True Story, Anal, Ass to mouth, Ass to pussy, BDSM, Bi-sexual, Blackmail, Blowjob, Cum Swallowing, Domination/submission, Female Domination, Foot or shoe fetish, Gay, Humiliation, Pegging, Prostitution, Transsexual
Tom began to quicken his pace, it felt like he was going to drive me through the stockade. I clenched my fists and toes and bit my upper lip to cope with the pain, but I could feel him tensing up to finish. He told me to clench my asshole around his cock and as I did he shot off a warm load into my ass as he pulled out. He wiped the remaining cum onto my ass cheeks before taking me out of the stockade. "Damn you were a good slut, I knew there would be some reason that it was good to keep you around work," I was to raw from the fucking and couldn't get up for myself so Tom dragged me to the center of the room where he tied my hands together Tom and over my head. Dangling from the ceiling my manicured toes could just barely scrape the ground. Tom left me and I waited alone for hours, I could see from the skylight that it was just beginning to get dark when Arif finally came through the door.
I scolded Arif for everything I had gone through, the bondage, the rough fucking, and degradation but it didn't last long. Arif slapped me across the face and grabbed my throat and said to me "Tom was thrilled so I've decided I'll be whoring you out regularly so you better learn to live with it and love it," I thought about the slippery slope the last few days had been "Now since you won't still be tight for tight for to much longer lets have one last hurrah before you'll mostly be for clients." Arif untied me and led me to the bed, I undressed him and took out his cock and wetted it with my mouth before he layed me on my back. He gingerly pushed his throbbing cock through my rim as I rested my legs on his shoulders. He fucked me thoughtfully and gently and I enjoyed the change of pace from the brutal fuckings I was used to. As Arif worked deep to my prostate I got hard and slowly began jerking my cock. We continued for a while and were both just about ready cum, so Arif quickened his pace just slightly and I grabbed onto the back of his neck. I came first without even needing to continue stroking myself, and blew my load onto my stomach and Arif followed suite pulling out and adding to the pile of jizz.
We both sat there breathing heavily for a while before Arif got up and dressed and told me to show up at Leahs house early the next morning. When I got home that night I thought to myself how I had only planned to meet a guy online and try some things before the whole e-mail fiasco but return to hetero sex but I had found myself getting off to being someones bitch. I tried jacking off to straight porn but it wouldn't work all I could only picture myself as the girl and got horny to the idea of real or rubber cocks in me. Eventually I gave up and went to bed; when I woke up the next day I plugged Leah's address into my GPS and got there around 10:00. It was a hot summer day and Leah greeted me at the door still in cute pajamas and brought me out of the sun into the cool a/c of her house. She told me Arif had a beached day planned so we had some work to do so it was good her parents weren't home. As we went upstairs to her room I was a bit worried, up to this point everything we had done was behind closed doors.
First in the bathroom Leah had me undress and she again shaved and douched me then did both our makeup and hair. We got out of the attached bathroom back to her room and she quickly slid off her clothes and I admired her backside as she went through her closet and drawers for our outfits. My outfit started with a black bikini bottom and a pink strapless bikini top. Leah wore a revealing teal bikini set. We both put on tight denim shorts that showed off our legs and I wore a tied up plaid shirt revealing my stomach and she wore a loose fitting t shirt that fell of her shoulders. Completing my attire was oversized sunglasses and sandles. After a quick look in the mirror Leah said "If I was a guy I'd fuck you," and she'd have good taste because I looked like a sexy beach bunny. Leah grabbed a tote bag and we headed to the beach.
Arriving at the beach although I was nearly unrecognizable I was still nervous being in drag in public. Leah and I found a spot in the sand and spread out our towels, I reluctantly followed her lead and took off my shirt and shorts. Despite a fake bust through the padded bikini and my package concealed fairly well I quickly layed down on my stomach. I felt Leah straddle me and she began applying sun tan lotion to my backside, as she worked towards my lower back and upper legs I noticed that all the men in our area were trying to catch a glimpse of her rubbing me down with the oil. I had been in there situation before, infatuated by two hot chicks on the beach. As Leah finished Arif showed up and greeted us. After rubbing Leah with the lotion we layed out to get some sun for about 3 hours. I had fallen asleep but Arif woke me up and explained how we were going to walk down the beach to a clients boat
Walking along the water I noticed I had tanned very well but gotten a bit pink. I also noticed how jelous other young guys at the beach were of Arif who appeared to be with two attractive girls. When we got to the port the boat we approached was huge and two men both medium builds probably mid forties were on deck with drinks in hand, these guys smelled like money. Arif told Leah and I to lay out in the sun a bit longer on the front of the boat while we started sailing and he talked business with Eric and Brian (who grabbed mine and Leah's asses as we passed). The boat headed to open water as Leah and I lounged. The three called us back a few minutes out in water and we got started. I first had to pull Eric's cock through the zipper and discreetly suck it down low in case we ran into another boat, Leah did the same for Brian. Once we got far enough out in water Eric decided it was a good place to stop and we all headed below deck. It was incredibly spacious down there and complete with a bed at the far end with mirrors around one side.
Arif told me to get undressed for us and I did, once my bikini was off I was ordered to bend over the bed. The men fixed themselves drinks behind me and then I was surprised as I felt a finger slide up my ass. It was Leah behind me who was now nude with a strapon that must have been in her tote. The guys watch as Leah pushed the strapon deep into my ass. She fucked me roughly, holding onto my shoulders, as the others took viagra and got read for their turn with me. We shifted positions so Leah sat on the edge of the bed with me sitting on the cock, bringing my chest to my knees I also began to suck off Brian who stood in front of me. Leah told me she wouldn't be doing the work so I had to bounce by butt as Brian facefucked me. Eric and Arif followed suite and I tugged on their cocks. After a bit of this Brian took Leahs place fucking me, with Leah attending to my mouth, and eventually Eric and Brian switched a while after.
I ended up with Eric shooting his load up my ass and Brian and Arif cumming onto my face. Leah took a bit longer, when she was satisfied she took off the strapon and pushed me onto my back and straddled my face. The guys watched as Leah rubbed her clit until she squirted all over my face. After that Brian retrieved a set of bungee cords and they tied me to the bed before retreating back above deck. They spent the rest of the day on the boat, still making time to come below deck and use me sometimes by themselves or in groups. The most memorable was when a soaking wet Leah (presumably from taking a dip in the water) came and used me like a washcloth, I had to lick her feet, armpits, and ass so she could finish cleaning up. We returned to the dock late night.
Leah got a ride home with Arif so as I walked backed to my car alone. The sun was down so it was freezing in my denim shorts not to mention my ass was a bit tender. There were a couple of drunk college aged guys parked a few spots away from me that beckoned me to come drink with them. I was already very passable and these guys were drunk so I figured I didnt have anything to loose, I could use a drink. I walked over and the two told me they were they were the last remaining from a beach party and wanted to finish off the last of a handle. I had a few drinks with them outside and then one said "Hey don't you think you might owe us a little something for the booze?" He stood close to me I could smell the vodka on his breath. I tried changing the subject with the fake high pitched voice I had been fooling the two with. "God I'm freezing" with that the guy started rubbing my thighs; I stepped back fearing that if he had gotten to close to my crotch theyd of relized I was a guy. I bumped into the other one walking backwards. I was really nervous at this point so I figured id appease them. I got on my knees and undid both of their zippers. They were drunk so their thick, lazy cocks both took forever, I would blow one while jerking off the other and switched routinely until they both finished. I then quickly retreated to my car and left thinking about how I had just escaped a beating, rape or something akin.