When I was in college I was involved in the drama classes and theater. I was able to meet some very interesting people. There were gay couples and lesbians that filled out the classes and I found myself surrounded by a very sexually active crowd. I was dating this one young woman named Tanya that was an on stage beauty. She was 5’6 blond hair and blue eyes nice slim trim body and breasts that she never seemed to cover very well or often. In a dressing room you got to see quite a bit of your fellow actors as you threw on costumes and applied your make up and prepared for the next scene.
Tanya and I had a very fulfilling sex life; the stage was her turn on. We would practice our lines and then screw like mad resting in each others arms in our dorm room and repeat that all day. One day in our dressing room we were going through costumes from past productions and we’d laugh as we would try on everything and spin around or do some line from a play or movie. I watched her get into a tuxedo her shapely legs sliding into the slacks when I noticed how hot she was dressed as a man. She piled up her hair and put on a top hat and stood there talking in a deep voice. “Wow” I told her “if I was gay I’d date you. “ We laughed and she came over to me still in character asking me, “Would you suck my dick?” “Well if I was a girl I sure would” I answered. She smiled and turned around and found a prom dress and held it up to me seeing if it would fit. I saw what was in her eyes and smiled back. I undressed and got into the gown, and sat in the make up chair, she helped me apply eye shadow and lipstick and then finally a dark wig. In the dark I could pass for a woman. She stood in front of me and kissed me. I responded like a woman and received her kiss and I felt her hand move over my body feeling my stomach and legs her hands playing over me when I thought we were going to go farther she stopped and said, “We need to get you fully dressed if we’re going to do this right.” She grabbed my hand and we ran out the stage door of the theater towards her dorm. I was barefoot having left my clothes behind in the dressing room and my excitement and confusion made me quite excited. We got to her room drawing more than a few stares from dormmates and she closed the door and kissed me hard again. She pulled me close and grabbing my hips pulled me into her. I felt strange but remained submissive looking to see where this was going. She turned to her closet and started pulling out all sorts of things. She handed me stockings a garter belt a bra and lace panties. Pointing to the bathroom she ordered me to “Get dressed” Surprised as I was I didn’t argue and went instead into the bathroom and dressed. Getting into all of it took some time and some complaints from me but she continued to direct me through the door. I placed the gown back on and with toilet paper filled my bra and placing on the brunette wig suddenly felt very feminine.
I stepped out grandly making a deep curtsey and looking up I saw here standing there with a penciled moustache hair pulled tightly back dressed in her tuxedo shirt and slacks. She smiled and walked up to me called me her angel and how beautiful I looked. She kissed me again and then with the soft music playing we danced. I had a hard time putting my hands over her shoulder as she held my hips. I moved closer pressing tighter my head on her shoulder when I felt something poking my belly. I looked up startled and she smiled at me, “Well can’t be a guy without a cock, right.” I was surprised but my hand slid down and felt the bulge in her slacks. It was hard and firm and about seven inches long. We kissed again and she pressed the hardness into me. She grabbed my ass and ran her hands over her my tissue tits and I could tell she was truly getting turned on.
She stood back and slowly unzipped her pants and a seven inch strap on sprung out. I was shocked. I knew she had vibrators but had never seen this item before. Whispering in my ear she said. “Well suck it for me baby” I didn’t know what to do but so intrigued with this I knelt in front of her and began to slowly lick and suck the dildo. I imagined that it was her real dick and began to lick and suck on it bobbing my head back and forth she grabbed my head and began to rock her hips urging me to go deeper and sighing as I made slurping cock sucking sounds. After a few minutes of me sucking her cock she made me stand up and unzipped my gown. She slid it down revealing my bra panties and stockings. My cock was barely able to stay in the borrowed panties but she ignored it and played with my tits and belly. Her finger played around my asshole and I felt a fire ignite in me that I had never felt before. I was really getting turned on and opened my legs farther and she pushed me on the bed on my stomach. I raised my hips as she slid aside my panties and continued to lick my asshole and then without any warning slid a finger into it. Startled I nearly jumped out of my skin and staying in character I told her it was my first time. I heard her snicker when she said she’d go easy on me. Her finger moved in out of my ass relaxing it and I heard her open the top on some lube. I felt the cool smoothness drip down my ass and then a pressure as she lined the dildo up to my ass. I gripped the sheets waiting for the next sensation as she pushed the dildo slowly into my asshole now turned pussy. I inhaled deeply and arched my back as I felt her stop and then begin to go and out of me with the dildo going deeper with each stroke. I knelt on her bed in stockings and bra getting deeply fucked in my pussy. I had accepted the role eagerly. I felt her fuck me faster and faster pulling me into her I began to slam my ass deeper on to the cock, her cock filling my pussy igniting me feeling hot and excited as she fucked my pussy. I can tell she was getting turned on to the cock banged into her clit causing her to get very excited I spread my legs wider and gripped the sheets again. My cock ripping out of the panties hard raging and swollen, I was afraid I was going to cum all over her sheets as my ass pussy had what could only be described as an orgasm. My knees shook and I was ready to lose my balance when she pulled the cock out of my ass. I was thrown back on to the bed now on my back as she stripped off the strap on and jumped onto my raging cock. She was still the man even though her pussy now dripping covered my cock and we grunted and moaned as she rode my cock like a bucking horse not letting me touch her breasts but she groped my tits and then with a few hard thrusts we came together me spewing my cum deep into her hot pussy. We stopped locked in place. Frozen like this I looked up to see him and he looked down to see me in my girlie best.