Teen Sex Stories

18 Extremely Awkward Teen Sex Stories

A thread at r/AskReddit asked people for their most uncomfortable/funny teen sex stories, and people delivered! Here are some highlights.

If you’re like me, you were a virgin well into college. But if you were unlike me, you probably first had sex sometime in high school. Regardless, everyone remembers high school and the teen years as a hormonally insane period of life. Anxiety and interest regarding the opposite gender (or same gender, as the case may be) was astronomical, and confusing and these teen sex stories bring us all back.

1. SlamDunx

Well, one night, a girl and I were going at it pretty heavily in a parking lot after a date. While driving her home, she began giving me a little road head. I was getting really fired up and basically said “I need to fuck you.” When we got back to her house, she had decided that it was too risky to go inside, in case her parents were still awake (despite the lights being out) and she didn’t want to wait anymore. So, we decided to have some car sex. My car at the time was too small, so, we decided to go into her car, which was a midsize SUV that her dad had bought for her, or something. Right as we’re finishing up, a light goes on in her house. She panics, I panic, we start scrambling to get dressed. Somehow, we hit the alarm button on her key remote, and now, the horn is blaring every other second, the lights are flashing, and the porch light goes on. Her mom comes onto the porch as we’re trying to finish getting dressed, shut off the alarm, and make our way out the the car that we were somehow locked in. That was our last date.

2. idontbelieveyourpost

I was seventeen, 69’ing with my high school sweetheart when I heard a knock on my bedroom door. “Busy!”, I replied. My Dad ignored this reply and opened the door anyway. The end of the bed, where my girlfriend’s head (and my penis) were, was right in front of the door.
My Dad looked down to see my girlfriend with my dick in her hand, then went, “Jesus christ”, and shut the door. She promptly started crying, then left, meanwhile I’m laughing hysterically trying to console her.
He never entered my room again when I reply, “Busy!”

3. alexandergrahambell5

Accidentally FaceTimed my mom mid-act. Thankfully, she’s technologically-deficient enough to where she just held the phone up to her ear normally and kept saying “Hello?” (not seeing anything) while I frantically hit the “End Call” button about a thousand times.

4. cyph3x

My GF in high school was a year younger and never really drank. I went to a private school in another nearby state and I was heading home for the week for winter break or something. I had just bought a bottle of vodka because I had a friend there who had an ID; I was 17 so my friends and I were always hunting for alcohol because high school. this girl drank three shots en route to being completely shitfaced. she wasn’t even that small; her tolerance was just ridiculously low. she decided she wanted to have sex, which I now realize was a completely stupid idea, but I was a horny teenager. about 5 minutes in, while she is on top, I felt a warm stream coming down from my balls and that crevice between your balls and thigh. she straight up pissed on me like R. Kelly. that was an awkward weekend.

5. sarticus

She was giving me head in my bedroom and I farted. About 5 seconds later she queefed. we didn’t say anything to each other until a graduation party.

6. formerkeeper

At girlfriend’s house, her parents were out of town for vacation for a week so we thought we wouldn’t be interrupted. Her dog came in the room and licked my ass right as I came.

7. Kivulii

When I was 17, my girlfriend and I were doing it in the basement living room. Her dad walks in and gets a full-on view of us going at it pretty hard. Commence about a minute of awkward silence. He smirks, tells us to be safe, and shuts the door. As he’s walking up the stairs, I hear him call up to his wife: “Honey, he’s not gay.” That was two years ago. We broke up a few months later, and now I have a boyfriend.

8. teharchitect

I was at my girlfriends super rich/religious parent’s house around 3 AM, way later than I was supposed to have been. We were both stark naked and having some great sex. We had the TV a bit loud to mask the noise, I proceed to cum all over her tits and stomach and when I stand up to go to the bathroom and clean up I turn around and see her father in his bathrobe just glaring at me. He just witnessed me jizzing all over his daughter and seen me with my dick in my hand still dripping. That was the most awkward moment of my life!

9. jrgoode

Was having sex with my girlfriend at the time when I was 18. We were going at it, pretty hardcore. She was a Ballet dancer and god damn she had one hell of a body. Well — she is in Missionary position and I can’t even believe that these three things happened at the same damn time. My Mom knocked on the door — and I am pounding the hell out of my lady. I yell “NO” As soon as I yell that — I start to cum inside my girl- BUT I also had an insane fart that was working its way up right before I came. SO simultaneously I farted, came inside my girl, and my Mom walked in and got to see the full release in effect. My mom never walked into my room again. She texts me.

10. Ihavenocomments

My parents were headed out of town for a second honeymoon, and they left me with family friends for a week. I was 13 and they had a few kids, one of whom was a 13 year old girl. They were very liberal parents, and she was a “good” kid, plus, they thought she found me really annoying, so they weren’t watching me like a hawk. I had a crush on her, and she was very pretty. On the second night I was there, she came into my room to say goodnight to me. There was a tiny hole in her nightie, and a small part of her nipple was visible. I told her I could see her nipple. She said she was my friend, and she didnt care if her friends saw her body. I told her I didn’t believe her. She shut my door and lifted her nightie so I could see her fully exposed chest. (She still had panties on.) She said “see, I don’t mind”. I told her to come over to me. She sat down next to me on the bed and lifted her nightie. I started to touch and lick her chest. I decided to put my hand in her panties. She didnt stop me. (This is why it’s embarrassing). Her pussy was really wet. I recoiled my hand in disgust. ” it’s all wet”, I said. That’s how fucking square I was. She took her panties off and dried herself off, them she let me continue. We never had sex, but we really fooled around the rest of the week. This is as true as it gets.

11. Nightmare1990

Not myself but a friend I went to school with told us a story about him and his gf at the time trying anal. Anyway they are going at it and the gf’s mum walked into the room without knocking, he pulls out quickly and his gf liquid shits on him and the bed. He then proceeds to vomit on her. Her mum witnessed the entire ordeal from the doorway.

12. SnipSnipeAndWheel

The first time my girlfriend and I had sex (15 and 17) was on a Church’s playground right outside a La Quinta Inn. We were going at it hard, all while hoping some unsuspecting parents and children or church goer doesn’t happen upon us boning in a playground.
This was some amazing sex, so she finished at the same time I did, so I pulled out and pretty much OG Mudboned all over her stomach, vagina, as well as the playground floor.

13. phildo_baggins

I was 19 and getting it on doggystyle in my room with a girl I’d been seeing. I wasn’t wearing a rubber and she was getting really in to it and told me to come inside her. I was only too happy to oblige being a typical moron. But man, to come in a girl without a rubber, best feeling evaaar! Afterwards she leaned over to lie on her stomach and at the same time let out a massive queef/cum fart. She was totally embarrassed and jumped up to run out to the bathroom, queef jogging and shouting “omg! omg!” all the way down the hall.

14. Rhen_

Was drunk hooking up with a girl. She was giving me head, thought I was about to finish, turns out I just had to break the seal. I ended up peeing in her mouth.

15. bimmerbetch

Went over to guy friends house…go downstairs to his bedroom…he proceeds to turn on Insane Clown Posse…proceed to have sex, the whole time my mind is thinking “your fucking a Juggallo”. Wasn’t really awkward, just degrading.

16. moootz

When I was 19, I started talking to this girl on myspace. I told her I was a virgin and she said she didn’t care and wanted to fuck and all that.. So I go pick her up and we drive around for a bit. I’m nervous as fuck because I didn’t really hangout with too many girls and never did anything sexual before past kissing and touching boobs. We go to a make out-point type spot in my town and she unzips my pants and starts sucking my dick. I start laughing cause it tickled and she yelled at me.. At this point I lost my boner and it was awkward. She said she had to go home. We met up again and cuddled in her room while watching TV and she wanted to fuck me now. We both got naked and I was about to slip it in.. Then I lost my boner again, was super embarassed and just got up and left. I never spoke to that girl again, and was very depressed and had self esteem issues for years after these “first sexual experiences”.

17. 4nomalyMaC

I was coming home from a john mayer concert with my high school gf. My parents were driving us in a pt cruiser. Back then I used to always try to say nice things to girls out of the blue so I lean in and whisper to her “you look really pretty sorry I look like a slob”
The next thing I know she unzips my pants and starts blowing me right then and there. My mom talked through the whole thing and the radio was on so I dont think my parents noticed. Later I asked her why she did that shit and she thought I had said. “You look really pretty sorry but I need a blowjob”

18. cleanyourgrout

We were both virgins. I was 14 and I had been with this guy (15) that I was “in love with” for about 8 months. Neither he nor I had a way to see each other outside of church and church functions because our parents weren’t aware of our relationship. Having no place to do it at, we find a closed off area behind our church – outside – and try to do it there. I had not thought to wear attractive underwear or shave. He was just as nervous of getting caught as I was, if not more. Still, being the stupid horny teenagers we were, we try to get it on. First, he tried to just fuck me. I waited while he guided himself in and then he started trying to thrust. I was confused because I couldn’t tell if he was in or not so I (stupidly) asked, “is it in already?”. He replied with an indignant, “yes.” “Are you sure? Cuz I don’t feel anything,” I replied. But after trying to convince me that it was in, he tried to continue, his confidence shattered, adding more pressure on to him. He became flaccid and was so nervous that he couldn’t get it back up so he decides to try and eat me out. While attempting to go down on me, “you sure are hairy,” leaves his mouth without thinking. I have no clue what to say so I apologize. Seeing that this wasn’t working really well, he asks me to try this thing that he saw in a porno and to get on my hands and knees. He decided to try and give me a rim job (oddly and depressingly, this was the most pleasure I received throughout the entire escapade. After this, I gave my first blowjob ever. I had no clue what I was doing. I just tried to imitate what some porn stars did and i’ll say that I got no where close. It sucked, and not in the good way. He tried to finish by jerking off while he told me to let him cum in my mouth but he was too nervous to actually finish and he gave up. I can’t entirely remember the exact sequence of events but there was also the attempt at: *having sex against a wall (I was too heavy/he was too weak) *unsuccessful fingering (he night as well have been shaking his hand around while giving my vagina the bird) *him attempting to “help me learn how to deepthroat” in 60 seconds while surprise holding my head and thrusting til I smacked him hard enough to make him stop *me squeezing his balls to hard and causing him pain….multiple times *him attempting to fuck me in the ass but giving up because he wasn’t hard enough to actually get it in(dodged a bullet there). That was the last and only time I have ever actually gotten that close to having real sex. This was 5 years ago. Thought Catalog Logo Mark

image – Eleazar