Cucking my bf in 1 Background.

My name is Jill and this story took place back in the early 2000s. I grew up in a suburb of New York and my junior year of high college I met Rob. He was a sophomore and was so cute I left my current boyfriend for him. I had had sex with my previous boyfriend a few times but when I started dating rob I took his virginity and we became inseparable throughout the rest of high college. It was a normal puppy love high college relationship complete with a promise ring. You know the type. We had a good sex life if not all that adventurous that included oral sex. I was on the pill so he mostly came inside me or on my tits and on the few occasions that he did cum in my mouth I at all times spit it out. Rob was around six feet tall with brown hair hazel eyes and very handsome. He played hockey, was in great shape, and his cock was about six inches and decently thick which at the time I wondered of as big (my first boyfriend was only around five inches and kinda thin). My drivers license says I’m 5”2’ but I’m really a little short of that with brown hair and eyes and at the time I stayed in good shape playing volleyball and soccer. I was blessed (or cursed) with very large breasts for my size and at the time I wore a 34DD bra which I was at all times a little self conscious about until I realized how much rob loved them. I would describe myself as more of the cute girl next door type than as some sexpot.

This story really begins at a party the summer before I was to leave for school. Rob’s parents were away for the weekend leaving him the house to himself so he threw a small party. There were about twenty or so of our friends there as well as Rob’s cousin Brendan who was also staying at his house for a summer internship. Brendan was a year or two older than me and I’d met him a few times over the course of my relationship with Rob. Anyway, as the party was winding down I ran into Brendan as I was coming out of the second floor bathroom and he ended up kissing me. It was unexpected and I don’t remember how it even happened except that we were both drunk. We ended up making out for a few minutes and he worked his hand up under my shirt and bra before I pulled away and went back downstairs to the party. The interaction left me extremely turned on and I dragged Rob to his room as soon as I could to fuck him. Somehow as we were going at it I confessed to what had happened and instead of getting mad he fucked me harder and came in me. When we were finished he started grilling me about exactly what happened and as I told him his cousin felt my bare tits he was already getting hard and we fucked again. As we were going at it he said I should have just fucked Brendan and in the heat of the moment I agreed. Then he said I should just go down to his room right now and fuck him and again I agreed but I didn’t think he was serious until he got off me and looked down at me expectantly. We had a brief conversation about how serious he was and the next thing I know I’m walking the two doors down the hallway completely naked.

By this point it was probably two or three in the morning and everyone had either left or passed out in the finished basement except for Brendan who was staying in the guest room on the second floor. Most of the details of that night are hazy but I distinctly remember standing outside Brendan’s door and looking back down the dark hallway where I could just make out rob standing in the hallway watching me as I opened the door and went inside. When I walked in the room was very dark but I could just make out Brendan was sleeping. At first I just stood there deciding if I could really go through with it then with all the courage I could muster I walked next to the bed and gently shook him awake. He was obviously confused at first but I think I said something about finishing what we started and next thing I know I have his soft cock in my mouth. I think he was a little apprehensive about what was happening at first because it took me a while to get him fully hard but once he was I climbed on and started riding him. By that point he was definitely into it, grabbing and sucking on my tits as I slowly rode him. His cock was slightly larger than Robs and felt really good. After a while he flipped me on my back and got between my legs and fucked me hard until he finished inside me. After he finished we lay there catching our breath for a minute before I got up saying something about this being our secret before I got up and went back to Robs room.

(This is a little longer than expected so I’ll continue in pt. 2)

NSFW: yes

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