I suppose you might call me a frustrated thespian, because I love to role play. That’s Thespian, not Lesbian, although I freely admit there have been times I’ve indulged my Sapphic nature as well. In fact I believe the concept of Role Play fits the androgynous model like a hand in a glove but today’s topic of discussion is role play with a member of the opposite gender so try to focus.
Scheduled role play sessions are extra fun for me. After all, in most of my regular sessions I pretend to be the client’s girlfriend anyhow. Most times a client wants me to play the part of a young coed while he plays the part of an older Sugar Daddy. This interaction doesn’t necessarily require a costume. Oh sure, sometimes the guy wants me to put my hair up in pigtails and wear a white, cotton blouse and a plaid skirt, maybe a pink ribbon in my hair and bobby socks, but he really doesn’t have to dress up at all. The stock costume for a pretend Sugar Daddy is the same as street clothes for a normal guy. The main difference is, when a dude pretends to be my Sugar Daddy, he doesn’t have to pony up the rent every month.
Tony’s request was different. He called and asked if it would be okay for me to play the role of a mistress who had been caught cheating on him. He gave me a laundry list of clothes to wear. He also asked me to have some pictures in my purse showing me and another guy banging away on a ratty bed in a sleazy hotel room with the shades down. What the fuck! I can say it wasn’t much of a stretch for me to get into the role and God knows I had plenty of raunchy pictures but I couldn’t for the life of me figure out what Tony’s game was. He was a favorite client of mine and he’d always been pretty meat and potatoes when it came to doing the bad nasty. In fact I can’t recall any position with Tony besides missionary, even though I’d hinted broadly that other options were on the table.
I dressed up in the light blue, cashmere sweater and tight jeans (no panties!) Tony asked me to wear and sat on the edge of the bed to await my deceived lover. As an aside Tony is an attorney in a prestigious law firm downtown and it wouldn’t do his reputation much good to have his secrets spread around. Listen, his secrets are safe with me. My lips are sealed.
Right on time, Tony knocked on the door and stormed into the room, demanding to see inside my purse. I reluctantly took out the pictures and showed them to Tony. He was livid. He grabbed me by the ass, unbuckled my belt and tugged off my tight jeans. Then he ripped off my sweater and bra. I cowered naked at the edge of the bed while Tony threw off his own clothes. I was amazed to see how stiff his cock was! He turned me over the bed and began to spank my ass. The torn clothes were part of our deal but the ass-spanking was starting to hurt. Still, there was a subtle thrill that went with the pain and I was starting to get into the submissive role pretty good.
Tony ran his fingers between my ass checks and over my tight little butt hole. My exposed pussy was clinching hard and I could feel my wetness growing. He stroked it with his finger, circling, rubbing it, and spanking me hard with his other hand. I turned my face up to Tony and suddenly his cock was in my mouth. He rammed a finger up my ass and I heard the angels sing. Holy fuck! I was coming and gagging and he was coming and roaring and then we both collapsed in a heap of laughter and tears.
Tony still drops by from time to time but we’ve never tried to repeat that particular scenario. Sometimes a play works best when you don’t know how it’s gonna end. Ciao!