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.
Tag Archive for 'cross dressing men'
Mommy has caught you once again sneaking into my room going through my hamper picking out my dirty panties. Shame on you! What do you think, I should do with you now? The possibilities are just truly limitless! I can turn you into Mommy’s sissy boy and make you wear my dirty panties all day long or better yet I can stuff them right in your little mouth and make you clean them like a good boy. You will take whatever punishment that I give you. I understand you are so mesmerized with all of Mommy’s undergarments. I don’t mind you playing in my closet at all but I find it more of a turn on when I dress you up so you can look just like Mommy. Isn’t that what you’ve always wanted sweetie? No need to answer, just call me so we can play dress up and put a pretty little smile on your face.
He has always been this way for as long as he can remember. “Jade when I look at women I look only to see what they are wearing, what kind of manicure, hairstyle and make-up. It’s been this way my entire life. I never look for sexual reasons only to admire and to learn how to be a woman.” My heart went out to him instantly as I heard the sincerity in his voice this isn’t ‘t a fantasy or some sort of role play but very much his reality. Eager to hear more I began to gently probe while giving him my undivided attention. We discussed my experience growing up with a cross dressing brother and the hardships that come along with being “unique.” Society isn’t kind to those who step outside the box of what is considered the “norm” and though I think it’s a different world today than years ago we still have a long way to go. I listened as he told me his desires to be a woman and how he feels his very best,complete even when he able to do so. Manicures, lingerie, make up and pretty clothes, sparkling jewelry these are the things he enjoys in the privacy of his home. Behind close doors he indulges in what makes him most happy being his true self a sensual, sexy woman. As our conversation continued I learned of his relationship with “B” a gorgeous T-girl (tranny) that loves and accepts him just the way he is. The two share a very open and beautiful thing it was very moving for him to share such intimate details. I thanked him profusely and just then the thought occurred to me. Why not “come out” on Valentines eve and share his special moment with his beautiful “B”. I can’t think of a better time so I decided to play cupid and shoot my arrow. My aim must have been good because the next day I recieved an email with a picture attached of the dress he and his lover picked out for him to wear a very special night for two. Again,moved,I instantly replied elated for them both. I sincerely wish you only the best my beautiful “Jessica” and I know that you and your lover are going to have a most memorable and erotic evening. Please do not doubt yourself be proud of who you are and revel in the moment of finally “coming out”. I hope you feel like a movie star this night because I know in my heart of hearts you will certainly look like one. Do not be afraid to be who you truly are inside no matter what anyone says you are beautiful to me, always. Thank you for sharing with me I look so forward to hearing all about your grand evening and wish you many,many more to come.
Much love and harmony,
Jade
My little sister and I have always been very competitive. When it comes to men it’s really no different. If we see something that we want even if we both really, really want it I TAKE IT.
Like her new hubbie for example. What a hot fucking stud he is and the temptation is just well more than I can continue to stand. I feel it’s only fair I give him a sample of big sister and well he got a sample alright.
Knowing my lil sis was well on her way to work I decided to drop by the homestead and pay a little visit to brother dear.
Seducing him was easy almost to easy he was all to eager to fuck his wife’s older sister. What surprised me the most was how damn kinky he was.
He told me how he secretly loves wearing my sister’s lingerie and has always wanted to suck cock. Wow! I jumped all over this needless to say.
We spent the day fucking, sucking, dressing up and well much more than I can write here.
I’m in the mood for more kinky fun wanna join me?
