2/17/2017

"Porn Stories" My first time with a Shemale

Porn Stories My first time with a Shemale
By the time I turned 18, I had already done a lot of fucking - mostly with women in their 30's and 40's. As a k**, I was kind of a stud, mowing lawns in the neighborhood. I had a bod, and went shirtless, in shorts and sneakers, for effect. The women in the neighborhood did love me and tipped me well after mowing their lawns and eating their "bush."(Erotic Stories)

I did finally land a job as a pool boy at the Fountainbleau Hotel. The sexual encounters remained the same but in much better surroundings, and the tips got a lot better.

On one beautiful day, I spotted this gorgeous red head, Arlene, in maybe her early forties, kinda giving me the eye. She was kinda thick, with great tits, a hot round ass and thick legs. We exchanged glances for maybe fifteen minutes. then she motioned me over. I was speechless. I couldn't stop checking her out and the bulge rising in my shorts became obvious. I stammered something like "how can I help you," and that started an interesting conversation, ending up with me agreeing to meet her, at her room a shifts end. The fact that I was not dressed to be running around the hotel was not a hurdle. When I did get there, she was dressed in Hot Pants and a halter top. Her hair was in a pony tail and she looked HOTI

Arlene greeted me with a glass of white wine and took me to the terrace overlooking the ocean. The conversation was short, lasting as long as our first cigarette. She spoke and I stammered. She began caressing my arm, my shoulder and my neck, then pulled me to her and gave me a long, and very deep french kiss. My hard on that I had since I got in the hallway began to ache. I pulled her to me and enjoyed one of the most memorable passionate kisses of my young life.

Inside the room, it was off with my shirt and her halter top. I got her shorts unbuttoned but she stopped me, told me to slow it down and pointed out that we had all night. It was hard backing off but she got me to the couch and offered me more wine. A brief conversation ensued, then she went to the bedroom, came backed dressed in a hotel robe. She brought a joint with her and asked if I smoked. I was confused since we both had cigarettes on the terrace. She explained. It was to be my first "smoke," but at that moment in time, I was ready to do anything if she would just let me fuck her!!!

We smoked that joint and had some more wine. I had the giggles, an aching hard on and finally it was back to passionate kissing. I got the robe open and held those gorgeous tits but I could not get way from kissing her. Then it started. She began to use her tongue on my chest, working downward. She got my shorts unbuttoned knelled in front of me and took my rock hard dick in her mouth. I thought I was going to cum immediately but she stopped me by coming back up to the couch. Again she pushed me away gently but kept rubbing my thigh. She then asked me to massage her feet (a first for me). That led to Arlene putting her toes in my mouth which I accepted willingly. She went wild with passion opened her robe fully, tore off her blue panties, spread her legs and released one gorgeous COCK!!! This was a SHOCKER, but it not slow me down. I worked my way up her legs with my tongue to her swollen balls, then took her erect cock in my mouth while caressing her swollen sack with my fingertips. I had never tasted cum before but again she stopped me, got to her feet and d**g me to the bedroom, leaving me with only the taste of her precum. She pushed me on the bed and we were in the 69 position with me on top pulling her legs apart and taking nearly all of her in my mouth. I came in Arlene's mouth within seconds, but she held out a little longer bucking, her legs wrapped around my head trying to get me to accept all her cock. Arlene began to shake and cry out as she exploded her sweet juice in my mouth.

Afterward, there was this beautiful afterglow where we lay in bed, gently kissing, fondling and caressing and took time for a couple more hits on the joint.. About a half hour went by, the kissing and caressing became more intense. Arlene straddled my shoulders and slipped her cock in my willing mouth once more, gently rocking back and forth, her hand playing with my cock. Then, things got weird. Arlene took my head in both of her hands. Rocking back and forth with her full weight on my chest she took my head with both hands and began pumping my mouth. I was feeling very uneasy, but very excited as it felt like her cock was bouncing off my tonsils, making me gag. Then, she jumped off of me. stood on the floor, gave me a wicked french kiss, then reached in the bedside drawer and pulled out a tube of KY jelly. Again, Arlene began to slowly suck my cock and this time, she was caressing my ass hole with her fingers then, one finger was massaging my prostate, then two fingers as I grew to the point I was going to cum all over both of us. I watched with fascination as Arlene caressed her beautiful cock with the KY, stroking it as she stood over me, caressing her she cock. She got in the bed, between my legs and lifted them to her shoulders raising my ass off the bed. I felt the head of her cock gently pushing at my hole. I was nervous and excited, keeping my eyes locked with hers.

Arlene pushed. I felt a serious discomfort then pain as she slid herself further in to my ass - gently, then all the way. Back and forth, easing in and out, smiling and stroking, her beautiful tits bouncing up and down. For the first time, I felt this beautiful woman and I were suspended in time and pleasure. Arlene began to pump me, as I had pumped women before her and it felt wonderful. Finally, I felt her hot load inside me and I exploded all over both of us as she collapsed on my chest.

We were to spend three more days and nights together and this story could repeat itself over and over. Arlene and I got together a number of times over the years, even after I was married - twice. Miami, New York, Chicago, Los Angeles, Ocho Rios and St. Marrten.
I lost track of her 20 years ago and still search for her on Hamster, facebook and flickr.


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