My Sexual Odyssey Part 2 Becoming a Slut
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After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet at times like these; I have no idea how I would have learned about these things without being able to go online.
I found a bar which appeared to cater to the LGBT community in general. That sounded relatively safe, but as I had never before visited such an establishment, I wan’t sure just what to expect. Would I meet anyone there who knew me? Would I stand out like a sore thumb? What was I supposed to do when I got there, anyway? As usual, I hesitated, panicked, and had second, third, and fourth thoughts. Nonetheless, I was resolved to go, and go I did.
That Friday evening, as I approached the bar, I felt completely out of place. I was wearing street clothes, as I was nowhere near comfortable enough to go anywhere “dressed”. How would I find what I wanted if I couldn’t even dress the part? I had no clue. As I walked in, I expected everyone to look at me. No one did. This calmed me down a bit. I looked around, spotted an empty booth, sat down and wondered if I should approach the bar to order a drink, when someone came over and asked me what I would have. I ordered something simple, and the waiter disappeared. As I looked around, I saw men talking with one another, but detected no signs of sexual activity. Well, what was I expecting, sex on the floor? The waiter reappeared with my drink. I began to wonder if this was a good idea; I mean, what was supposed to happen? It seemed as though nothing would. I was becoming annoyed, and I decided to finish my drink and leave. This had been a waste of time, and I had put myself through all that anguish for nothing.
Just as I emptied my glass, the waiter came over and placed another drink in front of me. I said, “I didn’t order this.”
He replied, “It’s from that gentleman at the bar.” I looked in that direction, and someone smiled at me. I just smiled back, and thanked the waiter. Now what, I wondered. I didn’t have to wait long for my answer. The guy at the bar came over, smiled, said, “hi”, and asked if he could join me. I motioned for him to sit down.
“You look uncomfortable. Is something wrong?”
“Well, I’ve never been here before, and I don’t know anyone here.”
“My name’s Tom.”
“Hi Tom, I’m Tracy.”
“That’s a pretty name. You looked so sad and lonely all by yourself I wanted to try to cheer you up.”
“Why thank you Tom, that was very sweet of you.”
“Not at all. What made you come tonight?”
“Oh, I was just hoping to expand my social life a bit.”
“Hmmm. And just what were you hoping to find?”
Oh, great, now I’ve got to put my cards on the table. What am I supposed to say?
“Well, I was hoping to meet up with someone who wants to meet someone like me.”
“And what would that be?”
Shit, this guy goes right to it. Now what?
“I’m not sure how to...”
“It’s okay, you don’t have to be too open about it. Could I just tell you what I’m looking for instead?”
“Yes, of course.”
“I’m sure you know what kind of a bar this is, right?”
“Yeah...”
“Well, it is frequented by all manner of people, looking to hook up with all types of people. As for me, I like sweet little girly-boys, who like to dress, and I was kinda hoping someone as petite and demure as you might be that. Am I wrong? If so, I apologize. I certainly wouldn’t want to offend or upset you.”
Oh fuck, I thought, how did he know? I can’t say no, but if I say yes, I would be committed to doing something, probably right now, and while he certainly was nice enough, and cute, as well as masculine, I just wasn’t sure.
“I suppose I have to be honest. Yes, that is what I am or like or want, but I am still having a hard time adjusting to my own desires.”
Holy shit, did I actually tell him that? I did. God, now what?
“Would you care to talk about this with me?”
“I don’t know; maybe.”
“Well what exactly is the problem?”
“I like dressing, and I enjoy what I do when I am dressed, but I’m not sure I can say ‘yes, this is what I want to do, how I want to be’, from now on.”
“Let me ask you this. Do you like feeling pretty?”
“Yes.” I was feeling pretty embarrassed at this point.
“Do you like it when someone says you’re pretty when you’re dressed?”
“Yes.” I was feeling almost naked now.
“Do you like it when you feel wanted, desired, lusted after?”
I just nodded my head.
“Does it make you feel sexy?”
I nodded again.
“How does it make you feel when you are touched, caressed, and treated like a sweet girl?”
“Where is this going? I mean, what do you want me to say?”
“Please, calm down, I don’t mean to hurt or upset you; I’m only trying to help. You see, if none of these things bothers you, if instead, they excite and please you, then it’s not the cross dressing that’s the issue.”
“Okay, so what then?”
“Could I ask you something? You don’t have to answer if you don’t want to.”
“What?”
“When was the last time you had sex?”
“A couple months ago, why?”
“And before that, about how long?”
“Maybe the same.”
“I think I know what the problem is.”
“Oh? What?”
“You have never given this lifestyle a fair chance--you’ve never really given yourself a chance to feel comfortable with this side of your being.”
“So, what do you suggest?’
“You’re going to think I’m merely trying to get into your panties.”
“I don’t wear any, but go ahead.”
“Nice! But what I think you need to do is to consider having sex, preferably while dressed, on a fairly regular basis, at least for a few weeks, to see how you like it. If you still feel uncomfortable, that’s one thing, you can always stop. But if not, you might be a lot happier than you are now. What have you got to lose?”
I had to admit he had a point, even if he was volunteering to be that regular sexual partner. And what did I have to lose, anyway? My virginity? That ship had sailed. My inhibitions? My fears? If so, wouldn’t that be a good thing?
“Okay, let’s say you’re right. What should I do, exactly?”
“It’s a lot easier than you expect. Just choose someone with whom you feel as comfortable as you can, someone who seems safe, and tell him what you want. I gaurantee you you will have no difficulty finding a volunteer. It doesn’t have to be me, but it does have to be someone.”
“But how often are you talking about?”
“At least once a week, preferably two or three times, but no more that, at least not at first. You don’t want to get burned-out, or over-worked.”
“I see.”
“Could I make a suggestion?”
“Sure, what?
“Go home, think about this, and if you want to try it with me, give me a call or send me an e-mail. Here, I’ll give you my telephone number and e-mail address.”
“Okay, thank you.”
“I’ll take off now, and I hope I hear from you. But even if I don’t, please try what I suggest, otherwise you will keep on needlessly tormenting yourself.”
“Okay, thanks.”
“Bye Tracy.”
“Bye Tom.”
Well now, that was something! I gulped down what remained of my drink, and walked out into the crisp night air. It felt good, yet somehow dampened my ardor, albeit only temporarily. I knew what he said was true, even as he said it. There was nothing to consider, really. It was only a matter of putting it into practice. But would I have the guts?
When I arrived home, I realized that my goal of “hooking up” with some guy both did and didn’t happen. I had to admit, he didn’t push it. That was a good sign. I went to bed, alone, sexually unsatisfied, realizing that this would continue if I failed to do what Tom had suggested.
The next day I awoke with butterflies in my stomach. I knew what I had to do, but the courage and resolve of the previous night had disappeared, and in its place, the old anxiety had filled the vacuum. I forced myself to do what had to be done, and, despite much trepidation, called the number on the crumpled napkin.
I heard a familiar voice. “Hello?”
“Hi, Tom?”
“Yes, is that you Tracy?”
“Uh huh.”
“I didn’t expect to her from you this soon. I wan’t sure if you would even call at all.”
“Me neither, but I knew I had to do it. You were right last night Tom, and I want to thank you for your kindness.”
“That’s so sweet of you to say Tracy honey; what would you like to do?”
I just melted inside when he said that. Why? It just made me feel so soft and feminine, and I liked the feeling. I just wasn’t sure if I liked that I liked the feeling.
“Well, I think I should do what you suggested, and I don’t know anyone whom it would be better to do it.”
“I’m so flattered that you feel that way.”
“So, I don’t know how to begin exactly, I mean....”
“It’s okay sweetheart, we can take it slowly.”
Christ, that ‘sweetheart’ crap really does it to me. Fuck!
“So honey, when would you like to get together?”
“Tomorrow is Sunday--would that be okay?”
“Of course baby doll, that would be fine. Where would you like to meet?”
“I think I would be more comfortable here, at least at first.”
“Of course. Do you want to tell me where to come?”
“Right.” Then I gave him my address, and we agreed upon a time, and hung up. Fuck. I was completely committed now, no getting out of it. But it’s what I want, isn’t it? Well....yes and no. We’ll see. And how we’ll see. Oh boy.
The day dragged by, and I felt aroused, frightened, excited, upset with myself for feeling excited, and generally exhausted from the energy that all this was using. Finally night came, and I went to bed early so I wouldn’t have to obsess over this anymore.
The next morning, I awoke with a feeling of dread. Why? I wanted this. I asked for this. I needed to do this. I think the knowledge that I had made a potentially life-changing decision was what concerned me. Oh well, too late now. I got up, forced myself to eat something to keep my strength up, then prepared for my date. I won’t bore you with the usual descriptions of removing hair, or how sensuous it feels to put on nylons: those of us who’ve dressed already know, and those who haven’t need to find out for themselves.
So what to wear? I think a little black dress, with black suede shoes, matching stockings, gold hoop earrings, and a velvet choker would do nicely. As the appointed hour approached, I began to relax; since I was all dressed up and ready to go, there was nothing more to do but wait. I didn’t have to wait long. Tom arrived right on time. He even brought some wine. How thoughtful!!
“Hi,” I said nervously.
“Hi Tracy, how are you?”
“Okay, a little nervous, I’m not sure why. Please, come in.”
“Thank you.” He handed me the wine, I took it into the kitchen. Tom followed.
“Would you like me to open it for you?’
“Please.”
As he deftly removed the cork, I retrieved two glasses.
“Care for some now?”
“Yes, thank you.” He poured some for me. I needed something at this point, and it tasted good besides. He took my hand, and led me over to the couch. I sat down, he sat beside me. He continued to hold my hand, gently caressing it. This was nice.
“So, what, I mean, how, er,” I mumbled. At this point Tom pulled me
toward him, and kissed me softly on the lips. I trembled with anticipation. He kissed me again. I kissed back, then parted my lips, hoping he’d take the hint. He did. I sucked on his tongue like a hungry animal. He said,
“Take it easy!”
“I can’t,” I replied.
“I don’t want to rush you.”
“It’s not rushing if it’s what I want, right?”
He stood up and, holding both my hands, guided me to my feet. Then he took me in his arms, while kissing me on the neck. I thought my knees were going to collapse.
“Tom please. I’ve been anticipating this for days; let’s go?”
Wordlessly, he escorted me into the bedroom. Then, oh so gently, he began to undress me. I was so hot by then I couldn’t stand it. I cupped his cock and balls; he seemed to like that. Finally, I felt a little in control!
My dress fell to the floor. Tom slid my panties down; they fell to my ankles, then joined my dress as I stepped out of them. I fell back on to the bed. Tom quickly undressed, then lay on the bed beside me. As he kissed me again, he began to move down to my neck. I wondered if he would suck on my nipples, but instead he parted my legs, and kissed and caressed my inner thighs with his tongue. I almost came right then and there. His cock was already hard, so I told him I wanted him to cum in my mouth. He appeared surprised by my boldness, but not displeased.
While he lay on his back, I moved into position, then kissed the mushroom head of his beautiful cock. He responded nicely, and I felt gratified, so I licked its full length, slowly, teasingly, then back down again. I kept doing that, only after he was beside himself with desire did I finally take it in my soft, warm, wet mouth. I just held it there, motionless. Then, ever, so slowly, I began swirling my tongue around it, all the while keeping its full length, or most of it, in my mouth. I just loved this; I could have kept it up all day, in both senses of the term.
As I caressed the underside of his glans, he began to moan, writhing in response to my ministrations.
“Oh God, I can’t believe this, you’re amazing!”
“Oh, everyone tells me that. You’re all just being sweet!”
“Like hell! I’m telling you, you are one in a million.”
“Well, I like what I do.”
“Me too. Please please don’t stop.”
I stopped.
“Are you sure? I mean, I wouldn’t want you to get bored or anything.”
“Oh God, you’re killing me!”
“Well, I wouldn’t want to do that. Maybe we should do something else then. Want to watch TV?”
“For God’s sake!!”
“Hmmm? You want something?”
“ Please .”
“Please what?” I asked, all innocent-like.
“For the love of God Tracy!!”
It’s funny how sex seems to elicit expressions of religiosity from people, isn’t it?
“Okay, okay.” I went back to ‘work’.
I started to pump, up and down, pulling out from the tip with a slurppy “pop” as I sucked as well as pumped. This about drove him to distraction, which only excited me more, so much so I actually came before he did, without either of us even touching me. He was too preoccupied to notice.
As he began to buck, I knew my reward wasn’t far off. I just kept varying my routine, and waited. I didn’t have to wait long. As he lost all control, he came in firm spurts, and the warm, sweet, ambrosial liquid flooded into my waiting, eager mouth. I swallowed, as I always do, and savored the multiple blasts.
I sat up. Tom looked spent; spent, but happy. I lay down beside him, and he clasped me in his arms, and kissed me on my head as we cuddled for an indeterminate amount of time. I held his now supple cock in my tiny hand.
After a while, it began to stir back to life, and I gently kneaded it to its full extent. Then I kissed him on the stomach, licking and caressing with my lips and tongue. I moved down, but skipped his cock and balls, and went to his thigh, as he had mine, just above the knee. Using my tongue in the same way, I moved ever so slowly up to his balls, but before reaching them, moved back down again. I repeated this a few times before moving to the other leg. If he was hard before, he was positively rigid now.
I asked him if he would like me to suck on his cock again. He didn’t say anything, but the expression on his face said it all. I repeated my earlier activities, this time stopping short of allowing him to cum. I had other ideas, and apparently so did he. He exchanged places with me, reached for some lubricant I had on the nightstand, then adroitly and gently prepared my already waiting ass-pussy. He parted my legs, placing them on his shoulders, then slowly, sweetly, entered me.
I was at peace. He just held it there, not moving for the longest while. When I could stand it no longer, I said, “Tom, please.”
“Please? Please what?”
Oh fuck, he was paying me back now. Great.
“Oh come on, don’t make me wait.”
“Okay, I can’t do that to you after what you did for me.”
“Thank you.”
With that, he commenced pleasuring me, slowly, gradually building to a crescendo of passion, stopping when it appeared I might cum, only to begin again, then stop, then begin. I don’t know how long this lasted, but eventually I did cum; and how I came. I thought he had too, but no, he just paused for a bit, then resumed fucking.
“Holy shit, are you going to continue?” I asked.
“Yes, we’re just getting started. You need to find out just how horny you can be, and how passionate.”
“Just getting started? What do you mean?”
“You’ll find out soon enough. Just lie there and relax; I’ll take care of the rest.”
And, he did. Half an hour later, he was still at it. No one had ever gone that long with me before, and he didn’t even seem tired. What did this man eat?
I felt the familiar upsurge of desire and arousal, and to my surprise, experienced another pulsating orgasm. I figured that was it, no way I could cum anymore, and no way he could keep fucking me. Boy was I wrong; wrong on both counts.
I started to feel like I was going to cum again; I told Tom I didn’t feel like I could take any more. He just ignored me, and said he wan’t going to stop anytime soon.
“Don't keep fighting it--"
"But I'm not a woman!"
"No? You may not have the body of a woman, but you sure have the desires of a woman, the feelings of a woman, the reactions of a woman, the responses of a woman. You dress like one, smell like one, act like one, and have a smooth, slender, petite body like one. There's more to being a woman than having a pussy. Psychologically, and in your behavior, your passions, you're more woman than most, believe me! You suck cock like one, and you let me fuck you, just like a woman. Face it, you've got a woman’s figure and a woman’s emotions. You like dressing up in girly clothes, and you look fucking good as a girl. Why don't you just cut the crap and, more to the point, accept that you are a woman, at least in part.”
"I don't know, I--I...."
"Tell me you don't like this!"
"I can't."
He was almost assuredly right. I was, in my actions and reactions, and to all appearances, a woman, at least at times, and to some extent, but my pride resisted that admission. However, there's no point in fighting it. What happened, happened. You can deny the facts of reality all you like, but that won't make them go away, will it?
We had now been at it for a good hour and a half, maybe more, and he was still fucking me. He had re-lubricated his cock, so as not to injure me, but he went at it like he hadn’t had sex for months. He picked up the pace, and as he sensed my growing excitement, he accelerated his fucking to a fever pitch, pounding me hard and long. I loved it. When I couldn’t hold it any longer, my body convulsed in uncontrollable spasms. I thought I’d never stop cumming. I couldn’t believe how hard I came, or how long. Tom came too, as I could feel his warm cum lave my now gaping ass with profuse torrents of liquid lust. I glanced at the clock. We’d been fucking for two hours and fifteen minutes.
Eventually we recovered enough to get up. We showered, separately, as I didn’t want to spoil the illusion by removing my hair in his presence. I then fixed us a snack while he showered. As he re-emerged, I said, “Well, that never happened before!”
“The multiple orgasms, or the two-hour long fuck?”
“Both.”
“Well, there’s more where that came from.”
“I don’t know if I can handle more!”
“I don’t mean tonight, but another night, and soon. Remember, you agreed to do this on a regular basis for a while, right?”
“Why yes, of course. I just didn’t expect it to be so.....”
“I know. But that’s because you never gave it a chance. You never gave yourself a chance.”
“Okay, so when?”
“Well, today is Sunday. You should rest and recuperate a little while, but not too long, or you might want to go back to doing nothing again. How about Wednesday?”
“Okay, Wednesday it is. Want to come here again?”
“Yes, I think it would be best; you need to feel as comfortable as possible.”
“Okay, here on Wednesday. Great.”
We finished eating, then embraced, he squeezed my ass affectionately, then departed.
So, what to make of this? I just had the longest, most intense, most orgasmic sexual experience of my life. Now what? What did it all mean? Did it have to mean something? This was just too much to sort out like that. I did feel calm, relaxed, satisfied, and kind of all warm inside. I was tired, so I went to bed early, although I had to change the sheets first.
The next morning I awoke feeling rested and serene. I took the day off from work, and spent the day doing nothing in particular. I washed some sheets, (!) ate a little, listened to some music, and thought about the previous day’s activities. I felt good about them, and good about myself. The following day, I found myself looking forward to Wednesday. I couldn’t do any work, I just went through the motions. I felt horny. I wondered how that could be; after all, it was only two days. Nevertheless, I was. I went home early, and since I had taken Monday off, it surprised nobody. I found myself fantasizing about sex all evening.
Wednesday morning, I decided to focus on work. I tried, really. But all I cared about was getting fucked again. The evening couldn’t come soon enough. When I finally got to go home, I immediately showered, dressed, and waited. I couldn’t even eat. After what seemed an unendurable wait, Tom arrived. I practically assaulted him. If he hadn’t been prepared to have sex right away, I swear I would have exploded. Fortunately, he was not exactly adverse to the idea. I won’t detail the evening’s activities, as they were substantially the same as those already described, and I have no desire to be redundant. Suffice it to say that the evening disappointed neither of us.
This pattern repeated itself a couple of times more over the course of the week. We met again on Friday; this time it was only two days between dates; then again on Sunday. On Monday, I called and told Tom I didn’t want to wait until Wednesday or even Tuesday; I wanted him right then.
He was there in twenty minutes.
“So, tell me, were you nervous?”
“When?”
“Today.”
“Over what?”
“My coming over.”
“No, why would I be?”
“Didn’t you tell me that you always got nervous when you were meeting someone for sex?”
He was right, I always did. But lately, I hadn’t; not since our first date.
“Hey, how about that! I felt excited, adrenalized, but not anxious. Wow! I guess things have changed a little.”
“I’d say a lot. Inside of a week, you’ve had sex four times in eight days, as opposed to four times over the course of maybe a year or more.”
“Holy shit! You’re right! What the hell’s happening to me?”
“I can tell you. You finally got in touch with your inner slut.”
“Oh come on! That sounds cute, but it’s really silly!”
“Is it? Just think about it. It’s a psychological fact that the more sex you have, the more you want. It’s like an addiction.”
“I guess I do want it more. It does sort of feel like an addiction.”
“It’s true. You get a dopamine rush, and this is bio-chemical, not imaginary.”
“So now I’m a sex addict? What does that mean, that I’m going to be some sort of nymphomaniac?”
“Going to be?” Look at yourself, you have had more sex in one week than in the past two years, and you still can’t get enough.”
Shit. He was right. What was happening, what has happened, to me? Where was this going? What would the outcome be? Is there more to come? I shuddered at the idea that I could be so out of control, so driven by my desires. But hadn’t I been all along? The only difference was that while before, I was resisting them, now I wasn’t. But at least before I had some measure of control, in between bouts of extreme lust; now, it was fast becoming a lifestyle, if it hadn’t already become one. On the other hand, before I was miserable, and now I was content, ecstatic even.
“I’ve got to process all this. I need some time.”
“So, no sex?”
“I didn’t say that. Let’s not go crazy!”
“Okay.”
So, yet again, we spent the next few hours slaking our, or at least my, seemingly unquenchable thirst for raw, uninhibited sex. I regretted none of it, but I did have to reflect upon the significance of all this. The next day was a holiday, so I had no distractions. I spent the holiday looking at how far I came in just a little more than a week, and in wondering how it would end.
In addition, I pondered the impact of all this upon my sexual identity. After all, when not dressed, I still had masculine desires, masculine lust for women. Wouldn’t this erode, even destroy, my manhood? It turns out that terms like homosexual and bisexual were only coined in the 19 th century. It seems that in ancient Greece, men and women both had same sex lovers, yet were not classified in the same terms we employ. In Rome, it was considered normal for both sexes to be sexual partners, and so it was actually expected. Only the social status of the participants determined whether the alliance was considered acceptable.
I read about the Kinsey scale, with exclusive homosexuality at one end, exclusive heterosexuality at the other, and most people falling somewhere along the continuum, with bisexuality in the middle.
I then found the Klein scale, which was more complex, as is human sexuality itself. In it, to whom you were attracted, about whom you fantasized, as well as with whom you had sex, were all dimensions that were included, as well emotional preference. This made sense to me. I have no interest in viewing images of men, nude or otherwise, whereas I love photographs of hot women. Same goes for strippers: women, yes; men, no.
Similarly, emotionally, I have always and only fallen in love with women. The same goes for kissing: only women, despite that first experience with Tom. I suspect I was carried away by the drama of being seduced. So all romance for me, whether fantasy or real, has been with or about women. But my sexual fantasies and activities have included both. So okay, I’m bisexual then; no news there.
I dislike those who go through life parroting the cliche, “I don’t like labels.” How else do you tell a can of beans from a can of peas? Such people simply don’t want to confront the consequences of clear identification, or are unwilling to take the time and trouble to attain that clarity. One must also avoid the other trite platitude: “Everybody’s bisexual.” If what they mean is that the potential for same sex arousal and activity exists in everyone, that’s one thing; but that simply isn’t how the word is used. What people mean is what one STD counselor asked me: “Do you have sex with women, men, or both?” She didn’t care about my romances, my fantasies, or how I categorized myself; all she cared about was what I did and with whom. So “bisexual,” the way most people employ the term, means precisely that, having sex with both. Trying to call everyone that is as stupid as those, usually exclusively homosexual men, who try to deny the very existence of bisexuality. The fact is, many of us like both. Deal with it.
Someone reading this may be saying to themselves, “Bullshit. This pervert is just rationalizing, trying to normalize his predicament.” I am not contending it’s “normal”, if by that we mean statistically; I am merely stating historical, psychological, and biological facts, which means it is natural, and occurs across virtually all species. As to what is “natural”: wearing clothes is “unnatural”; flying is “unnatural”; wearing glasses or contacts is “unnatural”; oral or anal sex even between a man and a woman is “unnatural”. The fact is, human behavior in general, and sexual activity in particular, enjoy a certain plasticity, arising from the human capacity to transcend hard-wired behavioral programming.
Neither do I argue that all dislike or disapproval is attributable to “homophobia”; yes, some of it is, especially when people become absolutely enraged by it. I too dislike those mincing, plumed and sequined denizens of gay pride parades, with wobbling heads, glazed eyes, and voices like Richard Simmons. But I’m not enraged by them, they just repulse me, and they would even if they were straight.
So what about the cross-dressing then? Some CD’s are straight. That surprises and mystifies me. What’s the point? But it’s okay, they’re not hurting anyone. But for me, it is an expression of my female side, a way of getting in touch with it. It seems to make more sense that, if you’re going to experience the joys of having sex with as a woman with a man, then you might as well get as close to that experience, and that side of yourself, as possible. This is why getting a blow job from a man, or fucking one, doesn’t appeal to me: I can do that with a pretty woman, so why some (to me at least) sexually unappealing guy? Of course a beautiful “she-male” is another thing entirely. And then there are transexuals, who get or want to get a sex change operation. Let’s face it, sex is just not all that black and white. It is funny though, how men who only take the “active” or “male” role when having sex with other men, continue to tell themselves that they are straight. They may not be gay, or even bi, but they still seek sex with men, and that’s not exactly inflexibly straight.
Even where bisexuality, transsexualism, and related topics are not an issue, the genetic, hormonal, and anatomical aspects of embryology are enormously complex. Human embryos are the result of fertilization of an ovum by a spermatozoan. Eggs are gender neutral; however, they all contain an X-chromosome, and no Y. If the father contributes another
X-chromosome, the fertilized egg, now a zygote, will, under normal circumstances, become female; if he contributes a Y, male. However, not all embryos contain XX or XY chromosomes; some are XXX, some XYY, and I’ve even seen XXXY, which produced a classic “she-male”.
Some XY individuals have external genitalia that develop to look female, and other XX individuals whose external genitalia develop to look male. Different combinations give rise to different outcomes. In addition, different hormonal secretions result from these combinations. The amounts of the male or female hormones produced will alter the anatomical structures, despite the mere genetic aspects. Hence, development in puberty will not always be in complete accord with the chromosomal determinants.
Tissues that create the male genital components create the equivalent components in females. The tissue that forms the penis in males will form the clitoris in females, and the tissue that forms the scrotum will form the labia majora and minora in females. Males also have nipples, which implies less sexual dimorphism than is generally supposed.
The result of all this is that the simplistic sexual or gender bifurcation contemporary society imposes upon us is at variance with scientific fact, as well as informal observations of human behavior: we are more complex than that.
A couple days later, Tom called to see how I was. I told him I was fine, and asked when he would like to come by. He said anytime, so I suggested that evening, to which he agreed. He also asked me to wear some sort of nightie, so I selected a baby-doll top with matching bottom, the black velvet choker, and nothing else. I felt naked, but that was a good feeling.
As usual, Tom was right on time. I could tell he really liked the baby-doll nightie, and so I decided to just dropped to my knees and suck his cock right then and there. He resisted my efforts, but I prevailed in the end, and he exploded into my mouth. This time I guided him into the bedroom. We lay down beside one another, me on my tummy, him caressing me gently. He began kissing me on the back of my knee, then worked his way down rather than up, eventually kissing me on the bottom of my foot. This felt wonderful and sweet. Tom then gradually worked his way back up, eventually giving me the longest and best rim job I ever experienced. After he nearly drove me crazy with desire, he fucked me from behind, with my bottom raised as I lay on a couple of pillows. This time he fucked me hard and roughly, pounding me into sweet surrender. I don’t know how I am able to cum without any genital stimulation, but cum I did; however, before he came, Tom pulled out at the last moment and came in my mouth for the second time that evening. We then collapsed in satisfied tranquility.
The next day Tom called and said he had something to tell me. I felt worried and anxious. I asked him what, and he said he would discuss it when we met. Great. Don’t you just love it when someone holds a thing like that over your head, then keeps you wondering when the other shoe is going to drop? So I agreed to meet him, and I joined him for a cup of tea.
“So what’s wrong?” I began.
“Nothing, just relax. I just wanted to tell you that I think you are ready for the next step.”
“Next step? What next step?”
“I want to take you to a t-girl club this weekend.”
“Okay, so what’s the big deal?”
“I want you to go dressed.”
“What?! Are you kidding me?! I’ve never gone out dressed! I’ve only dressed in private. You can’t be serious!”
“I am serious. I think you need to do this.”
“No, I really don’t. I’m just fine with the way things are. Really!!”
“I know that, and that’s the problem. You get into your comfort zone, then you don’t want to stretch. I think you need to find out how comfortable you can be en femme , and interact with others like yourself, as well as male admirers you will meet.”
“I don’t know Tom. That is really scary.”
“What’s there to fear?” Everyone there will be like you, or will be looking for someone like you. And besides, I’ll be there with you. So what’s the problem?”
“Well, I dunno, maybe it will be okay, it’s just....”
“I know I know. It’s just a matter of getting used to it. However, it will be late, we can go around midnight. They’re open until four in the morning. I’ll drive us, so you only have to walk from the car to the club, and they have a parking lot.”
“Well, maybe....”
“Oh come on, be a brave girl!”
“Oh shit, why do you have to talk to me like that? You know it makes me melt inside.”
“I know, and that’s why!”
“Great. So I’m that easy to manipulate?”
“Not really, just easy to fuck.”
“So is that why you like t-girls and CD’s more than genetic women?”
“In part, yes. You’re both hornier, easier to bed, less inhibited, and don’t need or want the melodrama. You don’t make demands, we don’t have to jump through hoops in order to fuck you, or wonder if we’re going to have sex with you when we do get together. You don’t ever say you don’t like oral sex, or you don’t swallow, or you don’t do anal sex.”
“But what about a woman’s pussy; don’t you miss that? I mean, I still enjoy the fragrance and flavor of a woman.”
“Your ass is tighter than any pussy, you don’t get pregnant, and you’re never ‘on the rag’. On top of all that, you give better head. We can be honest about what we want, and we don’t have to put up with all the bullshit. With genetic women, the fucking you get isn’t worth the fucking you get. They’re moody, and always upset over something. You’re not oversensitive, and not so easily hurt. You’re not nagging, complaining, clinging, irrational crybabies. Also, you’re not timid and risk-averse. You’re simply better, in bed and out.”
Wow. I never heard that before. But, I can see it. All this time I thought I needed to study women in order to replicate the experience, whereas maybe women have something to learn from us. Amazing. Christ, what a week. What an adventure. And we weren’t finished yet.
“Okay, so this is Wednesday, when are you suggesting we go?”
“Friday or Saturday. Have you a preference?”
“Not really; I’ll be petrified in either case. Let’s just get it over with, the sooner the better.”
“So Friday then?”
“What time?”
“I’ll come by around eleven, that way we can take our time.”
“Sounds good. What should I wear?”
“Whatever you feel comfortable in. You look hot in everything I’ve seen you in so far.”
“Well, I don’t suppose I can wear a nightie or bustier!”
“Don’t be too sure. I’ve seen some surprising outfits there.”
“Oh boy, this is gonna be weird!”
“You don’t have to do a thing. We can just sit and drink if you like, watch other people, dance if you want to, whatever.”
“Okay. I’ll see you then. Bye bye.”
“Bye sweetheart.”
Oh fuck! This is huge! It’s one thing dressing at home, or for a sex partner, but out in public? Oh my God!
At least I have the advantage of being 5’ 7,” 129 pounds, with refined features and a petite figure. I only wear a size seven and a half men’s shoe, which is nine for a woman’s shoe. You’d think that the numbering system would be the other way around, making a woman’s foot smaller. Of course in Europe the sizes are all completely different for both. In addition to having soft features, I have no hair on my chest, back, ass, or even underarms, and I only need to shave my face every three days. The hair on my arms and legs is extremely light, so that’s a help too. I have no tattoos and nothing pierced. Men seem to like that.
So okay, I needed to plan this. I decided on a hot slit-skirt with a cute top, black stockings and boots. The boots would be easier to walk in than pumps, and yet they still look feminine. This was going to be exciting.
Well, the days dragged on, and of course, I felt the usual anxiety I experience when confronted with almost anything new. As Friday arrived, I became even more nervous. I wanted this over with. I began to prepare for Friday night.
As the appointed hour approached, I dressed, had a glass of wine, and waited. Just after eleven, Tom arrived. I opened the door, and told him how frightened I still felt. He gave me a nice hug, and assured me everything would be fine.
“Are you ready to go?”
“No!”
“I know, I know, but you need to relax, it will be fun, really.”
“Okay, let’s go then. I can’t stand any more of this waiting around.”
“Sure, come on.”
I walked out of my apartment dressed as a woman for the first time in my life. Fortunately, it was late at night, and no one was around to see me, but since I was passable, it really wouldn’t have mattered even if they had. Still, it being my first time and all, I was not able to take much comfort in that.
*
I have received many responses from readers of the first part of My Sexual Odyssey, thanking me for elucidating issues with which they’ve been confronted, as well as giving voice to feelings that they have experienced. I am gratified if I was of any help. This is a continuation of Part I, and is incomprehensible without reading it first. There are hotter stories on Lush, more beautiful stories and poems on Lush, but I doubt that anything is as autobiographically truthful. There are no women with mischievous grins, immediately eager to feminize me; no sales women who wickedly wink at me, then want to have sex in the changing rooms, and no cocks as long as your forearm and as big in circumference as a beer can. The world’s record is thirteen and a half inches, and I’ve never encountered anything greater than nine inches, and don’t want to. So, if you want wall-to-wall sex with no story no truth and no content, look elsewhere.
I found a bar which appeared to cater to the LGBT community in general. That sounded relatively safe, but as I had never before visited such an establishment, I wan’t sure just what to expect. Would I meet anyone there who knew me? Would I stand out like a sore thumb? What was I supposed to do when I got there, anyway? As usual, I hesitated, panicked, and had second, third, and fourth thoughts. Nonetheless, I was resolved to go, and go I did.
That Friday evening, as I approached the bar, I felt completely out of place. I was wearing street clothes, as I was nowhere near comfortable enough to go anywhere “dressed”. How would I find what I wanted if I couldn’t even dress the part? I had no clue. As I walked in, I expected everyone to look at me. No one did. This calmed me down a bit. I looked around, spotted an empty booth, sat down and wondered if I should approach the bar to order a drink, when someone came over and asked me what I would have. I ordered something simple, and the waiter disappeared. As I looked around, I saw men talking with one another, but detected no signs of sexual activity. Well, what was I expecting, sex on the floor? The waiter reappeared with my drink. I began to wonder if this was a good idea; I mean, what was supposed to happen? It seemed as though nothing would. I was becoming annoyed, and I decided to finish my drink and leave. This had been a waste of time, and I had put myself through all that anguish for nothing.
Just as I emptied my glass, the waiter came over and placed another drink in front of me. I said, “I didn’t order this.”
He replied, “It’s from that gentleman at the bar.” I looked in that direction, and someone smiled at me. I just smiled back, and thanked the waiter. Now what, I wondered. I didn’t have to wait long for my answer. The guy at the bar came over, smiled, said, “hi”, and asked if he could join me. I motioned for him to sit down.
“You look uncomfortable. Is something wrong?”
“Well, I’ve never been here before, and I don’t know anyone here.”
“My name’s Tom.”
“Hi Tom, I’m Tracy.”
“That’s a pretty name. You looked so sad and lonely all by yourself I wanted to try to cheer you up.”
“Why thank you Tom, that was very sweet of you.”
“Not at all. What made you come tonight?”
“Oh, I was just hoping to expand my social life a bit.”
“Hmmm. And just what were you hoping to find?”
Oh, great, now I’ve got to put my cards on the table. What am I supposed to say?
“Well, I was hoping to meet up with someone who wants to meet someone like me.”
“And what would that be?”
Shit, this guy goes right to it. Now what?
“I’m not sure how to...”
“It’s okay, you don’t have to be too open about it. Could I just tell you what I’m looking for instead?”
“Yes, of course.”
“I’m sure you know what kind of a bar this is, right?”
“Yeah...”
“Well, it is frequented by all manner of people, looking to hook up with all types of people. As for me, I like sweet little girly-boys, who like to dress, and I was kinda hoping someone as petite and demure as you might be that. Am I wrong? If so, I apologize. I certainly wouldn’t want to offend or upset you.”
Oh fuck, I thought, how did he know? I can’t say no, but if I say yes, I would be committed to doing something, probably right now, and while he certainly was nice enough, and cute, as well as masculine, I just wasn’t sure.
“I suppose I have to be honest. Yes, that is what I am or like or want, but I am still having a hard time adjusting to my own desires.”
Holy shit, did I actually tell him that? I did. God, now what?
“Would you care to talk about this with me?”
“I don’t know; maybe.”
“Well what exactly is the problem?”
“I like dressing, and I enjoy what I do when I am dressed, but I’m not sure I can say ‘yes, this is what I want to do, how I want to be’, from now on.”
“Let me ask you this. Do you like feeling pretty?”
“Yes.” I was feeling pretty embarrassed at this point.
“Do you like it when someone says you’re pretty when you’re dressed?”
“Yes.” I was feeling almost naked now.
“Do you like it when you feel wanted, desired, lusted after?”
I just nodded my head.
“Does it make you feel sexy?”
I nodded again.
“How does it make you feel when you are touched, caressed, and treated like a sweet girl?”
“Where is this going? I mean, what do you want me to say?”
“Please, calm down, I don’t mean to hurt or upset you; I’m only trying to help. You see, if none of these things bothers you, if instead, they excite and please you, then it’s not the cross dressing that’s the issue.”
“Okay, so what then?”
“Could I ask you something? You don’t have to answer if you don’t want to.”
“What?”
“When was the last time you had sex?”
“A couple months ago, why?”
“And before that, about how long?”
“Maybe the same.”
“I think I know what the problem is.”
“Oh? What?”
“You have never given this lifestyle a fair chance--you’ve never really given yourself a chance to feel comfortable with this side of your being.”
“So, what do you suggest?’
“You’re going to think I’m merely trying to get into your panties.”
“I don’t wear any, but go ahead.”
“Nice! But what I think you need to do is to consider having sex, preferably while dressed, on a fairly regular basis, at least for a few weeks, to see how you like it. If you still feel uncomfortable, that’s one thing, you can always stop. But if not, you might be a lot happier than you are now. What have you got to lose?”
I had to admit he had a point, even if he was volunteering to be that regular sexual partner. And what did I have to lose, anyway? My virginity? That ship had sailed. My inhibitions? My fears? If so, wouldn’t that be a good thing?
“Okay, let’s say you’re right. What should I do, exactly?”
“It’s a lot easier than you expect. Just choose someone with whom you feel as comfortable as you can, someone who seems safe, and tell him what you want. I gaurantee you you will have no difficulty finding a volunteer. It doesn’t have to be me, but it does have to be someone.”
“But how often are you talking about?”
“At least once a week, preferably two or three times, but no more that, at least not at first. You don’t want to get burned-out, or over-worked.”
“I see.”
“Could I make a suggestion?”
“Sure, what?
“Go home, think about this, and if you want to try it with me, give me a call or send me an e-mail. Here, I’ll give you my telephone number and e-mail address.”
“Okay, thank you.”
“I’ll take off now, and I hope I hear from you. But even if I don’t, please try what I suggest, otherwise you will keep on needlessly tormenting yourself.”
“Okay, thanks.”
“Bye Tracy.”
“Bye Tom.”
Well now, that was something! I gulped down what remained of my drink, and walked out into the crisp night air. It felt good, yet somehow dampened my ardor, albeit only temporarily. I knew what he said was true, even as he said it. There was nothing to consider, really. It was only a matter of putting it into practice. But would I have the guts?
When I arrived home, I realized that my goal of “hooking up” with some guy both did and didn’t happen. I had to admit, he didn’t push it. That was a good sign. I went to bed, alone, sexually unsatisfied, realizing that this would continue if I failed to do what Tom had suggested.
The next day I awoke with butterflies in my stomach. I knew what I had to do, but the courage and resolve of the previous night had disappeared, and in its place, the old anxiety had filled the vacuum. I forced myself to do what had to be done, and, despite much trepidation, called the number on the crumpled napkin.
I heard a familiar voice. “Hello?”
“Hi, Tom?”
“Yes, is that you Tracy?”
“Uh huh.”
“I didn’t expect to her from you this soon. I wan’t sure if you would even call at all.”
“Me neither, but I knew I had to do it. You were right last night Tom, and I want to thank you for your kindness.”
“That’s so sweet of you to say Tracy honey; what would you like to do?”
I just melted inside when he said that. Why? It just made me feel so soft and feminine, and I liked the feeling. I just wasn’t sure if I liked that I liked the feeling.
“Well, I think I should do what you suggested, and I don’t know anyone whom it would be better to do it.”
“I’m so flattered that you feel that way.”
“So, I don’t know how to begin exactly, I mean....”
“It’s okay sweetheart, we can take it slowly.”
Christ, that ‘sweetheart’ crap really does it to me. Fuck!
“So honey, when would you like to get together?”
“Tomorrow is Sunday--would that be okay?”
“Of course baby doll, that would be fine. Where would you like to meet?”
“I think I would be more comfortable here, at least at first.”
“Of course. Do you want to tell me where to come?”
“Right.” Then I gave him my address, and we agreed upon a time, and hung up. Fuck. I was completely committed now, no getting out of it. But it’s what I want, isn’t it? Well....yes and no. We’ll see. And how we’ll see. Oh boy.
The day dragged by, and I felt aroused, frightened, excited, upset with myself for feeling excited, and generally exhausted from the energy that all this was using. Finally night came, and I went to bed early so I wouldn’t have to obsess over this anymore.
The next morning, I awoke with a feeling of dread. Why? I wanted this. I asked for this. I needed to do this. I think the knowledge that I had made a potentially life-changing decision was what concerned me. Oh well, too late now. I got up, forced myself to eat something to keep my strength up, then prepared for my date. I won’t bore you with the usual descriptions of removing hair, or how sensuous it feels to put on nylons: those of us who’ve dressed already know, and those who haven’t need to find out for themselves.
So what to wear? I think a little black dress, with black suede shoes, matching stockings, gold hoop earrings, and a velvet choker would do nicely. As the appointed hour approached, I began to relax; since I was all dressed up and ready to go, there was nothing more to do but wait. I didn’t have to wait long. Tom arrived right on time. He even brought some wine. How thoughtful!!
“Hi,” I said nervously.
“Hi Tracy, how are you?”
“Okay, a little nervous, I’m not sure why. Please, come in.”
“Thank you.” He handed me the wine, I took it into the kitchen. Tom followed.
“Would you like me to open it for you?’
“Please.”
As he deftly removed the cork, I retrieved two glasses.
“Care for some now?”
“Yes, thank you.” He poured some for me. I needed something at this point, and it tasted good besides. He took my hand, and led me over to the couch. I sat down, he sat beside me. He continued to hold my hand, gently caressing it. This was nice.
“So, what, I mean, how, er,” I mumbled. At this point Tom pulled me
toward him, and kissed me softly on the lips. I trembled with anticipation. He kissed me again. I kissed back, then parted my lips, hoping he’d take the hint. He did. I sucked on his tongue like a hungry animal. He said,
“Take it easy!”
“I can’t,” I replied.
“I don’t want to rush you.”
“It’s not rushing if it’s what I want, right?”
He stood up and, holding both my hands, guided me to my feet. Then he took me in his arms, while kissing me on the neck. I thought my knees were going to collapse.
“Tom please. I’ve been anticipating this for days; let’s go?”
Wordlessly, he escorted me into the bedroom. Then, oh so gently, he began to undress me. I was so hot by then I couldn’t stand it. I cupped his cock and balls; he seemed to like that. Finally, I felt a little in control!
My dress fell to the floor. Tom slid my panties down; they fell to my ankles, then joined my dress as I stepped out of them. I fell back on to the bed. Tom quickly undressed, then lay on the bed beside me. As he kissed me again, he began to move down to my neck. I wondered if he would suck on my nipples, but instead he parted my legs, and kissed and caressed my inner thighs with his tongue. I almost came right then and there. His cock was already hard, so I told him I wanted him to cum in my mouth. He appeared surprised by my boldness, but not displeased.
While he lay on his back, I moved into position, then kissed the mushroom head of his beautiful cock. He responded nicely, and I felt gratified, so I licked its full length, slowly, teasingly, then back down again. I kept doing that, only after he was beside himself with desire did I finally take it in my soft, warm, wet mouth. I just held it there, motionless. Then, ever, so slowly, I began swirling my tongue around it, all the while keeping its full length, or most of it, in my mouth. I just loved this; I could have kept it up all day, in both senses of the term.
As I caressed the underside of his glans, he began to moan, writhing in response to my ministrations.
“Oh God, I can’t believe this, you’re amazing!”
“Oh, everyone tells me that. You’re all just being sweet!”
“Like hell! I’m telling you, you are one in a million.”
“Well, I like what I do.”
“Me too. Please please don’t stop.”
I stopped.
“Are you sure? I mean, I wouldn’t want you to get bored or anything.”
“Oh God, you’re killing me!”
“Well, I wouldn’t want to do that. Maybe we should do something else then. Want to watch TV?”
“For God’s sake!!”
“Hmmm? You want something?”
“ Please .”
“Please what?” I asked, all innocent-like.
“For the love of God Tracy!!”
It’s funny how sex seems to elicit expressions of religiosity from people, isn’t it?
“Okay, okay.” I went back to ‘work’.
I started to pump, up and down, pulling out from the tip with a slurppy “pop” as I sucked as well as pumped. This about drove him to distraction, which only excited me more, so much so I actually came before he did, without either of us even touching me. He was too preoccupied to notice.
As he began to buck, I knew my reward wasn’t far off. I just kept varying my routine, and waited. I didn’t have to wait long. As he lost all control, he came in firm spurts, and the warm, sweet, ambrosial liquid flooded into my waiting, eager mouth. I swallowed, as I always do, and savored the multiple blasts.
I sat up. Tom looked spent; spent, but happy. I lay down beside him, and he clasped me in his arms, and kissed me on my head as we cuddled for an indeterminate amount of time. I held his now supple cock in my tiny hand.
After a while, it began to stir back to life, and I gently kneaded it to its full extent. Then I kissed him on the stomach, licking and caressing with my lips and tongue. I moved down, but skipped his cock and balls, and went to his thigh, as he had mine, just above the knee. Using my tongue in the same way, I moved ever so slowly up to his balls, but before reaching them, moved back down again. I repeated this a few times before moving to the other leg. If he was hard before, he was positively rigid now.
I asked him if he would like me to suck on his cock again. He didn’t say anything, but the expression on his face said it all. I repeated my earlier activities, this time stopping short of allowing him to cum. I had other ideas, and apparently so did he. He exchanged places with me, reached for some lubricant I had on the nightstand, then adroitly and gently prepared my already waiting ass-pussy. He parted my legs, placing them on his shoulders, then slowly, sweetly, entered me.
I was at peace. He just held it there, not moving for the longest while. When I could stand it no longer, I said, “Tom, please.”
“Please? Please what?”
Oh fuck, he was paying me back now. Great.
“Oh come on, don’t make me wait.”
“Okay, I can’t do that to you after what you did for me.”
“Thank you.”
With that, he commenced pleasuring me, slowly, gradually building to a crescendo of passion, stopping when it appeared I might cum, only to begin again, then stop, then begin. I don’t know how long this lasted, but eventually I did cum; and how I came. I thought he had too, but no, he just paused for a bit, then resumed fucking.
“Holy shit, are you going to continue?” I asked.
“Yes, we’re just getting started. You need to find out just how horny you can be, and how passionate.”
“Just getting started? What do you mean?”
“You’ll find out soon enough. Just lie there and relax; I’ll take care of the rest.”
And, he did. Half an hour later, he was still at it. No one had ever gone that long with me before, and he didn’t even seem tired. What did this man eat?
I felt the familiar upsurge of desire and arousal, and to my surprise, experienced another pulsating orgasm. I figured that was it, no way I could cum anymore, and no way he could keep fucking me. Boy was I wrong; wrong on both counts.
I started to feel like I was going to cum again; I told Tom I didn’t feel like I could take any more. He just ignored me, and said he wan’t going to stop anytime soon.
“Don't keep fighting it--"
"But I'm not a woman!"
"No? You may not have the body of a woman, but you sure have the desires of a woman, the feelings of a woman, the reactions of a woman, the responses of a woman. You dress like one, smell like one, act like one, and have a smooth, slender, petite body like one. There's more to being a woman than having a pussy. Psychologically, and in your behavior, your passions, you're more woman than most, believe me! You suck cock like one, and you let me fuck you, just like a woman. Face it, you've got a woman’s figure and a woman’s emotions. You like dressing up in girly clothes, and you look fucking good as a girl. Why don't you just cut the crap and, more to the point, accept that you are a woman, at least in part.”
"I don't know, I--I...."
"Tell me you don't like this!"
"I can't."
He was almost assuredly right. I was, in my actions and reactions, and to all appearances, a woman, at least at times, and to some extent, but my pride resisted that admission. However, there's no point in fighting it. What happened, happened. You can deny the facts of reality all you like, but that won't make them go away, will it?
We had now been at it for a good hour and a half, maybe more, and he was still fucking me. He had re-lubricated his cock, so as not to injure me, but he went at it like he hadn’t had sex for months. He picked up the pace, and as he sensed my growing excitement, he accelerated his fucking to a fever pitch, pounding me hard and long. I loved it. When I couldn’t hold it any longer, my body convulsed in uncontrollable spasms. I thought I’d never stop cumming. I couldn’t believe how hard I came, or how long. Tom came too, as I could feel his warm cum lave my now gaping ass with profuse torrents of liquid lust. I glanced at the clock. We’d been fucking for two hours and fifteen minutes.
Eventually we recovered enough to get up. We showered, separately, as I didn’t want to spoil the illusion by removing my hair in his presence. I then fixed us a snack while he showered. As he re-emerged, I said, “Well, that never happened before!”
“The multiple orgasms, or the two-hour long fuck?”
“Both.”
“Well, there’s more where that came from.”
“I don’t know if I can handle more!”
“I don’t mean tonight, but another night, and soon. Remember, you agreed to do this on a regular basis for a while, right?”
“Why yes, of course. I just didn’t expect it to be so.....”
“I know. But that’s because you never gave it a chance. You never gave yourself a chance.”
“Okay, so when?”
“Well, today is Sunday. You should rest and recuperate a little while, but not too long, or you might want to go back to doing nothing again. How about Wednesday?”
“Okay, Wednesday it is. Want to come here again?”
“Yes, I think it would be best; you need to feel as comfortable as possible.”
“Okay, here on Wednesday. Great.”
We finished eating, then embraced, he squeezed my ass affectionately, then departed.
So, what to make of this? I just had the longest, most intense, most orgasmic sexual experience of my life. Now what? What did it all mean? Did it have to mean something? This was just too much to sort out like that. I did feel calm, relaxed, satisfied, and kind of all warm inside. I was tired, so I went to bed early, although I had to change the sheets first.
The next morning I awoke feeling rested and serene. I took the day off from work, and spent the day doing nothing in particular. I washed some sheets, (!) ate a little, listened to some music, and thought about the previous day’s activities. I felt good about them, and good about myself. The following day, I found myself looking forward to Wednesday. I couldn’t do any work, I just went through the motions. I felt horny. I wondered how that could be; after all, it was only two days. Nevertheless, I was. I went home early, and since I had taken Monday off, it surprised nobody. I found myself fantasizing about sex all evening.
Wednesday morning, I decided to focus on work. I tried, really. But all I cared about was getting fucked again. The evening couldn’t come soon enough. When I finally got to go home, I immediately showered, dressed, and waited. I couldn’t even eat. After what seemed an unendurable wait, Tom arrived. I practically assaulted him. If he hadn’t been prepared to have sex right away, I swear I would have exploded. Fortunately, he was not exactly adverse to the idea. I won’t detail the evening’s activities, as they were substantially the same as those already described, and I have no desire to be redundant. Suffice it to say that the evening disappointed neither of us.
This pattern repeated itself a couple of times more over the course of the week. We met again on Friday; this time it was only two days between dates; then again on Sunday. On Monday, I called and told Tom I didn’t want to wait until Wednesday or even Tuesday; I wanted him right then.
He was there in twenty minutes.
“So, tell me, were you nervous?”
“When?”
“Today.”
“Over what?”
“My coming over.”
“No, why would I be?”
“Didn’t you tell me that you always got nervous when you were meeting someone for sex?”
He was right, I always did. But lately, I hadn’t; not since our first date.
“Hey, how about that! I felt excited, adrenalized, but not anxious. Wow! I guess things have changed a little.”
“I’d say a lot. Inside of a week, you’ve had sex four times in eight days, as opposed to four times over the course of maybe a year or more.”
“Holy shit! You’re right! What the hell’s happening to me?”
“I can tell you. You finally got in touch with your inner slut.”
“Oh come on! That sounds cute, but it’s really silly!”
“Is it? Just think about it. It’s a psychological fact that the more sex you have, the more you want. It’s like an addiction.”
“I guess I do want it more. It does sort of feel like an addiction.”
“It’s true. You get a dopamine rush, and this is bio-chemical, not imaginary.”
“So now I’m a sex addict? What does that mean, that I’m going to be some sort of nymphomaniac?”
“Going to be?” Look at yourself, you have had more sex in one week than in the past two years, and you still can’t get enough.”
Shit. He was right. What was happening, what has happened, to me? Where was this going? What would the outcome be? Is there more to come? I shuddered at the idea that I could be so out of control, so driven by my desires. But hadn’t I been all along? The only difference was that while before, I was resisting them, now I wasn’t. But at least before I had some measure of control, in between bouts of extreme lust; now, it was fast becoming a lifestyle, if it hadn’t already become one. On the other hand, before I was miserable, and now I was content, ecstatic even.
“I’ve got to process all this. I need some time.”
“So, no sex?”
“I didn’t say that. Let’s not go crazy!”
“Okay.”
So, yet again, we spent the next few hours slaking our, or at least my, seemingly unquenchable thirst for raw, uninhibited sex. I regretted none of it, but I did have to reflect upon the significance of all this. The next day was a holiday, so I had no distractions. I spent the holiday looking at how far I came in just a little more than a week, and in wondering how it would end.
In addition, I pondered the impact of all this upon my sexual identity. After all, when not dressed, I still had masculine desires, masculine lust for women. Wouldn’t this erode, even destroy, my manhood? It turns out that terms like homosexual and bisexual were only coined in the 19 th century. It seems that in ancient Greece, men and women both had same sex lovers, yet were not classified in the same terms we employ. In Rome, it was considered normal for both sexes to be sexual partners, and so it was actually expected. Only the social status of the participants determined whether the alliance was considered acceptable.
I read about the Kinsey scale, with exclusive homosexuality at one end, exclusive heterosexuality at the other, and most people falling somewhere along the continuum, with bisexuality in the middle.
I then found the Klein scale, which was more complex, as is human sexuality itself. In it, to whom you were attracted, about whom you fantasized, as well as with whom you had sex, were all dimensions that were included, as well emotional preference. This made sense to me. I have no interest in viewing images of men, nude or otherwise, whereas I love photographs of hot women. Same goes for strippers: women, yes; men, no.
Similarly, emotionally, I have always and only fallen in love with women. The same goes for kissing: only women, despite that first experience with Tom. I suspect I was carried away by the drama of being seduced. So all romance for me, whether fantasy or real, has been with or about women. But my sexual fantasies and activities have included both. So okay, I’m bisexual then; no news there.
I dislike those who go through life parroting the cliche, “I don’t like labels.” How else do you tell a can of beans from a can of peas? Such people simply don’t want to confront the consequences of clear identification, or are unwilling to take the time and trouble to attain that clarity. One must also avoid the other trite platitude: “Everybody’s bisexual.” If what they mean is that the potential for same sex arousal and activity exists in everyone, that’s one thing; but that simply isn’t how the word is used. What people mean is what one STD counselor asked me: “Do you have sex with women, men, or both?” She didn’t care about my romances, my fantasies, or how I categorized myself; all she cared about was what I did and with whom. So “bisexual,” the way most people employ the term, means precisely that, having sex with both. Trying to call everyone that is as stupid as those, usually exclusively homosexual men, who try to deny the very existence of bisexuality. The fact is, many of us like both. Deal with it.
Someone reading this may be saying to themselves, “Bullshit. This pervert is just rationalizing, trying to normalize his predicament.” I am not contending it’s “normal”, if by that we mean statistically; I am merely stating historical, psychological, and biological facts, which means it is natural, and occurs across virtually all species. As to what is “natural”: wearing clothes is “unnatural”; flying is “unnatural”; wearing glasses or contacts is “unnatural”; oral or anal sex even between a man and a woman is “unnatural”. The fact is, human behavior in general, and sexual activity in particular, enjoy a certain plasticity, arising from the human capacity to transcend hard-wired behavioral programming.
Neither do I argue that all dislike or disapproval is attributable to “homophobia”; yes, some of it is, especially when people become absolutely enraged by it. I too dislike those mincing, plumed and sequined denizens of gay pride parades, with wobbling heads, glazed eyes, and voices like Richard Simmons. But I’m not enraged by them, they just repulse me, and they would even if they were straight.
So what about the cross-dressing then? Some CD’s are straight. That surprises and mystifies me. What’s the point? But it’s okay, they’re not hurting anyone. But for me, it is an expression of my female side, a way of getting in touch with it. It seems to make more sense that, if you’re going to experience the joys of having sex with as a woman with a man, then you might as well get as close to that experience, and that side of yourself, as possible. This is why getting a blow job from a man, or fucking one, doesn’t appeal to me: I can do that with a pretty woman, so why some (to me at least) sexually unappealing guy? Of course a beautiful “she-male” is another thing entirely. And then there are transexuals, who get or want to get a sex change operation. Let’s face it, sex is just not all that black and white. It is funny though, how men who only take the “active” or “male” role when having sex with other men, continue to tell themselves that they are straight. They may not be gay, or even bi, but they still seek sex with men, and that’s not exactly inflexibly straight.
Even where bisexuality, transsexualism, and related topics are not an issue, the genetic, hormonal, and anatomical aspects of embryology are enormously complex. Human embryos are the result of fertilization of an ovum by a spermatozoan. Eggs are gender neutral; however, they all contain an X-chromosome, and no Y. If the father contributes another
X-chromosome, the fertilized egg, now a zygote, will, under normal circumstances, become female; if he contributes a Y, male. However, not all embryos contain XX or XY chromosomes; some are XXX, some XYY, and I’ve even seen XXXY, which produced a classic “she-male”.
Some XY individuals have external genitalia that develop to look female, and other XX individuals whose external genitalia develop to look male. Different combinations give rise to different outcomes. In addition, different hormonal secretions result from these combinations. The amounts of the male or female hormones produced will alter the anatomical structures, despite the mere genetic aspects. Hence, development in puberty will not always be in complete accord with the chromosomal determinants.
Tissues that create the male genital components create the equivalent components in females. The tissue that forms the penis in males will form the clitoris in females, and the tissue that forms the scrotum will form the labia majora and minora in females. Males also have nipples, which implies less sexual dimorphism than is generally supposed.
The result of all this is that the simplistic sexual or gender bifurcation contemporary society imposes upon us is at variance with scientific fact, as well as informal observations of human behavior: we are more complex than that.
A couple days later, Tom called to see how I was. I told him I was fine, and asked when he would like to come by. He said anytime, so I suggested that evening, to which he agreed. He also asked me to wear some sort of nightie, so I selected a baby-doll top with matching bottom, the black velvet choker, and nothing else. I felt naked, but that was a good feeling.
As usual, Tom was right on time. I could tell he really liked the baby-doll nightie, and so I decided to just dropped to my knees and suck his cock right then and there. He resisted my efforts, but I prevailed in the end, and he exploded into my mouth. This time I guided him into the bedroom. We lay down beside one another, me on my tummy, him caressing me gently. He began kissing me on the back of my knee, then worked his way down rather than up, eventually kissing me on the bottom of my foot. This felt wonderful and sweet. Tom then gradually worked his way back up, eventually giving me the longest and best rim job I ever experienced. After he nearly drove me crazy with desire, he fucked me from behind, with my bottom raised as I lay on a couple of pillows. This time he fucked me hard and roughly, pounding me into sweet surrender. I don’t know how I am able to cum without any genital stimulation, but cum I did; however, before he came, Tom pulled out at the last moment and came in my mouth for the second time that evening. We then collapsed in satisfied tranquility.
The next day Tom called and said he had something to tell me. I felt worried and anxious. I asked him what, and he said he would discuss it when we met. Great. Don’t you just love it when someone holds a thing like that over your head, then keeps you wondering when the other shoe is going to drop? So I agreed to meet him, and I joined him for a cup of tea.
“So what’s wrong?” I began.
“Nothing, just relax. I just wanted to tell you that I think you are ready for the next step.”
“Next step? What next step?”
“I want to take you to a t-girl club this weekend.”
“Okay, so what’s the big deal?”
“I want you to go dressed.”
“What?! Are you kidding me?! I’ve never gone out dressed! I’ve only dressed in private. You can’t be serious!”
“I am serious. I think you need to do this.”
“No, I really don’t. I’m just fine with the way things are. Really!!”
“I know that, and that’s the problem. You get into your comfort zone, then you don’t want to stretch. I think you need to find out how comfortable you can be en femme , and interact with others like yourself, as well as male admirers you will meet.”
“I don’t know Tom. That is really scary.”
“What’s there to fear?” Everyone there will be like you, or will be looking for someone like you. And besides, I’ll be there with you. So what’s the problem?”
“Well, I dunno, maybe it will be okay, it’s just....”
“I know I know. It’s just a matter of getting used to it. However, it will be late, we can go around midnight. They’re open until four in the morning. I’ll drive us, so you only have to walk from the car to the club, and they have a parking lot.”
“Well, maybe....”
“Oh come on, be a brave girl!”
“Oh shit, why do you have to talk to me like that? You know it makes me melt inside.”
“I know, and that’s why!”
“Great. So I’m that easy to manipulate?”
“Not really, just easy to fuck.”
“So is that why you like t-girls and CD’s more than genetic women?”
“In part, yes. You’re both hornier, easier to bed, less inhibited, and don’t need or want the melodrama. You don’t make demands, we don’t have to jump through hoops in order to fuck you, or wonder if we’re going to have sex with you when we do get together. You don’t ever say you don’t like oral sex, or you don’t swallow, or you don’t do anal sex.”
“But what about a woman’s pussy; don’t you miss that? I mean, I still enjoy the fragrance and flavor of a woman.”
“Your ass is tighter than any pussy, you don’t get pregnant, and you’re never ‘on the rag’. On top of all that, you give better head. We can be honest about what we want, and we don’t have to put up with all the bullshit. With genetic women, the fucking you get isn’t worth the fucking you get. They’re moody, and always upset over something. You’re not oversensitive, and not so easily hurt. You’re not nagging, complaining, clinging, irrational crybabies. Also, you’re not timid and risk-averse. You’re simply better, in bed and out.”
Wow. I never heard that before. But, I can see it. All this time I thought I needed to study women in order to replicate the experience, whereas maybe women have something to learn from us. Amazing. Christ, what a week. What an adventure. And we weren’t finished yet.
“Okay, so this is Wednesday, when are you suggesting we go?”
“Friday or Saturday. Have you a preference?”
“Not really; I’ll be petrified in either case. Let’s just get it over with, the sooner the better.”
“So Friday then?”
“What time?”
“I’ll come by around eleven, that way we can take our time.”
“Sounds good. What should I wear?”
“Whatever you feel comfortable in. You look hot in everything I’ve seen you in so far.”
“Well, I don’t suppose I can wear a nightie or bustier!”
“Don’t be too sure. I’ve seen some surprising outfits there.”
“Oh boy, this is gonna be weird!”
“You don’t have to do a thing. We can just sit and drink if you like, watch other people, dance if you want to, whatever.”
“Okay. I’ll see you then. Bye bye.”
“Bye sweetheart.”
Oh fuck! This is huge! It’s one thing dressing at home, or for a sex partner, but out in public? Oh my God!
At least I have the advantage of being 5’ 7,” 129 pounds, with refined features and a petite figure. I only wear a size seven and a half men’s shoe, which is nine for a woman’s shoe. You’d think that the numbering system would be the other way around, making a woman’s foot smaller. Of course in Europe the sizes are all completely different for both. In addition to having soft features, I have no hair on my chest, back, ass, or even underarms, and I only need to shave my face every three days. The hair on my arms and legs is extremely light, so that’s a help too. I have no tattoos and nothing pierced. Men seem to like that.
So okay, I needed to plan this. I decided on a hot slit-skirt with a cute top, black stockings and boots. The boots would be easier to walk in than pumps, and yet they still look feminine. This was going to be exciting.
Well, the days dragged on, and of course, I felt the usual anxiety I experience when confronted with almost anything new. As Friday arrived, I became even more nervous. I wanted this over with. I began to prepare for Friday night.
As the appointed hour approached, I dressed, had a glass of wine, and waited. Just after eleven, Tom arrived. I opened the door, and told him how frightened I still felt. He gave me a nice hug, and assured me everything would be fine.
“Are you ready to go?”
“No!”
“I know, I know, but you need to relax, it will be fun, really.”
“Okay, let’s go then. I can’t stand any more of this waiting around.”
“Sure, come on.”
I walked out of my apartment dressed as a woman for the first time in my life. Fortunately, it was late at night, and no one was around to see me, but since I was passable, it really wouldn’t have mattered even if they had. Still, it being my first time and all, I was not able to take much comfort in that.
*
I have received many responses from readers of the first part of My Sexual Odyssey, thanking me for elucidating issues with which they’ve been confronted, as well as giving voice to feelings that they have experienced. I am gratified if I was of any help. This is a continuation of Part I, and is incomprehensible without reading it first. There are hotter stories on Lush, more beautiful stories and poems on Lush, but I doubt that anything is as autobiographically truthful. There are no women with mischievous grins, immediately eager to feminize me; no sales women who wickedly wink at me, then want to have sex in the changing rooms, and no cocks as long as your forearm and as big in circumference as a beer can. The world’s record is thirteen and a half inches, and I’ve never encountered anything greater than nine inches, and don’t want to. So, if you want wall-to-wall sex with no story no truth and no content, look elsewhere.
Alma
- 26.02.2020
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- Category:
- Crossdressing
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