, “There’s that wonderful boner, Winthrop. I’ll have fun with that soon enough.”

Winthrop was glad that he had at least one thing that Etta might have a hard time giving up. Etta handed him panties to put on. Then she helped him on with a bra. Next was an open-bottomed girdled that sparked a flood of questions from Winthrop until Etta insisted that he just wear it and enjoy it. “I’m sorry, Etta. It’s just so fascinating.”

“I know. A miracle of engineering.”

“I agree,” Winthrop said. “I love the lacy, panel like a diamond in the front and the shiny material in the back. It’s just amazing.”

“I’m so happy you appreciate it Winthrop.”

Etta gave stockings to Winthrop to put on. Winthrop stepped into the dress and pulled it up and put his arms into the armholes. Etta zipped him up. “Oh my God, Etta. I love this dress!” As Etta had said the dress accentuated Winthrop’s curves. His breasts projected nicely in the front and his smallish curvy ass was sweetly framed in the back. Etta took him to the bathroom mirror to get a complete view of himself.

“My oh my are you sexy Winthrop. How about a little makeup today to add to your gorgeousness!”

“I’d like that.”

Etta added a little blush to Winthrop’s face, some mascara and lipstick. “Etta, I so love makeup!”

“You’re such a girl Winthrop.”

Etta had heels for Winthrop to wear and they went downstairs to the living room. When Etta sat on the sofa, Winthrop hiked up his tight skirt a bit and straddled her legs and faced her. He kissed her on the lips and Etta held him and tongue kissed him. The accumulated days of passion drove Winthrop to whisper in Etta’s ear, “Can we make love now? Please!”

“Okay, but how would you like to first be nursed? My nipples are buzzing with a need to be sucked on by a cute boy dressed as a girl. Don’t ask me why!”

“I’d love that very much!” Winthrop felt his boner throbbing with desire. He had been wondering when Etta would give him permission to suck on her tits.

“Lie down with your head in my lap,” Etta said.

Winthrop lay on the sofa watching with bulging eyes as Etta lifted her blouse over her head exposing her white bra underneath. She undid the clasp behind her back and removed her bra. Her breasts hung inches from Winthrop’s face. “Time to nurse you, Winthrop. Remember what I said about sucking. Not too hard and not too soft. I’ll help you get it right.”

Etta guided a breast to Winthrop’s waiting mouth and he latched on feeling Etta’s nipple swell and harden. It was sublime. He sucked avidly and with great intensity. This was an experience he would treasure for the rest of his life. He felt Etta insert her hand up his thigh and into the girdle. A moment later she had wriggled it inside his panty and was holding his cock. After what seemed like an eternity Etta pulled her tit from Winthrop’s mouth and moved the other one into position. Etta moaned softly throughout Winthrop’s ministrations to her nipples. Apparently, Etta derived considerable pleasure from nursing him.

Winthrop’s thoughts drifted off to a place of joyful relaxation as he suckled. Etta closed her eyes and was relishing each delicious pulse of pleasure from her breasts when the front door opened and Kathleen walked into the living room.

“What in the world!!” Kathleen said.

Startled, Winthrop sat up and Etta covered her breasts with her hands. “What are you doing home, Kathleen?” Etta found her blouse and put it on over her head. She held her bra in her hand.

“What are you doing with … oh my God it’s Winthrop! Mom, are you nursing Winthrop? And he’s wearing a dress!”

Etta stared at Kathleen not knowing what to say. Winthrop rushed toward the stairs to change out of the dress when Kathleen said, “Don’t go, Winthrop.” He stopped and turned to look at her.

“Mom and Winthrop! I never would have thought that you two are carrying on together.”

“I’d like to explain,” Etta said.

“You’re more than twenty years older than Winthrop.”

“I’m well aware.”

“What about dad?”

“He doesn’t know about it.”

“If he finds out he’s liable to kill Winthrop!”

“Kathleen, you’re not going to tell him are you?”

“I need to know what you two are doing together.”

“Your mom wanted to help me meet girls,” Winthrop said.

“Let me explain,” Etta said. “I felt sorry for Winthrop since he’s never had a girlfriend and he was still a virgin. So I had him come over to see if I could teach him about girls. That went very well, but in the process of teaching him about bras and panties and then boobs and pussies, I realized that shyness is not Winthrop’s problem. His problem is he wants to be a girl in his relationships with girls. That led to my deflowering him and dressing him in the role that he’s most suited for.”

“I guess that’s very sweet of you Mom, but what about dad in all of this?” Kathleen said.

“No parent likes to discuss this with their children, but I’ll tell you. As much as I love your father and want to be faithful to him, his libido has fallen so much that I’m very unfulfilled sexually in my marriage. Lou has relegated my sexual needs to anything other than himself. I’ve talked about it with him and he just says that he’s lost interest. While vibrators are fun, every so often you just want to have a nice cock inside you. I’ve contemplated for a long time what I could do about it and then Winthrop fell into my lap. It’s the perfect situation. We can give each other mutual pleasure without any complications. With Winthrop I feel like I’m being a mentor to a young innocent girl, teaching her the facts of life. Lou has nothing to be worried about since Winthrop is hardly a male.”

“This is all true, Winthrop? You’re wearing a dress because you want to?”

“Yes, Kathleen. I love the girlish ways that Etta has enabled me to dress. Last week I wore the prettiest pink dress and petticoats. That was so much fun.”

“Well, this is pretty interesting and not at all what I was expecting from Winthrop,” Kathleen said. “He and I have a date next week. I don’t know how I can date the boy that my mom is fucking – even if she’s doing it for a good cause.”

“I told my mom so many times that you’re too pretty and too smart for me,” Winthrop said to Kathleen. “Now, on top of that, you see that I’m not even a real boy.”

“Winthrop, it’s not that I don’t want to date you. With this revelation, I want to date you more than ever,” Kathleen said.

“What are you saying?” Etta said.

“Mom. You’ve always misjudged me,” Kathleen said. “I’ve long wanted my boyfriend to be a crossdresser, but I never had any idea how to find one. A lot of them are secretive. Moreover, the flamboyant ones probably aren’t interested in a straight girl like me.”

“How long have you felt this way?” Etta asked.

“When I first realized that dad is kind of over-the-top masculine. That got me to think about boys that had no muscles and then I was watching an old movie with a young girl in a pretty dress and it came to me that it would be nice if my boyfriend were wearing the dress. I got this sudden sexual arousal. It was weird. Ever since I’ve been haunted by that image.”

“I guess like mother, like daughter,” Winthrop chimed in.

“I never knew any of that about you, Kathleen,” Etta said.

At that moment, the front door flew open and Lou stepped in with his suitcase.

“Lou!” Etta gasped.

“Hey Etta!” Lou gave her a hug and kissed her. “And Kathleen’s here! Hey baby!” Kathleen and Lou hugged.

“You’re back early!” Etta said.

“Yeah, today’s meeting was scrubbed so I caught a flight home today.” Lou noticed Winthrop. “Who’s this pretty girl?”

Lou stared at Winthrop while Etta and Kathleen froze unable to think of what to say. Suddenly Lou exclaimed, “Holy shit, it’s Winthrop! Wearing a dress? What is going on here with you ladies?”

“Winthrop and Kathleen are dating,” Etta said. She looked at Kathleen with her eyes begging her to play along with the story.

“Yeah dad. I discovered that Winthrop likes dressing as a girl and I find it kind of cute. I was just showing off how pretty Winthrop is to mom when you came home.”

Lou shook his head vigorously trying to come to terms with what Kathleen had just said. “Do your parents know about you having this predilection?” Lou asked Winthrop.

“No, Mr. Hutchinson. I’m too embarrassed to tell my parents about my cross dressing. I beg you to please not say anything.”

“You shouldn’t reveal his secret, Lou,” Etta said. “He’s old enough to wear any clothing he wants. When he’s ready to tell his parents that he likes dressing like a girl, then he’ll tell them.”

“Yes, Daddy. Please don’t tell Winthrop’s parents.”

“Okay, okay. I’ll keep my mouth shut, but this is the darndest thing. You think you know someone well and then you find out that they’re very different than what you thought.”

“Thank you sir,” Winthrop said.

“Do you dress like a girl at Princeton?” Lou asked.

“No. I didn’t.”

“Well it’s none of my business. But really Kathleen, that’s the kind of boy you like?”

“Dad. I’m rebelling from you!” Kathleen said, and Lou laughed.

“I gotcha. Well, this day and age is crazy. Everybody gets to be who they are.” Lou took his suitcase upstairs to washup and relax.

When he was gone, Kathleen said, “So what are we going to do Mom? You’ve had Winthrop all to yourself. I saw you nursing him. That’s the kind of thing that I’d love to do also. Especially with Winthrop dressed in the pretty dress and showing off his figure.” Kathleen walked over to Winthrop and lifted up his skirt enough to see what he was wearing underneath. “A girdle! How sexy that is. Mom. A boy in a bra and girdle is one of my favorite fantasies!”

“It’s highly immoral for a mom and her daughter to share the same boy,” Etta said.

“As a threesome, yes. But separately? Does it matter?” Kathleen said.

“Look. Winthrop and I have fucked a few times, you know. That went very well and the two of us are hoping to do more.”

“Hey mom. Guess who saved the day with dad? I played along so you should reward me. If Winthrop is so good at fucking, I’d like to fuck him too. Shouldn’t I have some good fucks?”

“Kathleen, you’re being ridiculous. Anyway I have first dibs.”

“I’m only asking for some parttime opportunities with Winthrop.” Kathleen was silent a second and said, “Oh wait. There must be something about him that you’re hiding from me. Does he have a really big dick? Is that it? It’s much bigger than Dad’s?”

“You’ve never seen your dad’s.”

“Maybe not, but I once overheard you talking to Winthrop’s mom about having a husband with an average size and you were wondering what it would be like with a bigger one.”

“Little ears! Since when do kids eavesdrop on their parents? Let’s see what Winthrop says. Honey, do you want to fuck only me, or do you also want to fuck Kathleen?”

Winthrop stared back and forth between the two ladies not knowing what he could possibly say. His emotions caught up with him and he began crying. Etta and Kathleen came up to him and simultaneously held him. “There, there, my little Winthrop,” Etta said. “We’re being too hard on you.”

“Yes Winthrop. I know I’m unfairly muscling in on my mom’s territory, but I’ve fantasized about a boy like you for a long time, so I’m kind of anxious to experience what it’s like. Since my mom loves having sex with you, you must be a great lover.”

“Okay, okay, okay. This is ridiculous,” Etta said. “I get Winthrop whenever your dad is on a trip out of town, and you can have Winthrop when he’s here. That way we won’t have to scurry around being afraid of being caught by Lou. He certainly won’t meddle in Kathleen’s relationship with Winthrop.”

“I like that idea, Mom. What about you Winthrop? Would you be willing to have sex with me besides Mom?”

“As long as Etta gives me permission, then sure. I’m happy to be your girl sex partner like I am with Etta.”

“Since Dad’s home for the next week,” Kathleen said, “I should have Winthrop for myself tonight.”

“Sure, Kathleen,” Etta said, “I guess that’s okay. I’ll just have to use my vibrator tonight. Take Winthrop up to your bedroom and have your way with him.”

“Thanks, Mom, you’re the best!”

Kathleen took Winthrop’s hand and led him up the stairs to her bedroom. On the way she said, “Before we fuck, would you like to be nursed by me? My breasts are about the same size as my mom’s.”

“Sure. I think I’d like that.”

“Great. You’re so very pretty in this dress. I’ve got many nice dresses you can wear. Also my bras and panties should fit you. When we’re done today, I’ll send you home with the panty I’m wearing.”

“Great. Can I also have a bra, an old bra I could borrow?”

“Sure, Winthrop. I’m certain I can find a bra to give you.”

“Thank you, Kathleen.”

“I hope you understand, Winthrop, that by the end of the summer there’s a good chance that you’re going to be all mine.”

“But what about Etta?”

“When you and I fall in love, she’ll give you to me. She’s a great mom.”

“We’re going to fall in love?”

“Of course. You’re too cute for me to pass up, and lord knows you feel lucky to be my boyfriend.”

Winthrop laughed. “I’ve always known how smart you are!”

“I’ll take my bra off and let’s see how much you enjoy sucking on my nipples.”

“Okay.”

“And yes, I’m anxious to see what you've got inside that girdle!”

The End