You are here

The night I [M]et my roommate's best [F]riend | 2016

I'd been living with a new roommate for about 6 months. She was always telling me about how I'd get along with her best friend, Tessa. I resisted, thinking a set-up would never work, but she persisted with the comments - she'd tell me how boys always chose Tessa over her, and how hot she thought Tessa was - blonde hair, blue eyes, tight body and a perfectly round ass.

Fast forward a month and she was planning a cottage weekend. I wasn't going to miss a chance to get out of the city, so I told her I was down. It wasn't until the day of that she mentioned Tessa was coming for the weekend and was excited to meet me. Seems the girls had ulterior motives and had been planning this as a set up the whole time. I felt a little uncomfortable, in case the set up was a disaster, but decided the cottage weekend was worth the gamble.

I drove up by myself after work on Friday and Tessa hadn't arrived. She was delayed in the city and would be a couple more hours, so I got a beer and relaxed with the others. I was at home with a good group of people, despite being the outsider in a group of long time friends. I learned that one of the guys in the group, Dave, really liked Tessa. They'd dated briefly in high school, and he mentioned her more than a couple of times in conversation before her arrival.

I was a couple of drinks in when Tessa finally arrived. She sought me out immediately to introduce herself and I was actually taken aback by how attracted to her I was. Her bright eyes and perfect ass really stood out. She was wearing a bikini with tiny jean shorts and a white tank top overtop. We shook hands a little awkwardly and started talking and flirting.

It seemed like it was Tessa and I alone for the rest of the night, but in reality, the whole group was still there and very much part of the night. Tessa made every effort to find herself near me and I did the same. We didn't talk about it, but there was something going on between us. Around midnight, I announced that I was headed down to the dock to take a swim. We'd all been drinking for a few hours and there weren't many takers. Except Tessa, she threw her hand up in the air and volunteered to join me. Perfect. I was going to get some alone time with a girl who was clearly as into me as I was to her. And then Dave decided he was coming too. Fucking Dave, I thought.

We get to the dock and I rip off my shirt and do a gainer into the lake. Before I surface, I hear a splash and it's Tessa joining me. I have no clue how she got down to her bikini that fast. We're in the water, getting used to the temperature, and fuckin' Dave is pissing and moaning about how it's too cold to jump in. We mostly ignore him and are talking to each other closer and closer until Dave finally jumps in and we separate a little.

It's clear at this point. Tessa and I want each other, Dave is into Tessa, and he's putting up the best fight he can to convince her to pay him a little attention. With him in the water, Tessa doesn't change at all. She is always facing me, always talking to me, and is getting closer and closer. We're staring into each others eyes. Goddam she looks great in her bikini. After a few minutes we're so close we're basically in each others' arms. But we're treading water and needed space so we didn't kick each other under the water.

At this point Dave gives up and heads back to the cottage, defeated. It's just her and I. Tessa says to me 'Dave and I fooled around in high school and he still likes me, but his dick is really tiny. I just can't'. Jackpot! We start kissing right away; shes such a great kisser I can't get enough. Her tongue is so soft as it feels mine out. We move close to the dock so I can hold on and we can get closer. She immediately wraps her perfect tanned legs around me and attacks my mouth. My hands couldn't have reached for her ass fast enough. It was easily her best feature - Tessa's ass made every other girl jealous. It was naturally perfect. We made out for a couple of minutes and moved on to the dock to continue.

I was in heaven - this super hot girl I just met was all over me. She clearly noticed how hard I got and her hands kept reaching into my boardies to jerk me off. We were only half in our swimsuits while on the dock - we really tried our best to strip each other without breaking our kiss. After only about five minutes of making out on the dock, all of a sudden my roommate yelled from the cottage that everyone was going to bed. We scrambled to cover up and Tessa jumped up to head to the cottage. Buzzkill. I found my way to my room, and she did the same. I fell asleep frustrated, thinking I missed out.

In the morning I opened my eyes to Tessa - still in her bikini - opening the door to my room, walking around my bed, and climbing in. Interesting. She moves in very close to me, says "Good morning", and starts kissing me again. She did not like getting interrupted last night. She took my shorts off right away and helped me get her naked. In the morning sunlight I swore this was the hottest girl I'd ever seen.

I rolled her on top of me and she kept sliding her already very wet pussy along the shaft of my cock and moaning so loud I thought she'd wake everyone up. How was she so wet already?! I made her sit up so I could stare at her perfect tits. When I put her nipple in my mouth she would grind on my cock harder. I knew she loved it. Tessa reached down and pushed my hard cock into her pussy with a sexy moan. It took a few moments before she could take it all inside her. I filled her right up with my cock, and she clearly loved the feeling.

Because I'm a little sadistic, I told her to get up off her knees and put her feet on the bed. I love looking into a girl's eyes as she realizes how much deeper my cock is in that position. Tessa was no different. She sat down and my cock bottomed out in her before I was all the way in. 'Feel how wet I am' she said as she reached down to touch her pussy. I reached around her legs to feel from behind. She tensed up and moaned as I grazed her asshole, so I started rubbing the entrance to her ass.

Tessa was bouncing on my cock as fast as she could. I was hitting the back of her pussy everytime, and that's about the best feeling in the world. She was alternating between rubbing her clit and grabbing my cock to feel how wet she was making it. It felt like I was being jerked off as she was fucking me. I had my middle finger inside her asshole as he bounced. I wanted this girl to feel how full I could make her. It was only a minute into our rhythm that she started shaking and came all over me as she collapsed on top of me. She quietly brought her fingers to her mouth to taste herself. I took it as a sign, so I grabbed her hair and turned her head the side, feeding her my fingers - including one that was deep inside her asshole - for her to taste. She greedily sucked them clean as I thought to myself what a good girl I'd found.

I gave her a minute to recuperate before guiding her down to suck her cum off my cock. She positioned herself between my legs and dove right in with her back arched and her perfect ass high in the air. At that moment I knew this is exactly how I wanted to cum. I told her what I liked - mouth and hand at the same time - and she knew exactly how to suck my cock, twisting her hand as she got to the head. Twice I stopped her to bring her up and lower herself onto my cock, just so I could watch her taste her pussy on me again.

After a few minutes of expert cocksucking, it was time. I grabbed Tessa's hair with my hand, pulling her off me while I jerked off and painted her face with my cum. I came so much as she eagerly licked my cum off her face. When I was done she cleaned my cock off one last time and then used her fingers to collect the rest of my cum into her mouth and swallowed every last drop as she stared into my eyes.

Tessa and I dated for awhile after that and I have many more stories I could tell.