We matched on the well used dating app, I was instantly attracted to Jen; black hair and a slim body. It didn’t take us long to get onto naughtier chats. I was a little surprised but I was all for it, the literature graduate turned out to be a very very naughty girl.
We exchanged lots of naughty chats and more for a couple of weeks before we finally met up. We spoke about it for hours, sharing stories and what we liked to do.
I arranged the hotel and we were set.
We instantly hit it off, I immediately got her a glass of red wine, after she told me that red wine makes her so horny. I was only too happy to oblige. We chatted and flirted, got drunk and then we knew it was time.
The sexual tension was so high, we barely made it into the room and Jen’s dress was on the floor. My boxers around my ankles, my fingers on her clit as we moved to the bed, Jen spread her legs as she lay in her back and my tongue went straight to her clit. Jen let out various sighs and groans as I tasted her tight pussy. It wasn’t even a surprise how tight it looked, she wasn’t a tall girl and was so slim, her body tight and just perfect.
She pulled the bottle of lube from her bag, yes she took the lube on her first ever date with me. She passed it straight to me, she had one reason and one reason only to do this, “fuck me” she gasp and I wasn’t about to say no. I took the lube and covered my cock and her clit, not that she needed it she was wet already from my tongue but she knew I was going to stretch her, that’s not boasting. Two of my smallest fingers would have stretched her, because of the lube I slid straight in, instantly she took all of my rock hard cock – her eyes lit up as my balls slapped against her wet shaved pussy.
I could sense that it was a little difficult for her, that last inch and a half, she groaned every time that last bit slide inside her. I was on top so it was so easy to glide into her tight and wet pussy, but Jen didn’t care if she struggled to take every inch or she got used to it quickly, as she thrust herself into me, that was that, it instantly turned me on and I bit her lip, as I done this Jen dug her nails into my back and grabbed me all over, my ass digging her nails into it as I thrust my cock deep inside her. She used my ass to push me down harder, she wanted to be rough and I was all for it.
I then decided that I had something else to make her breathless, as I straddled her shoulders. She opened her mouth, she knew what was coming. I grabbed the back of her head, pushing it further and further down my cock, she couldn’t manage much at the start but after a few minutes Jen got the hang of it, she looked up at me with her beautiful brown eyes watering as I held my cock in her throat, certainly not all of it but enough to make her gag. She looked insanely hot as she looked at me with my cock down her throat.
I could feel I was getting close, I went straight back to fucking her, putting her legs over my shoulders going deeper with every single stroke, Jen was absolutely breathless, “please cum” she let out and that was enough I filled her tight pussy with my cum. She was right the red wine definitely made her horny.
We lay next to each other, fell asleep for maybe an hour. Jen woke first, she grabbed my cock and started wanking me off, I was a little dazzed but I was instantly hard and ready to go. She got on top of me and positioned my cock, straight inside her, my cum from earlier still dripping out of her, using it as lube was incredibly effective. She bounced on me for about 10 minutes before, she turned around and arched her back, she wanted it in doggy.
Jens tight little body looked amazing, even tighter in this position. I grabbed the lube and covered her, flicking her asshole occasionally. She knew I wanted to play with it, but not quite yet.
I grabbed her hips as I thrust myself inside her, she was so tight and it felt amazing. My finger slid into her ass, it was so tight as I fucked her, every thrust pushing my finger in deeper. Once my finger was as the way in, I pulled out my cock, covered in her cum, my cum and lube. Jen knew, the lube squirted into her ass, she wasn’t a huge fan of anal but as tight as her ass looked, it swallowed my cock with ease.
It felt magical, it was so tight, she took it all without any issue. She looked at me, get it back in my pussy, I smiled and let her thrust back a few more times and pulled my cock out.
I went to turn over for her to ride me again, put she pounced on my as I lay on my front. She hands massaging my body, then Jen didn’t something I wasn’t expecting. She took her finger and pressed it against my ass, no lube although I was basically covered in it anyway, I let out a groan.
This was the first time I’d ever had a girl finger my ass, I slightly arched back a bit, Jen sensed I liked it and she started to finger my ass, first with one finger. It felt sore but also amazing at the same time, Jen enjoyed it just as much she took her other hand and stuck two fingers in my mouth as she worked my ass.
I couldn’t stop groaning, then she went for two and she went rough, fingering my ass how she’d fingered her pussy, it was sore but I loved it. Jen was visibly excited by it telling me her fucking naughty I was.
The answer was, we both were.
This book loving, innocent looking woman, the first time meeting me was fingering my ass and getting off on it. I was so turned on at this point but I couldn’t take much more of her rough fingering and grabbed her and got on top and went straight back to fucking her, as hard and fast as I could, I was slamming into her, you could hear my body slapping against hers, it was Jen’s time to moan uncontrollably, I pushed as hard as I could deep into her pussy, she came as I continued to rough fuck her but she took it and loved it, thrusting back every time. I’ve never experienced someone so willing to push it to the very limit of taking every inch, she was so small and impressive.
I grabbed her ass as I slowed down, sliding a finger inside. Jen done the same to me, it wasn’t long I cummed again in her pussy.
We continued this I think 3 more times during the night, I think it was 5 times we fucked and I mean we fucked hard every time, there was no soft sensual sex it was full on. Jen fingered my ass every single time after, she loved the control and how kinky I was. She took every load in her pussy, 5 separate times.
We had to check out, I got up and looked at her, then my eyes turned to the bed, it was covered in pools of cum, every where. There were stains everywhere, it looked like it might have hurt… Jen giggled and looked at my cock and said, ‘it’s big and that was the roughest sex she’d ever had’. She got up and a load of my cum, dripped from her pussy, streaming down her legs it was so hot. I wiped it up with my fingers and put them straight into her mouth, some breakfast I laughed, Jen licked it off.
So that’s my experience with Jen the total book nerd, she read all the time and just didn’t give me the ‘kinky’ vibe but boy was she right that red wine makes her horny. I love being surprised by cute/innocent looking women. It’s so hot. Hope you enjoyed my naughty night with Jen.
Source: reddit.com/r/gonewildstories/comments/10cysub/i_thought_she_was_just_a_book_nerd_but_i_was_so