Beginnings: My First time as a crossdresser (PT 1) - Sex Stories

Beginnings: My First time as a crossdresser (PT 1)

... Mikki was bisexual and a bit of a self confessed slut, so I had no illusions about her faithfulness. But hell, I was 17 and NOT about to look a gift horse in the mouth. Sex with her was great and I was willing to put up with a lot to keep that going. “Well then that’s your primary identity and how you feel dressed as a girl is like an alternate personality” he explained. Which was all well and good but I was realizing that I was currently dressed as a hot slutty girl, and getting more aroused by the moment. Also that there was an attractive man sitting in front of me with nothing but a silk robe on. One who I knew wanted me and that only made things worse! “Ok, I think I get it but it’s getting really late and I want to feel you inside me” Smiling, he took the glass from my hand and pulled me to him. He turned me around and took the blanket from my shoulders and then helped me out of my cropped leather biker jacket. He started to massage my neck and shoulders, kissing my neck gently as he did so. His touch was like heaven. He knew all of the right spots to hit and his tongue on my neck was doing very naughty things to my brains pleasure centers. He continued to massage my back shoulders and neck, making me melt with desire. I turned on his lap straddling him and started to kiss him. He responded in kind and I felt his tongue darting in my mouth like an asp, gentle and delicate. His hands rubbed over my body, cupping my ass, feeling my legs and thighs. I got a special thrill ...

... when he ran his hands over my ersatz titties as they were feeling especially sensitive. I kissed my way down his neck and chest, opening his robe as I did so. Working my way down to his cock, I had an insatiable need to feel it between my lips. I was gratified to see that he wasn’t as large as Derek or Jon my best friend. I was determined to feel him inside me but was a bit worried about how I would handle it. I had played with some makeshift toys before( a handle from a large screwdriver, a small vibrator I stole from my s****r, the handle of a brush, etc.) but had never had a cock in me before and was unsure how I’d handle a real cock. He was about 6 ½ inches long and thick but not too thick. I started to make love to his dick with my mouth, attempting to emulate the porn stars I’d watched on vhs ,when I would babysit for our neighbors, after the k**s were asl**p. They had a nice collection and my favorite at the time was a star named Ginger Lynn. He was gentle and totally different from Derek and I loved it. I swirled my tongue around the head of his dick and licked up and down his shaft with my lips caressing his balls. Soon he was moaning in pleasure and lifted my head up from his lap. He looked into my eyes for a moment and then kissed me deeply. I knew he was ready to fuck me so I fumbled on the coffee table for Kayla’s purse and the condom’s in it. Pulling one out I tore the wrapper open with my teeth and slipped the condom in my mouth so I could apply it over his dick ...