Hooked up with a MILF the same age as my mom a week before me and my girlfriend’s first date [MF]

Not much backstory to this one. I was on tinder for a long time before I met my girlfriend and one of the things I was somewhat good at was hooking up with people every once in a while. I was actually looking for serious relationships but sometimes you meet someone who just wants to fuck, and I’m not gonna say no. One of those people was a woman the same age as my mom, so over twice as old as me (I was 19 at the time). She was married and had a kid in the navy.

We started talking and things were going well, she was really easy to talk to which surprised me. We had a lot in common like similar tastes in music and the radio stations we listen to. Although we were getting along, I just couldn’t get over the fact that she was over 40 years old. I told her that I can’t exactly introduce her to my parents, and she agreed. I still wanted to do something with her, though. I’ve always had a milf fetish and she played on that really well. We talked about sex and it turned out that she was really experienced. The more she told me the more excited I got. I was imagining all the crazy things we could do because she was so open minded. Threesomes, anal, rimming… the list goes on.

We decide to go out and get some coffee first, to see what we’re like in person first. I figured it couldn’t hurt, and we went out. The date was honestly pretty awkward. I’m gonna sound like a broken record but it was like hanging out with my mom. We both kinda blanked and couldn’t find anything to talk about and the whole time I was paranoid that people were looking at us. We finish our coffee and I walk her to her car and we say our goodbyes. I kinda felt crushed because I knew she thought it was awkward as well, and it might hurt my chances.

I get home and I see a text on my phone from her, saying “I’m sorry, that was pretty bad, can I make it up to you?” My heart was racing so I asked what she had in mind and she said something along the lines of “We might not be compatible on dates, but we can still try in bed?” Needless to say I was all for it, and was over at her place the next day.

I brought condoms and she had gotten some lube. Her husband was at work so we had all day. We both agreed to try and keep it natural, so we sat down on her couch and started watching Netflix. I put my arm around her shoulders and she cuddled into me, putting her hand on my thigh. We stayed like this for a while and she said “you don’t have to be nervous”. I guess it was a little obvious. I decide to just go for it, and turned her head to face me and kissed her. She immediately turns her body to face me and we start making out. So much for natural, I guess.

A few minutes go by and she starts unbuckling my belt. I had been feeling her tits and they were by far the biggest I had been with. She zips my fly down and pulls my pants and underwear down at the same time. We had shared pictures but she still gasped when she saw my dick, then immediately started licking and stroking it. It felt awesome, she said a weakness of hers was blowjobs but I feel like that was just to make my expectations low, that way my mind would be blown. It was a smart play, because it definitely worked.

She keeps sucking for a while and I realize I’m about to cum so I pull her up to my face and we start making out again (I don’t care about dick mouth, I’m not a little bitch). She suggests we go to the bedroom and I follow her lead. Her strut was emphasized on the walk down the hallway, as if I needed more reasons to go all the way with her. We start undressing and she flops down onto the bed and spreads her legs and tells me to go down on her. I climb onto the bed and start rubbing her clit and gently fingering her. I flick my tongue across her clit and start licking up and down while my finger goes in and out slowly.

I get up and pick up the condom I left on the edge of the bed and rip it open and roll it on, she’s got her arms over her head and she’s biting her lip. She could’ve been a pornstar for all I knew. I rubbed the tip of my dick over her pussy a little bit before sliding in. She gasped loudly and I started pumping in and out. She had said she needed lube because her husband could never get her wet enough, but there was no need for us.

We switched positions about five times, from missionary to doggy style to cowgirl, reverse cowgirl, and then back to missionary. I was sweaty and tired but didn’t want it to end. She came about three times and was ready, so as soon as I felt it coming on, I pulled out and pulled the condom off and she crawled over to me and put it in her mouth. Her head bobbed up and down and I pretty much immediately came in her mouth. She moaned and spit most of it back onto my dick, but I couldn’t care less. I just laid there almost about to pass out. She giggled and crawled up next to me with her head on my chest.

We fucked one more time but after that I was done. My dick was throbbing and I had also only brought two condoms so we were out of luck anyway. She told me that she hasn’t came that many times since her honeymoon *twenty years ago*. I went home feeling amazing. I couldn’t wait to tell all my friends and brag. She sent me a text thanking me. I had never had someone thank me for fucking them silly, so that was a big ego boost. Then she said that once she came to her senses she realized that she still loved her husband, and her son, and if either of them found out I’d be screwed too. I asked what she thought we should do and she said she’d keep in touch, but that we shouldn’t do anything else for a while. I thought “fair enough” and figured I shouldn’t get tied down if we weren’t going to do anything else for a bit. That’s when I met my current girlfriend of three years.

I haven’t heard from the milf and honestly I don’t want to anymore. While it was great while it lasted, I don’t really miss hooking up with random people. I look back on it and it just feels gross. I never checked if they had STDs, and I still haven’t gotten checked. It all feels bad when I look at the life that I have now. It’s what I had wanted the whole time anyway.

Well, that’s pretty much it. I have a couple other stories from Tinder if you guys are interested. Thanks for reading, sorry it was kind of long haha.

Tl;dr Hooked up with a milf, had sex for a couple hours while her husband was at work, then came in her mouth. Went on a first date literally five days later and I’m still with her three years later. She has no idea, and never will.

Source: reddit.com/r/gonewildstories/comments/aqhs7y/hooked_up_with_a_milf_the_same_age_as_my_mom_a