I [28/M] just paid a stranger for oral sex [40s?/F].

I'm generally not one to write about stuff like this, but considering how utterly depraved it was I thought you guys might like it. This literally just happened in the last four hours, so I want to get it all out while it's fresh. I apologize if it's too long or needlessly detailed in certain parts, but it's just kind of an unedited brain dump.


I don't have a full-time job. I do a lot of contract work from home, often at anti-social hours. Whenever I want to take a break, I get in my car and drive to a nearby gas station for a snack, just to get out of the house. Tonight I threw on a dumpy sweatshirt and baseball cap before leaving. That, in addition to the fact that I'm a pretty big guy (6'5", 250 lbs.) with a tidy beard probably made me look a little intimidating. That (or at least my mindset around how I look) is important later.

I popped out shortly after 11pm and drove to a convenience store on the edge of my small town. It's a well-lit gas station near a highway, but aside from an occasional passing truck, there was almost no one out this evening.

I stepped inside to hear one of those door chimes, but the place was otherwise silent. There was no one at the counter, either. After getting a soda from the cooler and grabbing some gummy worms, I went to wait at the register. I heard a voice from the back:

"Coming!"

After a few moments, a frazzled-looking middle-aged woman walked out of the office area towards the counter. She was honestly pretty plain-looking, with no makeup and her longer brown hair in a hair tie. Her company polo was a size too small, but her modest boobs were obviously unencumbered by a bra.

When she got within a few feet of me, she looked in my direction and her glum expression evaporated into a kind smile. A millisecond later, her eyes met mine and she brightened even more. This really caught me somewhat off guard for two reasons: she had seemed extremely anxious only a moment ago, and (as was described earlier) I felt pretty self-conscious about my appearance; if I was working alone at a gas station, I probably wouldn't want a guy like myself to come in at 11:30 at night. I tried to brush it off.

"How are you this evening?" she asked as she rang up my junk food.

"I'm well. How about you?"

"Good," she said. "Just getting started for the night." She had this honeyed element to her speech that made it hard to look away from her. The words that came out of her mouth were chatty, but her speech was deliberate.

"Oh yeah? You work the night shift a lot?"

"Not as much as I'd like." This lady has barely broken eye contact at this point, and I can feel my breaths getting shallower. "I found out this week that my hours are getting cut next month." She was using her free hand to play with the collar of her shirt.

I fumbled with my wallet for a few moments, fishing out my credit card. I handed it to her, grazing the length of her fingertips as she pulled it away.

"That's too bad," I replied. She barely looked away as she swiped my Visa. Why was I so paralyzed by this encounter? I'm generally not a socially anxious person. Was she being more than friendly? There had been a thick pause since my last contribution to this hollow conversation, so I blurted the first thing that came to mind.

"Less that you count on?" I asked.

"Sort of," she sighed. "They're just working some new kids into the rotation. It's fine. I was a bad girl a few times this summer and showed up to a couple of shifts late, too. That may or may not have played a role in it." She handed my card back to me, widening her slight smile into a toothy grin.

Seriously, what the fuck was with this lady? I was dressed like a bum and my personality must have seemed wooden at best. But there was no way she was just being friendly, right?

She gently nudged my soda and candy towards me without looking down.

"Any big plans for tonight?" She asked it with a new, tiny hint of boredom.

I couldn't manage anything in reply. I was genuinely starting to feel short of breath, as if I was putting all of my concentration into meeting this woman's tired, curious eyes. It was like I was being crushed under this newfound anxiety that totally undermined my ability to compute basic functions. With the last scrap of air in my lungs, I gave into my impulse and just:

"Wanna make fifty bucks?" My lungs were empty, and the cold night's air was suddenly much more noticeable on my skin. Was I shaking? If I was, I couldn't tell. I didn't want to release my eyes from hers. How long ago did I say that? Her eyes narrowed, then widened, and…

she laughed.

Deep breath. I leaned onto the counter, for balance more than anything.

"What does that mean?" she cooed. "Do you want me to do a party trick?"

"If that's what you want to call it." Breathe in, breathe out.

Her wide smile faded, but her mouth never quite closed. For the first time that evening, she took a lengthy glance at the floor before looking back at me.

"What do you want me to do?"

There was no way I could look away from her at this point. I was breathing again, but my face was red hot. It felt as though I was holding the roof up with my bare hands.

"Be a bad girl."

Her smile was gone, but she wasn't looking away.

"Are you serious?"

"Yes."

She wasn't smiling anymore. Her gaze lingered on my face, then my chest, then my face, then turned to study the security monitor. She faced me again and studied my expression, as if she was expecting me to break the act. I looked over my shoulder to confirm what she had no doubt seen on the cameras: we were alone.

Before I could turn around, she had hopped down from the raised island counter and made her way halfway to the room she had appeared from. She reached the door, barely glancing over her shoulder.

"Hurry up." She didn't break stride.

I turned myself mechanically… left foot, right foot… and briskly walked to the end of the store. I peered into the doorway; she was dusting off the swivel chair in what was more of a closet than a manager's office, with plastic binders littering the floor, an old desk and the same TV monitors she had been watching earlier. She turned to me as I approached.

"Money."

I paused briefly before pulling out my wallet, handing her a $20, a $20 and a particularly gross looking $10. She pocketed them and closed the door.

"Pull your pants down and sit."

Holy shit.

I did as she instructed without hesitation, releasing my rock-hard self into the stale air. The faux leather felt cool on my ass, but it was already hot in there with the door closed. She placed her hand on my knee for balance as she lowered herself in front of me, taking my cock into her other hand and holding it as gently as anyone ever has. She smiled for the first time since we were at the counter, but it was more nervous than flirtatious.

"I'm going to suck you off. Watch the cameras. If anyone shows up, we're done."

I knew this was my last chance to set conditions, so I barely waited for her to finish speaking.

"Take your shirt off."

She hesitated, giving my cock two slow strokes. A moment later, she scooped her undersized shirt over her head in one quick motion.The untoned but fairly slim body in front of me was exactly what I expected, slightly saggy mom stomach and all. Her small, cute tits sported pretty big, pink areolas, but her nipples were tiny.

She took a sip from an open water bottle on the desk, licked her lips, and made eye contact with me for what would be the final time that night.

"This never happened."

With that, she plunged onto me as though she were adding words to a run-on sentence, connecting the tip of my 7" dick to the back of her throat with a slight gag.

She briskly drew her lips up and down the length of my shaft,

once,

twice,

five times,

leaving it wetter and wetter with each pass.

Every few moments, she'd take me as deep as she could, grazing me with her nose and playfully wagging the tip of her tongue along my balls.

I straightened up in the chair, reaching down to cup both of her tits in my large hands, gently toying with her hard nipples in rhythm with each stroke she made.

"Mmm… mmm…"

She started to moan with every other pass, sliding her free hand from my leg to underneath my shirt, pawing at my chest hair. She bobbed at a moderate pace, gently manipulating my balls, until finally coming up for breath with a sharp gasp.

She pumped my cock with a faster pace, using her breather to roughly kiss and lick my balls. I tried to make eye contact with her again, but hers were firmly shut as she hungerly tongued me below my cock.

I moved my big palms from her soft tits to her shoulders, and she took it as her cue to plunge down onto me again.

Up, down. Up, down.

She repositioned herself to continue rhythmically stroking my balls with her left hand, her right holding the base of my dick.

Slurp, slurp. Slurp, slurp.

It couldn't have been more than two minutes since she shut the door, but I could already feel it.

Up, down. Up, down.

"Hey…"

"Mmm?"

"Don't stop."

She hastened her pace and tightened her lips. Each pass was wetter and harder than the last, her hand rougher and rougher on my tightening ballsack.

Schlick, schlick. Schlick, schlick.

"I'm going to cum."

"Mmmmmm."

"I'm going to cum in your mouth."

"Mmm-hmm." An invitation.

I shot. I shot harder than I have in months.

One rope. Two.

Her pace slowed, but her intensity didn't.

Three. Four. Five.

"Augh, fuck!" I couldn't help myself.

Six. Seven. She slowed to a calmer pace, still pulling.

Eight. Less intense now.

"Shit," I sighed.

Nine. Jesus. She slowed to a crawl, cum finally leaking out of her mouth. She gulped twice, but it didn't help. Her eyes were open now, but she didn't look at me.

My jizz dribbling down her chin, she popped up, wadded a paper towel and spit into it twice. She tore off a new one and dropped it in my lap.

"Hurry up."

In one motion, she picked up her shirt and swooped it over her head. Inside out. She took it off and fiddled with it while facing away from me before putting it on again. She took another swig of water, staring into the corner as I wiped myself off and pulled my pants up to my waist.

It was really hot in there.

She opened the door and stepped out.

"You need to go."

I walked to the counter, feeling less comfortable than I had a few moments before. I grabbed my stuff and walked to the door in silence. The door opened with the familiar bell, but I heard her over my shoulder as I walked out.

"Thank you!"

I jumped in my car and went straight home, but it's safe to say I didn't get any more work done tonight.


So, that's it. I asked this woman if I could pay her for sex under a super shaky pretense of probable but unproven sexual tension. I don't know why. I don't know why I offered to pay her, either.

I've had spontaneous sexual encounters before, but this is easily the best story so far, honestly. My head is still swimming, so I might add to this later after I sleep.

Also, I ate the gummy worms.

Source: reddit.com/r/gonewildstories/comments/3wx49l/i_28m_just_paid_a_stranger_for_oral_sex_40sf

13 comments

  1. This was a really great story to read. Hilarious simile about run-on sentences too! Edit: also, did you notice a wedding ring on her, by chance?

  2. If she hadn’t said anything on my way out, I don’t know if I would have. But I feel like I should, right? The smart thing to do would probably be to go back next week, but I might get impulsive tonight.

  3. I am 100% sure she wasn’t wearing any jewelry in the office, though I honestly don’t remember if she was before that and took it off. Would she wear something like that to that job anyway, though?

  4. On the one hand, you should play it smart and wait. On the other hand, she might be hoping you come back again tonight. My money’s on option A. But then again, I’m a faceless stranger on the Internet. I don’t even know if we’re in the same country.

  5. I wear my ring all day, so does my wife. Don’t see any reason why she wouldn’t for a retail job. Hot story man. If you do end up going back and meeting her again, make sure you tell us!

  6. I don’t know… Depends on whether she part intended to get up to any mischief. Most people just leave their wedding ring on all the time, don’t they?

  7. If it was, I would choose not to include that information for fear that people would read this and think the entire post was an elaborate setup for a silly joke.

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