My NYE Fun part 1 [m/f] | 2016

Long time fan of this subreddit and up until the last few days I really had nothing to add to it but now I have a story that hopefully you will like. I’ll give a bit of a background first. I’m 24 and a decent looking guy, about 5’11 and pretty thin. I work out from time to time but I’m not exactly the most impressive looking guy without a shirt on. I’ve had a few girlfriends but my sexual conquests outside of them consist of just one other girl who I had a fwb relationship with for a few months.

For New Years Eve this year my friends and I booked a trip to Vegas. We had gone last year and it was an absolutely amazing time. The original plan was for 8 of us to go, 3 couples and two other guys and we were staying in two rooms. I was a part of one of those couples until the middle of December when my gf and I broke up, which is really shitty timing with the holidays coming up. We couldn’t find a replacement so the group was just 7 now and I would be sharing a room with my friend and his gf. We got there on Friday and after checking in we went down to the casino to gamble. I’ve never been a big gambler but I was doing pretty well and at the end of the first day I was up a few hundred. We went out that night and this was my first real chance to get out and talk to girls since my relationship ended. Between not trying to pick up girls for over a year and lack of game to begin with I was just a little rusty. I talked to a few cute girls and danced a little but the night ended without anything more happening. It didn’t make things easier that in the middle of the night I was woken up to the sounds of my friend in the next bed having sex. Obviously they were not as discrete as they thought or just didn’t care. I didn’t mind because his gf is really hot so hearing her moan is a turn on and since I had seen naked pictures of her I had a pretty good mental image of what was going on. Unfortunately I didn’t feel comfortable jerking off right there so I went to bed horny.

The next day was similar; we went to gamble while the girls wanted to check out some of the stores in the area. Luck was still with me and by the time I had my fill of betting I was up about $500 more. At night we were going to another club and since I was still backed up from yesterday I was desperate to make things happen. I had even convinced myself to settle for a less attractive girl then I would normally go for, I just needed to have sex. Despite my best efforts and the help of the two girls with us it was just not happening again. I decided to bail on the club before my friends and went back to the casino since it was the only place I had luck. I was pleased that was still holding true and when I left the table around 3am I had another $300 in my pocket, making this by far my most successful trip to Vegas. I was loading up on drinks at the table and I had a really solid buzz going. I was talking to my friend that I shared the room with to see if they were still out, which they were. I had no desire to walk in on them right now.

I’m waiting for an elevator to come take me up to the room when one coming down opens. A really cute girl, probably in her early to mid 20’s, walks out and I just start talking to her. She was almost walking away but then came back to me. She was wearing a light sweatshirt and jeans, definitely not clothes she would wear out to a decent place. I don’t even remember exactly what I said but this random encounter was going far better then any of my other attempts with girls this trip. She told me her name was Amber and this is when I first became suspicious, I’ve only seen girls with that name in strip clubs. That combined with that fact that she seemed so interested in me out of the blue and I made that connection, she’s a prostitute. This was confirmed a minute later when she was about to leave saying she has to go make money. Without thinking I blurted out, “How much?” I never would have considered getting a prostitute but in the moment I just wanted it. She told me to hold on for a second and went a few feet away and made a quick phone call, I’m guessing to a pimp or whoever was waiting for her, I think that’s how these things work. When she hangs up she calls another elevator and we get in and on the ride up to my floor we agreed on a price and since I was up so much I had no problems paying for this. I texted my friend and told him to stay out for another hour and then led her to the room. She asked for the money right away so I dug into my pocket to get it and then went over to the table and poured out a shot, I needed a little bit of courage right now. I turned to offer her one as well and I saw her taking off the sweatshirt. She just had a bra on underneath and after saying she’d take a shot too she undoes her jeans and pulls them down revealing a black thong.

I pour the shot and hand it to her and we both drink up. She tells me to take off my clothes and get on the bed. I comply and watch her as she takes off her underwear. She was a very petite girl, skinny with small but nice boobs, a decent ass, and a shaved pussy. I lay on the bed and she crawled up and starts touching my dick. I was already filling up but the second her hand touched me I got rock hard. She kept saying things like how nice and big my dick was but I just chalked this up to what she always does considering I’m pretty average. She strokes me for a minute or two before grabbing a condom and putting it on with her mouth. She went on to give me a blowjob but with a condom I think its kinda silly. I had the thought of pushing her over onto her back and going down on her but then I remember, she’s a prostitute who in all likelihood had sex with someone else that night. I was not trying to put my tongue somewhere another guy’s dick had been only an hour ago, and I wouldn’t trust that’s she’s clean anyway. So I try to enjoy the blowjob before I tell her I want to fuck.

She straddles me and lowers herself onto my dick. She moved herself up and down, sliding me in and out of her. My hands went right for her tits and I gave her nipples a squeeze. She was soon fucking me faster and moaning as she did. It was very easy in that moment to forget that I paid for her and that her pleasure really didn’t matter; she’s very good at her job to make me forget. I tell her to get on all fours and when she’s in position I thrust into her hard from behind. This is my favorite position and I do not hold back at all. I am fucking this girl as hard as I can and the slapping sounds our bodies make and her moans only encouraging me. Without thinking I reach for her hair, my ex loved her hair pulled in this position and it is just an instinct for me. I was happy she didn’t stop me and instead she reached back and rubbed her pussy while I fucked her really hard. Her moans were getting progressively louder which I assumed was her faking it but to my surprise I felt her cum as her pussy squeezed around my cock. Now I’ve always been good about getting the girl I’m with off but I was not expecting her to cum. I didn’t care that it was probably her hand rubbing her clit that made her cum, I felt awesome that a prostitute came while having sex with me. I guess that’s pretty much what did it because in another 3 thrusts I buried myself deep inside her and came so hard. She moaned with me and when I was done I pulled out and threw out the full condom. I lay back on the bed as she got dressed and went to the bathroom. She asked how long I was in town and wrote down her number saying she was available every night except New Years Eve before she said bye and walked out the door. I lay there for a few minutes just thinking about what I did but it was totally worth it. I texted my friend to let him know it was safe to come back up before jumping into a quick shower to clean up.