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Hailie and I were friends for years, we had been in a large circle of friends in college, and moved about an hour away from each other after graduation. Some people in our group had dated or hooked up, but Hailie was always adamant to keep things from being too complicated and never did. We barely spoke about things sexual in nature, but I knew she was never looking for a hookup or FWB and even had a 7 date rule. Sheâs always very bubbly in real life, but itâs easy to tell that sheâs a prude and while she doesnât get uncomfortable hearing about sex, she would never start that conversation.
Hailie is undeniably cute, short and curvy with big green eyes and a loving smile, but she always dressed very conservatively and therefore was never hit on or picked up. And Iâm sure that seeing her modest pictures on dating apps discouraged any guy looking for just a hookup as well. While she had many friends who would set her up on dates, things didnât seem to progress or last, as she wanted something very specific and never seemed to find it. All this adds up to one thing⌠a very very needy and horny 25 year old girl.
I was one of a handful of guys who were invited to her birthday party, and the others were already salivating at the prospect of being in a small party with such a female heavy ratio. We all met up in a bar and I was quite shocked to see that the girls were nothing like Hailie at all! It was not yet winter but Hailie was wearing slacks and a cardigan, most of the guys were wearing polos or button down shirts, but half of her friends group looked like they were ready to go clubbing. Their outfits barely had enough material to mop up the drool from all of the guys in the otherwise quiet bar.
We all sat around and reminisced, while the newer friends added in their own stories, and someone brought in a homemade âwho knows Hailie betterâ game. It was all fun and light until we started talking about Halieâs lack of sex life, and some of her girl friends were really giving her the gears while the guys just looked on, unsure how to respond. It was the opposite of slut shaming and Iâve never seen it before, but itâs definitely just as wrong. Eventually someone changed the subject and the rest of the night was light and fun again.
I ended up driving Hailie home afterwards because it was on the way to my place and the conversation got deep, real fast. âDo you think guys donât want to date me because I donât want to have sex right away? Am I wasting my twenties not hooking up? Do I dress like an old milkmaid?â The questions were fast and furious, and it was hard to focus on the driving and satisfactorily answer her. But Hailie seemed content with my answers and just said âthank youâ before grabbing my hand and lapsing off into a long silence. It was our first âintimateâ contact and I just decided to go with it.
But the next time Hailie opened her mouth, the questions were directed at me, as she definitely didnât know any of the details, but she knew I was more on the promiscuous side of things. âDo you get feelings for a FWB or hookup? Would you seriously date a girl who you knew slept around?â Those were harder to dance around and I did tell her that guys and girls have different emotions after sex too. She seemed to be content with those answers and then started to tell me her sex history. Three guys, all former boyfriends, never anything kinky, barely oral, and she had a vibrator to keep her from being sexually frustrated during her last dry spell, which was now close to two years.
There was a lot to get my head around, but basically Hailie had never experienced spontaneous, wild, passionate sex. She started asking me about my sex life, and then asked me what was the kinkiest thing I had done. I didnât know how to respond, but I had started writing my stories out, this was long before posting on Reddit, and just handed it to her with the notes open. âRead it if you want, it has everything.â Spellbound, Hailie took it and started reading.
I was only about ten minutes away from her apartment at the time, and Hailie stayed in the car for a few more minutes after that, just reading and holding my hand. Finally she looked at me âAre these true? Youâre a great writer regardless.â They were all true and half of them were sent to the girls afterwards, so they could cum again to the memories. Hailie just looked at me and said âI donât know if Iâm ready for birthday sex, but would you please give me a birthday kiss?â I didnât even respond and just leaned over to kiss her cheek and forehead, but she just looked at me with those big green eyes while massaging my hand with both of hers and said âa real kiss.â
A real kiss it was. I leaned over and held her trembling chin in my hand before placing the softest kiss on her pouty lips. It took all of three seconds for Hailie to go from chaste kiss to attacking my mouth with reckless abandon. Her hands were in my hair and she moaned into my mouth while her tongue pushed itself as far as it could go. âCome inside and kiss me properlyâ she whispered as she gasped for air. I followed, trying to tell myself to not let this night go too far, but ultimately, she was in charge.
I sat down on her couch and Hailie immediately straddled me to kiss me and grind into my growing erection. I was not able to hide how hard I was and it made her growl and moan in excitement. âTouch me, feel my bodyâ she said and she didnât have to say it twice. Her curves were soft and they were soon being gently caressed as we kissed passionately. Hailie wanted more and growled at me to squeeze her big tits, grope her ass, and enjoy her like Iâve never enjoyed a girlâs body before. She might not have had any experience riding a guy, but she certainly knew how to grind while on my lap, I was so hard that I tried to hold her down and keep her still because otherwise it mightâve been too much for me.
My hands were inside of her sweater and teasing her rock hard nipples when Hailie said something that made me freeze. âUgh letâs just have sex already.â I wanted it almost as much as she did, but I knew I wouldnât regret it nearly as much as she might. I looked at the clock- 11:47 on the eve of her birthday. I told her that Iâm going to the car for 13 minutes and I will text her happy birthday at midnight. She can decide how she wants to respond then. She looked a little thankful and a little disappointed but kissed me one last time before getting up and leading me to the door.
I sat in my car and waited while contemplating all of the possible repercussions from this. We both knew that we werenât going to date seriously, we were friends but had very different ideas and life plans. Conversely, I felt that Hailie would least regret having sex with me of all people, and knew that I would treat her right and put her pleasure first. I texted her at midnight exactly and waited for a responseâŚ.one minute, three minutes, six minutes. I was just about to leave when I got a text back- âSorry I lost track of time, please come backâ followed by a picture of her tv open to the Netflix Home Screen. I walked up the stairs again and thought about where I knew this night was going, and made sure that I had a condom.
Hailie opened the door with just her head poking out and told me to come inside. Every idea I had about conversation first and making sure she really wanted it went out the window when I saw her naked body. I closed the door behind me and she jumped into my arms to kiss me again, while I felt her still damp skin and realized how exactly she lost track of time. It was a quick shower and I wanted to taste her fresh skin, every inch of it actually, and told her so. She just laid down on her bed and spread her legs before stopping my forehead as I was about to dive in. âBet you never thought this would happen, huh Mister?â No I did not. But I was determined to make sure that it would be a night for her to remember.
Hailie was already wet and slick, and I pressed my face against her muff, inhaling her scent. She had a full bush, and I appreciated the shower, as I had never eaten out a full, thick bush like that before. It was a little bit tricky to avoid painfully pulling any hairs, but I quickly caught on and spread her lips so I could lap at her clit. Hailie was needy and her moans filled the room while she used words like cunt and fuck which I had never imagined would even be in her vocabulary. Soon enough, her vocal cords were relegated to emitting unintelligible sounds of pleasure as I sucked on her engorged clit.
Halie came and pulled me up to kiss her before asking me what I wanted to do next. I told her that she chose everything that we did and didnât do, and was shocked that she immediately said âI want to suck your dick.â I was not going to turn that down and smiled as she eagerly pulled down my undies before taking as much of my throbbing cock into her mouth as she was able. I was already so close from the previous grinding and humping the bed while I ate her out (also puts more head movement into cunnilingus so a win-win) and it only took a few minutes of those soft lips on the head of my cock before she was choking, and then swallowing all of my cum.
We kissed and cuddled through the refractory period and Hailie asked me if I wanted to go get a condom, before laughing when I pulled it out of my pocket. She knew that we had all chipped in together for a gift but still made sure to tease me for giving her a condom as a birthday present, but then opened it and slid it onto my already hard again penis. âIs it ok if we just do missionary?â She asked sheepishly, but I kissed her and assured her that it was more than ok, in fact, it would be perfect. And when I crawled over her and slid her ass over a pillow before lining up my raincoat clad cock with her soaking wet pussy, âperfectâ was the word on her lips as well.
Hailieâs arms went above her head and clasped the slats of her bed frame while I slid into her tight pussy. âItâs been so long⌠you feel so good⌠come close⌠perfectâŚâ she babbled while I thrusted, gently at first, before picking up speed and rhythm. Finally her arms wrapped around my back and she whispered into my ear while I filled up her neglected little pussy. I was able to go for a while after cumming, but we kept it slow and she had another orgasm while we made love, and then she told me that she wants to watch me cum for her. I was more than happy to oblige and got on my knees and yanked off the condom while she got a pile of her dirty clothes for me to cum on, which was incredibly sexy.
Hailie got on her knees next me and ran her hands up and down my abs, kissed my shoulders, and squeezed my ass while I stroked my cock, aiming directly at a flowery pair of panties. She mightâve felt too self conscious to talk dirty at that point, but still told me over and over that she wanted to watch me cum, cum for her, and cover her panties. I was getting close and she encouraged me to moan, telling me how much she loved hearing it while raking her fingernails over my bare skin. That put me over the edge and I came all over her clothes, getting that pair of panties with most of it, but some dribbled on a t shirt as well. Hailie gave the head of my cock the cutest little kiss and simply said to me âThank you, it was perfect.â
I offered to stay over the night but she declined and texted me the next day that she was still on a high, and asked me to write it up for her as well. We hung out plenty of times during the following year and never even kissed, it was like our one special night and we never mentioned it, aside from the occasional joke of waiting in a long line or something, it was so long âit felt like 13 minutes.â But the following year she had a party with her girls and then texted me the next day, asking if we could just hang out alone. I headed over and was ready to pick her up when she came out of her room in a green dress and holding a little bag. It was wrapped, and inside was a 3 pack of condoms and a printed out copy of the story I had written for her, with her handwriting at the end saying âto be continued.â
We tried a bunch more positions that night and she wrote the part two afterwards, but refused to send it to me. You just read the story which I wrote for her with a few details changed and omitted. Furthermore, she was the one who told me to post my stories on reddit, and I guess she lurks here, so maybe sheâll see this one and add a reply:) thank you for all of the upvotes, comments, and follows!
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