My First Affair with an Older Married Woman [MF]

After writing my last confession, I realized I’ve long had a thing for married women. In a way, it’s like you truly know someone when you have an affair with them. Or at least, you know a side of them that we normally keep hidden. You both have this hunger you can’t satisfy in your regular life, so you have this secret place with this secret person where you find a little thrill together.

You could say I started early. My first affair with a married woman was when I was on break from my first semester in college. Her name was Ann, and she was the hostess of a local sports bar. We had an immediate attraction, like an anvil falling from the heavens kind of connection. Magnetic. Raw. It’s rare but it happens.

I was meeting up with friends at the bar to play pool. All I did was walk past her, but we both literally turned to look at each other. She was about 5’3” and quite thin with a blonde pixie cut. Colorful flower tattoos, a stud in her nose. She had, I would later discover, fake D Cup tits and a great round ass. Big blue eyes and pouty lips. She looked a bit Russian in the face, and a lot younger than she was, almost childish in fact, but I later learned she was nearly 30.

Seeing her for the first time, it’s wasn’t a sexual feeling, it was more like, do I know you? I feel like I know you from somewhere… It was a moment we would talk about later, a connection we had that neither of us had experienced before.

All night I couldn’t take my eyes off her, and even when I did she was always on my radar. It was like I could sense her in the same room with me. And she kept looking over, keeping tabs on me too. We’d meet eyes and smile, like we both knew what the other person was feeling. I barely paid attention to my friends, who I was already feeling pretty disconnected to. I’d only been gone to college a few months, but all they wanted to do was play “remember when” and I hate “remember when”. But I stuck around and smiled and after everyone left that I night, I lingered.

I pulled on my coat and just sat in the booth, honestly a little nervous. I was only 18 – I’d definitely had a lot of “teenage” experiences, but this was obviously different. I’d never hit on anyone in a bar before, let alone the bartender. I honestly didn’t know what to do. So I did what any 18 year old guy would do. I sat in the booth with my coat on and waited for her to come talk to me. Which she did.

There was very little question about what was happening. We started talking, innocuously at first, but eventually I sat at the bar and we spent the next several hours chatting. In that time, I learned that she was 29, married, and she wasn’t normally a bartender. She was just doing it for Christmas money. She had dropped out of college after she got pregnant and married the father of her son. (I’d noticed the diamond but hadn’t asked about it.) I don’t know how to describe the conversation, except it was nice. Comfortable, but exciting. Sitting at the bar listening to this beautiful, snarky, lonely woman talk about being a house mom, doing laundry, about wanting to finish her degree. She talked about her husband’s job, her son’s inability to sleep at night. I don’t know. It wasn’t sexy – we just connected. It was one of those conversations that you’re so invested in, you don’t even realize how quickly the time passed.

I didn’t ask her out that night, but a few days later, I went back to see her. I remember this sly smile of hers, as if we saw the same possibilities in each other, the same desires. Some conversation happened, but even at 18, I was a direct, no bullshit kind of person. My exact words to her were: “I know you’re married, but I was wondering if you’d like to have an affair.”

She smirked in that way of hers. “Sure.”

We exchanged numbers and then it was clear we were off to the races, texting over the next several days. She told me she had regular sex with her husband, but it lacked any kind of passion. Instead it was like pushing a button. She said she truly cared about him, he was a good father, and she didn’t want to hurt him, or break up her family. She had never had an affair, and wasn’t looking for one, she was content with going about her life as is, especially for her son. But when I’d come back into the bar that night she knew what would happen. She hoped I would ask because she knew she couldn’t, but she also knew she couldn’t say no.

I asked if she was sure. My feelings wouldn’t be hurt if she backed out, but in response she sent me a picture of herself in the bathroom mirror. She was naked except in a thong. She had her ass on the counter and she was kind of turned away, covering herself up, and looking over her shoulder. The text said, I’m sure.

She couldn’t get away for a few days, and during that time I was a goddamn wreck. There really is such a thing as love sick. I’d never had it before, but it was like I had the flu. I was feverish, I couldn’t eat. I didn’t do much except lay in bed, watch movies, and wait to hear from her.

Also, I felt quite a bit of guilt about the situation. I mean, I’d never had an “affair” before. I was raised with a lot of high morals. My father sort of abandoned us as kids so I’d always looked down on “cheaters”. I kept wondering if I was the kind of guy who would fuck another guy’s wife. It’s not a power thing I’m really into. I don’t ever want to cause anyone pain. But simultaneously, I needed Ann. Like NEEDED her. In fact, in a weird way, it felt like we were already together, that our souls were already linked and our bodies were just trying to catch up.

Interesting note: I don’t ever remember the age difference ever coming up. I was 18, she was 29, and I had a vague understanding that we both knew that, but I don’t ever remember talking about it. It simply wasn’t a factor.

So, we decided to meet at this shitty motel, and really, it was a shitty motel. Like, the epitome of a highway stop. I got us a room and it was extremely cold. I saw her arrive in a pick up. She had made herself up a bit. Short skirt, big winter coat, underneath she wore a tight sweater with some furry frill at the neck. She kind of looked like a hooker, but fortunately that’s a look I’m into. Her thin, pale legs were unbelievably sexy.

She practically leapt on me and we kissed. One of those kisses that leaves your head buzzing. Then we just held each other in this desolate parking lot before heading inside.

The room was exactly what you’d expect. Only I didn’t anticipate how freaking freezing it was. It hadn’t occurred to me to turn on the heat earlier, so I blasted the thermostat. It was literally too cold in the room to fool around. We went into the bathroom and ran the hot water to let it steam.

While the shower was running, we both stood in the bathroom holding each other. I could feel her thin shoulders under her coat. I’ll admit I was very nervous. I’d never done anything like this before. I realized it was a big thing to do. That if I did something like this, it was going to stay with me. Looking back, we must’ve been like addicts. Just standing there knowing what we needed, knowing it was wrong, hating ourselves for it, but also not being able to help it, knowing we couldn’t stop it.

I grabbed her and we kissed with raw passion. Her lips were delicious, her small mouth and hot tongue sliding into mine. I pressed her against the door and she held her arms back, like she was giving into it. Not just sexual desire, but the stirrings of something deeper, of sadness, of thrill, of despair, of pure carnivorous hunger, of forgetting ourselves in each other.

And she felt it too. I could feel her shaking. She was scared, her breath trembling. When I looked at her I thought she might cry. But instead we simply devoured each other. In that shitty bathroom, with the steam rising in a cloud of damp heat, we just held each other as tight as we could and kissed. Her tongues sliding together. We were cleaved together, like we were trying to combine our bodies with our clothes still on. As we kissed she made these small, delicate whines, like pleas for more.

After that we didn’t care about the cold. We burst back into the main room and her coat fell to the floor. Our hands were groping all over each other. She was so slender, I could feel her ribs under her skin, her collar bone, her hip bones under her skirt. She lifted her arms and I slipped off her sweater. She wasn’t wearing a bra. So I just got my first sight of her large, round, obviously fake feeling tits. Her small pink nipples hard from the cold and desire.

I quickly dropped and tore down her skirt. She made a little “oh!” as she stood there in just her thong and heels. Kneeling before her I kissed her hips bones, her thighs, her lower stomach while she caressed my head, running her slender fingers through my hair. I pulled her close and kissed the line of her black panties. She had a wet spot between her legs and I kissed her there, over her panties, tasting the faint taste of her, smelling her sweetness.

She pulled me up to kiss her. I was still fully clothed as I moved her back and lay her on the edge of the bed. I kissed her neck, her chest, her tits. I felt the buds of her tiny nipples between my lips, rolled them with my tongue. Ann moaned, whined, breathed with such urgency. I spread her thin legs and ran my fingers over the wet spot of her panties. I could feel her pussy lips open beneath the silky black fabric. I slid my fingers under the fabric and felt her tiny shaved pussy for the first time. She felt clean, and incredibly wet. That was a thing with Ann, she got more wet than any other woman I’ve ever been with. Her pussy was simply gushing. The small petals of her opening slick and aching. When I touched her she shivered and whined.

I couldn’t take it. I pulled her to the edge of the bed where I kneeled. I pushed her thighs back, tore her panties to the side and just lapped up her pussy. I absolutely devoured her, kissing her lips with mine, tonguing her deep inside, lapping at her clit, teasing it with the tip of my tongue. She moaned so loud – writhing in such terrible pleasure I honestly thought she might start crying. But I wouldn’t stop if she had. I needed to be as deep inside her as I could. I needed to taste her, to lap up her juices, I needed to fuck her hole with my tongue. She was absolutely delicious, gyrating her hips and crying out while I held her thighs back and fucked her pussy with my mouth.

Ann didn’t want to cum yet, so she pulled me up to her face. “I need you inside me,” she panted. She tore at my clothes and I stood up and stripped. I was trying to take off my shirt when she dropped to her knees before me and desperately sucked at my cock. It was amazing. She had a very small mouth and she could only fit half of me. But I didn’t want her mouth. I wanted her pussy.

Trust me when I say I got what I wanted.

We literally fucked for hours. We couldn’t get enough of each other. I don’t know how many orgasms she had, but I had at least 5 or 6. I remember standing beside the bed, her on her back with her legs spread wide, and just pounding her pink pussy with my cock. She got on top of me and rode me like I’d never had before. I watched her, her tits out, her back arched, her eyes closed in ecstasy. Because of her fake tits, she had lost some sensation in her nipples, so she liked them pinched really, really hard. They were basically red and raw by the end of our session. I turned her over and fucked her from behind. I had her pressed up against the headboard, practically folded in half as I just let loose. I came in her mouth, in her pussy, on her ass. We’d stop and rest and hold each other in our sweat. But then she’d play with me and I’d get hard again. I had bruises all over my chest. She’d latch her mouth on my shoulder, my chest, my neck and just suck like a fucking vampire. Biting me, chewing on me. I was a bit more careful with her but she definitely left with some bruises.

One thing I remember quite clearly: she never took off her wedding ring. Not that time or the times we met after. She would be completely naked, but she always kept that ring on. It might be fucked up, but it was actually a big turn on. That wedding ring she wore, that stupid diamond that was way too big for her tiny hand, it was just this symbol of everything we shouldn’t be doing, and it was always there. I’d hold her hand while fucking her and I could feel that ring. I remember she held my face in her hands and ran her fingers through my hair. It felt so good. I closed my eyes and just felt her touch on my forehead.

When we left that day, we were both incredibly sore. We laughed about it later – how we both wanted more, but we were just too sore to handle it.

For the next several years, we would meet up whenever I was back home. Sometimes at a hotel, sometimes at her house. Her husband would go for hunting trips and I’d come over in the middle of the night and fuck her in her marital bed. She’d dress in some sexy lingerie for me – a mesh catsuit once that I’ll never forget. I would’ve happily kept it going forever, but after a few years her husband got a job on the other side of the country and they moved. We still keep in touch – we talk about once or twice per year, but it’s unlikely we’ll ever see each other again.

I honestly think this relationship made me very much who I am. It was so incredibly intense, so powerful, I guess I’ve been looking for that kind of connection ever since she left. It’s this fire that I crave. Even if I never find it again, I guess I’m just grateful that I had it.

Source: reddit.com/r/gonewildstories/comments/oadzln/my_first_affair_with_an_older_married_woman_mf

3 comments

  1. ‘Remember when’ is the lowest form of conversation. Just ask Tony Soprano :)

  2. > I’d only been gone to college a few months, but all they wanted to do was play “remember when” and I hate “remember when”.

    Damn this line hit different

    Edit: I kept reading and this is fucking beautiful writing, I mean you could send this shit to aliens and tell them that this is what it’s like to be a human being. Deadass bro you should be published, send this to the fucking new yorker

Comments are closed.