r/prematurestories

▲ 45 r/prematurestories+2 crossposts

3 times now

For the 3rd time in 2 weeks I have came handsfree in my pants. This time was with some encouragement from someone on here and it worked perfectly by focusing on the fabic of my undies rubbing against me.. I think im on the road of ruining my stamina completely. I wonder if I have already passed the turning back point? If I keep this up, which I would like to do, I cant imagine i would last anytime at all of someone actually touched my penis again.

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u/Sseven5 — 24 hours ago
▲ 71 r/prematurestories+2 crossposts

My boyfriend wont stop cumming to quick

I 22(f) and my boyfriend 23 (m) have been together for 3 years when we first started dating he had trouble lasting and would cum usually after 1 or 2 minutes i figured thats after time this would improve however it seems to have only gotten worse now at best i get one or two thrust before he starts to cum and thats if he even makes it in me.

I was wondering if there is anything i can do to improve his stamina as im starting to get really frustrated he has not made me cum once in this entire relationship and yet brags to his friends about out amazing sex life.

I also have many stories about him to share if you wish to hear those

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u/Rich_North2508 — 5 days ago
▲ 31 r/prematurestories+1 crossposts

First Time Excitement Too Much

True Story of me a few years ago now (m26)

I was visiting a friend on a chill Thursday afternoon, both of us bored and on a whim we decided it might be fun to hit a strip club (my first time ever). We picked a random place nearby and ended up at a cheap, trashy, and mostly empty strip club.

The second we stepped inside hearing the sexy music, feeling the taboo excitement, my cock was hard before I’d even seen a single dancer, nervous arousal flooding me. After we paid and walked into the main room, it was almost empty, just a couple of girls walking around serving drinks and one on stage half naked with a couple of guys around it. Still, the raw sexual energy of the club had my blood pumping. I didn’t even find most of the girls particularly attractive, but it didn’t matter. The atmosphere alone had me throbbing in my jeans.

We sat at a table, chatting about the girls and our types, getting our drinks, and taking it in together. I was starting to calm down when my friend decided he wanted to get a private dance, so he went off to find a girl while I sat alone, nerves rising again. I was planning on just chilling, waiting for him to come back but the awkwardness hit hard. Sitting alone perving on girls felt so creepy. So I went to the bar and ordered a drink, hoping the alcohol would loosen me up.

I was halfway through it when a girl approached. Sexy tall, thicc girl, brunette hair, pretty face, and what must have been E cup tits emphasized by her tiny low cut top. My type normally being small and more petite though I still loved some tits, her body here though, in that hypersexual environment, and actually talking to me! I was captivated immediately. At first the conversation was light and casual. Where are you from? How’s your day going? I figured she was just bored because the place was so empty. I answered honestly, saying I made it clear I was just here with a friend not really interested in anything.

It was actually pleasant. I felt myself relaxing as we talked. When I finished my drink though the dynamic started to change. She started talking faster, more dominant. Before I knew it I was ordering a shot and another round for both of us. She kept me on the back foot just agreeing with everything she was saying as the conversation quickly turned more sexual. What I like about her body, what turns me on, have I ever seen big tits like hers before. All the while emphasizing those big soft tits, inviting me to stare and enjoy them. Finally she asked the trap question, "have you ever had a lap dance before?" We both knew the answer, but she was waiting for the invitation. When I said no, she was ready insisting I needed to experience it, getting up and pulling me towards the back private rooms. By that point I was fully in her rhythm, tipsy, awkwardly nervous, and so hard. I barely resisted for a moment before letting her lead me toward the private rooms.

Inside the booth I sat on the chair awkwardly even sitting on my hands as I didn't know what was allowed as she kept up the energy not giving me a moment to breath. Showing off her massive cleavage now not subtly at all she again asked if I liked her big breasts, if they would make me hard to which I enthusiastically agreed and was rewarded with her pulling her top down letting them spring free. I was stunned, for the first time in my life seeing massive tits fully exposed before me in a place I was not expecting full nudity to be allowed. She must have been enjoying how infatuated she was making me as I sat there sitting on my hands, whole body besides my cock which was continuing to throb dumbly frozen because she then asked, “Want to feel them?" My hands slowly rose to enjoy those huge, soft, warm pillows as my cock continued to throb harder. My shy reserved handling not enough for her as she grabbed the back of my head and led my face down into them, smothering me between those big fat tits and locking in my new big tit fetish forever.

Then the song ended, new song starting signifying the start of my dance. She told me to sit back and enjoy as she stood up and started dancing. I tried deep breathing to calm my throbbing cock back down some as she turned around finally hiding those triggering tits from me only to be replaced with her sexy hips and fat ass as she started dancing. Now moving to the music I was again entranced by her body. So turned on as she moved so sexy, rolling her hips, bending over letting her tiny skirt ride up and giving a full view of her fat ass shaped so sexy by her tiny thong. All the while she kept talking, sexy, playful, and teasing. Most of it blurred together as the music, her sexy body, her voice, the alcohol, and my pounding heartbeat made my head light.

After about a minute she again went further than I thought was allowed. After shaking those hips right in front of my face she sat down instead of standing back up. Her big, soft ass settled onto my lap with my now surprised hard cock now leaking as it felt these heavy pillows envelope it through my pants. I instantly was panicking now feeling very real worry of this being too much as this pleasure felt so good. My light pushes trying to get her off me and escape this pleasure were ignored as she dominantly began grinding up and down the length of my hard cock trapped in my pants. She moaned softly saying things like, "You like this don't you", "We can keep going for as many songs as you want" and "Fuck you feel so good under me"

She could clearly feel how hard I was, but she had no idea how close I already was. I was fighting with everything I had not to cum, trying to ease the pressure by shifting my hips, but she was relentless. Expertly working her ass against me, keeping the friction perfect and constant. Then she said it,

“It’s almost like we’re fucking.”

That was it. My brain short circuited. I tried again to push her away hoping I could still save it but it was useless as she came back from my weak push with one last grind down my helpless cock. I came hard, thick, messy spurts flooding the inside of my pants. The first song not even close to ending as her nervous client paints the inside of his pants with cum after maybe 30 seconds of grinding. She definitely wasn't expecting it as she kept grinding for a second longer even as I again tried to push her off.

Then she realized and the mood flipped instantly. The sexy tease vanished. She was suddenly pissed, calling me a dirty fucking pervert for cumming in my pants during her dance. I sat there ashamed and still half-hard, soaked and stunned, with no idea what to do. I pulled out money to pay for the dance. She looked at it and shook her head. She told me it wasn't enough, that I need to pay extra for being a dirty pervert and cumming is not allowed.

She marched me straight through the club to the ATM, made me withdraw another hundred as a fee, then left me standing there in my cum soaked pants. I walked back to the table, my friend was already there though looking questioning at me over what just happened. Feeling another wave of horniness from my eager cock I answered honestly feeling a wave of horny humiliation from telling my friend that I came halfway through my first lapdance and had to pay extra for it.

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u/Life-Consequence-353 — 9 days ago
▲ 68 r/prematurestories+1 crossposts

[M]y first date with Ali and first blowjob

Me at the time: 18 years old, 6 feet tall, athletic build, long curly hair, 5 inch long cock and slightly above average girth. At the time inexperienced virgin (as you’ll see), having only kissed two girls and never had anything besides my trusty hand touch myself. This is around 20 years ago and as true as I remember it.

This story takes place around 2007. When I was younger, I was pretty decent at hockey. Not professional good by any means, but junior hockey and D3 level good. Which lead me to making a junior hockey team a few hours away from my home and had just moved there. Dorm rooms, tons of time spent at the rink practicing, coaching, and working to get a few extra dollars. There happened to be a scorekeeper doing the same there that absolutely loved hockey (and thankfully hockey boys). Ali was 18, brunette, shorter, and had a tight body, with proportional b cups to her thinner frame, but where she really stood out was her firm but huge ass. This was a time before yoga pants were something that every girl wore and I remember her walking around with tight leggings and her ass was just mesmerizing. Anytime she didn’t have a jacket on in the cold rink covering it up I had to tell myself to stop staring so blatantly at it. For a horny 19 year old I was constantly fantasizing about her, making excuses to go anywhere near her, and sneaking off to the bathroom to jerk off so I wasn’t walking around the rink hard.

Now I had moved to a new place, am a virgin, so obviously not the greatest with the ladies, and there’s this beautiful scorekeeper that for some reason came up and started to talk to me because we both work at the rink. Like this hot chick that I’m nervous just to be around came up and started talking to me. She wants me right? Now me being an awkward teen didn’t come to that conclusion. Even after she Facebook friend requested me (ha 2007 times) and started chatting me on Facebook messenger I still didn’t get the hint. Figured she was more into my other teammates because she had a little bit of a known reputation of liking hockey boys.

After talking for a few weeks, Ali basically had to tell me over Facebook messenger to take her to hang out after I’m teasing her about liking one of my teammates. She’s like dude I like you not them and then I got super nervous. This pretty girl likes lanky awkward me? With no experience? Uh ohhhhh. I beat my dick into oblivion thinking about her and watching porn movies to learn how to eat pussy because I have basically no experience at this point and knew I would be a disappointment.

Ali lived at home and I couldn’t bring girls to my dorm (weird rules), so we decided I would pick her up and we would go to the mall and watch a movie. Obviously I’m incredibly nervous beforehand, shave my pubes in case I got lucky, and as I had gotten accustomed to, blowing a load thinking about her in an attempt to calm myself down. I drive the 20 minutes with clammy palms and pick her up and she’s looking wildly sexy without even trying. Straight long hair, jeans that looked like they were painted on, Ugg’s (in the rain,what we were thinking back then), and a standard black t shirt. Looking even sexier than when she’s all bundled up in the cold rink. I walk her to my two door mini cooper, open the car door for like a gentleman, and drive to the mall and park in the big parking lot. It’s midweek and raining a little bit outside and we end up talking for a few minutes because we’re early for the movie (I forget what we even were going to see). The talking ended up going well and we’re about to get out of the car and go into the movie and we end up holding hands and delaying getting out of the car. Then I get confident and lean over the console and kiss her. The surprising part is she kisses back!

Now we’re full on making out in this cramped mini cooper and I’m fumbling my hands all over her. Me being a virgin and inexperienced end up wanting to take it to the next level and show her how good I was at pleasing women after studying up on some videos. So I end up climbing over the console, bringing her seat all the way back, and kneeling in front of her on the floor of my car. All of this being done very awkwardly obviously. I’m not a small guy and this is a two door mini cooper in the middle of a crowded parking lot. I didn’t expect us to do anything before the movie and even if I did it didn’t even cross my mind that I had a chance for it to this far, so we’re completely surrounded by cars.

We’re kissing and I end up shimmying her out of her tight jeans which was tough because I’m kneeling in front of her on a wet floor mat. The pants come off with her help and she has on a sexy pair of black panties that I pull to the side and start eating her out. Angle is horrible, in a cramped car, and I’m nervous and I’m sure doing a terrible job. But I just remember absolutely loving it. She was shaved smooth, wet, and I just remember how amazing she smelled and tasted. I was in heaven. It felt so warm and inviting and honestly don’t remember anything else besides being so nervous in my head to ruin it and just going through the ABCs over and over again. I don’t even think I fingered her at all, just flicked my toungue on what I thought was her clit (who knows if I was anywhere close at that point). I can only imagine someone walking by and seeing a fully fogged up car, her legs on the dashboard, in the middle of a semi crowded parking lot, and seeing a 6 foot tall guy fully clothed kneeling in a wet floor mat eating her out. Im sure it would have made their Tuesday laughing at that.

After some time, probably not much because of my nerves, and wanted to get laid I eventually came up for air and kissed her. I asked her if we could have sex and almost jumped for joy when she said we could, and then she hit me with the BUT. ‘sometimes it’s really tight and sex just doesn’t work’ is exactly what she told me. I remember it so clearly and being so confused in the moment, but my dick there hard as a rock with this beautiful pussy in front of it so I wasn’t thinking straight. I reached in my pants and took out my condom and slapping on my condom in a hurry and dropping my pants down and trying to lose my virginity. She’s just in the passenger seat and I’m kneeling in between her legs. I end up trying to insert a few times with no idea how or where to put it being my first time and she got the hint and took her hand and tried to guide me in. I’m pushing a few times and nothing happens and she’s just like ‘yea sometimes it doesn’t work’. Kindof defeated I didn’t really know what to do. I was so close to getting laid and tried lining up a few more times with no success. I ended up slinking back over into the drivers seat.

I’m all sweaty from being nervous, the cars hot and fogged up, and I’m hard as a rock in the passenger seat. Ali gives me a sexy look, reaches over to the drivers seat and for the first time in the night starts playing with me. I get a little nervous and look around and see how many cars are around us and now am fully aware of how fogged up the car is while hearing doors opening and closing in the parking lot because I can’t even see through the fog in the car. I’m basically on edge from being in public and being so risky, it being my first time, and so turned smelling her sweet scent on my beard and in this tiny car. She’s much more experienced than I am and starts slowly rubbing my frenulum with her thumb after reaching over. I think she figured out that I had no idea what I was doing sexually and that I was holding back from cumming and thankfully wanted me to be able to savor it. She just took her time with her hand and barely stroked me and in my head celebrating that I had came right before I left and she let me adjust having her touch me. After a little bit of just resting her hand on me and slowly massaging my frenulum, she leaned over and started lightly blowing air on my head.

Now I’ve never had a blowjob and I have my hand reached around feeling her ass that I’ve dreamed about for weeks, so this slow teasing was driving me insane. With her bent over the console I could see how soaking wet she was and dipped a finger in her pussy and took it to my mouth to taste her again and tell her how much I loved tasting her. She moaned an approval and then agonizingly slowly put her mouth on my cock and began massaging my frenulum with her tongue. With the nerves and whole situation I was able to last through the handjob but when she started the blowjob on me I had no chance. She knew exactly what she was doing and wanted to finish me off now so started bobbing her mouth up and down while adding a hand. I just held onto the car with my left hand and her glorious ass with my right and just exploded after whimpering out that I was going to cum. Ali didn’t miss a beat, didn’t even react, and just kept going in unison with her mouth and hand while I exploded into her mouth. It felt like ages of me cumming and just unloading into her while my whole body was tingling and shaking.

I remember just feeling completely exhausted with this huge smile on my face. Just sitting there tingling while massaging her ass cheek with what seemed like the only strength I had left in my body. Absolutely no idea what happened after that. She turned my mind and body into complete mush. We definitely didn’t go watch the movie, and ended up dropping her off with my whole body feeling sublime after that out of body experience.

Do you think that Ali and I ever hung out again after that performance?

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u/Amk32389 — 14 days ago

Soft Ass, Hard Regret (True Story)

The theatre was nearly empty.

She sat close enough that the heavy, soft curve of her hip rested against mine the entire second half of the film. Thick. Warm. The black jeans did nothing to hide how plush she was—every small shift of her weight pressed that fat, yielding flesh more firmly against my thigh and the side of my dicklet. I could feel the slow give of it, the heat seeping through the denim.

Halfway through she leaned in a little, voice low.

“Sorry… I’ve put on a bit of weight lately. These jeans are getting too tight. I keep having to pull them up.”

As if to prove it, she shifted in the seat, reached back, and tugged the waistband of the black jeans higher. The heavy weight of her ass had already started dragging them down, the fabric stretched so tight across her cheeks that the waistband sat lower than it should. She had to dig her fingers into the denim and haul it back up with a small, embarrassed little wiggle.

I was fully hard before the next scene even started.

No hand. No deliberate tease. Just the steady pressure of her thick hip and the faint scent of her skin rising every time she leaned forward. My pulse hammered in my throat. I kept my eyes on the screen, jaw locked, but every tiny movement she made sent another heavy throb through me. By the time the credits rolled I was already leaking, the front of my underwear damp and sticky.

We stood.

She walked ahead of me down the aisle, out through the lobby, and into the cool night air. I stayed three steps behind on purpose.

And that was the end of me.

Those black jeans stretched obscenely across the biggest, roundest, softest ass I had ever seen—high, full, and heavy, the kind that sits out in a perfect, thick shelf. Each step made it roll and bounce: the deep cleft between her cheeks clearly outlined, the lower curve of each cheek jiggling with a slow, liquid weight. The waistband had already slipped down again from the sheer weight of her ass, exposing a soft strip of skin above it. Her long dark hair was pulled back in a high ponytail that swayed with every movement. The white top had ridden up just enough to show more of her lower back.

I couldn’t look away.

My dicklet jerked hard against the tight fabric. One more heavy sway of that massive, soft booty as she stepped off the curb and the pressure snapped.

I came right there on the sidewalk, still walking.

A sudden, helpless spurt soaked through my underwear and left a dark, spreading wet patch across the front of my jeans. My hips stuttered once. My knees almost gave. A quiet, choked sound escaped before I could stop it. The climax was sharp and short and completely out of my control—just the sight of her ass moving in those too-tight black jeans had finished me.

She glanced back over her shoulder, ponytail sliding across one cheek, that small soft smile already there.

“You okay back there?”

She slowed her pace so I could catch up a little, eyes dropping briefly to the front of my jeans before meeting mine again, gentle and a little shy.

“Hey… you’re shaking. Did my ass really do that to you?” She reached back once more, tugging the waistband of her jeans up again with a quiet, self-conscious little huff. “I keep telling myself these are fine, but they’re not. They keep sliding down because… well. There’s just more of me back there now. I’m sorry if it’s too much.”

Her voice stayed soft, almost apologetic, even as she gave her hips one small, careful sway and kept walking.

“You don’t have to be embarrassed. I kind of like that you couldn’t help it… just from watching me walk.”

 

Later that evening I sat on the edge of my bed, still replaying every second, and finally texted her.

Me: Hey… I’m really sorry about earlier. That was so embarrassing. I didn’t mean to finish like that just from looking at you. I feel like an idiot. And I’m honestly sorry I wasn’t brave enough to just make a proper move. I really wanted to give that gorgeous booty of yours a proper slap while we were walking… I just stuffed it up. Sorry :/

The message showed as delivered. Then read.

I stared at the screen for a long time. No reply.

Ten minutes. Twenty. Almost an hour.

Every time my phone lit up with some other notification my stomach twisted, hoping it was her. It never was. She had seen it… and just left me sitting there with the embarrassment and the wanting.

Finally, well past when I’d given up, her reply came through.

Her: Don’t apologise 😊 I meant what I said. I kind of liked it. The fact you couldn’t help it. It’s actually pretty hot knowing my ass (even with the extra weight) can do that to you so easily. You’re into bigger girls… I can tell. And honestly? I’m not complaining. For the record… you should’ve just slapped it. Next time don’t overthink it. Just maybe warn me before you make a mess in public 😉😊

I typed back immediately.

Me: Well if you’d given me even the slightest green light instead of acting all shy about the weight, I would have slapped it. Next time don’t make it feel like I’m the one who has to guess. And thanks for pretending not to mind that I finished so fast 😆 You have no idea how good that soft doughy fat heavy ass looked in those too tight jeans 😏

The message was delivered. Then read.

And that was it.

No reply. No typing bubbles. Nothing.

She left me on read again. The soft teasing words from her earlier message still sat there on the screen while I waited, phone in hand. I was already desperately hard from the memory of her walking ahead of me, that heavy soft ass swaying in the too-tight jeans.

I pushed my pants down and wrapped my hand around my dicklet, stroking slowly at first, replaying the way it had bounced with every step. But the longer the silence stretched, the more the regret crept in. The gaslighting lines I’d sent started to feel stupid and mean. I should’ve just owned the embarrassment instead of trying to twist it back on her.

Still, I kept going—faster now—eyes locked on the unread chat, wishing I’d never hit send, wishing she’d reply, wishing I could take the words back while I stroked myself to the thought of the very ass I’d just blamed her for.

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u/Sad_Employment9106 — 10 days ago