Straight Male / 19
A Cougar Took Me To Her Hotel
I work a couple of customer service jobs in a tourist town. The jobs are always seasonal and nobody wants to pay fulltime benefits so I bounce between a few places including a restaurant.
At couple months ago, I was serving two families that were friends. One of the mom's was recently divorced as she made a point of telling me while I was serving them. In fact she made a point of flagging me down to talk to me. She was very direct, that she was interested, to the point where everyone else was getting visibly uncomfortable, especially her own kids. She left a big tip and wrote her number on the check. My coworkers teased me mercilessly, my female coworkers thought it was hilarious because that sort of thing happens to them all the time. Honestly I am pretty shy sometimes so I was not super comfortable with what had just happened either, maybe if it had been less public I would have been more comfortable.
As embarrassed as I was I wanted it though. She was late 30's, early 40's, latina or mixed ethnicity and a bit above average looking. She had long black hair, was maybe a foot shorter than I was but had the confidence to seem much bigger and while she was starting to gain weight, she was still very much on the curvy side. It honestly triggered all of my fantasies about older women that I have had for years.
After my shift I texted her number, we talked. She was pretty direct and gave me her room number after a few messages. I hadn't even gone home yet so I walked over to her hotel, knocked on her door and she answered wearing a robe. I came in and when she closed the door she dropped the robe revealing that she was wearing the kind of lingerie nobody my age could afford. I managed to get out that she looked incredible and she said "I know" with the same confidence that helped make her so attractive. She helped me out of my clothes. It was a little awkward and we laughed and flirted a bit as we did that. Then she led me over to the bed and she laid down on a towel she had laid out and guided me on top of her, I kissed her for a bit before exploring with my mouth further and further down her body. She grabbed my hair hard which honestly made me super turned on and she guided my mouth between her legs. I ate her for what felt like forever, I couldn't get enough. Normally pubes on a woman aren't my favorite but I thought it made her even hotter. Eventually pulled me off, Leaned down, kissed me despite my face soaking with her and she had me lay on my back.
I thought it was going to be her turn to go down on me but instead she sat on my face which turned me on even more. She grabbed my hair, rubbing her clit on my nose and squeezing my ears with her thighs and I couldn't breath but I was in heaven. I have had femdom fantasies for years and this was like living them all out at once.
She eventually came enough times and got off me. She got between my legs and started sucking me. To say she was better than the girls my age would be a giant understatement. I had to stop her really quickly because I didn't want to cum. She pulled back and licked my balls for a bit to let me recover, then I felt her tongue go lower. She started rimming me and it felt like nothing else. My moans were suddenly a lot more high pitched. She did it for a while before asking me if anyone had ever done that for me before and I told her no but I had always wanted it. She told me to get on my hands and knees doggystyle and I did. She got behind me and continued to rim me but also started to stroke my dick as it hung underneath me. I came so quick and so hard that I just collapsed. I got super sticky from lying in my own cum but at that moment I didn't care about anything. She crawled on my back and kissed the back of my neck as I came down from it.
She eventually rolled me over and she licked me clean which brought my dick back to life faster than I ever thought possible. Then she reached over to her purse and got out a condom. She put it on me, pulled her panties to the side and rode me like there was no tomorrow. Honestly it felt amazing and she looked super sexy riding me but it wasn't as good as what I had just experienced. Especially with a condom blocking the sensation.
We finished and she basically kicked me out. As I got dressed again I realized that the room was connected to another by an interior door. I about died of embarrassment again realizing her kids were probably in the other room and I did the walk of shame out of the hotel.
She lives several states away so I doubt I will see her again but holy shit, she rocked my world and I think about the embarrassment and how amazing it was almost every day.
At couple months ago, I was serving two families that were friends. One of the mom's was recently divorced as she made a point of telling me while I was serving them. In fact she made a point of flagging me down to talk to me. She was very direct, that she was interested, to the point where everyone else was getting visibly uncomfortable, especially her own kids. She left a big tip and wrote her number on the check. My coworkers teased me mercilessly, my female coworkers thought it was hilarious because that sort of thing happens to them all the time. Honestly I am pretty shy sometimes so I was not super comfortable with what had just happened either, maybe if it had been less public I would have been more comfortable.
As embarrassed as I was I wanted it though. She was late 30's, early 40's, latina or mixed ethnicity and a bit above average looking. She had long black hair, was maybe a foot shorter than I was but had the confidence to seem much bigger and while she was starting to gain weight, she was still very much on the curvy side. It honestly triggered all of my fantasies about older women that I have had for years.
After my shift I texted her number, we talked. She was pretty direct and gave me her room number after a few messages. I hadn't even gone home yet so I walked over to her hotel, knocked on her door and she answered wearing a robe. I came in and when she closed the door she dropped the robe revealing that she was wearing the kind of lingerie nobody my age could afford. I managed to get out that she looked incredible and she said "I know" with the same confidence that helped make her so attractive. She helped me out of my clothes. It was a little awkward and we laughed and flirted a bit as we did that. Then she led me over to the bed and she laid down on a towel she had laid out and guided me on top of her, I kissed her for a bit before exploring with my mouth further and further down her body. She grabbed my hair hard which honestly made me super turned on and she guided my mouth between her legs. I ate her for what felt like forever, I couldn't get enough. Normally pubes on a woman aren't my favorite but I thought it made her even hotter. Eventually pulled me off, Leaned down, kissed me despite my face soaking with her and she had me lay on my back.
I thought it was going to be her turn to go down on me but instead she sat on my face which turned me on even more. She grabbed my hair, rubbing her clit on my nose and squeezing my ears with her thighs and I couldn't breath but I was in heaven. I have had femdom fantasies for years and this was like living them all out at once.
She eventually came enough times and got off me. She got between my legs and started sucking me. To say she was better than the girls my age would be a giant understatement. I had to stop her really quickly because I didn't want to cum. She pulled back and licked my balls for a bit to let me recover, then I felt her tongue go lower. She started rimming me and it felt like nothing else. My moans were suddenly a lot more high pitched. She did it for a while before asking me if anyone had ever done that for me before and I told her no but I had always wanted it. She told me to get on my hands and knees doggystyle and I did. She got behind me and continued to rim me but also started to stroke my dick as it hung underneath me. I came so quick and so hard that I just collapsed. I got super sticky from lying in my own cum but at that moment I didn't care about anything. She crawled on my back and kissed the back of my neck as I came down from it.
She eventually rolled me over and she licked me clean which brought my dick back to life faster than I ever thought possible. Then she reached over to her purse and got out a condom. She put it on me, pulled her panties to the side and rode me like there was no tomorrow. Honestly it felt amazing and she looked super sexy riding me but it wasn't as good as what I had just experienced. Especially with a condom blocking the sensation.
We finished and she basically kicked me out. As I got dressed again I realized that the room was connected to another by an interior door. I about died of embarrassment again realizing her kids were probably in the other room and I did the walk of shame out of the hotel.
She lives several states away so I doubt I will see her again but holy shit, she rocked my world and I think about the embarrassment and how amazing it was almost every day.
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# 67991 - by
Adroit07 / October 6, 2023
