It began as just another night at the local bar. Being very shy and introverted as I was, I sat at the bar near the end by myself as usual. I came here knowing that it was occasionally frequented by gay men. It was impossible for me to meet women and I had hoped that I might be picked up by one of the men so that I might experience sex with someone.
While sipping my second glass of wine, the bartender came up to me with another glass of wine and told me it was compliments of the gentleman in the corner booth. He hoped I would join him. Being extremely nervous I almost said no, but changed my mind.

I walked over to him and he asked me to sit. I am so sure he could see how nervous I was and he smiled at me. He said his name was Joe and I could see that he was very handsome. The classic tall, dark and good looking older gentleman that most dream of. His manner was very disarming and we were soon chatting about many things as he continued to keep my wine glass filled. Perhaps I was getting a little tipsy when his questions became a little more personal. I found myself answering with ease. The question that caught me off guard was when he sled if I had ever dressed as a female. I am sure I blushed thinking he had found me out. He put his hand on my leg as I sheepishly answered that I had, in private. I told him that right now I had on some frilly panties, a garter and stockings and always kept myself smooth because it felt so sensuous. That was all I had to say before he asked me if I would join him in his apartment for a nightcap.

He offered to drive and since I had taken a taxi here I told him sure, why not. We walked out to his Lincoln and he even opened the door for me. It was a short ride uptown to a very posh apartment building. He parked in the garage and we rode the elevator to the penthouse. I was so impressed and as I turned to him to tell him so he bent down and covered my mouth with his, kissing me deeply. It felt so wonderful my knees almost buckled and his strong arms held me up. He walked me over to the first bedroom and told me that perhaps I could change into something more comfortable. I didn’t know what to say so he told me to go on in, choose something I might like and model it for him. He left to get a bottle of wine.

I walked into the bedroom, opened the closet and could not believe my eyes. In the walk-in closet was the most extensive female wardrobe I had ever seen. It was so exciting I had to try something on and found a flirty short black cocktail dress. Opening one of the drawers was a selection of bras and all had the nipple areas open. I quickly stripped off my shoes, pants and shirt. Putting of the bra I found that it really made my nipples stand out and it looked like I had pert little breasts. I then slipped into the dress and looked for a pair of shoes. i picked a pair of black baby Janes, and was amazed that everything here fit me perfectly. I went out and found a dressing table with makeup, wigs and perfume. Sitting down, I chose a brown medium length wig, and placed it on carefully. I could not believe how good it looked. A little eyeshadow, lipstick and a quick spritz of perfume on my wrists and I walked out of the room to see what Joe thought.

His mouth dropped open when he saw me. “I knew you would make a very pretty girl, but my gawd, you are beautiful”, he said, “Please come over here at sit by me.” I walked over and sat next to him on the loveseat, taking the glass of wine he offered. He had made himself comfortable as well, now wearing nothing but a robe tied in front. I too a sip of the wine and set the glass down. He put is arm around me, drew me close and again leaned over to kiss me deeply. His tongue darting between my lips made me so hot that I reached down, put my hand under his robe and felt the most magnificent cock. Pulling it out I looked down and could not take my eyes off of it. It was at least 7 or 8 inches, perfectly curved, with a beautiful smooth bulbous head. “I have never done this before”, I said, “but please, may I kiss it?” Smiling he said ”My dear, you can do whatever you like.”

I untied his robe, leaned over and lightly kissed the head, opening my mouth I licked it and swirled my tongue around the head. Opening my mouth a little more I carefully took the hue head into my mouth and took a little of the shaft in. Pulling my head back a a little I slid my mouth up and then back down a little further. I could tell he was enjoying this by his soft moans and I wanted to make him cum. I took as much as I could into my mouth each time until I felt it hit my throat. I had read that if I relaxed my throat I might be able to take it all so I kept pushing until I could feel his balls on my chin. My gawd, I had done it and he was loving it. I felt him gently pull me up and he kissed me hard again. ‘Are you sure you have never down this before?”, he asked. “ I have read bout how to do it, but it really is my first time”, I said.

With that, he pushed me back onto the loveseat, kissing me harder and deeper. His hands began stroking my legs, up my thighs and gently caressing me between my legs. Pushing my panties aside I felt his finger gently pressing on my hole. Gasping between his kisses, i know he could tell he was really turning me on. He pulled down the top of my dress and his tongue began filching my now rock hard nipples. I could not contain myself and began moaning and calling his name. “I am going to call you Kim”, he said, “and I want to take you all the way”.

He picked me up like I was a doll, carried me into his bedroom and put me down on his bed. Climbing on top of me, he removed his robe and pushed me back onto the bed, smothering me with kisses, playing with my nipples and pulling my dress up to my wait. His kisses became more fervent as he pulled my panties off, moved between my legs and began kissing my tummy, my little cock, down to the insides of my thighs before lifting me up and placing a couple of pillows user my hips. The next thing I knew his tongue was licking my crack and burrowing its way into my tight little hoe. “Mmmmm, you are so tight my dear Kimmie”, he said, ‘but I think you will love having my aching, curving cock buried inside you”. ‘I have never down this before, Joe”, I said, “I am afraid it will hurt!”. With that I felt his finger enter me. It hurt a little but he told me to relax. He put something on his fingers then I felt two then three stretching me. It really felt good and I think he could feel my response to his invasion.

He moved back up on me, kissing me then putting my legs on his shoulder, I could feel the large smooth head of his cock at my entrance. He was pushing and as he entered me I gritted my teeth in pain for a second. He stopped so I could get used to being stretched then slowly pushed all the way, When I felt his balls against my ass I knew he was al the way in and I had never felt so full, so stretched. Soon the pain was replaced by the beginnings of a unique pleasure. Slowly he began pulling out and pushing back in. Fucking me slowly as I began moving my hips, trying to meet each thrust. He let my legs down so I could wrap them around him and I was soon pulling him into me moaning with pleasure. I had never felt anything like this before. “My sweet virgin”, he muttered, “I am so glad I was the one to take your cherry. You are so tight and feel so good, Kimmie”. I could not really answer him, breathing hard, moaning with the pleasure he was giving me. Suddenly he picked up his pace, slamming into me. I could feel his cock swell even more and I was so close to cumming. He slammed into me one more time, his cock twitching and suddenly I could feel him pumping his hot load deep into me. I could hold it no longer and could feel myself cumming onto my own belly. My little cock trapped between us. It began as the most intense orgasm I had ever felt and every twitch of his cock just intensified the feeling even more. It was minutes before I started coming down from this and I kept my legs and arms wrapped around him. I wanted him to stay inside me but could feel him softening. He kissed me hard and as he pulled out I pouted. he said, “you are the best fuck I have ever had. Please stay the weekend with me. There is so much more pleasure in store for both of us”. How could I refuse? He had taken my virginity. “I am yours to do with as you please”, I said. “I have never been with a man before and you have shown me so much tonight, I can’t wit to see what else you have in mind”.

story by: jen128

Tags: blowjob consensual sex first time fantasy anal transvestite gay transsexual transgendered sex story

Author: jen128

Related sex stories: