Assignment for the 27th of August 2011

Synopsis:
Another Saturday date night with my shemale friend. This Saturday however wound up being my most tiring one i have had since the night i was tied up and anally gangbanged by an unknown number of men.

Assignment:
Waking up on Saturday, afternoon i would awaken my friend who i was with Friday night, as she stayed over after i fucked her silly with my "cock". i told her that before i went to bed, my Miss did give me an instruction. After spending the night not cumming because i did not get a message from my sleeping Miss, She allowed me to cum in a specific way. Slipping off my "cock" i handed it over to my friend and told her that my Miss wanted her to fuck me with it in both my butt and pussy and to use me until i cum myself out. She wasted no time in wearing the 8 inch strap-on dildo, with my aid in securing it behind her. She loved that she just took my "cock" as i have been calling it for the last week. i dropped to my knees on the bed, and she stood up so i could suck on the dildo as she had done last night. i bobbed my head back and forth sucking it like i would a real cock, slipping more into my mouth and throat each time until i was deep throating it. After a while she grabbed my hair and yanked me off and tossed me to my back. as i laid back, my hands went behind my knees so i could part my legs wide. Laying on top of me she slid the 8 inches inside of me. i felt electricity flow down my spine as she did, arching my back, feeling a lot of pleasure. She i could tell had experience with a strap on, she was slow to thrust, building up in unison with my body's increasing want. i rolled my hips, and rocked my body into each of the thrusts. i have to admit that this was the first time i had this particular dildo used on me, and it was very filling. It was driving me crazy with pleasure. i was already very needy and wanting to cum after spending the night pleasuring her. It felt great to have it done to myself, especially after my Miss granted it as reward for my report. Even with being taken by the my friend, the thought and images in my head were all my Miss, and the thought of Her being proud of me. i squealed and moaned, my body rocking back faster and faster to meet each thrust. It did not take long before she got me to explode into my orgasm. My body spasming and my juices pushing from my pussy, she did not stop, fucking me right into and through my orgasm. Seems she decided that i was to get everything i did to her from last night, as i did the very same thing. She kept fucking my pussy for what seemed like an hour, and i did cum 2 more times in that stretch. We moved positions every once in a while, with the dildo never sliding free from my canal, at least until the last stretch of our fucking. With the dildo coated with my juices, she pinned me flat to the bed so i laid face down on it. She slid the dildo into my butt and began working it, as my Miss did say she was to fuck all my holes. i could tell my friend was really into it as she was relentless. After sliding it in, she worked from slow thrusts to fast ones in a very quick increase. After Speeding up, each thrust started to get harder, i was near screaming, my mind was lost in a daze, and eventually i would explode into a final orgasm that put me out cold for the rest of the morning into the afternoon. When i woke a few hours later my "cock" was laying on my bed next to me with a pair of boxer shorts my friend said she would leave for me, and i was alone. My friend must have been picked up as i was unconscious from all the fucking and cumming. What a way to start my Saturday.
i began preparations for this Saturdays date around the earlier afternoon about 2:00'ish. After my shower, enemas, and eating i began to work on my clothing and makeup. First thing first was my preparations, going with my 8 inch strap on dildo, as this was the last day of my week of having a "cock". i know my Miss has been proud of the fact i have grown more and more accustomed with having it on. After cleaning it i would wear it again, then get my catheter to put on and to attach underneath the shaft of my "cock". i skipped on my vibrating ball or plug for today as i knew my holes would be busy enough shortly without the need for them. Next i slipped on my new pair of pink, red and white boxer shorts that my friend had given me. Following that i did get a pair of blue jeans, my black pushup bra and purple shiny top so i could complete my look. i once again went to dress like my Miss wished, more male on the bottom, and extra feminine on top. My makeup and hair followed suit after my dressing, giving myself a purplish eye shadow and lipstick so it would match my top, and make me look more like a slutty submissive transsexual. Last item after my makeup, i slipped my pink collar on, knowing how much it stood out from my more purplish ensemble.
My date came by to my place an hour after my preparations, picking me up so we could go have sushi together. My date tonight was with my shemale friend whom i have had a few "sessions" with the past while for my Miss. She looked gorgeous wearing a gold and black dress with black heels. i found it funny how we both had "cocks", although her's was real. She was dressed more feminine, where as i was dressed half feminine and half more manly. i think through the evening more people thought i was the tranny, and my date was the real girl, which did not bother me. The humiliation of the bulge had dissipated through the week and was replaced more with arousal. i was really feeling like an orgasm whore. Through dinner i did tell my date of what my Miss had tasked me with tonight. How i was allowed to cum, and that she wanted me to be the more dominant tonight. My shemale friend did not argue or have any problems with it. i actually think she preferred it this way. My date did tell me a whole bunch of times how she thought i looked great, and how she could not wait to feel my "cock", which made me smile and laugh. i found it weird how comfortable i am now with having a "cock" and how freely i speak of it.
After dinner we skipped doing any other activity, as i think my date's lust was very apparent. We went directly back to her place, and as we have before right out of the elevator we kissed and felt each other up. We rolled against the wall making our way to her apartment door. Once through the door and it was closed we began to remove clothes from each other, leaving a trail all the way to her room. by the time we made it to the bed, the only item of clothing we both had on were my collar, pushup bra, boxer shorts, and her thong. Her erection was pushing right out of the front of the thong. She slipped off the thong as we got next to the bed, and as soon as it came off i pushed her onto the bed and told her to lay back. i walked around her bed as i went to her drawer to pull out her handcuffs which i knew were in her nightstand. cuffing each of her wrists to opposing bed rails on her headboard, i would take the ring of keys and i teased throwing them out the window, or even flushing them down the toilet. In the end i wound up placing them on the dresser across the room from where i left her. Slipping back over i said let the games begin before slipping up to straddle her face. Squeezing my thighs i told her to pleasure me, and the faster i cum the faster i fuck her for the rest of the night. As i muffled her face, she began to lick and slurp at my pussy, pleasuring me furiously. With my right hand i began to stroke my "cock" as i have grown into a habit of doing a lot this week. i began to tell her that we were going to begin and end with my orgasms and everything in between was going to be her fucked into orgasms. i kept myself smothering her, wanting her to gasp for air, and to work faster. It did not take me long before i was on the edge of my orgasm. i resisted and held back, trying to coax my date to work more before i finally released. My juices splashing from my pussy and to her face, i began to slow my "cock" stroking.
As my body finally came down, i slid off her face and down off her body, pulling myself down between her legs. i rubbed my pussy to garner my juices onto my hand, and began to lube my "cock" with my pussy juices. Once it was shiny enough, i pulled my shemale friend's legs to my shoulders and slipped the dildo into her butt with a swift hard thrust. She moaned as i slipped it back and forth, then pushed it in deep and began to fuck her. i kept fucking her faster and slower, then harder and softer, switching sporadically for fun. When i was ready to let her cum with her cock, i pulled her legs up more and made her feel very uncomfortable, pulling her legs so her knees were on either side of her head, and her cock directly in front of her face, i used one hand and stroked her cock, and my other hand to keep balance as i fucked her relentlessly. i admit i did not take much thought of being careful as my day of sex had really driven me to want and give more. Plus she was wanting it, and kept screaming for "harder" and "more". After a while she would scream and jet out cum all over her own face, which was my goal. As she finished cumming out a huge load all over herself, i would slow down and let her legs down.
i did not let her rest at all as i began to suck off her cock to get it hard again. i know i was very lustful and i wanted her cock right that moment. i stroked it and sucked it,coaxing it to erection again before straddling her, and letting the cock slip into me with a loud "yes" from my lips. i rode her , making sure to bounce myself up and down, and stroking my "cock" while i did. i know she could not keep her eyes off of the image, and i could not stop living the image. i felt like such a slut, yet it felt so very right. She did not last as long as the time that just past, as she accidentally came inside of me without me cumming. i was a bit disappointed but i did tell her she was not done until i came as well. Slipping of her softening cock, i made her pull up a bit. Using my 2 hands, one began to stroke her cock aggressively again. My other hand began toying 2 fingers to her butt, then 3, and eventually 4. i was thinking of fisting her but i thought then i may make her cum again so i did not pass 4 fingers. i could tell that this maybe the last time tonight i could get her hard and to cum, so i worked furiously until it was rock hard. Slipping my hands away i straddled her again and resumed riding her, and stroking my cock. i know after cumming twice this time was going to be that much harder for her to cum. i rode her for 30 minutes, trying not to ride to quickly. As i felt myself approach my orgasm, i did tell her and i held back waiting for her to say that she was going to cum. When she did i released into my orgasm, letting my body push past the edge of my climax as i felt the euphoric serenity and peak of pleasure hit. i did feel her shoot the smallest of her 3 loads into me, making me smile as i have really grown to love feeling cum shoot inside of me.
i rested up a bit before getting re-dressed and ready to leave. My date was completely out cold, showing her male side of cumming and passing out which made me smile. i took a cab home, which i am sure the cab driver thought i was some slutty transsexual hooker going home after performing a trick. i smelled of sex, and i looked like a prostitute with a huge bulge. Once home i was lucky to catch my Mistress who made sure to end my day off with a huge smile. She made me take in 2.5 liters of mixed wine and water mixture which made me extremely drunk. While being drunk she made me stroke my cock with and fuck myself with a vibrator until i came. i was pretty hazy at this point and i did not remember much detail besides wishing my Miss good night, then passing out until late afternoon when i woke to write this. i am still tired out of my mind, yet i feel so loved by my Miss coming into our 2nd month's anniversary.