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Sharing a Hotel Room With Lindsey

Posted by: Age: 23 Posted on: 1 comments
2 likes 1293 views Category: Masturbation Male-Female Tags: Caught


Two years ago I was on a sports trip out East. Our team was really small and by chance, with the way the numbers worked out, I ended up having to share a hotel room with Lindsey. I've known Lindsey for a long time and have always kind of had a crush on her, so I was actually (in secret) super excited to share a room with her!

Lindsey was a cute brunette. She had a nice smile, a cool personality, and being an athlete; she had a pretty tight body with a super nice ass and legs. Her breasts are on the small side but I thought they were perfect as I'm not a big fan of big breasts anyways. Often times though, you could see her hard nipples through her shirt, which was always a turn on.

The trip was going well and we were having fun hanging out with each other, except for one small problem. As the trip went on I was getting hornier and hornier from being around her and without much privacy there was not much I could do about it. After one sleepless night I was able to bring some relief by masturbating in the shower later that morning, but that only held me over for another day or two. Soon though, I was having trouble sleeping again at night due to being so turned on. Seeing Lindsey hanging out in the hotel room most of the day in usually just short shorts and a tight t-shirt was starting to drive me crazy! My mind was constantly thinking about how badly I wanted her and trying to fall asleep every night with a throbbing erection while she was lying in the bed next to me wasn't easy to say the least.

One night we went to bed and as usual, I lay there with a hard on trying to fall asleep. I couldn't stop thinking about Lindsey and the images that I had seen during the last few days were running wild through my mind. Seeing Lindsey bend over and being able to clearly see her panty lines against her tight little ass, or getting the occasional glimpse of her panties through the top of her jeans was a huge turn on for me. I couldn't help but wonder and fantasize what her pussy looked like, as over the course of the week that was basically the only thing left to my imagination as I had more or less seen everything else whenever she was wearing tight clothing. Did she shave her pussy smooth, leave a bit of hair, or maybe she preferred not to shave at all and liked the feeling of having damp and sticky pubic hair when she got wet and turned on? Maybe she was also lying in bed each night feeling as horny as I was and maybe she would wake up each morning wet and with her panties full of her pussy cream?

In no time I felt the familiar drip of precum from my cock. After we were in bed for about half an hour or so I knew I wasn't going to be able to fall asleep. I looked over at the silhouette of Lindsey in her bed and she was lying on her side facing away from me. She looked to be asleep so I reached down and gently ran a fist up and down my cock. I slowly squeezed from the base of my cock to the tip and felt the precum begin to ooze out. With my thumb, I spread the slippery stickiness over the head of my cock and continued to stroke while trying to be as quiet as possible. This felt so good and brought on the feeling of such needed relief that I couldn't stop here. I began to breathe heavier while I started to stroke faster and more rhythmic until a few minutes later when I heard Lindsey roll over in her bed to face me. I should have stopped there and pretended to be asleep but I just couldn't and had lost all inhibitions at this point. Next thing I knew I was slipping off my boxers and was totally naked with the sheets and covers down to my knees, my legs spread, and I was masturbating full on while thinking about her. I wasn't sure is she was asleep at this point or not but I soon found myself wanting to make it obvious as to what I was doing in the event she was awake. By this point I was breathing heavy, I was stroking my cock hard and fast, and the now sticky sound my precum made while my hand moved up and down my shaft was loud and left no doubt as to what I was doing. She would also have been able to clearly see the silhouette of me stroking my cock if she were to open her eyes as well.

I wasn't going to last long at this rate so I started to pause briefly every once in a while to draw out my orgasm and kept this up for maybe another 15 minutes. At one point while I paused I'm pretty sure I saw Lindsey's hand move down to her crotch and heard her hand slip under the waistband of her shorts or panties. Not long after that I could start to hear her breathing become a little louder and I thought if I listened carefully I could hear a sticky sound every once in a while but I could be totally wrong. I have no idea if she was masturbating or not. It was too dark for me to see from my side if her hand was moving around her pussy, so if she was rubbing herself she was very subtle about it. At the time I liked to think she was and the thought of her discretely rubbing her wet pussy and fingering herself or rubbing her clit was more than enough to put me over the edge. I began to stroke my cock again and pumped it vigorously for maybe 20 seconds or so before completely blowing my load and cumming all over my stomach. I wiped up my cum with one of my sheets and then for the first time that trip, I quickly fell asleep. The next morning I couldn't help but feel a wave of guilt and embarrassment when she commented how she slept well but it took her forever to fall asleep. I'm not totally sure, but maybe that was her way of hinting to me that she was awake and knew what had happened shortly after we went to bed!



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