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Cumming in the Wrong Hole [MF] (More Comical) | 2016
Just wanted to mix it up a bit. This one isn't a sexy conquest, but just a light hearted hookup story.
A group of about 20 of my fraternity brothers did Spring Break together and spent the week in Florida. The week initially was awesome and we had ton of conquests... our motel rooms serving as base camp. To save money every room slept 3 deep. When guys had girls over they would get the bed to themselves and if two guys had girls the odd man out would crash in the floor.I shared a room with my two closest Fraternity Brothers Shaun and Derick.
Derick was well connected with the DZ's at my school. On Wednesday he mentioned a DZ named Caity and her sorority sister were wanting to come up and party with us on our last night that Saturday. Caity's family owned a condo about an hour south and they were staying there for their Spring Break but it was far from the scene we were at. The plan was to party with us, spend the night, then follow our big group back to our school.
On Friday night things became interesting when the guys in the room next to us got a little too wild and a chair found it's way through the window. Since they were kicked out of the hotel we agreed to let them sneak into our room and sleep on the floor that final night.
As Saturday rolled around everyone was hung over, broke, and frankly tired of being in the big group... essentially ready to keep it low key and go home. Caity arrived at around 2:00 that afternoon and Derick met them at the room. The two girls changed into their bathing suits and came onto the beach. Caity's sorority sister was Chasity. Caity wasn't my type and I knew her previously as well but had never met Chasity. She was a short and cute brunette, cute body with average breasts and ass, and very quite. She spent the day on the beach to herself and I made conversation with her to make her feel welcome.
That evening there really was no large group anymore. Everyone had formed into their cliques. Some guys had one last night at the bars.. my group decided to keep it low key and have dinner together and drink lightly in the room. Caity and Chasity drank harder than everyone else making up for lost time that week. As Chasity caught a buzz she put down her defenses, and as the only guy who really made an effort during the day, I found myself as the person she had latched onto. I began flirting with her and initiating contact. Before too long we were laying on the bed as everyone else drank wrestling over a pair of cheap sunglasses of mine she wanted to take.
As the night wound down we snuck off on the beach for a walk as did Caity and Derick. They walked about 30 yards ahead of us.Eventually they found a cabana and disappeared and so did Chasity and I. After kissing and heavy petting Chasity told me she "wasn't the type to hookup with a guy she just met" and we needed to hang out once we got back. I took this as a cue and was tried so we headed back. We yelled for Caity and Derick and they followed.
Our room was a Halfway House of drunks sleeping in all areas. Fortunately guy code withstood and one Queen Bed was empty. The Four of us tip toed in and squeezed in. From L-R.. me, Chasity,Caity, Derick. I fell asleep quickly and was awoken to Chasity whispering my name asking if I was awake. I am not sure how long I had slept but everyone was asleep and she rolled to face me and we began kissing again.
We stayed as still and quite as possible and still fully clothed I maneuvered my hand under her shirt and unhooked her bra. She gripped my cock in my shorts and I rubbed her crotch. Whatever stirred her thoughts made her horny as she had lay there awake but we couldn't do much. I then whispered "Bathroom... Quietly" and she tip toed through the dark and I followed.
The bathroom was a train wreck. People's dirty towels and clothes were everywhere. "Let me get a condom out of my suitcase" I whispered but she stopped me. She said she wouldn't have sex and also didn't want to get caught.. anything else.. but quick.
We stripped down and started in the floor where I was going to go down.. the floor was wet... I reached for a towel and they were all soaked. "Sit on the toilet" I said... "That's too gross!" She responded.She sat on the edge of the tub and I started on her but she was uncomfortable and her arms too short to hit the other side and support her.
"I'll do you tonight" she said.. "Pay me back at home. You sit here."
I then sat on the cold wet edge of the tub as she got on her knees on the tile before me.
"DO NOT CUM IN MY MOUTH!" she said half laughing while staring a hole through me. "I WILL PUKE"
For as awkward as everything had been Chasity was amazing with her mouth. For all my conquests the list is short for girls who got me off with a BJ, and Chasity may have been the best. Her technique was perfect and intense. I may have lasted four minutes before it was time. I gave the courtesy tap. She kept on. I tapped again and said "Chasity I'm ready". She kept on.
My cock was burning ready to erupt. "Chasity stop". Kept on. I couldn't hold it any longer. I put my hand on her forehead and forcefully pushed her off right as my load released with force barely removed from her lips.
"You asshole! Get me a towel. The hell."
The angle of my push and the trajectory of my load resulted in a perfect money shot to her right nostril. She sat with her arms at chest height not knowing what to do with them. Her mouth shut as the cum slid toward her lips. Her eyes closed.
She mumbled, "Towel. Towel." and began gagging from the burning of her nostril and the smell. The towels were a disaster..all soaked. I felt for the least soaked and promptly cleaned her. She blew her nose into it and pushed me.
"Seriously!"
"You told me not to cum in your mouth and I tapped you!" Our voices not whispers.
She finally realized I had no choice and it was a lucky shot and finally laughed. "You owe me! Do not tell a soul! I will kill you." We put our clothes back on and turned the bathroom light off and crept back to bed one at a time.
We were about 45 minutes departed the next morning when Shaun spoke up from the back seat. "So... I saw something I have questions about..." I was driving and looked into the rear view to see his shit eating grin. "What's that?", I inquired though I already knew.
"Well I heard a commotion and sat up.. there was a light coming from the bathroom and the door was cracked just enough for me to see the reflection in the mirror above the sink." If anyone remembers old hotel rooms the sink/vanity was separate from the toilet and shower. We had not shut the door all the way for fear of waking someone up.
Shaun could not see everything but he said he could see half of her naked body (A hip, a tit, and a head.. he said)and see her panicking and then me wiping her with a towel. I swore them to secrecy and re-told the story. Of course when we stopped for lunch they couldn't resist making jokes about blowing their nose and she knew they had found out. She actually played it pretty cool once she found out Shaun had seen the ordeal.To my surprise she began texting me that week and I had to "re-pay" the favor and be her date to their preference dance and go down on her that night. We became fuck buddies and pretty good friends. I actually posted a story some months back about a night at her apartment.
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