Category: Hookup Stories

Okay, so here we are again. I still have a story to finish and I’m going to do it, dammit. I you need a recap, just check out the last two posts.

I did what she wanted

I made sure to suck every single part of her foot that she pressed to my mouth. I licked her toes and ran my tongue along her arch. I looked up and saw the kind of evil smile on her face that I wish I could see every single day. She must have made her point because she pulled her foot out of my mouth and spread her legs in front of me.

It was working for her

She spread her legs and wide as she could and her skirt just hiked itself up her thighs. I could see everything down there and I could tell that I was giving her exactly what she wanted. Her pussy was completely shaved and her lips were absolutely drenched in juice. Shit, if I didn’t know any better, I would have thought that she came just by having me down on my knees. She moved the yard stick behind me and pressed it against the back of my head. I knew what she was doing and I allowed her to force my face right into her crotch.

“Once again, Mr. Smith, LICK! We’ll make you a model student yet!”

I did my job

I was completely under this woman’s spell and I ate her pussy like it was the nectar of the gods. I sucked on her lips and flicked her clit. She held onto my head and grinded her pelvis into me. It was probably the best cunnilingus I had ever given in my life and her thighs closed painfully against my head when I made her cum with my mouth. I waited for her grip to loosen before I leaned back on my legs and looked up at her.

She was happy

I could tell that I had just given her an orgasm that she would never be able to forget. She was smiling from ear to ear. Her bun was suddenly messy and her glasses were halfway down her nose. She was sweating and her chest was heaving, but she still found a way to speak to me.

“Very good job, Mr. Smith. If only you put that kind of enthusiasm into your class work! Now I’ll just have to make sure you remember your lesson from today. Lean back!”

She was suddenly stern again and I did as she told me. I leaned back as far as I could. My cock was shooting straight up under my sweatpants. The fabric with drenched in sticky precum. Then she certainly gave me something to remember.

She made the lesson stick

She kept smiling and staring directly into my eyes as she slid her still naked toes under the waist of my sweatpants and pulled them down. My dick was throbbing and shot right up into the air. A slight breeze could have set me off, but she did much better than that. She wrapped her soft soles around the head of my dick and slowly stroked it with her feet. The precum was more than enough lubricant to make her skin slide up and down my member. I wish that I could say that I lasted until we changed positions, but I can’t. I don’t know how many strokes it took, but it couldn’t have been more than four. I exploded all over her naked feet and practically covered them. The orgasm was so intense that I started shaking from head to toe. The cum just kept coming and coming. It shot all over her toes and spurted all of the way up to her fucking ankle! It lasted forever and I’ve never felt so much pleasure in my life. When it finally stopped shooting and dribbling out, I finally knew what it felt like to be completely empty. I had never felt it before and I’ve never felt it since. She kept stroking and stroking until every last drop of my essence was on her foot.

The wrap up

What she did next has stayed on my mind ever since it happened. She leaned back and let my sweatpants spring back over my quickly deflating cock. She leaned forward to hooker her fingers under her heels to pick them up.

“That’s my very good boy,” she smiled. “I think I may have gotten through to you! No wonder why you could never focus in class, Mr. Smith. My poor little student has been all backed up with cum!”

“Ye.. yes, ma’am.” I was exhausted and the words just came out of me. I sat there and watched her pull her heels back onto her feet, right over the massive load of cum that I left on them.

“I’ll just keep it with me as a reminder, Mr. Smith. It’s a reminder that you’ll be the perfect for me for the rest of the semester. Is that understood?”

All I could do was nod. This woman was amazing!

“Good!” She jumped to her feet and her heels clicked on the floor. I could swear that I heard her feet squelch into the cum inside them. All she did was walk right back around her desk and sit in her chair. She threw her feet back up on the desk, straightened her glasses, and picked her book right back up.

“That will be all Mr. Smith. You may see yourself out of my class.”

And that was it

She just started reading her book again. She was asserting her dominance and there was nothing I could do about it. I just got up off of the floor and left. I was shaking for the entire drive home, that’s how fucking intense it all was. It was the absolute best roleplaying experience of my life. Now, if you’ll excuse me, I reached out to Mrs. Reynolds last night and it turns out that I’ve been a very naughty student again! She’s expecting to see me in her class tonight and I certainly want to be just a little late!

So, I just told you about meeting up with a college professor who had a thing for her younger students. She wanted a roleplay hook up and I was determined to give it to her. I was sitting in the desk at the head of the class with by erection proudly displayed under my sweatpants. This woman just yelled at me for being late and she got up to walk over to me. Of course, she took the time to grab one of those long, wooden yard sticks on the way. She was all leg and hot looking as hell.

Things got real interesting

She slammed the yard stick down onto my desk and I couldn’t stop myself from jumping. She has this naughty smirk on her face and leaned in really close to my face. I could see right down her shirt and smell her perfume. This woman was absolutely NOT wearing a bra and I could everything! I immediately got shot back into my teen years and remembered every single load that I lost to a teacher.

“You’re late, Mr. Smith. That’s far too many tardies in a row. What do you think we should do about that?”

I fucking loved it

I never thought I would enjoy female dominance like this as much as I did. There was just something about this being an actual teacher that turned me on to no end! I could feel my sweatpants getting sticky under the desk. She hadn’t even touched me and I was leaking precum like an adolescent!

“Um, um… I’m sorry, Mrs. Reynolds. I didn’t mean to be late… I won’t let it happen again.”

I stammered out the words and felt my heart pounding in my chest. She leaned in even closer and whispered into my ear. Her position put her naked tits right into my face and soft skin brushed against my cheeks.

“You’re a very naughty boy, Mr. Smith. Naughty boys like you need to be punished!”

Her hand started wandering

She leaned back so our noses practically touching. I was looking right into her eyes when I felt her hand grab onto the head of my dick under the desk. She ran her palm all over it and it felt amazing!

“Oh, what’s this, Mr. Smith? It seems that you’re all sticky under here! What could have possibly caused that, naughty boy?”

She sat back down

She let go of my cock with that same half smile on her face and turned around. I thanked God that she did. I probably would have just shot my load right there and then if she kept it on me. I got to watch her slowly walk away from me with her perfect ass moving under her tight skirt. She sat on the edge of her desk and crossed her amazing legs.

“You need to learn your place, Mr. Smith.” She said as she slowly kicked off one black high hell, then the other. They fell to the floor with a thud and I have to admit that I jumped at each one. This was a woman who could do anything she wanted to me and I would have let her. That was how deeply infatuated and turned on I was by her.

“Get on your knees, boy!” She commanded it of me more than said it. I did it as quickly as efficiently as I could. Then I just looked up at her like a dog looking for an order.

“Crawl to me.” Once again, I did it. The floor was cold, hard, and dirty, but I did it. I actually crawled on my hands and knees until I was right in front of her and her desk.

“That’s a good boy.” She half whispered to me. I had no idea what to expect until I felt her naked foot press against my chin. She exerted pressure and I took her cue to lift me head to look at her. She still had that sexy fucking smile that had me hypnotized and submitting to every order. Her foot was soft and pretty. She ran it across my forehead and down my cheeks. Then she placed it right over my mouth.

“Your place is beneath me, Mr. Smith. You must understand that. Now, lick!”

Next time

Phew, that was a lot, even for me. I’m remembering more details that I thought I would. I’m going to have to save the rest for next time. I don’t think I can keep going on without trying to call this woman up and seeing what she’s up to. Actually, maybe I’ll just do that right now. It couldn’t hurt, right? Maybe a trip down memory is just what I need right now!

I’ve been trying to remember all of my favorite hook ups to share here. I’ve had a lot of them, but there are always going to be a few that stand out. The last one I remembered was all about roleplay and it was a whole lot of fun. I can’t say who it was with, but I can certainly say that she was a college professor. It turned out that this professor was really into her young students. They were all of age, so she could have actually had sex with them, but it would have affected her job. Having the dean find out that you’re actively dating your 18 year old students is never a good thing. That’s why she turned to a roleplay hook up and I got the part.

She was into something very specific

She set up the whole thing and I just stepped into the role of one of her students. She had something very specific in mind and I was determined to give it to her. She told me that a lot of her male students would just roll out of bed and head into class in sweatpants or pajamas. That was easy enough, but it got really specific for her. A lot of times, these guys would show up to class with their morning wood still proudly at full mast. She’d watch them walk through the door with giant hard ons poking through their pants. That was what really turned her on in the morning and she’d be wet all day long afterward. It was the first task assigned to me and I was determined to make it as real for her as possible. I drove to the college in by rattiest T-shirt and loosest sweatpants. I got to the door of her classroom. The entire building was empty because this was way after hours. I looked around and stood in front of the closed door. Then I reached into my pants and started jerking myself off right in the hallway. I was pretty excited for what was going to happen, so it didn’t take long for me to get hard. It was only after my dick was visibly erect under my pants that I opened the door and walked right in.

She was ready for me

I made my way into her classroom and she was sitting at her desk, just waiting for me. She really had the whole sexy teacher thing going on. Her hair was up in a bun and her glasses were those sexy librarian glasses that always got me hard. Her feet were up on the desk and she has this tiny little skirt on. Her blouse was open just enough to show off her perfect cleavage. I could see right there why her students were always hard. I didn’t even have to jerk off outside. All I had to do was take one look at her and I would have been at full mast without even trying. I sat in the desk closest to hers and she didn’t waste a single second. She slammed her book down onto her own desk and yelled “You’re LATE!” I knew I was in for something special.

Next time

My time is short and I really want to be able to remember every last, sordid detail. I’m going to make sure I have it all and get back to it next time. There’s a lot of story to tell here and I know that everyone is going to love it. We’ll pick back up next time!

I just remembered a story and I feel like I have to share it. It was a long time ago and I had completely forgotten about it until a few minutes ago. It’s the memory of my very first hook up when I was in high school. I don’t really dwell on the past all that much because I’m more of a “live for the future” kind of guy. Still, it popped into my head and I figure that it’s a good time of year to tell a story or two. Maybe it will convince a few of you that hooking up is never something that you should shy away from.

I was working as a babysitter

Just to drive home how long ago this was, I was working as a babysitter at the time. It was easy money and it gave me a chance to get all of my homework done while eating someone else’s food. The kids were usually in bed by 8 or 9 and I had plenty of time to just chill out by myself. At least, that’s how it usually went. This particular job was at the house next door to mine. It was already pretty lucky that I didn’t have to travel far, but I had no idea just how lucky I’d be getting.

The mom stayed home

So, normally, my babysitting would be for couples who wanted a date night. It’s a pretty common thing. This job was going to be for a mother who was going to be staying home while I babysat her kids. No one in the neighborhood had any idea of this, but this woman was a practicing Wiccan and her husband was traveling for work. She needed me to watch the kids while she went off by herself into the basement to practice her religion or some shit. I’m not a religious person, but I had to assume that this was a real thing that people did.

I hear noises downstairs

Anyway, I watched her kids for a few hours, then it was time to put them to bed. I got them all tucked in and headed back to the living room to get my homework done. I was just walking past the basement door when I heard some weird sounds coming from down there. Curiosity got the best of me, so I opened the door and went down the stairs.

She was certainly some kind of Wiccan

I get to the basement and there I see it. This forty something year old woman was in the middle of pentagram panted on the floor with candles all around her. She was on her back, completely naked with her legs spread wide while she actively and energetically fucked herself with a giant dildo. Teenage me just couldn’t tear my eyes away. She was sweating and straining and making all kinds of noises. She must have sensed me in the basement with her because she turned her head, looked right at me and held out her hand.

“My sexual energy isn’t enough for the demon! I need to harness more to summon him!”

Yeah, that was exactly what she said. I remember it like it was yesterday. I also remember that, even at that age, I wasn’t stupid enough to pass up some willing pussy.

She Harnessed me, all right!

I took her hand, walked into the circle, and this woman pulled me down onto me back and mounted the shit out of me right then and there. It was the first time I had ever felt my dick slide into another person and it felt amazing! She just rode me and rode me while she muttered spells and incantations or some shit. All I know is that I had never felt better than that moment. I was young and I tried to hold back of as long as I possibly could, but I never had a chance. Just as she got to the crescendo of her spells, I shot my virile, young load deep into this middle aged woman’s married pussy. I’m sure that she came too, because she doubled over and just laid there, heaving on top of me. Then she whispered that my sexual energy is powerful and that she felt the demon pass through her and enter the mortal realm.

We kept in touch

I don’t know anything about demons, but she certainly felt my cum enter her mortal womb. We kept in touch for a long time after that. Any time her husband was away and she needed some sexual energy, she’d just catch my eye from my bedroom window and I’d practically run over there. Shit, there were even some times when her husband was sleeping right above up in the bedroom. I dropped many loads into this amazing woman and maybe she did actually conjure a demon. Shit, maybe he just possessed me all those years ago and turned me into the sex fiend that I am today! Either way, I’ve always understood that true meaning of magic is just to make yourself feel good whenever you can. That was sure as shit the happiest Halloween I had ever had and we had many more after that! Maybe I’ll look her up one of these days. I did her plenty as a MILF, I’m sure she’d be even crazier as a GILF!