My Sweet Greg

By

Pamela

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In freshman physics lab today, Greg asked me out on a date. We were doing an experiment on magnetism and we had to hold a heavy magnet together and he suddenly said, “Jill, would you like to go ice skating with me?” His face was red and he was sweating and his voice was kind of weird and shaking. The abrupt way he just asked me as fast as he could get the words out made me laugh and I could see he was terribly embarrassed. But I then smiled and told him that I’d be happy to go skating with him. He asked, “You are?” and I had to laugh again. I think Greg is cute and have felt that way since the first day of class. From time to time I’ve seen him looking at me and I’ve hoped for a long time that he’d get the courage to ask me out. I’ve tried to give him signals that I like him and now finally he’s asked me.

Greg is taking me to an outside skating rink. I’ll wear my white tights with little tulips on them and a cute, red skating dress. It has a darling skirt and stretchy material that fits really nice over my breasts. I’ll wear one of my special sexy bras that keeps my breasts up a little higher so they project a bit more. I bet Greg is going to love me in this dress. He’ll really flip out. LOL. I hope he’s not so shy that he won’t hold my hand or give me a kiss goodbye.

Greg showed up right on time at my apartment. I live with my parents since I decided to attend the local university. Greg was wearing jeans and his suede coat that I’ve seen before at the college and really like. He was trying so hard to be nonchalant but I could see occasional tremors run through him. Being in my apartment with my parents saying hello and making small talk with him made him really uptight. When he first entered I hadn’t put on my coat yet and Greg saw me in my cute dress and I’m sure he nearly fainted. I know he wasn’t expecting to see me with such an alluring figure, since I never dress like this at school. When we headed out, he seemed so tongue tied that I wondered if he was going to be able to talk at all during the date. I decided that I had to smile a lot and carry the conversation until, thank goodness, he finally relaxed and then the really fun Greg that I hoped was inside him came out from hiding.

Greg is about as good on ice skates as I am. We avoided falling for the most part. It took him almost a half hour to finally take my hand so we could skate around together. After we skated awhile we sat down and had hot chocolate. I unzipped my coat and once again Greg could see my figure. I hope he doesn’t feel so overwhelmed that he’ll always be afraid to hold me and kiss me. His shyness is as endearing as it is frustrating, but I’m hopeful that eventually he’ll realize that he’s dating a girl who’s really eager for him to ask her out, and then he can finally relax once and for all time.

***

It’s been two months that I’ve been dating Greg. It took him over a week to ask me out after we went ice skating. That date ended with him shaking my hand, though we walked home holding hands. Of course, we were both wearing gloves. Anyway, it’s spring now and since our first date we’ve gone to the movies a few times, we’ve gone bowling, and now our next date is to go together to a college dance. We’ll be able to spend the evening together and dance which means that Greg will have to hold me, at least during the slow dances. Recently Greg gave me a little kiss goodnight. I’m hoping that at the dance, he’ll have the courage to give me a real kiss. I hope he knows how to kiss, though I suppose I could teach him, if I have to.

My mom and I went shopping and I bought a new dress for the dance. It has an A-line skirt, really pretty bodice, and a kind of low neckline. My mom treated me to a new lacy pink bra and matching panties for the occasion. The bra is perfect with the dress, because a tiny bit of lace just peeks out from the neckline. When Greg holds me he’s bound to see the pink lace and I hope that titillates him a little bit. I want to get him in the right mood for kissing me. I also hope that he’ll have enough courage at the dance to feel me up. Surely the pink lace peeking out of a girls dress would spur a boy to want to see more. I sure hope so, but knowing Greg, I’ll be happy if he just kisses me.

***

I had so much fun at the dance. Greg is a good dancer, both for fast and slow songs. The slow songs were very dreamy because Greg got bolder and bolder in holding me as the night went on. By the end he was very much making me feel desired. We also stepped outside and found a bench where at long last Greg got the courage to give me some long romantic kisses. Long smoochy kisses where he actually put his tongue in my mouth. He was very timid the way he did that, but at least he did do it. And then I couldn’t really contain myself and I forced my whole tongue into his mouth so he was sucking on my tongue. Boy that felt good. My whole body was tingly. My nipples were particularly tingly and I felt an amazing wetness in my vagina that I don’t think I ever experienced before. I guess I was hot. I was aroused. I’m not used to that kind of strong sexual feeling in my body, but I must say that I really like it and I like that it’s Greg that got me feeling that way.

***

For the two months since the dance, Greg and I have spent a lot of time kissing. Sometimes we kiss for so long that our mouths and tongues begin to ache. School will be out soon and that will mean that we’ll have plenty of extra time to be together. Greg now understands that I’m his girlfriend and he’s my boyfriend. Unfortunately, he has yet to realize that as a boyfriend he gets some privileges. For example, he’s welcome to explore my body. Similarly, as his girlfriend I should have the right to explore his body. I’ve never touched a penis before or even seen one. It’ll be neat when I finally get to see and touch Greg’s but first he’s got to start feeling me up. On many of our dates, my nipples get so tingly that I’m almost desperate for him to touch them. I pray that very soon he gets the courage to have fun with my breasts.

There’s a nice river near us, and Greg and I went there and took a canoe along it for a mile. Then we went ashore at a beautiful grassy embankment and spread a blanket. It was very secluded and private and I lay down and Greg began kissing me and after a while I sort of nudged his hand toward my breast. I guess he picked up on the signal, for a short while later he gently rested his hand over the top of my pink blouse and felt my breast. I sensed passion building up in Greg and the next thing I knew, his hand was exploring both of my breasts. I purposefully moaned a little bit to give him a clear signal that I approved of what he was doing. Greg became confident enough to move his hand inside my blouse to rest it on top of my bra. I can’t begin to describe how excited Greg seemed to be. Then, I impulsively took off my blouse to fully reveal my bra. Of course, I’ve made sure to wear my sexy pink bra for the occasion. If you’re going to get your boyfriend to pay attention to your breasts, then the least you can do is pander to his animal desires by using a very pretty bra to hold your breasts. I happen to have full round, young-girl breasts that are C cup and not the slightest bet saggy. In my lacy pink bra, they are quite wonderfully sexy.

Well you can imagine poor Greg at this point. My beautiful breasts in their pink lacy bra in the sunshine and just waiting for him to feel and nuzzle. To tell you the truth, while I was expecting Greg to enjoy looking at my bra with breasts inside of it, I thought that he would then want to unhook my bra to get at my breasts. Touching them and fondling them I would think would be somewhat more exciting than my bra. But I was surprised when Greg said, “I can’t believe how pretty your bra is. I think it’s got to be the prettiest bra ever made. I love the color and the lace. The pattern of lace is so perfect and I love the straps. I love how the straps lie on your skin and I love how your breasts fill out the cups. It’s so wonderful. You’re so lucky.”

I listened to his compliments with some amusement until he voiced the last phrase, “You’re so lucky.” I must admit that threw me a bit off my stride. Prior to the phrase, it seemed like my boyfriend was finding my bra to be a bit more exciting than the breasts that were being held within it, which as I said was amusing but not all that surprising to me. At least I think I can understand that because a bra is a powerful symbol of girlhood. But the last phrase made me wonder if Greg actually envied the fact that I wear a bra. I decided that I probably misunderstood his meaning. More likely he meant to say, “I’m so lucky,” for getting to fondle my breasts, but he accidentally said, “You’re so lucky.” It’s also possible that he was making a joke about how lucky I was to have a boyfriend who loved my bra so much.

I decided that since I was giving Greg this nice opportunity to feel me up, I needed to get the thrill that I wanted. We were laying side by side and I leaned onto my side and I rested my hand gently over Greg’s crotch. I could feel his hard penis inside his pants which was very thrilling since this was all new to me. For quite some time I had wanted to see and touch a penis and finally I was getting my opportunity. I felt Greg gently touching my breasts and I used my hand to undo the button of his jeans and unbuckle his belt. Then I pulled down his zipper. I asked him if he minded me feeling him up and he moaned something like “Not at all.” My heart was beating faster than it had ever beat before. I so much wanted to feel a live, warm cock and I was bursting with anticipation. I slipped my hand inside Greg’s boxer shorts until my fingers came upon his pubic hair. Then I moved my hand further down until I began feeling the top of his cock. I gasped with excitement. His cock was hard and sort of pushing up. I whispered to Greg, “Please pull down your pants and underpants.”

With his pants down, for the first time in my life I saw a boy’s penis. It was standing straight up pointing to the universe. “So this is what a penis looks like,” I said. “I’ve never seen one before. I like it. It seems a little longer than I imagined it being, and a tad thicker and rounder. It’s a pretty shape. The little shield on top is very cute. I am very pleased.” Greg thanked me for the compliment. I then asked him “How should I touch it?”

He said, “You sort of grasp it and slide your hand up and down slowly and gently. But, you know it might shoot off from being touched. Don’t be surprised.”

“Shoot off?” I asked.

“I mean I could have an orgasm where my sperm shoots out.”

“You don’t want that to happen?” I asked.

“Oh, no, I would really like that, but I just don’t want you to get surprised or think that I’ve been too forward or pushy.”

I laughed at that one and said, “But I asked you to pull down your pants, I don’t think that I have any right to act offended by what happens next!”

“True,” Greg said.

“I really want to touch your penis and I don’t mind at all if I cause it to ejaculate.”

“I’m sorry to say that I do have a pretty sensitive penis compared to what I’ve heard about other guys. Of course I don’t actually know firsthand about other penises! The most sensitive spot on my penis is underneath the end. As you stroke it, you really want to make sure that you brush up against that area. If you do that enough times, then I likely will orgasm.”

“Those are very nice instructions,” I said. “Just relax and let me play with your penis and see if I can do it right. In the meantime, I’d love for you to play with my breasts.”

I then gently encircled Greg’s dick with my hand and felt it’s warmth. I slid my hand up very slowly and gently to the top and then slid it back down. I repeated this a few times and then asked, “How’s that?”

Breathing very hard, Greg said, “Just perfect!”

“It just occurred to me that maybe you also want me to touch your balls. They’re very cute.”

“Yes, I’m sure I’ll like you touching my balls.”

I ran my hand a few more times up and back on Greg’s penis and then had it gently play with his balls. “These seem so delicate, Greg.”

“Yes, they are,” Greg croaked.

“I’ll use one hand on your penis and the other on your balls. How’s that?”

“Fine!” Greg sort of yelped as I now slid one hand along his shaft while the other gently massaged his balls.

It was the weirdest thing, but all of a sudden, I had the distinct feeling that Greg’s penis had gotten a bit stiffer and longer and then he sort of yelled, “I’m sorry!” and his penis convulsed with all this white viscous fluid shooting up into the air like a fountain for a few pulses and then it oozed up and out from the end of his penis running down over my hand. I counted five spasms at the end there. Each with a little bit less cum than the one before. Greg’s whole body seemed to shake while he orgasmed, especially his legs. When it was over I noticed that there was a sort of goopy pile of the white semen accumulated on my hand and in Greg’s pubic hair.

Greg was breathing hard, and when he caught his breath he said, “Oh my God that was so wonderful. Thank you so much! But I feel guilty that I haven’t done anything for you.”

That’s one of the things I most love about Greg. He’s always thoughtful and polite. “I really enjoyed doing that,” I said, “so I’ve already gotten a lot of pleasure from touching you. To be truthful, I don’t know much about my own pleasure. My vagina got very wet while I was doing that to you and it did feel good.”

“I would love to give you pleasure, if you’ll let me,” Greg said.

“Sure,” I said. I hadn’t really thought about my own pleasure and now I was curious as to what might happen if Greg touched me.

“I guess you should take off your pants,” Greg said. I was wearing my jeans and so I unbuttoned them and slid them down my legs. “Wow, your panties match your bra! That’s so neat. The lace is the same and it’s exactly the same pretty pink color.”

I had to laugh because Greg really seemed so genuinely excited by my panties and bra. I thanked Greg for his compliments about my underwear and then pulled my panties down.

“Oh, how beautiful!” Greg exclaimed seeing my pussy for the first time. “It has such a nice little furry covering. It’s so darling. I’ve never seen a vagina before.”

My pubies are kind of soft and blonde and I loved how Greg thought they were furry. “So what happens next?” I asked Greg.

“If you don’t mind, I would love to use my fingers to explore your vagina. I’ll be very, very gentle and if you could just tell me if I’m touching a spot that you like, that would be great. Just relax.”

I told Greg that this was so much fun, and I lay back and relaxed. I felt Greg’s middle finger very lightly touch the slit-like opening of my vagina. It pushed down a bit into me and I think he realized that I was very wet. He gently ran his finger deeper into me and then suddenly I felt a little jolt of pleasure as his finger must have run up against the corner of my clitoris. “That’s good. Near there I have a lot of feeling.”

Now Greg’s finger seemed to home in on the full extent of my clitoris. He said to me, “It seems like when I run my finger along a long hard protrusion you get a lot of pleasure.”

I told Greg that that must be my clitoris and I thanked him for finding it. He continued to rub on that and then he switched to using two fingers. After a while I began to get the most amazing intense feeling in my pussy. I had never had such feelings before and then all of a sudden I knew that something very different was happening to me when the pleasure shot up to the point where I began crying out. My whole vagina pulsed with pleasure and then it reduced back to a more diffused pleasure. Greg removed his fingers from my vagina and we looked at each other. He was smiling from ear to ear. I love that about Greg. He is genuinely happy for the pleasure he gives me. No doubt he got pleasure from pleasuring me in the same way that I got pleasure from touching him, but he could have just ignored my pleasure. Greg is a very special boy and I’m so happy that he’s my boyfriend.

***

For the next few days, Greg and I only saw each other occasionally in school. It’s kind of funny now, because I’ll see him and I know that he has this cute penis lying there inside his jeans and that hopefully I’ll soon get to touch it again. None of the other girls in school have seen it. Thinking about Greg’s penis makes me realize that when he sees me, he very well could be thinking about my breasts and my vagina. I’m happy that he’s the only boy in school who has seen those things.

On the next weekend Greg came over to my apartment to hang out with me. After greeting my parents he joined me in my room. I was in the middle of folding my laundry when Greg walked in. I told him it would take me a few minutes. He sat down and watched me for a minute and then said, “Do you need help?”

“Sure, you can do my bras,” I said spontaneously. I think I said that because of the interest he had shown in my bra last weekend. “Fold them and place them in the second drawer of my dresser. That’s the bra drawer.”

I watched as Greg sorted out the six bras that I had in the laundry. There were three white bras, two pink bras and a blue bra. He seemed fascinated by my bras. It was like he was trying to get as much time as he could with them. All my bras are lacy, just like the pink one I was wearing last week. I just am the kind of girl that prefers pretty underwear. I’ve always been like that.

Greg then said, “All your bras are pretty. That’s one thing I really like about you.”

“What if I didn’t like lace? Some girls just want their bras to be functional. If I wore bras that weren’t particularly pretty, would you be disappointed?”

Greg laughed nervously and said, “Is that a fair question? I like you the way you are. I don’t want you to be different.”

“I’ll take that as a yes,” I said. “And I like you the way you are too, Greg. You’re a boy who likes pretty bras. If you didn’t care about bras, then you wouldn’t be you, would you?”

“I guess not,” Greg said. “Does it freak you out?”

“That you like pretty bras? No, not really. I’m perfectly fine with your liking pretty bras, but I should say that when we’re talking about bras it does make me feel like we’re two girls who’re talking.”

“I seem like a girl to you?”

“Not normally, no. But when we talk bras, then if I didn’t know better I’d think we were two girls. I hope it’s not upsetting to you, Greg. You’re my boyfriend, but the part of you that seems to really love pretty bras does seem like a girlfriend. I’ve many times talked about my bras with my girlfriends. It’s a conversation that girls tend to have if for no other reason than we all start wearing bras at about the same time, so we talk about how we’re becoming women. We discuss the fact that our breasts are getting bigger and we have to change bra size, sometimes every six months or so. We also compare notes on what kind of bras we like and what particular bras in our style are actually comfortable. You see, bras can be a big topic of conversation among girls.”

This little speech of mine seemed to leave Greg not knowing what to say or do. The truth is that he probably doesn’t realize how little I care about how masculine he is. More important to me is that he’s fun to be with. I enjoy talking to him and I find him cute. Also, I know he has a very nice penis which I’ve been spending some time dreaming about. I decided to say to Greg that I didn’t mind if we talked together like two girls. I went even further, just sort of groping along for the right words and I said that I didn’t even mind if Greg wanted to feel like he was a girl while we talked like girls. That seemed to make sense to me since talking like a girl but feeling you’re a boy might be kind of jarring. I said to him, “You know, Greg, it’s okay with me if you have female parts of your personality and it’s also okay if you need to express the female part. Like when you’re excited about my bras I think that I’m hearing the girl in you. She seems to really want to come out at those moments. Tell me if I’m wrong.”

Greg didn’t know what to say, and I realized that he didn’t necessarily know himself very well. His emotion about my bras comes out of a girly place within him that he sort of suspects might be there, but he’s always been too afraid of to explore. What is definitely true to me is that Greg is very happy that I’m understanding about his female side. The more it sinks into him that I’m giving him permission to be whomever he wants to be, the more relaxed he becomes.

We resumed folding my laundry. I watched as Greg lovingly folded my bras and then I had him do my panties. I was about to tell him to fold my panty girdles when my mom entered the room. She saw Greg putting panties in my panty drawer and smiled knowingly at me. I’m close to my mom and she’s often told me that the best kind of boy or man to have a relationship with is one that does things with you. Even if its domestic chores like the laundry or cooking. Having a man interested in folding his wife or girlfriends laundry is a good indicator that he’s someone that will always be nice to you. I know that my mom will later want to talk to me about Greg and my panties. I’ll have to think about how much I can confide in her about him.

Anyway, my mom told me that she and dad would be leaving for a couple of hours to shop for a new lamp. After they left, Greg and I were alone in the apartment and of course, our first thought was that this will be a great time to do some kissing. “Let’s finish the laundry and then we can lie down and …”

“Smooch!” Greg said.

I laughed. It’s so nice that we are often on the same page. I told Greg that he could now fold the couple of panty girdles that were in the laundry. Greg picked up one of them and I watched as he admired it. I could see that this was another instance where his inner girl was trying to come out. He was fascinated by the girdle. It had stretch lace around the legs and I’m sure he would have loved to have one of his own. I felt a desire to make Greg happy so I said to him, “Let me measure you for a bra. Have you ever done that?”

“No,” he said. I could see that my proposition was causing his mind to whirr away in twenty directions at once.

I got a tape measure and lifted his shirt up and over his head. I measured his chest across his small boy-nipples, and said, “36”. That’s exactly the band size for my bras. I’m also a 36. Of course I’m a C cup and you’re an AA cup. The important thing is that my bras will fit you, except for the cups which will be empty.”

“I had no idea we would be the same size,” Greg said.

“I thought you might be. Anyway, it’s good luck isn’t it? Now we know that my bras will fit you. Would you like to wear one of my bras, Greg?”

I never knew that a human being could get as red in the face as Greg got from my question. I said, “Don’t be embarrassed! We know that there’s a part of you that would really like to wear a bra and feel like a girl, so what’s the harm in letting that part of yourself be fulfilled? It doesn’t bother me, in fact, I think it’s kind of fascinating and it also makes me feel closer to you. Like I said before, to the extent we’re both girls, then we can be closer emotionally to each other than we are if we’re opposite sexes. If we’re both wearing bras then we’ll be like two girls. So go ahead and pick out a bra, or do you want me to select one for you?”

At this point Greg mumbled something, but I just went to my bra drawer and took out one of my prettiest pink bras, and then went to my panty drawer and took out it’s matching panty. “OK, Greg, take off your pants and underpants and put on the panties and then the bra. I’ll help you with the bra unless you already know how to put one on.”

“I don’t.”

“No problem. I’ll give you a little lesson.” I watched as Greg took off his pants to reveal that his penis was pointing straight out inside his underpants. He had to struggle to free it from his boxers and then I had another good look at the cock I had been thinking about for a week. It seemed even prettier and well-formed than I remembered. I couldn’t resist holding it in my hand, and then I shook it up and down like it was Greg’s hand and said, “Hello, sir. I’ve missed you.” The silliness of it made both Greg and I laugh. Greg put on the panties though it was hopeless to fit his boner inside them, so he just let it hang outside. Then I put the bra on Greg. First his arms through the straps then I clipped it behind him. I’m pretty sure Greg was in a state of bliss. I told him how pretty he looked, that if anyone looked good in a bra and panty it was him. I said, if I didn’t know better I’d think you were a girl. A very sexy and pretty girl. A girl with a slim sexy figure. Greg couldn’t get a word out, he was so transfixed by his excitement at wearing a bra and panty that he just stood there. I took Greg by the hand, led him to the bed, moved over the remaining clothes to be folded and had him lay down. Then I stripped to my bra and panty and lay next to him. In a flash we were kissing. A long soulful French kiss. Then I broke it off and whispered in Greg’s ear, “I love having a pretty girlfriend like you. I love that we like the same bras and panties.” From the look of Greg’s face, I realized that if I kept up this kind of pillow talk, he would perhaps get a heart attack. Boy was he wound up now! I resumed kissing him and once again put my hand on his lovely penis. I don’t know what got into me, but I was so horny I said, “Would you mind terribly if I put your penis in my mouth?”

Greg was incapable of talk by this point but he seemed to indicate that no he wouldn’t mind. So I slunk down along his body and put my face right up against his penis and examined it from inches away. I couldn’t believe how interesting it was. I especially loved the curves associated with it. The oval shape of Greg’s balls were intoxicating as was a slight bulge in Greg’s penis a little bit beyond the halfway point. The shape of the red skin surrounding his pee hole seemed innocent and tender. I put my mouth over his cock and felt Greg quivering and spasming. I just left my mouth there taking the special pleasure of having this intimacy with Greg. After a few minutes I made tiny movements of my tongue that led Greg to vibrate his leg like it was going to fall off. Having his cock in my mouth was nice and sometime in the future I would give him a complete and satisfying blow job, but today I wanted to watch Greg’s face as he came. I let his penis out of my mouth and sat up against the backboard. I had Greg put his head in my lap so that his eyes could feast on my breasts in my bra. I looked down on this maternal scene, of the bliss in Greg’s face. I said, “My baby is ready to suckle at Mommy’s breast.” I looked at Greg’s darlingly pretty chest with my bra covering it. The sweet lacy panties with his big boner poking up through the leg hole. I wished I had a camera. I reached behind my back and undid my bra and pulled it up so my breast fell onto Greg’s face. I situated his head so that my nipple was touching his lips and I said, “Come on baby girl, drink your milk.” Immediately Greg had my nipple in his mouth and he sucked on me. Whoa, the pleasure was awesome and unexpected. I had the feeling that Greg’s nursing of my tit could actually bring me to a climax. I decided to not take any chances so that while this amazing pleasure rolled into me, I used a finger of my free hand to rub on my clitoris. In a matter of minutes I climaxed, which I’m sure was a big surprise to Greg. When I had calmed down a bit, then I used my hand to rub on Greg’s dick which was as hard and as straight as a flagpole. It didn’t take much until he was orgasming. I watched with new-found love in my heart as waves of pleasure ran through Greg’s eyes and cheeks and forehead. The giving of love and pleasure to someone you love is a heavenly experience. When Greg’s orgasm subsided, I brought some of his cum to my lips to have a little taste. I couldn’t think of anything I had ever eaten that was similar. While the taste wasn’t exactly delicious, it was definitely palatable and I now felt that I was well prepared for the time in the future when I will get Greg to ejaculate directly into my mouth. Hopefully, that will be soon.

We lay together with arms around each other and Greg said, “I love you, Jill.” The sound of those words swept up through my heart and caused me to feel a surge of affection for this beautiful boy/girl that I indeed loved. After a long pause I said, “I love you, Greg.” Then I heard Greg sweetly crying and before I could say anything he said, “You’ve made me so happy that I’m crying. Who knew that happiness could make people cry?”

I’m sure that I’m as happy as Greg. We got up to make ourselves presentable before my parents returned. Greg went to pee and I enjoyed watching him walk in the bra and panty. When he came back I said, “You would also be pretty in my panty girdle. And I have some dresses that would fit you nicely. It could be fun for us if we played dress-up together. You could be my girlfriend and we could pretend that we’re at a dress shop trying to decide what dress to buy for a special occasion. We could even want to be especially sexy for our boyfriends.”

“But this is just pretend right? I would never want a boyfriend,” Greg rushed to say.

“Yes, I’m sorry. You’re my boyfriend and I’m your girlfriend even if we act out fantasies in which you’re my girlfriend.”

***

The next day my mom came to my room to chat after I was done with my homework. “Is there anything you want to talk to me about concerning Greg?”

“You mean the panties?” I said.

“Yes. Since most boys would never be caught dead helping their girlfriends with their underwear, Greg is obviously not like most boys.”

“I know mom. I’ve figured out that Greg sometimes seems to act like a girlfriend and not a boyfriend. Like we could talk about bras together or panties. I know he loves pretty underwear.”

“You don’t seem bothered by it.”

“I think I love Greg and that makes me feel like I should love this part of him also. Is that crazy?”

“No, it’s not crazy. Of course, you have to hope that Greg knows himself well enough that he isn’t going to one day surprise you by pursuing boys, for example.”

“So there’s nothing wrong if sometimes Greg and I can pretend that we’re two girls.”

“Not with me and your father.”

“Really? Dad wouldn’t mind.”

Mom laughed and said, “There are things about your father that you have no idea of.”

“Like what, Mom?”

“I wear the pants in this family in case you’ve never noticed. I give your father permission to act like he’s a forceful dad. But he has to come to me to get my approval on anything he says.”

“I had no idea.”

“Well, I think you’re old enough to understand that now. Men have many weaknesses that a clever woman can exploit to make sure that she’s in control. Greg will clearly always be your little girlfriend. He’s never going to be able to control you. He’s already conceded that his happiness depends on you allowing him to dress up. Mind you, there’s nothing wrong with this as long as you both are happy.”

“I think we’re very happy.”

“So no need to worry.”

“Thanks, Mom.”

***

A couple of weeks later Greg and I finally had another chance to spend a lazy afternoon in my bedroom while my parents were away. We started with kissing since we’ve been waiting so long for a good chance to kiss. Then we touched each other and since I know how much Greg loves my bra and panties, I suggested he pick out a bra and panty and put them on. This time I stuffed the cups with my panties. He really loved the illusion of now having breasts. I said to him that we ought to buy him some breast forms and we agreed that we’d look into how much they cost and where we could get them. I also took the liberty of spending some time reacquainting myself with his amazing penis.

Since we still had hours before my parents were due back I asked Greg if he would like to wear one of my panty girdles instead of panties, and he said sure it would be fun. We had a good laugh as Greg put on my panty girdle since we had to figure out what to do with his boner. We decided to let it be held pointing up by the panty girdle so the underside of his cock was facing out. I really liked that because it made it convenient for me to rub his penis and cause him to get excited. I also liked seeing the bulge which reminded me of what he’s got packed inside there for my later pleasure.

When I had Greg fixed up in my bra and panty girdle, I took off my clothes so I was in my bra and panty. I took off my panty and put on a panty girdle so that Greg and I would look the same. “Now let’s play our shopping game. Is that OK with you?” Greg said it would be great, so we then went into my closet looking for dresses. We pretended to be two girlfriends at the mall, shopping for dresses. I was very happy that Greg seemed to be comfortable playing the part of a girl. I realize his confiding in me about his innermost feelings of femininity had put him in an especially vulnerable position. That kind of openness and the fact that he’s willing to be intimate with me makes me love him even more. Just imagine the courage it takes if you’re a boy to admit to your girlfriend that despite the fact that your body parts are those of a boy, you feel inside that you’re a girl the same way that girls feel.

Our little dress up game worked very well because Greg was marvelous at channeling his inner girl. He knew how to talk and act like a girlfriend of mine. We spent an hour laughing and making jokes while trying on different dresses. The one dress of mine that Greg was most crazy about was a simple cotton dress, pink of course, with a nice wide skirt and tight bodice. At the end of our game he was wearing that dress and we lay down together on the bed in our dresses holding each other. Of course we did some kissing and we felt each other up. I even felt Greg’s breasts now that there was something to feel in them. That made me wonder if I have a lesbian streak in me. Since I was still very much interested in what Greg’s cock was up to, I don’t think that I can be considered a lesbian. Greg and I lay in the bed together in our dresses and affectionately held each other. Eventually our passion arose and we fondled each other until we climaxed.

***

I did some research and found a medical supply store where I could buy a pair of C cup breast forms for Greg. The next time we had a complete afternoon to spend together alone in my apartment I surprised Greg with my nicely wrapped present. Greg opened the box to see the breast forms. I had made sure he already was wearing my bra so I helped him slip the breast forms into the bra cups and we both cheered the delightful effect it made. So now we could both stick out our chests showing off the same size boobs.

“So how do you want to dress today?” I asked Greg. He said that he would like to wear stockings with my black evening dress. I asked him, “Which do you prefer? Pantyhose or stockings and a garter belt? We can go either way.” He said that he’d like to wear a garter belt with stockings. I have a couple of garter belts and I got the pink one for him and a pair of black stockings. While I was helping Greg on with the stockings and clipping them to the garters he said that he wondered if I ever wore a girdle to hold up my stockings. I told that him that I didn’t and I asked him if he would rather wear a girdle than a garter belt.

“It’s just that I think that I’m more a girdle type girl than a garter belt type girl,” Greg said.

I laughed because I’m pretty sure he was joking, but no doubt he was saying that he preferred to wear a girdle. I thought a minute about it and said, “We could go shopping for girdles for you. In the meantime, my mom has some old girdles that she probably never wears anymore. I bet they’ll fit you and she never has to know that we borrowed one for a few hours.”

We went to my mom’s room to look at her girdles. I found three of them and among them a white girdle was clearly Greg’s favorite. Besides being very lacy it had pretty bows on it and fit him perfectly. After he had the girdle on I found myself excited by the way Greg’s butt appeared in the shiny white fabric. “God, Greg, you’re so sexy in the girdle. I could die for that butt. It’s so pretty and round and cute.” I helped him attach the stockings to the garters and then Greg and I admired his figure in the mirror. I helped Greg on with my black evening dress and zipped it up his back. It’s amazing how sexy Greg looked. Now that he had boobs and a cute butt and stockings, he really reminded me of a girl dressed up for an evening soiree. I asked Greg if I could put some make up on him and he very excitedly agreed. I put some rouge on his cheeks, a little bit of eye shadow and lipstick and he and I were both pleased with the result. In the back of my mind I thought that if Greg just had a bit longer hair, then he and I could go out together as two girls. I don’t think in that case anyone would necessarily figure out that Greg was a boy.

Now Greg and I lay down holding each other. He’s wearing my black dress and I’m wearing the pink dress that Greg loves so much. We’re entwined with each other. Two girls wearing dresses who are clearly in love with each other. We lay there peacefully for quite some time. Every so often we’d kiss a little, or I’d put my hand up inside Greg’s open bottom girdle to find out what mood his penis was in. I think Greg and I were as happy as two young lovers could ever be.

We must have drifted off to sleep, since the next thing I knew my mom was standing over the bed looking at the two of us. “Jill,” she said, “wake up.”

I sat up and then Greg awoke and realized that he was caught red handed wearing my black dress. “What’s going on here?” mom said.

“You’re home early,” I said.

“I was a little tired and came home on the bus. Your dad will be back for dinner. You didn’t answer my question.”

Greg stood up and looked so scared that my heart went out to him. He wanted to take off the dress but had no idea how to undue the back zipper. My mom saw his panic also and she went over to him and put her hand on his shoulder and said, “Calm down, Greg. I’m not going to bite your head off. I want to understand what I’m looking at, such as why my daughter’s boyfriend is dressed in a black evening dress and has quite a sexy girl’s figure.”

“I’ll explain, mom,” I said.

“No. I want to hear Greg’s explanation.”

“I’m so sorry,” Greg began to say and then he started to cry. I went over to him and held him while my mother and I smiled and silently shared our inside joke with each other. Greg was so much under my control now.

“I want to see what you’ve got on underneath Jill’s dress,” my mother said, which caused Greg to cry even harder. “I’ll give you a few minutes to calm down.”

My mom sat down waiting for Greg to regain his composure. I held Greg tightly to me and whispered in his ear not to worry. My mother would not be judgmental. Finally he quieted down and I unhooked the top of his dress and lowered the zipper. He helped me lift the dress up over his head exposing his bra, my mom’s white girdle and his stockings.

“Oh my God, is that my girdle?” my mom said.

“Yes,” Greg said, trembling.

“And he’s wearing a bra with breast forms. Wow.”

“It’s all my fault,” Greg said. “I asked Jill if I could wear a girdle to hold up my stockings and she mentioned that you had some girdles. It was wrong of me to borrow one.”

“I’m glad you realize that borrowing your girlfriend’s mother’s girdle without asking for permission is wrong. But it’s not just that you’re wearing my girdle, it’s also that you’re sneaking about in the apartment wearing girl’s underclothing and a dress.”

“You’re right,” Greg said. “I’m really screwed up.”

“No one said you’re screwed up, Greg. It’s just a surprise to anyone who doesn’t know about this side of you. About my girdle, it’s Jill who led you to it. In this case I think you’re both in the wrong. Jill and you should have asked me ahead of time for permission to wear my girdle. I probably would have said yes, since I so very rarely ever wear my old vintage girdles anymore. Nowadays I have some newer ones that I wear. I’ve got a couple of Rago and a Secrets in Lace girdle that I like. Jill’s father finds them very sexy, I might add.”

“I’m so very sorry,” Greg said.

“Sure, Mom, in the future Greg and I will ask for permission.”

Greg started to pull on the girdle as if to take it off and my mom said, “What are you doing Greg?”

“I thought I should take off the girdle.”

“I didn’t say that you have to take it off. If Jill and you want to play this kind of dress up game, it’s fine with me. You don’t have to sneak around behind my back.”

“Thank you mom,” I said. “Isn’t that what I said, Greg? My parents are so understanding.”

Greg mumbled a yes and my mom said, “You know you kids could just buy Greg his own girdles, and bras for that matter. I see he’s wearing one of your bras.”

“We’re the same size, Mom, so it’s been convenient and kind of fun to share clothes.”

“I can see that.”

“But it’s a good idea for Greg and me to go shopping for some pretty underclothes that he could say are his own.”

“I would like Greg to stay for dinner tonight,” my mom said.

“Can you, Greg?” I asked him.

“Sure,” he said.

“Good,” my mom said, “but I insist that you put Jill’s black dress back on. I want you to dress the same as if Jill’s family were not here.”

“Thank you, but what about Jill’s dad?” Greg asked.

My mom and I laughed. “Don’t worry about him. He’ll find your outfit intriguing.”

Poor Greg didn’t know what to make of all this. Greg put the dress back on. I suggested to Greg that we find a pair of shoes for him to wear for dinner. Since he was dressed so nicely in the black evening dress, some nice black shoes would be appropriate. We went through my shoes and found a pair of sandal-like low heels that just fit him. We talked about the different kinds of shoes I have and when I wear them. I also gave him some lessons on makeup and how to style his hair. We even talked about jewelry and we found a nice bracelet to put on Greg’s wrist and a matching necklace around his neck.

Just before dinner my dad came home. There was a bit of a surprise since he had brought my grandparents Leo and Vivian with him to join us for dinner. I had Greg come out to greet them with me. My dad greeted Greg and said, “Is the dress Jill’s idea?”

I said, “Daddy, we both like Greg in a dress. Greg likes wearing dresses.”

“Sure. He does look good in a dress.”

Next I introduced Greg to my Grandma Vivian as “My boyfriend Greg.” She did a double take and said, “This is a boy? What is this mishigas?”

“Greg likes wearing dresses, Grandma.”

“He does? You’re okay with this?”

“I like it, Grandma. Greg is wearing my dress now.”

“I think it’s the dress you wore to Aunt Sylvie’s funeral.”

“Yes, Grandma, I have only one black dress.”

“How come he has a bosom?”

“He and I have the same bra size so he’s wearing one of my bras. We bought breast forms so he can have bosoms like me.”

“A boy who wants bosoms like his girlfriend?” Grandma shook her head and stared at Greg who was so nervous he wasn’t able to say anything. “And stockings. What’s he wearing to hold them up?”

“He’s wearing one of mom’s girdles.”

“Your mother knows about this?”

“She says it’s fine as long as we ask for permission. Anyway I think we’re going to buy Greg some of his own girdles now so he won’t have to borrow mom’s.”

Grandma asked Greg to give her a peek at his girdle, and he raised his skirt a bit so she could see. She said, “I bought that girdle for Jill’s mother years ago. We each had one. I still wear girdles. So I live in a world where my granddaughter’s boyfriend and I both wear girdles.”

Leo came over to greet me and Vivian said, “Come Leo, meet Jill’s boyfriend Greg who wears dresses like the girls.”

Leo did a double take when he saw Greg. “Isn’t that the dress Jill wore at Aunt Sylvie’s funeral?”

“It is,” Grandma said. “We’ve already noted that. If you look inside the dress you’ll find that Greg is wearing a girdle to hold up his stockings. Just like me. Jill, tell your grandpa that you like your boyfriend in a dress and ladies underwear.”

I laughed and said, “I’m afraid that what Grandma said is true. I love Greg when he’s wearing a cute dress. And I love his figure.”

Grandma then said that Greg’s bosom was as big as mine. I said that my bras fit Greg so I bought him breast forms that fit my bra size.”

Grandma said, “Okay, Jill my sweetheart, you win. A boyfriend who looks like a girlfriend is perfect.”

Leo shook his head and said, “I don’t know, Vivian. I think Greg makes a nice girl.”

“He might make a nice girl, but he’s a boy.”

“When you and I were young boys were boys and girls were girls. Now, anybody is anything. It’s a new world Vivian. You get to be what you want to be. Not what everybody tells you what you’re supposed to be. I say, welcome Greg,” Leo said. “If Jill is happy you’re wearing her dress, then I’m happy.”

I exclaimed, “I love you, Grandpa! You’re so hip!”

Grandma Vivian took Greg by the hand and led him to the hallway to talk. When he came back in a few minutes I asked him what Vivian had said to him. “She asked me if I still had the equipment to make babies. I said that I did. She then asked if I was planning to keep my equipment and I said I was. She then said, that okay she can live with the dress and the girdle if that is what you and I want.”

I had to laugh at that. Grandma is very precious. She very much wants my mom to have grandchildren.

We sat down to eat, the six of us and when we were done and having dessert, the doorbell rang. Mom got up to answer it and a moment later she entered the dining room together with Cousin Marvin and Cecille Adams with their son Jimmy in fourth grade and daughter Lana in fifth grade. We quickly found chairs for them around the table. Mom introduced the Adams family to Greg saying that he’s Jill’s boyfriend.”

“Jill has told us so much about you,” Cecille said, and then she laughed, “Except that you wear dresses.”

Once again Greg seemed tongue tied and I intervened telling Cecille that since Greg and I are the same size, I let him wear my dresses.

Cecille said, “That explains it. His dress is so familiar. It must be the one you wore to Aunt Sylvie’s funeral.”

“Exactly. Greg is a little shy, but he’ll warm up, I promise you.”

Marvin said, “Understandable. A guy meets his girlfriend’s family while wearing his girlfriend’s dress.”

“Not just the dress,” Vivian said. “Greg is wearing my daughter’s girdle and Jill’s bra.’

“I think he has a lovely figure,” Jill said. “Don’t you agree, Cousin Marvin?”

“He’s a little slim in the hips, but otherwise it’s quite a nice womanly look that Greg has.”

“Perhaps Greg could wear padded girdles,” Cecille said. “They can really help accentuate the butt.”

I thanked Cecille for the idea. “We’ll have to look into it.” I looked at Greg and smiled and gave him an encouraging face. He seemed to thaw a bit and he also thanked Cecille for the idea.

“Do you wear any other of Jill’s dresses?” Cecille asked Greg.

“Yes,” he said. “The pink dress that she’s wearing now is also one of my favorites.”

After dinner, Grandma Vivian, my mother, Cecille and I went into the kitchen to clean up. I whispered to Greg to visit with my dad and Marvin. He walked over to them and sat down with them. From the kitchen I could see Greg trying to be comfortable. I had previously mentored him on keeping his knees together when he sits in a skirt or dress and I saw him making an effort to do so. Then he crossed his stockinged legs and smoothed his skirt over his lap. I don’t know what the men were discussing, but later he told me they were talking about the gym they belong to and about playing golf. My dad asked him if he preferred spending his free time with the ladies or with the men. It was so cute because Greg’s answer was that he preferred spending his time with me, doing whatever I was doing.

When the ladies joined the men in the living room, Jimmy and Lana came and took Greg and me to my bedroom to play a game with them. We sat on the floor and I enjoyed watching Greg struggle to sit down in a relatively tight skirt without spreading his legs apart. When he finally got comfortable sitting side saddle, Lana began peppering Greg with questions. “Why are you wearing a dress like girls do?” was her first question.

Greg said, “I like dresses.”

“But dresses are for girls.”

“Dresses might be for girls, but boys can wear them if they want to feel like they’re a girl.”

“You want to feel like a girl?”

“I guess you could say that.”

I then said to Lana that I like boys who wear dresses. It shows that they like girls and it’s important for girls to be with boys who like girls.

Lana asked Jimmy if he wanted to wear one of her dresses, and he said, “I don’t know. I’ll have to think about it.”

***

When everyone had gone home, I was very horny and I asked my mom if it was OK for Greg to stay a little while longer in my bedroom. She said I should send him home at midnight which gave us a couple of hours. Mom and Dad settled into a movie in the living room and I closed the door to my room and told Greg to sit on the edge of the bed and lean back. I don’t know if he knew what I had on my mind, but he quickly found out when I pulled the skirt of the black dress up to his belly, and then unzipped and unhooked his girdle and pulled it down to his ankles. Then I had free access to his cock and I got on my knees in front of him and began sucking on it. This was the least I could do for him and me in view of all the stress we had had that evening. While I sucked on Greg’s dick, I thought about how attractive Greg is. From his beautiful penis to his shapely figure. Yes I would be getting him some padded girdles since it would be fun to see him with a girl’s ass. Maybe when I get him some bras, I should go for a D cup or maybe even DD. Why does he have to be my size? I think that Greg would be even sexier with a bigger chest than me. Well, in some ways he is a bit more feminine than I am. Not so much in terms of clothing, but I am clearly the dominant personality. He often behaves like a rather shy girl who fits in best when she’s told what to do. I enjoy the role of telling Greg what’s coming up next with us. This is so pleasant sucking on his dick. I think it’s very sensual and intimate. I enjoy the power it gives me. He’s so hard right now I can imagine how his whole world revolves around my mouth and tongue. Little drips of his pre-cum show up at his pee hole and he’s moaning faintly. I whispered to him to keep it down, I don’t want my mom knocking on the door. It was so much fun to see Grandma and Grandpa deal with Greg in a dress, besides my mom and dad and even the cousins. I think they all realized that as long as I’m in control, it hardly matters whether Greg is wearing a dress or a suit. I do have some work to do on getting him to relax. It’s sort of cute that he freezes up when someone new sees him wearing a dress, but he needs to get more accepting of his role in our relationship. He needs to be more comfortable with people because I want him to be. I’ll have to have a little chat about that with him. I hope Greg proposes to me. I would accept in an instant. I’ll then own this beautiful boy/girl who I can dress anyway I want. I can feast on his body and his penis any time I want to. I can have him suck on me or be my baby or really do anything I want with him. I wonder what sex fantasies he has? We’ve never really talked about that. I could see tying him to the bed, but I doubt that he’d enjoy tying me to the bed. I’m getting goose bumps just thinking about it. Oh my goodness, I think Greg is very close to cumming now. I’m going to keep my mouth over the end of his cock and take the full load into my mouth. I sense his back stiffening and now his legs are beginning to shake and then oh my goodness what a huge squirt of cum onto the roof of my mouth and all over my tongue, and now another one and another one. Gosh will there even be enough room in my mouth for all this cum? I better take a gulp now and make room for more. It’s still seeping out of his cock. This is so intense. To have another human being caught in such a hormonal moment of release. It’s so biological. Thank goodness Greg didn’t scream out, my mother would have come running in here and seen me sucking him off. She probably doesn’t want me doing that in my bedroom. On the other hand, would she be jealous that I get to suck on Greg’s cock? I suppose she likes my dad’s cock. I probably shouldn’t be thinking of that. Oh well. The nice thing about taking all of Greg’s cum in my mouth is that there is no mess anywhere. I think I’ll have to spend some time teaching Greg how to get me off with his tongue. That should be fun. Yes, definitely I want Greg to have DD breasts. I wonder if he’s free to go shopping tomorrow?

The End