Every time I’ve got a 100 new fans my mistress/girlfriend (Jen) has organised a dirty reward for me. There’s been gang bangs, bukkake parties and lesbian slaves and lots more. This is my first entry from when I got to 100 fans. It's a detailed account of my first night with a gorgeous ts escort. If you make really dirty comments I’ll probably respond. I especially love them from girls and other sissies. Include some references to creamy pussy, sweaty cock, bukkakes, blow bangs and generally using me like the whore I am and I’ll make sure I write back something equally filthy. I’ll try and post a new entry every few days. Hope you enjoy the account...

Here is a link to a gallery of the outfit I wore when the shemale fucked me.
http://www.imagefap.com/pictures/7042734/Outfit-I-wore-first-night-with-a-shemale-escort.?edit=1

So jumping back to the start of the year. Jen (my girlfriend/mistress) had told me to sign up to imagefap and share some of my sissy pics. A couple of weeks later and I had reached 100 fans. She told me I was a good little slut and that I deserved a reward. She asked if I’d like anything in particular. I said it’d be nice if she got me some new lingerie or shoes and we could have a fun night together. I was imagining lot’s of anal. She loves dressing me up like a whore then commanding me to first worship her ass with my tongue and then making me fuck her while she holds a wand vibrator on her clit. I love getting fucked by her too, especially when she uses her strapless dildo because I hear her getting off on it too. That Saturday she told me to pack a bag, we were going to a hotel for the night. When we arrived, she’d got us a gorgeous room with a balcony

She disappeared off into the bathroom for a while and when she came back she was dressed as a dominatrix. She was wearing a fishnet halter-neck bodystocking with a black latex waspie. Her breasts were visible through the fishnet and her pussy was completely bald and on display. I could even see a little moistness glistening on her lips. She had on a choker and a pair of black latex stockings too and some killer heels. Lastly she’d put on this dark red lipstick and a black bob cut wig. I started getting hard immediately, she looked so hot. Then I glimpsed the huge black strap on she was holding in her hand. Her red fingernails grasping it around the thick shaft. She held it up and waved it at me giggling as she did it.

She came over to where I was sitting and pressed her hairless pussy against my mouth. She smelt amazing. I love her smell, sometimes she doesn’t shower for days because she knows I love to worship her dirty pussy. I tried to lick her but she pushed me away. She told me to take off all my clothes and go stand in the bath. She spent the next half hour shaving me completely smooth. It was wonderful, I felt so feminine. Then she handed me a bag. She told me to put on what was inside. There were fishnets and a red retro bra and matching panties. At the bottom were some gorgeous new heels. I got dressed in front of her making a little show of it. When I got to the bottom of the bag I noticed another box. She made me open it. A huge butt plug was inside. I felt my asshole quiver in anticipation. She told me she wanted to watch me put it in. I lubed up my ass and slowly worked it inside. As I slid the last bit in and it filled me, I was lost in pleasure. My ass felt so wonderfully stretched and full. She looked down at me and told me I was a good whore. Then she held up a remote. She told me the plug had a vibrator in it and that she had the control. At that very moment she turned it on. Not even low to warm me up, full volume! I almost collapsed in ecstasy. My knees went weak and I started to shake. Before I knew it, she’d turned it off. I begged her for more and she told me to wait. She made me sit on a stool while she did my make up. When I saw myself in the mirror at the end I looked gorgeous. Like an old fashioned pin up. Jen made me strut around for her and told me to dance. (She’s been teaching me to dance for a while now, and I have to say my slutty moves have gotten quite good.) I acted the total whore for her, imagining I was on a stage in front of a cheering crowd. Every so often she’d turn on the vibrator. My cock was bursting out of my panties the whole time. The friction of the fishnets against me combined with the vibrator was almost too much. It got to about 8pm and she told me to stop and to crawl over to her. I obeyed, hoping she was finally going to make me eat her ass. Instead she told me to kneel in front of the bed. She put a blindfold on me and told me not to move.

A few minutes later there was a knock on the door. I assumed it must be room service but then I heard the door open, a voice, and two sets of footsteps coming closer. Surely Jen hadn’t let the room service in. I was so nervous and embarrassed at the thought of being seen like that but at the same time it made me so excited to think of a stranger seeing me there dressed like the perfect little fuck toy.

The voices went quiet and I could sense two people standing right in front of me. I guessed one must be Jen. The other, who knew…

I felt someone move behind me and then Jen’s voice whispered in my ear. “I know you love my cock but I thought you might want to try the real thing.” I couldn’t believe what I was hearing. Had she really gotten me a…. I was so nervous, I’d never even touched another cock before, only dreamt what it would be like to feel one inside me, pleasure one with my lips, feeling their cum on my tongue. Jen whispered “Are you ready?”. I gave a little nod. I heard a giggle and felt something heavy and soft and warm lay on my lips as I tilted my face upwards. I opened my lips slightly and gently kissed what was in front of me. Jen hadn’t removed the blindfold so I continued to explore with my mouth. I took the head of the cock in my mouth and then let it slip out. It wasn’t hard yet but already I had to open my lips fairly wide. It smelt amazing. The slightly hot sweaty aroma, the faint scent of cum, another smell like strawberries. I moved forward and sandwiched the cock between my face and the strangers groin. I rubbed my face the length of it, feeling the soft skin against me. I stopped when my nose reached the head. I took and deep sniff and let the smell of cock fill my nose. Then I slid my face down again till my nose reached the point when the shaft joined the balls. Again I sniffed, breathing in the musky and fruity aroma of the balls. I couldn’t resist I had to taste. I opened my mouth and held out my tongue. I felt the stranger lower their balls onto it. I moved upward engulfing them both in my warm mouth while the cock layed on my face. It’d started to grow hard now and I felt it moving by itself across my face. I kept sucking the balls. They tasted amazing. I was determined the stranger would never forget how I’d pleasured them. I reached around and grabbed their ass pulling their balls deeper into my mouth. I was surprised when I felt their bum, it was round, full and completely smooth. It felt like a woman’s ass. I could feel a thong and realised they must be wearing crotchless panties. I slid my hands down their legs and they were smooth, covered in silky stockings. I moved my hands back upwards and found two breasts enclosed in a bra. Could it be? Was my first cock, a shemale cock? I had to see. I sat back on my feet and looked upwards as I removed the blindfold. I almost came then and there. Stood in front of me was a stunning mixed race girl, a face so beautiful she could have put most real women to shame. She was clad in purple lingerie, stockings and heels and her huge cock was standing out of the crotchless panties where the pussy access would normally have been. She smiled at me. It was too much, I had to have her in mouth. Remembering all the times I’d sucked and deep throated Jen’s strap on I took her hard cock in my mouth. With my first suck she covered my slutty tongue in precum. I was in whore mode. I worshipped her gorgeous black shaft and balls like she was the only thing in the world. I could feel spit and precum running down my chin, down my chest between my fake tits and into my panties. I felt like such a whore, making a mess of myself as I sucked her big black cock. She put her hands in my hair and pulled my mouth further onto her. I took her cock so far down my throat I could lick her balls. Which I did. With every stroke, as she plunged her cock deep into my throat I lapped at her balls. I pressed forward more and more until she fell backwards onto the bed. I grabbed her thighs and pushed her feet into the air. I heard Jen gasp as I pulled off her crotchless panties and licked all the way from her asshole, over her balls and up her shaft. I held her by the thighs while I knelt in front of her and ate her ass. She tasted incredible. She stroked her cock as I plunged my tongue deep inside. I felt Jen come up behind me again, grab my head and push my face into the shemale girl’s ass. All the time Jen was saying things like “That’s it you little slut, eat her dirty ass”.

I licked and sucked and worshipped her hole for ages. As I knelt there I was grinding my ass against one of my heels, trying to push the vibrating but plug deeper into my ass. Jen must’ve of noticed because she spoke in my ear again, “I think it’s time you got fucked. She got the shemale chick to stand and made me lay on the bed. I was on my back and Jen came and knelt above me. The shemale took hold of my ankles and lifted my feet high into the air. She pulled off my panties. The air felt cold on my throbbing cock, it was covered in my own precum and drool. The shemale held onto my ankles and spread my legs. (Jen makes me do yoga and all of my dance training has left me very flexible.) I felt like a woman, my legs spread waiting to be penetrated. The shemale girl squatted and sucked my cock as she pulled the huge plug from my ass. I could feel myself gaping open. And then she did it. She stood up and slid her huge cock into my longing ass. It was perfect. Jen had moved forward so her pussy was over my face and I could literally see her pussy drooling as she watched the shemale push herself deep into my ass. Jen lowered her pussy onto my mouth. It tasted incredible, so sweaty and juicy. She hadn’t washed just as I’d requested. She used my face to pleasure her in every way possible. I moaned and sucked her delicious holes and thrust my whore ass in time to the shemale girl’s strokes. When both the shemale and me were close Jen told her to stop. Jen lifted herself up and sat on my face. Her feet stroked my cock and my tongue was buried in her ass. I heard Jen say “Fuck me Julia”. It was the first time I’d heard her use the shemale’s name. I felt Julia move up over my body and the wet sound as she entered Jen. It was like a fantasy come true. Me rimming Jen’s ass while she gave me a slippery foot job and got her pussy stretched by a great big shemale cock. After a few minutes Jen’s pussy cream began to run down her pussy and I lapped it up. After maybe ten minutes she lifted up off of my face, turned round and sat down on by big throbbing cock. Julia switched places with Jen. I sucked and licked the creamy white pussy juice that was covering Julia’s chocolate coloured cock and balls. Jen rode me like a slut. Now she was drooling pussy juice all over my cock. After a few minutes she had a huge body shaking orgasm and I blew my load deep inside her. As I was cumming I felt Julia let go and she filled my mouth with jizz. And I mean filled. Her load was huge and thick and creamy. I continued to thrust into Jen while we snowballed the cum between us.

After we laid there together, covered in cum and sweat. Jen introduced Julia properly and we laughed and giggled and played with each other. I’d always wanted to try stuffing a cock and balls into my mouth at the same time. I’d done it with one of Jen’s dildos but never with a real cock. I told Julia this and she was eager for me to try. I decided the best way was to slide Julia’s cock down my throat then try to squeeze her balls in after. I managed it, already I was getting hard again. When Jen got her phone and started to take some pictures I felt Julia start to get hard too. I took her out of my mouth and rubbed my cock against hers. Jen took hold of both of us and began rubbing out cocks together faster and faster. I asked Jen if she was planning to use the dildo she showed me earlier. I moved into doggystyle and sucked Julia’s cock while Jen fucked me. I looked over my shoulder and said to Jen in the cutest way possible. “I want Julia inside me too.” Jen moved to pull out but I held her inside me with my legs and whispered ‘I want you both inside me”. (Jen had been fucking me with her toes for almost a year by then, in fact I could fit half her foot in my ass, so I was confident I could take them both.) I got Jen to lay back on the bed and I reverse straddled her big strap on. Then Julia came and stood in front of us. I rubbed her big oozing cock between my balls, then guided her into my ass. It was almost too much. I really had to work to squeeze them both inside. Fortunately the huge vibrating butt plug and the earlier fucking had left my bumhole super supple. I took both of them inside me and moaned in pleasure. I was rock hard. As they both began to slide in and out of me Julia stroked my cock. I don’t think either me or Julia lasted more than 5 minutes. Julia squirted half her second load in my bum and the rest over my cock and balls. Watching her lick our combined cum off my cock while Jen was still buried in my ass must be one of the hottest things I’d ever seen.

When Julia left, Jen fucked me once more and I fucked her. She said my ass gaped so much it looked like a pussy. We spent the whole weekend in the hotel room. I’d brought a couple of extra outfits and enjoyed playing her sissy pet. She loves it when I dress up like a naughty kitty. The other highlights were her fucking me up against the window and out of the balcony table. Neither of us showered the whole time and giggle at how we could smell Julia’s cock and ass all over both of us. It was such an amazing weekend.

Check back soon, i'll be uploading what happened when I got to 200 fans.