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My First Time Staying The Night

1086 words | 0 |4.88

My First Hookup Sleepover With An Older Man

It was a friday afternoon, I had just finished school for the week and was feeling extra horny. I was staying late at the school to finish cleaning out a room with my teacher for community hours needed to graduate.

My job was to organize all the donated cloths by size, and gender. I had been organizing for about 3 hours after school ended and was only half way finished.

The teacher that was with me left a few times to finish some work that needed to be finished for the next class on monday.

Because of this, I had to do most of the work alone. Now, as a horny teenager organizing clothes, alone, with no supervision, I ended up taking some for myself.

While that was the purpose of the room, to give clothes to any students who are lacking at home; I ended up taking a bunch of girls clothes for myself.

I stuffed leggings, and jeans into my backpack, along with any shirts I thought were cute or revealing. I took a few dresses and shoes that fit, and took some socks that looked nice or stockings that made me feel sexy.

By the time I finished packing all those clothes and went to the underwear box, My backpack was stuffed to the max. So what did horny me do? I got undressed and picked through the panties and bras I wanted and put them on myself.

Now for a donation to a school, I think there were a few too many thongs and g-strings in that box, which I didn’t complain about.

When all was said and done, it was time to leave. Me and my teacher where one of the last people out of the school for the week. I didn’t have a way home and didn’t want to walk 3 hours, so I stayed back and connected to the school Wi-Fi.

Instead of texting one of my parents to come pick me up, I opened grindr and began looking for a fun way home. I found someone that lived close by to my mother’s and was what I was looking for, an older guy that likes to top. He was in his late 50s and answered my messages happily.

Well chatting with him made me even more horny and I began to think irrationally and instead of just getting a ride to his place to have fun an leave afterwards. I agreed to stay the night.

I messaged my mom and told her I was staying over at my friends place for the night and that I would be back home around dinner time the next day.

I waited at the school entrance until I saw the small red van pull up, to which I got into the front seat. I was pretty nervous and shy as he introduced himself and started asking me things about myself and told me about himself, all while rubbing my leg.

I told him that I don’t have much experience and that I’ve only done the same things with the same people so being with someone much older was new to me.

He told me not to worry and that he’s a gentle and respectful guy. we arrived at his place, it was a nice house, one of those places where one person lives upstairs and someone else lives down stairs, yea he lived downstairs and his landlord lived upstairs.

We got inside and I looked around a bit before I sat down on his couch and waited for him to finish whatever he was doing in his room. He came out undressed and in overly sized boxers. He sat on the other side of the couch and asked “you should undress too”

I began taking everything off except a black thong and matching bra and put everything else with my backpack. He seamed to like this and ordered me over to sit on his lap. I did and he began exploring my body, touching my dick and cupping my ass, rubbing my legs and kissing my face and neck.

I slipped my hand under his boxers and started slowly playing with his cock as he continued exploring every inch of my body.

I became closer and closer to cumming as he started stroking faster and faster when I came all over my legs and stomach. He didn’t stop however, he started rubbing the cum through his fingers and all over my dick, while kissing me.

After a while of that, he asked if I enjoyed bondage, to which I replied “never tried”. He asked if I’d be willing to try and i said I’m willing to try anything once. He said good and we both got up.

He led me to his bedroom, he handed me some things and asked me to put them on, they we’re thigh high stockings, and a blindfold. I put them on and he directed me onto the bed.

I laid on my back and he cuffed my wrists and ankles. He climbed up on top if me and began kissing me and slowly took off my blindfold. I started kissing back when I noticed a few cameras around the room. I was ok with this and began kissing more.

We kissed for almost 5 minutes before he rotated his body into a 69 position and started sucking on my dick while lowering himself into me, it was weird trying to suck someone’s dick like that until he started slowly rocking himself up and down.

He started picking up speed while sucking and thrusting when I came in his mouth, he swallowed and came into my mouth right after.

I swallowed everything as he got off of me and left the room. He came back about 5 minutes later and began rubbing my face down to my chest and down to the thong and between my legs.

Even though I was practically empty at that point, I got hard again when he started massaging my ass. He then put some kind of lube on my ass and began fingering me.

I lifted my legs as much as i could before the cuffes stopped me when he poked his dick into me. He began thrusting for about 10 minutes before cumming deep into my ass.

He sat there for a bit before un-cuffing me and walked me to the shower. We got cleaned up and went to bed, we cuddled all night until morning where i woke up to a grip on my ass.

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