My submission for the November 2020 contest.
TL;DR, if you read [this story](https://www.reddit.com/r/gonewildstories/comments/ixw8ue/mfmf_wedding_reception_swap/), you heard about Anna’s and my first time swapping with another couple. But it wasn’t *my* first time swapping. I only shared the details of my first swap with Anna after our time at the wedding with Sarah and Dan, and I eventually came clean about my numerous exploits when I was in college and thereafter. To my surprise, Anna was into all of it, and wanted to explore further (those stories for another time). What happened here took place when I was 23 years old, so a *very* long time ago, and in college, when my girlfriend Lee (not her real name) swapped with a couple named Doug and Jeannie (not their real names) after a work holiday party.
Lee was the first girlfriend I had who pushed the envelope sexually. I wrote before about Tami (not her real name) and a car chase, but my relationship with Lee was something different. Lee pushed all of the boundaries sexually, and our relationship, while toxic like eating paint chips, definitely cemented my interest in being open to new sexual experiences, no longer feeling guilty about being a sexually charged individual who grew up in a conservative and Christian household, and even through the most trying of circumstances — solidified what I liked, and what I didn’t like, sexually.
Over the course of 2.5 years with Lee, I experienced the following:
* Lee once wore a bikini so scandalous to a swimming pool at a state park that we were asked to leave. We then fucked in my car while people stood by and watched.
* Lee gave me a hand job, to completion, in a whirlpool at a hotel, and moments before two people joined us (platonically) in the whirlpool, my cum swirled on the surface of the hot water.
* On our first date, Lee told me that she could make herself cum without touching herself. She did this during a dinner out, simply by rubbing her thighs together underneath the table.
* Lee only kind of enjoyed vaginal sex, so she taught me how to go down on her and make her cum, and she loved anal. Vaginal was a special treat for me. She was so tight, hot, and wet that it would literally milk the cum out of me every time.
* Lee blew me in her parents’ family room as her father went to and fro right outside of the sliding glass door on his riding lawnmower. Her mother was working in the kitchen about 20′ away.
* Lee would sleep with other people, and by people I mean that it would be both men and women, where I was not involved. I hated this, actually, but our sex outside of that was exciting and made me weak in the knees always. No, I’m not a cuckold, not that it matters anyway. Like I said, this was a formative relationship for me.
* Lee and I would have threesomes with men that we’d meet when we were out.
* Lee would blow me in the middle of the parking lot of our very busy university. People would stand outside the car and watch, and having an audience excited both of us.
* We would stay at the university late at night and I’d eat her out in a stall of the ladies’ room while I jerked off and came on the floor.
* Lee talked me into fucking her (female) roommate, and laid naked on the bed next to us and masturbated, Lee cumming multiple times.
* She once picked up a woman from a nightclub, and I sat blindfolded in a chair, naked, as they had sex, the room smelled like pure sex, and by the time she let me out of the chair, the hardwood flooring had pools of their cum everywhere.
* The list goes on and on, really, but we did a full swap with another couple during the Christmas holidays of 1994.
Suffice it to say that I was into all of this at the time. Otherwise I wouldn’t have done it. Granted, I was reluctant to step this far out of my comfort zone, but as I look back, I realize how hot this all was.
Now to the matter at hand. Doug invited Lee (and by extension of that, me) to a holiday party at the university, but it was being held offsite at a banquet facility. Rumors had circulated for a long time that (1) Doug and Jeannie were swingers and (2) Lee would join them sometimes. I didn’t really bring it up with her, but I admit that I was really curious if she was playing around with them. After all, they had 15 years, at least, on the both of us.
Back then I didn’t know what swinging was. I thought that it was a key party or wife swapping, like some throwback from the 1970s, my friends and I would joke. Little did I know that it was a lifestyle choice, and no, I did not fancy myself a swinger then (and still don’t). I just found myself willing to roll with having to deal with Doug and Jeannie at a holiday party, and if all went well, Lee and I would have vaginal sex that night. Once Lee got 2-3 drinks in her, in particular when she was dressed in a sexy way, I could not wait to unwrap that package when we got back to her place (I had a place, too, but it was a hovel). Drinking a little bit always made her super horny, and for the most part I was the benefactor of her “affections” after she’d had a few.
We got changed in separate rooms, due to Lee’s thinking that things would go faster that way. By the time I had my suit all buttoned up, she was standing hear the door in her winter coat, and her dark stockings and dark, sexy stiletto heels gave me a hint that she was ready for action. I almost burst out of my pants at that moment, and try as I might, I tried to start undressing her so that I could take her to her bedroom. She told me not to smear her makeup or ruin the curling job she did on her hair, and basically shoved me out the door.
The holiday party went as anticipated for the most part. There was an open bar, rounds of food at the linen-covered tables, and Doug and Jeannie were tolerable for a change. Doug was actually kind of funny with his slight buzz, and Jeannie was slightly suggestive and mildly crass, but I admit that because they were basically unlike they normally were at work, seeing this new side to them was intriguing.
Lee was wearing this skin tight green dress, in her estimation because it was “festive”. It was definitely not work appropriate, and I could see and feel the eyes on her. Lee, between the way she manipulated men, her sexual adventurousness, and her tight and athletic body, definitely caught the attention of others. Half way through our meal, and we were holding hands underneath the table, she placed my hand on her nylon’ed thigh, and she guided my hand up to her crotch. She did so very discreetly, and while I know that I was beet red at the time, my hands quickly found their way to her garters, and I could feel the heat around her bare pussy. Lee, you see, eradicated all of her pubic hair at some point, and she wasn’t wearing any panties. She whispered to me that I should check the pocket of my suit jacket. Sure enough, her soaked and crumpled thong (I could tell that it was either a thong or g-string since it was so very silky and small) had made its way into the pocket of my suit jacket at some point during the evening. While laughing at one of Doug’s jokes, my hand came up to my face and I could smell Lee’s musk on my fingers.
Finally the evening came around to dancing, and by that point most of the crowd had disappeared. I guess that they had to go home to their families or something. So maybe a couple dozen people remained, and I knew not a single one of them. That was a good thing, because I knew that something was up, and I didn’t want anyone to know that we might be crossing some lines that night.
Jeannie and Lee danced for most of the evening, and Jeanne was rocking this knee-length red dress with thin shoulder straps, and her massive chest was straining to rip through the material. Her legs were bare, and her heels with ankle straps drew my attention, as did the sheen of her sexy legs as she and Lee bumped their asses as they danced to Electric Slide and a bunch of disco tunes from the 1970s.
Finally the DJ announced last call, and Lee and I went to get our coats. I couldn’t wait to get her home. This entire evening was the perfect setup for hours and hours of fucking. Usually Lee was pretty quiet in bed, except for when she came, but if she was a little bit buzzed and turned on, she was vocal, dirty talking to the max, wanted her hair pulled, wanted me to eat her pussy and ass, and yes, she would demand that I cum in her pussy. I was so excited about how the night was unfolding.
But then it happened. “Hey, uh, Doug and Jeannie invited us back to their place for a drink,” Lee said. She could tell the disappointment on my face, so she continued, “it’s just one drink, no big deal. You had a great time tonight, right?”
It was at that moment that I knew I would end up fucking Jeannie, and that Doug would have his way with Lee. I didn’t know how it was going to play out, but I admit that I was curious. *Very* curious. I’ve met a bunch of people who identify as swingers over the years, and their mantra is that swinging involves communication. I think that’s right. However, Lee and I were both 23, and we were super dumb, and from my end of things I wanted to *feel* it, so I didn’t protest about what was bound to take place. I was apprehensive and a bit reluctant because Doug would end up fucking Lee. But then again, I was probably going to fuck Jeannie. My god, I was a mess.
Doug and Jeannie lived in a split ranch outside of the city. A bottle of wine was cracked open, the stereo was cranked up in volume, and next thing you know, Jeannie takes my hand and drags me downstairs as “Just the Two of Us” (Bill Withers / Grover Washington, Jr) was blaring over the speakers. To this day the irony of this is not lost on me.
Jeannie gave me the “nickel tour” of their downstairs area, including a master bedroom, a full bathroom, a game room with a pool table, and a wet bar. My heart was pounding through my chest. Should I make a move? Should I wait for her to make a move? Was Doug going to roll up on Lee? Would she initiate? Was I supposed to do anything at all? I mean, something was going to happen, but I was trying not to puke my guts out, and if came to being with Jeannie I was just hoping that I could keep it up. This was all new territory for me.
Jeannie sat me down on one of their barstools, and she sat down in the stool next to me. She swiveled her chair back and forth and kept crossing and uncrossing her legs. We made small talk and she laughed a lot. Thing is? I don’t think that I was being that funny. Then she asked me if I smoked. Cigs? No. Cigars? Sometimes. But she was talking about 420, and at that time 420 was massively illegal, and even a couple of my mostly law-abiding friends got arrested for possession or for having been caught smoking. I wasn’t sure what to do, but Jeannie lit up a joint, and while I really didn’t enjoy pot that much, I took a couple of hits. That’s when 4 glasses of wine and pot co-mingled in my system, and I just felt… numb. Yes, I was still semi hard, and I suppose that being even semi hard was a relief given how nervous I was, but at least I wasn’t totally incapacitated.
Milli Vanilla was blasting on the stereo upstairs (I shit you not), and Jeannie got off her barstool and started to dance to a song that didn’t resemble “Girl you Know it’s True” whatsoever. She leaned over the couch and shook her ass at me. She raised her dress and gave me a quick flash of her sheer panties. Then she approached my barstool and thrust the front of her between my legs. She reached down and gave me a gentle peck on my lips. Then she turned her back to me, raising her voice slightly, and played with the zipper of her dress very noticeably.
“Do you know what this is?” she asked, quite bluntly.
“It’s a zipper,” I replied, probably too loudly, like a moron.
“So you know what to do, right?” she emoted, turning her neck at an unnatural angle, making eye contact with me as she glared over her shoulder. I took hold of the zipper and started edging it downwards. She pulled away from me, standing about 5 feet away, facing me, and she finished unzipping her dress. Then she took a few more steps backwards, dropped the dress to the floor, stepped out of the garment that was just pooled at her feet, and stood pretty close to me, maybe 2 or 3 feet away.
Jeannie was wearing this sheer bra and pantie set, and her heels were delectable. As she presented herself to me, strutting and shaking her hips to the recently mentioned non-existent song, I got a glimpse of her essence. A big, big glimpse. Her breasts were huge and were protruding over the top of this “cup-less” bra. It didn’t occur to me then, but obviously they’d been done. You could make out faint scars as she unclasped her bra and flicked it so that it landed on the top of their bar. Her nipples, whatever it was of them, were sticking straight out. He walked towards me and started stepping out of her sheer panties. She held on tightly to my wrist as she stripped off the remainder of her sheer panties as they were stuck to the ankle strap of her left heel. She bunched up her discarded panties and flicked them across the room, landing into the almost center of the pool table.
Then she motioned for me to give her my hand, and she dragged me to the master bedroom.
She asked me to unclasp the straps on her heels and she held my hand as she stepped out of them. Honestly, to this day, I love having sex with a woman who’s wearing heels in bed, so I was disappointed. But Jeannie pointed out that she was going to ride me — hard — and that heels on a waterbed is a no-no. Fair enough.
So she stripped me, kissing down my body, my nipples in particular (which Lee through her persistence showed me that I love as a pleasure point), and she started giving me amazing head. The door to the master bedroom was closed and we could make out some thumps upstairs. I wasn’t sure if it was the music, or if it was Doug pounding Lee. I wondered if it was both. Jeannie asked if I like to cum a lot, and I said that I did, and could. She said that I could cum as much as I wanted, and that she always thought that I was cute, and told me that she was hoping that we could have a great night together. Then she floored me when she asked if I thought that she was pretty.
I told her that I thought she was very pretty and that knowing we were going to spend the night together was very exciting to me. Sure, Jeannie had 3 kids, and had a tiny bit of a belly, the fake boobs were a sight to behold, and so on, but she knew what she was doing, and I could not wait for what she had in store for me, for us.
So, as she blew me, Jeannie pulled my ass cheeks apart, and her hand motions intimated that she was going to penetrate my asshole. At that time I wasn’t into it. I just hadn’t evolved into an understanding that I’m a bisexual guy. So I clenched my cheeks together, and that allowed me to last longer than I would’ve expected given this first sexual experience. Eventually I told her that I was ready, and she swallowed every drop. When she gently plopped me down, naked, on to their waterbed, we kissed, and she immediately asked me if I was ready for round two. Was I? You bet!
I ate her out briefly, but Jeannie said, and I quote, “I just want to be fucked. Can you do that for me?”
At first she tried to force my cock into her pussy, but I mentioned condoms, and she kind of protested, but this was all new territory for me, so she grabbed this Trojan from the nightstand, put it on me, and we (literally) started riding waves on their waterbed. The condom was underwhelming, as condoms were at that time. You couldn’t feel anything except warmth, and could sense the wetness.
Jeannie started this thing where she would slap her body down on mine (she was on top — duh!) and the waves of the waterbed would cause me to pound her harder. But she kept insisting that we switch up positions, and we did.
The fucking was vigorous, and she was loud. The thumping sound from upstairs drowned us out most likely. I felt like a fucking adonis in the sense that I just kept fucking her. The slosh of their waterbed just made things that much hotter. By the time that I emptied into the condom, when we were in mish, I was sweating profusely. And I was exhausted. We had some brief pillow talk before Jeannie asked me if I wanted to see what they were doing upstairs.
The choice in music had quieted down. It was like this “adult jazz” genre where the music was uninteresting, and I could easily see someone buying that shit in a drunken state from QVC on a late Friday night.
And then I saw them as Jeannie stood on the steps of their split level. Doug had Lee bent over a couch in their main living space, Lee’s dress was pushed up around her belly, and her now-lost blonde curls were clenched around his fist as he pounded her. She was still wearing her heels (she was never interested in fucking in her heels in as much as I wanted her to) and no sooner did Jeannie and I watch this master class in Doug fucking my girlfriend that he pulled out and sprayed a load of his cum over his back. My body reacted immediately. I could feel my nipples getting hard, and yeah, my cock got rock hard again.
Jeannie knelt before me and started sucking me off. They were just coming off their afterglow, and I whispered to Jeannie that I wanted to take it back downstairs. She asked me if I was ready to go again, so I gyrated my hips, my fat, shitty penis slapping on each of my hips. I asked her if she would put her heels back on, and she asked me if that’s what I wanted. I said that it was. My tongue went into her pussy again as I bent her over the couch, and I went into her bare as we fucked on the pool table, when she rode me on their couch, when we fucked on the floor near the pool table, etc.
She told me that she wanted me load, and while it took me a while to build up my excitement, I delivered. And that’s when I caught Doug and Lee watching us from the corner of my eye. As soon as I pulled out, Doug tapped my shoulder and took sloppy seconds. Lee was crying — crying! — and insisted that we get dressed and leave.
I guess that Lee didn’t enjoy watching me fuck somebody else. Oh well. We ended up going home and fucking, and then we argued for the next day or so before I went back to my hovel. Still, I learned a lot from this experience. It was life changing. Yes, Lee and I weren’t destined to be married, and that’s a good thing. We would’ve been divorced long over by now. My takeaway from this all that is that am constantly trying to keep an eye on sexual people like myself, and even better when I have a partner who’s looking for the same.
Source: reddit.com/r/gonewildstories/comments/jrtgna/mfmf_the_reluctant_holiday_swap