We’ve all had our moments of sexual inexperience, and sometimes the stories are absolutely incredible (in hindsight)
Below are 30 stories the most obvious sign of sexual inexperience they’ve encountered.
1. Tight squeeze!
I went on a date with a girl in high school who was supposed to be experienced. We started making out, and she started squeezing my balls so hard I nearly cried. I thought she knew what she was doing, and I had no idea, so I went with it.
Wemedge
2. Swing and a miss.
Not mine, but one of my friends experience. She was in college and started making out with a guy on her couch while they were both a bit intoxicated. This led to deciding to have sex, and as she laid there, he seemed to be really into his thrusts. The problem, he was doing the slit between the couch cushions and not her. It doesn’t matter how many times she tells this story, I always crack up.
BattyDame
3. A whole new world.
I had to show my girlfriend (who was well into her 20’s) where her clitoris was and how to masturbate.
The funniest part was, afterwards, she…(Continued)
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She masturbated herself every chance she got after that for about a month. Her roommate sarcastically thanked me for all the extra noise in the apartment.
cartmen34
4. She didn’t know!
Was trying to make a girl have an orgasm for the first time in her life. She’s getting all worked up when suddenly she yells out ” I HAVE TO PEE!”. She darts to the bathroom and tries to pee for a few minutes unsuccessfully. She was climaxing but thought she was going to piss herself.
ButterMyMuffinn
5. Sexy times with a shark.
Teeth on a blowjob. Her downsuck was great but the upsuck felt like I was getting one from a shark.
edge231
6. ARE YOU PREGNANT?!
My first time with this guy I was dating. I knew he was a virgin, and I thought I was prepared for what might ensue. How wrong I was.
After dinner we got down to it at my place. He lasted a few pumps, finished. Fine. I was prepared for this. Then he FREAKS OUT. It took me a minute to get him to effectively communicate what was going on. He jumped out of bed, threw his clothes on, and yelled “OH NO! ARE YOU PREGNANT?!?!?” in full panic. He was dead serious and waited for an answer. I let out a confused “uh…no…?” He then…(Continued)
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He then ran out of my apartment and went home.
We used two forms of birth control (pill and condom). We were in our 20s. He had already gotten his bachelor’s degree.
bluejay304
7. This sounds disastrous.
He continuously kept licking my peehole and tried to shove it in there. We changed positions cause he simply couldnt put it in the right hole. I got on top and he proceeded to enter my butthole.
“I’m gonna tear your walls” he said in a text message 30 minutes before coming over.
SkankkSchrader
8. Bad idea in hindsight.
“Bite my vagina”, bite it!!”
“Are… Are you sure…?”
“Yes damnit… Bite my vagina!”
It happens:
“..never do that again! Oh god, never do that again!”
CaryGrantLives
9. Amazing. Simply amazing.
When I was younger, a girl and I were into each other on a vacation at this resort kind of thing. So we are in her condo making out a bit on her bed while some others are in the other room. Somehow wedgies come up and I threaten her in a playful way with one, thinking I’m smooth. She proceeds to inform me that I couldn’t give her a wedgie. Of course I’m like” I bet I could” to which she says “I’m not wearing any underwear” and continues making out with me. I go to check and quickly feel her bare ass on my hand. She kisses me. I pull my hand out from inside her pants and…(Continued)
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I pull my hand out from inside her pants and grab her jean shorts and pull.
Didn’t lose my virginity that night…but at least I proved I could give her a wedgie, I guess.
Still think about this sometimes, where I could be today if I had just made a slightly different move.
Obliviousobserver
10. First time’s a charm.
He put the condom on backwards and couldn’t figure out how to roll it down. I told him it was okay and showed him the proper way to put it on.
I’m still with him over a year later, he got better.
rkkid9
11. A true gentleman!
Through proper manipulation of circumstances my girlfriend and I got her sister and a friend of mine to share a bed. She liked him, he was bemoaning his forever alone status and I knew he liked her as well. They watched TV, next to each other. She moved her hand over to his. He drew his hand away and apologized for having somehow accidentally touched her.
Fraxxxi
12. WHAT IS THAT?!
Got a handjob from a 28 year old virgin, she was shocked when semen came out.
Teantis
13. Oh…yikes…
I walked in on my first boyfriends best friend with his girlfriend. He had her bent over and was pounding away like jack hammer. She was moaning but as a woman, I know the face she was making. She was…(Continued)
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She was SUPER not into it. He thought he was the shit and bragged about it for weeks.
asafter8
14. Was he human?
Once I slept with a guy who kissed like a vacuum cleaner. He straight up suction cupped my mouth, and the more I pulled away, the more he stuck onto me. He then bit my nipple, and that took a week to heal.
RealLifeAprilLudgate
15. What is that?!
When my muscles contracted inside, he jumped back and said “What was that?!?”
sykopoet
16. Yoda kisses.
Had a girl who was flirting with me heavily while we hung out, even saying overtly sexual things then pulling back as soon as I reciprocated (which is kind of a sign in and of it’s own), but when I went to kiss her, I was greeted with what I can only describe as “Yoda Mouth”. Her lips were pursed together in that way Yoda does when he’s really disappointed, or seems to be contemplating something, and I immediately thought that maybe I had misread her and she was just too polite to say “hey, you are an asshole, stop it.”
Next time we hang out I…(Continued)
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I assume it’s platonic, she is still super flirty but I figure that’s just her thing, but as she goes to leave she looks at me and says “Kisses?”. I don’t remember exactly what I did but obviously it must have really shown my “uh, no thank you, ma’am” feelings, which would have normally ended things until she half yelled “I’ll open my mouth this time!”
That… is about the most obvious sign of inexperience I have ever seen. She was over 30, and hadn’t yet quite gotten making out yet.
PM_ME_UR_COCKTAILS
17. That is a unique story.
My girlfriend once sneezed the dick out.
rustyshackleford193
18. Ah, the wrong hole.
Religious friend were newly married and having trouble getting pregnant. Lots of doctor visits and 2 months later found that they were doing anal.
ThisLookInfectedToYa
19. Let’s try this!
I’m not sure what it is about recent movies and stuff, but I was with a girl a while back (She had been a virgin) who was certain that doggystyle was just sort of “how it was done”.
Said it’s basically all she’s ever seen in movies and the small amount of porn she’d seen.
The conversation came up after our 3rd or 4th time and I told her to…(Continued)
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The conversation came up after our 3rd or 4th time and I told her to lay down as we were getting ready for action. Missionary position just blew her mind. Way more satisfying for her. She was all like “why don’t people do it like that all the time?”
lowertechnology
20. Insert Pinocchio joke here.
A guy once told me he definitely wasn’t a virgin and I was kind of on board until he went down on me and inserted his nose into my vagina and asked if I’d finished yet.
WellWhyTheFudgeNot
21. Interesting…
She had only been with uncircumcised dicks, so she thought the skin was supposed to move with the hand.
blackbeltbud
22. And that’s when I knew.
Attempted to hook up with a dude. He spent all night talking about how much he loved hooking up with random girls in college. After everyone left were just sitting on the couch together in silence. I got inches from his face and it took him probably ten minutes to kiss me (horrible kisser). Didn’t move until I did. Didn’t get close to me except to kiss me. Then got his hand under my shirt and bra, grabbed both my boobs in one hand and just kind of shook his hand a little, on and off. It was the most awkward thing I’ve experienced.
After about ten minutes I…(Continued)
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After about ten minutes I couldn’t take it and I told him I had to be up early to visit my grandmother so I should probably go home. Laid awake in bed that night and fully embraced my lesbianism.
thesheepingrovepark
23. Koala mode, engage.
She koala-ed me. I was on top and she wrapped her arms and legs so tightly around me I couldn’t move at all. I just kinda had to lay there on top of her for a while.
Seanmeado
24. Knowledge is power.
We started making out and groping and he puts his hand down my pants. He starts feeling around the front of my crotch (directly below my stomach) for a bit until I tell him, “Move your hand lower.” He immediately goes bright red and says “I thought vaginas were in the front.”
louloulouise
25. It bleeds through the writing.
Not in real life, but when I’m bored I read fanfiction. I’m ace, so I don’t routinely seek out the sexy stuff, but sometimes it comes up in a long story. 99% is written like “He put his shlongalongadingdong inside her thingamajiggie. Her humongous booby boobs boinged.”
alderaanirebel
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26. Honest question!
Oh, my poor first boyfriend.
We were both 16-year-old virgins; I wasn’t really expecting all that much better than it actually was (i.e., very brief and slightly painful), but then he couldn’t help himself from asking:
“So, did you…ya know…um…”
“Orgasm? You mean, did I have an orgasm?”
I paused for a minute so that I didn’t say out loud the words in my head which were, “Yeah, sure I came in under 45 seconds without you so much as looking at, let alone touching, my clit. You mean you missed the earth-shattering multiple orgasms?”
Instead, what I said was, “No, baby. Not this time. We can have fun trying again next time.”
badly_behaved
27. Insults don’t do much.
I know a guy who thought that complimenting my boobs was a great way to flirt with me. He also complains a lot about how he’s still a virgin.
I don’t have any experience either, but I’d like to think I at least have manners.
La_Cierva
28. There is always room for improvement!
Ignoring my feedback instead of listening to what I have to say. I promise you, champ, you don’t know my body better than me and acting like you do makes you look like an insecure jerk.
starryduchess
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29. The absolute worst.
When they have no idea where to put their hands, so they just lay them at their sides. Known as the dead fish. Awful.
JeffBuckleysGhost
30. Four…hours?!?!
Oh, this is a good one.
I’m at work earlier this year and myself and four other guys are shooting the shit, talking about whatever, with the sixth person there a female younger than all of us (we’re early-to-late 20s, she’s 19).
Conversation turns to the definition of “good sex” and the one female there pipes up about how it isn’t usually good for her, as “sex doesn’t get good until after four hours or so”.
We’re all dumbstruck and question her, thinking either we misheard her or she misunderstood the conversation, but nope, she stuck firm at four hours. Despite our informing her that:
-ain’t nobody got time for that,
-even with lube it’d definitely hurt her to go that long and
-no way the dude doesn’t finish by that point (or give up) she maintained that four hours is her climax point and then doubled down and said that “two and a half hours is her minimum”.
We’re all convinced she’s a virgin now (not that that matters at all, but the blatant lying to be “cool” or fit in was super easy to recognize) and can’t take anything she says about relationships or sex seriously now.
ImmaculateReception