Prostitute Stories: Short Stories
One Pump Chump
This was a super easy pick up. I’m driving downtown near the government buildings, usually nobody here at night and it’s very far away from any of the regular tracks. Nonetheless there she is a young brunette, not too pretty but definitely not ugly, with a nice enough body. I stop she runs up to the window and asks for a ride, hops right in. She agrees to come to my place this is about a 15 minute drive. I put on some music, we talk and get to know each other. As soon as we get in she undresses immediately and I pay her. I can tell just by the way she’s acting this will be a good date. She kisses me, which is already a good sign she seems genuinely horny. I throw on a condom place my dick inside of her, I literally push inside of her once. . . and blow my load immediately.
When I cum every girl tells me the same thing they’re shocked by how strong they can feel it. My dick starts pulsing apparently it was very obvious this girl knew immediately, she looked me right in my face and laughed out loud. She wasn’t trying to be mean she just couldn’t help it. She was laughing so hard she couldn’t stop even going so far as to put her hand over her mouth. She just kept repeating “Im sorry, I’m so sorry, I can’t help it.” With tears rolling down her face.
See here’s the thing this was a period in my life when I masturbated compulsively I felt I couldn’t help it. One of the side effects of compulsive masturbation is a complete lack of stamina. The good news for anyone else who suffers from this is you can cure it you just have to stop Masturbating. You need to find an activity that replaces masturbation trust me it can be done. This hilariously embarrassing event was my rock bottom and it cured me of my masturbation problem to the point where I can now brag these days of having much more stamina than the average guy. Just a bit of encouragement to those who may be dealing with this. Oh yea In the end I had to spend another 15 minutes driving her all the way back in complete silence. I did not give her a tip.
The Toilet Slut
A few months ago I picked up this girl that I never date. I’ve seen her around but nothing attracted me to her so I always passed her up. Ok let’s be honest here she’s ugly as sin and wears a ton of makeup. (I honestly don’t mind if she’s ugly but damn I can not stand alot of makeup). I was desperate that night and decided to do a date. From the moment she steps in the car she will not shutup. She’s talking about any and everything, not a conversation just talking. I get a room at this super cheap shitty motel they don’t do hourly but it’s only $40 for the whole night. This should give you an idea of how shitty it was. Lets be clear I didn’t pick her up for her looks but I was hoping she would still be a good fuck. She takes her clothes off and it turns out has this incredible body. She looked mid 40’s but had the body of a 20 year old. Perfect hips, waist, and great tits now I can’t wait to fuck her. I shouldn’t have gotten my hopes up she was terrible in bed, she gave me a decent blowjob but everything else she was just stiff as a board. We finish fucking and she’s still talking, eventually heading to the bathroom.
Now I’ve got to take a piss and this chick has been in the bathroom for like a half hour. I’m like “Hey what are you doing in there? Can you come out? I’ve got to piss bad”. She Yells from inside to open the door to come in. I walk in and she’s just sitting on the toilet masturbating. I’m like WTF?? She just gave me the worst sex ever out there but she’s in here trying to get herself off? Anyway I try not to think about it I need to take a leak.
“Get up I’ve got to go.” This chick looks up at me, grabs my dick and says, “Just pee in here”, pointing down and spreading her legs making a little opening into the toilet. . . Ok that’s weird but I don’t care I’ll go along with it. Holding my dick she aims it down. I start pissing and it’s perfect aim right in the toilet and then she tilts it up aiming at her pussy. She brings up her other hand and starts rubbing her clit. Then she just started spraying it up and down her body. I’m pissing all over her stomach, her chest, her hands. When I was close to finishing she put my dick right in her mouth until piss was pouring out the sides and down her chin. The entire time looking me right in the eye until I finished. She swallowed the last bit shook her head back and forth and exclaimed,”Whoa! That was good ok I’m going to clean up and we can go.”
What the fuck was that!? Now you have to understand I never asked her to do any of that and golden showers isn’t really my thing, she completely took it upon herself to do that. I’ll admit though it did turn me on not because I was into it but because she was so obviously enjoying it.
Phone Sex
This was probably my 3rd or 4th date with this girl named Shi. She was this streetwise Italian girl who lived in the hood. She wore cornrows and talked like a thug but she was just a mom working to feed her family. She was short, thick and curvy, never wore any makeup personally I loved the way she looked. Anyway it’s a short drive over to my place she likes to get down to business no small talk or anything. So we get in strip down and I start fucking her missionary style on my couch. The phone rings and she reaches behind her. I’m thinking she just wants to see who’s calling. “Ah shit it’s my husband”. She answers the phone so I stop. “What do you mean where am I? I told you I’m going out to make some fucking money.” She looks at me and motions me with her hands to keep going. Ok that’s weird but I continue “Ok baby you got to hurry up cus I’m working.” She’s spreading her legs and grabbing my ass looking me dead in the eyes as she’s having this conversation. On top of that she’s not even trying to hide it. It sounds clearly like she’s getting fucked which she is. “Yes I’m working right now. Yes right now and you need to hurry up because you wasting this man’s time.Wait he did what? He did what!? Put that boy on the phone!”
She hops up and starts pacing back and forth. I’m lying on my back trying to keep my dick hard “Boy don’t you let me find out you left the house when I told you not to. You better be telling me the truth when I get home I’m going to whip your ass good.” She walks back over and sits on my dick and starts riding. “Ok you better listen, now put them on the phone and let me say goodnight . . . Goodnight mommy loves you guys I’ll see you tomorrow ok now put daddy back on the phone . . . Ok baby don’t worry I’ll be home in a little bit. Yea I’m just going to finish up here with him and then he’s going to drop me home ok? Ok baby I love you too, see you soon.” She hangs up throws the phone on the floor and without batting an eye she’s like “Come on spank that ass, give me that nut daddy, come on give me that nut!” I came right away, got dressed and dropped her back off to her husband and family. I did not give her a tip.
Hottest Sex Ever
So after a few years after I moved to Cali I’ve become very accustomed to the 2 main tracks the girls walk on around here. One day after doing a date this girl asked me to drop her off in a neighborhood I’d never been to before. I get there, drop her off, and as I continue to drive through the area I start to get some really strong hooker vibes from the women walking around. I slowly realize, holy shit this is a third track I never knew about. The next day I couldn’t wait to get out of work and explore this new track, because basically a new track means meeting a ton of new girls. I’ll never forget the first chick I met in this neighborhood. She was my favorite type, just complete street trash. This kind of girl is one the reasons I go to the street instead of Backpage. She was extremely skinny wearing this one piece denim shorts getup with a deep v neck. She had on fishnet stockings with tears and runs all through them with some leather high heeled boots on. She was Latina, sexy, with beautiful brown skin and long curly black hair. She was checking her makeup when I pulled up. It was an easy pickup, not another car in sight. I just pulled up and rolled the window down. I can usually get a feel for a girl by the first few seconds of meeting her, especially the first words that come out of her mouth. She walked very sexy towards the car, bent over, leaned in and said “Do you have have a big dick?” I told her to hop in if she wanted to find out.
She hoped in and we took off. She gave me directions to a motel she was sharing with an old lady she referred to as “Grandma”. Without asking she unzipped my pants, reached in and started jacking me off. I looked over at her like she was crazy. “I wasn’t joking I want to see your dick”. She leaned over and spit on it, then started jacking me hard and fast. Mind you I’m driving the fucking car while she’s doing this and she hasn’t even said a word about money yet.
“Ok you need to calm down you’re going to make me cum before we even get started”. She pulls her hand out of my pants and directs me to “Grandma’s” room an old lady opens the door and gives us a warm greeting.
She’s in a motel room but it’s decorated with her personal things. Pictures hanging on the walls, dishes and a hot plate etc. She’s clearly living out of this motel room.
“Ok welcome come on in. Give me a second and I’ll give you two some privacy.”
She starts cleaning the room a little and grabs a pack of smokes.
“Ok you guys can use the bed please just don’t touch anything”.
Grandma heads to the bathroom to give us some privacy. The second the door closes my date grabs me by the crotch and starts fondling my balls. She’s stroking my dick and sticking her tongue down my throat.
“I’m a nasty bitch. I like to get fucked hard. Do you like rough sex?”
“Yea”
“You ever fucked a girl in the ass”?
Holy shit this chick is crazy again she still hasn’t said a word about money.
“Don’t take it easy on me ok? Smack me, choke me, pull my hair, call me a bitch. I can take it I love that shit!”
She pulls open her v neck, revealing her small but full perky tits with thick long nipples. I start sucking her tits.
“Bite my nipples, hard.”
I start biting and sucking them hard and she moans wildly. I rip the rest of that v neck shit off and god DAMN! This bitch is so skinny. I tend to like thick girls but she really pulls off this look she’s got a sexy body, nice tiny waist, flat stomach, and curvy hips. She climbed up on the bed, pulled my pants down and stuffed my dick all the way into her mouth until her nose was touching my crotch. No gag reflex whatsoever! I literally grabbed her by the neck and thrusted my hips back and forth into her face as if I was ramming her pussy. There was a steady stream of saliva pouring from her mouth and my balls. We made a complete mess of this woman’s bed and she loved every second of it.
“I can’t wait baby I need that dick in my ass.” She grabs some lube, bends over and smears it all over her asshole. I slap on a condom slide right in no problem. She said she liked it rough and I wasn’t about to hold back once that asshole opened up for me I started pounding her from the back like a jackhammer. She was screaming her head off. Actually both of us were screaming the filthiest shit at each other.
“Pull my hair motherfucker!”
“Take that dick you fucking bitch”
“Shove that big cock in my asshole!”
“You goddamn nasty whore!”
Just like she wanted I’m pulling her hair and smacking her ass hard, she’s screaming and keeps reaching back to smack me. The bed is rocking hard, sheets and pillows are flying all over the place, and the headboard is smashing into the wall. I think we both got so caught up we forgot all about Grandma until . . .
“Ok that’s enough! You goddamn faggots are disgusting! I will never let you use my room ever again! Look what you did to my fucking bed! Wrap it up and get the hell out.
My date started pleading with Grandma.
“Please, I’m sorry, it won’t be like that again I’m sorry we were making too much noise. Please don’t kick me out.”
“Just Hurry up and finish and get him out of here!”
Dammit that sex was fucking incredible and this old lady just killed the whole vibe. As I’m listening to them fight I look down at my hands wrapped around her tiny little waist. My dick stiffens up feeling the heat inside her tight warm asshole. Then my thoughts start to drift back to something grandma said. Did she just call us faggots? Why would she say that? Clearly I’m fucking this hot ass chick . . .
Yes this is going exactly where you think it’s going. I look back down at my hands wrapped around her tiny waist again and think to myself. Nope there’s no way look at the waist and the hips on this girl her body is sexy as hell. Then I look further down and start to wonder. Why am I fucking her with her g string pulled to the side? Did she do that or did I do that? Why wouldn’t she just take it off like a normal person?
“Ok I’m sorry baby we’re going to have to wrap this up she’s getting bitchy.” I slowly pull my cock out of her and stare at her gaping asshole. There’s no way! She has tits! Natural jiggly tits with huge fucking nipples! I decide to pull her panties completely off. As soon as I did that she started rubbing her . . . vagina? I don’t know I couldn’t see her hand was in the way. So I grab her by the legs and flip her over missionary style and yup sure enough now that I had her legs spread open there was no doubt about it. This fine ass girl’s cock and balls were staring me right in the face. I just had some of the best sex ever with this girl, unfortunately I’ve just found out that she in fact is actually a guy.
Now based off of all my stories up to this point it’s probably safe for you as the reader to assume that I am straight. Me as the actual person in this situation have also assumed that I am straight. Now the fact that I’ve actually been fucking a guy for the last 20 minutes doesn’t make me any less straight, after all I didn’t know, she looks exactly like a girl. He has fucking hips for god’s sake! However what I decide to do next now that I have all the information well there’s an argument to be had about my sexuality based on the decision I’m about to make. Still horny, still hard as a rock with my dick in hand, If I chose to continue fucking this person does that make me gay or straight? I mean she still looks like a hot street whore If I just don’t look down and keep going I can still be straight right? No If could enjoy the sex that much with a pair of balls so close to mine deep down I must have known. Shit! Am I going to have to come out to my parents!? Well here’s the thing recent information on the topic suggest that we’re all actually on some kind of spectrum. Who’s to say who’s straight and who’s gay? Why even label this? I mean it’s possible some of my sexuality has been conditioned by popular culture, the media. So really human sexuality it’s a fluid thing right?
I wish I could tell you I put as much thought into this as my writing suggest but in actuality, in that moment, I flipped her over saw she had balls and thought. “Oh no! Shit this whole time I’ve been fucking a guy!?” Then I immediately stuck my dick back into this dude’s waxed asshole grabbed him by his long feminine curly hair and said.
“Give me that pussy you fucking bitch!” Then I choked him and pounded his asshole until I was able to finally cum. The second I came my clarity rushed back and I was like, ok I’ve got to get the fuck out of here. I threw some money on the nightstand and left. The truth is after that happened I went back to fucking random women I picked up off the street like I always have. I’ve barely given it another thought until I decided to tell this story. BTW it turned out the area I was in is a special track where only Trans street walkers work so just about all the girls I was looking at had a little secret.This Louis CK joke actually sums up this entire story. and my feelings on it, perfectly and more succinctly than I ever could in just 30 seconds.
Oh and one last thing. I know there are a bunch of you guys who read this and thought there’s no way that could ever happen to me. You must have known. I would’ve thought that too before it happened to me keep in mind I wasn’t drunk or high or anything like that. I was just horny If this could happen to me it could happen to anybody. Now whether or not you continue to keep fucking after you found out is up to you. LOL! I always try to tell the truth in my stories so I would be a fucking liar if I just decided to change that part or leave it out.
-H123