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Sugar Daddy's Sissy

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Sugar Daddy’s Sissy
I rolled over in bed and his cum oozed out of my ass; my 53 year old lover Cliff had really fucked my ass last night. You see I am a 23 year old, 5 foot 5 inches tall”, 110 pound skinny twink with a thin girly body. Cliff, my lover, is a prominent attorney in town and I am kind of his “kept mistress”. But who cares, I got a brand new Ford Mustang in the driveway paid for by Cliff’s law firm. Plus the sex is pretty good.

Cliff’s greatest pleasure comes on Tuesday night when I dress up as a young women and frequent a private club for gay men in town. He beams with pride when he enters the club with this hot young women (me) and everyone knows he is fucking me on a regular basis. Usually our Tuesday starts when Kate my make-up artist arriving at about five, tonight she brought a red cut out smock dress with a silk bottom which was highlighted by a red bra and panties and a pair of thigh high nylons. She worked on my face for about a half an hour and I looked like the cutest thing. This was topped off with a red collar which indicated to everyone at the club that I was Cliff’s women.

Cliff came and picked me up and off we went to the club. Cliff was escorting the youngest and best looking sissy in the place and I got quite a few admiring looks. None of the three or four other sissies present came close to how hot I looked. Cliff sat down with some friends and called me Allison when I was dressed as a women he always referred to me as Allison not my male name of Allen. During dinner Cliff’s hand went up my leg and he began fondling my cock under the table. I knew that soon I would be heading to the back room to service my man.

As I expected right after dinner Cliff took me to the “special” back room in the club with couches and private areas. It was here that these distinguished older rich homosexuals had sex with each other, their young male lovers and for the lucky few their young sissy’s. I fell into the latter category and soon Cliff and I were in a private booth in the corner.

Cliff immediately began kissing and fondling me all over, our tongues intertwined again and again as I felt Cliff’s cock getting rock hard. A dim light lit the room so I could see as I got on my knees unzipped Cliff’s pants and began sucking his lovely seven inch cock. As always I began by vigorously sucking the head of his cock, concentrating on just the head. Then I worked my way down the shaft sucking harder and harder, taking Cliff just to the edge of and orgasm. Then I drew back before sliding all of his seven inches into my throat. Then I sucked his cock good and hard as I held it firmly in place in my throat.

Then Cliff said “stand up I want to see your smeared lipstick”. I obliged this kinky past time as I stood up as he fondled me from head to toe concentrating on my nylon clad legs, lifting my skirt up and grabbing my full breasts. Several onlookers stopped what they were doing to admire my young feminine body. Soon I returned to my knees and I began rapidly fluttering my tongue back and forth around Cliff’s penis until it reached the head. Then I would swallow his cock again all the way down my throat where I resumed my hard sucking of his entire cock. I knew Cliff would not be able to take this for more than a few minutes and soon he yelled “Allison I am coming right now!!!” With that I deep throated his cock and held it there while he shot a large load deep down my throat. It tasted like alcohol since Cliff had been drinking at lunch and dinner. I tried to swallow most of it but his cum dribbled down the sides of my mouth.

Then I performed my specialty, after swallowing his load I just kept sucking his cock. As in the past I knew the sensations of my sucking his highly sensitized cockhead were incredible. Cliff moaned which everyone could hear and several looked as my head bobbed up and down on his cock. I worked even harder by sucking and swirling my tongue around the area where his head met the shaft. I sucked his male “G” spot and licked the head area of his cock. Finally Cliff said “Stop! Stop! You’re killing my cock”. I stopped and just looked up at him and grinned as his excess sperm dripped down the corner of my mouth. I scoped the cum off my face and licked it off my fingers. We lay back on the couch and finished our drinks as I caught my breath. I knew I would be bedding down Cliff that night and his cock would be in me several more times that night. I really wanted to be fucked with that dress on.

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