Never Going Back Again

I was doing great in my classes and I was able to develop relationships with people that weren't based on my inadequacies. I was still painfully aware of these inadequacies, of course. But I was relieved to know that I was the only one in my present circle of acquaintances who was aware of them. I started to relax and even began to trust people. I ultimately came to trust one person, Amy, enough to reveal myself to her.

Amy was wonderful. She was attractive, not like a model, but nice looking. And we really hit it off. We liked many of the same things and we both came to like the things the other introduced us to. I fell in love with her and, remarkably, I think she loved me, too.

As the relationship got more intimate, I decided I was going to talk with her before we took off our clothes with each other. I knew she wouldn't be cruel but if she'd made a good faith attempt to not seem disappointed just out of her sense of decency or her affection for me, it would have been more than I could bear. So, near the end of a nice dinner at a quiet restaurant where we had privacy, I raised the topic—explicitly and with the warning that if she wanted to end our relationship, or change it to a purely platonic one, I wouldn't think any the worse of her.

I think my set-up must have frightened her because when I finally spilled out my deep secret—that I was incredibly small in the manhood department—I could see genuine relief on Amy's face. She didn't care about that at all. In fact, she thought I was just being silly. She reminded me that she was not all that busty, but I didn't think the analogy worked. She has a very good figure and there was certainly nothing about her that limited her ability to function as a woman.

But, in any case, Amy didn't care. And that was an incredible relief for me. In fact, I was surprised by how relieved I felt. I guess I'd been trying to accustom myself to the thought that she would want to dump me and, so, I was rationalizing about how that wouldn't be so bad. I was telling myself that everything else was going well for me now so I could handle it if she didn't want to keep seeing me. It was only when I realized that this really didn't matter to Amy that I could admit to myself how awful it would have been if she'd ended things and how wonderful it was that she didn't.

Amy and I developed a relationship that is, for the most part, too private to share with others. But, since some of it is relevant to the rest of my story, I'm going to share a bit of it.

We found lots of wonderful ways to make each other feel terrific. I'll bet I know more about how to please a woman than almost any other guy. And Amy never made me feel as if I wasn't enough for her just because my penis was so tiny.

Eventually, I became so secure in the relationship that my feelings of inadequacy receded almost to unconsciousness. Once that happened, I actually went out and bought a big, realistic strap-on dildo to fuck Amy with. I never could have done that when I still felt insecure in our relationship or worried about her feelings about the size of my equipment. It would have just underscored my inadequacy.

You might wonder what I got out of fucking Amy with a dildo. It's true that I didn't feel her mouth or cunt on my cock. But it felt great to slam into Amy very hard. When we're really fucking, I have to be very careful not to pull back too far or I'll slip out. But with this dildo, which was about 8 inches long, I could really draw back and slam into her.

And Amy loved it. She loved the other things we did together, too. It's not like this replaced our other activities. But it was a nice new addition.

We played around with light bondage. Nothing serious. One of us would tie the other up and take complete charge. It was never about causing pain—thought a little discomfort from an ice cube or some such thing was okay. It was always about controlling how and when we gave the other person pleasure. And it could intensify that pleasure considerably.

Once, when Amy had me tied up, she turned the tables on me. She blindfolded me and tied my hands to the headboard. She'd done that a lot before. But what she did next was new. She tied my feet back over my head, stretching one to each corner of the headboard. This rocked my pelvis up, exposing my asshole completely.

I guess I knew what was coming but I still twitched when I felt her fingers gently probing my sphincter. Her hands were slippery with some sort of lubricant and she was working it deep into my anus. And then there was a long pause in the action while I was just left there, blindfolded, imagining what was going to happen next.

What happened next was that Amy climbed on top of me and I felt something very large pressing against my asshole. Obviously, she'd strapped on the dildo and was planning to test whether what was good for the goose was good for the gander.

As she increased the pressure against my ass, she began to talk to me in rough, degrading ways. It was all playful, of course, but she was talking to me in a way that she hadn't before. She told me how much I was going to love taking her cock, how a little slut like me loved to get fucked hard by a huge cock and milk it of its creamy load.

All of this was making me very hot and I could feel my dick standing up, rigid as can be. Amy noticed, too, of course. She started telling me what a slut I was to have my clitoris get hard when I was thinking about taking a hard cock in my cunt. These words sent me to a new level. With the blindfold on, I was free to visualize anything I wanted and Amy's words were really making me think about being a woman who was being forced to take a huge cock in her cunt. I didn't think I could get any harder than I already was, but I did. My penis, or I guess I should say 'my clitoris', was almost painfully hard at this point.

And then my ass yielded to the insistant pressure. Very slowly, Amy pressed her cock into my cunt. It felt wonderful! It wasn't the first time I'd been fucked in the ass, of course. Jerry had had the pleasure of deflowering me and the girls at the slumber party had reamed me with a strap-on dildo. But I'd never been fucked like this.

Amy had ceased all of her harsh and demeaning talk. It had served its purpose. I was incredible hot and eager for her to fuck me. But with the sort of abrupt emotional change-up that kept our lovemaking exciting, Amy had switched to fucking me gently and lovingly. Well, maybe 'gently' isn't the right word. She was still being forceful and domineering, but now she was fucking me like a man fucks the woman he loves when he's consumed with passion.

I think Amy decided that the ropes and blindfold weren't in keeping with the changed mood. Keeping the dildo deep inside of me, she gently pulled my blindfold off. She looked into my eyes deeply and the gentle smile that graced her lips made my heart melt. I watched her lovingly as she untied my feet. It was a relief to be allowed to lower my legs. I wrapped them around her thighs to keep her pressed deeply into me.

She didn't untie my arms. I guess she wanted to maintain that amount of control. I liked that. She was still in complete control; I was still helpless and at her mercy. That made the sweetness of her lovemaking a free gift to me. She could have taken me any way she wanted to. And the way she wanted to was lovingly.

Amy's eyes penetrated my soul as her dildo penetrated my ass. Even though Amy is a beautiful woman in my eyes and, with my blindfold off, I couldn't imagine her as a man, I did go back to imagining that I was a girl being fucked for the first time by a huge cock. It was all filled with conflict—not the "I want it but I don't want it" kind of conflict. I wanted it completely. It was just a strange juxtaposition of looking at the face of my beautiful girlfriend while being fucked in my cunt by a man's cock that she was somehow controlling.

Amy fucked me for a long time. She ended it by getting up on her knees between my thighs so that she could stroke my penis while she finished fucking me. It didn't take very much of that to make me shoot my load harder than I'd ever done before. My semen was still mostly a clear, thin liquid, but it didn't just dribble out. It spurted out on my chest, each thrust of Amy's cock provoking a new eruption.

When my penis had finished spurting, Amy gathered some of the cum on her fingers and fed it to me. I sucked her fingers with relish. I felt like a girl who was sucking her lover's cock after he'd fucked her. I was in heaven!

Amy and I recreated that scene—and many variations of it—frequently over the next months. It wasn't our only way of making love. I still played the guy frequently. But I became very comfortable, too, with the role of the girl, being fucked roughly or gently, but always passionately, by a guy with a big, hard cock. Amy didn't get an orgasm from fucking me this way, of course, but she enjoyed the experience for the pleasure it gave her, too—not just for the pleasure she was able to give me.

As things progressed and I continued to be comfortable with this, Amy began adding props to the scene. She'd dress me in a bra and panties, or in some sexy lingerie, before fucking me. Eventually, she convinced me to let her shave off what little body hair I had. Then she would dress me completely as a woman: not just a bra and panties, but stockings and a garter belt, a sexy dress or skirt and blouse, and high heels. Because we were the same size, I could wear her things. But to make the illusion complete, she bought me a wig. And then, a few weeks later, some marvelously realistic artificial breasts that could be glued to my smooth chest to give me a great figure. When we could take the time for her to dress me completely, do my make-up, put on my breasts, and arrange my wig, I turned out to be a very attractive woman. Indeed, we were both sure that with a little practice on the heels and my mannerisms and speech, I could easily pass public scrutiny. Amy gave me my femme name, 'Stephanie'. And when I was all dressed up, I really felt more like a Stephanie than like Stephen.

I was very much in love with Amy. And she with me. The gender bending we did seemed only to increase our passion and trust. We played like otters.

Life was good. We both graduated and got good jobs. We talked about getting married, but decided to wait a bit. Neither of us particularly cared about that.

Then I got an invitation to my high school's five-year reunion. I was about to pitch it but I decided to show it to Amy and talk about how ridiculous it was to think that I would go. After all, I'd sworn that I would never go back to my home town again.

Amy started to think differently about it, though. I'm not sure why, but she seemed set on the idea of our going back to the reunion. And, as time went on, this became more of a fixation. I'd do practically anything that Amy really wanted me to do, of course. So, in the end it was settled. We were going.

But the reunion wasn't for nearly three months. And Amy had plans for some big changes during that time—changes to me. These changes were pretty troubling to me when Amy first proposed them. But I agreed to go along.

The plan was for me to go en femme—totally. Well, almost totally. Amy had been doing her research; I had to give her that. She'd found a doctor who would, under the right conditions, prescribe for me female hormones like those that transsexuals take. The right conditions were that I swear that I feel like a woman, trapped in a man's body, and that I pay him $1,000 in cash. For another thousand, he would give me injections in my chest that would give me real breasts of my own, at least for a while. The injections would break down over the course of six months or so. And, since the gel that was being injected wasn't in any sort of container, this treatment couldn't get me breasts that were larger than a B-cup. But, really, with my slim build, anything larger would look ridiculous anyway. And, besides, I had a job where I was most definitely a man. Small breasts could be held down with an Ace bandage. Big breasts would be impossible to hide.

Amy and I split the expenses. It really wasn't a problem. We were living like students still but each had a grown-up's salary. We could afford to spend some money on things we wanted to do. And, by this point, Amy had me fully on board with her plan.

The hormone treatment involved both injections and pills. I began to see effects remarkably fast. Within two weeks, my hips were filling out and I was getting little breast buds. These were constantly sore but I found that rubbing them relieved the soreness and also felt pretty terrific. By the end of a month, I had lost most of what little body hair I had. My facial hair had almost stopped growing at all and, below my neck, I was almost hairless except for a little triangle of pubic hair above my penis. I still had to shave my legs and underarms (and my face for that matter), but what I was shaving off was just a little bit more than peach fuzz.

A month before the reunion, I went in for my breast injections. By this time, my breasts were almost a true A-cup. They didn't look bad, really, but a little filling out would make them look better. The procedure took only about an hour and it wasn't too uncomfortable. This doctor may have been a bit on the shady side, but he did good work. When I looked at myself in the mirror, I found that I had gorgeous, though still small, breasts. (I found it hard to resist the temptation to fondle my own breasts. In fact, I often didn't resist the temptation. My showers were autoerotic experiences and those experiences didn't end at the shower door. I often played with my new toys as I lay in bed falling asleep or even sometimes when I was driving.)

During these three months, Amy spent a lot of time schooling me so that I could walk confidently in the highest of heels and move and talk like a woman. It's surprising how much you have to learn to do differently to pass as a woman. Women hold themselves differently and they talk differently. Some differences are obvious, but some are quite subtle. Fortunately, Amy was a very good teacher. By the time of the reunion, I was completely passable, even on pretty close scrutiny.

About a week before we left for the reunion, we went shopping together. I was en femme. It made for a good trial run and, also, it's much easier to shop for women's clothes when you appear to be a woman. It was fun. Amy and I spent a whole day shopping—just like two girlfriends. We had lunch together and talked about clothes and make up. Doing these things, I felt incredibly close to Amy.

And the clothes I got were terrific. We were planning to stay in town for four days and we picked out new clothes for me for the entire time. And, when I say 'new clothes', I mean everything: panties and bras, garter belts and stockings, slips, dresses, skirts and blouses, and, of course, high heels. And, because Amy wanted me to really feel the part, we picked out some very sexy teddies and other lingerie for me to sleep in.

Amy and I went out every night that week, with me dressed, of course. For the first few nights, it was like a finishing school exercise. Amy would find some small thing that I could do better. But the last few nights there was nothing to correct, even to Amy's critical eye. We just enjoyed going out together. Amy encouraged me to flirt with guys at the bars we stopped by. It was fun feeling the power that women have. I looked quite sexy and, with those looks, could get about anything I wanted from a guy. I don't think either Amy or I paid for our own drinks once during this bar hopping.

Finally the travel day arrived. I was packed and ready to go the night before. I got up earlier than Amy on that Thursday morning and, as I shaved my legs and underarms in the shower, I had a little time to reflect. I know it must sound crazy to most guys, but I was really looking forward to having four full days living as a woman. I knew that Amy and I would have a wonderful time being "lesbian lovers" and that this wouldn't limit the range of our future lovemaking at all. We would still explore all facets of our sexuality together.

I was dressed when Amy got up and I made us both breakfast before we started on our drive. It was going to be a long drive and it would have been nice to fly instead. But that raised the problem of my identification. I didn't think I could explain to the TSA people why Stephen looked like Stephanie and I really didn't want to try. While I cooked breakfast, I thought about my vow that I was never going back home again. Well, I wasn't the first person who'd gone back on such a resolution.

The drive was uneventful. Amy and I traded off driving and I found it kind of interesting to drive with high heels on. This was the first time I'd done that; Amy had always driven when we'd gone out together with me dressed. Doing these ordinary things dressed as a woman made the dressing seem less like play and more like a true transformation. I began to feel like a woman—not just a man fantasizing it for a moment when Amy is fucking me with her strap-on.

After Amy and I got settled in our hotel room, we decided to rest for a while before going out to dinner. Resting turned out to be preceded by a long, sweet love-making session. Amy took charge but she made love to me in the tenderest way—gazing lovingly into my eyes as she gently moved the strap-on dildo in and out of my ass. She finished me off by kneeling between by thighs as she fucked me and playing with my breasts as she had me stroke myself off. After I spurted all over my belly and breasts, Amy gently fed me my cum, allowing me to suck it off her fingers. She took off the strap-on and was ready to nap then, but I couldn't leave it there. I positioned myself between her thighs and licked her lovingly till she climaxed with my tongue pressed between her slick lips. Then we fell asleep in each other's arms.

After our nap, we had a good meal and then watched a movie in our room. We didn't make love before we went to sleep—at least we didn't make love by having sex. But just as we were ready to drift off, Amy rolled up so that she was leaning over me and, gazing down into my eyes, told me how the week was going to go. She was in charge, completely, of what we would be doing. She would take into consideration my feelings as she saw fit, but she would be calling all of the shots. And, furthermore, as much as she liked the fluid sex sexuality we had developed and didn't want to rigidify our sex roles, for these four days, I was the girl—I was the only girl and I was only to be a girl—though she assured me that my 'clitoris' would get ample attention. That was fine with me.

It turned out that Amy had made plans for me—none of which I knew about in advance. She discussed them over breakfast. The reunion wasn't until tomorrow night but Amy had arranged a date for me tonight. When she first told me she'd arranged a date for me with a guy, I thought this was another game—maybe she was going to dress up like a guy and we'd go out in reversed roles. But it soon became clear that she'd set me up with a real guy. I was shocked and scared—the more so when I heard that the guy she'd set me up with was Jerry.

"I'm not going out with Jerry!"

"Wait, hear me out first," Amy said in her voice that always calmed me.

I heard her out and I still didn't think I liked the idea. But I agreed to go along with it. Jerry had no idea that it would be me that he would be going out with. Amy had, through a clever and intricate plan, located Jerry's e-mail address, drawn him into a chat room site, and written to him as if she was a pre-op transsexual who was shy and inexperienced but interested in dating guys. She sent Jerry some of the pictures she had taken of me when I was completely transformed into my feminine persona and they'd engaged in some pretty hot on-line exchanges. After the virtual relationship had developed, Amy told Jerry that she would be visiting his town on business and proposed that they meet. Jerry sprang for the bait and the date was set.