Tag Archive for 'Cross dressing fetish'

Cross-Dressing Fun

My doorbell rang. My boyfriend was supposed to be picking me up, so who was this statuesque blonde on my doorstep? She was dressed in a tight little black dress, stockings and stilettos. Quite beautiful. “Hello, Toby,” she said. OMG, it was my boyfriend, dressed in drag!
I stepped into him and gave him a big kiss, wrapping my arms around his neck. “You look so hot, babe!”
I ran my hands over his body, across his ass, around his hips to his cock, which was getting hard under his dress.
“Come in. We don’t want the neighbors seeing what’s going to happen next,” I said, pulling him inside.
I was wearing a little red dress, and he pushed it up over my hips and pulled my panties down. He got down to his knees and started kissing and licking my tummy, my thighs, my sex. He picked my left leg up and slid it over his shoulder, dug his fingers into my ass and pulled my pussy into his mouth. He pulled the hood on my clit back and sucked. My legs started shaking as my orgasm started to build, and then I was cumming in his mouth. I dropped to my knees and kissed him, tasting myself on his tongue. My hand went to his cock again… he was harder than I’d ever felt him. I pulled his dress up over his head. He was wearing a black bra and matching panties and had a black garter holding his stockings up. I took his big cock into my mouth and sucked as I slid my hands over his body, under his bra, pinching his nipples.
He pushed me off his dick, stood up and pulled me to my feet. Bending me over the couch, he slammed his cock into my wet pussy and began fucking me. Every thrust was harder than the last and I started cumming again. He pulled his cock out of my pussy and then I felt his fingers…. he began lubing up my tight little ass hole with my cum, and then he pushed his cock into my rosebud. His fingers went to my clit rubbing little circles as he worked his way into my tight little hole. Pumping his hard cock in and out of my ass and playing with my pussy, I felt my climax building yet again.
“I’m going to cum again for you, babe… cum with me…” I moaned as we exploded together.

My Submissive Sissy

Finding you standing in my bedroom all dressed up in my panties and my nightie, and some of my jewelry. I could even smell some of my expensive perfume on you. You’re dressed just like me. I watched you from the door way as you admired yourself in the mirror. Prancing around, practicing to walk like a woman. Your erection was a little hard to hide. I do have to say, I was a little surprised but I knew exactly what I was going to do with you from this point on. I walked into my bedroom wrapping my hands around your waist, whispering inĀ  your ear “what a naughty boy you’ve been.” I’m thinking you need to be punished now. Making you crawl up onto my bed laying face down spreading your legs. Making you wait with anticipation as I pulled out my strap-on. Making you feel so helpless as I pushed up your silk nightie and ripped off your panties. Rubbing my strap-on along your tight aching hole. Watching you squirm all over my bed with pleasure as I started to have my way with you. Stretching that little fuck hole wide open. Teaching you a lesson not to go through my girlie stuff with out asking me first. I’ll be the one dressing you up and fucking you like my whore.

Charlie

My Favorite Toy

It never requires batteries and I can use it anyway, anytime I want to. My sexy submissive boyfriend is my favorite toy to play with. He is always eager to please his Mistress and never hesitates when it comes to obeying me. “Yes Mam” he says in his weak, sub voice while he lowers his head being careful not to look up without permission. He surprised me wearing a sexy black bra and hot black thong early this morning ready to be owned and controlled. I never knew a panty boy could look so good and of course, I had to get my share. Bending him over I spanked his cute ass several times pulling his thong tight between his naughty crack. I knew his man pussy was mine when I heard him beg for my cock just like he always does. I told him to lay back on my bed and then slowly I climbed up and straddled his face. Humping, pumping and grinding my tool into his mouth until it was all wet for his hot hole. I asked him again “what is it that you want bitch boy?” But I already knew what he wanted so I probed his asshole with long, slow strokes and started to fuck him. His sexy bra slid off his shoulders and I turned him over on his stomach, doggy style, to finish him off. Such a hot panty boy still wearing his slutty thong taking my tool hard and fast just like a good bitch. When he finally begged to cum I allowed him to do so and watched as he creamed his sexy panties.

My favorite toy by far and the most fun indeed. So many ways to play with him and so little time.

Kisses,

Miss Annaliese