I’ve been traveling quite a bit for work lately. I typically stay in hotels, but there was some sort of mix up this time. My company booked my hotel, but got the dates wrong. I showed up at the hotel in the afternoon and there was no room available for me and there were two major conventions in town, so there was basically nothing available at any hotel within a reasonable radius. I needed to find somewhere to stay for the next four nights. I went to plan b and booked a room at an Airbnb. The best I could find was a private room at this guy’s townhouse. The creep factor always crosses your mind, but he had a lot of good reviews and I didn’t have a lot of options. We communicated about when I would be able to come by to get a key and do a walk-through of the place. I was starving, so I stopped to eat first and then met him about an hour or so later.
I walked about ten minutes to the townhouse. When he answered the door I was pretty blown away. He was incredibly handsome. He had the typical small profile pic thing on Airbnb, but it was of him doing something outdoors with a hat on, so I couldn’t really tell much of what he looked like. He had black hair with a few grey/white strands of hair here and there. He looked mid 30’s. Five o’clock shadow. Piercing blue eyes. Henley shirt showing a slight bit of chest. He welcomed me in and introduced himself as Chris. I was a little flustered, but he was totally laid back and cool. It didn’t seem like he had even a passing thought about my appearance. Granted I had just gotten off of a plane and had been running around the city lugging my bags. I didn’t feel like I was looking my best. Either way, he was totally professional, but at the same time warm and welcoming.
He showed me around the townhouse. Typical stuff. It was a townhouse. He then led me upstairs to my room. It was the master and had a private bathroom in the room. Definitely nice to have. He showed me how to work the hot and cold water. It was kind of tricky. He mentioned that his girlfriend always has a hard time with it. My heart sank a little. Not that I even thought he was into me at all, but I was totally turned on by him. Just a bummer to hear he was off limits. My crush was dashed in only a few minutes. He showed me that the room locked from the inside. All was good. He went on his way and I got settled into my room. I showered and changed clothes. There was a work dinner thing I had to go to. Networking blah blah. I hate that type of thing, but it’s a necessary evil if you’re in the corporate world I guess.
I got to the dinner and was bored out of my mind within twenty minutes. I kept thinking about Chris and how sexy he was. I got stuck talking to this middle aged woman who kept asking me about my career path. She kept trying to give me advice for what to do when I get married and have kids. I kept politely going along with the conversation, but in reality I wanted to tell her that sounds like hell to me. I wanted to tell her there is no fucking way I want children and that I don’t see myself settling down with one man. I knew even if I said any of that in a nice way she would have thought I was a terrible person. She just gave off that vibe. She was a big shot with a company we do a lot of work with, so I just played the all-American role I was supposed to.
I made it through the rest of the night by drinking plenty of wine. I said my goodbyes and ordered an Uber back to the Airbnb. I fumbled with the keys and stumbled in the door a bit tipsy. Chris was sitting on the couch in the living area watching tv. I gave a warm hello and asked if I had a good night. I stood and talked to him for a couple of minutes. I was half honest with him. Didn’t want him to think I was a nut job. I told him the night was okay, but that a woman kept harassing me about having kids. He laughed. He told me I could sit if I’d like. I told him I should get to bed. Being a little drunk, I honestly wasn’t sure I could control myself from trying to flirt with him if I sat down.
I got up to my room and got ready for bed. Once I was in bed I had all kinds of sexual scenarios running through my head involving him. I started masturbating fully naked on top of the covers. I secretly hoped he would just barge in and catch me. I kept closing my eyes and imagining him standing there watching me. The door was locked, so I knew that wouldn’t really happen. Even if it wasn’t locked he wouldn’t barge in. It was fun to think about though.
The next morning I got ready to head to meetings. Showered and all of that. I crossed paths with Chris briefly. Again, just cordial brief conversation. I headed off to work. I felt exhausted the whole day. I had a little trouble sleeping, which isn’t normal for me especially after masturbating. I powered through, but was looking forward to getting back to the Airbnb for a nap.
I got back around 5:30pm and headed straight for my room. Chris didn’t seem to be home yet. I did one of those accidental long naps. I woke up at around 7:30pm super confused about where I was and what time/day it was. I slowly crept back into reality and got my bearings. I needed something to eat. I went downstairs to see if Chris was around to give me a recommendation on somewhere to go. He was downstairs doing some work on his laptop. He gave me a few suggestions. I said goodbye and headed out.
I ate alone. I’m not sure why I didn’t ask a coworker or anyone else to meet up. I’m kind of a loner, so I guess I just prefer it. I bought some wine on the way back. I figured I’d hangout in my room drinking wine and watching Netflix or something. I said hello to Chris for a minute and went upstairs. I came back down to ask for a wine opener. He gave me one and that was that. I kept hoping for some flirting or glance from him even if it was just for my ego. I was getting nothing. I know I know he had a girlfriend, but still he’s a guy and even taken guys look. I felt maybe I just wasn’t his type.
I went through 2/3 of a bottle of wine and two movies, but was still wide awake. My long nap really screwed me over. I figured I’d still try to fall asleep. It was close to midnight. I laid there for nearly an hour. I finally dozed off, but woke up wide awake again 30 minutes later. I was frustrated. I laid there for another 45 minutes. It was two something in the morning. I said screw it I’m awake I’ll watch some episodes of Seinfeld and drink wine until I get tired. I sat there on the bed for about ten minutes, but it began to be really uncomfortable. I had to shift around a lot earlier in the night to stay comfortable. The pillows behind my back and bed combination just weren’t great. Chris had said the living area was open for me to use if I’d like, so I figured I’d take advantage and go sit on the couch.
I threw on a long t-shirt and started to throw on some pants, but I didn’t have any that were good to lounge in. I started to just throw on jeans, but my devious side kicked in a little. I figured I’d just go with the long t-shirt and panties. The t-shirt hit about midway down my thighs, so it wasn’t too crazy. I knew he’d be asleep, so it was just a way for me to have a cheap thrill.
I crept down the stairs. All lights were off and he was in his room asleep like I assumed. I sat on the couch, opened my laptop and poured myself some more wine. I don’t know how long I was awake. I remember watching two episodes and having at least two glasses of wine. My next memory was being woken up on the couch by Chris. It was about 6:00am. My laptop was on the floor looking as if I’d dropped it from the couch. I was asleep on the couch kind of on my stomach kind of on my side with my left leg sort of in a triangle with my left foot against my right knee. My shirt was hiked up and the bottom part of my ass completely exposed and yes I had a thong on. I woke to him shaking me lightly by the shoulder. He also grabbed a blanket and covered me up. As I came to he was laughing. He asked if I had a rough night. I felt my cheeks turn bright red. I apologized and said I was so sorry. He was a total gentleman, but did make one little quip. He said it was quite a view to wake up to and chuckled. I truly hadn’t intended to fall asleep like that, but it did make me incredibly horny thinking about him seeing my ass exposed like that.
I hurried upstairs to get ready for the day. I ran into Chris again on the way out. He offered me coffee. I couldn’t stop blushing. He tried to make me comfortable. It did seem like he was more flirtatious with me all of a sudden though. He asked if I have a boyfriend back home. It could have just been small talk, but it seemed more curious. I told him I didn’t. I asked about his girlfriend. I was curious as to why she hadn’t been around at all in the couple of days I had been there. He said they had actually been long distance the last 7 months. She moved away for grad school.
I went to meetings again all day that day. My mind was preoccupied. I really wanted to have sex with Chris. I know I’m a bad person, but I just couldn’t stop thinking about it. I got back to the Airbnb around 6:00pm. Chris arrived about ten minutes later. I asked him what he was doing that night. He said he was just going to answer some emails and then relax. I asked if I could hangout on the couch and watch some TV. He said it was totally cool and wouldn’t bother him at all.
We talked and just relaxed. We both had some wine. We didn’t really watch TV at all. We both started to get pretty comfortable with each other. We talked about life and our backgrounds and all of that. I started asking him about his long distance relationship and how it was going. Yes, I was prying. He was open to talking about it though. He told me it wasn’t ideal and that it was a tough transition. I just went for it and said I’m sure it doesn’t make it any easier when you wake up to a half-naked woman on your couch. He laughed and sort of shifted in his seat. He said that was definitely not easy to see. I took a big gulp of wine and I asked if he liked what he saw. He sort of shrugged and said, come on, or something. He said yeah, of course he did. Said something about being a red-blooded male and how could he not.
I don’t know what came over me, but I just went for it. I moved from my side of the couch to his. I lunged toward him and kissed him. He didn’t stop me. He kissed me back hard. We kissed for a while before he pushed me back a little and told me we had to stop and that he couldn’t do this. I was still breathing heavy and feeling on his chest. I told him I understood and I backed away. I sat back on the other side of the couch. He got up and went to the restroom. He walked back into the room and didn’t say anything. He just walked up to me. Pulled me up from the couch and started kissing me again and telling me how sexy I was. I was soaking wet and aching for him to fuck me.
We continued kissing and he had his hands all over my ass. He unbuttoned my pants and slid them down my legs. He kept muttering about how much he loved my ass. I groped his cock through his pants. He was very hard and I desperately wanted him inside me. I unbuttoned his pants and pulled them off. His cock was bulging against his underwear. I pulled it out and stroked it with my hand. He turned into an animal once he felt me stroking him. He stripped all of my clothes and his off. He pushed me face down onto the couch. He got behind me and went face first into my pussy and ass from behind lightly biting my ass cheeks and licking my clit and ass from behind. He again kept muttering about how much he loved my ass. I could feel his five o’clock shadow rough up against my skin. I was gushing with wetness.
He stopped with a panicked look. He said he didn’t have any condoms, because he only ever has sex with his gf and doesn’t use them. I said I didn’t care and that I just wanted him to fuck me. I was still bent over soaking wet when I felt his girthy cock press up against my pussy lips. I had a split second of feeling really guilty when I thought about what his gf would think if she knew what was going on, but it also turned me on as bad as it sounds. It made it all feel even dirtier. I hadn’t been so turned on in a really long time, which is saying something. He fucked me slowly. Every inch grinding in and out as he stared down at me. I reached my hand back toward my ass and began fingering my ass as he fucked me. I thought it would turn him on and it did. He was talking dirty to me and telling me to fuck my tight little ass. He only lasted a few more minutes. He never really picked up the pace and I didn’t cum, but I really didn’t care. It was so fucking hot. He slowly slid his cock out of me and I felt warm drops of cum landing on my ass and hand as I continued to finger my asshole and shove his cum in my ass. I turned around and sat on the couch as he stood and took his cock in my mouth. I sucked every last drop out of him. He kept saying he couldn’t believe he just did that.
He said he needed to go to bed. He kept apologizing to me for some reason. I felt like he was really apologizing to his gf. I went upstairs to get ready for bed and masturbated since I hadn’t gotten off. I did wake up the next morning feeling conflicted. He played it cool that next morning and sincerely wanted to make sure I understood that’s not something he ever does or has done. A lot of guys say stuff like that, but I actually believed him which made me feel good and guilty at the same time. I assured him I wasn’t going to say anything. I went to work and thought about the night before all day. I went straight to the Airbnb after work and arrived around 5:30pm. He wasn’t home. I figured he might avoid me since it was my last night and he probably felt like shit about what he did.
He got home around 6:30pm. I was upstairs, but had my door cracked. He came by my room and lightly knocked as he pushed it open. We didn’t even say anything to each other. We were just all of a sudden up against each other pulling our clothes off. It seemed like we had both been thinking all day about how hot the night before was. I was soon laying stomach down on the bed with him standing beside it with his cock down my throat. He was reaching over fingering my pussy and ass. He had soon flipped me around. I was on my knees on the bed with the back of my thighs touching my calves and my ass hanging over the edge of the bed. He slid his cock in me again, but fucked me hard this time. He fingered my ass with two fingers as he did it. I could tell what he wanted, because he was so obsessed with it. Not that I was complaining. He eventually asked me if he could fuck my ass. I asked if he had any lube. He was back in a matter of seconds with some. He was soon inside me slowly pushing my ass open wider as he went further in. I worked my clit with my fingers as he slowly thrust in and out of me. It wasn’t long before I came and my asshole twitched and tightened on his cock. He muttered about how sexy I am and told me he wanted to fill my ass up. I told him to please fill me with his cum. I had barely gotten the words out of my mouth when he started moaning and shooting his cum in my ass. I was completely spent and felt used up in the best way. I fell to my stomach on the bed. He grabbed and caressed my ass cheeks with both of his hands. He gave me like a mini ass massage for a couple of minutes that felt amazing. He left the room without saying anything.
I laid there for a bit just gathering myself. I eventually went downstairs, because I was hungry. He had showered and was walking around in his underwear. He said we should order food. We didn’t. I started sucking him off again. I had to pee, so I ran back upstairs. I forgot I had brought a lingerie thing. I thought I’d be dirty and come back down with it on. I made it down the stairs in my sexy outfit and motioned for him to come back up. He said oh my god or something and followed me upstairs. We had sex off and on the rest of the night.