Never Going Back Again

So, Jerry wasn't thinking he was getting another crack at his high school victim again; he thought he was going to have a chance to live out a fantasy of having sex with a shemale.

Amy hadn't captured the chats to a text file but she let me read some of e-mail they had exchanged. Jerry sounded both respectful and very interested. Despite having been the initiator of the explicitly sexual discussion between them, Amy had played coy toward the end. She told Jerry that hadn't had any sex since beginning her transformation and that she'd never been with a man at all. She didn't want to him to expect too much. She may not, she said, be able to carry things as far in real life as she had in the on-line sex talk. So, she'd set things up so that Jerry had to do the seducing.

I had to agree that it might be fun to be in the role that Amy had cast for me—especially with Jerry doing the pursuing. So, while I was still a little uneasy, I agreed to go through with it. Amy said that she would shadow us for the evening and be just a phone call away if anything went wrong and I wanted to be rescued.

Late that afternoon, Amy helped me get ready for my date. We did the whole rigmarole: scented bath, full body depilatory, lotion, and even a douche, before starting to get dressed. Amy picked out an outfit that was sexy, but in an understated way: powder blue matching bra, panties, and garter belt; taupe stockings and a short, chocolate brown, leather skirt, with a cream-colored silk blouse. She took extra care on my make-up and hair. Finally, I slipped into three-and-a-half inch brown leather shoes that coordinated with my skirt.

It was time for me to go down to the lobby to meet Jerry, but I stopped in front of the full-length mirror to evaluate my appearance. I knew I was going to look hot but I was surprised to see what an incredible job Amy had done. I didn't look masculine in the least; indeed, I was a stunner.

Amy said, "You can get anything you want from him tonight, hon. You're a knock-out!"

So I went down to the lobby with confidence. As I waited in the lobby, this began to melt. I worried again about what would happen if Jerry recognized me. Then all sorts of concerns came to mind. What if he was one of those guys who was fascinated by trannies but couldn't accept that in himself and, to prove his masculinity to himself, beat up trannies? There was no reason to even suspect this. But my mind was reeling.

I felt my cell phone vibrate and dug it out of my purse. It was a text from Amy: "Don't worry. Everything will be fine. You're gorgeous!" I took a deep breath and relaxed.

Jerry showed up just as I was putting my phone back in my purse. I tried to give the sort of smile a woman is supposed to show her date. Jerry smiled back and then I had one of those pleasures that ordinary men have no experience of. I watched Jerry's eyes take in my visage and I could see the excitement begin to course through his body. His eyes dilated and his face flushed. What a feeling of power I was flooded with. My fears melted away.

Putting his arm around me, Jerry led me out the door to his car. He made small-talk on the way to the restaurant. It was clear that he had no intention of steering the conversation toward my transsexuality. That was good. I didn't want to talk about that. He just talked about his interests and asked me about mine. As it turns out, it's easy for a woman to be a good conversationalist on a date with a man. All she has to do is pretend to be interested in whatever he talks about.

The restaurant was terrific, and expensive. Jerry was trying to impress me; and he succeeded. We sat at right angles at a table in the corner of the restaurant. Early on, I felt his leg against mine. Soon, he would slip his hand down under the table and place it on my knee. Before long, he was doing much more than just resting his hand on my knee. His fingers would trace a line up my thigh to the hem of my skirt and, sometimes, slip under my skirt just a little. I pushed my skirt down several times—not in a way that would say "no," I hoped, but in a way that would say, "not yet." I guess I did it right because he wasn't discouraged.

Jerry suggested going back to his place for drinks. I hesitated only for effect. He persisted and I relented. As we walked out of the restaurant, I saw Amy in the bar, sitting by herself with her phone on the bar by her drink. Good as her word, she was ready to rescue me if need be. I didn't think the need would be and I smiled at her as I walked out of the restaurant with Jerry's arm around my waist. I suspect that we were still in view when I had to reach down and pull Jerry's hand back up to my waist after it had found its way to my butt.

Jerry's apartment was nice enough, even if the décor was uninspired. He turned on some music and gestured for me to sit down on the couch while he poured us some wine. When he returned with the wine, I was carefully positioned on the couch in such a way as to show just a bit of my stocking top below my skirt that had hiked up as I crossed my legs. And, by throwing one arm along the couch back, I was able to make my blouse pucker apart a bit at the top—not enough to show anything but enough, I hoped, to draw interest.

After Jerry sat down, about as close to me as possible, I realized that deferred gratification wasn't really Jerry's thing. He only took one sip of his wine before setting it down so that he could put his hand on my knee. From this position, it was much easier for him to slide his hand between my thighs and begin to raise my skirt even higher.

I pushed his hand away gently, being sure to let out a little giggle that showed him that this was all just play. Then Jerry stunned me. Putting his hand on my cheek, he turned me toward him and gently brought my lips to his. He kissed me tenderly, but passionately. And I kissed him back.

I was surprised by my reaction. I'd never been kissed by a man. And earlier in the day, when I'd thought about tonight's date with Jerry, I'd imagined all sorts of things, but I hadn't imagined that he would kiss me—certainly not in the sweet, but sexy, way he was. If I had thought about it, I don't know how I would have imagined my response. But, now that it was happening, my response was as full of passion as his approach.

Being kissed by a man who was filled with lust for you is an exciting experience. It made me hot. I could feel my dick hardening in my panties and my response wasn't limited to that region of my body. My pulse was racing and my skin was flushed. I could feel that my nipples were hard beneath my bra.

Still kissing me, Jerry moved his hand up to begin unbuttoning my blouse. I made no effort to stop him, or even to slow him down. Instead, I put my hand on his cheek and pulled his mouth more tightly to mine.

When he had several of the buttons of my blouse undone, Jerry slipped his hand in my blouse and massaged my breast through my bra. That felt great—especially when I heard him moan with pleasure. But it felt even more wonderful when he slipped his hand under my bra and began caressing my breasts directly.

He managed to pull his hand away long enough to finish unbuttoning my blouse and, pushing my bra up out of the way, began kissing and then sucking one of my breasts. I lay back on the couch and pushed gently on the back of his head to encourage him. With my nipples being so hard, I could really feel each distinct flick of his tongue.

And then I felt his hand moving up my thigh, under my skirt. I was a little scared. I knew he was hot and bothered but what if the actual feel of my hard little cock turned him off? What if he got weird about it? But he didn't. He fondled my erection lovingly and passionately, first through my panties and then by slipping his hand under them.

By this time, my skirt was bunched up around my waist and Jerry had full access to my cock. It felt great to have his hand caressing me like that. He began pushing my panties down and I raised up my hips to help him. In order to get my panties completely off, Jerry had to move down, which put his face inches from my straining little pecker. He held back, but only for a second. I felt his lips surround my cock and felt his warm, wet tongue sliding on and off my shaft. And then he cupped my little balls in his hand while he sucked me deep into his mouth.

What an incredible sensation that was! I managed to pull my blouse off and unhook my bra without distracting myself too much from the pleasure Jerry was giving me. As I did that, he moved down until he was on his knees between my thighs, still working my cock with his mouth. Sometimes he would press his lips all the way to the base of my cock, pressing tight against my pubic bone, and hold still for a moment. Then he'd swirl his tongue around stimulating the most sensitive part of my cock.

If he kept this up long, I was surely going to blow my load in his mouth. But he stopped. He climbed up and, at the same time, moved me so I was lying down on the couch. He lay next to me and began to undo his belt. I moved his hand away and set about finishing the job he'd begun. When I had his belt and pants loosened, I reached down for his cock. It was blistering hot and hard as can be. I stroked it hard and Jerry pressed his lips to mine again in a heated kiss. God his cock felt good! And so did his lips!

After a few moments of kissing passionately while I stroked his hard shaft, I moved him gently so that he could tell I wanted him to stand up. When he did, I got down on my knees before him and said, "Now, my turn."

I pulled down his pants and gazed for a minute at his hard cock, which was just inches from my lips. As I realized how much I wanted to feel his cock in my mouth, I thought back for just a second on how different I felt now than I had back in high school when I was servicing Jerry. I couldn't deny that I'd been aroused during those encounters. But things were very different now. It wasn't simply that I was more aroused now—though that was certainly true—it was that I didn't feel guilt or shame. I wasn't "servicing" Jerry now and he certainly wasn't using me. That changed everything. Now I could really enjoy the feelings I was experiencing.

So I took Jerry's smooth, hard cock into my mouth with great pleasure. Try as I might, I couldn't get my lips down to his pubic bone the way he could, and easily, on mine. But it was fun trying. As I sucked him, I gently cradled his walnut-sized balls in one hand while I stroked my hard little pecker with the other. I wasn't trying to drive him to an orgasm—yet—I just wanted to enjoy the feeling of sucking his cock and fondling his balls.

It was clear that Jerry would have been fine with my finishing him off right there and then, but I had other ideas. I stood up and kissed him again. This time our mostly naked bodies were in contact. I could feel his hot cock against my abdomen and I felt mine pressing against his. Then I asked him to show me the way to his bedroom. He was happy to do so.

I followed him, still in my garter belt, stockings, and heels, to his bedroom. When I saw that he had mirrored closet doors, I decided to get back on my knees and suck him again. I've always thought that there was nothing sexier than a woman, especially one in high-heels and stockings, on her knees lovingly sucking a guy's hard cock. I hoped that Jerry had similar feelings and, if so, he would watch me in the mirror. I planned to sneak a few peaks myself.

Several times when I managed to catch a glimpse of the action in the mirror, I saw Jerry staring at the action, too. It made me smile (around his cock) to see how engrossed he was in what was happening. It was incredibly hot.

I was willing to get Jerry off then and there, but he pulled me up to my feet again. He placed his hand gently under my chin and raised my chin up so that he could kiss me again. This time, he pressed his tongue deeply into my mouth. I sucked on it hungrily.

Jerry maneuvered me back to the bed and gently laid me down. He put his hands between my thighs and gently pushed them apart. And, then his lips were back on my cock, bringing it back to full hardness. He licked my ball sack, playing with my almond-sized balls with his tongue. He used his hand to lift up my balls and then I felt his tongue tickling the skin behind my balls. He kept pressing my thighs further apart and moving his tongue back further and further toward my asshole. It sent shivers of pleasure through my body as the tip of his tongue flicked across my hole.

Not content with the access he had in that position, Jerry rolled me over on my stomach and then raised my hips up. Now he had free access to my asshole, and he made the most of it. He really got into teasing my ass. He would trace a line up the insides of my thighs with his tongue, pulling away just as he almost touched my ass. When he licked the skin behind my ball sack, I could feel his nose just barely touching my ass sphincter. When he finally tired of teasing me, he thrust his tongue as deeply into my ass as he could. It took my breath away and I could tell that Jerry loved causing me to gasp with pleasure.

Jerry moved up until his thighs were between mine and his cock was lined up with my now wet ass. I was so ready for this now. I moaned with pleasure and moved my hips invitingly. He accepted the invitation. I felt the wonderful pressure of his cock against my asshole and, then, he slid in. He was big, but I was used to getting big things in my ass by now and I took him without discomfort—and with extreme pleasure.

God! It felt fantastic. Jerry held my hips lovingly while he slowly and sensuously slid all the way into me. I felt him shudder with pleasure when he was completely buried in me. And then he began to fuck me—or make love to me—whatever. It was wonderful.

I could feel Jerry building to an orgasm and I did everything I could to encourage it. I moved my hips to his rhythm and I clamped down on his cock with my ass to milk his cock. I was gripping him so tightly I'm sure it felt to him like he had a hand around his cock. And I was getting the desired result. His breathing became hard and ragged and then I felt him grip my hips tightly and plunge hard into me, spewing his seed deep in my bowels.

When he finished squirting, I continued to milk his cock with my ass muscles for a few moments. Then we collapsed onto the bed while he swooned in his post-orgasmic ecstasy. It was strange. I hadn't cum, but for some reason I felt completely satisfied lying there with Jerry on top of me and his wonderful softening cock still buried deep in my ass.

Eventually, we untangled ourselves and I got up to go to the bathroom. It was only then, in the bathroom, when I took off my heels, stockings and garter belt. As I sat on the toilet, peeing and letting Jerry's semen slip from my rectum, I had a chance to reflect. I'd just gotten fucked by the same cock that had been the instrument of my abusive domination during most of my last year in high school. But the experience couldn't have been more different from those old times. Tonight, Jerry made love to me, as if I was a woman. And I responded in just the appropriate way.

As I stood up, I looked in the mirror. I liked what I saw. I was a sexy shemale with a very feminine figure and a beautiful face. My penis, which had been my shame for so many years, was a sweet little enhancement.

When I returned to the bedroom, Jerry was under the covers but not asleep. I clambered under the sheets and snuggled up next to him. The feel of his body next to my silky smooth skin excited me and it wasn't long before my dick was hard and I began rubbing it against his thigh. Jerry touched my dick gently with his hand and said something like, "Looks like we have some unfinished business here." He threw the covers back and began moving slowly down my body. He stopped with his mouth at my breasts for a long time, kissing and licking my breasts gently and then sucking them deep into his mouth. Eventually, he moved down further and I felt his tongue trace a line down my abdomen to my penis.

His mouth on my penis now was even more intense than it was earlier. I sighed and moaned with pleasure as he made love to my penis. That was wonderful. But then he stopped. What he did next stunned me.

Jerry pulled himself up until he was lying next to me, his back toward me and his ass pressed toward me. He reached back and pulled me toward him so that we were spooning. I felt my tiny but terribly hard cock press between his buttocks and I realized what he wanted. To say I was surprised would be a huge understatement. But I was certainly up for it.

As soon as Jerry was sure I understood what he wanted, he got up on his hands and knees. I positioned myself behind him and pressed my straining dick toward his eager asshole. He wasn't lubricated so I spit on my hand and wiped it on my cock. Fortunately, even hard I was small enough that I didn't need a lot of lubrication to press into his ass. I entered Jerry easily and, as I began working in and out of his ass, I could tell that he was loving it as much as I was. I held his hips tightly so that I wouldn't slip out as I pulled away from him, and fucked him as hard as I could.

I'd fucked Amy in the ass before so you might think that this wouldn't be much different. But it was. Maybe just because of the idea that it was a guy I was fucking, or may because it was Jerry in particular. Whatever! This was a different feeling than I'd ever experienced. It didn't last long, though. Jerry reached back between his thighs and put his hand behind my tight little ball sack, pressing me into him in the rhythm he wanted. And apparently it was a good rhythm for me, too, because it wasn't long before I was spurting my seed in his tight ass.

We collapsed and this time it was my time to just drift off while Jerry got up and went to the bathroom. When he returned, he snuggled up behind me and groped my breasts for a few minutes before we and we both fell asleep. I woke up several times during the night, always with Jerry's arms around me and sometimes feeling his hard cock pressed against my butt cheeks.

When I finally awoke for the day, Jerry was in the shower. I decided to join him. He'd probably already soaped up and rinsed off but he let me soap him up again, and he soaped me up, too. That was nice. Really, it feels fantastic to run your hands over a slick and soapy body that's really beautiful.

We got out of the shower and decided to have some fun. I got on my knees on the plush bathmat and gave Jerry a morning blow job. After that, I grabbed the clothes I left in the living room and went back to Jerry's bedroom to get dressed. Jerry watched me as I put on my garter belt and fastened my stockings. Normally I would have put on my heels last but with Jerry examining my every move, I thought it would be nice to get them on sooner. I asked Jerry to help me with my bra. I could do it perfectly well myself, of course, but I appreciated the attention. He fastened the clasp and then began groping me from behind. His hands were all over me, sliding up under the cups of my bra that he'd just fastened and running down my abdomen to encase my hard little dick. I stood there for a while enjoying Jerry enjoying me.

Then Jerry turned me around and sank to his knees. Now, it was my turn for a blow job. Jerry worked my dick sweetly but with urgency. From where I was standing, I could watch the action in the mirror. What I saw excited me. There was a beautiful woman, though with one remnant of masculinity, being sucked by an obviously eager guy. When Jerry slid his hand up to put his finger in my asshole, I felt my sphincter involuntarily clench down on his finger as I spewed my semen in his mouth. He swallowed before standing up and kissing me.