To tell the truth, I never really figured out how to do the guy thing very well. I was always small for my age. People used to say that I’d shoot up someday, but it never happened. All through my school years, I looked about two years younger than my classmates. It didn’t make for an adolescence filled with confidence, or even security. I was picked on mercilessly—teased, of course, but also actually beaten up from time to time.
It didn’t help that I wasn’t just small of stature but also small in the “manhood department”—so small, in fact, that in my case, it should really be called the “boyhood department.” I didn’t always realize how short I came up, so to speak, in this department. As a kid, who knew what normal was there? In middle school gym classes, I got my first sense that I was different. The other boys were all bigger than me, but some didn’t seem to be all that much bigger. I learned from the internet that there was a difference between growers and showers. And I just figured I was a grower. It’s not like I’d seen any of these guys hard. So I told myself that, even though my inch-and-a-half soft dick looked much smaller than their dicks, they probably didn’t get much bigger than my three inches hard.
By the time I got to high school, gym class was a source of embarrassment to me—especially when it was time to shower. I tried skipping showers, but the P.E. teacher caught me and read me the riot act. Then I tried to delay going to the showers as long as I could, pretending to be doing something in my locker, hoping that most of the guys would have cleared out of the shower before I had to go in. I walked in with the towel around me and only took it off as I was stepping under the water. Wearing the towel was a provocation for teasing in itself, but it was better than letting people see me naked.
I mostly tried not to think about whether I was different from other guys there. When I did think about it, I kept telling myself that though they were much larger than me when they were soft, they probably didn’t grow as much—and certainly not as much proportionately—as I did. That illusion was shattered one Friday in my senior year, just after I’d turned eighteen. I had to go back to the locker room after school to get my gym clothes. The door was locked and I was just about to give up—resigning myself to my fate of getting a grade reduction for not having clean gym clothes on Monday. Then I noticed a window that was open. It was a low window and it was very easy to just climb in.
Strangely, my heart was pounding when I closed the window after me. It was like I was some sort of thief, even though all I was going to be taking was my own dirty gym clothes. As I walked to my locker, I heard something in the bathroom part of the locker room. Someone was there. I had to walk right past that area to get to my locker. There was no avoiding it but I tried to walk very quietly, looking carefully to see whether the person would be likely to see me or not.
When I stepped around the corner, I froze. Jerry Greyson was standing with his back to me, with his pants down to his ankles, jerking off into one of the sinks. His arm was pumping furiously and he was lost in his build-up to an orgasm. I was transfixed; I couldn’t move. I just stood there, dumbfounded. I stood there too long—long enough for him to see me and, worse, long enough for me to see him.
I don’t know why Jerry turned around. Maybe I’d made some noise, though I didn’t think so. Maybe he could see me in the mirror. I don’t know. But he turned around so that his torso was sideways to me. I guess he was looking at me but I didn’t look at his face. I looked at his hand—the hand that had been so furiously pumping his dick. I saw his cock. And I was stunned.
I’d seen Jerry in the shower before. I guess I’d noticed guys’ dicks because I was so self-conscious about my own. He was about four inches soft, I remembered. So, I’d figured, consistent with the theory I’d been clinging to, that he was probably not much bigger when he was hard. Wrong! Jerry’s cock was a good eight inches, maybe nine. And it was fat; his fingers didn’t stretch around it completely.
He said, “Hey, asshole! What are you looking at?” The answer was obvious, of course. I couldn’t take my eyes off his cock. But I couldn’t answer the question. I was speechless.
“Get the hell out of here,” Jerry yelled. Later I figured out that he must have been embarrassed—humiliated, maybe. It was hard for me to conceive of Jerry feeling that way. He was the oldest guy in our class—the first to get his driver’s license when we were sophomores. He always seemed so self-confident. All could hear in his voice then was anger, directed at me. I ran away as fast as I could, forgetting completely about my gym clothes.
On my way home, I had time to think. I’d now seen what a real guy my age looked like hard. I couldn’t write him off as a freak of nature like I’d been doing with the guys I’d seen pictures of on the internet. This was just Jerry. When he wasn’t hard, he looked pretty much like all the other guys on my gym class—maybe a little bigger, but not a lot. Is this what the other guys looked like hard? Is this what a normal guy looked like?
I couldn’t think about anything else all night. When my parents thought I’d gone to sleep, I was actually in my room stroking my dick to see how big I could make it. I didn’t have any trouble getting hard; my dick had been rigid most of the night. When I was clearly as big as I ever got, I tried measuring myself. Three inches! That’s all. Sure, I could measure from the underside and get another half inch. But I knew that was a cheat. I was three inches and that was all there was to it. And I could easily wrap my fingers around my dick, overlapping thumb over the first knuckle of my fingers. I was the freak of nature—not those guys I’d seen on the internet.
My dismay didn’t keep me from enjoying one of the most intense jack-off sessions I’d ever had. All the while I was stroking my little pud I thought about what I’d seen Jerry doing and I wondered what it would feel like to have a cock that size—to wrap my hand around it and feel the power of such a shaft. I quickly spewed my clear semen on my stomach.
As intense as the orgasm was, a single orgasm just didn’t do it. As I was trying to get to sleep, I needed another wank. And I woke up in the middle of the night to jerk off again. Despite all the whacking off—which produced some terrific orgasms—I didn’t sleep very well. I was troubled.
I was troubled even more when I finally got up and logged on to get my e-mail. There was a message from Jerry. It said:
Hey Dirtbag. You’re in deep shit. Meet me in the locker room at 4:30 on Monday or you’re going to be in even deeper shit. Be there! Jerry
I knew that Jerry did some kind of work for the gym teachers after school, which is probably why he had access to the locker room. But what did he want me to meet him there for? I didn’t know. But I couldn’t stop worrying about it.
On Monday, I saw Jerry around the school a couple of times but I tried not to let our eyes meet. I was embarrassed and frightened. I knew I couldn’t stand him up. He’d make me pay for that. But I couldn’t bear to think about what he was planning to do to me.
4:30 came soon enough. The locker room was empty at this time of the day. Unlike Friday, the door was ajar. When I stepped in, it closed after me and I heard the latch click ominously. I walked toward the bathroom part of the locker room, where I assumed Jerry would be, to meet my fate.
“Stop there!” Jerry commanded as I just came around the corner, standing almost exactly where I had last Friday. He was intent on establishing his command of the situation, as if there was any doubt.
“So, you like sneaking up on guys and getting a peek at their cocks, do you?” I started to explain what I was doing in the locker room on Friday but Jerry wasn’t interested. He had a narrative to lay out and facts weren’t going to get in his way.
“Did you like what you saw?”
Well, how do you answer a question like that? If I said ‘no’, he’d claim that I was dissing him. If I said ‘yes’, he’d say I was gay. So, I just ignored the question.
“Don’t have anything to say, huh, dickbreath?” And, he was right. I didn’t. “Okay. You’ve seen mine. Now take your clothes off and show me yours.”
I doubt that he’d ever noticed me naked so I don’t think this was a command specifically designed to humiliate me. I think he just wanted to establish that he could make me do what he wanted. But, whether he knew it or not, this was the most terrifying demand he could make of me. (Well, I suppose it would have been worse in front of even more people. But the mere thought of showing myself naked to anyone was horrifying to me.)
I knew I couldn’t refuse, though. Jerry had never really been one of my tormentors; and I didn’t want him to become one. He was popular and I knew he could make my life miserable if he chose to. So I started taking off my clothes. I unbuttoned my shirt and removed it first. Then I took off my shoes and socks. I was saving the worst for last. But there was no avoiding it. Finally I was stripping off my jeans. I stood there for a few seconds in my jockeys before Jerry urged me on. I bent over while I was lowering my underpants, but, finally, I had to stand up and reveal all—which wasn’t very much, of course.
I was nervous and embarrassed and my dick wasn’t even its normal inch and a half while soft. It was as if my dick was trying to hide. Maybe it was three-quarters of an inch long now; maybe not even that long. My balls, which were only marble sized in any case, were drawn completely up to my abdomen, making it look almost as if I didn’t even have a ball-sack, much less real balls. I could have been a woman—or even a little girl—except that you couldn’t see a slit behind what looked like a slightly protruding clitoris.
Jerry did a double take and then just burst out laughing. Jesus! It was humiliating. I covered myself with my hands but he would have none of that. He made me move my hands away expose myself completely. God, I wanted to die.
“What are you?” he said in disbelief. “Are you even a guy?”
“Yes, I’m a guy!” I snapped back angrily, but I knew his question was a reasonable one given the evidence at hand.
“Sheeze! Does it get any bigger than that?”
“Yes,” I said, knowing that it didn’t get enough bigger to really put the questions about my manhood to rest. Still, I certainly wasn’t going to say, “No.”
“No!” I wasn’t about to humiliate myself even more in front of Jerry.
“I’m serious. Show me. That is, if you don’t want the rest of the school to know that calling you a ‘pencil dick’ would be an exaggeration.”
Well, of course I didn’t want him to tell other people about me. So, what else could I do? I started stroking my dick. It wasn’t working very well. It got a little harder and bigger, but I couldn’t really get an erection.
“Here,” Jerry interrupted. “Come on over here. I’ll give you another look at what a real cock looks like.”
I walked over so that I stood about four feet from him. “Closer,” he demanded. When I was just two feet from him, he told me to unzip his pants and take out his cock. It was difficult to do from this angle and I sort of struggled with it for a bit. When I leaned over to see more clearly what I was doing, Jerry pushed me down onto my knees. I really didn’t like that position. I feared I knew what was coming.
“Well, dickwad—or maybe I should say, ‘dickless wad’—reach in and pull it out. You can have more than a look. You can have a feel,” he continued, as if that was what I wanted.
When I reached in his jeans and through the opening in his boxers, I could feel the heat of his crotch. And, immediately, I felt cock. It was soft, but still felt full. As I pulled it out, I thought about the fact that I’d never felt a real cock before and I realized what a pathetic imitation of a cock I had between my legs.
“This one does get bigger,” Jerry said. “Stroke it for a while.”
I did, and it did. I felt it fill in my hand and harden. It rose to point upwards of horizontal and got completely rigid. I was, of course, at Jerry’s mercy; I was completely subservient to him. But, if the truth were told, I wouldn’t have let go of his cock if it were up to me. It was a surprisingly pleasant experience. I’d neverBut, of course, I was hoping that it wouldn’t go any further. It was one thing to touch him and feel his cock. But I wasn’t into any gay action.
“Stand up,” he said, pulling me up. “Let’s compare.”
Shit! This wasn’t what I wanted at all. As I got to my feet and we were standing toe-to-toe and dick-to-dick, the huge difference in size wasn’t the only thing that was obvious. It was also apparent that my dick did get bigger. It was now at its full three inches and as hard as it every got.
“Well, I’ll be…you were right. It does get bigger. It gets bigger when you get to feel a real cock.”
What could I say? I blushed and tried to utter a dissent. But the truth of what Jerry had said was obvious; it was before both of our eyes.
“So you like this, huh? Well, then, you’re in for a treat. You can stroke me until I shoot my wad.”
I was actually very relieved by this. A moment ago, when I was on my knees, I was sure that he would be demanding a blow job. That would have been awful, I think. I don’t know whether I could have carried it off even if I’d tried. So a hand job seemed like a reprieve to me.
It felt weird stroking Jerry’s cock. Part of it was, of course, the extreme difference in size between his cock and the only other dick I’d ever touched—my own. But part of it was the fact that I was doing it from the other side. That was a new experience, too. Apparently, I was doing okay. In a matter of minutes, he was getting ready to shoot his load. I knew this was going to be over soon and I decided to really try to focus on the feel of Jerry’s hard cock in my hand. That actually felt really good. I don’t understand it but I felt a sense of power as I controlled it.
Then, before I really realized that it was going to happen, Jerry was shooting his cum. And, when I say ‘shooting’, I mean shooting. String after string of creamy white cum shot out, right onto my abdomen and my hard, pathetic, puny pecker. I had no idea anyone could shoot cum so far. When I came, there was a dribble—sometimes only an oozing—of clear fluid. This was like a different sort of thing entirely.
I was immediately embarrassed and really needed to get cleaned up, dressed, and out of that scene. But Jerry had other ideas.
“Wait,” he commanded with authority even though he was still panting. “Don’t waste that. Use it for lubrication and stroke yourself off. You got all excited. You might as well get off.”
The idea of masturbating in front of Jerry was humiliating but the idea of stroking my pecker, which was still almost painfully hard, had its attractions. As I began stroking my dick, I realized that the lubrication of Jerry’s cum provided an exciting new sensation. My dick felt wonderful with my fingers sliding smoothly up and down my little shaft. Soon, I forgot completely about Jerry’s presence and I was pumping my dick furiously.
And then I came. I probably came harder than I’d ever come before. But it was still a feeble little dribble of colorless fluid compared to Jerry’s impressive load.
“That’s all you’ve got?” Jerry said incredulously. “Sheeze! You really are a pathetic excuse for a guy, aren’t you?”
I didn’t answer him. There was no need. I reached for my clothes without cleaning up and, this time, Jerry didn’t stop me. I got dressed as fast as I could and headed for the door.
“Meet me here again tomorrow—same time,” Jerry called to me as I left. I knew I’d have to comply. But I didn’t want to think about it now. I just wanted to get home and get in the shower. As I walked home, though, I found myself sniffing my right hand—the hand I used to stroke myself. I could smell Jerry’s musky scent on my hand. It was strangely arousing.
When I got home, I made an excuse to get into the bathroom to take a shower right away. I couldn’t wait to clean myself off. But, as I waited for the hot water, I raised my hand to my face again—I thought only to take a last sniff of the scent. But I was wrong. I wound up licking my hand clean. It was dry, of course, by now. But as I licked it, I could taste Jerry’s cum. I didn’t know why I was doing that and rather than think about it, I just stopped and got in the shower to let the hot water erase all signs of my afternoon’s shame.
I awoke over and over again through the night from strange and unsettling dreams. They were very sexual and they all involved large cocks. In one dream I had a huge cock—not just one like Jerry’s, which I now realized was probably pretty normal, but an enormous cock, two feet long and as big around as a 2-liter bottle. But in most of them I was stroking someone else’s big cock and embarrassed by the size of my own. Too bad that those second sort of dreams were the ones based on reality.
I kept my date with Jerry the next day. And, as things developed, I wound up meeting him either in the gym or somewhere else of his choosing two or three times a week. My servicing of him developed, as might be expected, from hand jobs to blow jobs, and eventually to taking his cock in my ass. He had his own sexual boy-toy and, unless I wanted to be humiliated in front of everyone in the school, there was nothing I could do about it.
It’s not as if I didn’t have sex with girls, though. In fact, I wound up having sexual experiences with a surprising number of girls. For all the reasons I’ve explained, I didn’t have any self-confidence. So I didn’t ask girls out. They asked me out!
It started with Eileen, Jerry’s girlfriend. She told me that Jerry couldn’t take her to a party she wanted to go to because he had to go out of town with his family. And she wanted to know if I would go with her. Eileen was a knock-out. I didn’t know why she wanted to go to the party with me. But I was flattered and more than happy to show up at a party with such a beautiful girl.
It wasn’t until later that I learned why Eileen asked me. After an awkward but okay time at the party, I was walking Eileen home and we cut through the park. As we walked past an area of trees and shrubs, Eileen grabbed my hand and led me into the woods. I knew that lots of young teenagers dodged into these woods for a quick grope or more. I was both flattered and scared.
Eileen pushed me up against a tree and stood in front of me. Her beautiful body pressed lightly against mine. I could feel her breath on my neck and it aroused me. My little pecker was standing at full mast. I wanted so much to touch her—to kiss her and maybe more. But I wanted even more not to let her touch me in a way that revealed my shameful secret.
I was out of luck. Eileen was groping my crotch almost immediately. And then she moved to the side slightly so that she could reach down my pants. Almost before I realized what she was doing, and certainly before I could stop her, she had her hand on my penis. I tried to pull away, squirming backward—to no avail.
“It’s okay,” Eileen cooed. “Just let me touch it.”
God! It felt so good to have another person’s hand encircling my dick. And such a soft hand, too. And the hand of such a pretty girl. I quit struggling and let her fondle me. It felt wonderful.
Eileen didn’t confine her groping to my dick. She plunged her hand down further and cupped my small balls gently in her hand. I felt so vulnerable when she did that. But it felt exquisite.
She backed away and said, “Let’s get a look at this little guy.” And that’s what she did. She unzipped me and then, for an ever better look, she unbuckled my belt and unbuttoned my pants so she could push them down to my knees, exposing me completely in the dim light.
My dick was rigid, sticking straight out its full three inches.
“It’s so cute!” Eileen said. These aren’t the words that a guy likes to hear—especially not in the tone she uttered them. But, she touched me again and there was no way I was going to do or say anything to stop this.
Eileen took my penis between her thumb and her first two fingers—just like you would pinch something—and began stroking me rhythmically. I looked down and I didn’t like what I saw. The way she was holding me made my dick look so tiny—like it had to be held by tweezers. But I loved how she was making me feel. When I realized that she wasn’t just going to tease me, I let myself go and came to an intense orgasm. It was the first orgasm I’d ever felt from another person’s touch.
Even in the dim light, Eileen could tell that my ejaculation was feeble and tiny. Again, she said, “That’s so cute!” in a tone that was completely humiliating. She used her fingers to wipe up the drops of clear fluid that were clinging to the end of my softening penis and brought them to my mouth, pressing them between my lips for me to taste. I yielded to the pressure and cleaned her fingers of my semen.
I felt as if there was something I should do for her, after she’d caused me such pleasure. But she seemed intent on leaving the scene and heading home. I had to hurry to catch up with her after I’d managed to pull up my pants and fasten them. I tried to strike up a conversation with Eileen on the way to her house but she didn’t seem interested. I wasn’t really a very good conversationalist, anyway. So, we walked in silence.
When we finally reached her house, she turned to me to say goodnight. I knew there was no kiss coming. I didn’t know yet what tonight meant, but I was under no illusions that she liked me. I decided, though, to be bold. I didn’t want to go home completely confused about what tonight was about. So, I asked—right out. Maybe I shouldn’t have. The answer wasn’t easy to hear.
“Why did you ask me to take you to the party tonight,” I asked in all innocence. There was a long pause; I guess Eileen was thinking about whether to be honest or to tell a kind lie. She chose honesty.
“Jerry said I couldn’t go alone cause other guys would hit up on me and he said I certainly couldn’t go with anyone else—then he added, unless it was you.” She paused leaving me in suspense just as Jerry had left her in suspense until she asked him to explain. I didn’t have to ask Eileen to go on. She volunteered the explanation.
“Jerry said that I could go with you because he’d seen you in the shower and he knew that you weren’t any competition. I pressed him to say more and he said that you had the tiniest dick he’d ever seen on a guy older than eight. He said that if I wanted to go to the party, I could go with you as my date. I did want to go, so I asked you.”
“And just back there…in the park…?”
“Yeah, well, I guess that was kind of mean. But I was curious so I thought I’d check you out.”
Eileen could see my face flush with embarrassment and humiliation. I think, maybe, she felt guilty.
“Aw, come on. Don’t feel bad. It’s not like it’s your fault you’re small there. And, hey, you got a hand job out of it. That wasn’t so bad, was it?”
I turned before she could see me start to cry. And I walked home with very mixed emotions. I still felt the warm, post-orgasmic glow. But I also felt the sting of humiliation. I decided that I didn’t like Eileen very much, even though I really liked the sensations her hand had caused me just a few minutes ago.
As it turned out, I had a lot of sort-of dates in the coming months—especially after I bought beater to drive around in. It usually wasn’t like real date—you know, we didn’t go to a movie or a dance together. No, usually some girl would ask me if I could take her to the downtown library one night to do school research or drive her home from some school dance. Some of the guys thought it was pretty strange that girls seemed always to want to get a ride with me. It certainly wasn’t my car—a 15 year-old clunker.
It took me a while to figure out what was going on. I started putting two and two together when I realized how similar these “dates” turned out to be. There wasn’t perfect consistency or I would have figured it out sooner. But after a while I realized that there was a pattern. It went like this. Girl finagles a ride on some pretext. I agree, cause I’m a nice guy. I have pleasant enough conversation with her until we get to our destination. Then, she acts like she’s very appreciative, leaning over to give me a peck on the cheek—never more of a kiss than a quick peck—to thank me for being such a “dear” and giving her a ride.. But her hand “accidently” rests on my crotch. And that starts it off.
She usually says something like, “Oh…what do we have here?” as if she’s really interested. At first—before I figured out what was going on—I was flattered. She’d massage me a little though my pants, which always got me hard really fast. (I guess it doesn’t take much time to fill a small vial.) And then she’d say, “Oooohh!” and unbuckle my belt and unzip my pants to get her hand down inside my briefs. And then…well, then it felt wonderful. A soft hand was caressing my little penis and I loved the feeling.
“Let me see,” she would plead. And I didn’t want her to stop touching me so I’d raise up so she could push my pants down to my knees. Then I was completely exposed to her. I knew she had to be thinking that I was tiny compared to e other guys she’d seen. I mean, we were all eighteen; it’s not as if any of these girls were virgins. I can’t say I didn’t care about what they thought about the size of my penis. I did. It made me feel awful about myself. But the girl would continue holding and stroking my rigid dick and I was willing to take a lot of humiliation to feel that.
Sometimes a girl would just feel me and then leave me hard and yearning for release. That was frustrating, but at least I felt the touch of a woman. Sometimes a girl would stroke me until I spurted my little load on my stomach or thighs. That felt wonderful. A few terrific times, a girl would take me in her mouth. What a fantastic feeling that was. And, once—just once—a very cute girl, Josie Markam, sucked me until I shot in her mouth. Jesus! What a sensation that was! I didn’t even object when Josie immediately kissed me and pushed my cum into my mouth for me to swallow.
Most of the time, the wonderful feelings these girls’ touches produced in me compensated for the feeling of inadequacy and shame I had at being exposed to them. But sometimes it wasn’t worth it. I didn’t like it when a girl would hold my penis between her thumb and first two fingers. That made me feel even more inadequate. It reminded me of the way Eileen had held me that day in the park. And once, a girl couldn’t hide her hilarity at seeing the size of my equipment. It was even worse that she kept trying. But once her first snorting laugh at my expense had come out, she couldn’t contain herself despite her best attempts.
It took me a while to figure out that my puny penis was a matter of girl gossip and lots of girls wanted to see for themselves whether an eighteen year-old guy could really be as small as they’d heard I was. Before I figured this out, I had started to think that all girls found some excuse to handle all the guys they were alone with. I liked that hypothesis better. But, when it was finally impossible to keep believing it, I resolved myself to the conclusion that I was the laughing stock of all of the girls in my high school.
Of course this humiliated me. And for some time, I avoided situations where a girl could get her hands on me. But finally I came to the conclusion that doing that wouldn’t stop them from talking about me. It wouldn’t keep me from being the butt of their cruel jokes. It would only keep me from feeling their soft hands on my hard little penis. So, I steeled myself to the humiliation in order to feel the human touch. I kept on agreeing to give girls rides when they asked. I was getting something out of it.
Once I wound up being the only guy at a sleep-over that one of the girls, Penny, had arranged, without her parent’s knowledge of course, when they were out of town. (I thought it was pretty strange for eighteen year-olds to have a sleep-over party, but I really didn’t know much about such things.) Six girls and one guy with a very small penis. There was lots of drinking and groping. (Well, the groping was all one way. When I tried to feel any of the girls up, they would stop me.) It felt good, at least if I ignored the remarks that were humiliating. Really, how many guys have had the soft hands of six cute teenage girls fondling them at the same time? The feeling of being touched was enough to make up even for humiliation of being measured in all sorts of ways. They measured me soft and hard. They measured my balls and by ball sack. In the end, they knew more about my genitals than I did.
In the course of all this, they got me hard lots of times and made me squirt my juice twice in just three hours, which was a record for me. They also got me, and themselves, pretty drunk. They still seemed in control, though. I was at the point where I would do pretty much whatever they suggested.
And what they suggested was that I get dressed up in girl clothes. I put up a bit of a protest, but not for too long. I just didn’t have the energy to fight. After all, it was a girl sleep-over. So what if I was just one of the girls.
At first, I thought it was just going to be panties and a nightie. But they wanted to make me up completely: paint my nails, do my face and curl my longish hair. This all took about an hour. Just when I thought the conversion was complete, one girl suggested that I was showing a little too much hair to be a pretty girl. I’m not very hairy, but I did have a bit on my calves and in my arm pits; and, of course, I had pubic hair. Not for long, though. They sat me on the side of the tub and I was soon clean shaven; except for the hair on my scalp, every bit of hair on my body was gone.
When they put my panties back on, I could feel the silky smoothness of the fabric on my body much more vividly than before. I found it very arousing, but I was too spent from having two orgasms to get hard from it. Before putting the nightie back on me, they fitted me with a bra and filled the cups with stockings so that I looked like I had breasts. After they had finished dressing me, I got a chance to see myself in the mirror. I looked okay. Slightly skinny, but not bad. When I looked down, I saw my “breasts” tenting out my nightie nicely.
We all went into the family room where we would sleep on the floor in our sleeping bags. Everyone wanted one more drink and we sat around like girl friends talking. The girls were all treating me like a girl, too. They dubbed me ‘Valerie’ and referred to me as ‘she’. It was all kind of nice. Since I felt completely spent, I wasn’t yearning for them to touch me and just being “one of the girls” felt good. It gave me a peek into girl culture as they talked about boys, what they liked, and didn’t like, about each of the guys in their crowd.
Predictably, I guess, the talk turned explicitly sexual. Before long, people were recounting the stories of when they lost their virginity, or (as they put it) had their cherry popped. I was surprised that every one of them had a story to tell. I guess from my experience and what I’d read, I just assumed that most kids our age were having oral sex but waiting a bit for the real thing. I was wrong.
At some point, one of the girls drew attention to me. They all started saying how sorry they were that I hadn’t had my cherry popped. I tried to laugh this off. I certainly had no intention of telling them that Jerry had popped my cherry. That would have been too demeaning in front of all of these girls. So I played the virgin. What was the harm in playing along, I thought. I said things like: “Oh, well. What’s a girl to do? I’m sure someday the right boy will come along.” They all laughed and I thought the topic was closed and we would move on to telling more stories about these girls and their experiences with boys. I was wrong.
Suddenly, Penny piped up and told us to “hold everything”—that she had a great idea. Penny ran from the room and came back holding something behind her back. “I know just want Valarie needs,” Penny said. Several of the girls went over to her and she showed them something. They squealed with delight at something I couldn’t see. Then the girls who were in on the secret came over to keep me busy while the others took a look. More squeal
I was really quite drunk at this point so I guess I was easy to manipulate. Two of the girls gently laid me back on my sleeping bag and began caressing me. They were lying on my arms, subtly but very effectively incapacitating me.
“Oh, you’re going to love this Valerie,” one of them said.
When I got a chance to see what was in store for me, I sincerely doubted that. Penny was walking toward me with a strap-on dildo—the kind that you see in porn movies on the internet. It was realistic, except for the size, which was bigger than any penis I’d seen in real life or on the internet. I remember wondering where Penny found this. (I learned later that she had discovered her parents’ store of sex toys and, apparently, they were into some kinky stuff.) But thoughts about practical issues like that were soon driven from my mind.
Penny told the girls that it was time that I became a woman and they should help me by taking off my panties. My bottom was soon exposed to Penny’s assault. To give her clear access, two of the girls held my knees up and spread them wide. I was rocked back so much that my asshole was almost sticking up straight for Penny to penetrate.
She slathered some lotion on the fake cock and, then, I felt it pressing against my asshole. It felt enormous—like it couldn’t possibly fit in me, at least not without doing major damage. But, as the girls cheered her on, the pressure from Penny was insistent. Before too long, I felt my asshole yielding. It didn’t happen easily, and it certainly didn’t happen without pain. But eventually, the head of the dildo had opened me and I could feel the back-and-forth motion of Penny fucking me. It actually crossed my mind that I should be grateful to Jerry for popping my cherry. This would have probably hurt a lot more if I hadn’t gotten an initiation on his cock.
The sight of the huge dildo pistoning in and out of my ass really got the girls cheering—and not just Penny. They were cheering me on as if this was an accomplishment of mine. I heard them say things about my not being a virgin anymore and about Penny really popping my cherry big time. As this went on, the pain receded. I didn’t think I was enjoying it but at least I wasn’t in excruciating pain anymore.
I say I didn’t think I was enjoying it because, I guess, at some level, I was. The girls soon began commenting on the fact that my dick was hard again. I hadn’t realized that; my attention was focused on the sensations in my asshole. I wouldn’t have believed it could happen. I’d already cum twice and I’d been hard much of the evening. But, I could feel it now. And when I looked at my crotch, I saw that, sure enough, my penis was standing at full mast. It wasn’t much, of course, but it was as big as it ever got.
The girls started arguing over who was going to get the next turn fucking me with the dildo. I don’t remember who won next dibs on my ass but I know that over the next hour, every one of the six girls had their turn fucking me and they took me in every position imaginable. I was fucked missionary style, doggy style, bent over a table, and riding the enormous dildo like a cowgirl. With the exception of a few times when I was being re-positioned, I stayed hard the entire time. And, by the end, I felt as if I really wanted to cum.
They wouldn’t let me, though. During all of this, the girls often touched my penis, but only to show each other how hard getting fucked in the ass made me. They never stroked me. And when I tried to stroke my penis myself, they stopped me. They told me that I was the girl here and this wasn’t about my pleasure. It was about me pleasing my man. Well, there wasn’t a man in the room. (Ooops, Freudian slip. I should have said, “other than me.) And I didn’t really see how I was supposed to please a piece of plastic. But it was clear enough that I wasn’t going to get any relief for now.
When the girls had tired of fucking me, they decided that I should be allowed to cum. I was looking forward to a hand job from one of the girls, or maybe a blow job. (I didn’t dare to wish for more than that.) But, as it turned out, I had to settle for a hand job from me. And they insisted that I do it while I fucked myself with the huge dildo.
I didn’t care. I wanted to cum so much that I would have done just about anything. I lay there, in my bra and nightie, thrusting the fake cock in and out of my ass while I stroked myself to my third orgasm of the night. Even though I’d cleared my prostate out twice already, I produced quite a bit of semen (for me). I shot it onto my stomach and some of it reached as far as my raised up nightie and bra. The girls had me smear my semen around on my stomach and then lick off my hand.
With that, the night’s activities were over. I fell asleep with my nightie sticking to the drying semen on my stomach. I suppose I should have slept fitfully after the sort of humiliation I’d been through. In fact, though, I slept like a baby.
I didn’t wake up until some of the girls were up and going. It was strange to wake up in the nightie and to feel my “breasts.” I went into the bathroom to pee and, when I saw myself in the mirror, I decided to strip off the girl clothes. When I looked in the mirror again, I guess I looked a little better. But it was strange to have bra marks on my body.
Leaving the nightie and bra in the bathroom, I went back out to the family room to get dressed in my clothes and get my things together so I could leave. As I walked into the family room, I was immediately sorry that I didn’t have the nightie, or at least a towel around me. The girls started talking about me and I quickly turned red with embarrassment. This made them talk more and, before long, I found myself sporting a very hard erection.
“Oh, look,” one said. “He has a morning woody.”
“More of a morning splinter, I’d say,” another corrected.
Some of them fondled my hard little dick a bit—not enough to get me off though. They just wanted to tease me for a while. Finally, they made me stick my finger up my ass and beat off onto the top of a cinnamon roll. That roll turned out to be my breakfast. But, once that little humiliation was over, the girls let me get my stuff together and leave.
On my way home, I wondered about how I should think of last night’s experiences. On the one hand, I’d seen, and been touched by six very cute teen girls. And, I’d had three orgasms in one night. Something I’d never done before. But, the cost had been extended humiliation and feminization.
* * *
I guess everyone’s excited about going off to college. But I was looking forward to it for special reasons. I was a very good student and had lots of options about where to go. I chose a small school, very far from my home town. More than anything, I wanted to go somewhere where no one would know me. I could start afresh. And I did.
Unlike most freshmen, I had a private room in my dorm. My parents had to pay extra for this, but I’d gotten a great scholarship and, so, it wasn’t costing them too much send me through a great school. My room had a private bathroom and I certainly wasn’t going to sign up for any physical education courses. So, I never had to shower in front of another person. This was going to be great! And it was. I loved my life here and I resolved that I was 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.
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.
He had been begging me since we met to take him out, dressed as a woman. At 6’3″, it was going to be a challenge to make him look like any kind of a lady.
She told him to lie on the bed, where she tied his arms and his legs to the bedposts. Her favorite position for him, face-up. He never knew what to expect when she did this to him. He couldn’t help but get an erection, his cock always got hard when he was around her, it was involuntary, uncontrollable. He did as told, spread his arms and legs and felt pure bliss and joy as the cuffs went on. He was going into her space, his space, subspace. Heaven on earth, is how he described it.
She didn’t crawl on top of him, placing her crotch or her ass over his face. She didn’t move over his cock, she slapped it, telling him to relax, this wasn’t about sex. She pulled a chair over to the edge of the bed and began painting his fingernails.
“Hold still,” she ordered him. “I am doing this once and once only. If you mess the polish, tough shit. This is all you get.”
“Yes, Mistress,” he closed his eyes and enjoyed the moments, each of them. Every minute spent in her presence meant another moment of happiness for him.
The light touches of the nail polish brush on this fingernails was strange. He could just barely feel it, he was accustomed to something stronger, harsher from her. No matter, he waited for something greater. A stronger touch, another swat on his cock or a slap across his face. These were his favorites. She was expert at delivering them and she knew how much he enjoyed her touch – in any form.
“Don’t move your fingers, they are perfect.” He stayed very still as she blew on his hands, his fingers, one by one, moving on both sides of the bed, climbing over his body, as if he were not there, naked, erect and excited.
She moved the chair to the end of the bed and began painting his toenails, occasionally using the crop against the bottom of his feet.
“Don’t fuck up the polish,” she screamed as his feet flinched each time they were hit.
She blew on his toenails, alternating breath with slaps on the bridge of his feet.
“Those will take awhile to dry. I’ll be back,” she yelled over her shoulder as she shut the bedroom door behind her. He laid there, naked, erect, and wondering what was next. He couldn’t help but wonder why she had picked now to paint his nails.
He waited and watched the sky grow dark. He didn’t fall asleep, but this was a meditative place for him. It was truly the only time in his life when he could completely clear his mind, turn it all off and just live in the moment. He was responsible for no one, only responsible for providing Mistress’ pleasure when she desired. That was the only reprieve he had in his life, the only break he got. She understood that and she made the most of it.
He didn’t know how long it had been when she reentered the room but she looked different than she had previously. She was dressed to go out – stockings, makeup and her hair was up and back, away from her face. This was how he liked her best, the lines of her jaw and her high cheekbones clearly visible. He still couldn’t quite believe what they had managed to work out between them, how well this worked for them both. He knew what he needed, he knew, in his heart, that he was a sub…he was a man who needed to serve a woman, a woman greater and stronger than himself but finding her had been a challenge. He had all but given up hope when they met. He had made a joke about spanking in one of their earlier conversations, and she had picked right up on it. At that point she had only received spanking, she had been dominated by a ruthless, selfish, arrogant man and she had shied away, not only from the D/s world but from men as a whole. He had jumped at the chance to bring it up, to discuss it, to see if he could interest her in switching sides, so to speak.
She had taken to it naturally, remarkable, really. Nothing about their relationship was simple or convenient but they both felt that it was what truly worked for them – anything else at this point would be a cheap alternative, filler, second best. They’d both had enough other relationships to know the bond they shared was real, vital, substantive.
“Are you going out, Mistress?,” he asked, wondering if he might have the chance to lick her pussy or suck her nipples before she left him there, wondering when she would come back, if she would come back. She liked that, to leave him. She liked the mystery and the power that it brought. He never knew when she returned if she would want to fuck him, be fucked or have him lick her clean of another man’s cum. That was an amazing experience and one that he relished. They had come so far together that she could ask nothing of him that would be too much, over the top. She was perfect for him, in every way. To the outside world, he was a macho, alpha male and she was the only person who knew what he truly needed and wanted. A woman he could worship, treat like a queen and who would not judge him. Their bond was exquisite and they both cherished it.
“Yes, I am going out and you are coming with me,” she replied. He looked surprised as she had just painted his nails. Where could they be going, he wondered.
She began to untie the restraints, instructing him to get up, get moving, it was late. He did as he was told. She lead him, by his cock, into the bathroom where she sat him on top of the toilet. Then she started to wrap his hair around a very hot curling iron. He flinched unsure that she was watching what she was doing. He hated burns and she had never taken that route with him.
“Oh, don’t be such a pussy! Women all over the world do this every day,” she scolded him. She continued to play with his hair, curling, teasing, spraying and then the makeup bag came out.
“Close your eyes,” she said as she applied the liner, the shadow and finally the mascara.
“So unfair, a man having eyelashes like that. Such a waste!,” she slapped his face as she spoke these words. “Good, bring a little color to your cheeks.” She followed up with some blush and then used the brush on the top of his chest, between his breasts. She also took the opportunity to squeeze and twist his nipples, causing him to cry out.
She smiled at him, kneeling in front of him, running her hands along his thighs. “Let me take a look at you,” she held his face in her hands. “One kiss before the lipstick goes on,” and he could feel his cock standing to attention. She noticed as well and she lifted her skirt and slid her slick pussy down onto it.
Oh, god, she felt so good, so warm, so wet. She didn’t move for a long time, just stared into his eyes, smiling. “You make a beautiful woman, albeit, a woman with a hell of a cock but a woman nonetheless.” She kissed him again and then her cunt muscles went to work on his cock. How she did that, he would never know. She was barely moving her body and yet, yet, her pussy was swallowing his cock whole. Causing him to shudder and spasm. She began to ride him, in earnest, and he could see that she was coming closer and closer to reaching a climax.
He began to push up against her, trying to create some friction so that he could come with her but as soon as he began to move, she stopped, slapped him hard, first across the face, then around his chest. “Do not move a fucking muscle, understand me?,” she whispered into his ear.
He nodded and sat quietly as she, again, rode his cock, harder and deeper, using her muscles to drive him crazy with lust. When she came, it was unmistakable. The cries which grew louder and closer together, the gush of juices that came out of her, the flush of her cheeks and her chest. He had never known a woman to come with such abandon, with such flourish. He loved it, he lived for it.
When she recovered, she told him to purse his lips and she applied a bright red lipstick. “Go look at yourself as a woman, in the mirror. You look pretty damn good, if you ask me. I mean, you could never pass as a woman, but that will be half the fun,” she smiled at him, knowing that the thought of being caught, dressed as a woman, in his own community was a fear of his.
She went into the bedroom and came back with a small g-string panty, clearly made for a woman about half his size. “Put these on,” she instructed, knowing that his cock was still hard and wet from her orgasm, when she had refused to allow him to reach any sexual satisfaction.
“Now, this,” she said, holding out a dress that was black and long. “Oh, wait, you’ll need a bra and some fake boobies,” she told him, tweaking his nipples again. “Maybe a little rouge for your nips?”
“Yes, Miss, please,” he couldn’t believe that he was finally getting his wish. Of course, he expected her to do this in a town where he didn’t know anyone. He would never be able to hide behind the dress and the makeup. He could only hope that he wouldn’t run into anyone he knew.
When dressed in a bra and panties, his erection still evident, she turned him around to look at himself in the mirror. “Pretty ugly sexy, don’t you think?” she teased him.
“Yes, Mistress, as long as you are pleased that is all that matters to me,” he answered, looking down. He couldn’t believe how hot this was, how turned on he was.
“Raise your arms into the air,” his mistress instructed and she slid the dress down over his broad shoulders and newfound breasts. The dress felt silky and soft against his skin but he waited for her instructions before looking at his reflection again.
“Put these on and your shoes are by the bed,” she said, tossing him a pair of pantyhose in an extra-large size. “Lets hope these can help hide your erection. If not, I am going to have to beat it out of you. Now go put on your shoes, then come back in for another full-length glance at yourself.”
The red pumps with 3″ heels fit perfectly but maneuvering his large frame on them would take some getting used to but he made it into the bathroom without falling and when he looked at himself, it took a moment to believe that it was really him.
Tall, beautiful eyes, his silver hair looking like he had just stepped out of a beauty salon. The dress fit him perfectly, just the right length, covering his knees and the red shoes completed the outfit. He caught her eye in the mirror and they both began to giggle. Laughter was the thing that they always could rely on, finding the same things humorous, making jokes to alleviate some very awkward situations – laughter had been a glue for them in the beginning.
“If I didn’t know you, I’d want to fuck you,” she whispered into his ear. “Hell, I do know you and I can’t wait to fuck you,” she added, grinning from ear to ear.