My Weekend of Adventure: Sunday 24rd of July 2011

After my events for Saturday, i was just as excited to have my date with the shemale i met at the club last weekend. i have always wanted to be with a shemale, and now was my opportunity. My date did not start until around 8:30pm as my date for Sunday was busy in the afternoon with work. For tonight i wore tight jeans, my heeled black sandals with a fairly shiny purple top. i did not wear a bra, but i did wear a white and pink thong. i drove downtown and arrived in front of her/ his building by 8:30. Telling me that the restaurant is close by, we decided to leave the car in the visitor parking and walk to the restaurant. We did get to converse during our walk, and the first thing i found out that my date preferred to be called a "her". Also i found out she was a massage therapist. Being flirty i did say she should give me a massage later, which she did much agree with.
Not too deep into our conversing we did have to stop as we arrived at Milestones. Being ushered in, my date did make reservations so our wait was non-existent. We would sit at a nice table for two, in close view of the big screen TV which i did not even look at all evening. Sitting to the table, i did admire my date's beauty. She wore a gorgeous black and silver dress, with matching heels. i usually find transsexuals to dress a little overboard as females, giving them away, but my date tonight did not give me that feel. Besides the makeup being a bit heavier than my usual dates, her wear was very pretty and not way too gaudy.
We did order a pair of green apple martinis as we awaited our meals. Taking this opportunity we talked a bit more. Seems my date was 30 years old and was well off financially due to an inheritance. i told her about my work, and even of my collar to my Miss. This did lead to more questions, like relationships with my Miss, and what i expected to do with her. My response was that i hoped she would be one i could consider a "friend with benefits", but not in those exact words. To my luck, she seemed to be receptive of that idea, and we discussed some of our history, then likes. For a while we did have a long discussion of a television show we both enjoyed, that being Jersey Shore.
By the time our meals arrived, i had already drank 2 green apple martini, and even tried a blueberry martini. Not much was really said besides some banter between us through our meals. We had some jokes, and basically enjoyed our time. At the end of our meals, i did order a cosmo to go with our dessert. We decided on sharing a white chocolate cheesecake. To start our dessert, i fed her a mouthful, and in response she did the same to me. By now i was feeling really relaxed, and even more flirty as the alcohol had began to hit me. i was not drunk, but i think i was at a good fun tipsy. i did have some flirty fun with my date, as i slid one of my sandals off to stroke my foot along her calf. She did try to ignore it for a few minutes before she looked to me with a devilish smile. To end my teasing at the end of the cheesecake, i did press my foot to her crouch to feel a semi-hard cock there.
We did not stay too long after our drinks and cheesecake were finished. To my surprise my shemale date refused to let me pay, not even half the dinner. She kept insisting and eventually won out in paying for the dinner. Walking hand in hand we exited the restaurant, and made our way for a short walk around before making our way up to her apartment. Unlike yesterday, today this date and i did not get all frisky in the elevator, but stayed relatively close. Once through the door, she would turn the lights on, then dim them before welcoming me in. Sitting to the couch, she said to wait there. She turned on some slow r&b music, then place a few candles around the apartment at various areas. She then stood in front of me, unzipping her dress  and letting it drop to the ground. There stood a beautiful shemale in her black bra and underwear, her bulge being very apparent through the thin black silky material. She then said lets cut to the chase, and said why don't we go straight for what i was there for, then asking me to strip and to go with her to the bedroom.
While in there i was told to lay on my stomach. She began to massage some warming lotion to my back, rubbing it all over. She made sure to even get it to my shoulders, my lower back, butt, and thighs. After some time i turned around and felt her work her hands along every inch of my front as well. Every once in a while she would press her bulging hard cock against my bare wet pussy. After a while, and a lot of arousal i would sit up to kiss her lips. As we parted, she commented on how soft and smooth my skin was. i did not even respond, just reached over to pull her panties off. My right hand went to the base of her cock, and my lips immediately went to suck on it. i let my arousal guide me as i sucked on her cock, bobbing my head, using much pressure as i can to bring her cock to its full hardness. I did find it weird how for 6 years i have not touched one of these things, yet now in the last 2 days this is now my 3rd cock.
After suckling for a few minutes, she would grip my hair to pull me up to kiss her lips. Once the kiss separated, i would say to her that my Miss wanted me to tell her to use me like a rag doll. She said "okay" enthusiastically and pushed me to my back. Pulling my legs around her waist, she wasted no time in pushing her cock into my cunt. Feeling her full length enter me, i would moan out to the feel. Her cock was no where near as thick as the 2 i had yesterday, but regardless this one was just as wonderful. Her pacing was gradually increasing to a medium pace, then keeping it at that speed. i rolled my hips in a circular motion, meeting each of her thrusts. With the extra turn on of being taken by this shemale, my orgasm came quick. She did not even increase by that much in speed or strength but i did cum, without her doing so in return. She did not stop, but instead pulled me with her, as she laid to her back and made me squat on her. Her hands to my hips she would guide me to bounce up and down. My body had not even had time to recover from the orgasm that just passed, and now i am already in a new position working once more. My mind was in a haze, i kept moaning out for more. My body kept bouncing hard up and down, and i felt my lust growing fast and heavy. i do not know how long i lasted doing this, but i did feel myself bounce down fast as i could and as hard. i was trying to make her cum this time, but found myself cumming for a 2nd time without her blowing her load inside of me. We would slow down, and she would push me off of her to my back. Pulling my legs behind my head, she would slam her cock back into me. Her hands to my feet she would hold them there. She took me now harder and faster than she had taken me last time i was on my back. i never got to recovering from my first or second orgasm, and here i was being fucked by her cock more. i really held back hard, not wanting to cum. i kept moaning out for her to cum with me. She made me go almost insane with pleasure. i could not believe the speed in which she could fuck. i worked extra hard to hold back my spasms for what it seemed like eternity. But what i wanted to hear finally came, she said she was going to cum. i would then release and let myself go into my orgasm. As i got to my third orgasm, i would feel her bring herself to her hardest and fastest last few pumps. i screamed out for her to cum in me, in which she would comply. i felt my orgasm ripple through me all the while i felt her cum shoot inside of my canal and womb. Releasing my legs, i let them fall to the bed. She never even exited my pussy, but collapsed on top of me with a kiss.
We rested for a while, before i got up from the bed with wobbly knees. i went to her washroom to clean up the best i could so at least cum did not dribble out of me. Returning to the room i would get dressed and kiss her once more. Wishing her a good night, i said i will text her later. i made my way out, and drove home slowly, knowing very well my Miss will really want to know of my adventurous night with my new shemale friend.
Being with a shemale was always a wish i had even when i was a Domme. For one reason or another i never had gotten up to it. With my Miss' guidance i was able to make a fantasy reality. When it was all said and done, it was everything i had hoped it would be. i always had a hope it would be like being with a woman, but with the male's penis, and this adventure was very much that. i do not know if it will be like this for every shemale, but i know for this one particular one. Now i know how its like, i will not shy away from more experiences like this one.