The Babysitter - Part 3

The Babysitter - Part 3
By Petatonic

Thanksgiving can be a hectic time for most families, and mine was no exception. We had Thanksgiving dinner with Mom’s family on the actual day, and celebrated with Dad’s family on the Saturday thereafter.

On Thanksgiving day, we hosted the dinner for Mom’s parents and her brother’s family. I only have one cousin on my Mother’s side, and he is in his twenties. The ‘men’ watched football and the ‘women’ prepared the food. I wore androgynous slacks and a white shirt, and the day was pretty much uneventful. There were some comments about my haircut, but nothing came of it.

Saturday was different. We all met at my grandparents’ house, which was about a two hour drive away. Dad came from a large family, and all of them were there, with spouses and children.

On the way, Emily called me Tinkerbell. Immediately I objected. “Mom, make her stop calling me Tinkerbell,” I complained.

“Emily, don’t call your brother Tinkerbell,” Mother instructed.

“Okay,” Emily answered, “but only for today,”

When we arrived, Dad and my uncles watched some football and drank beer. Mom and my aunts fussed around in the kitchen, getting in each other’s way. I hung around with those of my male cousins who were more or less around my age and watched the games. Emily sat with her female cousins, talking. During a commercial break, I got up from watching football and went to get some snacks and something to drink, and happened to pass my sister and girl cousins.

“While you’re up, Tinkerbell, get me some more popcorn,” Emily said. I shot her a dirty look.

“Tinkerbell?” one of my female cousins asked.

“Oops,” my sister said with a total lack of sincerity, “I’m not supposed to call him that.”

“But why did you?” another cousin asked.

“Look at his hair. He has a pixie cut. Doesn’t he look like Tinkerbell?” Emily said.

While Emily was supposed to not call me Tinkerbell, Mother’s commandment to her had no effect on my cousins. “Now that you mention it, he does,” commented my cousin Ruth.

“With a little makeup, the resemblance would be improved,” another cousin said. I noted that several hands went into purses, and mascara and lipsticks magically appeared. It was clear that a hasty retreat was called for, and I hurried back to the football game.

I tried to remain invisible the rest of the day, but to no avail. After dinner, one of my girl cousins motioned me to come over to her. “Your sister said I should ask you about your Halloween costume. By the way, aren’t you a little old for Halloween costumes and trick and treating?” she said.

“I took my baby sister and some of the kids I babysat for around for trick or treating. I hadn’t planned to wear a costume, but one of the Mothers had a costume and she loaned it to me.” I said.

At this point, Emily piped up, and said, “Tell them about the costume, and don’t forget to mention that you wore it to school on Halloween.”

I decided to refuse to answer that request, and started to walk away. “Not so fast,” one of my cousins said, and grabbed my arm. “We want to know about the costume!”

“If he won’t tell you, I guess I’ll have to,” Emily said. “He dressed as a witch.”

“You mean like a dress and all that stuff?” another cousin asked.

“Naturally,” Emily said. “He sits for the Benson girls, and Mrs. Benson had the long black dress and a witch’s hat. Not only that, but the dress had a big slit up the side. Guess what he wore under the dress.”


“Panties, pantyhose and a black slip with lots of lace at the hem,” Emily said with a smug look on her face. “Wait, I might have a photo on my phone.”

Unknown to me she did, and it was passed from cousin to cousin. “You really look like a girl in that dress,” one said, “I like the makeup.”

“Do you like dressing up as a girl, Tinkerbell?” another asked. I walked away before I had to answer that question.

Later on, Emily said to me, “The girls want more pictures of you in a dress, and they asked me to loan one to you. You should be thankful that I didn’t tell them that you have your own dresses.” With that, she started giggling.

That Thanksgiving I only had one thing to be thankful for: none of my cousins went to my school.


Joe was over at my house a week later. It was Sunday, and we were in my room preparing for a test on Monday. I had been babysitting the night before, and while I had hung up my blue dress in my closet, I had not closed the door all the way. I guess the color caught Joe’s attention, because he walked over to the closet and opened the door. He pointed at the dress and looked at me. “What’s this?” he asked.

“None of you business,” I replied.

“Is it yours?” he asked.

“Like I said, none of your business,” I answered.

“You don’t deny it, so it must be yours,” he crowed. “You have to let me see you wearing it.”

“I thought we settled all this when I showed you my Halloween costume,” I said.

“But this is different,” he said.

“Look, if you keep this up our study sessions are over. No more help,” I said. Joe knew that this was a real threat, because my help had made a difference in his grades.

“Okay, Okay, I’ll drop it,” he conceded, but I had the feeling it wasn’t quite over.


I had made an appointment to sit for Mrs. Sloan’s daughter on Friday night. Since Mrs. Sloan expected it to be a late night, she suggested that I stay the night. She also said that she and Ellen would pick me up at 5:30 and have supper for us.

That Friday, Joe and I walked home from school together, and sat around my house. At 4:45 I realized that I had to get ready, but Joe hadn’t left yet. “Hey, I’ve got to get ready for a sitting job,” I said, hinting that it was time for Joe to go home. He didn’t get the hint.

“I want you to go home, now!” I finally said, forcefully. Well, maybe a little too forcefully, because Emily heard it and stuck her head in the door.

“What’s wrong?” she said.

“I have to get ready for a babysitting job and Joe won’t leave me alone,” I answered.

“I don’t understand,” said Joe. “I’m not bothering him, I’m just keeping him company.”

“He’s not bothering you,” Emily said with a wicked smile on her face, “so what’s the problem?”

“You know what,” I said to Emily.

“Oh, that,” she said.

“Yes, that,” I responded.

“But Joe might like it and find it interesting,” she said, “let me help you to get ready.” With that she went into my closet, pulled out my overnight case, and put it on the bed. It was obvious that we had Joe’s attention. I didn’t think that a four alarm fire would get him to leave.

I had packed the overnight case with my babysitting clothes, including two sets of panties, pantyhose, and training bra. Emily picked out one set and handed it to me. “Go take your shower, Tinkerbell, and I’ll take care of the rest,” she said with a smirk on her face. I grabbed the clothes and headed for the bathroom, but not before I heard her say to Joe, “Tinkerbell likes to dress up as a girl for her babysitting jobs.”

After a quick shower, I came back wearing panties and bra. I sat down and started putting on my pantyhose. I really had Joe’s attention as I ran my hands up my legs to smooth out my pantyhose. “I could help you with that,” he volunteered.

“No thanks, I can do it myself,” I said. It was then that I noticed a bulge in Joe’s pants. “Maybe you should go in the bathroom and take care of that,” I said, pointing at his crotch.

“Maybe you could help me,” he said.

“No way, you pervert.” I replied.

“Look at who’s calling me a pervert. A boy wearing panties,” he said, with a smile on his face.

I tried to ignore him as well as I could, and put on a slip. I then retrieved my blue dress from the closet, the same blue dress that had started everything, put it over my head, and smoothed it over my body.

I turned my back to Joe and said, “You might as well make yourself useful and zip me up,” which he did. I then went to my closet and picked up a pair of one inch heels, which I then put on. I reached into the overnight case and retrieved my makeup bag, fake pearl necklace and bracelet, and began putting on some mascara and lipstick.

“Your lips look so kissable with the lipstick,” Joe said. I scowled at him, “no pajamas?” he said.

“I have some at Mrs. Sloan’s house,” I said, omitting to say that what I had as her house was a satin nightgown and chiffon negligee.

I finished packing by putting some homework and books to read to Ellen in the case. I then started arranging my hair in an unmistakable pixie style.

I turned to Joe. “Okay?”

“More than okay, you’re gorgeous,” he said.

Mother called upstairs to tell me that Mrs. Sloan and her daughter Ellen were out front.

“I guess it’s about time for me to go home,” Joe said.

“About time?” I queried, “It’s more like forty-five minutes late. Not a word to anyone about what just happened,” I added. “If you do, I’ll spread the rumor that you’re hot for me,” I threatened.

“But it wouldn’t be a rumor,” he said, “because it’s true.”

“You’re hopeless,” I said, as I picked up my overnight case, went downstairs, put on a coat and headed to Mrs. Sloan’s car.

When we arrived at her house, Ellen got out of the car and gave me a hug. “There’s Chinese on the table for both of you,” Mrs. Sloan said, “I’m going clubbing, to see who I can pick up, since a certain someone is too young.”

As before, Ellen and I put on our night clothes and I read to her. After that I worked on my homework. About 11:30 Mrs. Sloan opened the door and came in. “Absolutely beautiful,” she said, referring to my satin nightgown and chiffon negligee. “I have a new friend, Sylvia, who should be here any minute. If you don’t want to meet her, you might want to go to your room, but you don’t have to.”

“I have to put my homework away, before I go to bed,” I said. I was half-way through with this when Sylvia arrived.

After Mrs. Sloan introduced us, Sylvia said, “My, oh my, what do we have here? She’s pretty as a picture. I could just eat her up.”

“The paint’s not dry on that picture, she’s only fourteen,” Mrs. Sloan told Sylvia as a warning.

The two women wanted a night-cap and invited me to keep them company. I sat as demurely as I could as they discussed the nightclub and who was there, and very candidly discussed what each of them wanted to do to some of the patrons. It was slightly embarrassing and I began to blush.

“Oh, look,” Sylvia said, “she’s blushing. Isn’t it precious?” I just blushed the more.

While we were sitting, I noticed that Sylvia’s hand was below the table, and Mrs. Sloan was squirming, as if someone was rubbing her leg, which in fact was exactly the case.

“Why don’t we go upstairs,” Mrs. Sloan said.

“Great idea,” Sylvia replied, and she grabbed my hand and all three of us went into Mrs. Sloan’s bedroom. I really wanted to go to my own room and bed, but Sylvia would not let go of my hand.

“Unzip me, please, honey,” Sylvia said as she released my hand.

“Same here, darling,” Mrs. Sloan requested. Both women took off their dresses, and followed it with the rest of their clothes. Mrs. Sloan put on a nightgown, and handed another to Sylvia.

“Now we all match,” declared Sylvia, as she rubbed my behind.

It appeared that things were getting dangerous. “I think that I’ll hit the hay,” I said, and headed for my room and bed.

Sylvia had left by the time Ellen and I rose. I found Mrs. Sloan sitting at the kitchen table, drinking coffee. “I made a pot,” she said, “help yourself.”

When I poured a cup and sat down, Mrs. Sloan said, “Sylvia’s a bit brazen, isn’t she, but that’s exactly what I needed. She’s a really great lover, but you wouldn’t know about that, would you?”

“Hardly,” I replied.

“Well, if you ever wanted to learn, she could give you post-graduate courses,” she said with a snicker.

Before we left for my house, Mrs. Sloan pulled me close to her and gave me a long passionate kiss, which I gladly returned.


There was a threat of snow in the air and the Christmas lights were shining through the twilight. Today was the last day of school until the new year. Naturally, on a weekend night in the Christmas season, I had a babysitting job. This time for as family named Werner. I had not sat for them before. They were friends of the Bensons, and the Bensons were hosting a Christmas party and the Werners, along with my parents and the Carlson were invited but the Werners didn’t have a babysitter. The Bensons recommended me to them.

That was great, but the best part of the evening was that Emily had to stay at home and sit for our sister Ann. I was getting paid and she was not. How wonderful.

“I think that Tinkerbell should give me half of what she gets,” she complained.

“I’ll think about it,” I said, “if you stop calling me Tinkerbell. Otherwise all you get is pixie dust.”

The Werners had two sons, Steve, aged 10 and Robert, aged 11. Babysitting for boys was a new experience for me, and I decided that I would I would not dress as a girl. I didn’t think that they wanted me to read to them, so I didn’t bring a book. Almost as an afterthought I grabbed a deck of cards and put it in my pocket.

Robert made it clear that he didn’t think that he needed a babysitter. It didn’t look like it was going to be an easy evening. I then remembered that I had a deck or cards, and I put it on the kitchen table.

“Do you guys know how to play cards?” I asked.

“Yeah,” answered Robert.

“Any particular games?”

“Nah,” responded Steve.

“How about blackjack?”


So I taught them how to play blackjack. We used uncooked macaroni as pretend money. After that I taught them some of the various poker games.

It was going to be an early evening, and the Werners returned home before the boys’ bedtime. “Did you boys behave yourselves?” she asked them.

“Yeah, Chris taught us some card games,” said Robert.

“Can Chris sit for us again?” asked Steve.

“Well, that’s something new,” said Mr. Werner, “where did you learn to sit for boys?”

“I just remembered what I liked to do when I was their age, and went from there. I listen to what they say, and don’t talk down to them. When I was their age, I liked to hang around with the older boys,” I explained.

“Well, the Bensons were right when they said you are a good babysitter,” Mrs. Werner said, and she paid me along with a good tip.

“If you’re ready, I’ll give you a lift home,” Mr. Werner said. While in the car, he told me that he was a psychologist, and concentrated in gender issues. “I wouldn’t expect that you have any ideas what that’s about, do you?”

“A little,” I answered.

“Do you know what gender dysphoria is?” he asked.

“Yeah, that’s when a boy thinks he should be a girl, and the opposite for girls,” I said.

“Wow, either you are well read, or I may be touching into a sensitive area,” he commented, almost to himself. Nothing more was said until I arrived home.

I had the opportunity to again sit for the Werners a short time later. Before they left for the evening, Mr. Werner said he wanted to talk to me and we went into his study. “You’ve sat for the Carlsons, haven’t you?”

“Yes,” I replied.

“Now you don’t have to answer the next question, in fact you can tell me to mind my own business,” he said. “Do you remember Mrs. Carlson saying that you will be a good mother?” I thought about what he said, and took a few moments before I answered.

“Yes, I remember, and she did say that,” I answered softly.

“Wow,” he said to himself. He then turned and looked directly at me. “Thank you for being candid with me. As I told you, I’m a psychologist, and everything you told me is confidential. I’m not allowed to tell anyone, not even my wife, and certainly not my children.”

When the evening was over, I told my parents how different it was sitting for boys, as opposed to girls.

“But did you have fun?” Mother asked.

“Yeah, I taught them to play blackjack and poker. They loved it, and the evening seemed to fly by,” I answered.

“What did you think of the Werners?” she asked.

“I like them,” I said, especially Mr. Werner. Did you know he is a psychologist?”

“I think I heard that somewhere.” she said.


On the first Monday of the Christmas break, I was contemplating going shopping for Christmas presents. Before I left, Joe called, and I invited him to come along with me. “Maybe we could catch a movie,” he said, and then added, “if you pay for it.”

I had made a list. I would get barrettes or hair bands for the girls for which I sat, and a deck of cards for each of the Werner boys. For Ann, I bought a Barbie Doll, for Mother a CD of oldies, for Dad, a book about golf. That left Emily. I wanted to get something appropriate for her, and that required more thought. That first day, Joe and I just window shopped. I ended up treating Joe to lunch at the food court, and we just wandered aimlessly until it was time for the movie to start. It was an action movie, with lots of car crashes and explosions, but not a lot of plot or quality acting. As usual, I paid for the admission, popcorn and drinks.

Once the movie started, I felt Joe’s hand on my knee. “Stop that,” I whispered, “remember, you promised no touching.”

“But you’re so touchable. When I think about you in a dress I just want to touch you,” he replied in a whisper.

“But you promised,” I responded.

“Sheesh,” he complained. “Okay,” he finally conceded and moved his hand.

But not for long. It might have been fifteen minutes later, and his hand was back, this time rubbing the inside of my thigh. I was tempted to pour what was left of my drink on his head but restrained my impulse. I remembered how Emily used to complain about boys rubbing her leg at the movies.

“Knock it off,” I whispered into his ear.

“But it feels good, doesn’t it?” he said in the nature of a response. I didn’t answer that. Rather, I said, “If you don’t stop now, I’m walking out of the theatre.

“Okay, Okay,” he said.

A half an hour he was at it again. This time he got a physical reaction from me. I couldn’t very well walk out of the theatre with a big bulge in my pants. I was tired of fighting him, so I stood up and moved to a different seat. He did not follow me.

When the movie was over, and we were far enough that no one could hear me, I lit into him. “Joe, you promised. I’m really pissed at you. Come on, both of us are boys. Don’t ever do that again to me.”

“I’m sorry, I thought you’d like it,” he said sheepishly.

“Well I didn’t!” I said emphatically, “I thought I made that perfectly clear the first time you did it.”

Regardless of what I was saying, deep down in me I did like it, not that I’d ever admit it to Joe.

We wandered around the mall, until Joe saw an ice cream store. “Just to show that you’re not mad at me, I’ll let you buy me a shake,” he said.

“What? Where’s the logic in that?” I spouted off.

“I donno,” he said, “I just want a shake.”

“Okay, if you promise to behave yourself,” I said.

“Does ‘behaving’ include behaving badly?” he asked with a silly grin on his face. I didn’t grace that with a comment.


By the end of the week I had all of my Christmas shopping done, which was good, because I had no money left. For me, that was not a problem, because I had three babysitting jobs lined up for Friday, Saturday and Sunday, which would put a good amount of money in the coffers. I finally decided to get Joe a gift card for the ice cream shop, good for ten shakes. For Emily, I bought her a nice maroon skirt.

Buying the skirt was an interesting adventure. Joe was with me and I was dressed androgynously in jeans and a sweater. I had seen the maroon skirt on a mannequin in the window and I looked through the racks of skirts until I found it in the proper size, and took it to the register. The clerk looked me up and down, and with a smirk finally said, “Aren’t you going to try it on, Honey?”

“It’s a gift for my sister,” I explained.

“I’m sure it is,” the clerk responded with a voice dripping with disbelief. “But why don’t you try it on, anyway?” she said.

Joe was no help. “Why don’t you try it on. I’d like to see how you look in it.”

“Listen to your boyfriend.” the clerk said.

I finally gave in and went to the changing room with the skirt. “When you have it on, come out and let me see how it fits you,” the clerk said.

“Yeah, I’d like to see it too,” added Joe.

I put the skirt on and stepped out of the changing room. The devil in me decided to give it a twirl, much to the pleasure of Joe and the clerk. “It fits you well,” the clerk said, “but if you are going to twirl like that you should have a matching pair of panties.”

“She’s right,” said Joe. I just gave him a dirty look, but in the end I bought the panties.


All of the children for whom I bought the gifts seemed to like them, especially Ellen. When I stopped at the Sloan house, Mrs. Sloan invited me inside to give Ellen her present. While there, I saw Sylvia sitting on the couch. I was wearing girls’ jeans and a frilly top under my coat. “Take off your coat and sit next to me,” she said, as she patted the cushion.

“I’ve got to take Ellen to see her doctor, Mrs. Sloan said, “Why don’t you stay here and keep Sylvia company while we’re gone. It shouldn’t be more that an hour.”

“I’ll take good care of her while you’re gone,” Sylvia said. Yeah, like a shark takes care of a food fish, I thought.

Not twenty seconds after the door closed behind Mrs. Sloan and Ellen, Sylvia had her left arm around my shoulder, and her right hand on my knee. Oh boy, I thought, just like Joe in the theatre. I loved what she was doing, but I knew it could quickly get out of control. I finally steeled myself and said, “Remember, I’m only fourteen.”

“That’s right,” Sylvia said, “I kind of forget that when I see you. You may not know it, but you drive me wild.”

“Would a kiss help?” I asked.

“Definitely,” she answered, and we held each other highly and enjoyed a long lingering kiss.

I realized that Sylvia had only seen me as a girl. “Did Mrs. Sloan tell you that I’m a boy?” I asked.

“No, she must have forgotten that. You don’t look like a boy. Are you really a boy?”

“Yes, last time I checked this morning in the shower I was,” I said.

“But you are so delicious as a girl. Having boy parts just makes it ssoooooo much better,” she said with a big grin on her face.

Sylvia and I petted and kissed until Mrs. Sloan and Ellen returned.

“I can hardly wait until you’re eighteen,” Sylvia said.

“Get in line,” responded Mrs. Sloan, with a smile.


After Christmas, Joe and I decided to cruise the mall to see what bargains there were. I was flush with cash from all of my babysitting, and Joe, naturally, had none. I think my purpose of being there was to pay for everything.

“How about a movie?” he suggested.

“Are you paying?” I asked, even though I knew the answer.

“Well, no,” he replied. “I’m kinda broke.”

“I don’t know,” I said. You certainly didn’t behave yourself last time we saw a movie.”

“It’s not my fault,” he said, “when I’m with you I kinda lose control. It’s your fault for being so foxy.”

“Good grief,” I responded.

As we aimlessly walked around the mall, I noticed that Joe was pausing and intently studying some of the dresses in the store windows. “See anything you like?” I asked him.

“I’d like to see you wearing them,” he replied.

“No, not for me, for you. Any you’d like to wear?” As I said it, I noticed that Joe was blushing.

“You’re blushing!” I crowed triumphfully. “You really want to wear a dress!”

“Umm. Err, no,” he stammered.

“Think silky panties caressing your body,” I whispered to him with an evil smile on my face. Joe’s face just got redder. “I could buy you a pair, and you could wear them under your jeans. No one would know except you and I.”

“But you aren’t wearing panties under your jeans,” he protested.

“You never know, and in this case you never will,” I observed saucily.

At this point we were passing a lingerie shop. I grabbed his arm. “Look,” I said with a smirk on my face, “You can go in and buy a pair. I’ll give you the money, and wait out here for you. I’m sure the sales clerks will be MOOOST helpful, but you’ve got to tell them that you’re buying them for yourself.” I had to chuckle at Joe’s obvious discomfort.

“Err, no!” he said.

“Maybe some other time,” I said, continuing to tease him.


Despite his protestations, I think I had him. A thought crossed my mind. Valentines day was coming up. Maybe a Valentine’s day present for Joe? Pink, lace trimmed, with little red hearts? I smiled at my own cleverness.

I looked at my watch. I had a babysitting job tonight with the Bensons. They had invited the Carlsons over for dinner, and I was babysitting the Benson’s girls and the Carlson’s daughter. I had bought a delightful pair of burgundy slacks with a side zipper and some burgundy shoes, both of which I wanted to wear tonight. Unfortunately, the slacks had no pockets. I needed a burgundy purse.

“I need to buy a purse,” I told Joe, “and then I have to get home to get ready for a babysitting job.” I looked around, and saw a store that was likely to have what I wanted. I went over to a display of purses while Joe meandered around.

“Can I help you?” a clerk asked.

“Yes, I need a burgundy purse, not too expensive.” I was wearing masculine clothes and the clerk gave me an odd look. “Oh, not for me,” I lied, “for him. He’s too embarrassed to buy it himself.”

I called to Joe. “Come over here. How is this one?” I asked.

“Alright, I guess,” Joe mumbled. The clerk transferred her odd look from me to Joe.

As we were leaving the store, Joe asked, “Why was the clerk giving me funny looks?”

“I told her that the purse was for you, but you were too embarrassed to buy it yourself.”

“Gee, thanks,” he said sarcastically.

“Get used to the looks. You’ll see a lot of them when you buy lingerie for yourself.”

“Fat chance,” he rejoined.


New Year’s Eve was only a few days away, and babysitters were in high demand. The Bensons had booked me a month ago, and the plan was that I would sit the Benson girls as well as the Carlson’s daughter at the Benson’s house. Because it would be a late night, It was decided that the girls and I would spend the night at the Bensons. This would mean that I needed some sleep wear. I didn’t think that the nightgown and negligee that Mrs. Sloan gave me would be quite appropriate, and, in any event, I kept them at Mrs. Sloan’s house.

It just so happened that Joe was at my house that day. “Mom,” I called out, “I need to go to the mall. Can you take me there?”

“Sure, honey, what do you need?” she asked.

“Some sleep wear for New Year’s Eve,” I responded.

“Can I go along and help you pick something out?” Joe interjected.

“If I let you pick something out, it would most certainly be a ‘naughty nighty,” I said. “I’ll probably end up with some uninteresting pajamas, a terry cloth robe and some plain slippers.”

“Now, I have to get ready, so scoot,” I said.

“I thought I’m going with you to the mall,” he said, “and I can help you get ready.”

“I don’t need your help,” I said.

“Yeah, but it’s more fun when I help,” he said

“Fun for you, not me,” I asserted.

Since Joe made no sign of leaving, I decided to get ready in front of him. Maybe he’ll get embarrassed, and leave, I thought. Not a chance, was my next thought.

So I undressed, until I was totally naked. I noticed Joe staring at my crotch as I started to put on a pair of panties. “Pervert,” I said.

“Me a pervert?” he replied, “Just like the last time you called me that, I’m not the boy wearing panties.” I just gave him a disgusted look as I put on a bra and nylon knee highs.

“No pantyhose, no dress?” he said as he saw the knee highs.

“What is it about you and dresses?” I said, and then I paused, “Oh yeah, now I remember, you want to wear a dress.”

I put on the burgundy slacks that I recently bought, and an ivory blouse with ruffles, to disguise my lack of boobs. I put on my burgundy shoes, and grabbed my burgundy purse. “A little lipgloss and mascara, and I’m ready,” I told no one in particular.

Mother decided to accompany Joe and me on my shopping expedition. True to form, Joe wanted me to get a baby doll that was more chiffon than substance. I, on the other hand, liked a pajama set in ivory satin.

“Those look like boys’ pajamas,” Joe complained.

“No they don’t, the buttons are on the other side, and there’s no fly,” I explained.

“But they’re not very sexy,” he said.

“If you want sexy, go buy yourself a baby doll and wear it,” was my final comment.


New Year’s Eve was hardly exciting for me. Hardly exciting, but profitable. Of course, I enjoyed entertaining the girls as much as they enjoyed me entertaining them. I had brought some sparkling grape juice and some plastic champagne flutes. By 10:45 the girls were drooping, and they would never make it to midnight, so I declared that we were sophisticated New York ladies, and therefore on New York time. That way we could welcome the new year at 11:00 local time, an idea the girls loved.

After the girls were in bed I put on my new pajamas, robe and slippers, put some music on, cleaned up the house and started reading. The Bensons and Carlsons finally rolled in about 1:00 a.m. “You’re still up,” Mrs. Benson said, more of a question that a statement of fact.

“I wanted to make sure that you party animals got home safely,” I responded.

“Yes Mother,” Mrs. Benson said with a laugh. Mrs. Carlson smiled with a knowing look on her face.

I related how the girls and I had spent the evening, and said that they were all safely tucked into bed. “Oh my,” Mrs. Benson said, “you even cleaned up after your little party.”

“Just like a good Mother would,” said Mrs. Carlson, approvingly.

“Those are pretty pajamas and robe,” Mrs. Benson said.

“Thank you,” I said, “I bought them specially for this evening. I wanted to look good for the girls.”

A few minutes later the Carlsons left and everyone retired to bed.

The next morning I was up before anyone else, and started a pot of coffee. Mrs. Benson came into the kitchen a while later and I poured her a cup of coffee. “I could get used to having someone waiting on me like you do,” she commented, with a smile.

“What had you planned for breakfast?” I asked her.

“How about pancakes and bacon?”

I immediately started the breakfast, while Mrs. Benson sat and savored her coffee. “Would you like me to warm that up?” I said, pointing at her coffee cup.

“Yes Mommy, if you please,” she said with a big smile.

I was flipping pancakes when Mr. Benson and the girls showed up in the kitchen. “Something smells awfully great,” said Mr. Benson.

“Chris did everything,” Mrs. Benson said, “all I did was sit here and drink coffee.” She turned to the girls, and asked, “Did you girls have a nice New Years Eve?”

“Oh yes,” responded Susan. “Can we do it again?”

“Maybe,” Mrs. Benson answered, “We’ll have to check it out with Chris.”

On my way back home, I reflected that all in all it had been an enjoyable and profitable evening. I ruminated on how Mrs. Benson and Mrs. Carlson had made reference to me as a Mother, even if it was in fun. Maybe there was a bit of truth in it. I had to admit that I liked being a ‘Mommy.’


My first counseling session for the new year was two weeks after New Year. “It’s time to evaluate your progress so far,” my Counselor said, “so I’ve asked Dr. Werner to join our team. I understand that you might already have met him.” Let me call him in.

Dr. Werner was the same Mr. Werner for whose boys I had babysat. What followed was a whole lot of consents from everyone, since I knew Dr. Werner from outside of the counseling center. I liked Dr. Werner and was happy to have him on my ‘team.”

“One of the problems with this is that I may hear things about you outside of these four walls which might influence me. If you don’t like that, I’ll bow out of the case,” Dr. Werner said.

“What have you heard about Chris?” Mother asked.

“That he is the best babysitter one could ask for. Also there is the opinion that he would, or will, make a great mother,” Dr. Werner replied.

My Mother just beamed.

“Now Chris,” he continued, “I understand that when you sit for girls, you dress in feminine clothes, and when you sit for boys you dress as a boy. Is that true?

“Yes,” I replied, “It just happened that way,” and I explained what had occurred.

“Do you like dressing as a girl, wearing dresses or skirts?” he continued.

“I do,” I said, “it kind of feels just right.” I answered.

“I see,” he said. “How about when you dress as a boy?”

“Well, I really have to for school, or when someone might see me and connect the boy Christopher with the girl Christine.” I replied, “It doesn’t bother me to dress like a boy, but if I could I would always dress like a girl. And then there are the occasions when I dress somewhere in between, when I think that it would be a good idea.”

“From what I’ve heard, you make a very convincing girl,” he added.

“Thanks,” I responded.

“Any problems at school?” he asked.

“Not really,” I answered, “most of the kids think I’m a weird boy with a funny haircut, and pretty much ignore me. One thing I have to watch for is acting like a girl when dressed like a boy.


“Yeah,” I responded, “I have, or maybe had, a friend named Tom. His Mother saw me sitting and walking like a girl, and she found out that I cross dress. She told me to never be alone with Tom. She told me that Tom’s Dad is a homophone.”

“Do you ever see Tom anymore?” he asked.

“Sure, every day at school, and when a group of kids do something, but never alone. I’m kinda scared of his parents.

“Do you ever have sexual urges when you are near Tom?” was the next question.

“No,” I replied.

“Tell me about other friends?”

“I’m sort of friends with some of the girls at school, especially if we went to grade school together, but we’re not close, we don’t share confidences,” I said.

“How about boys?” he asked.

“For the most part, I am friends with some boys from grade school, but not close. I’m pretty much a loner.” I answered. “And then there’s Joe,” I added.

“Joe?” he asked, “tell me about him.”

“He’s probably my closest friend. I’ve known him for ten years. We hang around with each other a lot. He’s the only boy who’s ever seen me in a dress, other than my Halloween costume.”

“Anything sexual there?”

“Yes, I’d guess you’d say so if you’d call a kiss sexual,” I answered. I looked at Mother to see her reaction. She was frowning. I decided to be less than candid about Joe and me.

“So you kissed him?” Dr. Werner asked.

“Or he kissed me,” I said, completing the question.

“How did that make you feel?” he asked.

“As a boy, I was disgusted,” I said, “but the girl deep inside of me kind of liked it.”

At that point the time was up and the session ended. On the way to the car, Mother said, “I didn’t know that about Joe. Maybe you should stop being his friend.”

“Oh Mom,” I complained, “Joe’s the only real friend I have. I can handle him. Don’t worry about him.”


The next day Joe stopped at my house to study for a test. Mother gave him a strange look, which was not lost on Joe. “Your Mother looked at me kind of funny,” he said to me, “Do you know what that’s all about?”

“Yeah, she thinks that you’re after my body,” I answered.

“Well, she’s right,” he responded.

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