Submitted Anonymously
The arrangements had all been made ahead of time. My wife had already left for her weekend with the girls and I was on my own and ready to realize a fantasy I had been dreaming of for years. I had always led a straight life, and women had always been at the center of my lusts, but for as long as I could remember, I had had a fascination with women's underwear...the way it looked, the way it felt, just thinking of that slippery satiny material always gave me an immense hard-on, and most of my masturbation fantasies centered around lingerie. I had even gone to the extent of confessing my obsession to my wife, who, to her credit, accepted my "peculiarity" with as much grace as possible, but I could sense her discomfort with the subject and had let it drop...we both knew about my fascination and we both agreed not to talk about it, but now I had finally made up my mind to explore my fantasies to their full extent, and my wife's absence for the weekend gave me the opportunity that I had been waiting for the past ten years.
I had seen the ad in the local "alternative" newspaper in the "Business Personals" section..."Sandra...understated and understanding. For the inner man waiting to come out...cross-dressing my specialty, first-timers my purpose." I called her that afternoon.
I told Sandra on the phone about my continuing fantasies, about wanting to feel those beautiful sexy underthings against my skin, how at times I even dreamed that I *was* a woman, but how I realized that I was a man in every sense, both physical and mental....and yet...
We arranged for me to go to her flat on the Friday evening...I must have circled her block a dozen times before I could summon the nerve to park in front of her building and ring her apartment. Riding up the elevator I felt as if I was going to pass out...that my heart was going to burst, it was beating so fast from the sheer excitement and terror of having come so close to realizing my deepest, darkest fantasy, but I *had* come this close and I couldn't back out now!
With my hand trembling so much that I could hardly make a fist, I knocked on her door. It seemed that I stood there for hours waiting for an answer, but mere seconds later the door opened to reveal a beautiful woman standing there in a satin house coat tied at the waist, and open just enough to show some cleavage and a black, lacy bustierre. Her blonde hair spilled down past her shoulders and her blue eyes sparkled as she smiled and invited me in. "Hi Todd...I'm glad you could make it...a lot of guys lose their nerve and never go through with the appointments they make.", and taking my coat, she offered me a drink...to calm my nerves. Despite having dreamed of this moment for years, and having played the scene out in my fantasies over and over, now that it was happening I found myself completely lost and, sitting dumbly on the couch, gratefully accepted the preferred drink. The trembling of my hand caused the ice to rattle in the glass and I quickly set it down on the table...after emptying it's contents.
Sandra sat beside me and allowed her house coat to fall away from her legs, revealing a hint of her wonderful form, and for a moment I forgot why I was there and thought more of getting her *out* of her panties than getting me into them, and she, sensing that I wasn't nearly as nervous began to ask me about why I was there...how long I had known that this was what I wanted, and just generally trying to put me at ease while getting down to business. After another drink she led me to the bathroom and told me to take off my clothes and get in the shower. She had me wash thoroughly with scented soap, then when I was through she turned off the shower and poured a bath. I figured I was already about as clean as I was going to get, but she told me to just relax in the warm soapy water and let her do what she had to do...she was the expert after all! I barely said a word when she asked me to put my leg out over the side and covered it with a soapy lather...I could tell what she was up to. In order for me to fully realize my fantasy I had to go along completely and while a voice screamed in the back of my head I sat in the tub and watched her shave my legs! It was if I was watching the entire episode from a distance, my common sense telling me that there was no way I could explain a hairless body to my wife, but my brain was now about three feet away from the part of my anatomy that was doing the thinking and I just lay back and reveled in the feeling of my smooth skin and my throbbing erection.
Once my body was entirely devoid of hair Sandra handed me a towel and ducked out of the room, only to return a moment later with a box under her arm. She set the box down and removed the lid, then withdrew a pair of panties. They were dark blue with a floral print and lace accents and she held them out to me, but as I reached for them she gently pushed my hands aside and bent down in front of me holding the panties open and told me to step into them. It was unbelievable! She slowly raised the panties up my legs and around my waist...they felt incredible, smooth and slippery and conforming to every contour of my body...it was all I could do to keep myself from coming right then, but that was only the beginning! Sandra then removed a pair of matching garters from the box and fit them around my waist. These were followed by black sheer stockings...the kind with the seam up the back, and as she rolled each of the silk stockings up my smooth legs I could feel every fiber of my skin tingle with the sensation and excitement! But there was still more! The last thing she took from the box was the matching bra for my ensemble. I felt rather strange, not really having any reason for a brassiere, but Sandra no sooner had it fastened around my chest then she produced a pair of breast forms and inserted them into my brassiere.
Looking at my body, it was almost possible to believe that I was looking at the figure of a well endowed woman...if you could get past the huge bulge in my panties and the face above it all. The bulge was something I had to live with Sandra said, but as she led me into her bedroom and sat me down at her night table it became clear that she had designs on altering my face to more closely fit the rest of the picture. She had me face away from the mirror as she began applying my makeup, first a base to cover the shadow of my beard, then the rest of the colors and contours that would hopefully make me less masculine and continue my transformation...but I wasn't exactly optimistic. After about fifteen minutes of Sandra's ministrations she announced that she was done, but before I could look in the mirror to see the results, she turned me away from it and led me to the other side of her room where she had a dress waiting laid out on the bed. It was long and slim with a high neck and no sleeves and fit me like a second skin, smoothing out my shape and emphasizing my new bustling...I loved it, but I still hadn't had a chance to see how I looked in my outfit. I felt incredibly sexy, but I was sure I still looked like a man in women's clothing...not exactly the most appealing of pictures but as I started to voice my fears Sandra hushed me and pulled the final piece of my outfit from her closet. It was a long, full chestnut wig, covered with waves of curls and she immediately set about fitting it to me and combing it into shape. After an eternity of her primping I couldn't wait anymore and moved across the room to her full length mirror and what I saw almost floored me. Staring back at me was a beautiful woman, complete with face and hair and form, and I immediately felt as if a question that had been nagging at me my entire life had just been answered. This was who I was...every bit as much as the man I had always been, the woman in the mirror was somehow also me.
Confused, but still excited I turned around and around in front of the mirror, looking at myself from every angle and marveling at the work that Sandra had done. Part of what had kept me from trying this years ago was the fear that I would look ridiculous as a woman, and that that part of my fantasy life would be forever ruined by the reality of my appearance, but what I saw in the mirror was more than I had ever hoped for...I *was* a woman now and I would defy anyone to tell otherwise!
I had been so wrapped up in my new self that I hadn't even noticed that Sandra had left the room, but when I looked around she was nowhere to be seen, so I went out to the other room to find her sitting on the couch talking to another man!
This was not in my plans! There was no way I was ready to be seen by someone else this way and I turned to leave the room, but Sandra saw me and called me over. "Linda, I'd like you to meet Mark" she said. "Mark is the man I told you about and he's eager to get started." And as I stood there dumbfounded he walked over to me and took me in his arms and kissed me...deeply, his tongue reaching into my mouth!
I didn't know what to do! Here I was, dressed up to look like a woman in the apartment of a professional prostitute being passed off as another hooker! Even as Mark began to run his hands up my sides to my breasts I stood there too dumb-stuck to move and before I knew it Sandra had joined in and had begun undoing Marks pants and shirt then she took my hand and placed it on his massive cock. He immediately began to swell in my hand then he broke his grip on my rear end and, placing his hands on my shoulders, began urging me down to my knees before his huge cock. And huge it was! My hand barely fit around the shaft and the head looked almost as big as my fist! I couldn't believe that I was staring at another man's cock from no more than six inches away, down on my knees and feeling my head being pulled ever closer to it! Worse...I was turned on! As Sandra rubbed my back and sides I began to slowly stroke up and down on Marks huge pole, working it's entire length through my fingers and exploring it's contours, but soon his pressure on the back of my head increased and I found myself with my cheek rubbing against his shaft. His skin was smooth and hot and incredibly sexy and in moments I was taking my first tentative taste.
I began at the base of his huge erection, slowly licking up it's entire length then going back down the opposite side, making sure not to miss any of that hard, beautiful flesh. I could tell that I was doing it well because Mark began to breath more heavily and every now and then would let out a soft groan of pleasure. I continued to lick his entire shaft until it was all soaked and gleaming from my saliva, then I approached the massive head and slowly began to take it into my mouth. I could barely get it in, but I had become almost crazed by the thought of getting it ALL down my throat and started working it in and out of my mouth, taking a little more with each stroke and feeling it go deeper into my throat. Marks hands were on either side of my head now and he was beginning to thrust his hips towards me, fucking my mouth and getting more of his shaft into me every time while I filled my hands with his ass cheeks urging him on. I was in heaven...feeling more like a woman than I had ever dreamed possible and realizing that I had not really wanted to *look* like a woman all those years...I had wanted to *be* a woman and now that dream was being fulfilled. While all this was going on Sandra stayed behind me, gently stroking my sides and back and rubbing her ample breasts against me but my world was now in front of me and I continued to lick and suck on Marks massive cock, not really paying much attention to her, but when I felt her lift my dress up around my waist and begin to rub my ass through my panties. I began pressing my butt towards her and now found myself on all fours, refusing to give up my death grip on Marks cock, but enjoying the attention I was receiving from behind as well. Then Sandra slowly pushed my panties off to one side and began kneading my ass cheeks in both hands. It felt great, but suddenly I noticed a pressure against my rectum and felt my cheeks spreading apart. I tried to call out, but Mark's thrusting was becoming more urgent all the time and his grip on my head was like a vice. There was nothing I could do as Sandra began to slowly force the dildo up my ass. At first I thought it was going to rip me open...it must have been huge, but Sandra had lubed it up really well and, with her insistent pressure, it began to enter slowly but surely deeper
into me. The initial pain was fast passing and as Sandra pressed it deeper into me I found myself again pressing back towards her, reveling in the sensation of being filled from both ends, and giving pleasure to these two b, beautiful people. The two of them formed a rhythm so that as one was withdrawing from me the other was entering, and I felt as if I was being rocked back and forth, impaled on these two huge phalli' and I began to orgasm just as Mark drove his cock to the back of my throat and jetted a huge stream of cum down my throat. I swallowed as much as I could and pulled him towards me but my own orgasm had completely taken over and my entire body began to convulse in the most extreme feeling of ecstasy that I had ever experienced. It went on for what seemed like hours and Sandra continued her rhythm in and out of my ass as I nursed Marks still throbbing organ in my mouth. Though he had been in my mouth for almost twenty minutes and shot a huge load into me I still wanted more and continued working his shaft until it was once again huge and throbbing. I was terribly disappointed when Mark pulled out of my mouth, I was still so hungry for his huge cock, but he gently put his hands on my waist and began to turn me around, then put me back on all fours and proceeded to pull my panties down just enough to get at my still lubed ass. Despite his huge size I took him easily and enthusiastically, Sandra's strap on cock had paved the way and made me eager to have the real thing. I began to move towards Mark in time to his thrusts into me and I could feel his large hands on my hips helping to keep the rhythm, meanwhile Sandra had moved in front of me and began asking me "Is this what you wanted when you called me? To really be treated the way a woman is treated and feel the way a woman feels?" And as
I moaned my agreement to her Mark made one more huge thrust into my ass and once more began to spasm in the throes of orgasm. The feeling of his throbbing, spasming cock in me was so intense that I again had a massive orgasm and collapsed, spent on the floor. I couldn't believe the intensity of my orgasms...it felt as if my entire body was alive with electricity in a way that it had never been before and I knew that I would be seeing these two again...and often. Now my double life was complete...I still had my beautiful and sexy wife with whom I would continue to have a wonderful and rewarding sex-life, but now I could also answer that inner voice that had been calling me all my life and beckoning me to experience a different kind of pleasure, the pleasure that can only be experienced by a woman giving and receiving pleasure in return from a man.