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My Sexual Odyssey Part 1 How I Got Started

This is the first in a series of stories that will cover my sexual experiences in chronological orde
I was always extremely sensuous, expressed in the love of the feel of satin and silk, as well as the feel of going barefoot, which was nearly impossible in the city, even indoors, not part of the culture. Where I live now it is, and so I go not only barefoot but also nude when at home.

I don’t know if this is significant or not. However, the first time I noticed anything unusual was probably when I saw a film on TV in which a boy masqueraded as a girl for some reason or other. I recall how this gave me a peculiar feeling or sensation, coupled with a certain ambivalent desire to have that experience. When I read Mark Twain’s Huckleberry Finn, in which the protagonist did precisely the same thing at some point, and again, I experienced the mixture of curiosity, with a sense of strangeness in reaction.

I chanced upon two magazines which, in addition to some suggestive heterosexual stories, was included a photo layout showing two nude men in a barn, lying in hay or straw, not doing anything much, but I recall envying the sensuality of the situation, while not feeling any attraction for the men.

At around age sixteen, I was eager to see pictures or images of any sort of nude or semi-nude women. I had no older brother with men’s magazines, nor any sisters to see in states of undress. I had to content myself with advertisements for women’s undergarments and sleepwear that appeared at the ends of magazines.

As these were of the “Victoria’s Secret” variety, they were sheer, and/or peek-a-boo in style, which pleased me greatly. However, I recall very much envying, again, the sensuality of the lingerie, and the fact that women could look and feel sexy, whereas there appeared no such option for men. Among the baby doll and other outfits were ads for harem pajamas, with the see through pants hugging the hips of the models. I decided to imitate that, in order to experience the sensuousness of the clothing, so I pushed the bottoms of my pajamas down in a similar manner, and rolled up the legs a little.

I really didn’t wish to dress as a woman, just feel sexy like one. The ramifications of all this failed to dawn upon me at that time. This, coupled with the habit of removing my pajama bottoms in bed to experience the sensation of nudity, continued for a number of years. I suspect the need for these tactics was exacerbated by the absence of female companionship; my adolescence was a lonely and sexless one.

Curiously, two practices emerged, more or less simultaneously: anal self-stimulation, and masturbation ending in ejaculation into my mouth. These practices were infrequent, and attended with feelings of self-revulsion. Nonetheless, I felt driven to do these. This I interpreted at the time as owing to a superabundance of unsatisfied sexual desire. Still, I fantasized about women, and was attracted solely to their bodies.

I did eventually have sex with women, and I enjoyed it so much I assumed the result would be the disappearance of these urges and practices. I was right. However, a bit later, I experienced an almost irresistible urge to have sex with a man. I had no idea where this came from, or what to do about it, save to resist, which I did.

Despite that, a re-emergence of these seemingly uncontrollable urges seemed to come out of nowhere. I resisted some more. Finally, I could do so no longer, and went to a gay neighborhood and quickly met someone who was looking for somebody like me.

We went to his apartment, and without hesitation I undressed and went down on him. The sensation of his cock in my mouth felt strangely familiar. I wanted to experience getting fucked as well, and so I did, without preparation or lubrication; I was naive, and he was thick, and probably eight inches or so in length. While it hurt, I still managed to enjoy the sensation, but wanted to taste cum, so I had him cum in my mouth, which I swallowed and enjoyed completely.

Afterward, however, I noticed two reactions: first, a sense of clarity and calm, as one experiences when a fever breaks and this desire or compulsion certainly was feverish. Secondly, and doubtless more typically, a sense of self-loathing, feeling dirty, soiled, used, and so on. I decided not to repeat the experience.

I really couldn’t stop thinking about that first experience, and while I told myself I didn’t want to repeat it, I kept fantasizing about it. My ass was only slightly sore, but also sort of tingly. My body felt alight and alive.

I liked feeling lusted for, and yet I was upset with myself for feeling that way.

My desire was to experience sex as a woman, or from a woman’s perspective: the other side I already knew, and I didn’t need a man for that. Besides, I was not and am not attracted to men per se, but only to their cocks. I felt like this wasn't something I should be doing, but my body craved it, and I wanted men to want me sexually like that.

Well, as you can surmise, these desires would reappear, and I either resisted, or repeated the experiences and their aftermaths. So I still occasionally succumbed, and still felt uncomfortable with the outcome, although eventually somewhat less so.

What, you may ask, is the issue here? So I discovered that I’m bisexual. What of it? Given that I do not come from a religious background, that I was born and raised in a very cosmopolitan city, that I am very educated, and well-traveled, these reactions are hard to explain. Possibly my self-image was incompatible with it. It wasn’t social acceptance I needed, but self-acceptance. I could tell myself I wouldn’t do it, but deep down I knew I would succumb to my dark desires. They made me feel dirty and ashamed, but horny as well.

It felt degrading and naughty, yet it fulfilled some need I didn’t know I had, some identity that had been kept secret from myself. This part was very liberating and exciting.

Nonetheless, when I took out or answered an ad, I felt adrenalized, even shaking. Why did I force myself to do this? If they responded, I was excited, yet terrified. If they didn’t, I felt disappointed and discouraged, but relieved. If I accepted, I would think about it all day, with a knot in my stomach. Yet, when it came time to meet, I half felt like canceling or bailing out, but did not do so. When we did meet, I was just fine; after all, I had done this before, and enjoyed it, so what’s the big deal?

I decided to give it one last try, do everything, satisfy my curiosity, and get it out of my system once and for all. Then the need would be fulfilled, and I could get on with my straight life.

Eventually, I met a man on Craigslist. I felt panicky, yet determined to see it through. I knew full well that I didn't have to go through with it, and hoped he would cancel so I wouldn’t have to. I spent the day thinking about it, working myself into a state of neurotic anxiety. Why was I putting myself through all this? It was as if I had no choice: my desires got the better of my resolution. I felt like a slave to my lust. What was I afraid of, that I would enjoy it? Why would that be bad? Maybe it was because I feared that it would be impossible to resist continuing, but why would that be a bad thing?

Why I still experienced these inhibitions I cannot say, but I knew I could force myself to get there, and once there, I would relax, which I did. How could I do this? How could I agree to have sex with not just a man, but a man I hadn’t even met, like some cheap hooker? I used to wonder how women did it and why they did it. Yet here I was, about to do precisely that. I felt enormously conflicted, both driven to see it through, and wanting to run home to safety. The closer I got to his hotel, the more nervous I got. I wanted to turn around. I almost chickened out. Almost. Scared or not, I expected to like it once I arrived.

Once there, I felt okay, and immediately suggested we undress. I then took his cock in my hand, and he seemed surprised, but pleased. He was former military, (so many are) who said he wanted to treat me just like a woman: kissing, licking, caressing, rimming. That was an exciting and unexpected thrill. And of course we fucked. I loved it. I sucked him until he was ready to fuck. I felt like I could have done that for hours. Then he held my ankles as he fucked me with his seven and a half inch cock, and then pulled out to come in my mouth. Then he had me suck his cock until he was hard again, then fucked me once more with my legs over his shoulders, still pulling out at the last second in order to flood my mouth with warm cum.

On the way home, I realized that I didn’t actually regret having had these experiences, but I thought I didn’t need to do it anymore. What more was there to do, to experience, to learn? What would be the point? This lasted for some weeks.

Sometime afterward, I began scanning ads again. It was like a drug. I wanted to stop, but couldn’t. I found someone on Craigslist who wanted a CD. I was curious, and interested in the sex, and I wondered what I would look like, so I decided to buy some items, a black wig, sexy sleepwear, black stockings, red garter belt, black patent leather pumps, even some make up. I found it surprisingly easy to put on the lipstick, using my little finger to trace my lips and press it in, even the first time. I selected a unisex name that would work with men looking for bottom men or for CD’s, or CD’s looking for CD’s. I expected this to be a one-time adventure.

I was struck by the fact that stockings are so sheer. I was accustomed to socks so that when I wore stockings, the feeling of the carpet was almost like being barefoot. This was a pleasant surprise. I was already starting to like it. It made me feel so sexy and feminine. Then I put on an anklet and some lipstick, then perfume. This was getting to feel really odd. When I saw how I looked, I couldn’t believe how feminine and sexy I appeared, if I do say so myself.

I was worried though. Would he reject me? Would he laugh at me? Would he think I looked silly? I drove to his home in street clothes. After all, what if I got stopped while dressed? So I had to change at his place. He was okay with that.

Anyway we met, and even before I changed, I could tell by the way he reacted to me that everything would be fine. He was interested, and when I came out of the bathroom dressed, he was visibly turned on, which of course pleased and reassured me. I realized something in that moment. Women have great power over men due to sex, but that power is given over to the woman by the man’s sexual desire. If he isn’t interested, then she can do nothing, and feels foolish doing her seduction routine. But if he is, then she becomes confident, and can work her feminine wiles on him. The same is true for CD’s and T-girls. And most men are lonely, frustrated, and horny, therefore somewhat desperate. Those seeking CD’s aren’t going to laugh, because that’s what they want. Why? Because they don’t have to buy presents, buy dinners, go out on dates, send flowers, or make promises, all in the hope that maybe they will get lucky. With us, they know they’re going to get a good sucking off and a good fuck, the same goes for us. We know we will be desired, lusted after, and that rarely happens with women.

So I had sex with these items on, and it felt thrilling, although the wig was hot, and the hair kept getting in my mouth when I sucked his cock. I wonder if women feel hot with long hair, or is it because it’s a wig? However, it did look good on me, and it made me feel womanly.

I put his wonderful member into my eagerly waiting mouth, and sucked for all I was worth. I slurped and slurped, and he grew bigger and bigger. I said, "I need you to come in my mouth." He became more aroused, and began to pump mightily.

Finally, he erupted in my mouth. He came in powerful thick spurts, and I enjoyed swallowing every last drop. He was completely spent. Then he said, "Girl, you are one hot little slut. Come on sweetheart, let's get on the bed."

I stood up, and he picked me up and carried me over to the bed, and gently placed me on it, lying down next to me. We stayed there a while, and then he seemed to become aroused again. This excited me, and so I sucked on his cock again. After slurping on his cock, he said, "I want to fuck you. I want to fuck that sweet little ass of yours. I want to cum in your ass."

"My pleasure," I responded, and got on my back. He reached for a tube of lubricant he had deposited onto the nightstand, and as I lifted my hips and spread my legs, he began lubricating my already dilating asshole. And so he mounted me and placed his cock at the rim of my ass, and I reached down and guided him in. The thick bulb of his head gently penetrated, then slid easily all the way in. I felt so full. I moaned and told him how much I enjoyed putting out for him. He seemed pleased by that, and began to pump his cock in my ass. The sensation was first slightly warming, and then it quickly grew to a searing heat, with my own thrusts meeting his. I felt so whole, so complete, and like this is what I was made for. I said, "I love fucking for you. I love being fucked by you. I love to fuck period. I just love fucking."

He fucked me with my stocking clad legs over his shoulders. I looked at my feet in the air, with my patent leather fuck me pumps on, and I really got carried away by the excitement of it all. This man was treating me like a woman, and I was enjoying it tremendously.

I convulsed in uncontrollable orgasms, as wave after wave of contractions spent themselves, and I lost all control. It was wonderful. At that point he began to grunt, and he came too, fucking me like his bitch, like his own private toy, and finally sent spurt after spurt into my now gaping ass. “I can feel your hot cum in my ass,” I said. Eventually he collapsed, and then slowly slid out. I caressed his cock in my hand.

"Sweetheart, you're wonderful. You're one hot little bitch!"

"I try."

We met only a few times.

I eventually moved and, as I did so, asked myself if I was likely to see him again. I decided probably not, so I tossed most of the clothing out, but kept the shoes, which I liked, although I don’t know how women walk in them. Still, they felt okay when sitting or lying down, and I enjoyed looking up at them over someone’s shoulders. I didn’t see it as “purging” so much as not seeing the necessity for them, and, as I said, I kept the shoes.

I read more ads on Craigslist, and so began taking pictures of myself with my computer. I decided to try the CD thing again, and so went out and bought another, better, long blonde wig, and red lingerie and some more black stockings. I don’t like pantyhose. I want my ass bare and open. Besides, I like the black stockings, and garter belts or garters.

I discovered that I enjoyed posing for the pictures, and seeing myself that way, going back to the women can look hot and sexy thing. Eventually, I had sex with more men while wearing these.

I always receive rave reviews for my performances, as well as my naturally smooth body. Anyway, I feel okay with cross-dressing, but was for a while still ambivalent about the sex. But having men saying I’m hot, feeling desired, wanted, lusted after, turning them on, then feeling their excitement and interest was and is a great turn on for me. I felt attractive, sexy, risqué, naughty, and feminine. I liked the attention, the lust, and of course the taste of a hot, throbbing cock, the gush of warm cum, and the sluttiness of being fucked.

It is not like you can just go back to having sex only with women. You cannot delete the memories of such intense experiences. Once you’ve sucked and fucked a man’s cock, you’ve changed something inside of you. You may become bisexual, but you will always feel the need to express your feminine side.

There simply was nothing else as sexually exciting. It was addicting.

It didn’t seem to be about being gay so much as getting in touch with the feminine side, maybe too much in touch, but I never had this much fun as a man. Being a girl, even only temporarily, is an amazing and thrilling experience. Since I am also small, slender, naturally smooth, with refined features, I can come across as more feminine than if I were big and hairy.

I enjoy being looked at, admired, caressed, touched, seduced, and sometimes made love to, sometimes fucked like a cheap whore. I like it when someone says I’m pretty, or sexy, or cute. I like it when they call me “honey” or “sweetheart”. It’s weird.

I love it when men make me feel like a woman; I love how they get all hard when they see me. I like being touched, especially on my bare ass, and being seduced and undressed.

If you are out there reading this and fantasizing about doing the same, but lack the nerve, don’t let fear and cowardice rule over you, lest you wind up feeling deprived, frustrated, angry, and bitter. You have nothing to lose but your fear and inhibitions. If you try it and don’t like it, then you will be free of those desires. If you try it and do like it, they you will have something to do that will give you pleasure beyond belief. It’s a win/win proposition.

At the very least you will have experienced a great adventure. If you do nothing, you will only have regrets. The more you repress an urge, the stronger it becomes. That’s basic psychology. And why repress sex? Whom will it hurt? Life is short; too short to waste on unsatisfied longings.

You can deny wanting these things, but that won’t make those desires disappear. You need to honestly confront, then accept yourself for who you really are, not who you wish you were. Self-denial is worthless. Allow your inner woman to express herself. Why not enjoy life? Will you really let social conventions, or your own timidity, dictate how you live your life? It’s innocent fun; why not enjoy it?

Fantasy isn’t enough. Live your urges, don’t deny them. If you don’t, you will always wonder what you have missed.

***

I will continue this narrative, so stay tuned.

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