Hi all, long time lurker and thought I should finally contribute. I tend to enjoy the more casual stories around here (ONS, etc) so this kind of fits into that group.
This happened a couple of years ago. I was in my early 30’s and had moved across the country a few years earlier but friends and family were still on the west coast so I would visit frequently. On one of those visits I stayed with my good friend Alex. Alex lived in a 2 bedroom apartment with a rando he had found on Craigslist named Molly. Molly was very cute – 5’5”, long blonde hair, fair complexion and fit, with very large tits that she did a good job of hiding.
Being the wonderful friend that I am, I made Alex and a few of our other friends go out day drinking to celebrate my being in town (never mind that I was in town just about every month and saw everyone pretty regularly). We do some bar hopping and next thing you know it’s pretty late and we’re pretty drunk so we say goodbye to our friends and Alex and I head back to his place. When we get back to his place Molly is there, so I have the wonderful idea of convincing her to go out and get drinks with me – the last thing I needed at this point was more drinks. So we do that, one things leads and we end up back in Molly’s bed – but this story is not about this night. Honestly, we had some very brief half-assed vanilla sex in the morning because she had to leave early for some family stuff.
Fast forward 2 years later. I’m back in town, thinking about who I could booty call that night. A couple of my fwbs had started getting complicated (feelings, needs, etc etc) and I did think that juice was worth the squeeze. I hadn’t seen or communicated with Molly since that day but I thought I’d shoot her a text and see if she was interested. Lo and behold – she was so we made plans to get drinks that night.
She was no longer living with Alex and because of my plans for the night, I was staying in a hotel. We met at a nearby bar and had a couple of drinks. Thankfully she looked the exact same as a couple years earlier – you never know with these things. She was wearing a cute floral that still somehow managed to hid her DDs.
Things actually weren’t going as well as I had hoped. I had hoped that drinks were a mere formality before a romping night of sex – but it did not feel like it was going that way. When it got to the end of the night, she assumed I was heading back to say with Alex. When I told her I had a hotel room nearby – her entire attitude changed. She had apparently thought that this was just drinks and that we didn’t really have a place to go afterward. Crisis averted!! Shame on me for not making that much clearer earlier in the night.
So we go up to the room. As soon as we walk in the door, I push her up against the wall and start making out. After a couple mins of that, I reach down under her dress to insert my finger in her pussy and I can feel how wet she is already – she might have wanted this as much as I did. We continue to make out and I start to finger her. She’s doing that thing where we’re making out but then she has to break away in order to audibly moan. From there, I continue to undress her. Now she’s completely naked and I’m still fully clothed while I continue to also finger her as she’s pressed up against the wall. She now also notices this clothing injustice and takes off my shirt and starts to push me back towards the bed. I lay down and she and I work together to take off my pants and underwear. I’m completely hard at this point and finally naked.
She immediately deepthroats me. Now, I’ve got a good amount of experience and not once before or since has anyone deepthroated me with such ease. I still don’t quite understand the physics of how it happened but it was breathtaking (and dare I say a bit intimidating). She continues to blow me for a couple of mins while I try and push her head down and gag her to little effect. She then starts licking my balls. I’m always one for pushing boundaries so, I push her head down a little farther and pull my legs back and she goes to town rimming me – no hesitation. After a few mins of that, I figure we should really start pushing the envelope. I grab her by the hair and drag her across the room and put her on her knees against the wall – where I get to fucking her face very hard. She appears to be loving it and things are starting to get a little messy with the tears and the drool. I stop for a minute and start to finger her again and she just gushes immediately. “That’s the first time that’s ever happened” she said (I’m sure ;)). After a few more minutes of figuring i get her back on the bed and go down on her and then also rim her for a while, which she also seems to enjoy quite a bit. She’s making a lot of loud moaning noises until she finally cums again.
Now its time for some piv. I was preface this by saying that we did not practice safe sex. We started with missionary and then pretty quickly switched to doggy. She seemed to really enjoy doggy, moaning some and saying “You make me feel so good” – which I honestly didn’t love in terms of dirty talk, but oh well. So, one more boundary to test. I put my thumb in her ass. She seems to like that as I keep pumping her in doggy. Then I pull out and start to try anal and tell her “I’m going to put it in your ass”. This was met with a firm “No, I don’t like that”, so back to doggy it was. I then flip her over and put her legs over my shoulders and fuck her very hard and start to choke her. I’m getting close and I tell her “I’m going to cum all over your face” which was met with a “Yes please”. I pull out at the last second and shoot a big load all over her face, which she then proceeds to lick up with her fingers. We are totally sweaty at this point and pretty exhausted. We take a break and then fuck a few more times that night (I came on her face each time). She has to leave early in the morning (again!!). Haven’t seen or spoken to her since.
Source: reddit.com/r/gonewildstories/comments/c7jgde/mf_hooking_up_with_my_friends_old_roommate