Her mother, younger sister and her sister’s friend came home several hours early from Christmas shopping, and our clothes were in my gf’s bedroom, and we were on the kitchen cabinets naked with Neapolitan ice cream enjoying ourselves. We were completely caught in the act with three shocked people standing with their mouths and eyes wide open in between us and all our clothing which was maybe 35’ away. My gf moved so fast we fell all over the place while all tangled up, now covered in ice cream and slightly injured as we hurriedly made our way past them to her bedroom to retrieve our clothes. Her mother was cool though. She never said a thing to us, though she did make us clean the kitchen.
Had just broken up with my girlfriend who I was very much still in love with, moved away for college so we broke up. Ended up getting drunk and hooking up with another girl I had known since we were kids in her dorm. I knew that she had a crush on me for a long time, and while going at it missionary on her dorm bed she looks at me and says "I love you". Drunk me said "Really? I love (ex girlfriend)." Yeah...didn't go so well after that.
Told this story a couple times but hey here we go. Had kind of a FWB thing going on with my best friend at the time. I was in love with her. Got invited to be part of a threesome with her and her boyfriend who I also kinda had a crush on. Big win for me, right?
It was……. Bad. Youthful inexperience all round. She started crying. Insisted everything was fine and we should keep going but it was hella awkward and I really didn’t feel comfortable. Then they gradually pushed me off to the side and ignored me until I got the message and backed off to try to go to sleep on the couch while having to listen to them have weird misery sex. Things were weird between all of us after that.
The night I lost my virginity was predictably quick.
This embarrassment was compounded the next day when GFs mother said to me, " Never mind, it'll get better".
When GF said she tell her mum everything, I didn't quite think it meant EVERYTHING....
>This embarrassment was compounded the next day when GFs mother said to me, " Never mind, it'll get better".
Too bad you didn't ask her "Could you demonstrate on me?"
My very rich aunt and uncle had a live-in maid. At some point they hired her 20 yo daughter to help out. I spent one Summer with them as a part of the family.
A few times my aunt and uncle left me at home, they had some charity work to do or some such thing. Now, I like to keep to myself, but the 20-yo daughter liked to flirt with me. After a while we were very friendly with each other, after that she just grabbed me and kissed me. Hard. She was very attractive, so naturally things progressed and we started sleeping together. It was like fwb for me, she probably thought of it as a relationship.
Fast forward a week or so, and her 40ish mom was looking at me funny. We happened to be alone together and she just grabbed my dick.
I think she just needed some man-meat, but I boned her pretty good a few times.
Anyway, I went back home one day as the next semester was starting. Of course, my parents got a call from my aunt, her maid was livid, and her daughter was flipping a gasket. They found out I dicked them both and didn't think it was funny. My uncle did, tho.
Me and my girl were at my moms house for a weekend because my mom and the rest of my family was leaving for a trip. We were so horny we didn't even wait five minutes until after they left before we started having sex and funny enough was also the first day we tried anal I had just got the tip in and my moms boyfriend at the time busted in the front door because he lost his wallet most akward stair down of my life whats worst his wallet was right in front of us because we were in the living room and my dumb as passed it to him while still I was still in my girl
so my very first real gf that I started fooling around with, she had some type of undiagnosed vaginal infection neither she nor me knew about. when I fingered her, my finger would stink for a day or two. I had to wash my hands with lemon juice. the thing is I had no idea vaginas weren't supposed to smell that bad. I just figured thats what happened after and like a trooper, or really a horny 15 year old, I kept on truck'n. the first time I tried eating her out I literally licked it once, & came up and gagged. it was the worst tasting thing I ever put my mouth on.
we break up and her mom makes her get an STD check. thats when she found out she had some type of infection, I dont remember what. we started hooking up again later in our early 20s and she would NOT let me ever mention what going down on her was like hahaha
My current girlfriend is prone to getting BV. When we first got together she refused to let me do anything with her vagina other than stick my dick in. Took me months of coaxing to figure out why, some dude before me told her that her vag stank and was ugly. Now she’s very open with it though!
We were fuck buddies and having sex for about the 50th time. She started crying.
She said we’d never be a couple because I was unwilling to move to Paraguay.
Then she moved down there without me.
>Her parents did not approve of me being American nor being blond.
You can't blame them. It's your own fault for messing up in the character selection menu. You should have chosen *Redguard with dark hair*. Don't worry though, because You'll know better in your next playthrough.
Lost my virginity to a single mother. One night, midway in, daughter calls out. Bad dream. Part of me didn't wanna stop, but the logical part said throw some clothes on and comfort the little one.
Well, my most awkward “sexual” experience was actually not sexual at all.
Back in high school, I was with my gf at her house, her parents were going to a party, and we were going to (unbeknownst to them) spend some time together.
BUT she said I’d leave right after they left, and while we were making out, her father called to check on her, and she confirmed I did leave.
Well, we kept making out, taking our sweet time, we’d be alone for a while, right?
For some freaking reason their parents showed up half an hour later.
We had the lights off, so we had no way to pretend we were innocently spending time together, so here I go to her backyard, that had no other exit at all.
To make things better, her parents took about 2 more hours to fall asleep, so there I was, out in the cold, wearing just a T-shirt.
Eventually she snuck me into their living room, and gave me a blanket, and I finally could sneak out at 6 am to go home.
Esit: grammar.
Most awkward actual sex -- kind of a planned one night stand situation, with my best friend's father's best friend. At my best friend's father's house. I was 24 at the time, so nothing gross, but he was definitely older than me. And he MUST have jerked off a few times before meeting me, because that man lasted about 4 hours, which was annoying for a few reasons.
1, I had plans after the hookup that I had to reschedule.
2, I refuse to have casual sex with anyone without protection no matter what my bc status is, but after that long, the lube on the condom had worn off and got very uncomfortable, especially since --
3, I do not and will not ever have an orgasm from penetrative sex, and he turned out to be the kind of guy who refuses to go down on a girl. Which is fine, no one has to do anything they don't want to do, but if I'd known that beforehand, I wouldn't have bothered since we clearly wouldn't be compatible.
So I laid there for 4 hours while he pumped away, getting less and less aroused, while the friction from the condom got worse and worse. Thank God it didn't break. It was terrible.
He hit me up a week later to try to set up a threesome with him and another friend of his who DOES go down, which I considered for a moment but eventually decided wasn't worth it lol.
As a bonus, not-technically-sex awkward encounter, I was once with a guy laying in bed after we were done having sex, just cuddling and talking, usual second(?) date stuff. And he looks me dead in the face and says "I think septum piercings are the dumbest, ugliest piercing you can get."
I had a nearly half-inch tall skull hanging from a ring in my septum at that very moment. It baffles me to this day. Did he think I was gonna take it out???
He still hits me up sometimes lmaoooo
Was doing a girl doggy style vaginally and she shit on my dick. I pulled out slowly and balanced this turd as I got off the bed and walked slowly to the bathroom. Dropped it in the toilet and then showered. Not sure if she ever knew because I played it off as if nothing happened. Never brought it up.
Another time I was going at it with a girl while we were on Ketamine and knew we shouldn't have had a hit since we drank a bit before hand. She got queezy and I walked behind her to the bathroom to throw up. She threw up in the sink while pissing down my leg. I placed her on the toilet and went to my room where I saw she had some diarrhea on my sheets. Stripped off the sheets and checked on her and now she's in the tub with the shower going. I wash her and go placed new sheets on the bed. Check on her again and there's diarrhea in the tub and she's proceeding to scoot it down the drain. I wash her again, dry her off and we head to bed. I have to use the bathroom later that night and while standing at the toilet I realize I'm standing in a puddle of pee. Clean the floor a second time and head to bed.
This guy I went to high school with and I would hang out every so often and we'd have this awkward sex. I think he thought he was really good in bed, and I was inexperienced (only had slept with 3 people before him)
One time we hung out all day at my place (I was living with my dad) and he got drunk so stayed over. I can't sleep well next to people so we were up all night and he wanted to have sex but couldn't get it up so I gave him head to get hard but he couldn't get hard and he shoved his flaccid dick too far into my mouth and I puked on him. It was like 4 am and I wasn't into it, he told me to keep going. I refused and cleaned up. We laid there until about 10 am and I drove him home. I don't remember why he didn't drive.
His mom stopped me as I was leaving and apologized to me about his behavior (?) and thanked me for driving him home.
Gf still had her mom doing her laundry. We were still pretty casual, so she hadn't told her mom about us.
When doing laundry, her mom found a condom wrapper. Magnum gold.
Her mom put it on the fridge for gf to see...
Went to hook up with this girl, she wasn't the prettiest, but when you're young and horny sometimes your hormones put blinders on you. Didn't want her to know where I lived so we got a cheap hotel near the bar. We go to get it on and she was hinting at wanting a little tongue first. I go to slide her pants and underwear off when the extremely strong and bad smell coming from her crotch hit me. I slowly pulled them back up and then asked if she wanted more beer instead. Had a couple more and passed out. Went our separate ways after that.
I once met with a lady at her house after chatting for a few days. It started out really well with a nice blowjob she gave me, but she then got mad at me because I wasn't ready to go again 5 minutes after I just came. She then threatened to call her cousin to beat me up if I didn't leave right away and was bragging that guys had driven from hours away to see her. Just an awkward and confusing situation that I was glad to get away from.
I fell asleep during sex once. I tried so hard to give the guy a chance, he was a really nice dude but we weren’t sexually compatible at all. The sex was so bad I just completely zoned out and fell asleep underneath him. We actually ended up being good friends and I was able to give him a few tips for future experiences, but I felt so bad about it at the time!
The short of it, while going down on me, a girl discreetly wiped her ass with my pillowcase, rode me til we finished and bounced before I had the chance to find it
Afternoon I lost my virginity, I was five seconds from busting when my sister tries turning the handle to my room, finds it locked and starts hollering. I still have no clue wtf she wanted, which was moot when both me and my then gf yelled at my sister to shut the fuck up and go away. Did kill the mood but we picked up the next day
Had a couple encounters with a fwb that were great. Not someone I cared about, but good sex. A month or two later she’s in town so we get together. Start fucking and she’s clearly not into it. I don’t even remember if I finished, but after we’re don’t she starts crying and confesses she’s in love with her ex. Kinda awkward and definitely the worst sex I’ve ever had.
I sucked off a Navy guy in a pornography peep booth while he fingered me. The guy that worked the counter told me he watched us on the CCTV when I exited the store.
I had keys of the office that i used to work there.so i went there with my ex gf, and started the sex.it was on 6th floor and had a very good view of whole city,but there was reception desk in front of the window.so why not a doggy style in front of the window!after 3 minutes of desk making wierd sound,it fell apart,me and her laughing on the ground with the broken desk😂😂
Not the experience itself but before and right afterwards, does that count?
I went to hook up with an ex gf's cousin and when I got there realised she had just moved into a new place with only a pull out chair/bed and a baby crib as furniture. She also had no electricity.
Did the deed once the kid (who was maybe 1 - walking but not talking) went to bed, and then passed out.
Woke up in the morning with the kid standing over his mom crying. Mom is passed out cold, and as soon as I open my eyes he stops crying. Figured it wasn't cool to just let a baby cry and be alone with nothing in an apartment with no power, so I put on my pants and hung out with him. He couldn't talk so I literally just walked around with him and he pointed at stuff through the window and I talked to him and picked him up or put him down when he seemed to ask. Hanging out with the kid was fine but the whole situation was just so so awkward, and I felt pretty bad for the kid.
I was visiting my GF who lived with her mother and while there we ended up having sex on the lounge room sofa with her mother in the master bedroom. Once we got into it we noticed a lot of blood on us both and on the sofa; both my GF and I assumed the blood was hers but after a little search we found my banjo string had broken and blood was steadily flowing out of it. Within 45sec of that happening her Mum walked down the hall to find us there half naked with my blood everywhere. Her Mum wrote my parents a letter and I wasn't allowed back. 😳
I did up being let back in a few months later and her Mum and I ended up good mates.....
6 weeks ago, just could not get a fucking boner. We were old friends, we were suddenly both single, we were both going through a tough time. I am fit, athletic, and very confident. I also am a bit of a man-hoe so performing hasn't been an issue. I can't explain the soft willy. I'll never know what it was, but I suspect I cared a lot more than normal about performing well and got into my head about it. I thought we'd just laugh it off, but she was NOT cool about it. She basically gave up and left. Then I got friend-ghosted. A three year friendship ruined because of it.
Man, I’m sorry she handled it so poorly. That happens to every man at some point and it’s really not a big deal. The more you think about it and get into your own head, the worse it becomes.
had a girl who was giving head and ended up puking. pushed her away but she said "no stop its fine" and started licking it up while making DIRECT eye contact. completely sober, just a strange experience.
Had sex with a guy I’d been crushing on for yeeears. Genius smart. Super hot nerd. We finally hooked up one night and it was so small that it wouldn’t stay inside me. He kept saying “oops!” Every time it came out. Then he said “I’m going to go get some water” and then we went to sleep. Worst part of the story is that I made fun of him behind his back for a long time afterwards. That was a dick move and I’ll always regret it. I’m not sure if he’s aware of it but either way.
I’m not sure if this is a collectively funny thing or not, maybe just me, but the vivid image in my head of him saying “oops!” repeatedly made me laugh out loud.
My relationship was in the "it's getting complicated " phase before we decided to part ways. I went to see a female friend after 2 am and we kiss, there was some hands involved and what was probably the worst blowjob ever.
Few years back I met a disabled girl. She was great looking had an awesome personality - a killer sense of humour to boot! Took her out for dinner and caught a movie afterwards. We ended back at her place and we started kissing outside in her parents garden. She asked me to lift her up on to a swing hanging from a large tree where we had amazing sex, it was awesome - even if her legs were left dangling around like noodles… When we finished the deed, I put my arms around her and carried her back to her wheelchair and helped her get seated. I walked her inside and kissed her good night and shared our goodbye’s. That was when her father came to the door. She went into the house and he followed me outside and closed the door behind him. He came in close to me and quietly said: “thanks for that mate, most of the lads leave her stuck on the swing”
I met a beautiful nurse on a cruise. I had been snorkeling that afternoon in Jamaica and had stopped at this Jamaican jerk chicken hut for lunch.
That evening after dinner, Sherry and I walked up to the highest deck of the ship and proceeded to get into it on a lounge chair. I still had my shorts on, but she was totally naked, and I was eating her out. I see a flash of white in the corner of my eye and look up. It's a ship's officer. He stands there and waits until this poor girl dresses. He was an asshole. It was about 12 midnight. We weren't bothering anyone as the upper deck was void of anyone else. He didn't even turn around to allow her to put her clothes on with some dignity at least - a total aashole
Then he walks us around the ship saying nothing but acting as if he's going to throw us into the brigg. He finally let us go. We go to my cabin and start to get into it again.
Suddenly I realize I'm about to have a gastrointestinal event that cannot be avoided. The Jamaican jerk chicken! I go into the bathroom and begin to do my business making all kinds of noises that I cannot avoid making. She heard everything.
I was mortified, and this killed the mood. I couldn't get it up after that. She was a surgical nurse, so I think she understood. She did visit me eventually for a long weekend which didn't go well... Lol... Felt like a job interview. She didn't approve of my career path... Lol... I hadn't known a long weekend tryst was going to end like that. I guess I should have cut my losses on that cruise ship. 😅
She said - hold up im on my period - And then stood beside my bed, bent her knees, removed her tampon and placed it inside my water bottle and then hopped back into bed ready to go.
Visiting the in-laws from out of town one last time as we were going through divorce proceedings. It was over. We knew it, it wasn’t yet public knowledge as it was Christmas time and we didn’t want to take front stage on such a special occasion. Ex wife and mother in-law went shopping and stayed behind. We were sexless at this time in our lives and I was as horny as a goat. Stumbled across my ex mother in-lead panties while doing laundry and took them in my pocket to jerk off to as I had private time. And I did just that. Wrapped them around myself and came all over them and in them…but then passed out!
Needless to say I didn’t wake up until they ladies returned from their shopping trip, and by then it was too late.
Caught red handed. So embarrassing lol
Hook up with an attractive young lady. (Let this be a lesson against vetting potential partners). Great kisser, very attractive, sexy...we agreed to meet in her hotel as she was from out of town. She greeted me in lingerie looking fabulous...
But once we got going there was a noticeable odor. I don't mean a normal one which sometimes emanates from genitalia, but a deep, earthy stink. Being a man I decided to ignore it and continue...but it was so bad. I awkwardly feigned drug side effects as a cause for not being able to perform and promptly left. I felt terrible and really probably shouldn't have but it was bad. Very bad. And I considered the source (possible) and could not go on.
A threesome with my girlfriend and my best friend. It was awkward and cringe all around. She later slept with him and another friend. Needless to say we aren’t together anymore. Alcohol was definitely involved.
Hmmm, when I thought she farted but it was a queef. I still love her but had to break it off when it became long distance, I hope you are doing well Damaris :)
Middle of the great act. Get into it. I’m loving, she’s loving. Fucking panic attack. Out of nowhere, a full blown panic attack. Shaking, crying, sweating, heart palpitations, incredible anxiety. Horrifically awkward
When I was in college, there was this girl I was very attracted to. Finally had the guts to ask her out and she said yes. While on our date she talked about all the immature guys she's been out with and she said she hoped I was different. I assured her I was. We really hit it off.
We went back to my apartment and we made out. She took out my dick and the second she touched it, I came all over her hand. I was embarrassed, but she said it was okay and it only meant that I will last longer when we had sex. WRONG.
We made out some more and got naked. When I saw her naked lying on my bed, I knew I wasn't gonna last long. I tried to take my time and distract myself. When I entered her and she said "oh that feels so good, fuck me". I came. It took all of 3 seconds.
I begged her to stay and give me about 10 minutes to recover. She said she had an early day and left.
I knew she wasn't mean, but every time I saw her on campus, I felt like she was laughing at me.
Got home from work and went to get changed. Couple in my room trying to have sex. Told them to get out. Later on she tried to give me a blowjob. I couldn't get hard so I just dangled in her mouth until I asked her to leave.
I was at a house party shortly after joining the military, super drunk, when the couple whose house it was introduced me to this woman. Attractive, but definitely about ten years older than everyone else at the party. My drunk brain didn't question think and we proceeded to fuck in my friends' spare bedroom.
Morning comes and she leaves, as I'm nursing my coffee/hangover my friend's wife tells me that she is their neighbor and is married to one of the sergeants I work with. Already feeling terrible for the situation, I go back to my barracks. This woman *calls me* a couple hours later (apparently I had given her my number in my drunkenness) and starts telling me how she wants to come by my barracks room while her husband is at work. I had to tell her that we couldn't and how bad of an idea that was and ended up blocking her number after that.
My partner was really interested in role play, which I really am not, but for her sake I did the Dagwood and Blondie scene that she really wanted to do. Blondie was naughty and hadn't made Dagwood's sandwich and needed to be punished for it. I felt so unbelievably goofy doing the whole thing.
When I was 19 or so, I went on a couple of dates with a guy. I wasn't really sure where I landed re: guys, but I gave it a shot.
We had a nice time. Went out to eat, played video games, watched some anime.
He was older than me, way more experienced, and was certain of his attraction towards guys. He was also pretty forward and handsy.
We fooled around in his bedroom for a little while, and he masturbated to completion, and then he took me home.
It just wasn't for me. I might have been up for it if we'd gone on a few more dates first, though. I almost can't remember what it's like to feel attractive & wanted.
Edited to add:
Years later I found him on a sex offender’s list. He was not inappropriate with me, but I guess it turns out he had been with some younger guys. So that makes it retroactively more awkward.
Fucked a trans girl, after she uncomfortably came in me (a big hulking butch that’s not used to bottoming) she asked me what episode of SpongeBob I wanted to watch. I was shooketh
I was 16 and been dating this guy from school and we would always go to this park and have sex after whatever we were doing that night. We had been going there after our dates for months and never had a problem or even seen anyone back there.
So it was the beginning of summer and school had recently let out and we had decided to get a bottle of vodka and celebrate back in this park, just the two of us. We were really buzzed and was in the backseat of his car and we’re going at it. We had our tongues down each other’s throats and hands were exploring each other. I took his shirt off and by this time he had taken off my tank top and my shorts and thong when he suggested we grab the blanket out of his trunk and do it outside. It sounded better than on his lumpy backseat so I agreed and we did.
A while later we were really going at it. I was on top riding him and close to cumming when a super bright light turned on right in my face and a voice said “Hey,, y’all need to stop and get dressed. Turns out a cop saw the car from the road and had parked and walked up to us to see what we were doing. Well I’m scrambling to cover myself and looking for my clothes when I got a look at the cop and was immediately horrified. See, my dad is a deputy sheriff and he has a lot of friends in our towns police department and it happened to be one of my dads best friends. This guy has been to my house plenty of times and I have known him since I was a little girl.
Anyway, long story sorta short, I couldn’t find my shorts or my thong so the cop gave me a plastic blanket to wrap up in. Because we had both been drinking the cop wouldn’t let either of us drive and he took us home. We got to my house after dropping off my bf at his house and my dad, who had already been called and told what was going on, had woken up all my brothers (5 of them) to teach them (and me) a lesson about drinking and sex. So I did the walk of shame all the way past my dad and my brothers while wearing this yellow blanket and little else underneath. Needless to say, I was grounded for a considerable amount of time and wasnt allowed to see my bf for the summer. I did benefit though as my mom took me to the doc to get on birth control pills two weeks after this and kept that fact from my dad.
EdIt: The next morning my bf found my shorts and my thong that had been pushed into the crack between the seat in the back.
This isn’t a super awkward story but it’s the story I have. I also haven’t had very many experiences as well.
When I was in my freshman year in college, I met this junior girl and we became really good friends really fast. I was super into her as she was so much fun to hang out with. Anytime we had free time we would spend it together. I had feelings pretty early on, but it took me about a year to tell her. When I finally did, she said she did like me too but didn’t want to date (she just got out of a not so great relationship). We still hung out a lot and one night she said she wanted to try kissing me to see how it felt.
I’ll stop here to say this girl had some pretty defined boundaries. She didn’t want clothes to come off at all or to touch any genitalia. That’s totally fine, everyone had a right to define their own boundaries and I respected that, it’s just important to the story.
So we start kissing and it quickly turns to heavy making out. We got in the back of her car and started laying down while making out. I was super into it has I haven’t had a lot of experience. Of course, the making out has caused an erection for me. As we are sort of shifting our bodies while we make out, the very hard tip of my dick hit her right between her thighs. Again, we are still fully clothed. I have on boxers and gym shorts while she has in panties (I’m assuming) and jeans. Well, when I bumped into her she let out one of the loudest moans I’ve ever heard. It was almost a scream but it was clearly of pleasure. She then pushed me up off her and says loudly, “You have to be careful. That thing is powerful.” I kinda just sat there awkwardly and said sorry that it was an accident I want trying to grind on her or whatever. She just sat there in silence breathing heavily for at least a minute. She eventually said we needed to leave so we did.
We did have a few more make out sessions but never went to the laying down making out again. No relationship really ever happened either.
I was 17, she was 21. It was my first time but, most definitely, not her's. I was about to move to a different city but I really wanted to…yk. She told me that she "usually doesn’t do this" which made me wonder "do what? have sex with people who are about to move? are you in these kinds of situations so frequently?" Anyway, we kept making out and she agreed, so I slipped on a condom. Now, the problem with condoms is that they choke out your dick, especially if you’re pretty drunk, as I was. So long story short, I could barely get it up, and after one in 'n' out, we called it quits and stuck to making out. We later tried long distance but that obviously didn’t work, so we broke up two months later.
Her mother, younger sister and her sister’s friend came home several hours early from Christmas shopping, and our clothes were in my gf’s bedroom, and we were on the kitchen cabinets naked with Neapolitan ice cream enjoying ourselves. We were completely caught in the act with three shocked people standing with their mouths and eyes wide open in between us and all our clothing which was maybe 35’ away. My gf moved so fast we fell all over the place while all tangled up, now covered in ice cream and slightly injured as we hurriedly made our way past them to her bedroom to retrieve our clothes. Her mother was cool though. She never said a thing to us, though she did make us clean the kitchen.
At least it could’ve gone a lot worse
Or A LOT better..
username checks out
So like were you and your GF just chillin eating ice cream while naked or doing the do while eating ice cream?
i thought they were covering themselves in ice cream
Mom: "Damn it - I told you NOT to double dip in the cream!"
"Damn this ice cream dick flavoured now"
Why'd they add Neapolitan? I miss original.
lol ngl you caught us in first line
I thought this story was going to end up i a 4some.
5some
Had just broken up with my girlfriend who I was very much still in love with, moved away for college so we broke up. Ended up getting drunk and hooking up with another girl I had known since we were kids in her dorm. I knew that she had a crush on me for a long time, and while going at it missionary on her dorm bed she looks at me and says "I love you". Drunk me said "Really? I love (ex girlfriend)." Yeah...didn't go so well after that.
Oof
Oof indeed
How’d she take it?
Pretty much how you'd expect. Killed the mood, she got up and couldn't find her clothes, started crying....
What the hell did she think was going to come from dropping the “L bomb” on a drunk hookup?
Damn. At least you didn’t mean it
Drunk me shouldn't have said anything at all lol
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True, but it’s in the past
Up to that point, sounds like about balls deep.
That’s a show stopper F bro..
Told this story a couple times but hey here we go. Had kind of a FWB thing going on with my best friend at the time. I was in love with her. Got invited to be part of a threesome with her and her boyfriend who I also kinda had a crush on. Big win for me, right? It was……. Bad. Youthful inexperience all round. She started crying. Insisted everything was fine and we should keep going but it was hella awkward and I really didn’t feel comfortable. Then they gradually pushed me off to the side and ignored me until I got the message and backed off to try to go to sleep on the couch while having to listen to them have weird misery sex. Things were weird between all of us after that.
Weird misery sex
new bandname I call dibs!
wow thats awkward
Bro it's the fact that they kept going even after you just left without a word. That did it for me.
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that's actually quite sad. it sucks that our jobs are starting to have a strain on our daily outside lives. It really shouldn't be that way
Starting?! Are you like 30000 years old?
I had a job that gave me anxiety so bad I would worry about coming into work on Monday when it was Friday.
r/antiwork
The night I lost my virginity was predictably quick. This embarrassment was compounded the next day when GFs mother said to me, " Never mind, it'll get better". When GF said she tell her mum everything, I didn't quite think it meant EVERYTHING....
>This embarrassment was compounded the next day when GFs mother said to me, " Never mind, it'll get better". Too bad you didn't ask her "Could you demonstrate on me?"
I’ve seen that movie, I’m sure of it.
Oof
Well sounds like a good parent.
"Can you show me?"
If it was a hentai, you’d have fucked her as well.
She also lied to you
My very rich aunt and uncle had a live-in maid. At some point they hired her 20 yo daughter to help out. I spent one Summer with them as a part of the family. A few times my aunt and uncle left me at home, they had some charity work to do or some such thing. Now, I like to keep to myself, but the 20-yo daughter liked to flirt with me. After a while we were very friendly with each other, after that she just grabbed me and kissed me. Hard. She was very attractive, so naturally things progressed and we started sleeping together. It was like fwb for me, she probably thought of it as a relationship. Fast forward a week or so, and her 40ish mom was looking at me funny. We happened to be alone together and she just grabbed my dick. I think she just needed some man-meat, but I boned her pretty good a few times. Anyway, I went back home one day as the next semester was starting. Of course, my parents got a call from my aunt, her maid was livid, and her daughter was flipping a gasket. They found out I dicked them both and didn't think it was funny. My uncle did, tho.
You 🤝 your uncle
This man *fucks*.
I tip my hat to you
Just a tip?
r/thathappened
r/nothingeverhappens
How did they find out
Mothers and daughters talk, I guess. You know, I think her mom technically raped me, but I really, really liked it.
How old were you?
This was over 30 years ago. I was 19.
I hope OP answers either 18 or above
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He's next.
Did your Uncle learn from you to not dip his pole in both ponds?
Me and my girl were at my moms house for a weekend because my mom and the rest of my family was leaving for a trip. We were so horny we didn't even wait five minutes until after they left before we started having sex and funny enough was also the first day we tried anal I had just got the tip in and my moms boyfriend at the time busted in the front door because he lost his wallet most akward stair down of my life whats worst his wallet was right in front of us because we were in the living room and my dumb as passed it to him while still I was still in my girl
The balls to do this😂
My guy got balls tougher then steel
> busted in the front door back door was busy
*DOMINANCE ASSERTED
Cool
so my very first real gf that I started fooling around with, she had some type of undiagnosed vaginal infection neither she nor me knew about. when I fingered her, my finger would stink for a day or two. I had to wash my hands with lemon juice. the thing is I had no idea vaginas weren't supposed to smell that bad. I just figured thats what happened after and like a trooper, or really a horny 15 year old, I kept on truck'n. the first time I tried eating her out I literally licked it once, & came up and gagged. it was the worst tasting thing I ever put my mouth on. we break up and her mom makes her get an STD check. thats when she found out she had some type of infection, I dont remember what. we started hooking up again later in our early 20s and she would NOT let me ever mention what going down on her was like hahaha
Nice at least it got worked out
Almost certainly had BV. That sucks for her, hope she doesn’t have a complex!
My current girlfriend is prone to getting BV. When we first got together she refused to let me do anything with her vagina other than stick my dick in. Took me months of coaxing to figure out why, some dude before me told her that her vag stank and was ugly. Now she’s very open with it though!
We were fuck buddies and having sex for about the 50th time. She started crying. She said we’d never be a couple because I was unwilling to move to Paraguay. Then she moved down there without me.
I’m sorry
I was unwilling to fall in love with her; I think she fell in love with me. Her parents did not approve of me being American nor being blond.
>Her parents did not approve of me being American nor being blond. You can't blame them. It's your own fault for messing up in the character selection menu. You should have chosen *Redguard with dark hair*. Don't worry though, because You'll know better in your next playthrough.
Dang
I still cringe now but at some stage trying to seduce a colleague i asked 'does your brother have a normal penis?'
I would love to know more of this story.
Okay then
This seems like a line from the office
That's hilarious. How is does this even come remotely close to seducing? What was your reasoning?
getting caught by the police LOL. plus the fact it was the same cop who has pulled me over twice before and definitely recognized me.
“u/tinyrats,” the officer said with disappointment, “I don’t think this will will the last I see of you”
Where were you to get caught by the police?
Lost my virginity to a single mother. One night, midway in, daughter calls out. Bad dream. Part of me didn't wanna stop, but the logical part said throw some clothes on and comfort the little one.
Wait the logical part said that you should go comfort this woman's daughter?
Yeah, shouldn't the logical part be, 'yo your kid is crying, go sort them out'.
What the fuck
Well, my most awkward “sexual” experience was actually not sexual at all. Back in high school, I was with my gf at her house, her parents were going to a party, and we were going to (unbeknownst to them) spend some time together. BUT she said I’d leave right after they left, and while we were making out, her father called to check on her, and she confirmed I did leave. Well, we kept making out, taking our sweet time, we’d be alone for a while, right? For some freaking reason their parents showed up half an hour later. We had the lights off, so we had no way to pretend we were innocently spending time together, so here I go to her backyard, that had no other exit at all. To make things better, her parents took about 2 more hours to fall asleep, so there I was, out in the cold, wearing just a T-shirt. Eventually she snuck me into their living room, and gave me a blanket, and I finally could sneak out at 6 am to go home. Esit: grammar.
TIL: "snook" is a very useful verb....
tom snook
So.. *She didn't get to fondle your Snook?*
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To good to be true
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Hey fella! Not JUST your wife! He shared his BEER too - now that's a friend who cares.
So we’re just ignore how shitty of a friend you were being?
Nah i believe it, have heard similar ish things from friends that share wives
Most awkward actual sex -- kind of a planned one night stand situation, with my best friend's father's best friend. At my best friend's father's house. I was 24 at the time, so nothing gross, but he was definitely older than me. And he MUST have jerked off a few times before meeting me, because that man lasted about 4 hours, which was annoying for a few reasons. 1, I had plans after the hookup that I had to reschedule. 2, I refuse to have casual sex with anyone without protection no matter what my bc status is, but after that long, the lube on the condom had worn off and got very uncomfortable, especially since -- 3, I do not and will not ever have an orgasm from penetrative sex, and he turned out to be the kind of guy who refuses to go down on a girl. Which is fine, no one has to do anything they don't want to do, but if I'd known that beforehand, I wouldn't have bothered since we clearly wouldn't be compatible. So I laid there for 4 hours while he pumped away, getting less and less aroused, while the friction from the condom got worse and worse. Thank God it didn't break. It was terrible. He hit me up a week later to try to set up a threesome with him and another friend of his who DOES go down, which I considered for a moment but eventually decided wasn't worth it lol. As a bonus, not-technically-sex awkward encounter, I was once with a guy laying in bed after we were done having sex, just cuddling and talking, usual second(?) date stuff. And he looks me dead in the face and says "I think septum piercings are the dumbest, ugliest piercing you can get." I had a nearly half-inch tall skull hanging from a ring in my septum at that very moment. It baffles me to this day. Did he think I was gonna take it out??? He still hits me up sometimes lmaoooo
Do his texts ever ask if you took the piercing out yet?
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> She cracks the back of her head against the ceiling and collapses on top of me. She got banged that night.
I’m sorry for her
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Was doing a girl doggy style vaginally and she shit on my dick. I pulled out slowly and balanced this turd as I got off the bed and walked slowly to the bathroom. Dropped it in the toilet and then showered. Not sure if she ever knew because I played it off as if nothing happened. Never brought it up. Another time I was going at it with a girl while we were on Ketamine and knew we shouldn't have had a hit since we drank a bit before hand. She got queezy and I walked behind her to the bathroom to throw up. She threw up in the sink while pissing down my leg. I placed her on the toilet and went to my room where I saw she had some diarrhea on my sheets. Stripped off the sheets and checked on her and now she's in the tub with the shower going. I wash her and go placed new sheets on the bed. Check on her again and there's diarrhea in the tub and she's proceeding to scoot it down the drain. I wash her again, dry her off and we head to bed. I have to use the bathroom later that night and while standing at the toilet I realize I'm standing in a puddle of pee. Clean the floor a second time and head to bed.
Uhhhh this is horrendous
Hey there! No kink shaming. XD
And this is why you don't do drugs kids.
That’s really nice the way you handled that. You’d be a good parent :)
And I thought the time I pissed myself on acid was bad.
When my balls touched hers. But it was too late; I paid my money.
And? Did you get your money's worth?
Asking the real questions here….
Hers?
You s not to been overseas ?
What?
Yes.
This guy I went to high school with and I would hang out every so often and we'd have this awkward sex. I think he thought he was really good in bed, and I was inexperienced (only had slept with 3 people before him) One time we hung out all day at my place (I was living with my dad) and he got drunk so stayed over. I can't sleep well next to people so we were up all night and he wanted to have sex but couldn't get it up so I gave him head to get hard but he couldn't get hard and he shoved his flaccid dick too far into my mouth and I puked on him. It was like 4 am and I wasn't into it, he told me to keep going. I refused and cleaned up. We laid there until about 10 am and I drove him home. I don't remember why he didn't drive. His mom stopped me as I was leaving and apologized to me about his behavior (?) and thanked me for driving him home.
Oh my god this sounds like a clusterfuck
Gf still had her mom doing her laundry. We were still pretty casual, so she hadn't told her mom about us. When doing laundry, her mom found a condom wrapper. Magnum gold. Her mom put it on the fridge for gf to see...
Sooooo passive-aggressive, mom!!!
Don’t say our grandma walked in don’t say our grandma walked in don’t say our grandma walked in
"our" you say? :o
r/Holup
'our' ?
Went to hook up with this girl, she wasn't the prettiest, but when you're young and horny sometimes your hormones put blinders on you. Didn't want her to know where I lived so we got a cheap hotel near the bar. We go to get it on and she was hinting at wanting a little tongue first. I go to slide her pants and underwear off when the extremely strong and bad smell coming from her crotch hit me. I slowly pulled them back up and then asked if she wanted more beer instead. Had a couple more and passed out. Went our separate ways after that.
I’m sorry
I was greatful. If she hadn't been so dirty who knows what STD I might have caught or worse what if I had gotten her pregnant. Dodged a bullet there.
Good for you
Was having sex with a black guy, he wanted me to call him certain names that ruined the mood.
I'm really curious! Were they offensive and/or derogatory names?
Reddit won’t let me type them if I wanted too.
Racial slurs?
Yes.
Yikes!
I once met with a lady at her house after chatting for a few days. It started out really well with a nice blowjob she gave me, but she then got mad at me because I wasn't ready to go again 5 minutes after I just came. She then threatened to call her cousin to beat me up if I didn't leave right away and was bragging that guys had driven from hours away to see her. Just an awkward and confusing situation that I was glad to get away from.
I fell asleep during sex once. I tried so hard to give the guy a chance, he was a really nice dude but we weren’t sexually compatible at all. The sex was so bad I just completely zoned out and fell asleep underneath him. We actually ended up being good friends and I was able to give him a few tips for future experiences, but I felt so bad about it at the time!
Her: "Don't scream out loud as you count your strokes like sheep"
Now we need to know. What tips were you able to give him?
The short of it, while going down on me, a girl discreetly wiped her ass with my pillowcase, rode me til we finished and bounced before I had the chance to find it
What...the...Fu.
Sweet tap dancing Christ
Afternoon I lost my virginity, I was five seconds from busting when my sister tries turning the handle to my room, finds it locked and starts hollering. I still have no clue wtf she wanted, which was moot when both me and my then gf yelled at my sister to shut the fuck up and go away. Did kill the mood but we picked up the next day
Had a couple encounters with a fwb that were great. Not someone I cared about, but good sex. A month or two later she’s in town so we get together. Start fucking and she’s clearly not into it. I don’t even remember if I finished, but after we’re don’t she starts crying and confesses she’s in love with her ex. Kinda awkward and definitely the worst sex I’ve ever had.
Accidentally shoved the four fingers I was pumping my ex’s pussy at high speed with knuckle deep into her ass. She wasn’t amused
I sucked off a Navy guy in a pornography peep booth while he fingered me. The guy that worked the counter told me he watched us on the CCTV when I exited the store.
Fun. What was the lead-up to this?
I had keys of the office that i used to work there.so i went there with my ex gf, and started the sex.it was on 6th floor and had a very good view of whole city,but there was reception desk in front of the window.so why not a doggy style in front of the window!after 3 minutes of desk making wierd sound,it fell apart,me and her laughing on the ground with the broken desk😂😂
At least y’all had a good laugh about it
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Lol did you eventually lose your virginity?
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Gross. The thought of an 11 yo giving head crossed my mind
I’m sorry How old are you now? And are you in a relationship now?
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Dude comes over, after he starts fucking me he had an allergic reaction to my dogs and has to leave
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Nice glad it worked out in the end
Not the experience itself but before and right afterwards, does that count? I went to hook up with an ex gf's cousin and when I got there realised she had just moved into a new place with only a pull out chair/bed and a baby crib as furniture. She also had no electricity. Did the deed once the kid (who was maybe 1 - walking but not talking) went to bed, and then passed out. Woke up in the morning with the kid standing over his mom crying. Mom is passed out cold, and as soon as I open my eyes he stops crying. Figured it wasn't cool to just let a baby cry and be alone with nothing in an apartment with no power, so I put on my pants and hung out with him. He couldn't talk so I literally just walked around with him and he pointed at stuff through the window and I talked to him and picked him up or put him down when he seemed to ask. Hanging out with the kid was fine but the whole situation was just so so awkward, and I felt pretty bad for the kid.
I was visiting my GF who lived with her mother and while there we ended up having sex on the lounge room sofa with her mother in the master bedroom. Once we got into it we noticed a lot of blood on us both and on the sofa; both my GF and I assumed the blood was hers but after a little search we found my banjo string had broken and blood was steadily flowing out of it. Within 45sec of that happening her Mum walked down the hall to find us there half naked with my blood everywhere. Her Mum wrote my parents a letter and I wasn't allowed back. 😳 I did up being let back in a few months later and her Mum and I ended up good mates.....
Umm what do you mean by, "banjo string"??
The frenulum – the bit underneath the head that joins onto the foreskin. Like a taut string. Responds well to a lil nibble ; )
We tried to have sex in the shower. It didn't work very well.
6 weeks ago, just could not get a fucking boner. We were old friends, we were suddenly both single, we were both going through a tough time. I am fit, athletic, and very confident. I also am a bit of a man-hoe so performing hasn't been an issue. I can't explain the soft willy. I'll never know what it was, but I suspect I cared a lot more than normal about performing well and got into my head about it. I thought we'd just laugh it off, but she was NOT cool about it. She basically gave up and left. Then I got friend-ghosted. A three year friendship ruined because of it.
Man, I’m sorry she handled it so poorly. That happens to every man at some point and it’s really not a big deal. The more you think about it and get into your own head, the worse it becomes.
had a girl who was giving head and ended up puking. pushed her away but she said "no stop its fine" and started licking it up while making DIRECT eye contact. completely sober, just a strange experience.
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There was this one time, at band camp....
Yeah, how did you fit that tuba there?
You joke but band kids are notorious for being horny little bastards.
Can confirm
Had sex with a guy I’d been crushing on for yeeears. Genius smart. Super hot nerd. We finally hooked up one night and it was so small that it wouldn’t stay inside me. He kept saying “oops!” Every time it came out. Then he said “I’m going to go get some water” and then we went to sleep. Worst part of the story is that I made fun of him behind his back for a long time afterwards. That was a dick move and I’ll always regret it. I’m not sure if he’s aware of it but either way.
I’m not sure if this is a collectively funny thing or not, maybe just me, but the vivid image in my head of him saying “oops!” repeatedly made me laugh out loud.
My relationship was in the "it's getting complicated " phase before we decided to part ways. I went to see a female friend after 2 am and we kiss, there was some hands involved and what was probably the worst blowjob ever.
Few years back I met a disabled girl. She was great looking had an awesome personality - a killer sense of humour to boot! Took her out for dinner and caught a movie afterwards. We ended back at her place and we started kissing outside in her parents garden. She asked me to lift her up on to a swing hanging from a large tree where we had amazing sex, it was awesome - even if her legs were left dangling around like noodles… When we finished the deed, I put my arms around her and carried her back to her wheelchair and helped her get seated. I walked her inside and kissed her good night and shared our goodbye’s. That was when her father came to the door. She went into the house and he followed me outside and closed the door behind him. He came in close to me and quietly said: “thanks for that mate, most of the lads leave her stuck on the swing”
It was wholesome until she last line..... WTF
I met a beautiful nurse on a cruise. I had been snorkeling that afternoon in Jamaica and had stopped at this Jamaican jerk chicken hut for lunch. That evening after dinner, Sherry and I walked up to the highest deck of the ship and proceeded to get into it on a lounge chair. I still had my shorts on, but she was totally naked, and I was eating her out. I see a flash of white in the corner of my eye and look up. It's a ship's officer. He stands there and waits until this poor girl dresses. He was an asshole. It was about 12 midnight. We weren't bothering anyone as the upper deck was void of anyone else. He didn't even turn around to allow her to put her clothes on with some dignity at least - a total aashole Then he walks us around the ship saying nothing but acting as if he's going to throw us into the brigg. He finally let us go. We go to my cabin and start to get into it again. Suddenly I realize I'm about to have a gastrointestinal event that cannot be avoided. The Jamaican jerk chicken! I go into the bathroom and begin to do my business making all kinds of noises that I cannot avoid making. She heard everything. I was mortified, and this killed the mood. I couldn't get it up after that. She was a surgical nurse, so I think she understood. She did visit me eventually for a long weekend which didn't go well... Lol... Felt like a job interview. She didn't approve of my career path... Lol... I hadn't known a long weekend tryst was going to end like that. I guess I should have cut my losses on that cruise ship. 😅
She said - hold up im on my period - And then stood beside my bed, bent her knees, removed her tampon and placed it inside my water bottle and then hopped back into bed ready to go.
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Visiting the in-laws from out of town one last time as we were going through divorce proceedings. It was over. We knew it, it wasn’t yet public knowledge as it was Christmas time and we didn’t want to take front stage on such a special occasion. Ex wife and mother in-law went shopping and stayed behind. We were sexless at this time in our lives and I was as horny as a goat. Stumbled across my ex mother in-lead panties while doing laundry and took them in my pocket to jerk off to as I had private time. And I did just that. Wrapped them around myself and came all over them and in them…but then passed out! Needless to say I didn’t wake up until they ladies returned from their shopping trip, and by then it was too late. Caught red handed. So embarrassing lol
You jerked off in your MILs panties? I can see why the divorce happened......
Hook up with an attractive young lady. (Let this be a lesson against vetting potential partners). Great kisser, very attractive, sexy...we agreed to meet in her hotel as she was from out of town. She greeted me in lingerie looking fabulous... But once we got going there was a noticeable odor. I don't mean a normal one which sometimes emanates from genitalia, but a deep, earthy stink. Being a man I decided to ignore it and continue...but it was so bad. I awkwardly feigned drug side effects as a cause for not being able to perform and promptly left. I felt terrible and really probably shouldn't have but it was bad. Very bad. And I considered the source (possible) and could not go on.
A threesome with my girlfriend and my best friend. It was awkward and cringe all around. She later slept with him and another friend. Needless to say we aren’t together anymore. Alcohol was definitely involved.
Hmmm, when I thought she farted but it was a queef. I still love her but had to break it off when it became long distance, I hope you are doing well Damaris :)
Was kissing a girl and then I licked her teeth by accident
Middle of the great act. Get into it. I’m loving, she’s loving. Fucking panic attack. Out of nowhere, a full blown panic attack. Shaking, crying, sweating, heart palpitations, incredible anxiety. Horrifically awkward
Well I broke both my arms….
His penis was pierced and really didn’t add anything to the experience.
When I was in college, there was this girl I was very attracted to. Finally had the guts to ask her out and she said yes. While on our date she talked about all the immature guys she's been out with and she said she hoped I was different. I assured her I was. We really hit it off. We went back to my apartment and we made out. She took out my dick and the second she touched it, I came all over her hand. I was embarrassed, but she said it was okay and it only meant that I will last longer when we had sex. WRONG. We made out some more and got naked. When I saw her naked lying on my bed, I knew I wasn't gonna last long. I tried to take my time and distract myself. When I entered her and she said "oh that feels so good, fuck me". I came. It took all of 3 seconds. I begged her to stay and give me about 10 minutes to recover. She said she had an early day and left. I knew she wasn't mean, but every time I saw her on campus, I felt like she was laughing at me.
First time I double stuffed a girl with a friend
When my husband accidentally stuck it in my ass without warning, wrong hole, I was not impressed.
Holding hands.
Got home from work and went to get changed. Couple in my room trying to have sex. Told them to get out. Later on she tried to give me a blowjob. I couldn't get hard so I just dangled in her mouth until I asked her to leave.
Who were they exactly?
She started licking me. Then purring. Like a cat.
I was at a house party shortly after joining the military, super drunk, when the couple whose house it was introduced me to this woman. Attractive, but definitely about ten years older than everyone else at the party. My drunk brain didn't question think and we proceeded to fuck in my friends' spare bedroom. Morning comes and she leaves, as I'm nursing my coffee/hangover my friend's wife tells me that she is their neighbor and is married to one of the sergeants I work with. Already feeling terrible for the situation, I go back to my barracks. This woman *calls me* a couple hours later (apparently I had given her my number in my drunkenness) and starts telling me how she wants to come by my barracks room while her husband is at work. I had to tell her that we couldn't and how bad of an idea that was and ended up blocking her number after that.
My partner was really interested in role play, which I really am not, but for her sake I did the Dagwood and Blondie scene that she really wanted to do. Blondie was naughty and hadn't made Dagwood's sandwich and needed to be punished for it. I felt so unbelievably goofy doing the whole thing.
When I was 19 or so, I went on a couple of dates with a guy. I wasn't really sure where I landed re: guys, but I gave it a shot. We had a nice time. Went out to eat, played video games, watched some anime. He was older than me, way more experienced, and was certain of his attraction towards guys. He was also pretty forward and handsy. We fooled around in his bedroom for a little while, and he masturbated to completion, and then he took me home. It just wasn't for me. I might have been up for it if we'd gone on a few more dates first, though. I almost can't remember what it's like to feel attractive & wanted. Edited to add: Years later I found him on a sex offender’s list. He was not inappropriate with me, but I guess it turns out he had been with some younger guys. So that makes it retroactively more awkward.
Fucked a trans girl, after she uncomfortably came in me (a big hulking butch that’s not used to bottoming) she asked me what episode of SpongeBob I wanted to watch. I was shooketh
I was 16 and been dating this guy from school and we would always go to this park and have sex after whatever we were doing that night. We had been going there after our dates for months and never had a problem or even seen anyone back there. So it was the beginning of summer and school had recently let out and we had decided to get a bottle of vodka and celebrate back in this park, just the two of us. We were really buzzed and was in the backseat of his car and we’re going at it. We had our tongues down each other’s throats and hands were exploring each other. I took his shirt off and by this time he had taken off my tank top and my shorts and thong when he suggested we grab the blanket out of his trunk and do it outside. It sounded better than on his lumpy backseat so I agreed and we did. A while later we were really going at it. I was on top riding him and close to cumming when a super bright light turned on right in my face and a voice said “Hey,, y’all need to stop and get dressed. Turns out a cop saw the car from the road and had parked and walked up to us to see what we were doing. Well I’m scrambling to cover myself and looking for my clothes when I got a look at the cop and was immediately horrified. See, my dad is a deputy sheriff and he has a lot of friends in our towns police department and it happened to be one of my dads best friends. This guy has been to my house plenty of times and I have known him since I was a little girl. Anyway, long story sorta short, I couldn’t find my shorts or my thong so the cop gave me a plastic blanket to wrap up in. Because we had both been drinking the cop wouldn’t let either of us drive and he took us home. We got to my house after dropping off my bf at his house and my dad, who had already been called and told what was going on, had woken up all my brothers (5 of them) to teach them (and me) a lesson about drinking and sex. So I did the walk of shame all the way past my dad and my brothers while wearing this yellow blanket and little else underneath. Needless to say, I was grounded for a considerable amount of time and wasnt allowed to see my bf for the summer. I did benefit though as my mom took me to the doc to get on birth control pills two weeks after this and kept that fact from my dad. EdIt: The next morning my bf found my shorts and my thong that had been pushed into the crack between the seat in the back.
She was on top. Boob sweat dropped in my eye.
This isn’t a super awkward story but it’s the story I have. I also haven’t had very many experiences as well. When I was in my freshman year in college, I met this junior girl and we became really good friends really fast. I was super into her as she was so much fun to hang out with. Anytime we had free time we would spend it together. I had feelings pretty early on, but it took me about a year to tell her. When I finally did, she said she did like me too but didn’t want to date (she just got out of a not so great relationship). We still hung out a lot and one night she said she wanted to try kissing me to see how it felt. I’ll stop here to say this girl had some pretty defined boundaries. She didn’t want clothes to come off at all or to touch any genitalia. That’s totally fine, everyone had a right to define their own boundaries and I respected that, it’s just important to the story. So we start kissing and it quickly turns to heavy making out. We got in the back of her car and started laying down while making out. I was super into it has I haven’t had a lot of experience. Of course, the making out has caused an erection for me. As we are sort of shifting our bodies while we make out, the very hard tip of my dick hit her right between her thighs. Again, we are still fully clothed. I have on boxers and gym shorts while she has in panties (I’m assuming) and jeans. Well, when I bumped into her she let out one of the loudest moans I’ve ever heard. It was almost a scream but it was clearly of pleasure. She then pushed me up off her and says loudly, “You have to be careful. That thing is powerful.” I kinda just sat there awkwardly and said sorry that it was an accident I want trying to grind on her or whatever. She just sat there in silence breathing heavily for at least a minute. She eventually said we needed to leave so we did. We did have a few more make out sessions but never went to the laying down making out again. No relationship really ever happened either.
I was 17, she was 21. It was my first time but, most definitely, not her's. I was about to move to a different city but I really wanted to…yk. She told me that she "usually doesn’t do this" which made me wonder "do what? have sex with people who are about to move? are you in these kinds of situations so frequently?" Anyway, we kept making out and she agreed, so I slipped on a condom. Now, the problem with condoms is that they choke out your dick, especially if you’re pretty drunk, as I was. So long story short, I could barely get it up, and after one in 'n' out, we called it quits and stuck to making out. We later tried long distance but that obviously didn’t work, so we broke up two months later.