TL;DR I met a woman on a vanilla dating website. We had a sexy phone call then a so-so date that turned the corner after we went clubbing, went back to her place, and spent the night together.
Once I came to terms with the fact that I’m a person with a huge appetite for sex and kink, it made dating a lot easier. Simply put, I needed to date someone who was into similar things as I, but a lot of that had to do with sex rather than, say, making music or going apple picking or reading or having some laughs, you know, the basic stuff.
At first I tried to meet women through an adult site, e.g. AFF. Result? Total bust. Then I decided to use the vanilla dating sites and literally search for women who were bound to satisfy the sexual part of the relationship that I so desired. And that’s when I found Jules (not her real name).
She was about 15 years older, but I liked her pictures, and her ad was suggestive enough to catch my attention. I replied back, and tried to be witty, but also made some suggestive remarks myself. To my surprise (and delight!) she got back to me, and upped the suggestive game. About 4 messages in, she sent along her phone number, and our chat that Sunday night was over the top.
We flirted back and forth on the phone call and then she readily volunteered that she was highly submissive, liked to dress like a slut (her words), had a strong desire to get involved with someone who was into sharing her, and that she wanted to share “her man” as well. She also said flat out that she was into activities with other women. In all? It was fucking hot. She even gave me the rundown of her “slut wear” — and it included my favorites like short skirts, stockings, thongs, heels, putting her cleavage on display, latex/rubber wear, etc.
Needless to say we set a date for the following Saturday. I couldn’t wait. Was this too good to be true? Was she going to show up? Time would tell, and it did.
She recommended this college’y type of place in Boston. It was loud, it was a dump, I hated the menu offerings, and plus she was late. Like really, really late. I had just gotten out of the booth and was about to leave the place when she (finally) arrived. Too bad that Boston was unseasonably cold that winter, because I didn’t get a chance to check her out, which, by the way, I would’ve done unapologetically. Since I figured that we were on a date to determine if we would become FWBs, my manners were less than stellar in that regard.
I met her at the door and she apologized for being late. Then she made note that it was really loud in there (no shit!), and asked if we should go someplace else. We tried a few other places, but even though it was frigid out, the wait time for most restaurants in the city was like 45 minutes. And we were both starving, go figure.
We found this one out of the way Ethiopian restaurant and it was nearly empty. That would give us the perfect opportunity to chat in privacy, and mercifully without the godawful racket that was taking place in that first place.
The host took our coats and seated us in a back corner of the restaurant. Nobody was there, and the environment was charming with its basket chairs and tables. They took our drink order (they recommended this honey wine, and we both shrugged and said that we’d take half a carafe). The wine? It was like mead, only cloudier and more dense, and my god… the alcohol content. Oh, the alcohol content. Back then I was pretty much a teetotaler, so this was a lot for me. I was buzzed after a sip or two, and had to keep chasing with water.
With the tiny basket tables and the basket chairs basically being tiny stools with cushions, I got to take Jules in. She was wearing, well, tight *everything*. Her flannel shirt, it with 3 buttons unbuttoned, was tight, and was knotted at the bottom. Her short skirt was tight. She was wearing tights of some sort, which are tight by nature. Even her over-the-knee leather boots were tight against her legs. She was super busty, which I had not gleaned from her pictures. Her hair was clipped up and had this two-color sexy thing going on, with what looked like a blonde to dark fade. She was wearing too much makeup, which I usually hate, but it worked in context.
Oh yeah, and plus she was wearing an engagement ring / wedding band combo on the ring finger of her left hand. I wasn’t going to ask then, in particular because her ad said that she was single, but I was curious. Like, immensely curious.
And I could feel her eyes on me as well.
At first it was all small talk, which one would expect. It wasn’t bad or awkward. It’s just that it hadn’t come around to our hot chat on Sunday. I needed to change that, and in a hurry. Otherwise, the Friend Zone was right around the corner.
“You look really great,” I said, and I made the “OK” sign with both hands.
“Ah, thanks,” Jules replied. “Oh, and there’s something else you might like…”
“Oh? What’s that?” I asked.
She unbuttoned a couple more buttons on her flannel, and showed me the black, rubber, shirt (it had a huge red start in the center of it) she was wearing underneath of it. It was tight, and as she pulled her shirt open, I saw a ton of cleavage and her nipples were straining to poke their way through it.
I whispered to her how hot this was, and she reached her hand over the basket table and squeezed my hand — before pulling her hand back and re-buttoning the buttons that she just undid.
And that’s when I knew: “play it cool, dude, and this is going to happen.”
Dinner was great, and I admit that I was a little buzzed when we were leaving the restaurant. Jules seemed fine, but she did admit that she enjoyed partying a bit. I have this rule about not having sexual encounters while impaired, and she seemed within bounds at that point.
Then she suggested that we go clubbing. I hate dancing. I’m horrible at it. Plus the crowds and the ear-punishing noise also rattles my bowels. And I’d just consumed all of this awesome (but heavy) Ethiopian food. Still, I stood somewhat still, we packed on to the dance floor and before long Jules took the lead (odd for a submissive, but I was actually relieved). I didn’t make a fool of myself, thankfully, and she turned her back to me and bounced her ass against my crotch. I grabbed a hold of her wide hips, giving playful spanks on her rump here and there, and she returned the favor by continuing to grind her ass, full on, into my obvious hardness.
We retreated into a dark part of the club and started making out a bit. Man, she *was* submissive. My tongue and hands were unencumbered by any form of protest. She whispered (yell-whispered actually) in my ear that she wanted to go for a drink, so we left the club and went to this empty dive closer to her place. She had a shot and I drank a coffee.
Then she invited me back to her place for “tea”. I shit you not. Tea. Fucking tea! Tea is hot, but drinking tea is NOT.
I downed a couple of Altoids while she was making the tea (it turned out to be a toddy), and we sat side by side on a loveseat. Her apartment was tiny, like many (if not most) Boston apartments are, and there was barely any furniture. There was no tv. Nothing was hanging on the walls. The only thing that was hanging were strands of white Christmas lights.
I sipped gently at my toddy as I wasn’t sure that I, as a teetotaler, wanted to drive home in an encumbered state, when Jules told me that she had something to show me. She pulled this shoebox out from under the coffee table and asked me what she thought of these shoes that she just bought. Leopard print? Check. Ankle straps? Check. 4 or 5″ heel? Check. Hot? Definitely. She asked if I liked them.
I said that they were hot, but there was a problem.
She asked me what the problem was.
I replied, in a somewhat snarky way, that she wasn’t wearing the heels. She kind of giggled and took another sip of her toddy. She set the heels on the coffee table, and I couldn’t get them out of my peripheral vision.
We started making out again, and I admit that hot toddy breath is actually legitimately hot, when she broke the kiss, grabbing the heels by the straps, and excused herself to the bathroom. I heard the water running. I heard a toilet flushing. It felt like it was forever. I would’ve consulted my iPhone to see how long it took (there was no visible clock in the place), but the iPhone had not been invented yet.
Finally Jules emerged from the bathroom. She was wearing nothing but her rubber shirt, a thong (she did a turn for me), and the sexy heels. I’m not a foot guy but her toenail polish and the super-high heels really set me off. The rubber shirt was a half shirt, and her navel piercing was in plain view. I could tell that she was wearing a thong by the way it disappeared between her legs. She had a very visible “thigh gap” which I’ve always found to be super hot — in that I could see a patch of light between her thighs as she stood with her feet together. As she came into even the dim light the sheerness of her black thong was evident, and even more evident was the fact that she was bare downstairs. I cannot tell you how great it is to plant your mouth on a bare pussy, and it was my very intention to do just that.
I told her how hot she looked, and patted the sofa cushion next to me on the loveseat. She sat down next to me, and I hopped off the loveseat and immediately went to remove her thong. I shoved it into the back pocket of my dress pants, and yes I had every intention of keeping it. My mouth immediately found her open spot as I tossed her legs over my shoulders. Her sexy heels clanked against my back. She was very quiet, but was breathing heavily, and that concerned me. I hoped that she was enjoying it but didn’t stop to ask. I just kept going, well, until I saw her back arching and I felt a squirt of warmth in my mouth.
She dragged me by the hand to her bed, and wondered why my cock was out. I told her how hot this was and how I’d been priming the pump (she giggled). Her mouth was amazing, and she too was happy that I kept myself bare down there. Her fingers snaked between my balls and my asshole (I was kind of hoping that she would play with it) and her tongue was totally expert as she worked up and down my shaft and did masterful work on my sensitive head.
I gave warning and she swallowed it all. Then we kissed, and I could taste our combination. She asked me if I minded it and I told her no. In fact I told her how much I liked it and we ended up round two, starting with my mouth on her pussy again and then she found it fit to do a 69, which for me at least? Normally sucks. I can’t concentrate. But this time it was awesome.
We ended up falling asleep and at some point in the middle of the night I felt a softness on my neck and a wetness on my then-hard cock. I whispered to her that it was so awesome, and I ended up sliding right in. We went a couple of strokes, but then we (stupid us!) decided to roll with a condom and we ended up having a nice slow fuck. She was still wearing the rubber shirt, which disappointed me because I wanted to see her tits and suck on her nipples, and her heels (which is hot like 200% of the time). She came at least twice as things escalated — once I started the dirty talk about our slow fuck and how it was so hot to be inside of someone who had a wedding ring that nice (really, it was nice!), and we finished at some point before dawn.
We woke up spooning and she was just wearing heels at that point. Morning breath is the worst, so we used our mouths in other ways, and after a short patch of missionary, I flipped around and went to doggy. I pulled out at some point and gave a treatment with my tongue to her pussy, and then rimmed her mercilessly, then I went back to doggy and we finished up.
We ended up having brunch at this place called Doyle’s in Boston. That’s when she told me about her husband and their arrangement. It was cool by me, and we decided to keep carrying on (and also involving other people later on if it worked), and so that’s where we went with it.
A week or so later she asked if I stole her thong, and I fessed up that I had been jerking off into it for days. So she said, “I want to see you jerk off into it the next time I see you.” I washed it, and in our next naked session, right before she had to leave her apartment to go back to her husband, I jerked off into the thong until completion, and she obliged by wearing it, soaked with cum, as she got dressed to head home to her husband.
I never ended up meeting her husband, but we carried on for quite some time, went to swing parties, etc. She once wore nothing but an apron, a dog collar, and heels for a dinner party at her apartment, so suffice it to say that I was more than pleased. More on Jules later on.
Source: reddit.com/r/gonewildstories/comments/jb8bvc/mf_i_knew_that_we_were_going_to_fuck