I have submitted this edit, to attempt to match the actual occurrence in the most accurate manner, changing the names of those involved of course. Thank you for reading, and please vote. Thanks!
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Not unlike most 18 year olds, now that High School was finally behind me, I couldn't wait to get to college. I spent quite a bit of that summer with one of my best female friends, Shell. We have sat next to each other in school for nearly our whole lives because our last names were similar. Having spent so much time near each other in school, we have become great friends. She wasn't considered to be one of the hottest girls in school, but she was the next door type. She didn't have the biggest tits or show tons of cleavage, but I definitely found her attractive. She was a slender 5'8" brunette with an athletic build. She had toned muscles but was no means overly muscled or anything, with a flat stomach, 34b cup, and a killer ass. My problem, she had a boyfriend who was one of my friends. Ryan wasn't really one of my close friends, but we became friends in spite of each other for Shell's sake. And Ryan seemed to be the center of Shell's world. It was almost that he could do no wrong, even though he was a little bit of a jerk.
I had a girlfriend too right up to graduation, but with getting ready to leave for college and all she broke it off a week into the summer. I've had a few girlfriends over the last few years, but never had serious relationship. But the furthest I've gone with any of them is some handsies stuff.
We spent alot of summer afternoons in her pool escaping the heat. One day I stopped over to swim, but found she was the only one in the pool. I forgot that some of our friends picked up different shifts at work and weren't coming over until later. But I found it odd that Ryan wasn't there. As I climbed the ladder to the pool deck, I noticed she was just leaning against the edge of the pool. "Hi Shell, where is Ryan; isn't he coming?" I said. What I didn't notice at first was that she was trying to compose herself to make it look like she wasn't crying.
Trying to keep any sniffling at bay she said, "We broke up last night, I thought everything was going so great. He told me he loved me, and then we..." and then she paused. Tears welling up in her eyes again she tried to pick up where she left off saying, "then he broke up with me. I hate guys, they're such assholes."
At first I was really pissed because I know the words she didn't say during the pause. She was a virgin before last night, and her dickhead boyfriend who I called my friend just for Shell's sake, told her he loved her just to sleep with her then dumped her five minutes later. I thought I'd want to comfort her, help her, but then an emotion overtook me that I didn't really expect. I was jealous. Very jealous. I couldn't believe I felt that way. This was my best friend crying over a jerk fucking her over, and all I want to do is sleep with her too. And more so in this minute than any time before. Was it because she said yes to someone else, and wasn't a virgin anymore? Was it that I have wanted her the whole time... I really wasn't sure. She looked so hot in her swimsuit. Shell wasn't wearing a bikini today, but it was so tight around her firm tits, and the bottom part followed her pelvic bone up over her hip bone around the back to her perfect ass showing off tons of leg. I couldn't help but check her out. But my rational side overtook me, and I consoled her. It kinda sucks being the nice guy, but that's what my friend needed.
We hung out off and on over the next few weeks, and Shell seemed to be getting over their break up. I came over one day to find her mom packing the car. There's only one perfect word to describe Shell's mom, MILF. All too often did I need to hide an erection visiting Shell, whether from checking out her mom. For a forty-something mother of two, she was smoking hot with dirty blonde hair, maybe 5'9" or 5'10", with nice curves, and there were definitely a nice pair of breasts hiding behind her always too baggy clothes. Shell's dad was a lucky man to be with her. She asked if we were going swimming, and I said yes. She said that she'd come around to the deck in a few minutes to talk to us. Apparently, Shell's parents were going on a trip for a few days and leaving her at home alone. A few minutes later her mom came up to the pool deck saying, "now I'm leaving the number to the hotel on the table. No parties. No drinking, you're are 18 and responsible enough to stay here alone, but not old enough to be drinking. I'm not stupid, I'm sure you will have a few people over, but that is it. A few. And no Ryan, he's caused you enough heartache. If he comes by, shut the door in his face for me." After a few goodbyes they were gone for a few days to be back on Sunday.
Alone in the pool with Shell, we swam around, splashed each other, just messing around. At one point she swam bye, and out of nowhere, I grabbed both straps of her one piece off her shoulders pulling them down her arms as her suit exposed her down to the waist. She let out a yelp and started squirming around trying to get away. Her smooth legs brushed against mine, as she tried to kick out of my grasp. Finally, I had to let go as she twisted her way free, but could see her fully tanned back and the top of her ass hanging out of the suit. She was turned away from me when her head came out of the water looking over her shoulder with a scowl on her face. She had one arm wrapped around her body to cover herself up and the other pulling her suit up. She was pissed, and all I got was the slightest glimpse of side-boob. I told her that I was sorry and just screwing around, but that little peak at normally unexposed flesh left me wanting for more. Par for the course for me, I didn't have the balls to try something else.
I came over after work the next day to find some of our friends Kim, Erin and Steve getting out of the pool and could hear Shell inside the house. As I walked into the kitchen, she said "Make yourself at home, I just need to grab a quick shower to wash the chlorine out of my hair before we go to the movies."
Without a second passing, I asked, "need any help...to do it right and all."
"Not a chance" was all the response I got along with a look of don't even try to go there. But before she closed the bathroom door, she gave me a smirk that got me intrigued. Then, I could hear the knob lock with a loud click. I had no idea how to take that. The locking of the door was an obvious no. But that smirk made me think with a little time I have actual chance to work my way out of the friend zone with her.
The next few days went on like that with some playful flirting on both sides. Any opportunity I got, I made some sort of sexual comment. They didn't seem to get me anywhere, but it was fun. I even told her a few of those overly cheesy pick up lines, they made her laugh which was good to see. But she didn't seem to look at me as anymore than just a friend. On Saturday she was laying on the pool deck when she asked me to put on some more sun tan lotion. "I take any chance I can get to lube you up," I said. I was glad she laughed, but then she put her head down and held up the lotion. She looked great laying there, wearing a two piece string bikini top and hipkini style bottoms. So I decided to be a little braver than usual. Instead of sitting to the side and applying lotion to her back, I straddled her perfectly shaped ass. She didn't object so I bent forward and untied her top allowing the strings to fall to her sides. I loved the feeling her skin under my hands. I felt a twitch in my cock, but it wasn't much more than a semi so I thought that maybe she couldn't feel it. After a little bit I was afraid that she was going to say that was enough lotion. So I took a chance and pushed my hands up along her sides. Starting at her hips working my way up to her ribs and back a few times and then I leaned in pushing my hands further up along the sides of her breasts. It was then I noticed that my fully hard cock was pressed into the crack of her ass. Embarrassed with all of my newly found confidence fled, I briefly grabbed her hips and told her that she should be all set for now. I stood up, stepped over her, and dove into the pool. The rest of the day went by without incident. I wasn't sure if Shell's lack of comment was a good thing or a bad one. There was no way she didn't feel me against her. Did she want to pretend it didn't happen or what?
Then Sunday came. One of summer's few rainy days, but of course that meant no swimming nor ogling Shell in her swimsuit. It ended up being just us again which was fine with me even if we were just gonna hang out. After an hour or so of cards and idle chat, I figured I should probably get going even though it was only early afternoon.
"How about another game?" She said. "Something else, anything you want."
