My first date with Jenn (MF, Oral) Part 1 | 2016

This story happened quite a few years ago, when I was in my mid 20’s. I’m about 6’ 2”, with short dark hair and blue eyes, and at the time I was still working out quite a bit and was in decent shape at 215 lbs. I had been an athlete in college, and still had a broad shouldered athletic build but had started to fill out a bit through the middle. I had moved after graduate school, and not really knowing that many people in the city I moved to, I gave online dating a shot. It worked well, at least for hooking up. I honestly was trying to find a long term girlfriend, just like it said in my profile, but often I’d go on dates with these girls, I’d realize they weren’t a girl I’d be interested in settling down with, but my dick would over-rule all other decision making processes and decide it was going to get wet tonight. And often it did.

Jenn was one of the girls I met online. Either Match or OKCupid, I can’t remember. I met her in a bar near where I lived. It turned out it was a big hangout for people who went to or worked for the college she worked at, so she was on familiar ground. I just liked the beer selection there. I’m sure you’ve heard this part of the story before, but the girl from the internet was a little bigger than I expected. Not huge, but a little chubby. She was about 5’ 4”, had long wavy blonde hair, blue eyes, cute freckles, and a pretty impressive rack. And she didn’t mind showing off a bit of cleavage. I figured it wasn’t going to go anywhere, but I didn’t want to be rude, so I got us a pair of beers and we started in on the small talk. She turned out to be pretty fun to talk to, and flirty. So one beer become two, which then became three. I don’t know if it was just me getting hornier from the beer, or if she made some adjustments when I hit the men’s room, but her cleavage became a lot more noticeable. It looked all full and ripe and freckly, and I just wanted to bury my face in there. The flirting became pretty heavy, we both got a little touchy-feely, and I decided to ask her back to my place. It didn’t take her long to say yes.

It wasn’t a very long walk back, but a lot of feels were copped on the way. I really wasn’t even thinking about sex at that point, I just wanted to get her to my place and get a look at those massive tits of hers. We entered the front door of my building into the vestibule area. I pushed her up against the wall and shoved my tongue down her throat. In no time I was pawing at her fat tits through her shirt, and she reached down and started caressing my cock through my jeans. I broke free of her and opened the inner door to the building. I stumbled up the four flights of stairs while she pressed herself against me rather tightly.
The second we were inside the door to my apartment, she was up against the wall again and I had her shirt pulled up above her tits. I began kissing my way around the exposed mounds of her breasts that were being shoved up invitingly by her rather heavy duty bra. Her low moans urged me on. I pulled down her left bra cup and my hand drove down and into it to grab that gorgeous hunk of flesh. Her nipple was hard as a rock, fat and thick like the tip of a pinky finger. My tongue was on it in no time, flicking back and forth over it, my mouth closing over it to suck , and my teeth going in for a light nibble. She moaned louder and pulled my head into her massive tit. My left hand worked its way to the bra clasp in the middle of her back, flicking it open with a snap of my thumb and middle finger. I pushed the bra up and over her tits, watching them drop heavily out the bottom and give an enticing bounce. They were firmer than I expected. They were everything I had hoped they would be, and more. Both hands went to them, pushing them up and together as I alternated sucking on one and then the other. Eventually both nipples were in my mouth at once, my tongue sweeping back and forth across them, performing figure eights.

She was repeatedly saying “Oh fuck” while I worked her tits over, and reached down to grab my hard cock hungrily. She stroked along my length through my jeans. I forced a hand down the front of her pants and inside her panties. They were pretty soaked by now. A finger slipped inside easily, and you could hear a loud slurping noise as it moved in and out. This girl was pretty damn ready. I moved her the short distance over to my bedroom, picked her up, and tossed her onto my bed. I ripped off my shirt, and then went right for her pants. They were off in seconds, as she pulled the top half of her outfit off. I dove into her tits again, licking, sucking, and nibbling every exposed inch as her noises got louder and more passionate. I kissed my way down her stomach, working my way down to her shaved cunt. She had small lips, but they were all puffy, red, and engorged. Usually I tease girls a bit before getting down to business, kissing and licking around the whole area, but I could tell she wasn’t going to get any more worked up than she already was. I dove right in, locking my mouth around her clit and flicking it quickly up and down with my tongue as I sucked. She let out an “Oh shit”, grabbed two handfuls of hair, and locked her thighs tight around me. This girl wasn’t going to let me stop any time soon, which was fine because I wasn’t planning to. It didn’t take long for her to start breathing raggedly, her repeated “Ohs” building higher and higher. Then she stopped breathing and locked onto me hard. When she released her held in breath a few seconds later, I could feel her pussy convulsing against my chin as her hips bucked up and down, and she let out a loud “FUCK”.

I worked off my pants and boxers as I worked my way up her body. Her eyes seemed locked onto my thick hard cock as I brought my hips up towards her. She grabbed hold of my dick and guided it up to her tits and face. I straddled her as she stroked me back and forth. I rotated myself into half sitting position on the bed, propped up against the pillows. As she moved on top of me she worked herself into position with her head over my waist and my cock inches from her face. She looked me in the eyes and then opened wide and sunk her mouth down over my cock. She was good at this. Earlier in the evening she had told me that most of her friends were male, and at that moment the mischievous (and dickish) part of me decided to say to her “Wow I can tell why you have so many guy friends.” She took my dick out of her mouth, laughed, called me an ass, and slapped me on the hip. And then she buried my cock deep back into her mouth and went back to working it like a pro. I gathered up her hair and held it above her head so I could watch her go at it. Her hand and mouth worked in conjunction to slide up and down my cock tightly, and her tongue rolled around my shaft and head on every withdrawal. All the noises she had made earlier had gotten me pretty worked up. That combined with her all-out assault on my genitalia had me ready to come in short order. I gave her a quick warning, and I heard and felt a hungry moan around my cock. And then I began to shoot load after load of cum. She pulled me from her mouth after the first or second pulse and continued to stroke me all over her big firm freckled tits.

She worked back up to my chest and I grabbed her by the hair again and pulled her in for a kiss. She told me she was a mess (which was no lie, she had baby batter from chin to navel) and asked where the bathroom was so she could clean up. I gave her quick directions and collapsed back into bed. After a few minutes my cock began to stir again. I was still horny, and it’s not like her display of skill had left me unimpressed. I decided I needed more. I pulled myself up and out of bed, and worked my way over to the bathroom. The door was open, and I could see her in the mirror just finishing cleaning up, wiping a few last drops of gooey white cum off her stomach. I pushed open the door all the way and moved toward her. She turned around, and she looked just as horny as I was. We sank into each other and started making out hard. I began sucking her tits again, and she reached down and stroked my cock to full mast. I grabbed her by the hair on the nape of her neck and pulled her in for a deep kiss. She moaned and kissed me back deeply. All it took was a gentle nudge and she moved to her knees in my tiny bathroom. She was eye to single eye with my trouser snake.

My cock was back in her mouth again, and I have to tell you it still felt fantastic. She sucked hard, looking up at me and showing me the hungry look in her eyes. I reached down and palmed her huge tits, pinching her nipples with my thumbs and forefingers. She moaned into my dick as I saw her hand slip between her legs. She was a good girl. Definitely a hook up and not dating material, but worth the time and effort. I held her head in place with one hand and started to move my hips back and forth, fucking her mouth slowly as she worked my thick cock. She was flushed bright red under those freckles, and moaning again. I didn’t bother to warn her this time, I just held her head in place and pulled out of her mouth. She stroked me hard as I began to shoot jet after jet of cum onto her face. A big glob hung off her chin and as others slid off and onto her tits. I was well into my post-orgasmic calm when it was interrupted by a punch to my hip.

“Ow, you came in my eye, you prick.” Sure enough, I had. A big white blob sat right there on her closed left eyelid.

“Oh shit, I’m sorry Jenn, let me get that.” I ran a hand towel under warm water while she told me how much it stung, and began laughing about it lightly. This was not the first time I had done this. It’s not like it’s on purpose, but you cum on enough girls, which is a particular favorite of mine, and it’s bound to happen. Like a dozen times or so. But I apologized a few more times, and helped her clean up. Next thing you know we were cuddled up in bed and deep asleep.

We ended up hooking up a few more times, including one that involved her workplace, which is really the interesting part of this whole relationship. The reason I told this story is to get to the next one, which is how I managed to have sex in the control room of a major university ice hockey rink/arena. Let me know if you want to hear that one, I guarantee it will be worth the price of admission.