TL;DR A pushing 60 widower tells you about the time I was in the worst relationship ever and during its breakdown got sucked into this threesome which, by the way, I loved. Then we broke up shortly thereafter.
Lee and I worked at the same place while I was in my later years of college. I’d like to say that she was a nice girl, but no, she was the biggest bitch I’d ever met. I took to her because she was known to fuck and as a guy who’s always been hyper sexual and open to new experiences, that’s exactly what I was looking for. Being a computer science type of nerd, no matter my looks, has been stifling to dating sometimes, well, or at least it was when I was younger. Plus I wasn’t a frat guy, so the dating pool just wasn’t built in. And I didn’t seek it out in any case. I had finally gotten into a good college and didn’t want to fuck it up… until I almost entirely did.
Lee was on me from the day I started that job. So I did what any horny fucker would do and I asked her out. To my surprise, even after all her flirtations, she said no. I kind of ignored her and either worked (and saw her at work) or studied. Plus I’d been kind of embarrassed; while it was a shit job, we’d been coworkers after all. Then we ended up attending the same Christmas party together, she got handsy with me, then invited me back to her place as we somehow ended up sharing a cab back to Cambridge. We’re both tall people, and me being into her sexual prowess and tight body was what drove me to sleep with her that night. I knew we were incompatible. She knew we were incompatible.
But a crazy thing happened. Physically we were mostly compatible. She was a LOT more experienced sexually than I and she coached me about how to make her cum — and I did so. She had the smallest tits I had ever seen but when she forced my mouth down on each of her tiny nipples, that’s when her cumming first started. We ended up laying around naked together all day Saturday, arguing, fucking, drinking some wine, fucking, having a snack, fucking, suggesting new positions, fucking, arguing, fucking, viciously arguing, fucking, and so on. Eventually I headed back to my apartment on Saturday night after the last argument. I figured that the whole thing was played out. I was incorrect.
Lee showed up at my school office the following Thursday (I have no idea how she found out where I would be, but whatever) and asked if I would mind if she came over and made us dinner. I remember all of the heads of my male fellow students turning as her heels clicked loudly on the hard surfaces of the floor, how her hips swayed in her short dress, or how her blouse had that extra button unbuttoned for effect. Was it a good idea for me to let her come to my apartment to make dinner? It was not, reader. But I’m sure you already knew where this story was going.
Dinner was uneventful. She was actually quite a good cook. She’d had a few glasses of wine (I had classes the next day so I declined) and then her dirty talk started. “You’re a Catholic boy, right?” she asked. I suppose that a picture of Jesus that my Mom had hung on the wall gave it away.
“Yeah,” I said. It was true that this was my last relationship before I went full-on atheist.
“Mmm,” she purred, nodding her head at me. “You know what that means, right?”
“Wait, you’re Catholic?”
“Devout,” she replied. “I go to mass twice per week.” (Yes, reader, this happened exactly as I am writing it.)
“Ah, that’s cool.” (I lied.)
“So here’s the deal,” she said, taking a long slug from her wine. “It’s au natural from here on forward and we let nature take its course. Otherwise we end it now, but you can keep the leftovers.”
“What? I didn’t think we’d even started it.”
“You know what I mean. You’re a smart guy.”
“Uhh…” I just sat there on my couch kind of slouched down. What was happening here?! It seemed kind of depraved and yet I couldn’t wait to see where this was going.
“Why don’t you stand up and drop your pants?”
I did as I was told.
“And your underpants. Who fucks with underpants on?” I had never been with a woman before who used the word “fuck” so openly. I don’t know what happened in Lee’s life but this women knew how to seduce, and we were only 22. Holy crap. The ex I ended up hate fucking years later knew how to operate as well but she was a seductress who wanted to be topped… by everyone. Lee’s approach was beyond different.
“That’s it,” she said. “Now…” She poured some olive oil from the bottle into her hand and walked over to me.
“Pull up my skirt,” she commanded. “If you get oil on it it’ll be ruined and I’ll kick your ass. Count on it.”
I hiked up her skirt.
“Higher!”
She wasn’t wearing panties. Mmm. This was also new to me.
“I get a little dry sometimes,” she explained, “so this will help. Plus it’s also pretty tasty, you’ll see.” She smeared olive oil all over my cock and balls. Then she smeared some on to her sex and started rubbing on me. I almost came then and there as she mounted me reverse cowgirl as I still sat on the couch. “Hold my skirt up… if I have to tell you again! …” I hiked up her skirt again. Her sheer meanness was astounding. And exciting. She plunged up and down on me and her fingers were probing the area underneath my scrotum. This had never happened before and I was both shocked and totally enjoying it. I had wanted to reach up to squeeze her nipples, but I suppose I was afraid to let her skirt drop so I kept my hands holding her skirt as she rode me.
She would squeeze my balls now and again, REALLY hard, and it hurt. I don’t know if she was trying to keep me hard or what, but eventually she cooed, “mmm, feels like someone is getting close…”
I couldn’t take it anymore and I told her that I was cumming. She slammed her crotch down on me and there was no pulling out. I came and came and came. “Good,” she hissed. “That felt good, didn’t it. Didn’t it?!”
I nodded when her head shot around and she glared at me.
“Well, did it?!”
“Yes,” I replied.
“I’m sorry what was that?”
“Yes.”
“What?”
“YES!!”
“mmm, now I need you do something for me,” she replied, using her hands to push her off my hips. She laid spread eagle next to me on the couch and held her legs up with her arms. She took one arm off her leg to point at her pussy and when I didn’t get it at first she did it again… and looked super stern about it. Jeez.
“Mouth on pussy… NOW!”
I started eating her and she corrected my technique — while also telling me to hold her legs up. Of course I obliged. She’d been somewhat quiet as I ate her, and while she had offered suggestions about technique and told me that it was “good” as I went, she was otherwise non responsive. The ex I’d been with before I came to this school had been a screamer. Oh, sure everyone is different and all but hmm.
“uhh, now,” her voice went up a couple of octaves as she grabbed the back of my head and shoved my mouth on to her pussy. “Nowwwww!!” My mouth and tongue were greeted with the huge cum load I had just dumped in her plus a squirt of something new. Girl cum. This was a first. I almost threw up because I wasn’t ready but when I look back this was a hot moment. Really hot. When she came down from her cumming she grabbed my hair in an attempt to push my head away. I moved away from her and got up.
“Well, what are you waiting for?!” she demanded. “Are you going to get up or what?” I got up from where I’d been kneeling on the tiled floor. My legs ached and I felt like I was going to collapse. I was young then and had good knees, but still new sexual experiences would floor my like that. She strutted into my bedroom and stripped. I took off my own clothes.
She laid in the center of the bed and spread her legs. “I want you to fuck me.” I started trying to kiss and to touch and so forth but she pointed at her pussy and said, “just fuck me.” I fucked her missionary style and it was like fucking a warm body — I can’t lie. No heavy breathing. No moans. Nothing. Just the sound of my sack hitting her bottom side as a bottomed out. I wasn’t enjoying it. I’d been at it for a bit when she asked me plainly, “are you going to cum anytime soon?”
I told her that I wasn’t going to and that I was just enjoying it. “I’m not enjoying it,” she said plainly once more. “Get off.”
She got dressed while lecturing me about how to seduce a woman properly and left. What in the ever-living fuck?!
The next academic quarter was like that. Yeah we’re getting to the threesome part, but to get from here to there a lot happened and I’m trying to cover it as quickly as I can. As it turns out I got super distracted from my studies and it showed. I got fired from my shit job. I got a new shit job. Lee was into blowing me and did it often — where she did not ask for nor want reciprocation. She wouldn’t let me face fuck her. But she was upset about, of all things, how I couldn’t cum from her blowing me. So one Saturday morning, right after breakfast, she summoned me to the bathroom and told me to strip. She was wearing black stiletto heels (that was her shoe of choice — and she wore them well) and nothing else. She squatted down in front of the toilet and I stood in front of her.
“Know what we’re going to do right now?” she asked.
“You’re going to blow me?”
“Smart boy, but this time you’re going to cum. And I mean it.”
Her mouth worked me, and frankly she’d always been very good. She didn’t even protest this time when I pumped my hips towards her mouth a little bit. My eyes were closed and I was trying to focus both on enjoying the moment and on cumming. I could hear that she was playing with herself and when I opened my eyes for a moment I saw her squirt a handful of K-Y jelly into her palm. She slapped at my legs so that I spread them wider and then her fingers snaked up well behind my scrotum. She was rubbing K-Y into my asshole. Never in my life would I have every imagined enjoying that sensation. She forcefully shoved one of her fingers into my asshole as far as it would go. And that’s when I totally lost it. She gagged and her eyes suddenly became bloodshot but she swallowed it all. She rinsed her mouth out with mouthwash and splashed water on her face. Then she got dressed and left.
In spite of what she told her parents we did not have a normal dating life. Her mother told me point black that Lee loved me and wondered how serious things were. I was at a loss for words. Lee stripped us naked as we lay in her parents’ family room (I had thought that nobody was home) and blew me and fingered my asshole when suddenly her dad appeared outside and was mowing the lawn about 10 feet away from the sliding door where I was getting finger banged and lewdly blown by his daughter. Then she rode me and had a loud orgasm, as she watched him mow the lawn, before I came in her and she walked out of the room without saying anything.
She blew me to completion in the (now closed or closing soon) Curious George store in Cambridge.
She forced her female roommate and I to fuck (or I guess that we all had too much to drink and she goaded us to fuck so we ended up having awkward drunken sex) while she masturbated as she watched. Then I watched her having drunken sex with her roommate. Apparently they had sex often, and that was something I learned later. Oh to have been a fly on that wall.
We fucked very open and in public, the most brazen of these activities took place near the bocce pits in the North End of Boston. She wanted to blow me in the Thirsty Scholar bar but that would’ve just been crass and I refused; she joked that she was a “thirsty scholar” and while it was true that she was thirsty, a scholar she was not. Even though she would never wear what I asked (she claimed angrily that she refused to dress “like a whore”) but when we’d go out she’d… dress like a whore. I loved it and I admit it.
The grand finale before the threesome happened was the night that she was dressed super slutty, I could swear she was going to pick up this muscular guy from this bar downtown, I had been feeling kind of drunk and jealous (she was also drunk but clearly not jealous), and then she took me home and she let me ravage her until she took control and pegged me with a strap on she’d bought from god knows where. She did it again the next morning and once again before she said that the party was over and she left. Again, the ass play? It’s not something I’d ever thought of, but then this relationship happened and suddenly I became fine with it.
That Monday my advisor sent me an email and told me that we had to meet. The school was considering dismissing me and I was already on probation. I’d done really well for 18 months then suddenly it had gone to shit. I don’t even have to explain why. But when my advisor and I met and he asked me what was going on I have strong memories around telling him sheepishly, while bowing my head that, “I’ve been having a lot of sex.” He stifled his laughter and asked how much of a break I’d need from school. We decided that I’d table the rest of the year, and while it was reprehensible to eat the cost of time wasted, I’d start again the next school year. Between work and loans I’d been paying my way, so at least I didn’t have to tell my parents. I’m glad that I didn’t have to divulge that Nympho Catholic Lee and I had fucked my way out of school. It’s not like that didn’t guess (they knew and have since told me), but having the conversation would have been a brutal one.
Lee and I, perhaps not surprisingly, cooled off after she learned that I was taking a break from school. I worked at a chain restaurant as a waiter and busboy, and intermittently she would either tell me that I sucked because I was an “elitist” or because I worked as a waiter at a Bennigan’s type of place in Somerville. But of course it was my elitism that ruined it. Minimum wage for servers was like $2/hr and at the end of the year I made something like $4k in 1980s dollars. I was super elite. Clearly.
Lee called me up excited one Friday night, and I just happened to be home. I’d worked a lot of extra shifts that week and the boss gave me Friday off for some reason. I met her at this “upscale sports bar” (the irony is not lost on me) and she looked her slutty best. It was almost like nothing had happened, and since I’d not been with anyone else in 6 weeks I was looking forward to being with her that night. That’s when Bob arrived. Bob was a guy who played college football in town. He was a big dude, the strong, silent, very angry type.
Lee and Bob openly flirted and I admit that I was gobsmacked. I got a little bit drunk and was about to slap some money on the bar and leave when Lee turned to me and asked if I’d join them at his apartment. Join them? Whaaaat?!
The weak feeling came back to my knees and I was also pretty pissed. For a woman I didn’t understand and knew I wouldn’t ever marry these feelings were very silly. Still all of the bullshit in the relationship had come to a head with this. I should’ve walked but I didn’t. Her erratic nature and sexual daring excited me — I knew it, and I’m sure that she knew it so that’s why she always pushed those buttons — and I was honest with myself that I’d always been curious about this kind of threesome.
The three of us rode back to Bob’s apartment in the back of a cab. His arm was around her and her hand traced up my thigh as her fingers would glance my scrotum now and again. Bob started kissing her neck and my hand started pinching her nipple through her tight dress. Bob’s hand made its way up her skirt right before we arrived at his apartment.
We went inside, and for a college athlete I admit that his apartment was a heck of a lot nicer than mine. He offered us a drink but Lee said that we there there for a specific reason and she stripped totally naked right in front of us. We both paused and watched the show. She implored us to get undressed then knelt in front of his sofa and motioned us to join her. We were standing hip to hip and I felt bad that I was dripping precum all over his floor. She grabbed both of our dicks and alternated sucking them. We ended up getting pushed together so Bob’s and my arms ended up around one another’s waists. That’s when she pushed our cocks together and started sucking them both at once. Bob started grabbing my ass which was strange but also a new sensation.
Then she stopped and Bob started to move into position to eat her out.
“No!” she exclaimed. She pointed to me. “I want to see your mouth… on Bob.”
“On Bob?”
She pointed at his dick. I had never sucked a dick before and Bob’s eyes grew wide (I almost laughed out loud at how a tough guy like Bob nearly freaked out that I was about to suck his dick). Bob was having trouble with this arrangement and I was struggling with his massiveness as well. I almost puked. Yikes. Lee stopped this activity and got on all fours on the couch. She motioned for Bob to take her mouth. I just stood there like a dumbass initially and watched. Then as I enjoyed watching him fuck her face (what? she let him do that?!) I started playing with her pussy. I got behind her and took her doggy as Bob railed her mouth. I knew that she was loving it because each time he’d plunge into her mouth her pussy would clench on my cock. Unlike our other times together this time she was making this guttural moan. She must’ve been loving it.
Finally I couldn’t take it anymore and I started pounding as hard as I could and I came in her without warning.
She slapped Bob on the hips and he stopped fucking her face. “Oh my go… what did you?” She reached around to her pussy and pulled some cum out. She gave me a dirty look and I immediately cleaned her out with my tongue. That’s when she came the first time. Bob tapped me on the shoulder and I moved out of the way. He took her doggy and I admit that his sheer aggressiveness was beyond impressive. I wish I had some of those scorecards with me. While the Russian would’ve given him a 2.3 I’d have given him a 4.0. Bob really stuck the dismount as well.
We tried DP and it was fine. We tried various combinations and Lee was excited and came a bunch of times. Eventually Bob took her missionary and they went into their own little world. I got dressed and left. Nobody said anything which was to be expected. Lee called me angrily a couple of times over the next week and left some humdingers of messages on my answering machine. She called me a “loser” and told me to never call her again. That turned out to be a wise choice because I got it back together and after some fits in starts in my later adult years settled in and have been mostly enjoying life.
Source: reddit.com/r/gonewildstories/comments/bqbkaz/mmf_an_unexpected_threesome_some_bi_and_pegging
The story was way too long
Email did exist then but even MIT didn’t give undergrads accounts until much later. Other than that they say don’t stick your dick in crazy but that’s definitely the hottest place to stick it.
Love the narrative quoted text. Great read