Everyone involved was 18 years old when this happened. It was our senior year of high school. I was enjoying a warm Saturday, it had been a full day of drinking cheap beer outdoors, smoking cigarettes, and of course smoking weed. I had fallen asleep for a couple hours in my friend Kevin’s basement. Woke up shortly after dusk and I went upstairs to raid his parents’ fridge. My buddy Jeff is there in the kitchen, more people had been around earlier but it was down to just us three now. I’m feeling good, still slightly buzzed and enjoying some deli turkey straight from the pouch, when Kevin bursts out laughing and I hear him say into his phone-
“Kailey said she will do what?”
A smile takes hold of my face. I think of Kailey’s thin frame, tiny waist, blonde hair, and sexy curves. She usually came to school in tight jeans or shorts that showed off her ample ass. On top she’d have on a little spaghetti strap that showed her belly button, and a push up underneath that made her tits pop. Kevin is just outside the kitchen, on the deck, smoking a cig, and continues into the phone-
“She lives where? Ah that’s fucking deep.”
I’m not totally following the conversation at this point. I have an inkling what it’s about though because Kailey was known for being a a total slut. Several of my friends had already fucked her or been sucked off by her. Some were more willing to admit it than others.
I barely knew Kailey myself but had also heard more rumors about her reputation from a group of girls Kailey hung with. I happened to be tight with a few of them. They told me about the stream of creepy older guys she brought around and banged regularly. I was, and still am, very much turned on by this promiscuity. My virgin brain was attracted to the idea of this beautiful body that eagerly fucked so many dudes with such reckless abandon. Social stigma be damned, I had zero fucks under my young belt and was actually turned on by the idea of sticking my cock where quite a few others had been before. And here I sit now, years and 1000s of fucks later, and I am still just as turned on by this. Funny how your first time can really influence your tastes later in life. But I digress.
“Oh what! Wait what!” Kevin comes inside grinning and is slapping the kitchen counter now, really getting worked up over what he is hearing through his cell “Maggie will too? Maggie and Kelly? Uhh, I don’t even know what to say. Hold on.”
I don’t know who Maggie is, the name doesn’t ring a bell for me. But when Kevin tells me both her and Kailey are willing to suck him off for a ride to their friends’ Sarah’s house, I start trying to picture what she looked like anyways.
I end up imagining two Kailey’s simultaneously bobbing up and down on his cock. Then Kevin’s mood seems to change on a dime and he says he’s not interested. He’s still got them on the line, but he’s covering the phone now with his hand, talking to me, telling me how far away Sarah’s house is, something about gas too.
I look to our other friend, Jeff, who doesn’t have his driver’s license yet. I was his ride for the day. He’s just sitting at the counter, shaking his head at the absurdity of this offer, looking pretty tired from all the beer we had had earlier in the sun. But he quickly breaks out into what I can only describe as giggles when I utter-
“Fuck it. Tell them I’m down.”
Kevin gets back on the phone. He’s now more excited than ever. “I’m with Banks and he’s down. You still at the beach? Alright awesome.” He hangs up quickly and says let’s go. I realize that my car only has room for me, Jeff, Sarah, Maggie and Kelly. I mention this to Kevin as I put on my shoes, I gotta give Jeff a ride home, so Kevin should just stay here at his place. Jeff lives near me, and my house was on the way out to Sarah’s.
“Are you kidding? I’m not fucking missing this.” Kevin says. “I’ll follow you in my car.”
Now I’m laughing because Kevin just turned down head from these 2 girls under the loose pretense of his time being precious and gas being expensive. But hilariously, he now can’t resist following me. He’s right behind me as we pull up to the beach parking lot.
It’s dark but I can tell that the girls are all still in bikinis as they approach my car, towels on their waists and beach bags in tow. Kailey gets in first, kinda stumbling, then Sarah gets in, appearing more sober, but I am sure she had been drinking all day. Sarah and I go way back. I had known her since preschool. We had been really tight for a couple years in elementary school, although we had gradually fallen in with different friends and grown somewhat apart since. She has gorgeous, thick, curly, black hair. Her face is perfectly symmetrical, like a model’s, and she has pale white skin but strikingly dark eyes and eyebrows. Her tits were big and she had really wide hips.
I’m getting a good look at all of Sarah in my rear view mirror as she scrunches into the middle seat. She wasn’t exactly skinny, but far from fat either. A couple rolls visible around her midriff but the way she carried herself you knew she could care less. She was sexy as fuck in that bikini, and she smiled as she greeted me and Jeff.
“Hey Banks! Sup Jeff! Is that Kevin’s car behind us? Oh my god!” Sarah realizes and bursts into laughter.
I start telling her how he didn’t want to miss this, and I turn to Maggie to introduce myself and take my first look at her as I also greet Kailey. Maggie is chubby but with a really cute face, she has those doe eyes, perky cheeks and a really small nose. She also had straight brown hair, a massive ass, and some of the biggest tits I had ever seen.
Maggie also appears to be mostly sober, but it’s crystal clear Kailey is still drunk when she continues telling Maggie about a guy we know from another school named Greg. They had fucked earlier today, near the beach, in the bushes, and Kailey treats us all to her unprovoked recollections of Greg’s penis. Mainly how it was too small to be satisfactory for her.
If I didn’t have an erection already, I was certainly rock hard now.
We had made it a few blocks away from the beach and I turned onto a quiet street and parked, Kevin in his car, right behind mine. There was some back and forth between me and the three girls about whether this was actually gonna happen as I shut off the engine, Jeff gets out of the front seat and leaves to go sit in Kevin’s car, it’s clear this is too much awkwardness for him to handle. I turn to look back at the three of them and summon all the courage I’ve ever known, so that I can find the conviction to stay firm on my position. Without a blowjob from both of them, this car is going no further.
A bit more hemming and hawing ensues, when Sarah finally blurts out- “If you both won’t fucking blow him than I will!”
She had this gorgeous devilish look and we made eye contact through the rear view mirror. This candid exclamation of hers seemed to kick the other 2 girls right into gear, because next thing I know Maggie is volunteering to go first, as long as Kailey is willing to finish me off. Part of me wanted it to just be Sarah instead, but I certainly wasn’t going to protest.
Maggie gets in shotgun, and without any further ado I unzip and lift my hips slightly so she can pull down my jeans. I pull my erection and balls through the fly in my boxers and she gets straight to work, with Sarah and Kailey still in my backseat, just chatting. I can’t really see Kailey, who’s sitting directly behind me and is slumped down a bit, but I have a clear view of Sarah through the rear view mirror, she’s watching intently as Maggie moves her hand and mouth up and down my thick shaft. Sarah even makes eye contact with me a few times in the mirror. She gives me these sexy nods like she likes what she’s seeing and winks and licks her lips a couple times while she talks about what they drank earlier with Kailey. Maggie continues working me for a few more minutes, then she asks me if that was OK. I tell her it was great and she turns to the backseat to face Kailey.
“It’s your turn girl. Finish him off.” Maggie gets in the back and Kailey moves up front. Surprisingly, Jeff also decides to take this chance to hop back in my car. He and Kevin had been mulling around outside, I had figured they had gotten close enough to my car to look in my windows and confirm that Maggie was indeed sucking me off, without getting close enough to say, be able to to see my hard dick.
Kailey takes a second up front to pull her long blonde hair into a ponytail, and appears to have sobered up some. Jeff closes the door and settles in the seat behind me just in time to hear Kailey turn towards me and call out-
“Oh wow! You have a really beautiful cock.” Those words would have meant the world to me coming from anyone, but hearing them from Kailey’s mouth, it was like I was now the master of the entire universe.
She grasps my cut member like a baseball bat, its tip sticking up above both her tiny hands. She then takes me in her mouth and works me with twice the wetness and vigor that Maggie had just used. She was a practiced expert at this. I looked in the rear view mirror and immediately made eye contact with Sarah again. She had already been studying my expression, and was now staring back into my eyes, and this time she was shaking her head. Like boy you don’t know what you’re in for.
Jeff and her are just sitting back there talking about random shit, like this were normal. All of us just hanging out. We could have been sitting in a cafe as a group friends, eating together or something. Instead Kailey is making a seven course meal out of my cock and they are just chilling there, watching.
To me, it felt like 10 minutes passed, but it was probably closer to 2. Kailey’s skills had me at the edge, and I let her know. Jeff took that as his queue to leave the car, and as he jumps out, he alerts Kevin to the situation. Kevin, laughing uncontrollably, takes his place. I guess he really wanted to see me pop. I tell her again I’m right there and realize that Kailey has no intention of taking her mouth off my exploding cock.
I finally release my load and fire more than half a dozen ropes deep into her throat. She never breaks stride, working me with her tongue up and down the entire time and for 10 seconds more after I’ve finished. Then Kailey opens the passenger door and spits my cum out onto the street before turning back to me, seemingly horrified-
“Oh my god! Was that OK? Sorry, I normally swallow!” The backseat erupts with laughter and I tell her I don’t care and that she was amazing. She seems genuinely dismayed however and continues “It’s not that your cum tastes bad or anything, don’t worry about that. I just thought I was gonna gag for a second.” She pauses. “Your cock is really amazing.”
Maggie chimes in from the back “Yeah, it’s super nice.” My self confidence has never been higher. Kevin gets out, heads to his car and takes off. Kailey stays up front and Jeff gets back in. We continue driving towards Sarah’s place. I drop them off, then take Jeff home in near silence, and finally I headed home and smoked a bowl.
I would message Kevin and Jeff later that night and ask to keep this all just between us bros, but by the next morning most of my high school class would have heard about the ordeal. Kevin told one friend who told nearly everyone. And no, technically I didn’t lose my real virginity during this story. Just my oral virginity. Go ahead and sue me for the click bait title.
This was the first time I had ever got past 2nd base. I would end up losing my real virginity a few weeks later. The girl who ends up taking it from me, right before I was about to stick it in her, no joke I had my cock in hand and was putting the condom on, she asks me if the story about me and Maggie and Kailey was true.
Source: reddit.com/r/gonewildstories/comments/l353zp/how_i_lost_my_virginity_in_a_car_with_5_other
i guess sarrah did not join the fun :(
Did you ever get to fuck Sarah?
Saving for later
Are you going to share the real virginity story?
Epic dude!
Great story.
Extremely misleading title.