Greetings! This is a true story which got me banned from GoneWildStories as I was not explicit about the ages of those involved. I hope you all enjoy it. Additionally, I anticipate that you all will be able to surmise that everyone was over 18 as suggested by the facts that the involved parties were a senior in college and a graduate student, respectively, but just to be absolutely clear: we were both in our 20s.
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[Edit for tags and clarity] M/F, I was 26 at the time, she was 22, no cheating for the butthurt, everyone tested for STIs and birth control used for the health-minded, alcohol consumed for the abstainers…what else…Easter mentioned for the anti-religion/Jeebus crowd…higher education mentioned which may offend the dummies…okay I think that’s it. You’ve been warned. Proceed with caution. Lots of preamble. Skip to XXXXXX if so inclined.
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My parents split up when I was in junior high and my dad remarried when I was a senior in college. Since we lived in a small town and she used to be a teacher at my high school, I had known (or rather, known about) his new wife for years before they started dating. By the time I was in high school, she had taken a job at a different school outside of town, so she was never actually my teacher but I had always heard about how cool she was. She was one of the rare high school teachers that actually liked kids and took pride in her job. You probably (I hope) had a teacher like her yourself in school. Nearly all of her previous students loved her and many of them stayed in touch with her after graduation.
Okay so fast forward a few years after my dad remarries the cool high school teacher. Now I’m in my last year of grad school. My college is about 3 hours away from my home town, which is the perfect distance as it’s not so close that my dad and his wife can just show up and surprise me, but it is close enough that they can easily come over for the day, or I can go home for the weekend if I have the time.
I’m close with my dad and very much a chip off the old block, which is to say that we are both inveterate horn dogs. Also, we both have traditionally been able to punch well above our respective weight classes when it comes to women. He was a nice, smart, funny guy but certainly not traditionally attractive in his 50s — a silver fox he was not. But after my parents divorce, he pulled an inordinate amount of ass that was way out of his league. He would regularly date semi-attractive 20-somethings and objectively hot cougars over the course of a few years before he met his eventual (age-appropriate) wife. Probably had something to do with having a cool job and decent cash.
I’m no male model myself but I’ve had similarly mystifying luck with hot women. Humble brag, I know, but it’s been puzzling to both me and my friends over the years how a 5 like me keeps on landing 9s. Maybe it’s genetic? But I digress.
So even though he settled down and was happily married with his new wife, my old man was still a dirty old man. As he aged, his taste in women aged as well. What the two of us considered attractive diverged considerably as expected, and his taste turned more to older women with huge asses. Not that there’s anything wrong with that, but it just wasn’t my bag. You know the brassy broad that works at the local cafe? Or the lone female law enforcement officer in the county? The old battle axe at the grocery store checkout line? That’s the sort of girl that’d really get him fired up.
You will understand why I had some reservations about his opinion when he started telling me about how hot his new cleaning lady was. I had a rich friend growing up, and I remembered his old cleaning ladies from when I was a kid. These were not hot women. More two-bad-weeks-away-from-hooking-for-meth type women. So I just ignored his hornball rants about how he loved to watch her bend over and pick stuff up while she worked, chalking his attraction up to the fact that he had now settled down but still had a wandering eye.
My last year of grad school was not particularly busy and as such I was able to drive home for visits on the weekend. I came back for Easter that spring and noticed an extra place-sitting at the table for the big family meal on Sunday. I was informed (with a sly grin from my dad’s wife) that the cleaning lady Jenny would be coming over . Thinking this was odd given my mental image of her, I asked some more about her background.
Turns out she was one of my step-mother’s old students that had kept in touch. She was a junior at the local college majoring in art and dance. She had a website that my stepmom showed — all very cool mixed media stuff. She came out and cleaned around the house once a week to earn some extra cash, but mostly just to shoot the shit with my step-mom. My interest was piqued — if nothing else, she would be good for a change of pace in terms of conversation over the usual boring family dinner.
It was a holiday so day drinking was not only acceptable but actually expected at my house. I’d had a couple of Bloody Maries by the time the guests and distant relatives started showing up. It was a good time — we were all well-lubricated and I hadn’t seen anyone in a long time, so it was fun catching up with the usual crowd of cousins and family friends.
Then in walks Jenny, and I’ll be damned if my dad wasn’t spot on. She did have a nice ass. Strike that — an amazing ass. My step mom had told me she was a dance major, but I could have figured that out as she walked in from the car. She was short — maybe 5’1″ — and slender with what appeared to be a small chest. She was dressed nicely for the occasion — tighter silk shirt with an open collar and dress pants. They fit loosely but I could clearly still make out a bubble butt bouncing along as she walked into the kitchen. And she moved gracefully, up on her toes. She had an adorable face — pixie cut brunette hair, bright brown eyes, a wide smile with big thick lips and rosy cheeks. She was the spitting image of an early 2000s porn star called Aidan Layne, with a body like Mia Malkova. (And give me a break on the references. I was single and painfully horny. PornMD was my friend.)
Dad was right. His cleaning lady was fucking hot. But, whatever, it’s Easter and I’m just home for 8 more hours. I keep my steady buzz going and decide to get to know her a little better.
As the only people under the age of 30 at the house, we paired up immediately and really clicked. I was getting a biology degree and so our areas of study were widely different, but we were mutually interested enough to talk a bit about our classes. We had a lot of similar tastes in movies and music and had enough mutual acquaintances (many of my high school friends had hung around my home town and she knew a few) so the conversation never lulled.
After lunch I was fat, happy, and drunk. It was only 3 or so in the afternoon but everyone felt like taking a nap. The guests who lived in town said their goodbyes and took leave while the rest of us tried to find some flat surfaces to snooze on. Jenny hung around, ostensibly to help my step-mom with the dishes, but once everything was cleaned up and my dad and his wife had gone to crash in their room, she made her way into the living room where I was talking with my brother.
My brother could sense something was up and politely excused himself to go take a nap upstairs. This left Jenny and I alone in the living room. We kept on chatting away, getting more flirty as the afternoon wore on. At some point it came up that we were both single. We didn’t linger on it, but the stage was definitely set to get closer.
After an hour or so, I started to feel legitimately tired. I yawned a few times, causing Jenny to do so as well, and she suggested we take a nap. I’m 6’3″ and the single couch in the living room on which we were sitting was too short for me, so I grabbed some pillows and got down on the floor next to the couch. Jenny laid out on the couch herself, having plenty of room as she was a full foot shorter than me.
We laid next to each other and her hand dangled over the edge of the couch. Still chatting away, I admired the ring she wore (she had made it herself) and used it as a pretense to touch her hand. Fiddling with the ring lead to lightly tracing circles on her fingers and palm. She giggled as I lightly tickled her and I began to massage her hand.
It was bizarrely intimate. We had just met only hours before, my entire extended family was sleeping off a day buzz in the rooms around us, and the sun was shining brightly through the windows on a perfect spring day. This sort of canoodling is the kind of thing I’d done before, but always with girls I’d known well, and always in the wee hours of the morning in shithole apartments.
As I continued to massage her hand, our conversation dropped off. A good hand massage is on par with a good foot massage, and I’m the hand fuckin’ masta’. She was letting out soft sighs and eventually rolled over on her stomach to get me access to her other hand. She smiled down at me. I started tickling and massaging her right hand but the angle was awkward and after a few minutes she silently got down off the couch and stretched out next to me on the carpet.
Her breathing grew shallow and short as we laid on our sides, looking into each others’ eyes and smiling. I held her hands one at a time, and she would use her other hand to massage my arms and chest. Our faces were right next to each other, so close that I could feel the warmth of her breath, our lips just barely grazing. Periodically the weirdness of the whole situation would strike one of us and we’d start giggling like kids, but then we’d get right back into the slap-and-tickle.
This went on for what seemed like hours. I’m sure it wasn’t. It was just one of those magic moments that gets burnt into your retina. This girl that I had just met that morning girl was straight-up hot and I was now on the floor of my step-mother’s house fooling around with her. It felt amazing. I, of course, had a dick hard enough to do, like, 2 cock push-ups with.
The kissy-face couldn’t last forever. Eventually we heard my dad rustling around and we jumped up like a couple of nervous teenagers. Jenny and I exchanged numbers and made plans to get together sometime. I walked her out to her car and held her face in my hands, just barely touching our lips for a few seconds before pulling away.
(Side note that you’ll want to skip if you get butthurt or turned off by childish humor: as I walked back into the house with two massive, swinging blue balls and a dick so hard it hurt, I ripped a fart like a brontosaurus. Seriously, it took me probably 50 steps to get back inside and every single step was punctuated by an asshole-stinging bark of a fart, while in between each step I was constantly letting out this low-level fog horn fart. It was amazing, but also totally par for the course. Anyone else fart like a motherfucker when they’ve got blue balls?)
Back to the main event: you’re goddamn right I found a reason to come home the next weekend. I did Friday dinner with my dad, after which I went downtown to meet up with Jenny for a drink. We didn’t even finish our cocktails before we found an excuse to leave her friends at the bar. We went back to her place — she lived in a typical college town dump of an apartment. We drove separately and she met me at my car as I was getting out.
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She jumped up on me, wrapping her arms and legs around my neck and hips. She couldn’t have weighed much more than 100 pounds. No more teasing now — foreplay was over. She attacked my mouth with hers, snaking her tongue against mine. “Take me inside and fuck me,” she whispered in my ear.
I dropped her to her feet and we giddily raced up the stairs to her place. I of course let her lead, as (1) I didn’t have any clue where we were going and (2) it afforded me the opportunity to admire and paw at her ass as she ran in front of me.
We got in the door and stripped as fast as possible as we made our way back to her bedroom. She lived alone so no need to worry about roommates. We were both completely naked by the time we got to her room. She took my hand for the last few steps and I got to admire that amazing little bubble butt bounce while she walked me to the end of her bed.
She sat down and took my shaft in her hand. I’m no porn star but because of her petite size, her hands were so small that she could barely get them around me. Her height also ensured that her head was at the perfect level to gobble my cock as she sat on the bed. She used her other hand to fondle my balls for a second, looking up at me with those dark brown eyes and squeezing my shaft a few times.
Then she pulled a game changer: she spit on my cock. I’d never had a girl do that before. It made the whole experience feel even more surreal. With the added lubrication from her saliva, she started to slowly jack me off, still looking up at me with those sleepy brown eyes. Just as I was getting into the rhythm of it, my eyes rolling back into my head, she spit on me one more time, picked up the pace for thee fast, full, head-to-balls strokes, then DEVOURED my cock.
It. Was. Fucking. Amazing. Since high school, I’ve never been able to come from a blowjob, but I knew within a few seconds this girl was going to have me erupting if I didn’t do something. She was fondling my balls and taking as much of me down her throat as she could. It was a truly sloppy, enthusiastic hummer — she knew what she was doing and really enjoyed it herself. It felt so fucking good as she bobbed up and down on my cock that I honestly had a sort of out of body experience, which helped me from blowing a load down her throat. I got the sense that she would’ve been cool with a face fucking, but I’ve never been into that. So I reached down and stroked her cheek while my knob bobbed into it.
She dropped her hand from my shaft and kept going with the light ball fondling. She kept bobbing her head up and down my cock and used her other hand to rub her clit. This was beyond hot — knowing that getting me off was getting her off, too — and at that point I HAD to stop or I’d explode.
So I gently pushed her shoulders back and she lay flat on her back. I knelt down between her legs and breathed in deeply. Her cunt smelled amazing and she had clearly gotten waxed recently. It was a shiny, completely bald simp (thanks for that term, Reddit), and to this day I feel like her pussy must have been genetically engineered to look so perfect.
She was soaking wet, dripping grool as she writhed on the bed. I gave her light kisses on the inside of both thighs, working my way up to that Holy Grail of a vag. I can tell myself that I took my time and was all cool and withholding about it, but the truth is I dove right in. I could not wait. She tasted just as good as she looked and smelled, and I went to town on her pussy with my tongue. I eased a couple of fingers into her and worked her into a frenzy as I rapidly lapped away at her clit, sliding my fingers into her at a slower pace.
After a few minutes of this I hit whatever magical, voodoo rhythm it was that she needed to get off. I heard her breathing change, took a big breath myself so I could have enough in me to get her over the edge without pausing, and went back at it. Within several seconds she was screaming my name, which devolved into guttural moans as she rode out her shaking orgasm.
I withdrew my fingers and gave her pussy lips one last, long lap. This sent another shiver through her but she had come down from her peak and smiled down at me. She pulled me up onto the bed, gesturing for me to lay down. Kneeling between my knees, she spit on my cock again and jacked me off a few times. This got me back up to full mast.
Still looking into my eyes, she shuffled forward, got up on her feet, and squatted down over my cock. She took the base in her hands, angling upward, and slowly impaled herself on me. She was tight but still dripping wet so it was one long, slow, grunt-inducing trip down to my balls. I completely bottomed out in her gorgeous cunt and she just sat there for a few seconds, smiling down at me.
I reached up to play with her little tits. She wasn’t completely flat, but she was close. AA cups maybe? She had adorable little nipples that were almost the same color as her skin (ghost nipples — again, thanks be to porn subreddits for broadening my vocabulary) and I lightly pinched and caressed them. This seemed to set her off and she started to raise and lower herself on my cock.
It felt amazing. That pristine, bald, slick cunt sliding up and down on my dick was mesmerizing. She was gorgeous with a fantastic body but for those first few minutes all I could do was stare as my cock stretched her lips, her little pink clit poking out from the hood on her upstroke. I moved my hands from her tits to the bottom of her thighs — slender but strong — and helped her petite body ride me.
It felt good for her, too. She was soaking wet to begin with but she got wetter as we fucked. She reached a hand out to grab one of my, guiding me to pinch her nipple. With her other hand she reached down and started rubbing circles on her clit.
“Harder,” she said as I twisted and tickled her nipple. She was picking up the pace and her breathing was speeding up as well. As great as this position was to watch, my dick was hitting her at an odd angle for me and I knew it wasn’t going to do it for me, which was great because she clearly was going to come. She stopped the bouncing routine and got on her knees with me still inside her, still squeezing my hand against her breast and rubbing her clit, but now also bucking against my pelvis in short, fast strokes. This brought her over the edge and she started moaning and saying my name again. She didn’t squirt like a fire hose or anything, but I felt a distinct gush of warmth on my cock when she came.
But she wasn’t done, and thankfully I somehow was able to keep from blowing my load. She slid off me, turned around, and knelt down on her knees between my legs. Now I had another view of that perfect ass, this time all slick with sweat. It was a colder spring and she was a broke college student so the apartment was a little chilly. I hadn’t noticed it before, what with the mind-blowing fuckery that had been going on, but I felt it with this momentary pause. She felt it, too, because that perfect little ass of hers was suddenly covered in goose bumps.
Not for long, though. She shuffled to the end of the bed and pulled me down there, too, so my legs were hanging off. She stood in front of me, facing away, and reached back to grab my cock and sit on it. She was still soaking wet and newly stretched out so this time I went right inside. I had more control in this position and used it to grab her hips and bounce her up and down on my cock. I sat on the edge of the bed, using the springiness of the mattress to thrust up into her while pulling her body down on me. It felt great to me but after a minute or two like this, I hit her at an angle that made her yelp. She took my hands off her hips and guided them to her nipples, and I resumed pinching and twisting them like before. She had been supporting herself with one hand in either one of my thighs but now she took her left hand and started furiously circling her clit again. Within 20 shallower pumps at her pace, she started shaking and came again, this time with a much quieter orgasm but one that she rode and rode and rode for at least a minute.
“Goddamn,” she said, looking over her shoulder as we kissed. She stood up, withdrawing my cock in the process, and turned around. She was wobbly on her legs and fell into me. We giggled and kissed some more as we fell back onto the bed, our legs and arms intertwined. We complemented each other’s bodies and talked about how amazing this felt for both of us. She was a little embarrassed about the gush from before but I told her it felt incredible.
She looked down at my dick and realized I was still hard. “I want you to come now, inside me,” she said, crawling up on her hands and knees. She looked over her shoulder at me. We had talked about birth control and STIs earlier in the night. She told me that she had gotten tested last month and had an IUD placed at that time. She hadn’t taken it for a spin yet, as I was the first guy she’d slept with after getting it placed. I myself had gotten the all-clear from my student health clinic the week prior, so we both had no qualms about barebacking from the get-go. And now she was wanting me to finish inside that exquisite cunt.
She didn’t have to tell me twice. I stood at the edge of the bed (again, perfect height) and she shuffled back to me. Her squeaky clean little pussy had me hypnotized. I grabbed her hip with my left hand and used my right to line up with her slit. I teased her with my head, stroked up and down her lips and clit a few times before easing myself into her and bottoming out. Grabbing both hips, I jumped right in at full speed. This was an animal, viscous pounding. She let out little squeaks with each thrust and I just marveled at the sight of this perfectly round little ass in my hands. I spread her cheeks and watched my cock glide in and out of her, covered in her wetness, her asshole glistening above it.
It was too much. I started to slow down, hoping to prolong it, but there was no stopping. She mistook my change in pace for me wanting to stop. “No, don’t pull out, I want you to come in me,” she said, and started rocking back and forth onto my dick.
I let out a roar and erupted inside her. Rope after rope of jizz fired into perfect pussy, just blasting away and filling her up. She kept rocking on me and I just kept emptying my balls into her cunt. Spunk started to slide out along the sides of my cock as she kept rocking and I softened a bit.
She crawled forward in the bed and starfished out, my semen now actively running out of her into a puddle on the bed. I crawled up next to her and we laughed and kissed, talking for hours before we got all horny and fucked again. And again when she woke me up with a blowie in the morning, followed by standing doggy style in the shower.
We kept up a long distance relationship for a while until I graduated and moved too far away for it to be feasible. She’ll always be top 10 in my spank bank.
Source: reddit.com/r/Erotica/comments/4bkjga/tryst_with_the_cleaning_lady_mf
Goddamn