Read my first post for context here:
Over the next week or so, following our hookup, I obsessed over Hayley. I jerked off to her instagram a lot, now having the memories of being with her to help. God, she was so hot. I really, really wanted to sleep with her again but had no idea if she felt the same way. I agonized over whether or not I should message her and eventually built up the courage to do so.
I sent her a casual “hey how are you” type message. She sent a mellow response. I tried to keep up a conversation but she seemed disinterested. She was nice and polite but made no effort to further the chat. All good. I get it. Message received.
I was pretty bummed out but not surprised. That first night with her was already too good to be true. Plus, I was happy enough with the memories of being with a girl this hot even just once. I started to move on.
Then maybe a week after my last message, I got a message from her just out of the blue. She was inviting me to some afternoon outdoor club party at a fancy bar. A different fancy bar from the one I worked at. Possibly fancier. Definitely a rich/hot girl event. Absolutely not my scene. But hell would freeze over before I would say no to Hayley. I enthusiasticly agreed to come.
Of course there was the cliche ambiguity as to whether or not this was a date. Maybe we were just friends again, like when we were kids… except now we had slept together…. Yeah, it was weird. I wasn’t sure how to feel but my dumb, horny, male brain wasn’t gonna let that stop me.
I considered bringing along a friend for support, just in case it wasn’t a date, but I decided against it… just in case it WAS a date.
When the day finally came, I was an awful combination of nervous and excited. I put on my best party shirt and shorts, (summer vibes or something) shoved a couple of good luck condoms in my wallet and made my way there.
I found Hayley shortly after arriving and WOW she looked sexy as hell. This was now the second time in a row I’d seen her and she’d blown away my expectations of how attractive she could be. She was wearing a tight black silk (or satin?) bodysuit with a short red frilly skirt. A brilliant combination of pushup bra and tight top made her tits look much bigger than usual, beautifully accentuating her cleavage. She had her signature red lipstick on and her long, bronze legs looked as sexy as ever. The girls I dream about didn’t look this good.
She greeted me with a friendly hug, giving me a strong whif of her amazing scent. It was a mix of her perfume and natural BO built up from dancing. She introduced to a few of her friends she was with. I guess it wasn’t a date? Some of the friends I recognized from the bar a few weeks ago; more hot girls and a few hot guys.
Hayley grabbed me by the hand and took me to the dance floor area. I danced with her friends for a while, not really having any substantial conversation with anyone, but having lots of fun. I was surrounded by gorgeous 10/10 girls but couldn’t keep my eyes off Hayley. It seemed like many guys couldn’t keep their eyes off her. She drew a lot of attention.
We drank, consumed a small amount of drugs and had a great time. Although I couldn’t help but wonder where I stood with Hayley. So far everything seemed to be just casual and friendly, and I didn’t want to ruin a fun night by abrasively making a move. At this point I was starting to regret not bringing a friend, as I didn’t know anyone too well and couldn’t expect Hayley to give me her full attention. That regret would soon fade.
Later into the night, things started getting messier. The sun was down and people were drunk, high and tired. I was sitting by myself off to the side of the dance floor, nursing a beer, when Hayley found me and took a seat next to me. We were both quite tipsy.
“Hey, what are you doing all alone?”
“Just taking a break.”
“Thanks for coming, by the way. I hope you’re having a good time.”
“Yeah, this has been really fun, thanks for bringing me.”
There was a silence in conversation. Hayley inched closer to me. I tried not to stare at her cleavage. She put a hand on my thigh and looked me right in the eyes. Yep, that was the signal. I moved in for the kiss. I think we were both at that level of drunk and horny where we skipped the slow romantic part of the kiss and went right into sucking face and groping each other. The release of tension I felt from finally kissing her was better than an orgasm. This intents lust had built up over the last two weeks and now I finally got to touch her and kiss her again. It was incredible.
We were too drunk and horny to care that we were completely visible to anyone who cared to look. Fortunately we didn’t stand out too much amongst the drunk and messy party. I do like to imagine many of the guys at the party were watching in envy.
I pulled myself away from her sweet lips and asked,
“Hey you wanna get out of here?”
“What? No! The night’s far from over!”
I felt stupid and embarrassed, but only momentarily. She grabbed my hand again.
“Come on.”
I followed her around to the side of the main building. We were in a dark, secluded alleyway type area, not completely cut off from the the party, but far enough that it would be hard to find us. There was a couple making out down the far end of the alley but it was too dark really see them.
Hayley sat me down on a small bench and straddled me, pressing right into my unbelievably hard cock. I placed my hands on her thighs and slowly glided up to her ass. She aggressively stuck her tongue back down my throat and began grinding on me. My hands had now moved up to her hips, feeling her amazing silk clad body. I stuck my head into her cleave and licked and kissed the top of her tits. She increased her grinding to a considerable pace, as though she was actually riding me, and started moaning. She had her hands behind my neck as she leant back for leverage. We were going at it so hard we almost fell off the bench a few times.
“Daniel, I’m so horny,” she moaned out.
“Please can we fuck,” I begged.
“God, yes.”
She paused her grinding to stand up for a sec. She stuck one of her hands under her skirt and unhooked her bodysuit from below. Meanwhile I undid my shorts and shuffled them down just enough to pull my throbbing dick out. I had completely forgotten about my condoms but neither of us cared one bit. She sat back down over me, skirt and suit still on, and I glided into right into her soaking wet pussy. She continued her vigorous grinding movements, only now she actually was riding me. I held on for dear life, in terms of both not cumming inside her and physically not falling off the bench.
She was so good at riding me and it felt absolutely amazing. She alternated between leaning back and grinding against me and the pulling herself in closer to bounce on me.
“Please, please, please, I’m almost there,” she begged, as I tried to focus on anything else. I tried to make out with her to distract myself but she was too into the riding.
“Yes, yes, fuck yes,” she moaned in a breathy voice. She abruptly stopped and gripped me so hard by the next it hurt. She started pulsating as I could feel her pussy contract in waves around my cock. Her eyes were closed and mouth wide open, heavily breathing.
I had done it, I survived. I was very proud of myself.
“THANK you,” she whispered as she leaned back in to kiss me. Honestly, she had done all the work but I’ll take it. We tenderly kissed for a bit, my cock still deep inside her. She hopped up and fixed up her bodysuit. I was pretty disappointed I didn’t get to nut but I had a feeling this wasn’t the end of our affair.
“Come on, let’s dance!” we ran back out to the party, grabbed some more drinks and kept dancing. I don’t think either of us knew where the rest of the group was anymore. We danced intimately, touching and holding each other. I was still incredibly horny and rock hard. She danced with her back to me and pressed her ass back into my crotch. There’s no way she didn’t feel how hard I was. She started teasing me, brushing her ass against me. I held her around the hips and pressed into her. I cannot express how horny I was. All I wanted to do was pound her right on the dance floor.
We danced in this position for a few minutes, getting progressively touchy with each other. Eventually I move my head right next to her’s and whispered in her ear, “I need to have you right now.”
She swivelled around with a big grin on her face and my hands still on her hips. This time I took her hand and led her back to the dark alley area. I grabbed her around the waist, pulled her in and kissed her. She walked up against the brick wall, so that her back was pressed against it. She had a big, excited grin on her face. I turned her around and she stuck her ass out at me. I pressed into it with my cock again, right between her cheek. I slowly dry humped her while I kissed her neck.
“Fuck me,” she ordered, as she put her hand up her skirt again to undo her bodysuit. I contemplated putting on a condom because I really, really didn’t want to pull out but I decided against it, as it might ruin the heat of the moment. I pulled my cock out through my fly and then poked around until I found her opening and slipped in even more easily. It was an awkward angle but luckily she was tall enough for it to work. I started pounding her fast against the wall. I had one hand around her waist and one on her shoulder. Her back was arched such that her head was bent back towards me and I could kiss her neck and whisper in her ear how hot I thought she was.
“God, you’re so fucking sexy.”
She started moaning. I was so incredibly horny from our unfinished last session that I didn’t last long. After an estimated 2 minutes I was on the edge of orgasm.
“Oh, shit, I’m cumming.”
Hayley briefly composed herself to order me not to cum in her. I obliged. I pulled out at the last minute and came somewhere under her skirt. She quickly turned back around, grabbed my cock and started wanking it as I continued cumming. It was a long and intense orgasm. We kissed some more before fixing ourselves up.
We laughed at how messy we were with cum everywhere. We went to our respective bathrooms to clean up. Seeing myself in the bathroom mirror was a shock. I looked wild, hair all over the place and red lipstick marks on my cheeks and lips.
I went back outside to find Hayley. She was with some of her friends again, sitting down in a corner. They all looked incredibly tired and ready to leave. Hayley said she was going to leave with one of her girlfriends and asked if I was right getting home. I was hugely dissapointed by this. All I wanted to do was take her home and fuck her and kiss her and cuddle with her all night. I didn’t even get to see her naked this time. But I wasn’t about to ruin a good night. I said I’d be fine to grab an Uber. She gave me a nice kiss goodbye and whispered, “Thank you.”
And that was it. I went home alone, fell asleep and woke up with a massive hangover. I spent the next day recovering and jerking off to my fresh memories with Hayley, supplemented by her sexy instagram pics.
We did have one more sexual encounter that I might write up about if you guys liked this :)
Source: reddit.com/r/gonewildstories/comments/jfudtg/mf_a_very_hot_second_encounter_with_an_old_friend
Drop the 3rd encounter asap
Very much enjoyed both your stories. Thanks.
I’m seriously hoping you finally finish inside her soon!