[M]y first one night stand… with a mature woman

I hope this is the right place to post and that you guys enjoy the story haha!

First of all let me explain that I am not at all an outgoing ladies man or anything of the sort. In fact, I’m usually fairly quiet – not shy, but definitely not a natural flirter or anything like that. However, once I’ve had one too many drinks I often seem to think I’m a super confident pick up artist (whether I want to or not), which inevitably ends up in me making a fool of myself. Apart from the one time it actually worked.

I had recently turned 18 and had just finished a fairly long-term relationship. At this point I’d only ever been sexually active with two girls, both of which were during serious relationships, so I had absolutely no experience picking up girls or anything like that. One day, a few friends were heading out to a rock club they enjoyed and asked if I wanted to tag along. I’m not really into rock or metal, but decided I’d go too just because I was still new to clubbing and the novelty had yet to wear off. We had a few drinks at one of their houses and set off for the bar.

By the time I got to the club, I was definitely tipsy and in that state of faux-confidence. Two of my friends had gone off to find a table whilst the other went to the bathroom, with me going straight to the bar to get another drink. The queue was pretty big at this point, and I’m not particularly large or aggressive enough to just barge past, so I got stuck at the back. Turning around, I noticed a woman standing around waiting to be served too.

She was pretty hot to be honest, not my normal “type” but definitely attractive; perhaps 5’10, black hair, average built dressed in a leathery sorta goth outfit. Before I knew what I was doing I headed over to her and asked if I could get her a drink. She must have been a little taken aback, but laughed and agreed. We got our drinks after a while and I drank mine quicker than I’ve ever drank anything in my life. My memory of this point is slightly hazy, but after a while we were dancing together – my hands around her waist occasionally drifting down onto her ass, her arms around my neck. I really wish I could remember properly, but somehow we began kissing and she gave me a hickey or two.

She mentioned to me that she’d have to head home soon, and me being the drunken horny 18 year old I was decided I’d go and tell my friends I’d pulled and would see them tomorrow. They were in absolute hysterics (and haven’t let me forget it since), but ultimately cheered me on. To this day I don’t quite know if she *meant* for me to go back with her, but we got in the taxi together regardless.

We kissed a little more in the taxi, but at this point I was starting to sober up and my usual self-consciousness and social awkwardness was starting to return. Getting out of the taxi, she laughed and pulled me into her flat. It was really quite intimidating to be honest, she had skulls and candles and loads of goth stuff decorating her house. At the time I had been living in a fairly quiet area with my parents where there really wasn’t anything (or anyone) like this around, so I was starting to freak out a little, but luckily out of sheer horniness – and probably because I don’t think I’d dare explaining that I was getting a bit anxious about it – I stuck with it. She pulled me into her bedroom and onto her bed where she climbed on top of me and began to kiss me some more, undoing my jeans in the process. I was already rock hard and still in a state of disbelief, but went with it as much as I could, kissing her back and holding her waist. Slowly, she gravitated down my body until she pulled off my jeans and started sucking my cock. I was totally startled and sort of just laid there and watched awkwardly, trying desperately not to cum as she sucked.

After a few minutes she stopped and told me it was her turn, before sitting up and taking off her clothes. Like I said before, she had a pretty good body, definitely by far the hottest woman I’ve ever been with, but I was busy concentrating all my effort into not cumming or offending her. Lying down next to me, she spread her legs and gestured for me to get between them. I’d only ever eaten my ex out and was getting really worried she’d get mad at me and beat me up or something, but I sheepishly shuffled down and began licking. It was ~~probably~~ definitely not the best licking out she’d ever got, but I tried my best and I think she must have taken pity on me, and after maybe 3 minutes or so she giggled and pulled me onto my back before climbing on top of me and sliding my cock inside her.

I’d never had sex without a condom before, and had I been totally sober and not ever so slightly terrified I would definitely have gone through the whole “not without protection” speech, but didn’t seem to have much choice in the matter. She grabbed my hands and placed them on her ass, telling me lots of sexy things and clawing at my chest as she bounced on me. It took all of my strength not to cum, but after a little while she climbed off me and got back on her back with her legs in the air, telling me to give it to her like that.

Using those precious seconds to try and recharge some stamina, I got up and between her legs again, sliding my cock inside her. She began rubbing her pussy as I began to thrust, but I knew I was in trouble and about to cum any moment. I managed a few more thrusts before saying something along the lines of “I gotta cum”, to which she laughed a bit and said “don’t cum inside me, cum on me”.

Pulling out, I came on her belly. Well, more accurately, I pulled out, shot one huge load over her head and onto the headboard and pillow behind her, and then the rest ended up on her belly. Totally overwhelmed and exhausted, I collapsed onto the bed and passed out. She woke me up the next morning and offered to call me a taxi home. I was extremely embarrassed and awkward, but thanked her for letting me stay and promptly headed off home. After sleeping a little more, I woke up with a lot of messages from my friends. They’d managed to find this girl’s facebook and found out she was 34, almost double my age – and to this day they have not let me forget it. I was unbelievably embarrassed and a little worried for my health (booked an STD test the week later – came back negative thankfully) and stalked her facebook for several weeks to make sure she wasn’t pregnant, but in hindsight it was the single hottest moment of my life.

So yeah, hope you enjoyed the story! PM me if you want to know more or if you want to hear any other stories, but that was by far the most standout one. :)

Source: reddit.com/r/gonewildstories/comments/649iew/my_first_one_night_stand_with_a_mature_woman