This is an encounter I had with a 19 yr old hooker a few years back. I was driving around looking for a girl when I saw a hot looking young black girl walking on the street. At first I thought she was just walking and not working, but after driving by a few times relized she was walking around the same block and was looking at me each time I drove by. Now I'm pretty careful when it comes to picking girls up. I don't just pull over on the main street, I drive up a side street and park, which is what I did. Now most girls know to go up the side street and get in the car, but this one just looked and walked by! I drove by her and nodded and she nodded and motioned for me to pull over but I pointed to a side street and drove there. She walked over and hopped in, looking a bit nervous.
Now this girl was well dressed in tight short shorts, and tank top, sneakers and socks, and was well groomed and clean, not your average street walker that's for sure! I asked if she was a cop and she replied no and I asked her to touch me which she did hesitantly and I groped at her tit. She introduced herself as Star and when I asked her how long she'd been hooking she said sheepishly that this was her first time!! Turns out she wanted to make some quick cash and loved sex and even though she had applied at an escourt agency, needed cash that day, so decided to go out on the street! Now I've NEVER been with a girl that had never pulled a trick before and even though I had only been looking for a quick BJ, decided to make the most out of the situation! I asked how much she needed to make and she told me $150, that her and her mother were going to get kicked out of their place if they didn't pay that by days end. I made my mind up and told her I'd give her $200 if she wanted to spend a couple hours with me. Her face lit up and she asked if was serious and when I replied yes, told me she'd do whatever I wanted for that kind of money, as long as she would be back home by evening! Now it was only mid-mourning at this point so I knew I was in for a treat!
I stopped by a drive thru bank machine, took out some more cash and asked Star if she wanted to pick up anything before we went to my place. She asked what I meant and when I asked her if she wanted to meet up with her dealer first, she laughed and said she didn't use d**gs, aside from the occasional joint. What a surprise! She was actually genuine! I decided to take her back to my place instead of wasting money on a hotel, now I don't normally do this, I used to until one girl kept knocking on my door at all hours begging to give me a BJ for as little as $5! Not cool when you have a girl over from work! Anyways, I figured Star was cool enough not to do this and we proceeded to my place.
We got to my place and headed straight for the bedroom where we both stripped down and I was treated to the sight of her tight 19 yr old body!! She had nice firm C-cup titties, tight flat tummy, very tight, firm ass and was competely shaved. I got her to keep her panties on, brown micro-fibre, full bikini style and layed on the bed rubbing my little penis. I asked her to stand beside me and model a bit in her panties as I rubbed my dicklette to it's full 2". I asked her what she thought about my tiny penis and she giggled and said she thought it was cute! I told her I liked to be humiliated about it and she giggled and told me it was the smallest little peepee she had ever seen and she used to babysit a lot! She also said she was going to tell all her friends about this guy she was with that had the worlds tiniest cock! This girl wasn't as innocent as I first thought! She told me there was no way she'd be able to feel me inside her and laughed saying she now understood why I picked hookers up as no girl would ever fuck a guy with such a tiny dick for free! I was in heaven! This girl really knew how to humiliate a guy and kept on degrading me while teasing me in her panties. I asked if she'd make me sniff her bum and pussy through her panties and she she giggled and straddled me face. She ground her tight ass on my nose, asking me if I like the smell of her sweaty ass, telling me how hot she was walking around all mourning and sweating in her panties. I told her yes and she laughed and sat down on my face smothering me! Her ass smelt awesome, and I started rubbing my dickie even harder! She pushed my hand away from my dicklette and started rubbing it herself, as if it were a clitty and degrading me telling me to sniff her teen bum while she diddled my little clitty! It was too much and I started to cum all over her fingers, she said "Ewwwwwwwww GROSS!" and got up off my face. "Look at this mess you made bad boy! Lick my fingers clean!" I sucked all my cum off her fingers and she laughed telling me she'd never seen a guy so disgusting! She called me a filthy pig and then sat down on the bed and asked if she could have a smoke. She changed her attitude right away and asked if she was too rough on me. When I told her it was all good she giggled and said she enjoyed it too, telling me she had done this sort of thing before, on cam with a guy she met online. He had sent her humiliation videos and she mimicked what they did. We talked for a bit before she told me she had to go pee. Now I've played watersports before and loved it! So I asked if she'd pee on me in my tub. She was a bit hesitant at first, but finally agreed as long as I didn't want to piss on her!
I climbed into the tub, and as she went to take off her panties but I asked if she'd leave them on and pee through them. She squatted a bit over me and a few seconds later piss started seeping through her panties and ran down her leg. I placed my mouth at the stream and let her teen pee run into my mouth. "Ewwww, you one nasty fucker ain't ya! Drinking my piss like that!" I kept taking her pee into my mouth and swallowing letting some run down my front and soaking my crotch area. I rubbed her piss into the crack of my ass and fingered myself, using her golden necter as lube! When she was done she pulled off her panties and handed them to me and I got up and sat on the toilet and sucked her teenaged pee out of them as she took a quick shower. When she got out she asked me what I wanted to do next and I told her more humiliation back in the bedroom. She asked if I was going to shower but I told her it was more humiliating to let her pee dry so I'd smell like piss. She scrunched her nose up and told me she wouldn't be into blowing me or anything until I showered and I agreed, telling her I'd shower before we did anything together.
I asked her if she minded if I put some lingerie on and she laughed and said yeah! I went into my spare room and put some white stockings, garter belt, white lace thongs and a matching lace bra on, I walked back into my room to find Star sitting at the head of my bed smoking. She burst out laughing saying "You look fucking ridiculous dude! Holy shit! I can't believe you'd actually put that on in front of someone! Your FAT and gross, and that lingerie doesn't make it any better to look at! HAAAHAAAHAAA! Your little clitty looks like it belongs in those panties though! HEHE!"
I was totally embarressed and loved every moment of this hot teen humiliating me, she was a natural at it! "My friends aren't going to believe this! Can I take a couple pictures on my phone to show them?" I said yes as long as my face was covered and she told me to use her pissy panties to pull over my face! I did and she took several pictures, including a couple close ups of my little dickie! "They'll get a good laugh over these for sure!" I was so horny thinking about her friends seeing those pics that I started rubbing myself. She laughed and told me turn around and show her my bum. I did and she made me spread my butt cheeks apart and said "Ewwww!! You gotta huge bunghole dontcha! You must be a fag too and take big dick up there huh?" I nodded and and she laughed calling me a faggot. "Stick your finger up your butt like you did in the shower!" I did and frigged my ass for a few minutes while she finished her smoke and giggled. I asked if she'd finger me and she was hesitant but said okay. I grabbed some lube from my night stand and got on the bed doggy style and felt her put her index up my pooper. "Holy shit your loose!!! I can only get two fingers in my pussy, and it feels like I could put my whole hand up your faggot ass!" I moaned and asked if she'd try. "Seriously??!!" "Uh-huh" "Okay, I'll try, let me know if it hurts." She pulled her finger out and lubed her hand up and started working four fingers in! Now I had been fisted several times before and knew she'd have no trouble getting her slender teen hand up there! When she got to her knuckles I felt her thumb join her fingers and after a little working, her hand plopped into my ass! My sphincter was wrapped around her wirst like a bracelet and I moaned as she laughed telling me how wierd it felt! She started pushing her hand in farther and after me telling her to make a fist and fuck me, was in heaven as this teen beauty fisted my bum! I felt her hand open and then felt her turn her hand around and she started tickling my prostate with her fingers! I never felt anything so good and she kept this up for a few mintues before reaching under me and jerking me off with her finger and thumb! "Come on Tiny, cum for me!" she said, and cum I did! I squirted my jizz on my bed and she told me to lick it up while she fisted me some more! We moved down the bed so I could lap up my load of cum and she started pounding my ass with her arm! By the time I was done cleaning up my mess she was almost up to her elbow in my ass! "Good boy!" she said and pulled her arm out, keeping her hand balled in a fist though and I nearly shot through the roof as it passed through my raw scphincter! My ass HURT after her fist passed through it and I walked funny for a day after but it was worth it! She was a bit put off by how dirty her hand and arm was and rushed to the bathroom to jump in the shower again! I went to join her but she declined telling me to stay filthy like the pig I was!
When she came out of the bathroom I was laying on my bed smoking and kind if rubbing my soft almost inverted dicklette. "I think I've earned my money now dontcha think? I'd like to get home and pay my rent!" I was spent and went to change but she grinned and told me to dress over my lingerie! Now it was summer, and it was hot out, and when I went to grab a pair of pants she told me to put shorts on instead! I did and then went to put a t-shirt on but she told me to wear the tank top I was wearing earlier! Now not only could you see I was wearing nylons, but my bra straps were also visable! We went out to my garage and got in the car, I figured it wouldn't be bad, I'd just drive her home and then take off the lingerie before heading back! But it wasn't that simple! She asked me to stop at a store by her place and go in with her, but telling me if I didn't want to it was cool. I decided I was in a part of town I never went and walked into the store with her. Now there was a line up at the cash and I got a lot of wierd looks, not only from my attire, but also from my stink, as I didn't shower and as we drove I had started to sweat, bringing out the stench of Star's piss from earlier! We got back into my car and drove to her apartment building where she kissed me on the cheek and told me she had had a blast and hopped I would call her agian as she really enjoyed humiliating me! She wrote her number down and took off inside! I didn't bother changing in the car, and even took my tank top and shorts off, driving home in my lingerie, my car reaking of piss! I even went through a McDonalds drive thru and got a meal! The girl who served me didn't notice at first, but when she handed me my drink she seen what I had on and disappeared from sight. A minute later another girl came to the window and handed me my meal with a smirk on her face. I pretended to check out the contents of my meal as she left and I heard her and her co-worker breaking up laughing thru the window! What a turn on! Anyways, I headed home after that, and stayed dressed up until the next morning!
Star and I did get together several times after this one, but I'll share those in up comming chapters! She did start working at an escourt agency, and never turned another street trick aside from the one with me! She's now a successful dominatrix out east and we still chat through e-mail, her crediting me for getting her started in the world of domination!