r/prematurestories

▲ 17 r/prematurestories+1 crossposts

My second time embarrassing myself

As requested, another true prejac story. I have linked my 1st story. Just a little background. I live in Sydney, Australia and here if you didn't know prostitution is legal, I won't name this girl because she is still working.

https://www.reddit.com/r/PrejacStories/s/kSh78UV8Xf

So this was about a month from my 1st story. I have worked up the urge to go see the same girl. I arranged to see her on a Saturday night for GFE. All that day, again I looked at her pictures, her slightly tanned skin, short blonde hair, toned body. I remembered her bright blue eyes, her hairless pussy. I jerked off about 1 hour before leaving. So I didn't repeat my last performance. I went to the same hotel and knocked on the door.

She opened it and I went inside. We hugged and I was excited that she remembered me. "oh it's you, maybe this time you could actually get to the fun part" she said, "it was all fun" I said trying to be flirty, "cumming on the floor was fun" she said with a sideways glance, "this time I'm going to cum on you" I said in the most awkward way possible. Unfortunately I lay awake at night remembering this painful conversation.

We sat on the lounge and spoke for a bit, I had a drink and took her in, she was wearing a flowery blue dress, it clung on her body perfectly, her legs uncovered and no shoes. She threw her legs across my lap and I ran my hands up and down then. I could see up her dress as it had ridden up, she was wearing sheer black panties, the white triangle of her untanned skin showing through. I was semi hard up until this point. Now I was rock hard and throbbing, I could feel the precum soaking my underwear. She saw me staring and told me to go have a shower so we could get to the fun bit.

I stripped off in the bathroom and saw my cock was dripping precum, it was rock hard. A quick cold shower was enough to get me off the edge. I came out and she was lounging on the bed, unlike last time, she was still dressed. My cock was soft but getting harder by the second. I can't express how hot she is and how hot I think blondes are. She came over to me and we kissed, that made me fully hard. I pulled her dress off and revealed her tight toned body. She was wearing a small lacey set of black lingerie. She sunk to her knees and lent forwards. I could feel her warm breath on my cock, she looked up at me, and teasingly ran her finger along the side of my cock, before letting her lips graze my length. That was enough for me. "oh fuck, sorry, I'm gonna..." was all I got out before I spurted cum onto her chin, neck and tits. She sat back, a look on her face that was a mixture of pity, anger and disgust.

She hopped up and went into the bathroom. "I'm sorry, you're just so hot, at least this time I didn't get it on the carpet" I said, "hmm yeah because I got in the way" she called from the bathroom, clearly not impressed. She emerged a few minutes later all cleaned up. "I ask guys to pay extra for facials, it's not part of the normal experience. So either you pay more now or we halve the time, because I don't take facials for free." she said. I didn't want to upset her and I didn't want to cut my time in half, so I agreed to pay the $100 extra for the facial. I had planned that something would go wrong, so I had brought extra money. Once I had paid her, she went back to her bubbly flirty self.

We laid on the bed and I caressed her body. She instantly brought up pre-ejaculation. I tried to play it off, oh you're so hot, I was so worked up thinking about you blah blah blah but she wasn't taking it. She asked me about other times and I lied, talking about how this never happens. She then asked if I was good at eating pussy, because I have a small dick and I pre ejaculation constantly. this was my fetish coming true. I pulled her panties off and started licking her clit. She tasted like coconut body oil. After a few minutes of licking I got curious and asked her if she experiences per ejaculation a lot, given her job, she said no, not like me, some guys last a few minutes but no one else cums as fast as me. I asked her to tell me about the normal guys, who last longer. She looked down at me "while you'er licking my pussy you want to hear about the guys I fuck?", I nodded. That got me rock hard in record time. I humped the bed as I licked her pussy and she told me about all the guys who fuck her for hours.

I sat up and showed her I was ready. She reached over for a condom off the night stand and I never did find out what she thought of my pussy eating skills. She slid it on my cock and giggled a little at the length of my cock. I'm just over 3 inches and skinny. Technically not a micro cock!

she rolled over onto her stomach and stuck her ass in the air, I could see her pretty pussy bare and waiting. I mounted her from behind. Slide my cock against her pussy lips trying to find her hole. She has a nice perky ass so this position wasn't the best for me but after a while of fumbling I felt my cock slid into her pussy. Fuck it was glorious, her pussy tight and hot. One hand on her hip the other gripping a tit. I started thrusting. I lasted about 10 thrusts or like 5 seconds. I moaned quietly as my cock spurted into the condom. she looked over her shoulder at me "What's wrong, you can't find my pussy? Lets change positions, you lay on your back." She moved forwards on her hands and knees as I knelt in place, as she moved my cock slid from her but her tight pussy took the condom. It leaked cum as she moved and slapped against her thighs. She flopped onto her back and laughed as she pulled it out, only then seeing the cum in it. "Did you cum? When?", "I came when I was fucking you" I said, "oh yeah....you didn't say anything, I was close to we could have cum together" she replied, "fuck you have a tight pussy" I said flipping next to her, "you have a really nice cock, just the right length to hit my gspot, trust me those big cocks hurt, I would rather one like yours everytime!". I chose to believe this!

Again I asked if I could keep the condom, she rolled her eyes and put it in a tissue on the bedside table. For the rest of the time, we laid on the bed chatting and watching tiktoks on her phone. We were both still naked and I loved looking at her body, every now and then she would get up and do a tiktok dance.

My time ended and I got dressed, she threw a robe on and we hugged as I left, I made sure to get my condom, front pocket this time! She asked when I was coming to visit her again, I was so worked up I said I was free tomorrow if she was. "Great how does 10am work for you?" and just like that I was going to see her tomorrow. Unfortunately my next visit wouldn't go any better.

I could tell so many storys with her, I saw her so often and still do. But I'm only telling the worst of the worst. Let me know if you want to hear more! I love being able to finally tell these stories!

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u/googoogooner69 — 23 hours ago

Came on her panties…

Hey all,

While I’ve never been a marathon man when it comes to sex, the issue has always been exacerbated by sexy outfits, lingerie, and cute panties. The sight of my girl in a sexy little skirt and thong is often enough to turn a 1-2 minute session into a 30 second session. Recently it was even worse.

We had gotten the chance to go out on the town. We were in a different city, so she had gotten the urge to really dress up in a way she wouldn’t do if there was a chance she’d see people she knew. After a long time of going back and forth between different outfits, she settled on tight top, red lace bra, matching thong, and a skirt short enough that she could barely sit without giving everyone a show.

She knows this sort of thing drives me wild, and the looks she was getting all night didn’t help. More than a few times when I was not right next to her I saw guys “accidentally” brush against her in the crowd. To say I was verging on feral would be an understatement.

As the bars closed down, we caught a ride back to our hotel. We were all over each other the entire time. I was bordering on tearing through my pants I was so hard, and the wet spot was becoming very visible.

We finally made it to our room. Before the door was even fully shut I was tearing my shirt, pants, and precum soaked underwear off. She had removed her shirt and layed back on the bed, in just her bra, skirt hiked up, and thong.

I quickly climbed on and we started to make out. My cock was desperately trying to get through her thong. I reached down and started to finger her, feeling how wet she got almost immediately. I pulled my hand away and pressed my tip against her thong. The wetness and warmth was too much…

With a moan and a weak “oh god no” I unceremoniously shot my load on her thong and thighs. I looked up to see a look of shock on her face, which soon twisted into a grin.

“Guess you really did like this outfit!” She giggled, before giving me kiss. She gently pushed me back, stripping off her thong and laying back with her legs spread. I proceeded to eat her out for 20 minutes, giving her what she needed before we had a brief makeout session, finishing up by cleaning up and getting into bed.

She cracked a couple jokes about it the next day but was sure to tell me that she loved how she could make me cum whenever she pleased.

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u/Little-Blueberry7096 — 3 days ago

Got my first blowjob and came within 30sec

I'm still feeling embarrassed but also very aroused about it. My girl, very vanilla girl I must add, had just confessed to me she would like to try give me a BJ. I must admit I was really happy about this but also a bit nervous, because we are in a relationship for couple of years and never done something like that. From the beginning she was very clear that she wouldn't do blowjobs or other stuff. because of that I do watch porn, with kinks in cuckold, interracial, chastity and also PE.. but never have thought of it happening to me.

So later that week on an evening we were making out on the bed and she hinted she wanted to try it out. I looked at her and didn't know what to say so I said let's try then.. she responded; "but tell me in time to stop!" she worked her way down and she was a bit hesitant but still she did start giving me a blowjob, I must say it felt amazing, but maybe a bit to good or I was to nervous I don't know but after a short while I guess like 20 or 30 seconds, I felt near the edge, as she was still blowing me I quickly tapped her to stop as I didn't want to break her trust! she stopped quite quickly she looked at me like "what's wrong" while I was trying my best to hold back my orgasm, she was still holding my cock and as she looked at me and moved her hand a bit and that was it, it took me over the edge she quickly let go and she actually ruined my orgasm.

she did look quite fond of herself telling me "well that's a first" and after the cum had dribbled out of my cock she jerked a bit and asked "can you go again or was this it?" I told her "yeah I can go again" although I knew I couldn't, she tried a bit of jerking me of but I couldn't get fully hard again so she said "well, i'll keep that as a rain check."

I did ask her if I let her down but she told me she was not disappointed, I'm not sure about it and we havent talked much about it, but for me this experience was quite humiliating but also I'm still really aroused by it...

I thought I'd share to take it of my chest and see if there are people that have an opinion or advice about it, she doesn't know my kinks or any of it.

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u/GnoomerComplex — 4 days ago
▲ 57 r/prematurestories+1 crossposts

Dont wake me for that.

I was feeling excited at 3am, so I turned to my wife, who was only wearing a baggy t-shirt and panties. I slid under the covers nudging her and slipped off her panties. Rousing her up a bit I did was i always do and started to eat her out to warm her up. I could feel here getting wetter and after she was ready she brought me up to her to enter.

With her still half asleep I spread her legs and couldn't see any of her body with her baggy shirt covering all of her. With visual stimulation i started thrusting. After about 5 trust of me trembling and trying my best to hold it in. She nudged me off and turned over.

After a few deep breaths i started again from behind. I was trembling holding it together and only got another 5 trust befor completlty loosing my load. All in all the whoe session lasted 30s including her changing positions and trying to calm my self down.

"You woke me for that" she mumbled as she turned over cum dribbling down her ass cheek. She quickly went back to sleep.

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u/Bright-Thought-5903 — 9 days ago

I got caught ! now she feels sorry for me

I’m 28, still single, a virgin, and have never had sex before. I mostly watch MILF porn and for a long time thought finishing in 2-3 minutes while masturbating was normal.

A few years ago I started practicing and training after reading about premature ejaculation. Surprisingly, I’ve gotten really good at it. I can now cum hands-free just from porn or captions, and I can complete 10-second or 15-second challenges easily.

Last week though, things got really embarrassing.

It was late at night and I was doing a 20-second challenge in my room. I forgot that my mom was staying over. She walked in right as I finished super fast — before the timer even ended.

The next day she looked at me with pity in her eyes and said, “Why do you finish so quickly like this, son? Have you gone to see a doctor yet?”
Then she added softly, “Is this why you still don’t have a girlfriend? You poor thing…”

I felt incredibly ashamed and awkward. She wasn’t angry, she just sounded genuinely sorry for me, which somehow made it even worse. Now every time I see her I feel embarrassed and I don’t know how to act normal around her anymore.

Even though I trained myself to be able to finish very quickly on purpose, this whole situation has left me feeling exposed and uncomfortable while mom visited at home.

Has anyone ever been caught by their parents in a moment like this? How did you deal with the awkwardness afterwards? Especially when your mom reacts with pity instead of anger?

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u/nuttoza012 — 7 days ago

20f first experience

I’m 24f now but this was my first prejac experience when I was 20f
I am 5’7 125lbs brown hair

Our first date ended in a brief makeout so when he came up to visit my apartment a few days later the tension had already been building.
He was 6’2 and very muscular I was looking forward to being fucked hard and thrown around. What I got was… less than satisfying.
When he arrived we started making out on the couch. I was surprised at how nervous he was, I was used to guys taking more control but aside from a hand on my thigh I got nothing.
I finally led him to the bedroom and I could see a bulge through his jeans. I undid the zipper and pulled him on top of me on the bed, still in his boxers he was hard as a rock. He started dry humping me and I could feel a wet spot forming from his tip through his boxers.
I pushed him up so I could slide my shorts off and he pushed his boxers down revealing his 6 inch throbbing penis. He was wet enough from precum that he slid right inside my tight pussy even though he had neglected to perform any foreplay on me.
As soon as he entered me he let out a gasp and started to uncontrollably hump me for maybe 15 seconds before letting out a loud moan in my ear while I felt his dick twitch and fill me up.
He rolled off of me still panting and said “uh sorry was that good for you?” And I couldn’t help but let out a giggle. He apologized and told me it had been a few months since he’d had sex. I told him not to worry about it and assumed it’d get better the next time.
We went out to dinner and had a couple drinks, when we got back to my apartment I was extremely horny and climbed on top of him on the couch. I started to lightly grind myself on his lap, feeling his dick straining through his pants. I was trying to rub my clit on him to give myself some sort of release, I got excited when I felt him reach his hand down and thought he was going to rub me but he was just taking his hard cock out of his pants.
He put his hands on my ass and I slid myself down onto him. Just like the first time he gasped but since I was on top I was in control. I took his hands from my hips and put them on my perky B cup boobs while I started to bounce on him. I made it up and down twice before he burst inside me.
He was so embarrassed once again.

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u/IssueRemarkable3608 — 11 days ago

Premature in the shower

Hey guys,

This past weekend my girl and I decided to take a shower together. We don’t do this too often but the mood was right so we decided to go for it.

Pretty soon my hands are all over her, my cock rapidly stiffening. She could feel this and decided to do one of her new favorite things, make me get on my knees and play with myself while she takes care of herself. We did this for a few minutes before she made me get up.

I was rock hard and throbbing, and she proceeded to turn around and bend over, taking my cock between her legs. She was slowly stroking and I knew it was all but over for me.

She pressed my tip against her pussy and gave a stroke. I almost immediately shot my load between her legs, on her thighs. She looked at her hand, then giggled and looked back, “mmm that was quick hun? Someone was a little excited, huh? Hehe”

Not the first time I didn’t even make it inside, but one of the quickest times, for sure! From her taking my cock between her legs to shooting my load couldn’t have been more than 15 seconds.

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u/Little-Blueberry7096 — 11 days ago

I came in my underwear watching BBC porn with my wife…

We were hanging out on the couch having drinks and enjoying ourselves. As we sit there the edibles kick in and my wife has the idea to watch some porn we’ve done it a few times previously. So we start watching some pretty vanilla stuff. She starts stroking my dick through my underwear as I slip a finger in her panties to tease her. We finish the video and she clicks on a suggested video which is a young blonde taking on one of the biggest black cocks I’ve ever seen.I’m fingering her as he whips his huge BBC out on the screen and almost instantly her pussy gets soaked causing my little 4inch dick to throb in my underwear. She completely naked now and props her thigh up on my throbbing hard on as she tells me to go faster. Only a few minutes pass and she’s soaked moaning as my fingers please her. Maybe it was the edibles and alcohol but she starts cumming harder than she ever has on my little cock. Screaming moaning and starts squirting hard. I’ve never made her squirt btw. Her thighs are trembling on my cock as her pussy squirts all over my underwear. Her fat DD tits jiggling nipples rock hard. I just lost it 3 days worth of cum erupts in my pants as she completely ignores my cock for the massive black cock. It was one of the most powerful orgasms of my life and she barely touched me.

I think I unlocked a new kink

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u/cuckedLoser13 — 11 days ago