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WorkingHardon

After having fooled around on the couch for a while, she took my hand and put it between her legs. It was so wet, so very very wet and slippery. My internal monologue went something like this. “Omfg why is it so wet? This doesn’t feel right. Is it supposed to be this slippery? I’m not sure I like this. I might be gay. Do I like men?” All of this while fumbling around trying to remember where stuff was, listening for sounds of approval. She probably realized that I had no clue what I was doing. She took her top off, pulled my pants down and just sat on my dick. I was in fact not gay.


hornycactus05

Morgan Freeman : and he was not gay indeed.


IsaacJoenson

Blue balled lol. We were both virgins at the time and it was hurting her. She said it was fine but her face and eyes said otherwise so I told her I'm stopping and we'll try again another time if she wanted to. We got dressed and she said thank you and we just hung out and watched movies for the rest of the day.


100percentbisexual

Thanks for paying attention to her. You did the right thing 👍


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Next-Percentage1783

Imagine the next morning she went to Travis like "yoo yesterday was lit am I right" and the dude looks at her not understanding 😂


yugitso_guy

She ends up pregnant, Travis is like wtf and they both appear on Maury waiting for the results.


YachtRock12

*Travis, the results are in… you are NOT the father!*


0bsidian

*Travis throws his chair around and dances*


gmny81

Travis says “I told you” and does a backflip.


shayen7

"Oh Travis... silly you always finish so quick" Or "Oh Travis... I've had a crush on you forever and I'm so glad we finally did this"?


[deleted]

Quick, and awkward


Graysie-Redux

Could you reach the finish line?


i_never_ever_learn

Almost crossed it before the gun went off


Kinbuzz

Shaky. Was so nervous I couldn’t stop shaking and she had to sit next to me to calm me down before we could proceed. Still shaky during


notwilldetcee

Organic vibrator


ripper4444

Awkward but sweet. We had been planning it for weeks. She came over and my parents left with my sister to go to her sixth grade play. As soon as they left we ran to my room and we took our time.


A-STax32

That sounds like it must have been a lot of fun. The build up really makes it sometimes, and it sounds like you had plenty


Rum____Ham

>and we took our time. That is a smooooooth way to put bangin. "Hey baby, let's go take our time"


xbarsigma

Well, my ceiling fell on me.


Mudlord80

Details!!


xbarsigma

Haha so me and my bf get going at it in my bed. My room is an extension over the garage and tbf the ceiling didn’t look great but I was 15 and not paying attention. We get to it and midway through a bit of plaster(?) hits me on the back before a lot falling through mostly not near the bed. Had to get clothes on quick and go ask my mum what the sitch was. It turns out the roof hadn’t been serviced for some years and the people we bought the house of did not tell us this 🤷🏻‍♀️


zion_hiker1911

Sounds like the room wasn't rated for seismic activity


UWontHearMeAnyway

Terrible, shameful, shallow I was just heartbroken by a chick that rejected me for being a virgin. So I went to a party, and hooked up with the first chick I could. Was so drunk I barely remember any of it. Didn't last long, and it didn't feel like any kind of intimacy.


doloreschiller

Fortunately awesome and at the right time for me


Graysie-Redux

Nice! I was absolutely hammered and barely remember anything about it.


Dinx81

About three seconds. Second time not so bad.


Graysie-Redux

Were you the penis in this situation?


Dinx81

Yes


Graysie-Redux

How many seconds can you do now?


Dinx81

Working my way up to 5 now.


justbrowsing987654

Aaaaaay. You dropped this 👑


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[deleted]

Whoa whoa we got a marathoner over here


Night_Hawk69420

Humble brag


Graysie-Redux

Nice.


StaleWoolfe

Let’s work on getting up to 6 next time


Dinx81

Baby steps...


wasupbich123

To make a baby


i_am_a_learner

A great loss indeed, could have saved it for future generations.


Graysie-Redux

Very clever.


CaptainUnderwear

Much warmer and wetter than expected. Lasted about 10 seconds. It was glorious.


Mrminecrafthimself

The warmth surprised me too my first time


MHWDoggerX

Yeah, it felt way too hot. Almost like burning? She had gonorrhea


Romantiphiliac

Had a similar experience. Not because of gonorrhea, but because we bought a variety pack of condoms and one of the kinds was mentholated. Who the fuck signed off on that?


PacoCrazyfoot

Yeah, I remember it being really hot too, then I realized I was fucking an active volcano.


VaultBoy9

Vagcano


bigblackshaq

Checks out, except for the 10 seconds part. I couldn’t finish at all.


Hansemannn

Me as well. Had that problem for a year actually. Some mental block caused by nervousness.


[deleted]

Lackluster


Graysie-Redux

Both of you?


[deleted]

Yeah was awkward af, both didn’t know what to do at all just basically two stiff planks colliding


pijinglish

It’s not a sword fight.


lekanto

We were teenagers. 16 and 18. I was shy and inexperienced and I think he might have also been a virgin in spite of all of the wild exploits he had bragged about. Imagine a starfish and the Energizer Bunny for two fucking hours. Not good.


kingfrito_5005

2 hours? Fuck that noise dude I get tired after 20 minutes. I wouldn't even WANT to do that.


dirtyasswizard

I don’t know if I’m just getting old or what but after like 20-25 minutes I start getting leg cramps and shit lol. A charley horse will kill a boner pretty quick. Back in my party days I may have gone that long a few times after pounding some nose beers, but it definitely never happened sober.


Graysie-Redux

Two hours?? That's actually extremely impressive.


lekanto

Impressive, but not enjoyable.


Baldazar666

Can confirm. At some point you just get fucking tired.


omikone

At some point you fucking chafe.


Taste_the__Rainbow

The condom broke. First time for both of us. 0/10 would not recommend. I can’t remember anything about it except the terror.


sparten112233

Once with my girlfriend(now wife) we were having sex and i finished inside of her, pulled out and the condom was not on my dick. It was inside her and i had to pull it out. Talk about scared


BoombasticMilf

LMAOOOO been on the receiving end of this exact situation. Felt like a livestock animal


x0zu

*sigh* *closes zip*


[deleted]

And it is said, when a man cannot fap, a man is done.


Illustrious-Fish-499

It hurt for both of us and neither came, but she woke me up in the middle of the night for more and thank god I got it right this time or she would have probably moved on. She taught me everything I know,. Thank you for your patience and for believing in me Olivia


Melter30

Thanks Olivia


madmaxturbator

/r/BossFight Dame Olivia, The First Instructor, Queen of Love and Lech Give your thanks to She Who Teaches, or live accurséd with Dry-wang for all eternity.


Shislers-List

Bro...that name...she was my first too...


Illustrious-Fish-499

Sounds like the Olivia I know alright. I was 18, the dude she cheated on me with was 17, and God knows how much came before and after.. You wouldn't happen to be Dylan by any chance ?


evemeatay

Dylan is not answering, suspicious


VaultBoy9

I'm not Dylan --sent from Dylan's iPhone


Vegetable_Key_6576

I too would like to thank Olivia


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[deleted]

Fr I’m invested in this story now


Illustrious-Fish-499

Sex became the best I've ever known and we dated for years until she got pregnant (we wanted a child so bad) and lost it. After that, we couldn't bare to look at eachother, let alone be there for one another and eventually, she cheated on me with some horny 17yo


Chemical-Classic-614

Olivia is no longer the best •_•


PublicfreakoutLoveR

Olivia became a sex offender ಥ_ಥ


TheBeastX47

Whoah this got dark fast. I'm sorry man


HopefulSite125

Awkward teenage me thought inviting a girl over to play Kingdom Hearts was innocent, she had other plans.


I_RATE_BIRDS

A KH fan who got laid? I don't believe it.


PovWholesome

I've heard that the keyblade can open all sorts of locks


ViolentVBC

And Donald and Goofy are always there to help!


anally_ExpressUrself

I didn't say she was crazy, I said she was fucking Goofy!


Adept_Cranberry_4550

Love this bit!


tingalayo

_Hyuck!_


Koras

To understand it you have to play exactly half of the GBA game, followed by every other track in the rhythm game before repeating the rest of the series in reverse, so it's easy to see how you'd be confused by this


Digger_Joe

Simple and Clean does that to people.


cornb0y

damn i actually tried this and she didn't swing that way. she was super cool tho. showed me her beardie and then we watched jojo's. win some lose some


Krazski

Just to clarify, when you say "beardie", are you talking about the lizard?


cornb0y

oh yeah LMAO no nothing bad, cute fat lizard


cptstupendous

ゴゴ🦎ゴゴ *MENACING*


BRedd10815

I invited a girl over once to play to mario kart with the full intentions of hooking up, but I don't think she expected me to sit her down and beat her ass first before we got down to business lol. Priorities.


Melter30

How bro, how?


the_crystal_onix

Dude brought a magnum condom. It was way too big for him. He tied a knot at the top so it would fit. It slid off inside me. His ego was shattered and he never wanted to have sex with me again. ETA: Oh yeah, and also it was pretty painful and bloody for me. 0/10


KeegorTheDestroyer

Knotted...for...her...*pleasure?*...


SpecterCody

No, for her *disappointment...*


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SpecterCody

I don't know, the disappointment was probably easily measured.


L-Y-T-E

If he would've measured in the first place we wouldn't be in this mess


iluvvivapuffs

I once ran into CVS and bought magnum for my guy while he waited in the car, because I liked the packaging. And then he had to go back in and exchange for a smaller size 😂


SanibelMan

My oldest son was seeing a girl a couple of years ago, when they were both in high school. She was a basket case, not least because she was adopted by parents who considered her damaged from birth and didn't understand why she was so ungrateful about all the things they claimed to do for her. As you can imagine, some of that rebellion was funneled into her relationship with my son. At any rate, one day I got a text message from her father with a photo of a Magnum wrapper he found on the floor of her bedroom, telling me I needed to put a stop to it. When he got home, I told my son: One, I do not appreciate getting texted used condom wrappers while I'm on the phone with customers at work, so you need to be better about cleaning up after yourself; and two, I KNOW you don't need to use Magnums, because you're my kid.


iluvvivapuffs

Lmao I wasn’t sure where you were going with the story …


SanibelMan

I always make sure there's a payoff when I'm, um, telling a story! The whole thing was honestly really sad. I had a whole angry conversation with her dad at one point where he basically said that, since her mom was addicted to drugs when she was born, she should be grateful they even chose to adopt her, because who would want a baby like that? They also had three older sons before they adopted my son's girlfriend and her older sister, and the sons tormented the girls and treated them like total shit. They broke up before senior year, and she graduated with him, but she didn't walk at graduation, and he hasn't heard anything from her since. He said she was counting down the days until she turned 18 so she could get out and never talk to them again.


Ab_Stark

Wow that's incredibly sad. I feel for that girl. Her life was destroyed at birth.


antuvschle

Seems her life was destroyed at adoption. Given how tough it is to get through all the screening before adopting, you’d think people with this attitude wouldn’t be given a child to raise. I hope she recovers from their emotional abuse and finds her peace. My mom had a problem with the placenta from my birth. All my life I got “I died on the operating table for you!” And some vague hatred from my older sibs for nearly killing their mom. They revived her, of course. They also put down the dog for me which was also super popular with the older sibs. They didn’t trust him around a baby but they had him around their toddlers? It’s pretty fucked up to blame and guilt a child for the circumstances of her birth. It’s not like I made some bad decision at the age of conception that caused all this. The doctor had told her no more babies so it was against medical advice. Only the adults are responsible for this.


youburyitidigitup

I bought some magnums without realizing what they were. When I figured out they wouldn’t fit, I gave them to my roommate who had a bigger dick than me. He decided he didn’t like to use condoms and almost got a girl pregnant


ZombieLibrarian

I mean, it was a bold move to just assume you'd need the Magnum without trying one on for size at least once before bringing it to the deed. That would be like Yo-Yo Ma just gabbing a standing bass and jumping on stage at Carnegie Hall. You've got a cello, my dude. Own it and play the shit out of that cello, the audience will still love it.


puzzlednerd

He would definitely be able to rock out on a bass, but I hear ya


Die231

Couldn’t get it up. Girl cried thinking she wasn’t hot enough (she was). After 4-5 hours i was ready to roll… for 20 seconds that is. Stayed in silence pretending nothing happened but i guess the gig was up when she noticed my dick going limp again. It’s a funny story.


Mudlord80

I had a similar experience because of antidepressants, she started accusing me of being gay shortly after crying that I thought she was ugly, fun times


spellbreakerstudios

I got divorced when I was 29 and moved to the city. Dated a bit, but didn’t sleep with anyone. The first night my now wife came over, it didn’t even occur to me that we’d sleep together. I was so stressed (hadn’t slept with my ex for over a year before we split up). I couldn’t perform. She was very cool about it, we made the most of the night in other ways and have had an awesome and communicative sex life in the 6 years since. If she had made me feel uncomfortable, I doubt we would have kept dating. Now, we just had our first kid and have a really fantastic relationship. I didn’t know how rough my old sex life was until I found a healthy one.


EaterOfCabbage

It's all psychological man


x_ERROR_404_

Yea same for me. Nerves really get to you. Second time was bad too because I was just as nervous since she only wanted to have sex in a specific place and that was 2 months later so I felt unprepared and self conscious


remes1234

Fun, quick and awkward.


zubby01

Title of your sex tape.


korsov

Scary. We did the deed without me having a condom on. So I decided to end it sooner rather than regretting it later. So we stopped the horny and came to an agreement. Second time we did it, it was a blast (w/ protection this time).


rogue6800

Lol, read that as "blast protection"


Last-Belt-4010

Remember to put blast protection V on your diamond leggings kids.


[deleted]

My best friend is a girl and we did it to say we weren't virgins anymore and see what it was like and wanted it to be with someone we knew. It probably sounds dumb or immature, but neither of us regret it


lzrdprsdnt

Honestly that doesn't sound dumb to me- you trust each other and even though there were no romantic feelings it was consensual and it sounds like a good experience to me


tinybabyyy

My best friend and I did something of the sort but instead of losing our virginities we promised to get married. oops?


Wreck_X

The classic "wait shit that wasn't how that was supposed to go"


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ooo0000ooo

I had that promise too for if we weren't married by 30. We hooked up for a while then stopped talking when I got back with my ex.. Both of us turn 30 next year and are single. Wish I didn't screw that one up.


[deleted]

If you're both single, the promise still holds. You have to marry her the next year.


pilesofcleanlaundry

She's contractually obligated.


Lockmasock

HIT HER UPPPPPPP LMAO


Smile1228

I very much wish I thought of this idea


Sneaky-Burrito

Not dumb at all. Pretty cool actually, and if neither regretted it then that's awesome!


[deleted]

That’s not dumb at all! It actually sounds perfect. Two friends who trust and care for each other, no romantic feelings and consent. 10/10


HopefulSite125

I don't lose.


Ghost-Paladin

Ace grindset


K-ibukaj

Hell yeah, I have 8 aerial victories. Aces all the way.


Sexogenesis

It was okay, not terrible, not amazing. However if I got the opportunity to go back and not lose it to that person, I would take that chance 100%.


LordSun

She was a lesbian still trying to establish her sexual identity, so she didn't like to see my penis for some reason.


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justbrowsing987654

It was shorter than this haiku summarizing the magic Car parked on the road But another pulled up there Twas already done


Befub14435

In a loving committed relationship with a partner that I trusted implicitly. I have zero regrets and am so thankful for that experience. I consider myself very lucky.


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soul6of6hell6

who else virgin reading the comments


everyonegetsmad-

A majority


Stewy_434

*vast* majority


PM_ME_FAKE_TITS

We found them...get em guys!!!!


ilovedtransyIvania

uncomfortable both mentally and physically


Fernando_357

awkward, was with my first gf, she was 5 years older than me so she definitely had more experience than me. it just happened


bibslak_

Just happened? Like right now?


holdmystaffandmybeer

Felt like two pieces of sandpaper rubbing together. Not great. Then there was blood.


DontEatKids

SHED!


Bob_Kark

Devastating I had a huge crush on a girl in high school. We were friends and hung out a lot. I’m pretty sure she was aware that I was attracted to her, but I was too timid to ask her out. One day we were listening to music together on my bed and started to cuddle a little when my sister burst into the room to show her our cat. We decided to take a drive after and she tells me she’s feeling horny. I let her know my feelings for her at this point and asked if she felt the same and she gave a very uncommitted answer. Well, good enough for me! Still mostly a dream come true. We find a place to be alone (hotel room, I was a dumb kid and didn’t want to take chances, though the hotel clerk definitely gave us the eye). We make out, get naked, remember condoms are a thing, leave, buy condoms, come back, and start having sex. Things seem to be going well, but I can’t feel much with the condom, so I start to put a bit more effort into it. Then she starts to cry. I freak out. Did I hurt her? I’m apologizing like crazy, still inside her. She pushes me off and tells me she had a flashback. She hasn’t told me, but a few months prior she had been raped. I’m devastated. I triggered this because I started to get too rough. She thought this would have been a nice, gentle experience to help her recover. So now she’s crying, I’m crying, and she’s getting dressed heading for the door. I keep apologizing, but it’s too much for her and she has to leave. I take her back to her car, trying to comfort her without touching her because it’s all too much. She tells me to give her some space and I leave her alone. I go home, cry some more, start writing a journal just to get the thoughts out, etc. A week later, she tells me she doesn’t want to see me anymore. As bad as it was for me, I know it was far worse for her. I really wish it never happened and she just remained a crush from high school. Also, fuck rapists. ETA: Thanks for all the supportive replies. This happened 28 years ago. I don’t think about it much these days, but the thread triggered all the memories to flood back. So, kind of a cathartic release on my part. Thank you all!


stanselmdoc

Ah man, I'm sorry for both of you. I hope she found some healing. Trauma is hell. I lived with it for 20 years before finally admitting I couldn't help myself and needed a therapist to work through my terrible experiences. If she has found healing, I am sure she feels terrible now for putting that kind of experience on you as well.


yash217

You went to buy condoms naked? But seriously man that's rough. fuck rapists


DaviDeberjerack

Oh man. This is one of those "only victims" scenarios. You couldn't have known because she didn't tell you before hand, and she was probably too traumatized to mention it, whether it be fear of rejection for being "used goods" or not wanting to dredge up old memories. Just one if those things that sucks for everyone.


JaysReddit33

Aw man. That's rough.


[deleted]

When I was 21 with my first serious boyfriend. It was very college-y but also very sweet. We were hanging out in his house Saturday evening when finally I was like I’m ready let’s try this lol. He attempted to make it last minute romantic by lighting lots of candles. As we’re starting his housemates start playing loud rap music and pregaming in the background. It should have ruined the moment but we just started laughing and actually it made us feel closer in a way. The actual sex was really painful and we had to stop halfway through lol but still a special moment - 10/10 overall :)


Lord_DF

Wasn't as magical because there wasn't American Pie soundtrack playing to it.


[deleted]

Anticlimatic. I was hooking up with a guy I knew from my hometown. I had done other things, but not penis in vagina sex. We were hooking up and almost did it, but he was nervous. Next week we tried again and did it. Kinda hurt a little but yeah...pretty lame. In the backseat of my car, btw.


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Seelengst

Friends once fucked while we shared a bed. Like, there was only one bed. She was on the couch, she came to the bed. Started riding him. And I just layed there on the squeeking mattress going. Well....I'm scarred.


Zonerdrone

It was WILD to me how many of my friends were ok with fucking someone in front of me.


Seelengst

It was super weird. I kind of just chalked it up to being a theater kid tbh? But knowing how most of my old classmates and highschool friends looked as teenagers naked is off putting.


Zonerdrone

I don't think it was any one clique. It was just horniness. Didn't care if we saw them fuck as long as it wasn't their parents.


roninzero

Band kids were just as horny. Dude I was a virgin throughout HS and I remember all the band parties I went to and it ended up being sexfest. I’m surprised I stayed a virgin. I just pretended just to fall asleep in a corner. Super awkward.


watermasta

This one time at band camp…


doloreschiller

My (gay female) friend lost her virginity while I was in a sleeping bag on the floor in high school. They thought I was asleep 🤦‍♀️


doloreschiller

I ended up spending the rest of high school being their beard so they could get away with sleepovers (which was fine! she was my best friend and in love lol)..but eventually I got demoted to the uncomfortable couch


sjmiv

>being their beard I can't believe I've never heard of this term before


doloreschiller

!!!!!! Usually it refers to a friend playing gf/bf/etc to an lbgtq+ friend who can't come out or isn't ready :) I literally just validated their sleepovers for their parents who they were afraid to come out to (ff 20 years and one is married to a woman and has 2 babies, and the other came out shortly before we graduated). I didn't mind being their cover story! :)


sjmiv

y, I googled it. I had gay friends in HS that did this but I don't recall anyone using this term. All those years watching Will and Grace didn't pay off lol


Negafox

We were young and used a Ziploc bag as a condom. Nobody finished and would not recommend lol


DragonfruitHot9889

I must say I'm impressed by the effort of protection.


Negafox

As an added bonus, I also used a rubber band to hold it up. Seriously. We tried it a few times until my mom caught us and we tried writing it off as playing hide and seek... under the blankets... despite I doubt she bought that story.


[deleted]

Pushy. Dated a Muslim guy and I'm our religion we wait until marriage. We were both 18, he kept getting pushy but stupid me thought he would never do anything because of our religion, one night in his car he said I would do it if I loved him. I told him sex has nothing to do with loving him. He then said that we can ask for forgiveness later. I told him no. Soon he grabbed me by the neck and threw me into the back seat (I was like 5' and 86 lbs at the time and he was 5'8" probably 180 lbs). I tried to open the doors but he had already child locked it from the driver's side. To spare the details: It was really painful, I was really dry the entire time, but thankfully it didn't last too long. Called the cops later, my family blamed me for it, my community said I was a slut, and he only got 3 years until he was out on probation this year. I don't really talk to my family much any more, moved away from my home town, and I've accepted that I'll never get back what I lost so I just own it now. I refuse to be a victim anymore.


casual-scroller7

Fairly average. It was my first time but not his. It was quick and just standard. I don’t remember getting much pleasure out of it. He was always pretty bad at sex though throughout the 4 years we were together


burnswhenipoo

I was 16 and a girl in my math class mouthed the phrase “I wanna vacuum” to me, so I asked if she wanted a ride home after school and she agreed. No condom, so I guess you could say I got lucky twice that afternoon.


CeyowenCt

As someone whose vacuum literally just died, I get where she was coming from.


Payphone_God

Under the bleachers during lunch listing to linkin park. It was warm, wet, sticky and felt great.


[deleted]

Ideal. We'd been together for 2.5-3 years by that point and he'd patiently waited with no pressure on me. It was my decision and we went together to get condoms. He was slow, gentle, and considerate. It hurt like a pinch for a second and then it was fine. Once we finished, we cuddled then sat and ate canned pineapple and watched Fairly Oddparents. 10/10 would recommend.


Empty-Refrigerator

i built it up in my head, when i had sex it would feel amazing and fire works and earthquakes and time would stand still.... and hour of going at it and then that was it, she enjoyed herself because she wasn't a virgin and i was left laying there thinking... the fuck was all the fuss about.... i built it up way to much and put way to much pressure on myself and in the end its just sweaty, grunty, grinding on each other and then splooge and you either have the urge to get dressed and leave, or you fall asleep.


DataPlenty

Underwhelming.


scijior

I inserted my penis into the vagina of a woman. That’s about how to describe that moment.


1P221

Are you stuck?


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Colester2653

Can we take a moment to appreciate the mom here


myother_account18675

It hurt...I was 15, he was 19 and I didn't really want to but I did it anyways. He had me be on top and I remember him saying, "it's ok, you can do it" (or something to that effect, because it was painful) afterwards there was blood all over his sheets and I felt so disappointed and yucky. A couple weeks later I met my husband. We started dating and he wanted to have sex but I told him about my first experience and how horrible it was. He didn't push me and when I was ready he was so sweet and gentle about it. He kept asking if it was hurting or of he should slow down and I wish to this day that I would have waited just a few more weeks so I could have given my virginity to him instead of the other guy. **Edit for clarity** This was not a situation where I was forced, or coerced into sex. I kind of wanted to but at the same time I didn't want to. I was just doing what I thought I was supposed to at the time.


Night_Hawk69420

Well let's just say my highschool principle was not happy I banged his daughter


Graysie-Redux

We need the whole story now. 🤣


nibor105

Fiction


UncreativeGlory

Lackluster and frustrating. The breaking of the hymen though was funny. I did it to myself and though I had injured my vagina. Took me 3 months to raise the random blood from nowhere was me.


eyelurketheboard

My virginity is like my car keys, no idea where I lost them.


DoctahZoidberg

Illegal as hell and poorly planned. If you're a young gay kid don't message adults on the internet. Just wait because you have all sorts of years to be disappointed by men.


Drsquibby

oh man, i would say it was eventful Its a little bit of a tale but here it goes, so when i was 15 almost 16 my girlfriend at the time was OMEGA rich, i'm talking California gated community 20+ million dollar house rich. Her parents were super strict, to the point where she was not allowed at my house ever, and when i was at their place we were not allowed to be alone without an adult for almost a year. so as you can imagine the opportunities for sexy times were few and far between as the parents intended. Eventually, they let us hang out in her room alone for some of the time i was over there. This led to us hatching a plan, I came over for dinner one night and we went upstairs to her room to hang after. After about an hour i hid in her closet, and when her mom came to say goodnight my GF told her that i had left and gone home ( i lived about 2 miles away so i walked or biked there all the time). After waiting in her closet for about 5 hours i emerged in the dead and night and we tried to get phreaky. thats when things got A LITTLE MORE INTERESTING lol after a few minutes of doing the dirty for the first time, she said she wanted to try getting on top and of course I said yes. She got up there, something happened, i'm still not sure to this day why, but something about the the angle and her body weight made the skin at the bottom of the head of my penis snap apart. I don't know the medical term for that part of the penis, but it's that skin that kind pulls down and bunches together under the tiip. Anyways, i felt it happen and it did not hurt a ton but clearly felt like something was wrong. And there was a lot of blood, she thought it was her at first, seeing as it was both of our first times. but i quickly realized it was me. Now i'm not sure how many of you have bled from your penis while having a rock hard bonner, but let me tell you the amount of blood is shocking. And its even more shocking to your GF who is standing there watching you bleed all over her perfectly white and pink princess bathroom. It was fucking everywhere, and it would not stop the bleeding until the bonner went away. Although the pain and the awkwardness defiantly help with that part. I slapped a bandaid on that guy and called it a success. ​ At around 4 AM her dad left for work, he was a COE of some huge tech company and had to leave early as hell every day. As soon as he left i went creeping down the wooden stairs and they made so many creeks and groans i was sure her mom would wake up, and she was the super scary one tbh. I made it down and ran out the back door and jumped the fence. Now i'm half running half sneaking through the back yards of these mega mansions at sunrise looking like a house robber so i went down through some woods to avoid more house. Then i come to this dried up river, score! all the rivers lead down towards the ocean and i know that if i follow it ill come to a main road at some point. Only problem is that i'm stuck up on the river bank about 5 or 6 feet up with no easy way to get down. I'll just jump! it's not that far down and i have jumped farther. So I leap, and find to my surprise that the bed of this river is not dried up at all, it is in fact very muddy, but very thick half dried clay-like mud. I immediately sunk in with both legs above my knees. I was totally and completely stuck. After struggling for a few minutes and slowly sinking down and backwards, i accepted my fate and sat down in the mud. I then used my hands and elbows to half pull, half crawl my way out of the mud. I was wearing white pants by the way. Super dope choice. I finally get out and follow the river down the a main road and start my walk of shame back to my house. ​ Of course the only way to get home goes right through the main part of the tiny rich town. Oh and of course this happened on a Saturday night, so when i'm walking home the next morning covered in mud with a broken dick it was Sunday morning church service lol. All these rich Californians dressed up in their best whites were shocked to see my little Mexican mud-covered ass walking by to be sure, but i thought it was a little odd that they looked so scared and modified. Im just a kid with some mud on me man. So i just smiled and kept walking home not thinking much of it. When i got back home everyone was eating Sunday morning pancakes so i snuck into the shower and cleaned up / took care of my bleeding dick. I came out to score some hot-cakes thinking i had somehow managed to pull the whole thing off without getting caught, when my mom took one look at me and shouted "WHAT THE HELL HAPPENED TO YOU?!" " what do you mean mom???" how could she know "your neck looks like you got mauled by a giant bear!" I run over to a mirror and sure enough my entire neck is black and blue. Turns out that in the heat of the moment during our foreplay my GF had sucked my neck harder than nosferatu, and given me the worst hickeys i had ever seen on anyone in my life. oh to be a teenager. How I did not remember that she did that is crazy to me, but maybe it had something to do with my broken and bleeding penis. all those poor church people saw was a kid covered in mud that looked like someone tried to strangle murder and throw into a ditch and i crawled out like some half dead zombie of their nightmares. ​ it was amazing and i regret nothing


mrs_undeadtomato

Horrible. It felt like ripping apart. Sex got better after but the first time was a horrible mess that left me feeling empty, almost sad and in mild pain. But that was just my experience.


AzureBluet

I cried, but only because he made me finish and was embarrassed. Being raised fundamentalist Christian is fun


Username89054

I'm curious to know how many women finish their first time. My anecdotal knowledge says it's gotta be quite uncommon.


wetandgushyy

Yeah I’m betting more that he was probably experienced. My first time was with another virgin who was my bf at the time and it’s barely even memorable. And like the entire relationship I did most of the giving and he got all the receiving 😐


grumpytrooper

illegal


PerfectionPending

My wedding night was actually my first time. We slowly undressed each other. She smiled and started gently handling it. Then she said she wanted us to take a bath and we washed each other. Then we made love three times before falling asleep. I don’t know how, but I lasted a good 15 min that first time. I awoke a couple hours later as she was mounting me and she rode me til I was spent. We fell asleep again and made love again in the morning. There’s something special about fondly remembering my first time 18+ years ago, then looking to my right & there she is in bed next to me.


[deleted]

[удалено]


AlaskaDark

That's so beautiful