(m)y first time anal, while girlfriends pregnant sister slept (f)our feet away | 2016

So a little back ground. This happened a few year back when I was 19. I was about 5"11 with long black hair (scene style) with a few piercings and tattoos. A little on the chubby side. And my girlfriend, Donna was the same age, quite petite, blond and black scene hair with so many piercings. Tits that were a perfect handful and an ass to kill for.

Donna and I have been dating for about 3 months when this story begins.

Donna had a family wedding coming up, it was to take place up in the mountains. A nice little town. But it was about a 4 hour drive and Donna didn't drive so that fell on me. I haven't really met any of her extended family before so I quite nervous. But anyway, Her sister, let's call her Brianna was 17 and she was 7 months pregnant. Not bad too look at either, also didn't drive so she tagged along with us.

We decided that the 3 of us would just share a hotel room to save some money. Which was fine with me. So we get there, get our room. Claim our beds and get ready for the wedding. The wedding is unimportant so well just skip passed that. After the ceremony was a lot of drinking. Brianna didn't partake for obvious reasons so she went back to the room to go to sleep. Donna and I stayed up drinking for a while longer and decided it was time to call it a night. So we go back to the hotel room. Crawl into bed and I'm sure it was from the wedding but she was so turned on we started heavily making out. We were spooning, me behind her. She was wearing this super sexy pair of booty shorts,and a black tank top. Needless to say, I was quite turned and her grinding her amazing ass into my cock wasn't helping. I could feel myself growing. Things started getting hotter and hotter and she started stroking my cock over my boxer briefs. This is when I came to the realization that her prego sister is sleeping 4 feet away in the other bed. I felt bad, but in a good way. I've never done anything like this while someone else was in the room. And she seemed to be out cold so we continued. And in all honesty it was quite hot knowing she could wake up any second and see us. I was rubbing my hands all over her petite body. Exploring her from head to toe. Kissing her neck while she grinds Into me. I was so hard at this point. I just needed to fuck her right Now! So I grabbed her panties and she arched up and I said them off. My God, her shaved pussy was amazing. It was so little, and neat. I loved it. And I removed my boxers,get back into spooning position (because it seemed the most stealthy position) and she grabbed my throbbing cock and rubbed it along her slit. It was so wet. I could feel it dripping all over her legs. It was unreal. I loved it. She guides my cock inside her, slowly. And I start thrusting myself into her, all the while looking over her shoulder to make sure her sister was still asleep. We were facing right at her. The whole situation seemed so wrong, but there was no way we were going to stop. She felt way to good. We start building up momentum and her moans that started out really quiet were getting louder. So I used my hand to cover her mouth while I slid inside and out. Faster and faster. I could feel Donna start to clench up and her breathing got really fast. She reached back and grabbed onto my hip and pulled me toward her to get as deep as I can, and she came. Hard. I swear her nails were going to leave scars on my side. Now that she has gotten off It was my turn. I start thrusting harder and harder and I'm getting close when she stops and pushes me away. I was a little confused, i thought maybe her sister woke up. But then I feel her hand grab my cock by the base and tease her asshole with it. (we discussed anal, neither of us have done it before and I didn't think it would ever happen with her) she was so wet that she used my hard cock to guide some of her delicious pussy juices toward her ass. We didn't have any lube or anything. But she was so wet she just went for it. She lined up the head of my dick against her tight ass hole and leaned into it. It felt amazing! It was so tight. And she was so wet there was no friction. Went in way better than I expected. She slowly backed into me until all of my cock was inside her. (I'm not a very large man, about 5.5 inches, but I was still surprised she took it so well) and I started thrusting into her. Grabbing her hips to get a better angle. I keep looking over at her sister. She was still asleep. Good. The last thing I would have wanted is to stop this half way through. It felt way to good. I continue fucking her ass, slowly at first but building momentum quite quickly. She was letting out these unbelievably sexy little whimpers. I could tell she was trying to be quiet. I keep thrusting. I'm getting close. I can feel the ponr approaching. And I think she could feel my cock starting to pulse, she leaned her head back and whispered in my ear "I want you to come in my ass babe" and that's all it took. Maybe two more pumps at most and I was unleashing my load deep in her ass. All while looking at her sister 4 feet away. It felt so good, I let out a quite loud moan of pleasure. I couldn't contain myself, the combination of being inside her ass for the first time and seeing her sister right there turned me on beyond belief. Thinking how sexy it was that we could get caught with my cock inside her ass. But luckily she did not wake up (or maybe she did and was listening, who knows) we just kind of laid there for what felt like a few mins, but was probably more like 15 secs. My cock still pulsing inside her ass, I slid it out and I could feel all of my juices rushing out of her. It was amazing. Donna then got up to go to the bathroom to wash up and I smoked a victory bowl while I laid there. Blown away at how amazing it was.

I'm sorry if this was badly written. I'm a long time reader and wanted to share one of my stories that I think back on quite a bit. Hopefully you liked it.