My Excursion Into Womanhood

Published on Oct 28, 2009

Transgender

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This is a total work of fiction.

At 5'4" tall, and 138lbs, I was often found to be very desirable as an oral bottom to the several dozen men I'd orally pleasured the past 20 months. Men....especially large men......often found me to be erotically submissive and a "real pleaser" when I lovingly took their cocks into my mouth and worked them to their finish. My lips, tongue, hands....all seemed to work in unison from the small man kneeling between the knees and thighs of horny virile males who just needed to "get off" as quickly and simply as possible.....with no strings attached. And I just loved my experiences with men. At 70 years of age, very healthy, fit, athletic, a former long-distance runner, married for over 40 years, and "regular" or "normal" in all outward appearance, I was experiencing a side of my libido that I felt confident that absolutely no one knew about.

But while I'd immensely enjoyed the m/m oral pleasures I was giving to men, I'd begun to yearn for even more intimacy with the men I'd been getting to know in such a deeply personal way......thrilling them to sexual climax inside my mouth and completely swallowing their semen. It was no longer meeting my sexual needs. While I was enjoying it and emotionally receiving a great deal of warmth and pleasure from it...especially when men thanked me profusely and warmly....and sometimes even offering to return the favor, which I occasionally accepted from them, I still wanted them to appreciate me even more deeply.

Occasionally, when performing oral sex on men, I'd been treated as a feminine servant by some of the men. They'd often referred to me vocally by using terms of endearment that a man uses to express love, tenderness, joy, lust, and even contempt to a woman. At first I found such address to me offensive, but tolerable. It seemed to me to be the way some of the men were able to best express themselves while aroused or building arousal to the final point of sexual orgasm......and I certainly wanted that orgasm of theirs to give me the prize of their semen so that I could enjoy it spurting and flooding my mouth, after which I eagerly swallowed it for the deepest and most intimate male bonding I had ever experienced......the swallowing of a man's seed...a man's sperm which resided in the bath of his seminal fluid. All of the accompanying behavior of the man who was cumming.....his moans, groans.... trembling, wriggling, grabbing at my hair, rubbing my head, rubbing my back, bucking, bellowing, breathing erratically .......all were icing on the cake as I enjoyed the deeply personal act of making a virile man ejaculate inside my mouth, as he lost control of all senses but the sexual. At that time he was all mine.....needing, wanting, and loving me in his lust, temporary as it often was and must be. His occasional references to me as his honey, baby, or even as his bitch were proof to me that he enjoyed me both as a man and, perhaps, even more so as a submissive man/woman.

But being treated as a feminine object, rather than as a man, because I was servicing men who viewed a blow-job as a woman's "work" really began to turn me on more and more as I continued to "do" men the past year and a half. I began to get turned on by the thought of men looking at me and lusting for me because I was small, submissive, and a "giver" of pleasure....a woman's role, as it were. Finally, I had reached the point where I wanted to "go all the way" as a woman. I wanted to be fucked. My legs were strong, short, but quite slender and lean....even femme. If they were shaved they'd be quite attractive to a man, I thought. One man, while 69ing with me, had kissed them very passionately and referred to me as sweety and my legs as being beautiful as he wetly kissed my thighs and my knees like they'd belonged to an attractive woman. Being treated as a woman had been extremely erotic to me, and I quickly began to think about the ways in which I could behave, appear, and express myself to become even more desirable and exciting to men with whom I was seeking sexual pleasure and intimacy.

I began to think about crossdressing, wearing makeup, and simply meeting men on that basis....to let them have me as they'd take a woman for love and/or sex. Of course, taken to it's logical conclusion, this all meant that i was going to have to allow myself to truly go "all the way" and submit my entire body to a man for his sexual gratification. It meant I was going to have to let men fuck me anally. I was ready. I really wanted that. When I'd met large burly men...."bears," to suck off, I had urges to be taken forcefully and totally. I wanted to hear those men as they reached a climax inside my ass and clung to my hips and torso as they bellowed out their cries of ecstasy and poured their semen inside me. I could think of no more intimate and bonding experience between two men. It was great when they behaved that way while ejaculating inside my mouth, but it didn't seem like it would if it was inside my ass.

I was now prepared to enter a new dimension of sexual experience. I knew that now I would be wanted to kiss a man and respond to a man just as he expected a woman to do. Oral intimacy was now going to involve lips and tongue on and inside a man's mouth, and the willingness to experience a man's mouth and taste and savour his saliva and the oder of his breath as he built up his desire and arousal to a point of no return and the immutable need to penetrate me anally to "know" me as I was inviting him to do so. All these thoughts excited and aroused me to an extreme. I now so desperately wanted a man to make love with and satisfy himself totally, like I was his lady lover. I now had to get ready to do so.

I went out and purchased high heel shoes, a dress, nylon stockings (not pantyhose), panties, some jewelry to wear, make-up, nail polish, and simply set out to look the part. I then advertised on Craigs List, in the m4m casual encounters section for a bearish man who wanted a femme cross dresser who would give him whatever he wanted. I was sure to include in the ad that he was getting a bonified "virgin" to take anally, and that he must be gentle with me at first. I couldn't host, so either he must, or a room had to be procured. I then waited for a response. I got about 20 within 3 hours, and I finally settled on one which I thought would be right for me.

His name was Ben. He was 52 years old, 5'11" tall, 225 lbs, married, white, slightly graying short hair, brown eyes, generally fairly hairy, cut, just under 7", and, as he put it, a "heavy cummer." He sent me some photos of himself, mostly in the nude in various tasteful poses. I was very aroused at his masculinity and gerth. He was a man by whom I wouldn't be able to help but be feminized. Even without cross dressing, I felt feminine while just looking at the pics he'd sent me, and imagining being with him for sexual intercourse and all the foreplay that it would entail with me dressed up feeling and behaving fully femme. I so wanted Ben to be my lover....totally. Strange and kinky thoughts began to emerge from my mind, irrational thoughts.......like the thought of being inseminated and bred....having this virile man's child. I could hardly wait for our first time together.

The time finally arrived, and to simplify things I'd made a room reservation at a hotel central to both our dwelling locations. I was fortunate in that my wife was out of town visiting some close relatives of her's, so I could make a night of it with Ben. We both arrived at the hotel at around 6pm. I was carrying a light overnight bag in which all of my change of clothes were, along with make-up and various other implements that I hoped would transform me into a passable and sexually attractive feminine figure for my lover to be. I'd shaved my legs and other portions of my body to minimize the masculine aspects of my body as much as practically possible. I'd done this without even giving thought to my wife noticing the change after she'd return from her trip. But at this point, I didn't care or want to distract myself from what I was about to have happen to me with Ben, so I put it all out of my mind.

Ben also carried an overnight type bag. Like me, he was dressed very casually, although unlike me he wasn't wearing short pants. He immediately spotted me and smiled while looking me over up and down my figure. I looked at him and sized him up in a similar manner. He was a big man....a very domineering figure compared with me. The sight of him immediately aroused me, and I was hoping that my diminuitive figure was doing the same for him as he imagined what he would be doing with and to me.......especially when I made myself far more femininely presentable and alluring. I so wanted him to fuck me....plain and simple. I wanted him to implant his seed inside me and enjoy me to the fullest. I wasn't going to spare any effort to make him feel all of the man that he could be with me as his lover. I was even now falling in love-lust with Ben, and I wanted him to desire me so very much. I could barely contain my lust.

He extended his hand and we shook hands. I felt his tight manly grip, which I returned demurely, as I didn't want to appear masculine to my man. I wanted him to think of me as the "weaker sex," from the very start....even though not yet dressed as such. I quickly told him the room number, and we both walked to the room for which I had a key-card. AS soon as we got inside the room, Ben put a hand on my shoulder and gently stroked my back. I turned to look up at him and he immediately bent downward and found my lips with his. I was taken aback by the suddeness of his kiss, but I quickly responded positively and we began to kiss passionately as he drew me close to his massive chest and torso. I was now already being perceived as the lady he was going to receive pleasure from and to whom he'd give his love this night. And I was willing and able to return all in kind.

We gravitated towards the bed while our kissing and fondling proceeded for several minutes. He was aroused and tentiing in his pants, as was I. I broke our kiss and said "I want to make myself look nice for you, Ben." He smiled and said, "yes, Francie. I want to see you as beautiful as you can be." With that I retired to the bathroom and began my transformation into all the woman that I could be. Nylons stockings, panties, a padded bra, a one-piece dress, make-up that included powder and lipstick along with eyeliner...all the trappings a woman used to be alluring to a lusty man, and finally the high heel shoes. I thought I was a "knockout" as I observed myself in the full-length mirror. My shaved legs looked so very feminine through my nylon hose, and as I posed and moved my body I was now sure that he would "like" me.

As I exited the bathroom and came into Ben's view I could hear him catch his breath and sigh as he beheld me fully dressed as his "lady." "Oh, Francie," he uttered somewhat breathlessly, "you're beautiful. Come here and let me see and touch you. I sauntered over to him in as lady-like a manner as I could move, and he quickly embraced and began kissing and caressing me all over. He was now in his boxer shorts only, and his masculine hairy body had me completely weak-kneed as he passionately kissed, touched and embraced me. He was so very aroused by me. His arousal was contagious and I was now as horny for him as he for me. I began to kiss his chest and shoulders as he kissed my head and the back of my neck. Our mouth kisses were very deep, wet, and passionate as we exchanged saliva copiously. His taste was intoxicating to me, and I was so very surprised to my reactions to making out with a man. Kissing men before had been more a prefunctory duty than a joy. Now, with Ben, it was a necessity for me, so that I could express my lust and need for his body to possess me and merge with mine's......to become soulfully as one with him.

"Oh, Ben, Ben," I cried out to him. "I need you. Take me. Put it in me, please. Fuck me, Ben." With that I "went down" on him and began to suck on his hard dripping penis as I slipped off his boxer shorts. He was so wet.....and big! "Francie, I'm ready to give it to you good, sweetie," he whispered while out of breath from the pleasure of my sucking on his cock. I looked up at my lover...now my love, and I made longing eye-contact with him as if to say "I'm all yours, Ben. You can take my virginity at will.....I'm here just for you. He understood. He raised me to my feet and began to lift my dress and tug at my panties. They easily slid down my smooth shaved nyloned thighs and legs. Suddenly I felt very shy and vulnerable to him. I moved back as I kicked away my panties, and I sat in a chair across from Ben and shyly and little girl-like.....still wearing my high heels...... I crossed my legs and smiled...almost blushing. At that sight he was beside himself in lust and desire to "know" me....know the mystery of my body and libido. He wanted to penetrate me and transfer his seed to me as he expressed both his love and lust for me. I was in a total state of womanhood now. I felt just like I knew a woman must feel in the same situation as she's about to submit to a man's desires for her.....about to be revealed to him and discovered by him in the most intimate and deeply personal way possible. I was going to bring him to orgasm and submit to being exposed to his precious seed. And I was going to love him ever more for it.

I crossed and recrossed what I now believed were my beautiful legs. Each time I did so Ben would get an eyefull of my "private" parts. He was erect, wet, and ready as he squirmed on the bed's edge. I was wearing jewelry which flashed and caught his eyes as I moved my hands to motion to him that I wanted him so very much. I then arose from the chair and moved to Ben to hold him and allow him to hold me as we resumed passionate wet kissing and fondling. Suddenly he grabbed me and picked me up in his arms as if carrying a bride over a threshold. He then turned with me in his arms and gently placed me on the bed. He said "I want you to keep your nylon stockings on, and your high heels....your dress too. I'm going to take you now, just as you are with just your panties off. With that being said he quickly got on the bed over me, lifted my dress, spread my legs and placed my feet over his big shoulders and mounted me as though I were the woman I now so wanted to be for him. He began to hump me as his cock and balls rubbed with my like parts and slid around each other from our oozing precums. He was so manly! I was being kissed and manhandled by a hunk of a man.....a lusty potent man. I so wanted his semen to flow into my body now. We kissed ever more passionately. We liberally swapped spit and sucked on each other's tongues as we mutually probed and learned about each other's mouths. It was so wonderful! I was merging and bonding in the most intimate way I could think of....with a real man.

"I want to cum inside you, Francie," Ben blurted out as his breathing and sweating increased from his building lust. "Oh, yes, yes, Ben," I cried out. "Fuck me. Make me all yours now. I need you. I want it, now." With lust and determination in his eyes, Ben looked deeply into my eyes and said "You're really going to be taking my cum, sweetie. I've got a big load for you....it's just for you dearie." He then reached over to the night table and took hold of a tube of lubricant to begin applying it to my rectum and all around the head and shaft of his erect penis. He did it quickly, and then returned his gaze to my body beneath him....deeply searching my face and my eyes for the reaction to his penetration as he slowly pushed inside me....gently, slowly, steadily, and I then felt his crown moving past my sphincter muscle. He was coming into me....my lover was taking my "cherry." It was so personal ...so intimate, and wonderful. I let out a sigh just as he did. We were in unison with our desires and expected pleasures. In almost no time at all he'd pushed completely inside my rectum. I felt full of my lover. He was filling me both physically and emotionally with his manly countinance. I was about learn what it was to be inseminated.....just like a woman who belongs to a man learns so very quickly when she's fucked for the first time. There'd been pain, at first, but it was over very quickly. My lust had simply overcome any pain that had begun, and just as quickly gone away.

Ben began to move...to thrust. At first slowly and with short strokes, but soon longer and longer strokes as his speed began to pick up. Each time he pushed fully inside me I thrilled to his violation and growing knowledge of me....my reactions, my growing love and lust for this virile man. I was totally becoming his now. My legs were draped over his shoulders, and he bent down to meet my mouth with his as we continued our dance of love. His wet kisses were intoxicating as I felt his complete manhood deeply probing the core of my small willing body. Every now and then he'd straighten up and look over my body...my nylon stockinged legs, my high heel shoes, and the dress pulled up to my chest while his hard cock implaled me deep inside my ass. Then he'd resume his loving of me. Thrusting, kissing, gently biting my neck and my shoulders. I reached out to him and held his face and head in my hands as I thankfully gazed into his lustful eyes. My cock was wet and hard, and his was feeling so good sliding along my colon. I was near cumming, and I could feel the growing gerth of his penis as it neared a climax.

Then it started to happen. Ben's breathing was becoming more erratic, and his motions more rapid as he thrust back and forth. He then uttered aloud, "Oh Francie, I think I'm going to cum. Ohhhhh, my love, my lady, I'm making you all mine. I'm, I'm, oh God, I'm going to breed you my sweetie, my honey. Ahhhhhhh, aaarrgggghhhh, oooohhhhhhhh meeeeee." And breed me he did. I felt his swelling cock inside me and his final thrust as we grasped eachother tightly and trembled to what was now happening. A warmth and wetness sensed very quietly flooded my body. I was making my lover cum inside me, and I loved him deeply for it. I could feel all 5 pulses accompanied by the spurts of his seed, and then some post-spasms as he finished. It was then that I realized I'd cum as well, and that his pleasure had been just as much mine, as I'd spurted my semen on both our stomachs. Ben collapsed on top of me...in my arms, and I held him warmly and lovingly. We were now as one, and nothing could ever change this event of intimacy and love. Ben rolled over, slipping out of my body. In a quiet afterglow we softly kissed on the lips several times, and then we both went to sleep.

Frank

Comments are appreciated. frankdpr@gmail.com

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