Pimped: What did I Get Myself Into

The fantasy of being pimped and used had been one I had for a very long time. After building the internal desire for some time I decided it was time to pursue this fantasy. I put out multiple ads on several sites looking for the right match to find a real pimp that would pimp my sissy ass out. All I got in return were a bunch of guys looking to hookup, none really seemed to be focused on what I was really looking to find. At the same time I was posting ads I would browse as well, I came across an ad posted that a pimp and his partner were looking for a sissy subordinate that they would feminize and pimp out. Sounded like a perfect fit so I responded right away and awaited the reply.

The next day I saw a new message in my inbox, it was a reply to my response. A touch of anxiety came over me as I hurried to read the message. The response was exactly the situation I was looking for, he was not looking for any personal hookup or anything other than a new bitch to pimp out. He said to send in a few picture and reminded me that he was not playing any games. He also told me I better be fucking around wasting his time.

I sent him a few pics, I promised him I was not fucking around or wasting his time. I let it be known that this is exactly what I wanted. His next reply was pretty short basically his address and time to come over. He told me he wasn't sure I would make it but that he would let me try out for the position.

The location was on the other side of town so it was a bit of a drive to get over there. It gave me quite awhile to assess my situation, also there was time calm nerves that were going completely crazy. I arrived at his apartment after about an hour drive. The apartment was located in rough part of town and was dressed in my sissy outfit, at this time I didn't have any makeup just a short dress actually the same one as in the pic above, a wig and breast forms. I was really just starting to become a sissy so I didn't have nearly the supplies I have now. I pulled up to the gate and had to dial his apartment form the key pad at the gate. My fingers were shaking to push the buttons. He said nothing and just opened the gate. When my car stopped int he parking spot and I put the car into park the anxiety hit me hard. I took a few deep breaths and reassured myself that this is what I had wanted.

The walk from the parking lot to the door of the apartment was terrifying. When I came into the apartment it was him and his wife. He was a black guy and she a hispanic woman. They were older than me but not a whole lot. The pimp looked at me when I walked in and told his wife that she needed to take this bitch to the back and fix her up before he would deal with me. She took me back to the bathroom and sat me in front of her mirror on a stool. She was very nice and pleasant to talk with. She gave me a complete make over. I have never had an experience really having a makeover. She did my make up, styled my wig, adjusted my forms and really did an amazing job. This is probably the first time that I really felt pretty. I couldn't stop looking at myself in the mirror. The experience felt really nice, this was completely new to me. I was feeling very feminine and sexy but the feeling of being a pretty girl was the one I remember the most.

So after the makeover she takes me back out to the living room where the pimp was sitting on the couch smoking weed. He said something like "this bitch turned out pretty good, now turn around so I can see your ass". I gave him a spin around as he eyed my body. He looked me over for a minute and told me to come over closer to him. Then he told me to get on my knees in front of him. He stood up without saying anything and pulled out his cock and put it in my mouth. He was really degrading telling me to suck his cock and prove that I could be his slut. He was telling me things like I better love sucking cock and that I needed to prove I was the right bitch for him. He told his wife to film it they wanted to make sure to have me sucking his cock on video. After she took a bit of video of him degrading me while I suck his cock she tells him that is enough. He quickly pulls his dick out of my mouth and zips his pants up. Nothing more is said. He said the he was done and that he has seen enough.

She takes me back to the bathroom to gather my things so I could leave. He comes in there while I am getting ready to leave and says "I hope your know what your getting into bitch, there's no turning back now" while pointing my face. He tells me to come back the next day so he can put my ass to work.

I was so nervous about the next day, my head was spinning with so many different thoughts. The whole experience felt really strange yet satisfying, I felt like I was accomplishing a major goal. The feeling after having a full makeover was incredible I had never really seen myself that way before, then the excitement of the pimp and not knowing what would happen next felt great.

The morning came and I headed straight over, his wife did the full make over again. She did another fantastic job. I was again feeling very pretty. After she finished she brought me out to the living room where the pimp was siting on the couch smoking week. He looks me over when I came out and says this bitch turned out good lets get her ass busy. They took several pictures of me to post and to send out. I was just sitting there on the couch while they went to work. The pimp was steady smoking weed and his wife was working away on a laptop posting ads and emailing clients. I just sat quietly on the couch looking very slutty, yet very pretty, from the makeover. In between them answering replies to the ads and their clients emailing them, the pimp was making weed deals too, occasionally going out to the parking lot to make exchanges. This was all a giant change from my typical middle class area.

Then the silence is broken, his wife say they have someone coming for me. The wife tells me I can only meet the guest in the bathroom. She says I can only suck his dick and not to let him fuck me. If he wants to fuck he needs to talk to her. I agree and we all wait until there is a knock on the door. They send me to the bathroom to wait. I was so nervous just waiting sitting on the stool waiting for the door to open. Finally I see the knob turn and in comes a hispanic guy to see me. I am seated on a stool in the bathroom. He walks right up, there was no talking, and starts rubbing his dick with one hand and grabbing my tits with the other. I reach out and start stroking his hard cock while he grabs the back of my head.

I kneel in front of him and start slowly sucking his cock. Steady and deep I am giving him a nice wet slow blow job. He is leaning back enjoying it alot. His cock is sliding all the way down my throat. He had a nice size hard cock, I was completely focused on making him happy, I really wanted to do good with my first cock they had lined up. Then he stops and pulls his cock out of my mouth. He tells me he wants me to bend over so he can fuck me. I told him I can't fuck unless he talks to the mistress. He leaves the bathroom to go talk to her. Then she comes in there and tells me I can fuck him but I have to go to mattress in their bedroom next to their bed. This was a one bedroom apartment. She also tells me not to touch their bed she doesn't want my slutty ass on their bed.

We go to the mattress, I apply some lube to my ass and shove a finger in to make sure I am ready. I get in a face down ass up position on the mattress. The guy wastes no time shoving his hard cock cock into my ass. It was slightly painfully but that quickly gave way to pleasure. He was pumping my ass hard occasionally slapping my ass. I felt so dirty face down on the mattress on the floor getting fucked not knowing anything at all about who this guys was. He was really using my ass as he pleased. He gave me a few more hard pumps and I could feel his cock pulsing as he started cumming. He pulled out of my ass and quietly put his pants on and left the room. I waited in there until the mistress came and told me I could come out. She took me back into the bathroom to clean up my make up and let me know that some one else was on the way.

There were two or three guys that came that first day. In between guys coming over they had me practice walking and acting more feminine. I would practice walking around their living room and the mistress would slap my ass or yell at me if I was walking too manly. She would always repeat to keep my elbows pointed in and hold my shoulders back. She would also make me talk in a feminine voice. If my voice was too deep she would make me kneel in the corner or slap my ass.

The pimp didn't do a whole lot at this point he would just sit on the couch and smoke weed. His wife did most of the work. I guess his main role was to be the security in case something went wrong. I guess knowing he was out there made me feel more comfortable about strange men coming in. He was always checking me out though. He might say stuff like your ass is looking good today bitch, or I hope your ready to work and sometimes things like these guys gunna wear that ass out today. Those comments became more and more regular. In between customers, when not practicing walking and talking I would be sitting on the couch as well just trying look sexy. I really did not ever talk alot mostly because I was nervous about my voice.

I was coming over there pretty regularly the next couple weeks. Sometimes I would arrange to come over there on my own others the pimp would tell me when to be there. A few guys would come by every time I was there, there were already quite a few repeat customers coming. It was still getting a huge rush every time they would tell me that someone was coming, I would make a final preparation to my looks and make sure my ass was ready then either take my position on the stool or the mattress on the floor. If it was the mattress on the floor she would always come in and check it after a guest would leave.

She would always make a point to tell me to keep my slutty ass off their bed. I never dared to touch that bed occasionally a guy would try to sit there and I would have to quickly get him moved and straighten the comforter. I always felt like a big slut coming out of the back room to take my place back on the couch after a guy would leave. Walking back to the couch I could always feel my freshly fucked ass rubbing against my thong. That was a big turn on for me. The pimp would usually eye me up and down with a lustful look, his wife would be talking about what time the next person would be coming. Sometimes passing on a compliment from the guy that had left.

The pimp and his wife really seemed to like having me there. There was a bit more interaction between us all over this time. They were friendly but firm in the situation. I think the situation was working out pretty good for them.

I enjoyed being there as well, I really learned alot about makeup and acting more feminine. His wife got me a pair of heels to practice walking around in (unfortunately those were lost to a later purge). They purchased new make up and outfits for me as well. Everyday over there would start the same she would take me to the back give me and outfit to wear and do my makeup and hair. I would learn something new every time. She had owned a small clothing and makeup retail shop a while back. That is where she had learned to do make overs. I always had a wonderful feeling looking in the mirror after she would finish. I can still hear her voice in my head giving me tips.

Then after those few weeks went by the pimp started emailing me trying to get me to tell his wife I wanted to fuck him. I told him I couldn't do that and he would email saying he really wanted to fuck my ass.

One day as I was about to get ready to leave, I was in the bathroom. The pimp kinda snuck in behind me, it was a very short space between the counter and the wall behind me, the toilet was beyond that area so I assumed he was headed in there. He stopped behind me and started grabbing my ass. I started grinding my ass into his crotch. I was wearing a short skirt, thong and stockings. My ass had already been used so it was well lubed and ready. I was horny too and wanted his cock. He peaked out the door to see if his wife was looking then he pulled his cock out, I pulled my panties to the side and he slid his cock right up into my ass. I was pushing my ass back onto his hard cock.

He grabbed my hips and was pulling him self deep in my ass. It felt so good to feel him inside my ass. It felt shameful to be allowing this to happen but I had been secretly wanting him to fuck me. I would be sitting on the couch thinking about it from time to time. His wife abruptly walked in and saw what was going on. She got mad and told me to leave. They were yelling as I left. He emailed later saying they split up and was trying to hookup but it never really worked out after. That was the last time I saw either of them.