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It all started several months ago when I posted a true story about my first (and until then, only) encounter with a transsexual beauty. After I posted the story, I got several replies from people who had read the story and liked it. One person who responded was Ann. She told me in her note that she liked my story and asked if I would be interested in corresponding. I took the plunge and sent her an Email reply. That was the start of what I will tell you about here.
You have to understand where I'm coming from. I am 44 years old now and I have been in a monogamous heterosexual relationship for 25 years. Gradually that relationship broke down and we have separated. That leaves me looking at the world in a whole different light. I began to really ask myself what it was that I desired and what it was that I wished I could experience.
Transsexuals had always been attractive to me and I had watched films and read stories about it for years. I guess I could identify with many of the issues and I found the people involved to be exciting and courageous. I wanted to know more. Then I had my first encounter with a MTF transsexual! Like I said, that is another story, but the result is that I wanted more!
So, I began to correspond with Ann via the Internet. At first we exchanged small talk and told each other tidbits about our lives and our fantasies. Ann was a newcomer to the free world, just like me.
She had recently ended a long term heterosexual relationship and was just beginning to get ready to transition to full time as Ann. She had rarely had the courage to leave home as Ann and had never been with a man, but longed to be accepted and treated like a woman. We were made for each other; both new at this world, but both eager to explore more.
Ann was trying to get started on hormone treatments after prior work had gotten her breasts to grow to respectable size. She had a goal to move toward SRS in about 5 years.
As we became more comfortable with each other, we began to share some of our more intimate desires and fantasies. The Net became the hot highway for our dreams.
We lived in different cities, but I travel a lot with my job. As it happened, I had a meeting in a city near where she lived. I brought up the idea and suggested that we meet and have a date one night. I was thrilled when Ann agreed.
On the day that we were to meet, I could hardly keep my mind on business. I found myself wandering and dreaming about what was to come. As soon as I ditched my business partners, I began my preparation for our date. I showered and shaved and put on my favorite cologne, Polo. I made sure that I dabbed a little in my pubic hair (just in case).
I dressed in my suit with a tab-collar shirt and my Jerry Garcia tie, gave my shoes a quick polish and I was almost ready. I'm an amateur magician and I loaded my pockets with five or six of my best tricks. When I looked at my watch I realized I was WAY early for our meeting. I was just so excited. So I went down to the Hotel lobby and bought myself a Black Russian to try to calm myself down a little. I was sitting there thinking about my date with Ann and the next thing I knew, I had a woody from thinking about it. Boy, I had to calm down or I was not going to last the night.
I stood on the doorstep. It had taken me five tries to work up the courage to park and get out of my car. My heart was racing and my face was burning. I held my breath and pushed the button. I could hear the bell ring, but then I heard nothing. I waited for twenty seconds that seemed like twenty hours, then the door handle clicked and the door swung open. I finally stood face to face with Ann.
Time stopped as we looked at each other for the first time. Ann was beautiful. Simply beautiful. She was wearing shoulder length silky black hair, cascading on her shoulders like Cleopatra. He skin was white and her lips a vivid red. Her eyes were deep blue and sparkling, framed perfectly with eyeliner and mascara.
She wore large gold hoops in her ears that peeked out and twinkled in the porch light through her hair. She had on a gold necklace with a single diamond pendant that nestled between her breasts. She had on a light silk blouse, decorated with shades of red and brown. It was sheer enough that I could see the outline of her bra against the fabric. She wore a dark, burnt red silk pleated skirt that ended mid thigh and sheer black stockings.
Her feet were in a pair of subdued red pumps that matched her skirt. Her long nails were painted to match her lipstick. As I stood there, frozen to the spot, I could smell her perfume. She was wearing Georgiou. I love perfume! We stood that way, looking each other in the eyes and assessing each other. Ann dropped her eyes and a small smile passed over her lips. I think she caught a glimpse of my cock, which was trying to break free.
"Hi, Rob," was all she said, in a low voice. She sounded like a seductress as the words rolled off her lips. She stepped forward and extended her hand. I knew her wish was to be treated like a lady for the night. I took her hand in mine and brought it to my lips and gently kissed it.
"I'm thrilled to finally meet you, Ann. You are beautiful tonight!" I said. Her hand was warm and I could feel her tremble slightly to my touch. I could smell her perfume very well now and it was making my heart race even faster. I invited her to join me and she grabbed a small purse from the foyer and locked her door.
We walked down the drive to my car a little awkwardly, passing pleasantries about the weather back and forth. When we got to the car, I opened her door and invited her in. As she sat, I could see she wore stockings and garter with dark colored panties. I closed her door and took a deep breath to calm myself before I got in to drive.
We talked as we drove and some of the nerves began to calm a little. I made a joke and she laughed, throwing her head back and swishing her hair back and forth. I had a little trouble driving since I couldn't keep my eyes off her body and her legs for too long. We pulled into the parking lot of a bar that Ann had suggested would be a nice place for a drink before dinner.
Ann started to get out of the car, but I put my hand on her arm. "Allow me," I said. When I looked where I had touched her, there were goose bumps. I walked around and opened her door and offered her my hand. She took it and I was rewarded with a glance up her dress as she stepped out into the parking lot.
In the bar, we found a table near the back where the light was low and we could sit together on a padded bench seat. The waitress took our order, hardly looking at us at all. Ann ordered a Margarita and I had a Black Russian. We sat and talked about everything from the weather to the president, all the while getting more and more comfortable with each other.
As we talked, a slim young girl sat at the piano we had passed while entering the bar and began to play soft romantic music and sing in a silky voice. I glanced around the bar and saw it was filled with couples and a few foursomes, talking and sharing drinks just like we were. I noticed there was a small wood parquet dance floor and a pair of couples were dancing slowly to the music. As we talked, we began to touch each other a little more. Here I held her hand for emphasis; there she patted my arm while I spoke of a past pain; now I brushed her knee; then she laid her hand on my thigh.
After a while, I screwed up my courage and asked Ann to dance with me. Her eyes opened wider for a fraction of a second and then she agreed. I took her hand and we walked to the dance floor. There was one other couple there already, and they were locked together in an embrace with their eyes closed. I took Ann's hand and we came together to dance. My arm circled her waist and I felt her hand touch the middle of my back.
The piano girl began to play and sing the old Kenny Rogers standard "Lady" and we began to rock with the music. Ann came close and I could smell her perfume like the smoke of an opium pipe, warm and inviting. She laid her head on my shoulder and I pulled her close to me. She was warm and yielded to my touch and I felt thrills course through my body.
We danced slowly and closely. Before I knew it the song had ended. We pulled back to look at each other, but did not break our light embrace.
Ann's cheeks were flushed and she smiled at me. Without a word we knew we had to dance again. As the next song began, I pulled her closer to me and let my hand stray down to her butt, lightly caressing her bottom. Her hand strayed up and down my back. I pressed her against me and I could feel her breasts against my chest. I pushed my knee against her crotch as we swayed slowly to the music and she pushed herself to my leg.
I remembered where I was then, when I felt the slightly hard swell between her legs. I didn't let go but used my leg and knee to gently pressure against her cock which was growing as we danced. Ann did the same to me and my cock was at full attention, straining at my pants. I could hear Ann's breathing accelerate and felt her lips brush against my neck. I never knew that goose bumps could cover your whole body, but I found out that the touch of her warm lips could do it to me.
When the song ended, we both knew we needed to cool down a little, so we walked back to our table hand-inhand. I glanced at her to see if there were any tell tale signs of what we were up to, but the pleats of her skirt hid any bulges that might have given us away. I however, did not have on a skirt and I'm sure anyone could have seen that I was ready to go. I felt a wet spot of pre-cum in my pants. As we sat, Ann "accidentally" let her hand brush across my erect penis through my pants, giving me another thrill. We had another drink and danced again and again. I showed her my magic tricks, cards and coins and silks. She laughed delightfully and marveled at what I could do with my hands.
Each dance became a little hotter, a little closer. I realized that we were going to get into trouble, either from drinking too much or getting it on right in the bar, so I suggested that we should probably go to dinner. We paid our bill and walked out holding hands. As I opened the car door for Ann, she stopped and cupped my face in her hands and told me I was sweet. She gave me a kiss on the lips. It was short and warm. She still held me in her hands and we separated enough to look in each other's eyes. I put my arms around her, locking my hands on her butt cheeks.
I could feel the silky panties sliding against the skirt and I pulled Ann close to me and kissed her for real. We embraced and our lips parted. My nostrils were full of her perfume and her breasts were pushed up against me as our tongues danced against each other in a deep French. I brought my left hand up and cupped Ann's breast, feeling her push against my hand as I did so. We kissed for a full minute and finally broke for air. We didn't say anything, but I handed her into her seat, her eyes gleaming at me.
The drive to the restaurant was not too far. Ann put her hand on my thigh and then let it creep up to the bulge where my now wet penis was doing its very best to escape and jump into her hands. We straightened our clothes and went into the restaurant for dinner. This was listed as the best restaurant in the area and the food and service were superb. We had wine with dinner and feasted on an appetizer and well presented entrees.
Ann declined desert and so did I. Ann said she would rather save me for desert. We talked constantly through dinner. When it was over, I asked her what she would like to do and offered more drinking or dancing. Ann said that if I didn't mind, she would like me to take her home and come in for a drink. She did not have to ask me twice.
At her home, she opened the door and led me inside by the hand. Her place was spotless, decorated with subdued modern art and low lights. She led me into the living room and invited me to sit and then went to the kitchen. I could hear her in there clinking glasses and moving stuff around. She came back with a glass of wine for herself and another Black Russian for me. She lit a few candles that were scattered about the room and I think she made sure to bend over so I could see her legs and the top of her stockings as she did so. She put some soft music to play on a stereo and turned out the lights. Ann came over to me and sat next to me on the couch.
"You have been the perfect gentleman, Rob. I dreamed about this night for years and years, but did not imagine how wonderful it really would be. I think you deserve to get what you want!" She came to me and we began to kiss. At first, we just embraced and kissed. She was warm and soft and smelled like heaven. The candles threw off soft light which reflected in her eyes and filled the room with a warm waxy smell.
I smelled patchouli from the candles that reminded me of 1970 and head shops. We kissed and began to pet. I caressed her breasts through the silk and lace of her bra for a little while. Then I slowly unbuttoned the top three buttons and put my hand under the blouse to cup her breasts in her bra. She worked my back and rubbed her hand across my thighs, but we both wanted it to last, so we went slowly.
I reached behind and unsnapped the clasp of her bra and then found her breasts with my hands. They were full to my touch and I found her nipples and gently tweaked and pulled them. I could hear her breathing accelerate. When the time was right, I broke the lip lock and nibbled at Ann's neck first and then moved down to kiss and suckle her breasts. She lay back and I slipped to my knees in front of the couch so I could reach her breasts with ease. She moaned and writhed to the touch of my lips and we kept that up for a long time, both careful to prolong our pleasure.
The music ended and I sat up and sipped my drink. Ann got up and peeled off her blouse and left her bra hanging on her shoulders. She looked at me and tweaked her nipples, pulling on them as she did so. I was ready to burst at the sight of her in her skirt, hose and bra. She stood and took my hand and said that we really needed to move to the bedroom. She invited me to lie down and suggested that I get comfortable while she "freshened up" in the bathroom.
She lit some more candles and turned out the lights before she slipped into the small bathroom at one end of the bedroom. I pulled back the covers on her big four-poster bed to find deep wine-colored satin sheets. I stripper to my underwear. When I realized how wet the front of my underpants were already, I threw them to the side as well, gulped my drink and slipped between the cool sheets. Ann called, "Are you ready?" Yes, yes, I was.
Ann came out of the bathroom with the light off and at first all I could see was her silhouette framed in the doorway. My eyes adjusted and I saw her standing there in a red lace push-up bra, lacy red high- cut panties, red garters and red stockings. She had on black shiny high heels and stood with her hands on her hips looking at me. I couldn't speak, but held out my arms to her and she came over and lay down on top of me and began to kiss me again. I rolled her to the side and began to caress her breasts while we frenched deeply. She had heard me talk about how much I love perfume and she had reapplied it liberally.
My hand moved to her thigh and I slowly slid it up to her crotch. I felt the cloth of her panties and pressed my hand into the V of her legs. There was nothing there and I was confused for a second until I found what I was looking for tucked back between her legs. She pushed against me and I could tell that her sex would not stay there too long and it began to swell against the lace under my fingers.
Ann took her hand and rubbed my penis through the slick satin sheet and I could feel a little wet spot bloom as my teased cock spit in frustration. Ann pulled away from our kiss and threw back the sheet to see me spread naked on my back. She leaned over and took my cock into her warm mouth and began to suck me. I never knew how good a blow job could feel, but she knew how to make it better than anything I had ever experienced!
She applied suction and rolled her tongue in circles while her teeth pressed lightly at the base. She held my balls firmly and buried the shaft deep in her throat and made swallowing motions that felt divine. She held the shaft of my penis in her hand tightly and pistoned her hard sucking lips up and down on the tip.
It wasn't long before I had to warn her that if she didn't stop that, she was going to get a mouth full of protein. She stopped long enough to remind me that we had all night and that I should let loose and enjoy. She went back to that exquisite movement on my dick and in a few seconds I broke loose and filled her mouth with hot sperm. She sucked at it greedily and kept up the work until I fell back, exhausted with pleasure.
Ann came back to me and straddled me. She leaned forward and kissed me deeply. I could taste the salty residue of my own ejaculation on her lips and her tongue. We kissed and I reached behind her to unclasp her bra and free her breasts. She wagged them in my face and I pulled her down and kissed and sucked at her nipples, kneading her breasts lightly with my hands. She closed her eyes and threw her head back in pleasure.
I bucked her off to one side and drank the sight of her body in the candlelight. I moved around and peeled her panties down. She had put them on over her garter and that made it easy. Her cock was brown and flaccid, lying against her leg. I knew what I had to do; what I wanted to do. I bent down and took the rubbery member into my mouth. She was not circumcised like I was, and that was the first time I'd ever been that close to an uncircumcised prick, let alone had one in my mouth.
But I knew the things that gave me pleasure and Ann had taught me a few more, so I started to work. As I sucked and nibbled at Ann's cock it began to come to life in my mouth. I felt her balls and found her testicles had shrunk to hard tiny nuts, probably from the influence of the female hormones. I sucked and used my hand to pull down the skin against the shaft of her penis and expose the tip.
I felt Ann writhe and buck under me and could hear her moan and gasp as I did my job. She grabbed me by the hair and pulled my face down to her pelvis and I swallowed her erect member deep in my throat. I thought I would gag, but I did not. I just hungered for more and kept sucking and running my tongue around her now fully stiff cock.
Ann finally pulled away and lay on her back. "Fuck me, Rob! Fuck me like a lady!" she squealed. I had no trouble with my own tool, which was now erect and ready to do her. I pushed my dick against her puckered ass hole and it slid in easily from the combination of spit and cum that covered us. She screamed a little and put her legs in the air as I began slow strokes, in and out. I reached down and pulled her nipples. I took her cock in my hands and jacked it as I thrust at her with my prick.
Her breasts bounced in the candle light and she moaned and squealed and twisted her head from side to side. Having just been serviced like I was, I had plenty of endurance and kept going for quite some time. Finally, I came to a climax myself, pumping my load into Ann as she pushed herself against me screaming with pleasure.
When I was done, I pulled free and immediately took her rigid penis in my mouth and sucked and stroked vigorously. It wan not long before I felt Ann spasm and arch to me and my mouth was filled with hot salty juice. I swallowed it like a trooper and fell back on the bed. We both lay there breathing hard for a few minutes before we could talk. I had found what I was looking for and I loved it. So did Ann.
The rest of this story is just for Ann and me to remember. I did not go back to my hotel that night. I did not sleep much either. We explored each other all night long, in body and soul. Parting in the morning was hard, but we both knew we needed time to reflect and savor what we had experienced. Needless to say, I expect we will meet again. I did not lose her phone number this time.
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