Anal on the roof with hotel hostess [MF]

Long story with some background before the night in question. It culminates in an admittedly far fetched story, though I can assure you it’s true.

In my first job, I traveled a lot, to the same hotel for about a year and a half. When I joined the team, many had already been staying at the same hotel for months, so they knew the hotel staff quite well. They quickly introduced me to the front desk staff, including a girl named Jen. Jen was super helpful and got me hooked up with hotel status earlier than I would have otherwise.

Jen was hot and had done some amateur runway modeling. She was about 5’8″, brunette hair partway down her back, thin, perky ass, and large B / small C tits. (Also later found out she’d tan a lot and often had the outline of a little sticker she’d put on her hip before she’d go in the tanning bed.) I was a young guy, so I was interested. I learned that Jen had messed around with a colleague of mine several months prior. Now, I’m not the type to really hold people’s past experience against them as long as they’re clean, so I wasn’t put off. In fact, I was actually more interested – it meant she was down to play with hotel guests.

A few months after I started staying at the hotel, I was annoyed I’d been a bit too cowardly to make a move on a friend who kept giving me chances. So, to remedy the situation, I marched down to the hotel front desk and asked for Jen’s number. She furtively looked around and made sure nobody noticed, then quickly gave me her number and told me nobody at work could know.

I’ll spare you the details of the first few dates, but suffice it to say we became a thing. I’d switch hotels for one night every week or so, and she’d come spend the night. She and I were still getting to know our own kinks, but I quickly learned she really liked getting spanked (and would demand it during sex if I wasn’t heavy handed enough). Over time, we figured out she also loved getting choked and having her long hair pulled. I was also particularly into playing with her perky ass. It started out with rubbing, which she seemed embarrassed to admit she enjoyed. However, I took it further, and would lick my finger and work it into her tight asshole. We eventually decided we need to try full on anal.

The night came – I talked my way into a suite at the other hotel we were staying at. We were in our early 20’s and still drinking 4 Loko (in an ironic way, but still embarrassing). So, we split a 4 Loko and settled into the large tub. I was trying to help her relax, lathering her up with soap and playing with her butt a bit, both to get her ready, and because we figured we had to prep somehow. Eventually, we toweled off and found ourselves on the bed. We lubed up and I got on my back. I was eager to watch her slowly sit down on my cock – we figured this position would give her the most control. After a couple hesitating attempts to work my dick in, she said she couldn’t bring herself to do it. However, rather than give up, she told me she wanted me to push my dick past the resistance, into that sweet ass of hers. I certainly didn’t need any more encouragement, so I got her on her hands and knees, and watched as I slowly pushed my dick into her. It was amazing…I loved every minute of it and marveled at how the tightness allowed me to feel every ripple. The best part was that she also loved it.

Thus began our adventures in anal. Anal became a regular part of our sex nights. A typical night was see us start off with some oral on her beautiful and always smooth pussy, before I’d fuck her. Then I’d push my dick into her and lock eyes with her before choking her, and giving her a few slaps across the cheek (which we found out she also enjoyed). Then the main show. I’d pull out, shove my dick into her mouth to watch her lick her juices off and get it as wet as she could. I’d spit on her ass and slowly push in. We’d use lube when we had it, but it turns out a lot of spit also worked pretty well for us. We were careful about not switching back to another hole, which meant I’d almost always get to finish in her ass.

This ongoing arrangement reached its peak on a particularly hot night. Her manager invited my team to a hotel staff party, so I got to see Jen all done up. She was staying in a nearby hotel with her best friend to avoid having to drive home, so after the event, I walked over from the hotel she worked at (staff wasn’t allowed to stay at the hotel they worked at). Since her friend was staying with her, the room wasn’t an option for Jen and I. Thankfully, Jen also had a thing for sex in public. We ended up exploring the hotel a bit before finding out that the roof had an unlocked door. Soon enough, I had her bent over an AC duct, fucking her pussy. The next part is odd, but I swear it’s true. As I’ve got her bent over, a Southwest 737 flew overhead with it’s final approach lights on…we were only about 1/2 mile from a regional airport. Now, I won’t ever really know, but I’ve got to assume that the pilots could have seen us if they were looking at that moment. I let out a sort of guttural yell as it happened and gave her ass a nice slap. Given her kink for public sex, she was going wild.

Shortly thereafter, I spun her around with the intention of blowing my load in her mouth, but I misjudged and blew it on the roof before I could get into her mouth. She still sucked me clean, but it wasn’t quite the same. We were both a bit bummed I couldn’t fill one of her holes, but we were getting cold.

We went inside to the little room at the top of the stairwell that opened onto the roof. The hotel used it to store linens, so there were some carts full of towels. They made a soft surface to push her up against and start making out. One thing led to another, and soon we were going at it again. However, I’d already had her pussy and mouth, so when I bent her over again, I made sure to drizzle some spit on her asshole and slowly push it in. Now, even at that age, I had a refractory period. I was still quite hard given how hot the situation was, but I was taking awhile to finish. At first, this made it wonderful – I was sensitive, so I was feeling everything and wasn’t worried about blowing prematurely. However, I did eventually want to feel another orgasm wash over me. I wasn’t sure I’d get there, so I started focusing on my inner monologue, “holy shit – you’re roughly fucking a gorgeous runway model in the ass in a linen closet.” That did it, and I was eventually able to fill her up.

I stumbled back to my hotel room and passed out. When I woke up, I saw she’d texted me to come back. I often think about whether her friend would’ve been up to watch a third round.

She ended up meeting someone about 2 weeks later. She and I continued to hook up for a few months after that, but it slowly tailed off as she got serious with him. It was really an amazing few months, though.

​

​

​

​

Source: reddit.com/r/gonewildstories/comments/appk8q/anal_on_the_roof_with_hotel_hostess_mf