Spring 2000, 19yrs old
I had pretty much stopped seeing Dave. I let my early feelings blind me to his true nature. I was just a slut to be used and tossed aside. I discovered he wasn’t my boyfriend, he was my Pimp!. He’d been selling my services at the adult bookstore.
Ron, the owner, suggested I might accept “gifts” from the men who fucked me.
“I’d rather see you get the money, than Dave.”
Dave? Selling me?
While I enjoyed and wanted the sucking and fucking, I didn’t want to be a whore! Dave just shrugged and said he spent the money on me. A few pizzas? Some soft drinks? A couple of outfits? What was he charging…….a dollar?
I felt dirty and cheap and told him so, but Dave just laughed. I walked out and never slept with him again.
I wondered what to do with my new found freedom. The training I received from Jackie made me more than “passable”. I lived life as a woman. Few, if any, people could tell I’m transsexual. I still wanted to suck cock and get fucked regularly, but my avenues were limited. When Fred wasn’t in town, my contacts were Jackie, her staff, and the occasional client.
I saw an ad for “Ladies’ Night” at a local Tranny bar and decided to check it out. I sat in a darkened corner of the bar and checked out the action.
Most of the trannies looked more like men in drag, than as women. They’d go onstage and strut a little and sing a song or two. The men in the audience gave catcalls and cheered them on. I felt very out of place.
“You don’t really belong here, little girl”, I heard a smooth voice behind me. “I’m Joseph, but you can call me ‘Jo’.”
I turned and saw a tall black man dressed in drag. He motioned for me to follow him to an office in back. He bade me sit and offered me a soda. My fake ID didn’t fool him one bit. (I was still 20) He looked at me appraisingly and nodded his approval.
“You look great! Not like most of the guys we see here. Are you a “Pro”?”
I nodded no.
“Then why are you here?”
“I was hoping to meet someone for an evening of…….well….you know!”
He shook his head and said, “These men would eat you up and spit you out when they were done! Most the men here are Gay and into the rough trade.”
I started to leave but he waved me back down. He went to the dressing room, leaving the door partially open to talk. He seemed surprised I wasn’t just a cross-dresser, but a true transsexual! I’d kept insisting I was a woman.
When he returned, Jo was wearing a very expensive and stylish suit. He looked nothing like I’d envisioned. He spun around and laughed.
“I only act that way in the club,” he explained. “May escort you to someplace more appropriate?”
I smiled my agreement and slipped my arm through his as we left the club. We went to a nicer neighborhood to a place called Sandie’s. He introduced me to Alex, the owner. She was a mature, stylish transsexual who looked more like a grandmother than a club owner.
Alex gave me a warm smile and said, “You’re welcome tonight, then again, when you turn 21.” (I need a better ID, or maybe I still look very young!)
The three of us sat at a table near the back, as she explained her club. It was a discreet place Trannies could meet other trannies, or men, or women. We watched a couple of singers perform and a few couples dancing to quiet music. The club was intimate and discrete.
I noticed some couples going through a door to the back. Jo smiled and offered to show me what lay behind the mysterious door. Behind the door, an attendant handed us a key with a number. Jo led me to a small boudoir with a sitting area.
“For a slight fee, Sandie’s provides a few private settings for her customers. You can entertain, enjoy each other’s physical qualities. Just no prostitution, Alex will ban you from her place.”
“Thank you for showing me around,” I said, unbuttoning my blouse.
Jo held up his hands and said, “Don’t do this to thank me: Do it because you want me!”
“I want you,” I said. I want your cock in my mouth and in my ass!”
He undressed and neatly folded his clothes, draping them across one f the chairs. I finished stripping and knelt in front of him, taking him in my mouth. He was about six inches long, medium thickness. Perfect sucking size!
I was able to take all of him in my mouth and lick his balls. I kissed the head and ran my tongue around his slit. I only used my mouth. I dragged my tongue along the bottom of his shaft, eliciting a moan from him. I held just the head in my mouth as he came, swallowing most of his cum, but letting some spill out around the corner of my mouth. I used a finger to wipe up the extra and sucked my fingers clean while looking into his eyes.
“Damn!” he exclaimed. “Maybe you should go pro! That was fantastic!”
His cock was still hard and he had me kneel face down on the bed. He kicked his fingers and worked them into my asshole. When he felt I was loose enough, he grabbed my hips and pushed his cock into my ass until he was balls deep. He pulled me back onto his cock as he fucked me with hard, fast strokes. My small breasts were bouncing with his thrusts.
It felt wonderful having a cock inside my ass again. Jo would slow down, then speed up. While I liked being fucked while on my back, being fucked this way was definitely had its good points. I’d found I liked being roughly fucked. I always wanted more cock in my ass. I guess I really am a slut at heart!
Jo fucked me for about fifteen minutes then pulled out and came all over my ass. He directed me to clean his cock with my mouth. We cleaned up and Jo hailed a cab for me.
I went back to Sandie’s regularly after I turned 21. I always had a good time and felt safe. I only used her back rooms after I met Stephanie.
Jo taught me a lot that night, but he never fucked me after that one time. His tastes ran differently, but he remained a good friend for many years.