It’s never easy to discuss one’s embarrassing sex stories, especially when the whole world can get a preview. Some of them shouldn’t even be called sex stories because the embarrassment happened just before we were supposed to have sex. Construe it how you will, but here is the first one. More will follow in subsequent parts.
The Casino Lady
I was walking around a casino that I used to frequent on a Thursday and Sunday night when nothing else was going on. As I was walking in between the machines, looking for a target, I caught a glimpse of an Indian woman.
I walked down the aisle of the machines, turned at the end and walked towards her. During the conversation, she said, “We spoke about this when we met the first time.” I had approached her at the same casino months back and had a brief chat with her but forget about it.
Our date, the following night, went well and ended with a kiss and her legs wrapped around my groin. Not bad for a first day, but I wanted to stick it in, or so I thought.
She organised a hotel booking a few days later for us to seal the deal. I came down with flu two days before that day and only recovered a few hours before we met at the hotel.
We got inside the room, made out and decided to have sex after dinner. I couldn’t wait to finish dinner to get back to the room.
After dinner, she wanted to sit by the pool and admire the view. I sat for five minutes before losing my patience, then told her that we should go.
Inside the room, she helped me take her pants off because the button wouldn’t pop out, I was lying on the bed, and she was on her knees on the bed and sucking my dick while I fingered her from behind. She emitted five consecutive loan groans, which the guests in the nearby rooms must’ve heard. I couldn’t believe how loud it was and that it came from fingering.
For some reason, which became clear to me later, I couldn’t get a hard one. First, she asked, “What’s going on?”, then said, “I’m bored. I want to go home.” That made me lose even more strength in my dick.
Next, we tried at the nightstand in front of the mirror. She bent over, and I looked at her round, voluptuous ass and black hair cascading down her back, and I felt her soft skin. That made me get a boner, which fizzled as soon as I put the condom on. At that point, she had enough.
I had to save face. “I’m sick and didn’t want to tell you about it,” I said.
That was partially true, but it would’ve been a different story had it been a stunner.
She got on all fours on the bed, and I took off the condom. It was all or nothing. Her ass looked good, but I didn’t find anything else about her that attractive. It wasn’t the best time to find that out. I really needed to find a woman attractive overall to get a hard one. Her ass alone wasn’t enough.
Not one to give up, I grabbed her waist and thrust my hips forward, hoping that the motion and tapping my dick against her ass would get me hard. No such luck. “All I feel is drops on my ass,” she said.
Drips of my cum must’ve sprinkled her ass, though I wasn’t sure how since I wasn’t erect. Paranoia set in. The lack of confidence and embarrassment infused and made me think that the cum remnants were going to swim to her pussy and get her pregnant. Crazy, I know, right?
So now, I’m panicking. I start wiping her ass with my hand and cleaning up around her pussy while still thrusting my hips forward to give her hope of penetration.
“Is this a trial run?” she asked.
She was an expert at seeing a shattered ego on the floor and stomping on it until no pieces remained. Seeing that nothing was going to happen, she lay on her side and lifted her leg.
I had always been curious about anal and thought that sticking my dick in her tight hole would make me hard. I tapped my dick on her ass and slid it down to her ass. As my tip poked her ass, she asked, “Really?”
I lay behind her, saw her tighten her lips and look at me from the corner of her eye. She was disappointed and frustrated. I couldn’t blame her, and the only thing I could do was make it up to her.
We fell asleep and went our separate ways the following morning.
I thought I’d give it one more shot with her to make up for the lacklustre performance, so I went over to her place a few days later.
After giving her a foot massage on the couch, we went upstairs to her room.
I pulled off her denim shorts, looked at her tasty, thick thighs and got slightly aroused. She got on all fours on the bed, and I bit a chunk of her ass. Still loved her ass but wasn’t so crazy about the rest of her. She didn’t even want to use a condom, so it was all systems go. I tried to get it up but just couldn’t. I was zero for two.
There was no way I was leaving without busting a nut. She lay prone, and I sat on top of her and jerked off. I couldn’t even cum while jerking off and her naked underneath me, so I thought about a hot milf I had met a year before.
I busted on her back, then went to the bathroom to fetch toilet paper to wipe it off. “You can use the towel. It has to go into the wash anyway,” she said.
Paranoia struck again. She told me before that night that she wanted a kid, so I thought that if I wiped my cum with the towel that she would use the remnants and somehow wipe it on her pussy and get pregnant. Crazy, I know, right? There was no way I would take that chance.
“I’ll use toilet paper. It’s fine.”
The funny thing was that I spent the night there and left in the morning.