As always, names have been changed to protect the not-so-innocent.
TL;DR I met a woman through a “conventional” internet dating site, and we had a very interesting night of sex, in what turned out to be a one-night stand.
I went through this phase, when I hit 30, where I decided to find FWB types of relationships through regular/conventional internet dating sites. Previously I’d tried one of the major “adult” dating sites (swingers, casual sex, etc) and the action for me there was absolutely zilch. So I figured, “what the heck,” and decided to see if I could identify women on a conventional dating site who were looking for FWB and more. Ideally I wanted to find someone that I could swing with, but first things first. As an aside, I was very interested in swinging at that time. I’m still into extracurriculars now, as you’ve possibly seen in stuff that I’ve posted here before, but I’m not so much into the *lifestyle* aspect of adult activities anymore.
You might be thinking to yourself, “what a terrible idea,” but really things went a *lot* better than I would have ever expected. Now I didn’t just lead (my responses to ads) with “hey baby let’s fuck” or “U available” or “show me your tits” or “wanna swing” or anything stupid like that. In general I’d find ads, with or without pictures (this took place in 2000 where smartphones were not close to being a thing), where the writing was good and the woman who posted the ad mentioned something like “looking for excitement” and/or “not looking for anything serious”. It was a starting point at least.
Nothing happened at first. I’d exchange emails with some women but then it would kind of fizzle. Then I found the ad that changed the game. Initially was on a +/- swing of 5 years, but once I changed my search to be no less than 5 years of my age and up to and including greater than 20 years of my age, I found Trish’s ad. She was 50 at the time. Her picture was okay, but the writing was great and the contents of her ad were somewhat suggestive. Naturally I was curious, so I wrote a fun and slightly flirty response to her.
It’s not that I was into MILFs, or the “milfy” things that they do, at the time. I’m not even sure that “cougar” was a term that was used back then. It was that I wanted to share what I thought of as “pure sex” with a woman, and to take the steps with her that I just mentioned. Trish and I just happened to be on the same page, or so I thought.
She wrote me back the next day, and with each back and forth our responses got more and more suggestive. Finally she gave me her number, and asked that I give her a call. Interesting!
Sunday night rolled around and I dialed Trish’s number. I liked the sound of her voice, kinda soft, tone a little bit lower than I’d expect. She kinda purred, and I was into that part of it. However, outside of learning about her recent divorce — the “dead bedroom” and all — it was a bit awkward, as these internet meetings can be. I made reference to the “very interesting” emails we’d been exchanging, and suddenly she switched gears. We essentially started having phone sex, and it rolled up on me fast.
She asked me how I liked a woman to be dressed. I mentioned my affinity for a woman wearing high heels, oh, and of course thongs. :-). She told me that she made a mental note. Then she said that she was also into women. She told me that she was “three holes” (never heard that term before then). She said that she was into being shared, whether that be in a threesome or finding another couple to swap with. She reiterated that she wasn’t into anything serious, but she was looking for a “special friend” to hang out with on a regular basis. During the banter, I made some off-colored remark about “leathermen”, and she literally, well, she took it literally. Then she dropped the bombshell on me: she was very, very much into watching two men together, and that her ex left her with his leather stuff — and that she was into seeing me in nothing but chaps and a vest, and because we’re both large specimens, her ex’s stuff would probably fit me. A mushroom cloud suddenly appeared in my head. I thought that my head was going to explode. I just sat there with a slack jaw. For all of the years of my clandestine activity with other men, and this included my prior relationship with Linda and Bob, for the most part I thought that women thought it was “gay” and “horrible” that men would enjoy sexual relationships with one another. This was the first time that a woman actually told me that it excited her, and as noted, I was completely floored.
As Trish continued on in discussing her hotness for male-male action, she eventually realized that I wasn’t saying anything, and asked me if the cat got my tongue; I was then open about the fact that her revelation floored me. She said, “maybe you and I should find you a boy toy sometime, a boy toy that we can share.” Holy fucking shit.
Needless to say that I wanted to meet Trish in real life. We decided to meet that Saturday at a place in Boston. She said that she wanted to get dressed up, and I said that I would do the same. I ended up wearing this underwear that could best be described as “stripper-like”, and got a body wax ahead of our date.
The place that Trish selected was shitty. It was a dive for college students. The food looked terrible. The music, and I say this as someone who loves music, was god awful and *super loud*. Plus she was late, like 45 minutes late, which truly pissed me off. At that point I was pretty sure that she just fucked with me and that I was going to be stood up. I was about to leave when she entered the restaurant, or at least my best guess about how she actually looked — should the grainy picture on the dating site be believed.
She was taller than I expected, and her hair had this dyed-blonde-with-dark-roots-cut-into-a-bob style that was the rage back then. Or maybe it wasn’t the rage back then, but I used to see it a lot in 2000. Plus she was wearing this ankle-length faux fur coat and some kind of high-heeled boots. And she was also wearing way too much makeup, but again, while I don’t care for that look usually, she was pulling it off really well. My first thoughts were, “well, I’m pissed that she’s late, I’m doubly pissed that we’re all dressed up and standing in this god-forsaken restaurant, but if we have a nice dinner elsewhere then I’m going to be fucking this woman a few short hours from now.”
Over the loud music I could barely hear her telling me that I was a lot taller than she expected — and that she thought that I was a good-looking man. Or maybe she said that she was glad that I am a man. Regardless, I said that we should get out of there, and I took her hand as we strolled through downtown Boston. One of the menus caught her eyes at a place that was the exact opposite of her original choice, but, sure, let me spring for this meal. Pussy and maybe exploring kinks were on my mind at that moment.
The maitre’d took our coats, and to my surprise they had a table available on a busy Saturday night. Trish was a good looking woman, maybe a little bit of a tummy, but the curves and how she dressed (plus the purposefully overdone makeup) really caught my attention. Her blouse was sporting a *ton* of cleavage. Her skirt was — at best — upper thigh. She wore some kind of nylons or leggings underneath, and her boots went over her knees. Maybe I wasn’t the only one who had visions of fucking on that night? It was almost like Maury Povich was sitting on my shoulder and told me that a women shouldn’t dress like that in public, because they could get raped. Then again, Maury Povich is terrible… *and wrong*. “shaft_right_on, you are *not* the father! shaft_right_on, *you’ve been dressing too sexy*!” HAHA!
We ordered some drinks, and conversation was kind of awkward at first. The second round in, however, is when Trish started opening up. “So I think I did something that you’ll like,” she said. Of course I was all like, “oh, and what would *that* be?” In the middle of a crowded, upscale Boston restaurant on a Saturday night, Trish proceeded to unbutton 3 or 4 buttons on her blouse, and pulled the blouse apart so that I could see what was underneath. She was wearing this red rubber (or latex?) bustier or bra of some kind, and she gave her nipples each a couple of pinches such that they ended up poking through the thing. Then she pulled the blouse back together and (mostly) buttoned back up again. I was totally agape, and told her how great she looked. I used my peripheral vision to see if anybody was looking; yet nobody in the restaurant seemed to notice, which was totally hot and awesome. And yes, this was *exactly* how it happened.
We hit a bar after dinner then went to this this music club, where we danced. I was sick of being out at around 1am or so, so I said that I was going to call it, and asked her how she was going to get home. She said that she’d get a cab or something. I insisted that I drive her home, because in reality I was all amped up — and wanted to drive *it* home, like *repeatedly*. She agreed, and we drove on 93N a bit, all the while with my hand on her knee, before we got to her place. She asked if I wanted to come up, and of course I did, so I did.
She asked that we take off our shoes, or in her case, boots, and also asked that I hang up her coat, which I also did with mine. I was sad that she took those sexy-ass boots off. I wanted to fuck her right there while she wore them, but patience is a virtue I suppose.
Trish asked if she could make me a hot toddy, and I obliged. We sat there on her loveseat, the apartment being a total dump, basically, with Christmas lights (in March), boxes everywhere, pictures leaned against the walls, mostly zero furniture, and a rug that had visible stains… even in the semi darkness of it all, and drank our toddies. Out of the blue she said that she had something to show me. From underneath her coffee table, the rare piece of furniture in the place, she pulled out a “fuck me” type of stiletto heel — my guess was that it was a 5″ heel, but I didn’t happen to stop at Home Depot before the date to buy a measuring tape — with this ankle strap. Only this ankle strap was special because it featured a padlock. I had never seen anything like this before, just like aliens dropped this shoe from space and suddenly a civil war broke out in Somalia or something as they argued over who would possess it (there was a movie similar to this theme, but only it involved an empty soda bottle). She dropped the heel into my hand, and I examined it.
And then she started asking questions.
“This is a pretty hot shoe, isn’t it?” she asked.
“Well, I guess so,” I replied.
“What do you mean ‘you guess so’? You said that you liked heels, right? I *bought these for you*.”
“Well, yeah, it’s a pretty hot ‘shoe’, but there’s a problem.”
“Oh, and what’s that?” she replied, taking a sip from her toddy before snapping the heel out of my hands and tossing it back under the coffee table.
“That you’re not wearing them.”
“Fuck you, dude!” she blurted. She was being playful, but at the same time, and clearly, I had gotten under her skin. “Fine, you want me to wear them, then… here.” She walked over to a pile of stuff near one of the walls and tossed this heavy stuff on to my lap. Then she unlocked each padlock on the straps of the heels and tossed the key into my lap — before disappearing into what I assumed was the bedroom.
I kind of sat there in a daze for a couple of minutes. We had a cordial night, she wants me to fuck her, and I want to fuck her, but… what’s missing here? The passion, the lead up, the fun and flirtation before what should be a dynamite night: that’s what’s missing. Still, maybe we would have sexual chemistry, and she would end up becoming the FWB/swing partner that I was looking for. I examined what she sat on my lap, and sure enough it was the leather vest and chaps that she had spoken of days before.
As I heard zippers being unzipped in the other room and all kinds of shuffling to suggest that something was about to happen, I stripped down and… put on this leather vest and… the chaps. The *fucking* *chaps*. I’m not the Marlboro Man, and he (or one of them) died of cancer, I believe. I had this internal debate about whether or not I should wear my obscene stripper thong with this combo, and I guess that in a metrosexual way (at the time) I said that it didn’t match, so I just stood there in this vest and chaps, my ass completely sticking out, my fsp (fat and shitty penis) fully erect, and waited for the other shoe — pun intended — to drop.
Full disclosure: I don’t like the way that my penis looks soft, he says in a Larry David / Jerry Seinfeld voice. It is soft and skinny and short. Michaelangelo did “David”, and as we all know, it’s an iconic sculpture, but also that “David” has no dick, just like that guy from the original “Ghostbusters”. Ahem. But when I get hard it comes to life and is somehow super thick. I should see a doctor about this. HAHA! Then when it gets soft right after I’ve been hard it’s got this nice hang with ample thickness. To get the dick aesthetic that I wanted, I literally read this “Reader’s Digest” that was sitting on the coffee table — ahead of Trish presenting herself to me, and as I looked down at my guy he seemed to be in a good state. I was just hoping that she wouldn’t be that much longer. Her leatherman was waiting!
And then the bedroom door creaked. I only went to Trish’s apartment once, but I think that the entire apartment creaked. As an aside, Boston is a special place, and feel free to visit any random apartment as often as you can. HAHA!
In any case, out she strutted wearing basically nothing but this sheer black camisole, what turned out to be a g-string, and those fuck-me stilettos. You could tell that she locked the locks, because with each purposeful step towards me, you could see the locks bouncing on the ankle straps. Was this fucking hot? You bet!
As she approached, I motioned for Trish to turn for me, which she did. She stopped, waggled her hips, quickly turned one way and then quickly turned the other way. Yup, tiny string up her crack. It was totally a g-string. Then she surprised me by motioning *me* to turn. Really?! Okay, that’s cool.
Next thing I know she’s tucked up behind me, one hand massaging my nipple through the open vest, and the other going straight for my puckered asshole. OMG OMG OMG OMG! Sensory overload! Maverick’s in trouble and he’s headed out to sea!
I grabbed her hand from my nipple as I spun around, my fsp, slapping itself left and right given my abrupt movements. Yes, I was too close for missiles, so I was switching to guns, or I guess a gun. My love gun? No, that’s fucking weird.
Then we kissed for the first time. Trish was a pretty good kisser. My hands were all over her, and she basically grabbed my fsp and shoved it in between her thighs. I could feel her warmth and slickness through her barely-there g-string. Thing is? She didn’t emote *at all*. Usually there’s a moan or a grunt or something that shows one’s joy, but not on that night.
She didn’t remove the heels (she couldn’t) as I went down on her on her loveseat, her legs resting on my shoulders. She came the first time from me going down on her (I could taste it, and her squirt hit my tongue); she actually tasted quite good and pleasant.
Trish’s head game wasn’t that bad, but she just gave good head *without looking at me for a second*. We ended up on the filthy carpet for a 69. I think that the *fucking chaps* were a good luck charm, and as a result I didn’t die from a bacterial infection by writhing around on that carpet. Or something.
The only thing that Trish said during that whole time was when I was about to enter her. “Go raw, go raw!” she insisted. Granted, sheathing up would be short lived, but I took her the first time by bending her over the sofa, by having her ride me on the nasty carpet, but standing on my tiptoes to fuck her as she laid on her back on the kitchen island, as she rode me as I sat on the edge of her bathtub, and finally I finished in the condom as she sat on my lap at the edge of her futon.
We ended up crashing on her futon at maybe 3am or so, me still wearing the *fucking chaps*. During the night I had dreams about how the night *should’ve played out,* how the sex should’ve been way hotter, how I like fucking raw, how basically it was all pretty hot in theory, but not really that hot in practice. Still, I started sleep fucking Trisha raw, and soon we were just straight up fucking.
Maybe she was half asleep, but she was still kind of showing no emotion as I fucked her slow, pounded her as hard as I possibly could, stuck my finger in her ass as I took her doggy, and so on. I even held her down as she rode me, pounding her underside as I grunted before shooting a rope into her. Still, nothing. Wow, just wow.
We dozed off again then my Nextel did it’s patented “we need you right now” beeping at around 6am. The network operator on the other side of the phone was totally paranoid, and basically yelling about this system down alert. It woke Trish up, and she knew that it was real. I had to pee, then she excused herself to pee, then I got dressed (sans my stripper underwear, which I could not find), scooping up her g-string and shoving it into my back pocket before she got out of the bathroom.
I dug the key to her heels out of the couch cushions and handed it to her on the way out the door (she was still naked, well, except for the fucking hot heels).
I headed to the data / computing center kind of smelling like sex, but to my credit I wasn’t wearing the *fucking chaps*. I fixed the shit that needed fixing then headed home and crashed for 12 hours.
I figured that was it. She wanted to do it, I wanted to do it, she came at least a couple of times (as did I), but she wasn’t that into it for a repeat performance. And neither was I, really. I’ve always liked a woman who’s got *gusto* in the bedroom department, basically no matter how kinky. So I figured that was it. I wish we had that chemistry because I liked the idea of the whole thing: the passion, experiencing something new with a “special friend”, the lot of it.
Okay, so that’s not entirely true. She apparently was *quite* into it. She just kept calling and calling and calling and emailing and emailing and emailing. The worst of the calls happened when my parents were visiting. I happened to get called in the middle of their second night in town, and as was par for the course, they’d hear the answering machine pick up, then they’d take notes about who called and what they said.
When my mother was bent out of shape later the same morning, I asked my dad what was up. “Oh,” he said. “Do you know someone named Trish?”
“Uh, yeah,” I squinted my eyes.
“Well, she called this morning and said that she ‘still wants your dick’. Your mother is kind of upset about having written that down.”
And that’s, again, *exactly* how it happened. In a way I thought about calling Trish, but how can you tell someone that you wish that they would show that they enjoyed pleasure? You can’t. I actually enjoyed the *idea* of fucking Trish, and hoped that maybe more practice would bring perfection, but not the actual results.
I ended up with a delightfully inappropriate girlfriend about 3 months after that, but that’s a story for another time.
Source: reddit.com/r/gonewildstories/comments/11klw6v/mf_my_ons_with_a_woman_i_met_on_a_conventional