The below story took place years ago when I was 21 and a senior in college. “Michael” (my boyfriend at the time) and I are now happily married despite the events below.


My boyfriend, Michael, and I began dating my first week of college when we met while he was my orientation leader. He was a year ahead of me in school and we had what was seemingly the perfect relationship. Things were incredible between us for the next two years until, abruptly, at the beginning of his senior year he broke things off with me.

I never fully understood (and still don’t) why he broke up with me, but we continued to hang out and hookup from time to time. I was focused on getting back together with him so did not explore much with other guys. I only hooked up with a few over the course of that year and it was pretty tame every time.

After Michael graduated, he moved to start a job in a city a few hours away from our college that happened to be near my hometown. That summer, we hung out and had sex a few times but he still wasn’t interested in getting back into a relationship with me despite my best efforts. When I went back for my senior year, I was finally ready to start dating new people and had opened myself up to the idea of being in a relationship again.

One of the first nights back, before classes had started, I went to a friend’s house for a pre-party before going to one of the local dive bars. At the house, I met a guy named Zac who I hadn’t run into during my three years on campus (it was a small school, so this wasn’t that typical). For some background, I am a 5’3″, 120 lbs brunette with C-cups and an athlete’s booty. Zac was 6’1″ with brown hair and an athletic runner’s build. Zac and I hit it off immediately and spent the evening laughing and talking before heading to the dive bar. When the flowing drinks and excitement over meeting someone new started to set in, he kissed me and I felt butterflies I had not felt in a long time. We ended up dancing and kissing at the bar before I invited him back to my apartment.

At the time, Michael was still the only person that I had slept with and while I was really excited about meeting Zac (and he was a great kisser), I still kept it fairly tame that first night with a lot of kissing and light touching. I was wearing a dress that I kept on but he had pulled the top down to expose my tits and pulled the bottom of the dress up to get access below. After an hour or two of the kissing and touching, he went back to his apartment.

The next night, I went back to the same friend’s house for another pregame and sure enough Zac and his friends were there again. We drank, laughed and talked just like the night before but this time when everyone else went to the bar I asked him if he just wanted to hang out at my apartment again instead. Once we got there, we continued our conversation before heading to hookup again on the sofa in my living room. I was still hesitant to push things further than I was comfortable with, so while things were a bit more hot and heavy, we still did not go further than that.

He went home again during the night and we made plans to go on a date the following weekend after the first week of classes. I was finally excited about someone other than Michael and it felt so incredible to have that passion ignited again.

Then, everything changed that week when Michael came back to campus for a recruiting event for his company. We got dinner and hung out and he told me he finally realized what a mistake it had been to break up with me a year earlier and that he wanted me back. It was quite a whirlwind since I had just started developing feelings for Zac, but I still felt Michael was “The One” deep in my core. We talked for hours about what sort of changes we both needed relative to our previous relationship together and ended the night officially as a couple (topped off with some wild sex that taught us that my new bed frame at my apartment was outrageously squeaky).

Fast forward to the spring, and everything was going really well with Michael. We would alternate weekends visiting each other and our weekends were always full of sex (so much so that I was always sore enough by the end of the weekend that it was almost a relief to be separating for a few days). A big group of seniors at my college had planned a spring break trip to an all-inclusive resort in Cancun. I tried to get Michael to come but he couldn’t get off of work for a full week and said he felt a bit weird going on a college spring break trip when he wasn’t in college anymore.

So me, my friends, and about 30 other students from the senior class headed down to Cancun for the week. When I went out to the pool the first day, I was surprised to see Zac and his group of friends there. We had run into each other a few times since the fall at parties or bars and had nice conversations, but I knew he was hurt by me basically ghosting him after Michael and I got back together.

That first day of the trip by the pool, he came over and sat in an empty pool chair next to me. While I had felt his chest and abs while we were hooking up, he hadn’t actually taken his shirt off so I was surprised by just how gorgeous his body was. We each had a cocktail and talked for a while about our plans for after college and I awkwardly filled him in on how well things were going with Michael. After a bit, he went back over to his friends and I went for a swim in the pool with mine. I didn’t see him the rest of the day but his abs stayed on my mind. I felt a bit guilty, but nothing wrong with a little eye candy.

The next day, I ran into Zac again while we were in the pool. It was the middle of the afternoon and we had both had a lot to drink at that point. He opened up more with me about how much he liked me and how sad he was when I ghosted him. I told him I had been really interested too but the future I saw with Michael was too much to pass up, even with how passionate my first few nights hanging out with and kissing Zac had been.

As I was telling him how much I had enjoyed those nights, he leaned in and kissed me. I immediately felt the burning desire from those first few nights again, coupled with a feeling of “oh shit, we are in the middle of the pool and everyone here knows I have a boyfriend.” After a few seconds when I realized what I was doing, I pushed him away and made a bit of a scene just in case anyone had witnessed the kiss. After I told him off loud enough for anyone nearby to hear, I leaned a bit closer and whispered, “meet me in room 314 in 10 minutes”. He left the pool and I had to stop and ask myself what the hell I was doing.

I was overcome with a number of emotions from excitement to fear to guilt, but desire was at the top of the list. I told myself we would just hang out and talk a bit more in my room and if we kissed a bit more, was it really that big of a deal since we had done it already?

By the time I got back to my room, he was already waiting outside. I opened the door with my keycard, and as soon as the door closed behind us he pushed me against the wall and kissed me deeply. I was just wearing a white bikini and he was wearing blue swim trunks. After a few seconds of kissing, he pulled away and asked me if this was okay since I had a boyfriend. I told him that he and I had already spent hours kissing at my apartment in the fall, so this really wasn’t doing anything different before I pushed him against the other wall and kissed his lips, his neck, his chest and his stomach.

Our hands were running all over each other and our make out was sloppy and aggressive. We fell on the bed and he started rubbing my boobs over my bikini top before again stopping to ask if it was okay. Once again I told him he had already touched them so it really wasn’t doing anything new. He pulled off my top and softly kissed all around my nipples while I ran my hands through his hair. His soft lips felt amazing and he shocked me when he lightly bit one of my nipples and pulled on it with his teeth. For all of the sex Michael and I had over the course of our relationship, he had never bitten me like that and I had no idea that I would fucking love it.

I let a moan escape, grabbed his hair and pulled his lips back up to mine. While our lips were locked and our bodies were intertwined, he ran his hands all over me. He started squeezing and slapping my ass over my bikini — again, had no idea that a hard slap would send those kind of chills through me — before asking if what he was doing was okay. One more time I told him that he had already felt my ass so this really wasn’t doing anything new. He pulled off my bottoms and started to lightly run his fingers around the edges of my pussy lips while our kissing intensified. I reached down to slide a hand under his suit to find out he was already fully hard.

I was lost in the moment but it still hit me that this was the first cock I was touching other than Michael’s. A slight twinge of guilt crept back into my mind but I was enjoying myself too much to care. I sat up and pulled off his trunks to expose his throbbing cock. I was shocked that it looked to be almost exactly the same size as Michael’s but maybe a bit longer and with a bit more girth. Michael always liked to tell me he was bigger than average, so while I had no one else to compare his and Zac’s too I knew that Zac’s was the perfect size for me.

I rubbed Zac’s hard on with my hands while we kissed and layed on the bed and he circled a finger around my clit. He knew just how to perfectly tease my clit with his fingers to get me even more excited. Without MIchael on the trip, I was of course not planning on having sex and did not bring any condoms with me. Since we were in my room, I told him to wait a second and I walked over to my roommate’s suitcase. Her boyfriend was on the trip as well and sure enough, there was an open box of condoms in her suitcase.

I went back to Zac and told him to lay in the middle of the bed. I unwrapped the condom and slid it over his 7″ cock before straddling my legs over him. I leaned down and kissed him one more time before lowering myself onto him. “Holy shit” I said out loud. This was only the second person I had slept with, and I could not believe how that extra girth and the overwhelming insanity of the situation made my pussy throb. I normally don’t love being on top for too long but I could have ridden Zac all day. I started slowly but did not take long before picking up the pace. I must have only slid up and down on him for a minute or two before I had a body shaking orgasm. “Holy shit” I said again.

Zac smiled and told me how hot it was and how he had been wanting to make me cum since the first time we met. I told him if I knew he could make me cum like that, I wouldn’t have held out on him those first two nights and also told him it was time to make it happen again. He effortlessly pulled me off of him and told me to lay on the edge of the bed. He got up and stood on the side of the bed and pulled my legs over to him. He grabbed a pillow with one hand while lifting up my ass with the other and sliding the pillow underneath.

Now, this caught me a bit off guard. Michael knows that this position is easily the one that makes me cum the fastest. How the hell did Zac know? I thought Michael was some sex guru for figuring this out but Zac seemed to know exactly what buttons to push. He spread my legs with his arms and started to slide into me slowly. He quickly picked up the speed and strength and was pounding me deeper than I had ever been fucked before. I was moaning so loudly that I’m sure everyone in surrounding rooms could hear but it felt so good I could not have cared less. Once again, I felt myself about to cum and couldn’t hold back. My body shook again with each pulse of my muscles.

“Holy shit”, I said again. We had probably been having sex for 5 minutes and I had already cum twice. “I’ve never cum twice that fast before”

Zac smiled. “Think we can make it 3 in a row?”

I nodded and he asked me what position I wanted it in. Without saying anything, I rolled over onto my stomach, lifted my ass a bit in the air and spread my legs. He knelt behind me and I quickly felt him plunge down deeply into me. Finally, for round 3, I thought I was going to outlast him. He continued to absolutely hammer my pussy while my ass slapped back against him. He reached under and grabbed my tits and would lean down to kiss my back. He told me he was getting close and asked if I wanted him to pull out. I told him to finish inside with the condom (I was on birth control but I still never let Michael finish inside…I’m not sure what got into me) but to keep going because I was going to cum again too. Another few seconds and sure enough we were having an incredible simultaneous orgasm.

He collapsed next to me on the bed, we looked at each other and we broke out laughing. “That was the best sex I’ve ever had” I told him. And I meant it.

We laid on my bed naked and talked for a few more minutes before I asked if he would mind leaving before my roommate got back and so I could get my life in order.

I had a lot to figure out with Michael and Zac…and this was only day 2 of a 7 day trip. Was the best of the trip still to come?