[M]y [F]irst One Night Stand Went Bad, then Sideways, then Much Worse

This was years ago, I was just entering the scene after a long monogamous stretch. I was talking to this chick online. She only provided one picture, looked like a Linked-In head and shoulders shot. She was very attractive, in a ‘handsome’ sort of way, with long, straight blonde hair. She’d told me she was taller than most guys, so I assumed between 5’8 and 5’10, and from her picture, I could tell she was solidly built. (Not fat, just big shoulders, big hips, muscular arms.)

She was very aggressive in text, constantly telling me how good looking she was, that when she went to the gym all the guys stared at her, that she knew everyone wanted her and she could have her pick of guys anytime she wanted to. It felt like she was trying to convince herself of that, but I didn’t know enough about her to tell what her backstory was, perhaps she had been in a relationship where he had abused her mentally, insulting and talking her down.

Along with her high opinion of herself was a lot of innuendo and sexually charged talk, and she was smart and engaging. On the other hand she was had a lot of man-hate built up, every guy she dated only wanted one thing, every guy thought they were great at oral but none of them were, those types of things. As we talked, I actually began to LIKE her less and less, but definitely wanted to see her naked, and, thought that there was a chance that in person she would relax. The online act felt like an act of extreme chutzpah that might lighten up face to face.

So I had been at dinner with friends, and she’s blowing up my phone. Finally, as I drive home she texts “I’m sitting here alone and I’m touching myself. Does that make you hard?” Well ten minutes later we’d arranged that I’d go over to her house and spend the night. She was adamant about “No intercourse” but clearly orgasms were on the menu.

However, safety is not an accident. For the first time in my life, I gave my whereabouts to a friend, telling her that if I didn’t text her again by 7 am, come looking for me.

I get to Ms Aggressive’s house and she’s looking GOOD. She’s wearing a very tight white t-shirt, see her bra very clearly through it, and a pair of super tight nylon athletic shorts. Long, smooth, muscular legs, and as I suspected, a solid, very fit body. Very hot, she exuded sex in every way, but she was taller and probably heavier than me, that was a little unnerving, never had that experience before.

We had small talk for a few minutes and then she stands up, shoving her croctch at my face and says “Let’s go to the bedroom”.

True to form with her aggressive demeanor online.

We dropped on her bed, fully clothed, and started making out. I was hard instantly and she spread her legs so I could grind against her in those very thin nylon shorts. That lasts for about 2 minutes before she starts taking my pants off and I of course respond, we’re down to underwear immediately. Remembering her ‘every guy thinks they’re great at oral but they’re all horrible’ insistence, I make sure to work my way down south slowly, and begin my ‘kiss around the panties’ move but she’s having none of it. Less than a minute in, she flips me over on my back and crawls on top of me, 69, and buries her crotch in my face while she tries tugging my boxers off with one hand and reaching for my cock with the other. She was wearing white granny panties, full coverage everywhere, so it’s challenging to pull them off while she’s trying to suck me. That was awkward for a moment, it’s like she didn’t want to lose a second with my cock in her mouth.

Finally she relents for a moment, getting off her knees and letting me tug them down to her ankles, and kicks them off while she’s still got my cock in her mouth. In the dim light of the room, I am now face to face with the biggest bush I’ve ever seen – and she’s late 30s, so I was not expecting that at all. Furthermore, the mane of blonde hair didn’t jive with the thick black hair facing me, ordinarily I would have expected blonde and definitely not as bushy. Not a natural blonde? Or just a rarity.

Anyway, I’m starting to see why her previous partners hadn’t been successful with oral, I realize I’m going to spend a LOT of time just finding the goods, much less being able to get down to business. But she is really impatient and squirms, and at the same time she’s sucking me like there’s a time limit. It doesn’t take me long to come, and she’s really sucking hard, stroking me, squeezing my balls, trying to get me to come as fast as she can. So I don’t have time to get her warmed up before I blow into her mouth, and when I’m done, she immediately crawls off of me, and says, “See? I told you that every guy says they love eating pussy but nobody ever makes me cum. You’re no different than the rest.”

So that pissed me off, she was just being a bitch. I was very turned on by this massive bush, I wanted to spend a lot of time down there, exploring and playing and seeing how to best please her. There was a lot of potential treasure. But she was the Domino’s version of cunnilingus: Make me cum in 5 minutes or you’re done. We fall asleep next to each other, but no pillow talk, no making out, no touching, no cuddling.

The next morning I wake up to hear her in the shower, and then she comes out, wrapped in a towel, to see if I’m awake. I don’t think she said anything. I was still pissed from last night and just wanted to get out of there so I mumble something and then she goes back into the bathroom and I close my eyes again.

So the next morning I’m still sleeping, I feel her wake up and get out of bed, hear the shower go on. I doze. The shower goes off and a couple minutes later the bedroom light go on, so I turn on my back, open my eyes, and there she is, wearing a towel wrapped around her, just barely covering her chest, showing off those amazing legs all the way up to ‘there’, and her hair up in another towel.

She very definitely came in to wake me up, but as we didn’t fall asleep in a good way, it didn’t feel like an amorous scene, rather, almost accusatory. I mumble hi and she answers, “Just seeing if you were awake yet.”

She goes back in the bathroom and I close my eyes. A few minutes later I hear her in the bedroom again, open my eyes, and this time, oh my god.

The towel is gone, now she’s just wearing a pair of bright white waist high panties and nothing else. Her long blonde hair is draped over her shoulders, and her tits, holy shit. I knew she was stacked from the night before, but never really got to see them, with our immediate jump to 69 and then to sleep. They were AMAZING. They were perfect. Very large, well formed, just enough sag to be ‘real’, large aerolas, distinct nipples. She was a work of art, the epitome of a 40s centerfold.

Waist high granny panties had never been my thing before, but as I looked at her, I was suddenly so turned on. She looked perfect. I looked at her in amazement, and obviously my shock and admiration registered, she put one hand on her hip and said “See something you like?”

I stuttered for a second, and replied with what I was thinking, “You are incredible. You’re the model for every 1940s pinup every done.” I very purposefully slowly looked her up and down, adoring her body with my eyes.

“Wow. Just wow.”

I could feel myself suddenly grow under the sheet.

“Well that’s nice to hear.” She stood there, and I realized she was enjoying being stared at, so I did my best to look her up and down, in very careful detail.

“You’re enjoying the show?” She asked

“Uh, yeah. I’m getting really hard all of a sudden.”

“Yeah?” she said in a sort of disdainful tone. “Show me.”

I pulled back the covers, and exposed myself, my cock now completely erect, laying against my stomach.

“Yeah, that’s what I expected. Men like the way I look.”

She was back to being aggressive and confrontational, but DAMN! “Well count me into that group. Nice…..”

She stared at my erection while I continued to look her up and down. In response to her looking at me, I got harder and harder, until it lifted off of my stomach and began to quiver in mid-air.

“Whoa, you really are enjoying the view.” She arched her back a bit.

I said “hell yes!” I looked her up and down one more time, and then told her to turn around, slowly, using my finger to indicate a twirling. She was a little taken aback at my taking charge and telling her what to do, rather than being a pussy and hoping she’d be good to me. “Really?” I nodded sternly, and reinforced my request. “Yes…” She blushed for a second, and then did as I told.

She slowly turned, stopping at 90 degrees, to show off her silhouette. Then she continued, until she was facing away. She tugged her panties tight against her ass, the thin satin virtually glued to her ass, showing every curve. She stopped, and looked over her shoulder. That’s when she saw that I was lightly touching the underside of the shaft, encouraging it to throb.

“Oh, touching yourself?” She tried to sneer.

With that, she spread her feet apart, and slowly bent over, until her shoulders were even with her hips, giving me a perfect view of her ass, her bright white panties disappearing between her legs, her pubic hair creating a slight mound the crotch, visible from my point of view.

She tugged her panties again, causing them to ride up between her cheeks a bit as well, as well as creating a slight cleft between her folds, even despite the substantial bush covering them.

“Keep stroking. You know you want this, don’t you?”

“More than you know…” I answered with a grunt

“Oh, I know. Every man wants to fuck me.” She stood back up, and continued her pirouette until she was facing me again, and I put my hand down as she completed her turn.

I noticed that her tits seemed to be a bit fuller, more swollen, her nipples now hard, and the dark bush between her thighs definitely visible through her panties.

“You’re not touching anymore.” She stated.

“Well, I know you have to get ready for work.” The polite me had returned. “Yeah, I do. I don’t have time to suck you again. Besides, why should you get all the fun, you didn’t get me off.” I paused. “Hey, I’d love to try again. You’ve got an amazing pussy. You didn’t give me enough time.”

“No, I have to get ready for work. I told you nobody can ever get me off.” She shrugged, then looked back at my cock, still throbbing. “Nice that I’m giving you a good time though.” She laughed, in a slightly mean way.

I looked her up and down again. “Would you mind if I masturbated while watching you get dressed?”

She did a double take for a moment, wondering if she had really heard what she thought she heard.

“You just want to do yourself? You don’t want me to blow you again?”

“Oh I would much rather you do your magic, that was amazing last night.” “Yeah, I could tell how I turned you on.” She shrugged. “Hey, if you want to stroke your cock while looking at me, go ahead!”

She paused for a second, and added, a little more softly, “That’s really pretty hot. I would like to watch, actually… No guy has ever wanted to just jack off looking at me.”

“Welll they’re insane. You’re incredible.” I slowly moved my hand to my shaft, now upright, standing away from my stomach again, and started to lightly touch the underside again.

“Don’t take all day, I do have to get to work you know”

She watched for a moment as I ran my fingers up and down the shaft, then turned to her dresser. Opening a drawer, she pulled out a bra, some socks, and turned again. “I suppose I shouldn’t put this on yet, huh?” holding up a matching bright white lacy brassiere.

“I’d rather you not, if that’s ok. Do you have anything else to do before you start covering yourself up?”

“I have to do my hair, but I have to go into the bathroom to do that.” She waited for a moment, and I wrapped my hand around the shaft and began pumping firmly.

She started walking toward the bathroom, seeing my eyes follow. “I’ll be right back”

She returned in a moment, with a comb and brush, and began brushing, then combing her massive mane of blonde. As her arms moved, her tits jiggled, and my eyes followed. “You like that, huh?” Her eyes moved up and down, tracing the motion of my hand.

I wrapped the fingers of my other hand around my balls, and began to squeeze in concert with my pumping. It wasn’t going to take long to climax now.

“I have to curl the ends, I need to go back in the bathroom, can you hold off until I’m done? I want to watch you cum.” she asked, a lot more agreeable suddenly.

“I’m pretty close. I’m just so turned on looking at you.”

“Give me one minute.” She disappeared, then was back in just a few seconds, holding her curling iron. She pulled a chair away from the wall, and plugged it in. Then she sat down, facing me, and began curling the very ends, while watching me. She was a lot closer to me now, her tits nearly close enough to touch. She alternated looking at my face and my hands, and watched my eyes travel up and down her body.

She stared at my cock again, drops now visible at the tip. Back to her confrontational mode, she spread her legs apart, giving me a view of her panties disappearing between her legs again, although this time from the front. “You want to fuck me, don’t you? Take a good look at what you’re not going to get.”

I felt myself approach climax, and she realized what was happening, my breathing faster.

“You’re going to do it!”, again, with a softer voice. “You’re going to cum right in front of me!”

I looked at her half conscious, “uh, yeah.”

“Go ahead, bust all over yourself. I want to see you shoot” She put her curling iron down, brushed her hair behind her shoulders, stood up, and stepped a step closer to me, her massive tits shaking, the dark spot in her panties just a couple feet away from my face.

She reached down to her panties, and tugged them up again, creating even more of a cameltoe. Then hands back on hips and started shaking her shoulders, causing her tits to bounce. She shot me a knowing look.

I stroked harder and faster, and almost immediately that familiar tingle at the base of my cock started. My eyes rolled back in their sockets, and she knew I was there. She encouraged me to unload, and I groaned as the first burst gathered strength and then shot, followed right away with a second. She cooed at that one, a big milky glob landing on the center of my chest. Several more volleys landed in short order after, all over my stomach.

I looked at her, smiled in a daze. She looked at the mess with adoring eyes for a moment. Then suddenly her expression hardened, and she said “Yeah, I hope you remember this for a while. It’s the closest you’re ever going to get. I have to get dressed.”

She turned back to her dresser and ignored me as I laid there, a pool of cum all over my stomach. I got up and went into the bathroom, quickly wiped myself off, and by the time I got back into the bedroom, she was finished dressing. I started to get dressed and she left the room, still not saying a word. Once I was dressed myself, I went down the hall, to see her in the kitchen. “You’re parked behind me. I have to get to work.”

“Ok”, I shrugged, and walked out, not saying another word. “You can’t please all of the people all of the time, and you can’t please some of the people any of the time”, I thought to myself on walk of shame to my car.

Later that day I got a long email full of insults and reproachments about my pitiful performance in her bed, yet another disappointing notch in her bedpost. I felt bad for her, maybe she’ll find someone on her wavelength some day. It certainly wasn’t me.

Source: reddit.com/r/gonewildstories/comments/qa73px/my_first_one_night_stand_went_bad_then_sideways

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