My sister is 2 years older than me and we went to the same college. My freshman year she went to her bf’s college (out of town) for halloween and her roommate, let’s call her Kelly, invited me to come to the party she was going to. Of course, as a freshman without a fake ID, I said sure as I had met Kelly plenty before since she lived with my sister for 2 years.
Kelly was not hard to look at. She was short, maybe 5’1, long straight black hair, full C cup and worked out regularly. I dressed up as a pirate in my dorm and walked to her place to start drinking before the party. When I arrived I saw her in a fairy/princess costume with a tiara, tight pink crop top, a short white skirt and pink fishnet leggings leading to her white high heels, she looked great. My sisters friends were there, maybe 15 of them drinking and when the time came we all headed down to the party.
I felt kind of weird as I was the only one under 21 there but everyone kinda loved it saying things like, “lame your sister didn’t show up,” and “It’s about time you came out with us!” which made me feel better. Kelly low key LOVED parading me around as her “roommates hot younger brother” and when she would say that I thought she was joking… turned out she wasn’t.
Around 1am everyone was sufficiently drunk and Kelly made eye contact with me from across the room and motioned for me to follow her and of course I did. She led me to a bathroom kind of far away in the house form where everyone was and pulled me in there. Inside, she sat on the sink counter and wrapped her legs around me pulling me close and kissed me saying, “I’ve always thought you were hot, you can’t tell your sister anything.” We made out for a minute or two before we snuck out of the bathroom and left the party.
She took me back to her apartment and brought me to her bedroom where she laid on her back on the bed and I straddled over her feeling her up and making out, peeling off our clothes as we drunkenly ravaged one another. She leaned over to her bedside table drawer and pulled out handcuffs, looked at me and said, “have your way with me daddy.”
I was in shock, here I was, 19 and my sisters roommate is asking me to handcuff and fuck her brains out. I flipped her on her back, handcuffed her hands behind her back and slowly started thrusting into her. She started moaning loudly and her back arched in pleasure as she took my shaft inside her. We fucked for 30-45 minutes (who knows we were wasted) until she was on top of me, still handcuffed bouncing on my cock. She started screaming, “cum inside me please, I need it!” and I lost it and exploded deep inside her.
We laid there for a while after, making out and all before falling asleep. The next day I did the walk of fame (not shame) back to my dorm. I would see her often after that but we never fucked again… sadly. My sister never found out and Kelly is now married with 2 kids.
Source: reddit.com/r/gonewildstories/comments/aqdtjg/fucking_my_sisters_college_roommate_on_halloween
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Hate to ask.. but neither of them are yours right?
great story lucky guy
You gotta tell your sister now to see her reaction, I mean no harm now since it’s been years right?
Great story, great job
Really hot story! Love that she had you marked as a target when she knew about her roommate’s brother haha