With Tracey the Transvestite, my first time.
This was the first of four encounters that I had with Anthony/Tracey. The other three I have titled "The shower", "Both as girls" and "Dicktation in the office". If you like this story and would like to hear the others, or if this situation appeals to you, please write to me at candy4mom@yahoo.com
I have always admired men who are brave enough to go to public places when cross-dressed, admired their courage and admired their bodies. A couple of months ago I was browsing in the ladies clothes department looking for something to buy my wife for her birthday, when I noticed a good looking woman browsing the rack in front of me. When she turned around my heart leapt, either here was a woman with a very uniform shaving shadow and large hands, or here was my living fantasy.
He noticed me staring at him and smiled at me nervously, I found out later that he thought I was offended, how he was wrong. He moved off towards the lingerie section and I followed, stomach in my mouth. I was determined not to blow my chance to at least talk to him. He could not help but notice that I was following him and, when he was facing me over a rack, said "Hi". I almost died. He put on a husky voice that made my cock instantly harden with lust. I gathered all of my courage and replied "Hello, I must say that you look fantastic". What a stupid line, I thought, I am an idiot. But he did not think so and thanked me for the compliment. He then picked out a red satin teddy from off the rack and asked me what I thought of it, I told him it would look great on him. He smiled again and asked if I would like to make sure he has made the right selection. With my voice shaking with nervousness I replied, "very much so".
I walked with him as he finalised his purchases and we went to a nearby coffee shop and sat in a corner. We ordered coffee and just sat there for a while, both too nervous to talk. After our coffees came, we exchanged small talk, his name was Anthony but he liked to be called Tracey when dressed, he was in his late 30's and a clerical manager for an office in the city. He said that he did not live far from here and asked if I would like to come back to his house to help him try his new clothes on. Shaking like a leaf, I said yes.
Tracey gave me the directions and we both headed off to our cars and drove to her house. I admired her long, slender legs as she stepped out of her car and walked up the path to her door. After letting me in, she gave me a tour of her house, it was very non-descript with nothing overly feminine about it. She explained that she had two bedrooms, one was Anthony's and one was Tracey's. Taking my hand she led me to Tracey's. It was a big room with a classic Queen Anne bed in the middle and dresser that was covered in make up and wigs. Tracey opened the wardrobe to reveal a stunning collection of dresses and asked if I liked what I saw. I replied yes as she looked long and deep into my eyes. Tracy leaned forward and kissed me lightly on the lips, I smelled her perfume and almost fainted with excitement. I returned the kiss and we embraced passionately.
As we kissed our hands explored each other's bodies. I felt her tight, curved butt and thin waist and her hardness pressed against me, I wanted her so bad. She slipped her hand in front of me and cupped my balls as she forced her tongue down my throat, I almost came instantly. We broke our embrace and Tracey told me to relax while she put on her new clothes. I sat on the bed with butterflies racing in my stomach, I could not believe this was happening. My cock was rock hard and oozing pre-cum and my whole body was tingling with anticipation. I prayed that she wanted me as much as I wanted her.
Tracey returned to the bedroom dressed to thrill, almost a picture perfect replica of the object of my fantasies. She was wearing a blonde wig that fell in curls over her shoulders, large gold hoop earings, very well done makeup with blue eyeshadow and full ruby red lips. Around her neck was a black velvet choker with a pink cameo in the middle. Tracey was wearing the red satin teddy that she had shown me at the store, under the teddy was a black lace garter belt holding up black, seamed stockings. She had elbow length lace gloves on and, in the perfect final touch, black stilleto high heels.
Tracey was sex on legs!
She smiled at me and asked me if I was okay as I was a little flushed, I said that I was fine but about to explode, she was so beautiful. Tracey strutted towards me and asked me to stand, as I did she kissed me hard on the lips and then blew softly into my ear, my cock jerked and it was all I could do to stop from cumming. She unbuttoned my shirt and pulled off my T-shirt, then undid my belt and, in one movement, slid my jeans and underpants down. My cock sprang free and pointed straight up. I stepped out of my pants as Tracey pushed me gently down onto the bed.
She knelt over me as I stared up into this wonderful sight. She started to rub her breasts and I saw that her cock was straining at her teddy, this was the closest I had ever been to another cock, and I wanted to get a lot closer to this one. Tracey parted her lips and moaned, then leant forward and we kissed before she started to kiss her way down my torso. She kissed, licked then sucked each of my nipples bringing them to firm erection, all of the time she was doing this she was stroking the inside of my legs with her gloved hands. I was moaning like a bitch in heat, all traces of butterflies gone, all I wanted was Tracey.
After what did seem like ages, Tracey took my cock in her hand and then into her mouth. I looked down to see myself being sucked into that ruby framed velvet mouth and I exploded, sending cum down her throat. Tracey swallowed most of it, but held a mouthful as she let my cock go and moved up to kiss me. She passed my come back to me and I tasted myself for the first time. I cannot say I liked it but swallowed anyway, it was not too bad and I was so turned on that I would do anything Tracey asked of me.
We lay on the bed kissing and stroking each other, Tracey guided my hand down to her cock. I felt her hardness and reached into her teddy and pulled her cock free. Tracey has a thin 6 inch cock (a bit smaller than mine) with a perfect circumsised head, I could not wait to taste it. I moved down the bed until her cock was against my cheek, I licked her pre-cum and enjoyed the taste, very sweet. I opened my mouth and her cock slid inside, I was in heaven! I did not imagine just how good this was going to feel. Her cock fitted perfectly inside my mouth, I loved the heat from her body as I ran my tongue around the soft fleshy head of her cock and started to suck. I found it difficult not to use my teeth at first so I let her cock fall out of my mouth and started to lick and kiss it like a popsicle.
Tracey was moaning in delight and was lifting her hips off the bed towards my head, so I took her back into my mouth, as I did she placed her hands on my head and pushed me down onto her cock. I felt her expand to fill my mouth as her breathing grew hard and heavy. With her hand holding my head firmly down and my nose buried in her neatly cropped, purfumed bush, Tracey started to fuck my mouth. The head of her cock suddenly expanded and her come poured out of her and down my throat. I gulped and gulped as she came and came, unlike my own, Tracey's come was thick and sweet and felt great as my mouth was soon filled and some dripped out over my lips. I thought to myself how good it will feel to have her come deep inside my ass, dripping out of my hole after she has made love to me.
I sucked on her cock as she started to go soft in my mouth, but Tracey pulled me up her body to embrace me in a long kiss. We lay side by side gently kissing and stroking each other, enjoying our love making. My cock was rock hard and pressed against Tracey's thigh, she reached down and took it in her gloved hand. As she stroked me she looked into my eyes and whispered "make love to me", I was so excited that all I could do was croak "my pleasure" in reply.
Tracey reached over to the bedside table and took a condom from the drawer, after opening the packet she slid the sheath over my cock, kissing it when she finished. Tracey then rolled over and got onto her hands and knees, before reaching back and un-clipping the clasps of her teddy to expose her creamy rounded ass and delicate bud-like hole. I knelt behind her and marvelled at the sight before me, her blonde hair was flowing over her wide shoulders and her red teddy was framing her torso and beautiful ass. I could not resist this opportunity and reached forward to kiss her ass and run my tongue over her hole.
Tracey moaned in delight, encouraging me to go further. I lapped at her hole like a dog at a bowl before spreading those magnificent cheeks with my hands and pushing my tongue into her. She squealed with pleasure and pushed her ass into my face as I forced my tongue as far as I could into her ass. I reached around and took her now hard cock into my hand, and started to stroke it. After making sure that she was wet, I kissed her ass once more before kneeling up and gently pressed the head of my cock against her ass hole.
With encouragement from Tracey I pushed my cock slowly into her magnificent ass. There was resistance at first, but once the head went in I was able to slowly push my entire length into her. Once my balls were up against Tracey's ass cheeks I paused and basked in the wonderful sensations I was feeling with my cock up this great ass. Her ass was so tight and warm that I thought that I would explode right there and then, after I calmed down a bit I started to slowly fuck Tracey.
My cock slid in and out of her hole with increasing ease as we both moaned in pleasure, I grasped her thrusting hips as she started to toss her head around in ecstacy. The sight of my cock sliding in and out of her hole, her hair whipping around her shoulders and her body jamming backwards and forwards was too much for me, I shot my load deep into her as we both collapsed onto the bed.
I remained on top of and in Tracey as I kissed and gently bit her neck until my cock grew soft and popped out of her ass hole. I peeled the condom off as she turned to face me and we embraced. Her face was flushed red and her eyes were on fire. Her cock was hard and glistening with pre-cum, I saw that and knew that now was the time I had been waiting for. I asked Tracey to fuck me gently and so that I could see her do so. She kissed me and asked if it was my first time, I replied that it was and that I wanted the full experience. She said she understood and rolled me onto my back and asked me to place a pillow under my ass.
She then knelt between my legs, my cock was getting hard again at the site of this gorgeous creature getting ready to fuck my virgin ass. She reached over to the bedside table and took a tube of lubricant and applied some to my ass and her cock. My hole contracted on contact with the cold gel but Tracey started to rub the gel over it with her finger until I relaxed from the wonderful feeling that it was giving me. I felt her finger probe my hole then slowly slide inside and twist around, that felt so good! After a minute or so she slowly inserted another finger inside me and then another so that I had three fingers inside my ass, stretching my hole.
I was squirming and moaning like a bitch in heat, I felt totally feminised and exposed and I wanted more, I wanted the main event. I moaned for Tracey to make love to me and fuck me like a girl, she smiled and withdrew her fingers and moved closer to me so that her cock pressed against my hole. I felt the pressure increase as she tried to push herself inside of me, her finger work had done the trick as I felt the head of her cock enter me. I squealed in pain as I felt I was being torn in half, Tracey stopped pushing, leaned forward and kissed me hard on the mouth forcing her tongue against mine. As I returned her kiss I forgot about my ass until she broke from our embrace and asked me if that felt alright.
I then realised that when we were kissing she had pushed herself completely inside me and I was lying there with her cock buried deep inside of me. I was finally being fucked and in the way that I always fantasised about. I shouted that I loved the feeling and Tracey started to slowly fuck me, sliding her cock in and out of my ass hole. She took my legs and put them over her shoulders causing me to gasp as her cock penetrated deeper than before, I could not believe that this felt so good, I loved the feeling of her cock filling me up and I loved the feeling of being totally fucked by this beautiful, sexy man,
Tracey's breath grew hard again and she started to fuck me harder and I knew she was near climax. She grabbed my hips and pulled me against her as she thrust her cock as deep as she could inside me. I felt her cock expand to completely fill me and then spasm and I felt her hot come inside my ass, I almost fainted with pleasure. We stayed motionless apart from Tracey's cock as it continued to pump it's load into me. My ass filled with her come until it could hold no more and come started to drip from my de-flowered hole.
Tracey slowly pulled her cock out of my stretched ass hole and then knelt down and started to lick her come from out of my ass. This was too much for me and my cock exploded sending streaks of come over my chest and neck. Tracey leant forward and cleaned me up with her tongue before collapsing next to me on the bed. We embraced in a long kiss and drifted off to sleep in each other's arms.