[m]y [f]riend approached me about prostituting herself.

I feel kind of bad about this, but fuck it, had sex. (That starts at **** for those who skip ahead)

My friend Nancy has fallen on some hard times. Not the lost my job, can’t pay rent kind of hard times. No, Nancy went from being a pothead and weed dealer to dealing and doing harder substances. She’s lost some weight and word has kind of gotten around she’s the go-to for your poison of choice.

I won’t lie, I’d been trying to get in her pants since we met in high school. She was a curvy gal; 38 DDs, easily, and the body to go with them. Not fat, but enough meat on her bones to give you something to grab hold of. The closest I’d ever gotten was when she consented to show me some vids of her blowing her boyfriend. I’m here to tell you, Nancy has some serious skills.

So I’m sitting at work when my phone buzzes with a text from Nancy. It was a pic of her in red lingerie, tits spilling out of her too-small bra. She had thick, long hair that flowed around her shoulders. It was a dark auburn with streaks of red running through it. She’d lost some weight, and her color was a little off, but those legs still killed. Along with the picture was a message: “you busy after work tonight?”

I felt my pulse quicken, but was suspicious. She’d shot down every attempt I’d ever made at getting with her, so I wasn’t exactly ready to jump in with both feet.

“Maybe. Depends on what you need?”

I sat my phone back down and tried to focus on work. A few minutes went by with no reply, so I assumed she’d just been messing with me. Then my phone buzzed again. This time it was a pic of her laying on her couch. She’d taken it selfie style, her hair spilled out around her. She was wearing a plain white tank top that had been pulled up to show just the bottom of her breasts. “lol. What do you think?”

I sat there processing what was going on when another message came through. Similar pose, but she’d lost the tank top. She’d thrown one arm across her chest, keeping her nipples covered. “sex”

I blinked. It still felt like someone trying to pull something on me, but the hard on on my pants didn’t seem to care. “I might be able to help you out with that.”

I knew I was grinning like a idiot. I wasn’t about to question fate and why one of the hottest women I’ve known suddenly wants me to come fuck her. But questioning or not, the next message filled in the blank: “I’ma be honest man, I need about 200 bucks.”

Stopped me dead in my tracks. On the one hand, well … I had the money. I’d been wanting to get between Nancy’s shapely legs for so long I didn’t even really think about that. But, in the other hand, knowing the sort of hard times she’d fallen into, knowing that my money was probably going straight into a needle in her arm…… Fuck it.

“I can do that. What time?”

────────

I’d hit the atm on my way to her place. I was pretty nervous about the whole thing, and my conscience was already giving me some shit, but at the same time my cock was more than eager enough to make up for it.

Nancy opened the door almost immediately on my knocking. She was in her usual ripped up, punk rock attire. Fishnet stockings covering her shapely legs, thighs exposed by obviously self inflicted rips. Cut off blue Jean shorts that left nothing to the imagination. That same white tank top she’d teased me with in her pics earlier. She was a little skinnier than she used to be, maybe a little more sickly looking, but with all the tattoos (both arms, most of both legs, some on her chest and back) and piercings (multiple times both ears, nose, septum, labret, cheek implant) the sickly druggie look, honestly, was super hot.

She had a kind of mischievous, hungry look on her face. There was some dumb idle chatter as she led the way through the house. My eyes were boring into her ass like laser beams, the too-short shorts showing off plump, exposed cheeks.

When she stopped and turned to face me we were outside her bedroom. “So, we doing this?” she asked with a certain playfulness in her voice. I nodded and confirmed “yeah, I hit the ATM on the way over. We’re good to go.”

All light, all casual. I was on guard for something nefarious to happen…never trust a junkie and all that. But no, she was still enough my friend she’d meant what she said. She nodded, took my hand, and led me to her bed.

I sat first and she leaned down, immediately kissing me. Her hands went to the sides of my head and pulled me tight to her. I was sitting on the edge of the bed; I scooted back and pulled her down to me. She straddled me, one tattooed leg on either side of me as we kissed. My hands dug into the flesh of her back, rubbing up and down, slipping down into her jeans. She wasted no time in pulling the tank top off and tossing it to the side, freeing those big, beautiful tits.

Right now they were mashed on my chest between us as I groped her ass. She hadn’t been wearing any panties and I was feeling her bare ass cheeks. They were heavenly, soft and plump, filling my hands nicely. She was grinding her pussy up and down my throbbing hard cock as we kissed, her tongue darting aggressively out to tangle with mine.

She leaned back and moved my hands to her chest. She loooked down at me and grinned as I fondled her, tits spilling out of my hands. I moved all over touching every bit of her; the fullness of the edges, the soft underflesh, her stiffening, pink nipples. “They everything you dreamed they would be when you were jerking off thinking about me in High School?” she asked as she savored my touches.

“High School? I was jerking off thinking about you just the other day.” Not a lie, either, we’d seen each other at the grocery store and I’d jerked it raw wishing I could have fucked her right there in the produce aisle.

That seemed to please her. She scooted down and undid my pants. I saved her some trouble and slid them off all the way, my underwear joining them in a heap on the floor. She sat me on the edge of the bed again, hit her knees, and looked up at me as she opened her mouth and stuck out her tongue.

It made an amazing sight; her huge breasts, heaving and flushed. Her eyes twinkling. Her pink, wet tongue coming out of her mouth and running from the base of my cock to the tip. I groaned deep in my throat as she licked me like a lollipop, up and down, around the head over and over again, only to go back down and suck my balls into her mouth. She went slow, teasing, making sure I got my money’s worth.

As she came back to the tip I grabbed a handful of her hair and forced her down on it, sliding my cock into her mouth. She gave a slightly surprised “Mmf” noise as she opened her mouth to take it all in. Her mouth was hot and wet and amazing. I felt my cock hit the back of her throat and she started to gag on it. I held her down for a moment before I let her come back up for air. She got out an “oh fuck yeah” before I forced her back down on it, her tongue sticking out, drool running down her chin. It went that way for a minute, her gagging on me, me using handfuls of that long hair to force her down on me. Tears were running down her face. If she really needed air she’d slap my wet cock against one of her tits, or run it between them and stroke it up and down.

Eventually she had me scoot back and lay down lengthwise on the bed. She pulled the jean shorts off in one clean motion and straddled me again. My cock wasn’t in her, but it was nestled between her pussy lips. “You wanna fuck me now, right?”

I didn’t answer, but tried to squirm around so that my cock would slip inside her. She squeezed her legs together, pulling her pussy away. “Not yet. I want you to eat me out first. I hear tell Brit used to call you the pussy eating king.”

“Well lay down here and let me eat you out before you get fucked, then.” I said, looking down at where her slippery wet pussy was grinding my cock again.

“Lay down? No, it’s time for some payback.” she said as she scooted up my body. Before I knew what was happening I had one tattooed, stockinged leg on either side of my head and her pussy smothering my face. Look, I know she was probably more wet for the money I’d be giving her later, but in that moment her pussy was searing hot and sloppy wet.

I stuck my tongue out and just went to town. I wanted to live up to expectations. My hands firmly grasped her asscheeks as she ground her pussy into my face. She was definitely getting her payback, only grinding back far enough to let me breathe through my nose every once in awhile. Otherwise she kept me pinned there, my tongue buried in her, lapping at her juices. I don’t think she shaves really at all, so my world became hair and pussy and the heady stink of her juices all over my face.

As I massaged her ass I’d push her up a little, signalling to give me some air. A few times she actually listened. But with each squeeze I moved my hands a little more inward towards her crack. I dipped a hand low enough to get some of her juices on it and began to massage her tiny puckered hole while she rode my face. She had her hands against the wall for support, grunting as my tongue exploring her steaming hot cunt. When she felt my finger at her asshole she pushed back, giving me permission. I slowly worked in a finger, trying to match my finger to the rhythm of my mouth on her pussy. After just a few thrusts I felt her legs tense and an even louder groaning. My face got even wetter as her pussy gushed all over me, her ass contracting to trap my finger in her. I now REALLY couldn’t breathe, but just rolled with it, my tongue fucked deep inside her feeling the contractions of her orgasm.

She kind of just collapsed on the bed beside me, sprawled kind of sideways. I got on my knees and grabbed her ass, rolling her so she was fully on her belly. I gave it a good slap that echoed in the empty post-orgasmic silence of the room. She yelped and jumped, but didn’t say anything. I slapped the other and she pulled her knees under her, pushing her ass up into the air.

“Fuck me.”

I didn’t need more invitation than that. I grabbed her ass, lined up my cock, and slid right in. She was still tight from cumming so her pussy gripped me as I began to thrust against her. I started slow, but this wasn’t some slow and gentle lovemaking session and before I knew it was pounding the hell out of her, my balls coming up to slap her clit as I fucked her.

She started letting out a stream of dirty talk, broken up by little “ugh” noises as I fucked her. She told me to fuck her, to slap her ass, to pull her hair, make her my little bitch. I fucked her harder than I knew I had it in me.

She eventually turned her head so she could look at me over her shoulder, started commanding me to cum in her between thrusts. I could already feel it building in me, my balls tightening against my body. But it was her looking back, grunting out “fucking cream me, fill my slutty pussy up with that cum!” that finally did it. I buried myself balls deep in her, my cock spasming, jetting out spurt after spurt of cum. I felt it leak out around my cock on the bed. I held it there as long as I could but eventually plopped out. She turned face up on the bed, her body flushed, her pussy red and swollen from the pounding it had taken. My cum leaking out of her.

Suddenly she kind of lunged forward, grabbed my head, and forced it down between her legs. “I’m close to cumming again, eat me, now!” There was an urgency to her voice that was just hot. I dove in again, this time the smell of her pussy combined with my own cum. I licked and lapped at her, my tongue finding her clit as my fingers slid into her. Her pussy was hot and slimy from our fucking, her pussy clenching at my fingers with every thrust. I licked at her, fucking her with my fingers, over and over again. I could hear her breath heaving out of her, tits bouncing on her chest as she thrashed around on the bed. Her hands tangled in my hair, pulling me tight against her crotch. My face was shiny with our juices, my fingers going numb from slamming into her pussy. Her back arched off the bed, she went silent, and her pussy clamped down on my fingers. She was still for just a moment as she peaked, then all but slammed back on the bed as she came, gasping out and grinding down against my fingers and face as her orgasm washed over her.

We finally caught our breath. There was some akward chit chat. I didn’t drag it out; I got dressed, made sure she saw me put the cash on her night stand, and I hit the road. I didn’t even tell her about the extra 50 bucks I’d left for her, but I felt like she earned it.

Source: reddit.com/r/gonewildstories/comments/5i5x7b/my_friend_approached_me_about_prostituting_herself