Stealthy Sex [m/f] | 2016

Towards the end of senior year of high school, I began to have a steady girlfriend. Let's call her Gabriella. We lost our virginity to each other (quite a story there) and genuinely liked each other. Anyways, she was a grade below me. So, we both knew it would suck when I left for college. I had planned to come back home for a football game where my school was playing the school that my sister attends. I was going to stay in her apartment.

I had decided to come home early so I could spend some more time with Gabriella. Our relationship was kind of in a weird stage, we were technically broken up, but we still talked everyday. For a while it was just like normal, but eventually I noticed the communication become more distant, a constant small talk.

I decided I would surprise her at her house the night I got in. Let's just say the greeting hug wasn't what I expected. I missed her though, her smell, her blonde hair, that innocent cuteness. She was in a weird mood and things were awkward. However, we ended up on the couch together. One thing led to another and my hand made its way into her pants. It felt so good to finally touch her. We both had been deprived of sex for quite awhile and it was too much for her. She slipped down her pants just far enough and sat on my cock. She was extremely wet and warm. It felt too good. I told her I had a condom. After much fiddling in the dark, I eventually got it on. I flipped her over and we did it doggy style. I finished quickly. All of this happened in maybe five minutes. It honestly sucked. There was zero connection and no rhythm. It was just like we were using each other because we needed sex. I cleaned up, and we had some more awkward conversation. I was reaching for a connection that wasn't there, grasping for the past that seemed gone forever.

The next day was the day of the football game. After much difficulty due to phone service not being the best, I finally found Gabriella with only about an hour before kickoff. Still awkward. We chugged a beer and made our way to the stadium. The line to get in was ridiculous, so we were forced to talk to each other. The chemistry seemed to be behind a glass wall. I could see it but couldn't quite get to it. After seemingly forever, we got to our seats. The night air was nice, cool but not cold. The game started and for whatever reason, the conversations seemed to flow like old times. I guess football gave us something to talk about. She didn't know too much about what was going on, and I was thankful for the opportunity to talk about something that came easy to me.

Gabriella was planning to sleep with a friend in her dorm, because she thought sleeping in an apartment with me and my sister would be awkward. A controversial play happened in the game which was challenged. Gabriella disagreed with me about what the outcome would be. I bet her that if I was right, she had to sleep with me tonight. I was right. After the game, we were both too tired to go out, but we were starving. So, we called up my sister and went to go get food.

All the while, I'm thinking about how these sleeping arrangements are going to work. I didn't really tell my sister Gabriella would be staying with us, and my sister's bed is rather small. We get to the apartment and someone is already passed out on the couch, so that's not even an option. We go up to my sister's room and decide we will just squeeze into her double bed.

I guess this would be the time to mention that Gabriella has literally nothing besides the clothes on her back. I offered her my sweatshirt, hoping she'd wear just that and panties. However, she borrowed a pair of my sister's shorts. We all got into bed and it was a tight squeeze. Five minutes in, and I couldn't take being up against two bodies, under blankets, and cuddling with Gabriella in a sweatshirt. I complained and she got a t-shirt from my sister. It also felt much better cuddling with her. We were spooning facing away from my sister who was up against me facing the other way.

I readjust a lot while I'm trying to fall asleep, much to the dismay of my other two bed partners. This gave me a great excuse to move my hands over Gabriella. I kept touching her in different spots, running my hands up and down her thighs and feeling her hips and lower back. This went on for around fifteen minutes. I pushed my hips into her. Only wearing boxers, she could feel my dick against her ass and lower back. She pushed back in a wiggle motion. I slid my hand in between her legs, massaging her inner thighs. I removed my hand and placed it on her lower abs and pushed under the waistband of her shorts. At the angle I was at I couldn't finger her very well, so I just rubbed her pussy. She kept wiggling her hips back into me, letting out a slight moan. I froze and covered her mouth with my hand, reminding her my sister was next to us, literally touching me.

I eased back into it. Gabriella was soaking wet, and I was rock hard. I couldn't take it anymore. I eased down her pants and slipped my cock through the hole in my boxers. I grabbed it and rubbed it along her pussy. I put in the tip, but it was at an awkward angle and I had trouble with it. I grabbed her hips and thrust her back into me. We paused like that for a while. I relaxed and began to thrust, trying to stay as quiet as possible. I was having trouble as it was difficult to make it effective and silent. I laid back and grabbed Gabriella's hip and directed her back into me for her to take control. She reached around my neck with her arm and pulled me in for a kiss. She then went to work. Gabriella tantalizingly moved her ass along the shaft of my penis, wiggling her hips to simulate thrusting. I could feel every movement, every contraction. In all the times we've had sex, she's never been this wet. It was so hot. The small movements added to the hotness and how long I could last. After what seemed like forever, I finally felt an orgasm building. The situation was such a mental turn on. I told her and she flipped over and slid down the bed. Grabbing my cock and sticking in her mouth, she went to work. I put my hand on the back of head and gently guided her faster. I had, to this day, the most satisfying orgasm ever. I shot my jizz into her mouth. Normally, I'm not a big fan of kissing her after she swallows, but I immediately pulled her up and passionately kissed her.

I rolled onto my back and fell asleep with her on top of me. I guess the connection was back. To this day, I have no idea how "asleep" my sister was.

FIRST POST EVER. BE GENTLE PLEASE

I struggle with the flow in my writing so any constructive criticism is welcomed. I also don't about the backstory. I felt it was necessary but maybe you didn't. Thoughts?

EDITS - Formatting and broke it into paragraphs