Thought Catalog

14 Totally Random Encounters That Ended In Sex (NSFW)

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Flickr / Michael Coghlan
Flickr / Michael Coghlan
Found on AskReddit.

1. Wrong number, right timing.

Work. Phone call. Wrong number. Ask her to meet. We go out for drinks. Sex in her studio. Never to be seen again.

2. The old “Can I borrow your plunger?” trick.

Old neighbor asked if she could borrow my plunger.

3. Held a girl’s hair while she puked.

Was drunk and high at a party, held a girl’s hair while she puked. Ended up together for almost a year.

4. Fixed a girl’s computer in the dorms.

Fixed a girl’s computer in the dorms, she added me on AIM and asked if I wanted to watch a movie with her. We never watched the movie. This led to a six-month booty-call arrangement. Twas a weird point in my life.

5. Yakety Sex.

I made a stupid video in college of squirrels eating to “Yakety Sax” that went viral and it had my AIM screen name in the credits. I got a fan club and ended up penetrating a fat girl in New Jersey.

6. A girl with a violin case on a snowbound train.

There was a huge snowstorm in the Northeast and I was taking the train home to New England from NYC. The train was delayed by hours and there were no seats. I ended up sitting on the edge of a luggage rack that was four shelves tall at the end of a car. A girl with a violin case came by and we just ended up talking. Eventually she sat on the edge of the luggage rack too. After another couple of hours we lay on the luggage rack with just our feet sticking out. It had to look really weird. A conductor came by and said, “You guys look really uncomfortable. Follow me.” We followed him and he unlocked the door to one of the sleeper cars and said, “Be sure not to lock yourself out.” And you can fill in the rest of the story from here.

7. From fender-bending to mattress-pounding.

I bumped a guy with my car on the way home from the bar. I wasn’t drunk, just a shitty driver. I was only going about 5 mph so he wasn’t hurt. I got out of the car and apologized profusely and offered to drive him to his car a block away during which time he told me he had seen me around town and thought I was hot. I also recognized him; he owned a store I often walked by. I invited him back to my place and we fucked. We woke up late and he went to go open his store and I realized why he never kept his posted business hours.

8. Scoring through pantomime.

I lost my voice while out of town at a conference, and I hooked up with a young woman through pantomime, a couple of hastily scribbled notes and being a really good listener.

9. Meant to have a cigarette, ended up fucking a MILF.

I stepped outside for a cigarette and a girl who was jogging by stopped and asked to use the bathroom. She was middle-aged and attractive so I said yeah. She came out and I was watching Sex and the City (hilarious because I’m an otherwise extremely manly guy, hit the gym, work on cars for fun, order things call “the meat tornado” etc.). We got talking and I offered her a drink, she sat down and we started watching the show. We had a couple drinks and she leaned over into me and I put my arms around her. She ended up laying on me with my arm around her boobs. It got to a more risqué scene and I got a full on chub, she started moving her ass a bit. I said “hey” she looked at me with a small grin and I put my hands in her hair and started kissing her. Before long clothes are coming off and we have sex on my couch, then on my bed and then in the kitchen. We actually had a FWB thing going on for a while as she lived just a mile or so away.

tl;dr meant to have a cigarette, ended up fucking a milf

10. Motorbike spill = morning-after pill

I used to work as a bartender in Laos. One night I was dropping a girl back to hostel on my motorbike. It was raining quite heavily, and the old brakes locked up at around 35km/h and we had a light crash.

The place I was staying in was closer by and I knew I had Band-Aids, disinfectant, etc. so I took her back to my room to clean her up and one thing led to another and she ended up staying the night.

tl;dr motorbike spill = morning after pill

11. Saved a woman from a thicket of thorny bushes.

Went camping with a bunch of friends the summer after graduating from college. I arrived pretty early, got drunk off home-brewed mead, and passed out at around midnight. waking up at 3am to go take a piss, I walk out into the woods and hear faint crying and hoarse yelling in the distance. I called out and shone my phone light towards the darkness and catch the glint of someone’s eyes out of a nearby bush. To my shock and dismay, a dark-skinned girl was curled up in a thicket of thorny barberry bushes wearing nothing but a T-shirt and panties. She had turned up shortly after I passed out and was trying to find her way (drunkenly I should add) to her friend’s car which was parked about 200 yards from the campsite at the edge of the woods but here she lay cut up all over and crying her eyes out after getting stuck in a thorny thicket in total darkness. I picked her up and carried her back to the campsite, and lay her down in the back of my buddy’s truck while I treated the dozens of minor cuts. One thing led to another and by 5am she’d sobered up, we’d smoked a bowl, and I’d spent a box of Band-Aids and a condom as she thanked me generously for saving her from her situation. We hooked up a few times after that and then she moved away. Weirdest night ever.

12. An older woman messaged me on POF.

An older woman messaged me on POF and asked me if I liked mature women. I didn’t answer her question, just asked for her address.

I took a huge leap of faith but I made sure to survey the area before knocking or letting her know I was in the area. I knocked on her door, she answered in a robe with nothing under it. It was awesome. She told me to call her the next week, so I did. A guy answered so I never called her back.

It was awesome.

13. Surprise birthday present.

I was dressed as Teen Wolf, with hairy tights and suspenders for the legs. I was getting sick of getting hair around the house (house party/birthday), so I went to my room to just become, “Scott Howard.” A friend of mine had crashed on my bed (she’d slept over before), but this time me taking off those suspenders musta got her turned on, because she said, “…Well, it is your birthday…”

14. This one’s long, but it’s worth it…

Bear with me—it’s long, but I think it’s worth it.

So I have been single for a few months and was in dire need of a slump buster. There is a dive bar near me which has a target rich environment for chicks that you wouldn’t tell anyone you hooked up with. Being in need, I set the bar pretty low and had decent expectations upon leaving my abode that I would be able to come across a lady that would either weigh-in at cruiser/heavy weight or be ugly as Rosie O’Donnell but without the open scabs.

So I get to the bar and apparently everyone had the same idea that I had. There was more sausage there than a YMCA concert and every fat chick had 2-3 dudes hitting on her. It was like all these chicks woke up as 2’s and were 7-8’s when they hit the bar. I am trying to decide if I should just leave and go home and fap to the new Sears catalog, I saddle up at the bar and order a beer. Shortly after the urine that they call beer arrives, this female octogenarian sits next to me and asks me why I look “Pissed off”. I told her how there was a lot of hog in the bar so I was grabbing a drink before I went back home. So we chat for a bit and she’s buying me beer so I say “fuck it” at least I am getting to drink for free. I listen to her yap on as women are wont to do for an hour or two and keep checking out the lady population.

The parking lot is emptying and ladies are starting to disappear as guys stuff oversized women into their cars and ride back to their places with the car tilted at 45 degrees and smelling of cheerios and broken dreams. Meanwhile I am talking to a lady who likely voted for FDR. I finally decide, after about 6 free beers and a shot, that I am heading home to get the Vaseline and rubber spatula out for a night of solo action. I get up to go and I am a tad dizzy (since I’m a bitch and don’t drink much) and start my sad walk home. Grandma tells me that she lives close by and it would be nice if I walked her to her door. Being the gentlemen that I am I said “fuck that shit, its cold outside” so she said she would just follow me as long as we were going to same direction….fine whatever. So once again I have to listen to her drone on about the price of Ensure or some shit until I reach my apartment complex.

I mumble something like good night or rest in peace and head up to my place. I get to my door put the keys in the door and this bitch had followed me. I turn to her and I’m like listen I just want to have a fap and go to bed. Apparently that romantic statement was what she was looking for because she grabbed my junk like a death row inmate getting their last supper and said “why don’t I do it for you”. So like all men I make a bad decision, a thousand things go through my mind and the last one was “well at least you’re not doing it yourself.”

So we head into my place I sit on my nasty couch and I yank out the purple-headed warrior which is 100% limp at this point. Grandma goes after it like a hungry dog on a meaty bone and is giving me some serious grade A head. I’m starting to think I made the right choice here and begin thinking of ways to tell her to get the hell out after I give her an FDA approved dosage of DNApudding. While this is running through my mind apparently grandma was doing some ninja shit because before I know it she got her pants off and starting to remove her shirt. Ok forget what I said, this was a bad idea and the look of her half naked body is making me go limp.

Granny tells me that she is going to need some attention and that if I liked what I got earlier I would love what her “kitten” had for me. So I’m half limp and the functioning part of my brain is like “ok she did give good head, fuck it lets see what it’s all about”. So she sits down on the couch and saddles her hips up to the edge as I try to furiously stuff my mostly limp self into a condom. I manage to make things work and slowly slide things in, and it’s surprisingly pleasant. It’s like putting your dick in a glass of warm pudding. I slowly go about my business, I start questioning my life choices that brought me to this point. I am getting lost in my thoughts when Eleanor Roosevelt whispers something in my ear that will haunt my very dreams. If I wanted to be fucked like an old lady I would have fucked an old man.

This should have been the straw that broke the camel’s back and I should have just sucked up the ego hit and kicked her ass out. Instead, I felt the need to defend my manly honor and started pile driving granny’s roast beef box like the undertaker at WrestleMania. At this point I am trying to find my focus so I can get mine and get it over with but my ability to orgasm is being hindered by the fact that A) I might have broken her hips and B) she’s hooting and hollering like she just won the showcase showdown.

As a testament to my depravity I did manage to fire one off while grabbing her breasts that probably suckled kids from the great depression. After that it was a haze of her getting dressed and me thinking (as I passed out) that I hope I didn’t remember what I had done. Which sadly is not the case. TC mark

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