Straight Male / 29
Sleepy Humping
When I was about 26 years old, I had taken a liking to escorts. There was one particular escort I had been a regular of. Her name was Jessica and we had formed a friendship over the few times we had seen each other. And what I mean by that is that if I ever needed someone to talk to then she and I would meet up at the hotel to just talk; she never wanted money when we just talked. She was a single mother who had an average body, and when we did fuck then it was pretty passionate; at least, more passionate than escorts I had seen before were.
This one particular night, I needed someone to talk to. I texted her and asked if we could hang out because I needed a listening ear. She invited me over to the hotel she was at. I took a condom just in case, even though she always gave me one if we fucked. It was super late when I got there and she let me in. She was wearing a black, silk shower robe. She said that she was super sleepy, but she was more than happy to listen to me. I offered to come back the next day, but she declined. So I sat on the bed and she lay down on her stomach and we talked and talked for a good thirty minutes. Towards the end of the thirty minutes, she was falling asleep. I had adjusted a bit on the bed and she would wake up. Again, I offered to leave, but she said no. So I kept talking and noticed her eyes were closed and she was breathing deeply.
I stared at her and I really noticed her body; her legs looked so soft. Then I noticed the way that she was lying caused her silk robe to ride up. I saw that she wasn't wearing panties. I got hard. I adjusted my hard cock, which caused me to move on the bed. She didn't stir. I tried shaking her a bit to wake her up, but she didn't move. I called her name and she didn't respond or stir. It was this time that I got bold. I reached the bottom of her silk robe and pulled it up to expose her nice, round ass. I stared at it for a minute then slowly moved my hand over her ass cheeks. As I did this, I wondered what I would tell her if she suddenly woke up. However, the more my hand rubbed her ass, the further my fears got away. I rubbed her ass while rubbing my cock through my pants.
By this time, my cock was bursting through my pants so I decided to throw caution to the wind. I got up from the bed; she didn't move. I went around the bed to where I could get a better look at her bare ass. I lifted her robe up further and spread her ass cheeks. I then took my phone out and took a few pictures of her. After this, I took the condom out, took my pants off, put the condom on my cock, and climbed on top of her, slowly. My heart was beating super fast at this time, but it was more out of excitement than nervousness.
I slowly slid my cock between her ass cheeks and grinded on her slowly. She didn't move or give any indication that she was awake. I continued grinding, but stopped to get my phone out to record my cock gliding between her ass. I stopped recording and kept grinding. I kept this up for a good four minutes, moving slowly because I didn't want to risk waking her up. I came a lot in the condom that I thought it was going to leak out. I had wanted to put my cock in her pussy, but I didn't want to press my luck. I climbed off of her and took the condom off, put my pants on, and flushed the condom down the toilet.
It was during this time that I realized what I had done; and how hot it was. I gathered myself together and looked at her still sleeping. I gave her a kiss on the cheek. I decided that I should leave so she could continue to sleep. I opened the door and it made a loud sound as it opened. I turned to look at her and she woke up. She looked around the room for me and she turned around and asked what I was doing. I told her I was leaving and she got up and said she would tell me to stay, but she was so tired. I told her it was okay. She gave me a hug and I left.
In the following days, I relived that moment through my memories, the pictures, and video. Sadly, I didn't keep the pictures and video because I had gotten into a relationship not long after and so I deleted them, without remembering to save them. I did see her one more time after that, but I always remember that night I had fun with her while she slept.
This one particular night, I needed someone to talk to. I texted her and asked if we could hang out because I needed a listening ear. She invited me over to the hotel she was at. I took a condom just in case, even though she always gave me one if we fucked. It was super late when I got there and she let me in. She was wearing a black, silk shower robe. She said that she was super sleepy, but she was more than happy to listen to me. I offered to come back the next day, but she declined. So I sat on the bed and she lay down on her stomach and we talked and talked for a good thirty minutes. Towards the end of the thirty minutes, she was falling asleep. I had adjusted a bit on the bed and she would wake up. Again, I offered to leave, but she said no. So I kept talking and noticed her eyes were closed and she was breathing deeply.
I stared at her and I really noticed her body; her legs looked so soft. Then I noticed the way that she was lying caused her silk robe to ride up. I saw that she wasn't wearing panties. I got hard. I adjusted my hard cock, which caused me to move on the bed. She didn't stir. I tried shaking her a bit to wake her up, but she didn't move. I called her name and she didn't respond or stir. It was this time that I got bold. I reached the bottom of her silk robe and pulled it up to expose her nice, round ass. I stared at it for a minute then slowly moved my hand over her ass cheeks. As I did this, I wondered what I would tell her if she suddenly woke up. However, the more my hand rubbed her ass, the further my fears got away. I rubbed her ass while rubbing my cock through my pants.
By this time, my cock was bursting through my pants so I decided to throw caution to the wind. I got up from the bed; she didn't move. I went around the bed to where I could get a better look at her bare ass. I lifted her robe up further and spread her ass cheeks. I then took my phone out and took a few pictures of her. After this, I took the condom out, took my pants off, put the condom on my cock, and climbed on top of her, slowly. My heart was beating super fast at this time, but it was more out of excitement than nervousness.
I slowly slid my cock between her ass cheeks and grinded on her slowly. She didn't move or give any indication that she was awake. I continued grinding, but stopped to get my phone out to record my cock gliding between her ass. I stopped recording and kept grinding. I kept this up for a good four minutes, moving slowly because I didn't want to risk waking her up. I came a lot in the condom that I thought it was going to leak out. I had wanted to put my cock in her pussy, but I didn't want to press my luck. I climbed off of her and took the condom off, put my pants on, and flushed the condom down the toilet.
It was during this time that I realized what I had done; and how hot it was. I gathered myself together and looked at her still sleeping. I gave her a kiss on the cheek. I decided that I should leave so she could continue to sleep. I opened the door and it made a loud sound as it opened. I turned to look at her and she woke up. She looked around the room for me and she turned around and asked what I was doing. I told her I was leaving and she got up and said she would tell me to stay, but she was so tired. I told her it was okay. She gave me a hug and I left.
In the following days, I relived that moment through my memories, the pictures, and video. Sadly, I didn't keep the pictures and video because I had gotten into a relationship not long after and so I deleted them, without remembering to save them. I did see her one more time after that, but I always remember that night I had fun with her while she slept.
- That's Juicy! 14
- Remove It! 4
# 47971 - by Inferno_242 / November 8, 2020



