[MF] An affair I can’t help but remember [LONG-ISH]

This may end up to be half a story, half a journal entry. So if you want a weird mix of sexy times, self deprecation, introspection, confession, and reflection, then hell, maybe this will be for you. This all takes place when I was in my early thirties (I’m 42 now). I was sliding pretty quickly into the depths of my sex addiction. Despite being in a happy marriage I was using porn every day, masturbating multiple times a day, catfishing women online, escorts, strip clubs, rub and tugs…it was snowballing pretty fast. Not proud of it.

I’m a musician (nothing sexy, I play weddings and corporate gigs, so I’m like the bottom of the barrel on the “rock star” scale) and had a gig about 4 hours out of town. I check in to the hotel the client reserved for me, and head out for the night since me gig isn’t until the following day. I pull up a seat in a local restaurant and bar that I had been to on previous trips to that town, and proceeded to eat alone like complete winner. Shortly after I sit down, a group of four women in their early 40’s walks in and asks if they can sit at my community table with me. I agree and we all get to talking. They’re teachers attending a conference and they are apparently interested in drowning the traumatic memories of their classrooms in copious amounts of alcohol. As the night wears on, I match them drink for drink and find myself pretty faded since I’m an utter lightweight.

I had my eye on one of the women since they first sat down, but somehow, thanks to the effects of alcohol, I found myself in some pretty heavy flirtation with someone different, a woman we’ll call Sarah. She wasn’t what anyone would say was gorgeous per se, but she was very much my type…Short, probably about 20-30 pounds overweigh so she had some really nice curves, a nice smile, brunette, and there was just something about her face I came to adore. We’re holding hands, standing way too close to each other and eventually we head outside and find a dark corner away from the restaurant. We start making out like high school kids. I’m pretty drunk and I’m quite confident there was nothing enticing about my kissing. I’m thinking there was too much tongue, too much groping, mouth open too wide…just a hot mess everywhere. But for some reason she seemed to like me. Lucky me.

Sarah and I exchange numbers and the night ends as abruptly as it had begun. As I head back to my hotel, we’re texting back and forth, flirty stuff but nothing too overt. I get back to my room, furiously rub one out, and fall asleep only to wake up to a wicked hangover the next morning,

The next day, much to my delight, the texting picked up as she’s attending her conference. I become more and more forward and we eventually get to a point where we’re essentially sexting while she’s in the middle of her seminar. At one point she texted me, “you’re making me so wet.” From that point on I was smitten. Sarah was cute, willing to be forward sexually, and seemed to like me. It was on like Donkey Kong.

I play my gig and head back to my hometown, about four hours away from where Sara lives in Denver. Over the next couple of months we text back and forth pretty much non stop. Typical flirty sext-ey type stuff. I think we exchanged a few photos but Sarah was somewhat reserved when it came to that. After about three months, I arranged a gig in Denver, and I told her I was coming to town and asked if would she stay the night with me at my hotel. She agrees and my heart begins to race.

Some quick backstory. I was a late bloomer. Until that point, my wife was the only person I had ever had sex with (the escorts were typically massages and occasional oral sex), and I didn’t lose my virginity until I was 25. Despite my misbehavior in others forms during our marriage, I had not had a proper “affair” so I was simultaneously exhilarated and terrified by the idea of being with this new woman in-person, at a hotel, overnight…

**The first time.**

The day finally arrives and I drive down to Denver for my gig. I text Sarah to tell her what hotel and what room and she says she’ll meet me there. The room is standard fare…Marriott in the tech center surrounded by business parks accessed by the interstate. Once I’ve checked in, my heart is in my throat. I’m constantly checking out the window to see if there’s a car pulling up. I’m pacing back and forth..I just don’t know what to do with myself. There’s this insane adrenaline coursing through my veins, butterflies about seeing her again after months of flirting via text, guilt about the decisions I’m making, it’s a weird cocktail.

And then it happens, a knock on the door. I open it and there she is, looking equally as nervous and uneasy as I am. I invite her in, she sets her bag on the floor and produces a bottle of wine. Good idea. We grab a couple of glasses and proceed to drink it way too fast to help take enough of the edge off. At first the conversation is a little stifled but it doesn’t take long for the wine to start helping out and we’re settling in, getting a little bit flirty with each other. We debate going out to dinner but neither of us seem to anxious to leave the room. It’s like, despite our nerves, we’re both too excited with the thought of what’s inevitably coming. Midway through my second glass (I told you, I’m a lightweight), I walk over to her, ask if I can kiss her and she smiles and tells me yes. So I do. It’s nothing like our first awkward high-school-style makeout session outside the restaurant. I come to realize that I love kissing her. She’s great at it. The perfect amount of playfulness and tongue (my wife doesn’t really like to do more than what could be described as a hefty peck). I hold her head in my hands and revel in the simple yet sensual experience of kissing her.

A quick note because some of you may be wondering. I’m in my early 40’s, athletic, trim build and overall pretty well proportioned. I’m a smaller guy, tipping the scales at 150, and I’m only 5’8 so if reddit has taught me anything about tinder, I’d probably strike out. But I have to say, for my age, I think I look pretty damn good. Where all my friends have graduated to full on pear-shaped dad bod, I still look trim and muscular. My dick is tremendously adequate. It’s right at 6 inches and, as far as dicks are concerned, perfectly lovely. Sarah is about 5’2, dark brown hair with the ubiquitous “Karen” cut, really nice big tits that I came to realize later on had a little help from a surgeon. And her face was just…gorgeous. Like I said, I don’t think she’d necessarily turn heads when she walked into a room, but for me, she was absolutely amazing. It gets my heart racing even these years later.

OK, back to the story…As we kiss our hands start exploring. She reaches down to feel my hardening cock through my jeans and at that point something changed. Any thoughts of slowing down and going out to dinner or taking some more time to drink wine and talk goes out the window. We immediately start to undress each other. I get her down to her matching black lace bra and panties and I’m more drunk with lust than I ever was with wine. I just feel this primal hunger for her, like she was the air I needed to breathe and the water I needed to drink. I slide off her panties and push her down on the bed. She spreads her legs and I immediately begin to eat her cleanly waxed pussy. I notice she’s much more verbal than my wife, moaning loudly and telling me how good it feels. Multiple times she just says my name in ecstasy, which I had never heard from my wife, and it was just about the sexiest thing my ears had ever heard.

I love eating pussy, like…love it. And I don’t have a chance to often in my marriage, so I just stayed down there as long as Sarah would let me. As I toyed with Sarah’s clit with my tongue I could feel her squirming more and more and her breathing becoming heavier and faster. Soon enough she was cumming loud enough that I’m certain anyone passing by in the hotel hallway would have heard very clearly.

After her first orgasm, we both take a brief moment to recover and enjoy a long, slow, passionate kiss before I go back to work between her thighs. This time it’s much faster and she cums a second time within just a few minutes. Then she says something that just about makes me explode. “I want you inside me.” You have to understand, I love my wife but our sex life is pretty vanilla. No dirty talk, no oral sex to speak of, no doggie, she doesn’t like me playing with her ass or tits, she’s not a big kisser…so hearing someone tell me, in essence, that they want to be fucked just makes my head spin.

Here’s where some of that drunk with lust stuff starts to play with my rational mind. Without really thinking anything of it, I slide myself into her. My first thought was, “man, she is really wet and she feels amazing.” That’s followed shortly by, “holy shit, I didn’t put on a condom.” Sarah doesn’t seem at all concerned so we just start fucking away like two rabbits, all sorts of different positions. Her on the edge of the bed with my feet on the floor. Missionary with her legs up by my head. Against the wall. Doggie. I come to realize Sarah loves being fucked from behind. As the pace picks up, so does the noise we’re making. She says my name again and again and I can tell she’s about to cum a third time, and I’m right on the edge. She buries her face in the pillow and lets out a long slow moan as she cums. The combination of her curves in the half light of the room, her sweaty skin pressed against mine, the wine and lust coursing through my brain, and my ears filled with her moans make for a fog of pure desire. And I realize, a little too late I’m about to cum. I mumble something to the effect of, “I’m, uh, cum….I’m going to….where?” And she just tells me to go ahead. So I keep pumping away and cum inside her. We collapse onto the bed, panting, not necessarily paying attention to each other but more just basking in the glow of the intense sex we had just enjoyed. Eventually she gets up to, I presume, clean up a bit and get my load out of her. I love watching her walk away – this sexy, curvy, sexual woman who I barely knew but was completely smitten with.

She comes back to bed, and we just kinda lie there naked talking and recharging…both of us waiting until we can go again, which we do. And then again the next morning. It was the beginning of an intense, amazing two years between the two of us.

There are more stories and, depending on how this one is received, maybe I’ll keep going with tales of Sarah and I. This was the first time. There was a second, and third, and fourth and fifth. And even though it ended years ago, I still think of her almost daily and wish more than I anything I could reach out to her. But with how things ended between us, and with six years past since we last spoke, and with me trying (and often failing) to behave nowadays, I just don’t know that I’ll ever get to see her again. But I’d love to.

Source: reddit.com/r/gonewildstories/comments/jjycmd/mf_an_affair_i_cant_help_but_remember_longish