My night with Jan and her two kinky men
Introduction:
My first time as a tranny hooker
“Mid 30’s couple looking for open minded crossdressers for kinky and unusual scenarios. We provide the costumes and a full makeover. Email for details with a picture. If we think you are a good candidate, we will reply with a phone number.”
Since I had no plans for the evening, I emailed the anonymous address including a photo of me and shortly after received a reply with a phone number from a woman named Jan.
When I called Jan, she asked me about my experiences, specifically any crossdressing I’ve done and if that involved play or sex? I told her I had dressed in private many times but have wanted to experience sex with a man when I’m completely transformed into a woman. This seemed to get her excited and she started telling me how her husband enjoys fucking men that she (his wife) fully transforms into women. They have various scenes and scenarios but those are a surprise because her husband never decides until a few hours before. Jan usually shoots video. We talked some more and she talked about how nothing excites her husband more than a virgin he can deflower.
Jan said she would love to have me come over. The only requirement is that I am completely shaven. She would take care of everything else.
I arrived at their house, parked my car as instructed and rang the doorbell. Jan opened the door wearing extremely tight jeans with heels and a very low cut tight white t-shirt. She took me through the master bedroom and into a large bathroom connected to a huge closet of all sorts of women’s clothes.
Jan said she had been thinking about how to transform me and decided to do a classy hooker dressed in white. She told me strip and recommended I let her insert an anal plug since her husband was well hung and he sometimes likes to just ram it in. Wow, this might be an intense night I thought to myself. She lubed a medium plug and told me to squat. She slowly pushed it in while caressing my cock. It was so hot I almost shot my load.
Jan went an picked out my outfit and laid it out on the bed. She said we would get dressed and then do makeup. First she had me put on some white thigh high stockings, not fishnets, but they did have nice lace on top. Next came a tightly fitting white corset that had a see through halter top. She connected the garters to the thigh highs and then filled the corset with breast forms. I was getting really turned on and had a raging hard on. She said that would be a problem since I needed to look feminine and wear panties. She kneeled down and started sucking me off. At one point, she removed the anal plug and started fingering me. It felt so good but I couldn’t hold out anymore and shot my load in her mouth. She swallowed every drop and then reinserted the anal plug.
At that point, she helped me into some silky crotchless white panties with a special band that would wrap around my cock and pull it between my legs so that I would not get a hard on unless her husband removed it. The heels she picked out were gorgeous white sandals with a 4″ heel. She then got a text message on her phone saying that her husband had invited a friend over and that they would like to start the evening doing some gloryhole play in their basement. I asked if he was serious and Jan said they have a play space that includes a gloryhole and 3 video arcade booths.
Next came a white dress that hugged my boyish curves but made me look so feminine. I also was told to put on some long white gloves, the kind that go all the way up the arm. Jan said this eliminates the need to do my nails. Jan pulled out a long blond wig and attached it to my natural hair. I then sat down in front to the bureau as she did my makeup. After about 10 minutes, she had me apply cherry red lipstick and helped me with a necklace and earrings.
After spraying me with perfume, she had me bend over so she could remove the anal plug. She then grabbed what looked like a ball with a rubber needle like pointer. I asked about it and she said she would fill me up with lube so I would be ready for anything.
She said both she and her husband have a smoking fetich and handed me a purse with cigarettes, lighter and a a bunch of makeup including a tube of red lipstick for touchups. Then she said I would watch her get dressed for the evening.
She went back into the large walk-in closet and grabbed some things. She then stripped down to nothing and started with a trashy looking shiny gold thong. She said she sometimes likes to dress up as a white trash whore. She started putting on quite the outfit as I practiced walking in my heels. After the thong she donned an off-white garter belt and attached some black slightly ragged fishnets. I almost started laughing but was too busy looking at her tits. She put on some 5″ stiletto rock and roll boots that made her look like she should be in a dirty bar. Next came a see through black shirt and a denim mini skirt that was so tight and high that it showed the dimples of her ass.
Jan said I was ready so we walked through the house and down some narrow stairs leading to the basement. The first room we walked through looked like a dungeon then we passed through a medical room and finally to a hallway where I heard the audio of several pornos. There were three booths. Jan led me into the middle one which was large enough for the two of us and had holes about 5 inches round on each side. She picked up a video camera and told me to sit on the chair, cross my legs like a lady and start smoking. I opened my purse and the silver cigarette holder taking out a long white cigarette. I’ve only smoked a few times before so I hoped I would do it right. After lighting it, I took a slow long drag and slowly blew it out. Jan said I looked incredibly sexy and then I noticed the red lipstick on the cigarette. I really wanted to touch myself but Jan said my cock was off limits.
After a few minutes, I saw a very hard and large black cock come through one hole. Jan said it was a great cock that she had sucked and fucked before. I was hesitant but so turned on so I took the cock in one white gloved hand while holding the cigarette with the other. I blew smoke on it and then put out my cigarette on the floor.
After a minute of jerking him, I could not wait so I immediately took it into through my lipstick covered lips and started tongueing the tip and finally took as much as I could into my mouth. As I was sucking this amazing cock as deep as I thought I could, Jan set down the camera on a shelf so that it would continue filming me. She then grabbed the back of my head and started forcing my mouth further onto the cock. She said, “take it all whore or you’ll be sorry.” It wasn’t scary to hear that but I knew the night just got a little spicier for sure. She said, “relax your throat and just take it.” I tried and tried until my eye liner starter running from gagging. Somehow I was finally able to relax enough to deep throat the giant black cock. Jan said “good whore” and I felt like I accomplished something. It kept getting easier as I continued to pump this faceless man’s dick all the way until his pubic hair was in my mouth. If you’ve never been able to take someone that deep, it’s a rush to feel a warm cock down in the bottom of your throat.
I kept at it for another 5 or 6 minutes when I heard him starting to moan. Jan told me to start jerking him off and make sure he squirted his hot cum onto my face and lips. Well, soon after that, he came like I’ve never seen someone cum before. It seemed like a firehose as it hit my cheeks and lips. As he finished up, I licked his cock and made sure I had it all. He pulled back and Jan brought the camera in close to capture my messy face while I moved my tongue around and licked my lips.
After we got some nice video, Jan took me into a bathroom where she told me to wipe off and touch up my makeup like a lady. It took a while and Jan helped but we finally had me looking really hot again. Jan told me I looked great and asked me if I were ready to be fucked hard and rough by two men at once? I told her I was really turned on but a little scared because I’ve never done something like that. She handed me a blue pill and a glass of water which I swallowed. She said it was a strong drug that relaxed all the whores that came through. Fairly soon, I was feeling really weird but very horny and relaxed. I even felt like my love hole relaxed.
She led me into another room that had a plastic covered bed in the middle and a table with all sorts of sex toys like dildos, nipple clamps, whips and some blindfolds and gags. She told me to sit on the edge of the bed and walked away leaving me in silence for a few minutes until I heard footsteps. Jan’s husband and their black friend entered and were completely naked. Jan’s husband told me to light a cigarette and smoke it as nasty as I could so he could get hard again. I obeyed and even blew smoke on his hard on.
Next he told me to take off my dress but leave the corset, jewelry, thigh highs, panties and heels.
Before I knew it, I was kneeling on all fours on the bed and all of a sudden, I felt my panties being caressed and then slapped. It felt so good and I knew Jan would be getting some great video of it that I could enjoy later.
Then I felt a cock enter my ass. It hurt to the point of me letting out a whimper but it didn’t matter since he started pounding his cock in and out of me. At the same time, I felt someone open my mouth and shove another cock into my mouth. There I was in lingerie and heels getting fucked in both holes. After about 20 minutes, they swapped and I felt a new cock in each end. It must have gone on for another 20 minutes when the Jan’s husband pulled out his cock as did the black man who was penetrating my hole.
Jan’s husband told me to lay down on top of the black man. After I got into position, I helped him insert his cock into my ass. I started riding it as Jan and her husband watched me grind and pump on this amazing cock. Jan’s husband walked over to me and removed my panties allowing my cock to spring into an erection. He told me to start jerking myself. Well, the entire scene was so erotic with me fully transformed into a slutty woman, riding a black cock with my cock bouncing up and down while Jan her husband watched. As the fucking slowed down, Jan’s husband positioned himself on top of me which made me wonder what was happening since I still had a cock in me. He asked me if I had ever ben double penetrated to which I shyly said no. “It’s your lucky day” he said. I wasn’t stressed since the drug had fully taken effect.
As Jan’s husband maneuvered himself onto me, he put my legs over his shoulders which really turned me on to see the heels up in the air. He slowly worked his cock in next to the black cock which took a good 5 minutes until I was stretched enough. Then they both started to slowly saw into me until I was being pounded so hard and fast that I started to get dizzy. After a good 10 minutes of sheer crazy fucking, Jan’s husband pulled out and shot cum all over my face. One spurt hit me in the eye after which he said, “take that you worthless piece of tranny trash!”
I was completely overwhelmed sexually by now and Jan said that was one of the hottest things she has ever seen. With a face full of cum, the black man continued to pump me. I could not believe how wide my hole had become. Since my hands were busy holding myself up again so the black cock could keep hammering me, Jan came over and started jerking me off. I lasted for maybe 10 seconds before shooting my load into her mouth as I was being fucked. For sure I thought the black man would not be able to hold it anymore but he kept fucking my pussy as Jan motioned to her husband to come over and then shared my cum with him through a long hard kiss.
The black man was finally starting to moan and I thought for sure he would want to cum on my face too but he decided to fill my pussy up with his juice.
It felt so warm and I felt so feminine making these men have such a hot time. As he pulled out, Jan came over and started cleaning up around my hole. It took me over the top. She then inserted a huge anal plug in my ass in order to keep the cum inside. I didn’t mind and wondered if they had something else in mind.
Jan told me to go to the bathroom and get cleaned up and dressed. She said I needed to look good because we were going out.
I peed and got completely fresh before coming out of the bathroom. Only Jan was there but she said I was such a good whore than we were going to a real video arcade where she and her husband would pimp me out for cash.
