Know Thyself

By Pamela

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I was resting comfortably reading a book in a chaise lounge in the back porch of my house, when out of nowhere a FedEx guy showed up and called out to me, “Are you Greg Perkins? I have a package that needs your signature.” Since I was wearing a dress and had obvious breasts I jumped up attempting to run into the house so he couldn’t see me. But he had and he called after me, “Hey man. I see you. I need your signature.”

“I need to change!” I yelled.

“Forget about it man. I don’t care what you’re wearing. That’s your business. I just need your signature.”

I came back and only with the greatest of difficulty was I able to stand next to him in my dress. I took his pen and signed and he said, “It might not be any of my business, but why are you beating yourself up over this? If you want to wear a dress, wear a dress. You’re not harming anyone. It’s a victimless desire on your part.”

“It’s always been my secret. I’m a private person.”

“You seem like you’re ashamed of yourself.”

“I’m not ashamed.”

“Why did you run away in embarrassment?”

I didn’t have an answer and he reached into his pocket and took out a business card and handed it to me. “I just happened to have this on me. It’s for a psychiatrist that is a good friend of my mother. She often handles people with sexual orientation concerns and problems. From everything my mother tells me, she’s really very good.”

With that the FedEx guy turned around and left. I looked at the card and the doctor’s name was Stephanie Nathanson. Below the doctor’s name and address and phone number was the line “Specializing in Unconventional Therapies.” What in the world did that mean, I wondered. I was surprised to see that the psychiatrist was a woman. I had figured that a man would be the one to treat a man, but the FedEx guy didn’t seem to have any issue with that. I imagined what it would be like to tell a man that I liked wearing dresses vs. a woman. Either way I would feel extremely uncomfortable.

I was in a quandary. My life had been fine up to this point. I dressed up as I wished around the house and that was it. I didn’t have a need to venture outdoors in a dress. But the FedEx guy was right. I did feel embarrassed and maybe that was unhealthy. Maybe I needed to explore this side of myself and get to a point where I’d be so well adjusted that I didn’t care what other people thought of me. It might have the consequence that I could develop new and better friendships since I’d be on a more honest footing with people. Anyway, I’d have to sleep on it.

***

Two weeks later I entered the office of Dr. Nathanson. I had deduced from her voice on the phone that she was probably a middle-aged woman, considerably older than my age of 28, but seeing her in person was a shock. She was probably around forty or so, but she was one beautiful woman. She had long, light brown hair and a pretty face that was at once sensual and intelligent. I know a bit about bras from the ones I’ve bought and I strongly suspected that she was wearing a side-support bra that enabled a profound projection of her far-from-insignificant breasts. I wondered if she might be a 36DD. In a tight sweater top I’d be hard pressed not to stare. As it was she was wearing a pretty blouse whose buttons were struggling mightily against the formidable pressure placed on them by her breasts. Combined with the tight skirt and stockings she was wearing and the pretty high-heels I felt somewhat overwhelmed in her presence. Beautiful women have always made me frightfully nervous and Dr. Nathanson had more than enough of that female presence and power to render me incoherent. Waves of seduction seemed to roll out of her that forced me to deploy every bit of self-control so as not to become a blubbering fool.

Besides Dr. Nathanson’s beauty she had a professional presence that was mature and perceptive. I sensed instantly that she would be firmly in control of our sessions. There was no doubt as we faced each other in comfortable chairs that she was in the driver’s seat. She would be calling the shots. There would be nothing I could throw at her that she wouldn’t be able to contend with. I would be emotionally naked in her formidable presence. Nervously I said hello as she greeted me. She asked me how I was referred to her.

“It’s kind of silly,” I said, “but my FedEx driver’s mother is your friend. I don’t know her name, but he gave me your card.”

Dr. Nathanson gazed at me and a slight smile formed on her face. “I see,” she said. “Tell me why you’re here.”

I thought, is that the entire preamble? Now I just launch into my issues? What exactly are my issues? “Oh, okay, Dr. Nathanson. I’m here because …” I hesitated realizing that it would be very lame to say I was here because my FedEx guy advised me to go. I said, “I realized that I might have some low self-esteem issues that I’d like to get past.”

“For instance?”

“Well,” I said, realizing that I had to talk about my wearing dresses or this would be a waste of time, “I sort of like to wear …”

“Wear what?”

“Dresses.”

“Dresses? You mean you like to cross-dress?”

“Yeah. I’m a crossdresser.”

Dr. Nathanson stared at me for much too long a time without saying anything. I had no idea what she was thinking but I began to imagine that she was thinking that this man had no right to claim any part of womanhood. If he thought his cross-dressing would somehow make him a bit like a woman he had some nerve. I was broken out of this reverie when she said, “And how does that give you low self-esteem?”

“I guess I’m embarrassed that I do it. I’m afraid of getting caught.”

Dr. Nathanson’s eyes drilled into me like I could not remember anyone doing to me in a long time. “Do you leave your house wearing a dress?”

“No, I’ve never done that.”

“Then how can you get caught, like you say?”

“I’m sorry. The FedEx guy delivered a box to my house by going to the back porch instead of the front door. He caught me wearing a dress.”

“And the mother of the FedEx guy is my friend?”

“Yes, exactly.”

“So, when he saw you in a dress, he then gave you my card?”

“He saw that I was terribly embarrassed to be seen in a dress. He told me that I shouldn’t be like that and that I needed help to overcome my low self-esteem.”

Dr. Nathanson looked at me with her penetrating eyes and said, “So you were diagnosed by the FedEx guy?”

“Yeah. I know it sounds silly, but he said I shouldn’t feel embarrassed and it was like a light had been turned on. I decided that he’s right. I don’t want to feel embarrassed wearing dresses.”

“I see.”

Dr. Nathanson and I looked at each other. She sat up straight and pushed her arms back in such a way that her chest pushed out and a pattern of wrinkles formed in her blouse around her breasts. She uncrossed and crossed her legs. I noticed an instantaneous view of what must be a lacy white slip that she was wearing underneath her black skirt. I looked at her perfectly manicured pink fingernails and then down at her perfect pink polished toenails visible in her toeless heels. She was the real deal. If I could look like her I would be so happy.

“Tell me about your dresses,” Dr. Nathanson said.

“My dresses?”

“Where did you buy them? Describe them for me.”

“In any particular order?”

“What do you mean?”

“I mean chronologically, or by price or favorites?”

“Greg, I’m not shopping online. Tell me about your favorite dress.”

“I’m sorry, but do you mean among the ones I own now? Because my favorite dress is one that I don’t own yet but would like to.”

“We’ll deal with your fantasy dresses later. Right now I want you to tell me about the favorite dress in your possession.”

“It’s a sheath dress with large flowers on it. Sort of black with bright flowers. I think it fits me perfectly. I feel so comfortable in it. I think it shows off my bust in a nice way. The fabric is kind of soft and rather delicate. I think I look somewhat womanly in it. ”

Dr. Nathanson took extensive notes while I was talking. When I was done I waited while she finished up writing something down. “I see,” she said finally.

“Should I talk about another dress?” I asked.

“No. That should be sufficient for today.”

I couldn’t imagine what in the world she got from my description of the dress. Out of curiosity I asked her. She said, “The way you talk about the dress reveals a lot about your inner person. It’s a window inwards. Of course, one of many that we’ll be looking at over time.”

“What did you find out?”

“It’s much too early to reach any conclusions. I will say, however, that suppose that I was asked to describe the outfit I’m wearing now. I’d say that the skirt and blouse fit me perfectly. I feel very comfortable wearing these clothes. I love how my bust looks in this blouse and the fabrics are soft and sensual. I feel very much like a woman wearing these clothes.”

“That’s what I said about my dress!”

“Yes, exactly, yet I’m a woman and you appear to be a man, at least by outward appearances.”

“Where is this leading to?” I asked.

“So, there is a woman of sorts inside you. Our job here is to understand this woman better and find out more about her. That’s a path that we’ll be following. The first step was to convince ourselves that you have a woman in you, and I think that we’ve answered that affirmatively. If there wasn’t a woman in you, then looking for one would be a waste of time. I think it’s pretty clear that you do not know your inner woman very well at this moment. She tells you to wear dresses and you go along with it but it also embarrasses you. That’s a clue that you need more understanding of who you are. A major goal of ours is to get you this knowledge. Exactly who you are. Woman or man, girl or boy. What kind of woman. What kind of girl. All the nuts and bolts of what makes you up as a crossdresser. If you can get to the point of knowing yourself and who you are, then you will no longer be embarrassed about wearing dresses.”

“Why is that?”

“If you know who you are, then you also know what you cannot be. All your mental gymnastics that go toward trying to be a different person – one who does not wear dresses so cannot be caught wearing one – would be exposed as being useless. Not knowing who you are makes you think you could be different. As our therapy progresses you will realize that for better or worse you are what you are and you’ll no longer care if people have some sort of issue with you wearing a dress.”

To put it mildly, Dr. Nathanson floored me with this precise analysis of what we would be doing in my sessions with her. I had thought it would be vague and incomprehensible, but I had been wrong.

“One other thing, Greg, before you go.”

“What?”

“Part of this process will likely have you falling in love with me. I mean really, seriously, deeply in love. You will love me carnally and spiritually and intellectually. You will see me as a God-like figure in your life. You’ll even worship me in some ways. Just be forewarned.”

“Is that good? What can I do about it?”

“Nothing really. And no, I will not be falling in love with you.”

***

Man, I thought, leaving Dr. Nathanson’s office, this is really heavy-duty stuff we’re talking about. I’ll be trying to figure out who I am, I’ll fall in love with Dr. Nathanson, it won’t be reciprocated. At the end of the day I’ll be healthier and happier than I’ve ever been? Is that even possible?

I wondered if I ought to drop out of this therapy, but realized that would mean not ever seeing Dr. Nathanson again. I knew that I was already falling in love with her and would not give up the chance to spend an hour with her each week.

The revelation that I had a woman inside me generated many kinds of new ideas about myself. Did she have a name? What did she look like? Of course, that was silly. This woman was a personality – she lived within my neurons. The woman was me – not a separate entity from Greg – but Greg himself.

***

At my next appointment with Dr. Nathanson, she said that I should go into a small bathroom leading off from the office and take my clothes off. Then come back to join her. I was astonished at her instructions and said, “Naked? You want me to be naked?”

“Yes. What we do next depends on you being most vulnerable, with nothing to hide behind. Back to the same nakedness you had when you left the womb. I find that naked people are much more inclined to look inwards to find their real selves than clothed people. Being naked also serves the purpose of dispensing with both male and female clothing so your biases toward one or the other will not be an immediate factor in our analysis. I know some patients are uncomfortable at first, but before you know it you won’t give it a second thought.”

“But what about my …”

“You’re what?”

“My private parts?”

“You mean your penis? Greg, I’ve seen many a penis in my day and quite frankly I don’t think that they’re anything people should be afraid to look at.”

My qualms about being naked also had to do with how beautiful Dr. Nathanson was. Nowhere in my dreams and fantasies had I ever imagined that a beautiful woman would see my naked body. The thought was powerfully erotic and I foresaw that I would have a hard-on from the moment I sat down naked in front of her.

I went to the bathroom and took off my clothes. There was a hanger and some hooks on which I neatly arranged my pants and shirt. I stepped back into her office and covered my penis with my hand. The temperature in the office was a tad too cold for me which had the effect of making me feel isolated and puny in my nakedness. I sat down in the chair and nervously awaited what Dr. Nathanson would next ask me. My foot shook a bit. Despite how sexy the doctor was, the cold and the strangeness of the situation took away the possibility of my getting a boner. The reality of being naked in front someone who is fully dressed is a lot different than what I imagined it would be.

Dr. Nathanson stood up and smoothed her skirt. She walked to a bookshelf on the other side of the room. I watched her beautiful womanly figure move. The sway of her ass and her large breasts lighting up the way. She took a thin book, like a children’s book, off the shelf and handed it to me and then sat down. I looked at the cover and the title said, “Is Alice Ready for Her First Bra?”

“I want you to read it to me and describe what is going on in the pictures.”

Surprised, I said, “Read it?”

“Yes, Greg. Read it as I specified.”

It was an illustrated picture book designed probably for girls that were barely ten years old. I turned to the first page where there was a picture of a pretty girl who looked to be about nine years old. She was wearing a tee shirt and staring into a mirror. I said, “There’s a picture of a pretty girl looking at herself in the mirror. She’s wearing a tee shirt and the text says, ‘Alice was wondering if she needed to wear a bra.’”

I looked at Dr. Nathanson and she signaled me to continue. I turned the page and said, “Alice is sitting in a class at school. She can see that the girl sitting in front of her is wearing a bra, I mean it’s from the obvious bra strap running across her back under her blouse. The caption says, ‘Earlier that day at school, Alice saw that Becky had come to class wearing a bra.’ Now there’s a picture of Alice facing Becky. Becky seems to have the beginnings of breasts, I mean her blouse is a bit full where her breasts should be. It says, ‘Alice congratulated Becky on getting her first bra. Becky told Alice that she was becoming a woman now.’”

“The next page has Alice talking to her mother who has a quite formidable chest. Alice is saying, ‘Mom, I think I’m ready for my first bra.’ Then mom steps back to get a good look at Alice’s front and she says, ‘Lift up your blouse so I can see.’”

“The next picture is of Mom looking at Alice’s chest. Alice is holding up her tee shirt but her back is toward us and Mom is looking in our direction so she can see Alice. Mom is saying, ‘You barely have breast buds, Alice. You don’t need a bra yet.’”

I turned the page and said, “Now Alice is crying because her mom doesn’t think she’s ready for a bra. She says, ‘But Becky is wearing a bra and she doesn’t really have breast buds either.’ Her mother is saying, ‘How do you know?’ Alice is frowning because she doesn’t really know if Becky has breast buds or not.”

“Now it looks like Alice is going to bed. She’s wearing a nightgown and she looks like she’s been crying. The caption says, ‘Alice went to sleep miserable because mom said she wasn’t ready to wear a bra.’ The next figure has Mom in the room with Becky saying good night and turning off the light. Her Mom tells her, ‘You’re a year or two too young to get breasts. Most girls are at least ten when they start to see breast buds. Becky is a special case. For sure you’ll soon need a bra. Just not right now and you shouldn’t be embarrassed about not wearing a bra just because Becky is wearing one.’”

“The next picture is of Mom and Alice hugging each other and Mom is saying good night. The last picture has Alice holding out the front of her nightgown so she can look down at her chest. The End,” I said.

“So tell me what you thought of the story,” Dr. Nathanson said.

“I really liked it. At first I was sort of rooting for Alice and hoping that her mom would allow her to wear a bra. Then the reality sank in that she truly doesn’t need a bra. I must admit that I was pretty disappointed that Mom wouldn’t just get her a bra anyway. If Alice wants to wear a bra to school even without having breasts then why not let her? What’s the harm? But maybe Mom is right. I don’t know enough about it.”

“Very good. Now I want to make this same story much more personal for you. But before we do so, it’s helpful if you first get a chance to practice adlibbing your lines. The book we just read is a perfect story to use for this purpose. So we’ll now act out the book you just read to me. You’ll be Alice and I’ll be your mom. Make up your lines and do your best to express how you truly feel. In other words, allow yourself to inhabit the character of Alice.”

I closed my eyes and thought of Alice and then imagined I was her. “Mom, I think I’m ready to wear a bra.”

“Really. You’re a little bit young to need a bra. Let me look to see if you have breast buds. I’m sorry to say that I don’t really see them. You don’t need a bra.”

“But Becky is wearing a bra. Today in class I saw her bra straps and I congratulated her. She told me that she’s becoming a woman. Is she mom? Is Becky becoming a woman now? How come she can wear a bra and become a woman and I can’t?”

“If Becky is getting breast buds then she’s earlier than the other girls in your class. Are any other girls wearing bras?”

“No, just Becky.”

“So Becky is first. There’s always one girl who is first.”

“But I don’t think that Becky has breast buds. I just think her mom was nice to her and bought her a bra.”

“We don’t know the answer to that. If Becky truly doesn’t need a bra just yet, then her mother is not doing Becky a favor. She’ll end up having to wear a bra for almost all her life. Why start early?”

“I want to begin to feel like a woman. Like the way that Becky does.”

“Very good, Greg. That was some good work. Now, we’ll enact this same basic story, but tailored to specific events in your own personal experiences. In this version, you’re playing yourself at the age that you first decided that you wanted to wear a bra. As you’re working through your desire for a bra you’ll have a parent or some other trusted adult such as an aunt or family friend to bounce thoughts off of. I’ll play that person.

“You could be my Aunt Ruth. She’s not really an aunt but a very good friend of my mom and dad and someone that I used to talk to about some of my teenage passions. She was always very supportive and kind.”

“Very good. Begin.”

I thought about what to say and then dived in. “You won’t tell my mom and dad if I tell you a secret, Aunt Ruth?”

“Of course not, Greg. Whatever we say here is only between you and me.”

“I think I might like pretending that I’m a girl.”

“You think or you know?”

“I guess I do like pretending I’m a girl. Is that wrong? Am I sick?”

“Of course not. It only means that you’re going through a natural process of figuring where on the gender spectrum you feel most aligns with your innate feelings. Tell me where this comes from.”

“It first happened early one morning before anyone else was awake and I was lying in bed and I had the sheet across my chest held down by my arms. I looked down and it seemed like I was wearing a strapless dress. I then got the idea to put two rolled-up socks under the sheet so that it looked like I had breasts. Now it really looked like a girl in a strapless dress and I felt deliriously happy as I lay there imagining that I was a girl.”

“Were you thinking that you wanted to magically become a girl?”

“No, I never really thought about that. It was pretending I was a girl that I loved so much.”

“So what happened next?”

“Not long after that, I was in the stairwell at school during the change of classes and just ahead of me was Penny. She was the prettiest girl in the class and she was wearing a short-sleeved white blouse so it must have been assembly day. Somehow I looked up at her and from that angle I could see up the arm hole of her blouse to her bra. It was a good look at a white bra where the cup was covered with lace. I was stunned. I knew that I wanted to be wearing a bra, just like she was. I wished that I could have a bra just like hers. I wanted to get a bra so that I could pretend that I was Penny wearing her bra.”

“After that experience did you get a bra?”

“No. I don’t know how to get a bra by myself.”

“I could talk to your mom about buying you a bra. Would you like me to do that?”

“Then my mom would know that I want to wear a bra.”

“You’re right. Your mom might not be comfortable knowing that you wanted a bra. Then what can I do for you?”

“Don’t you see Aunt Ruth? I’ve realized that I want to wear a bra the same way that girls do. I spend a lot of time everyday dreaming about getting my first bra. I’m jealous of the girls that are already wearing bras. I’m frustrated because I haven’t had a chance to wear a bra like other girls do.”

“Let me stop this here, Greg. I think it makes the point I was expecting that it would make.”

“What’s that, Dr. Nathanson?”

“You see, Greg, every woman can relate to your desire to wear a bra. At around the age you saw Penny’s bra, when our breasts start to form, we’re hoping and wishing for our first bra. We end up in a waiting game that can become very frustrating. Not every girl in the class needs a bra at the same time or age. Some girls might have to wait a couple of years for their breast buds to form. They’ll feel no different than the way you did in our scene, thinking and dreaming about getting a bra. Your mom went through that herself when she was around eleven or twelve years old. I went through that at the same age.”

I had begun crying and Dr. Nathanson handed me a tissue. “Tell me why you’re crying, Greg.”

“Because I see what you’re doing today.”

“What am I doing?”

“You’re showing me that there is an overlap between my wanting a bra and a period of time in the lives of every girl. I share the same desires that they have. No difference, except that their desire is requited naturally and mine has to be fulfilled by taking action.”

“Very good, Greg. You’re one of my smarter patients. Yes, precisely. We’ve seen today that you share an aspect of girlhood with girls everywhere. Most boys don’t have such feelings as you do. This is a clue as to who you really are. I want to emphasize that it is pointless to wonder why you’re this way. It would be the same as asking a girl why she cares so much about developing breasts, wearing a bra, and becoming a woman. That would be a silly question and it’s also silly in regard to you. We’ll continue to work on this in future weeks.”

***

I spent the next week preoccupied with the revelation that my desire to wear a bra is cooked into my psyche. It’s no different than Alice’s desire for a bra in the story I read. I’m no different than girls in desiring to wear a bra and have breasts. Unlike most but not all girls, my body is not set up to develop breasts. So I’ll always be among the girls for which bras are optional. I wondered what would happen in my next session with Dr. Nathanson.

***

Once again I was sitting naked in the chair facing Dr. Nathanson as she fetched another thin book off the shelf and handed it to me. As before, she told me to read it and describe the pictures. The title was “Alice Gets Her First Bra,” and my first reaction to the title was to feel a degree of relief that Alice was finally going to get her bra. I felt happy for her.

“There’s a picture of Alice with her mom in the bathroom. I think Alice has just taken a bath. Her mom is saying ‘My oh my, Alice, I hadn’t realized that your breast buds have sprouted. In fact you have little breasts now!’ Alice says, ‘I do? I’ve been so preoccupied with my classwork that I forgot to check.’ Her mom says, ‘We’ll go bra shopping this weekend and get you some pretty bras.’ Alice says, ‘Thanks mom. That’s so exciting. I can hardly wait to get them.’”

“The next page has Alice in the dressing room of a store. She’s wearing a bra. It has a colorful pattern in the fabric. She’s looking at herself in the mirror and her mom is standing behind her. Alice is saying, ‘I really love this bra, mom. Can we buy it?’ Mom says, ‘Yes. I agree with you that it’s a very nice bra for you. It’s an A cup so you have a little room to grow into it. In about a year, or maybe even sooner, we might have to get you new bras with bigger cups.’ Alice then says, ‘How big do you think I might end up being?’ Her mom says, ‘If you’re like me, you’ll end up with D cups. The girls in our family tend to be big breasted.’ Alice says, ‘I hope I’m big like you mom!’”

“In the next scene Alice is having dinner with her mom and dad. Her mom is saying, ‘Tell your father what we did today.’ Alice says, ‘Mom!’ and Mom says, ‘There’s nothing to be embarrassed about.’ Alice then says, ‘Mom took me shopping for my first bra today!’ Dad says, ‘She did? That’s marvelous. My little girl is becoming a woman!’ Alice says, ‘Thank you, Dad. I’m wearing my bra now!’ Dad says, ‘Boy do kids grow up so fast nowadays!’”

“On the next page Alice is in her classroom and there are a half-dozen girls grouped around her. One of them who doesn’t seem to be wearing a bra is saying, ‘You’re so lucky, Alice. You’ve gotten your first bra!’ Alice says, ‘Don’t fret, Audrey, I was frustrated about not needing a bra and then like all of a sudden, I needed one and my mom took me to buy one.’ The girl replies saying, ‘It’s okay. I’m happy for you. I know that I’ll probably need a bra soon enough. I’m not worried.’ The girl Becky from the first book who now seems to have real breasts says, ‘Welcome to the club, Alice. I’m already on to larger cup sizes. The bra I’m wearing now is a B cup!’ Alice says, ‘That’s fantastic Becky! My mom says I might need a B cup next year. I also might end up being a D cup.’ Becky says, ‘Whoa! Your family has big-busted women. In mine, we usually end up with B or maybe a C cup. Never a D!’”

“Very good, Greg,” Dr. Nathanson said. “Do you think that Alice is excited about wearing a bra to school?”

“Yes, of course. Isn’t that what the story shows?”

“Indeed. But what about a month from then, or a year or ten years later. Will Alice be excited about wearing a bra?”

I looked at Dr. Nathanson and while I had no idea what kind of bra she was wearing I was pretty sure she wasn’t excited about wearing it. That was consistent with all the women I had dated. I don’t remember them ever getting super excited about wearing their bras. “I guess over time Alice will no longer be excited about wearing a bra.”

“When you cross-dress, Greg, do you wear a bra?”

“Yes, of course. I mean, how else could I feel like I have a nice figure in my dresses?”

“Good point. So tell me. Compare when you first put on a bra vs. now. How old were you when you started?”

“Thirteen.”

“Whose bra?”

“My mom’s.”

“Yes, that’s textbook. You raided her underwear drawer?”

“Yes.”

“Tell me about your excitement.”

“Initially I was terribly excited. I remember shaking with desire and hunger to wear a bra.”

“And now?”

“I don’t feel that way anymore. It’s more like an everyday pleasure. I feel satisfied and happy wearing a bra.”

“So you see, once again there is a similarity to girls and women here. Your relationship to bras mirrors that of girls who maturate into women. But we can probe this even more. How many bras do you own?”

“About a dozen, I guess.”

“Do you feel the same way about all your bras?”

“No.”

“Tell me about that.”

“I have a number one bra, which I think is the prettiest. Then I have some other very pretty bras that are sort of equivalent. Then I have others which are pretty but not super pretty I’d have to say.”

“Do you feel differently wearing your number one bra vs. the other bras?”

“Yeah. I always feel kind of special in my number one bra. I like looking at myself wearing it.”

“The fact is Greg, that what you just said about your bras would also apply to me. I have a favorite bra, a few others that are almost as pretty, and then I have what I call my everyday bras. They’re pretty also, but not super pretty. They’re mainly white with maybe some lace but not like the very pretty bras.”

“So this is yet another way that I am really the same as women.”

“True, Greg. When you come next week, I want you to bring a panty and your favorite bra and your breast forms. You do have breast forms, don’t you?”

“Yes, of course, I do.”

“I figured.”

***

A week later when I showed up, Dr. Nathanson told me to undress in the bathroom, but come out wearing my panties and a bra with my breast forms inserted. Now sitting in the chair facing her, I felt differently than the prior week. There is something about wearing a bra and having breasts, even if they’re prostheses, that makes one feel like a woman, even if one knows that they’re not a woman.

Dr. Nathanson said, “That’s a very pretty bra, Greg. With the matching panty I think you have good taste. A good eye toward what women find appealing.”

“It’s my favorite bra,” I said.

“Now I want you to compare yourself to me. I’m also wearing my favorite bra.” I watched in awe as Dr. Nathanson unbuttoned her blouse, took it off and put it carefully on the back of a chair. “Stand up and face me, Greg.”

I got up and gaped at her beautiful chest. Her bra was pretty and sexy and filled with her large breasts. I immediately coveted it. If I could just touch it and feel it. “So what do you notice here, Greg?” Dr. Nathanson asked me.

I was in heaven. I mean, come on now. For a guy like me to have the chance to see such a perfect womanly pair of bosoms so sweetly and perfectly constrained by a pretty bra is surreal. I said, “I see that your favorite bra is very pretty. It could easily be my favorite bra.”

“More than that, Greg. Look at your own chest and then look at mine.”

I looked down at my bra that was well filled out by my breast forms and then I looked at Dr. Nathanson’s again. “I guess you and I have very similar bras and our chests look quite similar when you think about it.”

“Yes. That’s the point I’m trying to raise with you. If one had a snapshot of you in your bra and me in my bra, no one could tell which came from a genetic woman such as myself and a person like you who appears to be outwardly a man.”

“So this is yet more evidence of how I am the same as a woman.”

“Yes, Greg, good.” Dr. Nathanson put her blouse back on but she didn’t tell me to get naked. She handed me another book starring Alice. The title of this one was, “Alice Finds a Dress for the Junior High Prom.” Once again she instructed me to read it and describe the illustrations.

I said, “The first page has Alice talking with her mom. Alice now seems to have woman-sized breasts and is wearing a relatively simple dress. She’s saying, ‘Mom, I need to get a dress for the prom!’ Her mom says, ‘A boy asked you to the prom?’ Alice says, ‘Yes. Tommy asked me to go. He’s very cute. I’m very excited.’ Mom says, ‘How well do you know Tommy?’ Alice says, ‘I’ve known him for a while. He’s in some of my classes.’ Mom says, ‘Is he a good student?’ Alice says, ‘He’s very good at sports and he’s popular.’ Mom says, ‘Okay, but some boys can be tricky.’ Alice says, ‘I know, Mom. Tommy is not like that.’ Mom says, ‘This weekend we’ll go looking for a dress for you.’ Alice says, ‘Becky and Trudy also need to shop for prom dresses. Can we go with them and their moms?’ Alice’s mom says, ‘Of course we can. That should be a fun time for all of us.’”

“Now they’re in a dress shop. All around them are racks of prom dresses. I see that Alice is looking at a collection of dresses that have wide skirts and are puffed up. Becky is looking at slinky dresses and Trudy is looking at pantsuits. The three moms are talking among themselves. Trudy’s mom is saying, ‘I can’t get Trudy into a dress. I think the last dress she wore was when she was three. After that she’d go ballistic if I tried to put one on her.’ Alice’s mom is laughing and saying, ‘I’ve always had the opposite problem. I can’t get Alice to wear anything other than dresses. She throws a fit if I try to get her into jeans.’ Becky’s mom then says, ‘My Becky will wear jeans and dresses, though she doesn’t like very feminine dresses and she doesn’t like boy jeans.’”

“The three girls are now in the dressing room. Alice has just stepped into a dress and is in the act of pulling it up. We can see her bra and developed chest from the side and the bra strap running across her back. I notice that there is a crinoline lying on a chair near her. Becky is in the act of lowering a dress over her head. We can see the bottom of her bra and her panties and pantyhose. Trudy is stepping into pants and is wearing a top that is not yet buttoned and we can see that she’s wearing a very plain white bra. Once again the mothers are looking at their daughters. Alice’s mom is saying, ‘She loves puffed up full skirts. I keep waiting for her to outgrow it, but she doesn’t. She loves being a girl. Everything about it.’ Becky’s mom is saying, ‘I wish Becky had more girl in her and less woman. I think her goal is to be a man slayer! The dress she picked out is all about sophistication.’ Trudy’s mom says, ‘Well, just look at Trudy. She’s going to the prom with a boy who I think she asked out. He must be fairly submissive or I don’t think she would like him. Trudy has never liked boys having an advantage over her.’”

“On the next page the three girls are admiring themselves in the full-length mirror. Alice looks darling in her pink dress with full skirts. I suppose she’s used the crinoline. The chair that it was on is now empty. She’s saying, ‘This is the prettiest dress I’ve ever had. I hope Tommy likes it!’ Becky looks quite sharp in her dress that goes to a bit above her knees. Alice’s mother says, ‘Becky looks so grown up in that dress!’ Trudy’s pantsuit is well tailored and she seems happier than she’s been up to this point. She says, ‘This is exactly what I’ve been looking for.’”

“The next page has Tommy picking Alice up to take her to the prom. He’s taller than Alice and muscular and looks like a surfer dude. His expression seems smug. For her part, Alice is in her very pretty dress and she’s all smiles. Tommy is saying, ‘You’re very beautiful tonight, Alice.’ She responds saying, ‘Thank you, Tommy. You are very handsome!’”

“The last page is at the dance where Alice and Tommy are dancing. Her skirts are flying around and Tommy is saying, ‘I like to watch you dance, Alice.’ Near them Becky is dancing with a guy who looks like he stepped out of GQ and near them Trudy can be seen dancing with a guy in a loud checked jacket and baggy pants.”

“So what do you think this means, Greg?” Dr. Nathanson says.

“Girls don’t all think alike or have the same preferences?”

“Exactly. Alice is a very feminine girl. She seeks the approval of her date. Becky is self-assured and dates her equal. Trudy is not afraid to be herself and her date is also out there and deferential to her. Which one of these three girls is closest to you, Greg?”

I knew without hesitation that I was an Alice through and through. “Alice.”

“Which one do you think I am?”

“Probably Becky?”

“Yes, I agree with you. So even though you and I share similar preferences for lingerie, our personalities differ by quite a lot.”

“Would Trudy have lingerie like you and me?”

“Trudy probably wears lingerie for their function more than their sexiness. But she very well might own a couple of pretty bras. While different women might fit these different profiles, any one woman might have some element of each of them in her makeup.”

“I see what you’re saying.”

“So now we know that in many ways your desires and feelings run parallel to what girls feel. We also know that among girls, you’re most closely aligned with Alice, as against Becky or Trudy. Is that a fair summary of where we are now Greg?”

“Yes. It’s amazing Dr. Nathanson but I think some of the fog surrounding who I am and my desires is starting to lift.”

“I’m glad to hear it. Next on our agenda will be further exploring some aspects of the female persona that you share with Alice.”

***

For our next session, Dr. Nathanson had me once again wearing panties and a bra, but she had also told me that I could wear my favorite crinoline since that would help me anchor myself in the character of Alice. I do own several pretty crinolines and of course my pink ones are my favorites. I have a light pink one and a cotton-candy pink one. I brought the latter one with me. Sitting across from Dr. Nathanson with my fluffed up pink skirts and a bra I felt like I was her young daughter. As she had predicted, I was madly in love with her.

Dr. Nathanson handed me a book and told me to read it like usual. “I want to warn you, Greg, that unlike the other books we’ve read about Alice, this one covers some difficult emotional territory.”

I looked at her feeling a bit worried. Dressed as I was made me feel strangely vulnerable to what would be coming. I saw that the book was entitled, “Alice at the Prom.” It seemed innocuous enough. What could go wrong at a prom? I had been wondering if Alice had had a good time at the prom. Maybe she didn’t have such a good time after all. She had been so excited about her dress. I hope Tommy doesn’t disappoint her.

I said, “On the first page, Alice is dancing with Tommy. It’s obviously a slow dance and he’s holding her snugly. Alice’s thinking, ‘It’s nice how strong Tommy is. I enjoy feeling myself pressed up against him. He’s been such a gentleman tonight. I hope he’s also having a good time. I hope he asks me out again.’”

“On the next page the dance has ended and Tommy is facing Alice. He says, ‘Let’s go outside for some air.’ Alice says, ‘Oh sure, why not.’ Tommy says, ‘Yeah. We can find a bench.’ Alice says, ‘OK, Tommy.’”

“On the next page, Alice and Tommy are sitting on a bench and Tommy has his arm around her. She’s thinking, ‘This is so great. Tommy is such a cool guy and he seems to really like me. I hope he kisses me! I’ve never kissed a boy before!’ In the next picture Tommy is kissing Alice and she looks very happy. She’s thinking, ‘It’s so heavenly to kiss a boy. My heart is just beating away!’ In the next picture they’re still kissing and Tommy has his hand on the outside of her breast. Alice mumbles, ‘Tommy’ and he says, ‘You are so pretty, Alice. You’ve got such a beautiful figure!’ Alice mumbles, ‘Tommy, do you think that’s a good idea?’ Tommy says, ‘I love kissing you so much. That makes me think of how beautiful your body is and then I find myself wanting to caress you. I really do think that girls love this kind of attention. That’s what I’ve heard and experienced before.’ Alice says, ‘Okay, Tommy. I see what you’re saying. It’s so nice kissing you I can see that there’s no harm in that. I guess it’s alright if you touch me there.’ Tommy says, ‘You’re such a smart and thoughtful girl, Alice.’ His hand is now seriously feeling Alice’s breasts on the outside of her dress.”

“In the next scene they are still kissing and Tommy’s hand is now resting on the top of Alice’s skirt. She’s thinking, ‘I wonder what he’s planning to do with his hand now. Will he try and reach inside my skirts?’ Tommy says, ‘This is where a cool Alice lets her date have a bit of access inside her dress. I know that girls love to be pleasured this way. It’s pretty uncool for a boy to ignore her needs.’ Alice is thinking, ‘Do girls really like to get their panties touched?”

“The next illustration has Tommy continuing to try to work his hand through all of Alice’s puffed-up crinolines. There are many layers and Tommy seems frustrated trying to get underneath all of them. Tommy says, ‘Please help me, Alice. My hand is just lost in your skirts!’ Alice is thinking, ‘Should I help him? He just wants to touch my panties? I guess he’s right that girls like this. I don’t know. Should I let him? Kissing him is so nice. If I don’t let him, will he get mad? Will he walk away? He’s been so sweet so far. I mean he’s asking for permission isn’t he?’ Now Alice says, ‘I’ll lead you through my crinolines, you poor lost boy! Tommy says, “You’re the best, Alice!’”

“Alice has a kind of strange look on her face in the figure on the next page. Tommy’s hand seems to have found her panties. She’s thinking, ‘He felt my panties a little and then slipped his hand inside. I guess that was what he was talking about. Is it bad of me to let him touch my vagina? He would be the first boy ever to do so. I can’t tell if it feels good or not, but I guess it’s something that boys really like. It is sort of nice the way he’s holding me so snugly now and kissing me. Imagine that. One of the coolest guys in the class is so excited by me!’”

“On the next page, Tommy is using his free hand to unbuckle his belt, unbutton his pants and pull down his zipper while still kissing Alice who is unaware of what he’s doing. She’s thinking, ‘Tommy seemed to really enjoy touching my vagina. I’m not so sure what it was supposed to feel like, but it did seem kind of okay. At the least it made Tommy happy.’”

“The next picture shows Tommy kissing Alice and he has taken hold of her free hand. She’s thinking, ‘I wonder why Tommy is holding my hand.’ Tommy says to Alice, ‘I hope that felt good for you. Now it’s my turn.’ Alice says, “Your turn?’ Tommy says, ‘I’m sorry, Alice. I thought you knew all about how boys and girls play with each other. Was I wrong about you?’ Alice says, ‘I’m sorry Tommy. I’m not sure what you mean?’ Tommy says, ‘Here, let me show you.’”

“In the next image he has put her hand inside his pants. Alice is thinking, ‘Oh my God, he wants me to touch his penis with my hand! That’s what he meant by it being my turn.’ Tommy laughs and says, ‘It won’t bite, though I must admit that mine’s kind of big as far as they go. I don’t want to brag, but girls get kind of amazed by it.’ Alice thinks, ‘His other girlfriends have done this? That’s what he says. Can I believe that? Girls just touch him there? This doesn’t feel right to me. I wish Becky was here to tell me what to do. I don’t want to get Tommy frustrated with me. He’ll think I’m not worthy of being his girlfriend. I so love kissing him. But I guess boys are different than girls. He seems to have gotten very sexual from all that kissing. I guess that is just the way that boys are. I don’t know. I don’t want to disappoint Tommy.’”

“In the next picture, they are still kissing. Tommy has his arm over Alice’s shoulders and she has her hand inside Tommy’s pants. Alice looks scared and Tommy is smiling. Tommy is saying, ‘Good Alice. Just slide your hand along my dick. It feels so good.’ Alice says, ‘Are you sure that it is right for me to be doing this?’ Tommy says, ‘Of course, Alice. All the girls do this. They really enjoy holding a nice cock. Especially one as big as mine. It feels so incredibly good.’ Alice says, ‘Are those girls my age, Tommy. Maybe this is for older girls?’ Tommy says, ‘If it’s bothering you so much, then you should probably stop.’ Alice rushes to say, ‘I’m sorry Tommy. I wasn’t saying that I should stop. I want you to feel good.’ Tommy says, ‘Thank you, Alice. I knew I wasn’t wrong about you.’”

“On the next page Alice has a serious expression and she’s concentrating hard on giving Tommy a hand job. He’s smiling and looking up at the stars. He says, ‘That’s great Alice. You’re doing a really good job.’”

“In the next scene, Tommy’s hand is unzipping Alice’s dress. He’s saying, ‘Girls usually let me feel their boobs while they’re rubbing on my dick.’ Alice says, ‘But Tommy isn’t this enough what I’m doing?’ Tommy says, ‘I touched them before.’ Alice says, ‘Is that all you’re going to want to do?’ Tommy says, ‘Sure, Alice. I won’t ask for anything that you don’t want to do.’”

“In the next scene the top of Alice’s dress is down and Tommy has his hand inside her bra while she’s still rubbing on his dick. Alice looks miserable, like she might cry. Tommy says, ‘This is so good. You’re the best, Alice. I love your tits. I love how your hand slides along my cock. How are you feeling, Alice?’ Alice says, ‘Okay, Tommy.’ Tommy says, ‘I knew that asking you to the prom was a great idea. I’ve had my eye on you for some time now.’ Alice says, ‘You have?’ Tommy says, ‘Definitely, Alice. You’re one of the prettiest girls in class.’ Alice says, ‘Thank you, Tommy.’ Tommy says, ‘Now there’s just one more thing and then we can go back in and dance some more if you like.’ Worried, Alice says, ‘What’s that, Tommy.’ Tommy says, ‘Do you really care about me, Alice?’ Alice says, ‘Of course, Tommy.’ Tommy says, ‘Then it would be perfect if you finish me off with a blow job.’ Alice says, ‘Blow job? What is a blow job.’ Tommy laughs, ‘You don’t know what a blow job is? It’s where you use your mouth to suck on my dick.’”

“In the next scene Tommy can’t see Alice’s face to know that she’s crying. Tommy says, ‘I don’t let just any girl give me a blow job. Only girls that are really pretty and I know really want to make me feel good.’ Alice says through her tears in a pleading voice, ‘Tommy, please! Do I have to?’’ Tommy says, ‘Of course I’m not forcing you to do anything against your will, Alice. I must admit that I’d be surprised if you didn’t really want to do this. I really believed that you and I fit together really well. I’d hate to have to nip this in the bud, just when it’s starting. I also hate to say it, but you might not be aware that if we stop now I’ll get some pretty bad blue balls.’ After a minute, Alice says, ‘What are blue balls?’ Tommy says, ‘A boy gets blue balls when a girl gets him all excited and then doesn’t finish him off.’ Alice says, ‘Finish him off?’ Tommy says, ‘You know, cums. So what’s it going to be Alice?’ Alice says, ‘What do I have to do?’ Tommy says, ‘Get on your knees in front of me while I whip it out.’”

“The next page has Alice on her knees in front of Tommy. It looks like she has his dick in her mouth. Tommy says, ‘You have to do more than rest it in your mouth. Move your head in and out so my cock slides over your tongue and your mouth and throat. Get a rhythm going, Alice. In and out. In and out. That’s better. Keep it moist. Try to get more of it into your mouth. I know it’s a very big cock, but girls really like big cocks stuffed down their throats. Really try to get more in your mouth. You’re doing pretty good for a novice. You’ll get better the more men you give blow jobs to. Eventually I’ll bet that you’ll become an expert.’”

“In the next figure Tommy doesn’t look too happy and Alice’s face is contorted in abject misery. She says, ‘I just don’t know how to do it the way you want!’ Tommy says, ‘I’m sorry Alice, but you’re frustrating me. I’m going to have to take over.’ Alice says, ‘I’m sorry, Tommy. I tried as hard as I could to do it right. You’re not mad at me are you?’ He says, ‘I guess I thought that you were a different kind of girl than you are.’ In the next picture, Tommy is standing up in front of Alice who is on her knees. He’s holding his dick in front of Alice’s open mouth. Tommy says, ‘Good, Alice. Keep your mouth open.’ Alice is crying. In the next picture, Tommy is zipping up his pants, and Alice is still kneeling on the ground. She has strings of cum decorating her face. Tommy says, ‘Well I guess that was alright. In the future if you learn how to give a good blow job, I can cum directly into your mouth and then you can swallow all of it. You should clean yourself off before you go back to the dance.’ In the last scene Alice is by herself still kneeling in front of the bench.’”

“In the next picture, Alice, Becky and Trudy are in the restroom where Alice has washed her face and is drying it. Becky says, ‘Tell us what happened with Tommy.’ Alice says. ‘We were kissing so perfectly, I was loving every minute of it and the next thing I knew he was feeling my breasts. Then he wanted to put his hand on my vagina. Then I had to hold his penis and then I had to suck on his penis.’ Trudy says, ‘You had to? He forced you?’ Alice says, ‘He told me I could not do it if I didn’t want to. But if I didn’t then he wouldn’t think that I was cool and he kept telling me that all the other girls did these things. Do they?’ Becky says, ‘Alice, you’re so innocent and naïve. Boys always try to get us to do those things. Most girls just say no if they don’t want to do them. If a boy won’t see you because you say no, then he’s not worth seeing. The good ones respect our wishes. Come here, let us hug you and make you feel better.’ Alice, Becky, and Trudy hugged for a minute. While they hugged, Alice thought about what Becky had said. It seemed so simple now, but it had been so complicated while Tommy was with her. She would never make the same mistake twice.’”

“That’s enough, Greg, I can see that you were upset about the way Tommy took advantage of Alice. We all wished that she did not make the mistakes that she did. So what is the essence of what is going on here?”

“I guess Alice was caught in Tommy’s world. His framework. She doesn’t seem to be able to act on her own beliefs.”

“Very good, Greg. What’s happened to Alice, would never have happened to Becky or to Trudy. Alice is so unsure of herself that she accepts Tommy’s instructions even though she has a sense that they’re wrong and that they make her feel so miserable that she cries.”

“Are you saying that I’m like Alice?”

“That’s for you to think about, Greg. Our next session should help you see these aspects of yourself even more clearly. Next week we’re going to act out this story. I’m going to have a guy play the role of Tommy. You’ll be Alice and I’ll have a small part as Becky. I’ll have a replica of Alice’s dress for you to wear and anything else we need. So be prepared for a potentially quite upsetting hour, but trust me that it’s necessary to get the breakthrough I’m looking for with you.”

***

It would be an understatement to say that I was freaked out by Dr. Nathanson’s description of what we would be doing next week. She seemed to be intending for me to act out the role of a girl in real life. Tommy would be a real dude. Would Tommy be kissing me? Would I be engaged with his private parts? Would Dr. Nathanson expect me to touch his penis and lick it? It was bad enough reading about how Tommy took advantage of Alice let alone actually living the same experience!

I thought about how Alice’s treatment by Tommy had an analogy in my own life. I could definitely see that I shared with Alice a fear of asserting myself. That’s what the FedEx guy had seen right away. Perhaps Dr. Nathanson was using the Alice story to drive this weakness of mine to its furthest consequence. A situation where for my own good I should learn to resist pressure like that from Tommy and not kowtow to his control. Clearly anyone reading the story was rooting for Alice to assert herself. To believe in her own instincts about what was right and wrong for herself.

***

The dress that Dr. Nathanson had waiting for me at my next session was a dream come true. In every detail it was identical to Alice’s dress. Dr. Nathanson helped me on with it and zipped me up. Having a beautiful woman dress me as a girl caused a multitude of contradictory passions to run crazy through my brain. I simultaneously was thrilled at being treated as a girl, while some degree of male lust soaked in every detail of Dr. Nathanson’s body. After the dress was on Dr. Nathanson had crinolines for me to wear that puffed out my skirts. She also had stockings and a garter belt that were what Alice would be wearing. She had me wear the identical shoes as Alice and she set about making up my face and fixing my hair to match Alice. When she was done, I felt like I had just stepped out of the book into the real world. I said to Dr. Nathanson, “You’ve made me so pretty! I know you’re a real woman and you might not see me as one, but I tell you I feel so much like a girl it seems real to me. I am Alice. I feel like I must be Alice.”

“I’m glad you feel that way. That will help you get the most from this exercise. Allow yourself to fully feel that you’re Alice. Be her.” In one corner of the room Dr. Nathanson had placed a teak bench and she pointed to it and said, “There’s the bench where you and Tommy will sit. I’ll dim the lights so that it fits in with your sitting outside in a starlit night.” She lowered the lights until it was quite dark and then she hit a switch and the ceiling was lit up by faint stars so that after one’s eyes adjusted it was possible to see vague outlines of the objects in the room. Music came on and a guy came out of nowhere and took me in his arms and I found myself dancing with him. He held me in the girls position with my right arm extended and immediately took control, leading me around so that I had to follow his movements. The guy left no doubt that I was the girl and he was the boy. He was taller than me and I could sort of make out his shadowy face in the dark and the fact that he was wearing a suit. I sensed great strength in the hand that held mine and in his arm on my back.

Tommy said, “Isn’t this dreamy, Alice?”

“Yeah.”

“Have I told you how pretty you are in your dress?”

“No.”

“Well, I think you’re the prettiest girl here.”

“Thank you, Tommy.” As we danced I got more and more into the drama we were re-enacting. I was a girl in a pretty prom dress dancing with one of the hottest boys in the school. Some of the other girls were probably jealous of me being with Tommy.

The music ended and Tommy lingered holding me. He enveloped me in both of his arms and I felt his muscular frame pressing against me. “I like how you feel, Alice.”

“I like you too, Tommy. You’re very strong, aren’t you?”

“I can bench press two hundred pounds.”

“Wow,” I said, “you’re a real muscleman.”

Another slow dance came on and this time Tommy held me close the whole dance with his arms wrapped around me. My skirts were pressed up against him and my partially bare shoulders were captured by his arms and broad chest. I was enjoying myself as the girl, as Alice. It was nice knowing that this strong man was creating a space for me to dance in. I found myself drifting off in a wonderful daydream where I had been a girl hoping for my first bra, then maturing into a woman where men desired me, and now being the woman that a real man held in his firm arms. I looked at Tommy through the eyes of a girl and woman. I like how he made me feel special. When the dance ended, Tommy said, “Let’s go outside for some air. We can find a bench to sit on.”

“Sure, Tommy, that sounds like a good idea,” I said.

I sat down on the bench in the darkened room next to Tommy and looked up at the stars. He put his arm across my shoulder and squeezed me a little. This was definitely cozy. I could see that his greater size and strength contributed to a feeling that I was being held within his domain. While I was thinking these thoughts, Tommy leaned in and kissed me on the lips. He gently rested his free hand on my jaw and then my neck as he kissed me forcefully. While somewhere in my brain I had the fleeting thought that I was Greg, it was quickly drowned out by the more immediate and certain belief that I was a girl named Alice that was enjoying this long sexy kiss with Tommy. As I kissed him I reveled in my awareness of the dress and the cloud of crinolines surrounding me, my bra and stockings and was quite aware of how I had significant breasts. Tommy’s unflinching masculine presence had the effect of propelling me deeper and deeper into my role of Alice. Tommy’s kiss elicited a desire in me to be a receptacle for his tongue, a warm and loving place which he could hold and feel my body bending to his dominance. While he kissed me so passionately and totally, I wondered if this derived from his happiness at being with a pretty girl like me at the prom? I told myself to relax and make no attempt to interrupt what he was doing. He could kiss me as long as he liked. I would be there for him.

I took an inventory of the sexual response of my body to Tommy’s kiss. I realized that my nipples within my breast forms and bra were tingling and perhaps some blood was running down toward my vagina? Penis? What exactly did I have between my legs if I was Alice? Tommy moved his arm from my chin to rest gently on my breast. “Oh, Tommy!” I mumbled while Tommy was kissing me. “Do you think that is a good idea?”

Tommy said, “I’m sorry Alice. I love kissing you so much that I got swept up in realizing how beautiful you are. Your figure is so tantalizing I could not resist caressing it. Girls usually like this kind of attention from boys.”

I said, “I see. Well I guess it’s okay if you touch me there Tommy.”

“Thank you, Alice,” Tommy said and then began feeling my breasts going back and forth from one to the other.

After a while I felt Tommy rest his hand on top of my skirt. He broke off our kiss and said, “I wonder what’s inside that pretty dress of yours?”

“I’m wearing a favorite pink crinoline of mine.”

“And inside that?”

“Oh, Tommy!”

“Can I touch your panties?”

“I don’t know, Tommy. That seems like a big step.”

“Girls like that attention from boys, besides the fact that it’s a nice intimate way I can pleasure someone I care a lot about.”

“You care about me, Tommy?”

Tommy laughed and said, “Are you kidding, Alice. I’m crazy about you.”

“And I’m crazy about you, Tommy. I guess it’s okay if you put your hand in my skirt.”

“You won’t regret it, Alice.”

Tommy worked his hand into my skirts and seemed to get stuck unable to get it past the different layers. I said to Tommy, “I’ll lead your hand past my skirt and crinoline to my panties.” Tommy put his hand in mine and I brought it up underneath the layers of skirts to a point on the stocking of my upper thigh. Tommy took over from there and his hand inched up to the top of my stocking and then across the bare flesh between my panty and stocking. I said, “No boy has ever been where you are now.”

“Really, Alice? I’m surprised. A pretty girl like you?”

I felt Tommy’s hand touching the thigh band of my panties and then it slipped inside them to a point just to the side of my penis. “Oh my God, Tommy. Your hand is inside my panties! Are you trying to touch my vagina?”

“I’m sorry, Alice,” Tommy said. “You’re so sweet I just want to make you feel good. Is that okay?”

“I think I would be a bad person to let you touch my vagina.”

“Why would you think that? Most girls would understand why you might like to have a boy touch your vagina.”

“No boy has ever done it before to me. I guess I’m a little scared about it.”

“Just relax Alice. I’ll kiss you some more, and while I’m doing that I’ll let my hand gently feel around your vagina. Sort of saying hello to a new friend.”

“Okay, Tommy. I like the way you hold me while you’re kissing me. It’s snug and I like to feel your strong muscles. I guess it’s time I let a boy touch me there and you’re such a nice boy.”

“I’m also super cool.”

“That too, Mr. Modesty."

Tommy moved his hand around inside my panties. His fingers seemed to brush up against my penis and balls, but he did not hold onto them. I guessed that it was important for our drama that I really be a girl. I was certainly feeling that I was a girl, except for this one masculine part of my anatomy.

After a few minutes Tommy broke off the kiss which gave me a chance to breathe. I wondered what he was going to want to do next. I heard the sound of a belt buckle and I realized that he was more than likely preparing himself for me to put my hand in his boxers. On cue, Tommy took my hand and brought it to touch his warm belly. “What are you doing Tommy?”

“Alice, I’m so turned on. It’s your turn to touch me where I touched you. Can you do that?”

“What do you mean Tommy? Touch your penis? Is that what you want?”

“I’m sorry Alice, but it’s what any girl would do for her boyfriend.”

Tommy moved my hand down into his boxers until I felt his pubic hair. I tried pulling my hand back out and he held it so it wouldn’t move. “Tommy, I don’t think you know your own strength. I’m struggling to move my hand but you’re too strong for me to move it. Can you let my hand go?”

“I’m sorry, Alice. I wasn’t aware of what I was doing. It’s just that a man can get some pretty strong feelings when he’s been kissing and touching a beautiful girl like you.”

“I understand, Tommy, but I’m not so sure that I’m ready for this.”

“I’m afraid to say that there’s a word for girls like you, Alice.”

“What’s that?” I said with alarm.

“Cockteaser. You’ve gotten me all wound up. If we don’t go to the next step then I’ll develop a bad case of blue balls. Then I’ll have to go and relieve the pressure somewhere.”

Okay, Okay, Tommy, I don’t want you to be mad at me. I’ll touch you there,” I said.

“Now you sound like I’m forcing you,” Tommy said.

“No. I didn’t mean it that way Tommy. Go ahead and show me what to do next.” I decided to be completely docile. It was the easiest path. Let him guide me and do with my hand what he wanted.

“You’re the best, Alice.”

Tommy resumed pushing my now compliant hand down inside his boxers until my fingers felt his pubic hair. He said to me softly, “Hold onto my cock.” My fingers encircled his organ. I had never before touched a boy’s penis. “Slide your hand up and back,” Tommy said. “That will make me feel good.” I moved my hand up and down along his dick and felt his organ surge up in size. As I kept at it, his penis shifted from a kind of flexible almost floppy state, to one of amazing rigidity like a wooden pole. I’m not a great expert on penis sizes but I had the sense that his was no ordinary dick. The length was surprising to me. My hand had to run a long way on the shaft from base to top. The girth was unusually large and my hand encircled it without much room to spare. “See, Alice, it’s not hard to do. You’re doing very nicely now. You just keep up like that.”

“I like to give you pleasure, Tommy,” I said. That seemed like the one positive aspect of what was happening.

“That’s nice. If you don’t mind, every so often hold my balls.”

“Sure, okay.”

When my hand next arrived at the base of his penis I felt around until I located his balls and then held on to them. “Hello!!” Tommy said. “Oh, Alice, that’s so good.”

“Men like their balls touched?”

“You bet,” Tommy said between clenched teeth.

“These are the first balls I’ve ever touched. I’m not totally sure I should be doing this. Tell me you really like me Tommy.”

“Alice you know I really like you.”

“Am I your girlfriend now?”

“Yes, if you want to be.”

“I think I do, Tommy.” I’m not completely sure why I said that. Probably because I was afraid of Tommy and thought that this might make him be kinder to me.

After a minute I again encircled his penis with my hand and resumed sliding it up and down. I was resting comfortably with Tommy’s arm across my back and my hand working on his penis. I felt Tommy begin to unzip the top of my dress. He said, “Can I pull your dress down enough so that I can feel your breasts while you rub on me?”

“I don’t know, Tommy. This seems like it’s getting more and more intense.”

“I’m sorry, Alice. This is sort of what sex is all about when two people feel strongly for each other. Besides, girls usually like to have their boobs felt up while they’re doing this.”

“That’s really true?”

“Of course, Alice.”

“Well, okay Tommy. If this is what makes you happy.”

“It does.”

Tommy got my dress down below my boobs and put his hand inside my bra and felt my breast forms while I gave him a hand job. I sensed him getting more and more excited. His size and the power of his body were intimidating. I could feel rippling muscles in his thighs and arms that seemed hopelessly more formidable than my own. There was something about a fully aroused man that was scary. It was like the eruption of a volcano that one could not control.

At some point in my continuing hand job with Tommy’s dick hard and straight, Tommy said to me, “This is the last thing I’ll ask of you. Big girls will want to give me a blow job at this point. Can you?”

“Blow job? You mean suck on your penis? Tommy, that’s what you want me to do?”

I felt an urge to cry and I said, “Do you really see me as that kind of girl?”

“What kind?”

“A girl who would give you a blow job just like that. On our first date?”

“Alice, Alice, Alice. I have only the highest respect for you. It’s just the perfect way to finish me off. I think it’s the logical and natural conclusion of this perfect little rendezvous on the bench. I think the world of you, Alice. I would never willingly do anything to besmirch you. Seriously.”

“I think you should love me before I do something like a blow job.”

“But I do essentially love you. During this evening you’ve shown me how incredible you are and any man would say they love you.”

“You truly love me, Tommy. You’re not just saying that, are you?”

“Of course not, Alice.”

“You won’t look at me as being a bad girl?”

“Don’t be ridiculous.”

“Is this going to be the last thing you ask of me?”

“Yes, of course. This is the end of a marvelous time together outside.”

“Tell me what I have to do.”

“First thing is get on your knees in front of me.”

I got on the ground in front of Tommy. In the dark I could make out the form of his penis. I put my mouth over it and began sucking on it. As I tried to accommodate the large organ in my mouth Tommy said, “Alice, can you get a rhythm going? Also, can you try and fit more of it inside your mouth?”

“I’m trying, Tommy. I’ve never done this before. It’s also very big, I’m struggling to get more in my mouth. It makes it hard to breathe if it goes in too far. It’s also making me gag.”

“I understand. Just try, that’s all.”

I tried to establish some sort of rhythm with my sucking but it wasn’t easy. At a certain point Tommy perhaps got a bit frustrated since he put his hand on the back of my head to hold it steady and then began rapidly forcing his hips toward me sending his cock deeper into my mouth. This seemed to perk up his excitement level to a point that was frightening. He seemed almost possessed to me. His penis which had seemed like it might be softening became rigid again and I set my mind on relaxing as best I could while Tommy used my mouth the way he wanted to. I hoped it would soon be over. Tommy was at heart a selfish and mean boy. I was now at his mercy by the way he tricked and deceived me every step of the way since we had sat down on the bench. I was lucky that he didn’t intend to have sex with me this night. I don’t know how I would have been able to stop him. Nothing that he wanted me to do had I been able to stop. He had a way of pretty much twisting me around anyway he wanted.”

We went on the way we were for some time. My knees were hurting a bit and I was worried that the way I was kneeling might cause a run in my stockings. But I didn’t fight Tommy. He was definitely enjoying himself. He began grunting and I realized that he must be close to cumming. I wondered if he was planning to cum into my mouth directly, which would have been an entirely new and strange experience for me. Instead he suddenly pulled his cock out of my mouth and said, “Keep your mouth open, Alice.”

So this was how he was going to finish. My mouth was to be a target for his cum. I guess he figured that girls like getting a mouthful of cum. Maybe the ones in the past he’s had sex with liked this, but for me I had no reference point. I had no idea whether this was something I would like or even supposed to like. Anyway, I was worried about causing a scene with Tommy if I questioned him so I knelt in front of him watching him stroke his cock inches from my face fully resigned to whatever would happen next. I didn’t have to wait long as Tommy made a much louder grunting sound and his hot, wet, semen squirted first into my mouth and lips and then on my forehead, my hair, my chin, and my nose in perhaps six more sizable doses. It was a formidable display of manly orgasm. I supposed that his large balls must have contained a fair amount of seminal fluid.

When the last drop was safely deposited on my face, Tommy stood up and zipped up his pants and buckled his belt. “You need to clean yourself up before you go back into the dance.”

With that Tommy left me where I was kneeling. Not so much as a thankyou or an offer to get me a Kleenex from my purse. No indication that we’d finish our evening together. All he could do was give me free advice about cleaning his cum off my face, like I wouldn’t remember it was there. Before Tommy took five steps away from me I doubled over crying. I heard him stop and say, “That wasn’t too bad, Alice. I think you need a little practice.” I cried harder and then he was gone.

A short while later I sensed that someone was next to me. “Alice? Is that you. It’s Becky. What are you doing on the ground?” Becky pulled on me gently helping me get up and I sat down on the bench. I realized that Becky was being played by Dr. Nathanson. While I wept she held me. She apparently had a tissue and wiped the cum off my face. I hadn’t known what to do with the cum that landed in my mouth but I spit it out into a tissue. “What happened to you, Alice? Did Tommy do this to you?”

“Yes. I don’t know what happened, Becky. We started out kissing. I loved it so much and then he kept on wanting me to do more and more things. He felt my breasts and vagina. Then he had me feel his penis and then start to rub it. Then he had me suck on it and then he masturbated into my face. I can’t believe it. And he just left never thanking me or saying he cares about me.”

“What a prick! How are you?”

“I’m shaking a little,” I said. “That was so emotional.”

“Tommy used you. He took an innocent girl, used flattery and a bunch of lies to get you to agree to do many things that you’re not ready to do with him. Then, he dumps you the moment he gets his sexual release.”

“It makes me mad, but I’m not only mad at Tommy I’m also mad at myself.”

“Where does the anger toward yourself come from?”

“From letting Tommy do these things to me. I should have stopped him.”

“Why didn’t you?”

“Because I thought I was supposed to be the person that Tommy wanted me to be.”

“Why did you think you were supposed to be the person Tommy wanted you to be?”

“I guess because I didn’t really know who I was.”

“Now, do you know who you are?”

“I think so. I’m a girl who would not have done any of those things that Tommy wanted me to do that I didn’t want to do.”

“If you had been yourself with Tommy, he would never have gotten beyond kissing you?”

“I think so.”

“This is great Greg. Let’s step away from Alice now. Remember that when the FedEx guy showed up, you wanted to take off your dress and look like a boy. We’ve seen that your true nature is not that of a boy. It’s a girl like Alice, so if it hadn’t been for the FedEx guy telling you to stop, you would have forced yourself to pretend that you were someone you’re not in order to please what you imagined that the FedEx guy expected of you. With Tommy you once again tried to become a different you. This other person was a girl who did what Tommy wanted her to do. The end result was it made you feel cheap and miserable. There is a lesson here, Greg. What is it?”

“I have to know who I am and then behave in a way that is consistent with that. Being someone I’m not in order to please other people, whether they want it or not, is a recipe for being miserable.”

“Of course, people can change, and there are lots of good reasons why people should change. But not everything in a person can change. The things that fundamentally decide who you are cannot change. You could develop a love of peas after first hating them. You cannot lose your desire to wear dresses. You cannot lose the desire to pretend that you’re a girl. These things are forged within you and define who you are. They’re indelible and unchangeable. Recognizing these truths about yourself will liberate you from the control of others.

“I can’t thank you enough, Dr. Nathanson. I feel like a new man, or should I say, girl. I feel like I can now start the process of coming out into the world as myself. It might not happen overnight, but I think I see the path forward.”

“I am sure you will succeed, Greg.”

I arranged to see Dr. Nathanson a few more times to solidify the progress I had made. She said that I could keep the outfit she had provided me with for which I spontaneously gave her a hug. I was so reluctant to take off the dress, that I asked Dr. Nathanson if I could go home dressed this way. She said, “Of course you can. If there is anything that we’re trying to teach here, it’s that you can be yourself!”

Excited, scared, titillated, I left Dr. Nathanson’s office in my pretty dress and walked to my car parked a block away from her building. I was sure that everyone in the world was looking at me, but I didn’t care. I got in my car and drove home. When I got there, I entered the house and lay down on my bed and basked in pride in being myself for the first time.

***

A couple of months after last seeing Dr. Nathanson, I was in my back porch when a woman UPS delivery person walked up the back steps with a package for me. She was wearing the standard uniform with long pants and I was wearing one of my everyday sheath dresses. Without hesitation I greeted her and took the package from her. She looked at me with some surprise and I said, “Nice day.”

“Indeed it is,” she said. “That’s a very pretty dress you have on.”

“That’s so kind of you to say,” I said. “It’s one of my favorites.”

“It’s none of my business, but I should say that it is refreshing to meet someone who is so comfortable being themselves.”

“Thank you for saying that.”

I continued to smile at the woman and she said, “You know, I’ve never done this before, but could I get your phone number?”

“Phone number?”

“I’d like to ask you out for coffee sometime, if you don’t object.”

“Coffee? I guess that would be okay.”

“I’ve always had a thing for men who wear dresses. I find you very cute!”

“You’re making me blush. What’s your name?”

“Tammy.”

“Very interesting, Tammy. Please do give me a call!”

The End