Went on a short Vegas trip with the hot nurse (she won’t let me use her name in these stories) and her friend Dusty. See previous stories.
The sex was hot and we had our first threesome there. After the second time we all fucked, we were headed down to the casino. We were kissing and playing when the elevator doors unexpectedly opened on the 15th floor and a woman in a tight, hot pink dress got on.
She immediately commented “Oh, I like where this elevator is going.” We all laughed and she said “Lucky guy with 2 hot girls with you.”
“It’s 3 now” I said.
The girl in the hot pink dress laughed. “How charming.”
Dusty whispered “Charming with a big cock.” The girls started giggling. We had been drinking earlier.
The doors opened and the woman in the pink dress looked back at me and smiled.
She was a thin brunette with what I suspected to be a man-made perfect tits to waist ratio.
An hour later after drinking and gambling, I take a piss and the woman in the pink dress walks up to me approaches me as I’m walking back out to the casino floor.
“Hey stud, where’s your two girls?”
“Right over there.”
“Will they care if you talk to me,” she asked.
“Maybe, but I don’t care. We’re all just friends… not together.”
Her name is Shelly. We played slots together and she told me that her husband was in a high stakes poker game all night. He gave her $1000 to gamble, but told her to play most of it on roulette and she better come back with a profit.
Shelly said “I have a different gambling idea… $1000 if you can make me cum 3 times. $1000 for me if you cum first. You can only use your cock… no mouth, no fingers. I pick the positions.”
I told her that she would just say she didn’t cum even if she did and she said it’s impossible not to know when I’m coming. Shelly said she’s multi-orgasmic and cums for over a minute and her body convulses and shuts down. She pulled up a video of her cumming with a wand.
We debated this for awhile until I finally agreed. She was hot and I wanted to fuck her but I really didn’t want to lose $1000.
I had just cum and she told me her first orgasm will probably be quick because she is craving big cock. Shelly heard what Dusty said in the elevator.
So I told the girls the proposition and they were mostly supportive but also skeptical of Shelly.
“You are taking us out to eat somewhere really nice tomorrow” Dusty said.
Shelly and I go to our room. We kiss passionately on the elevator. I feel up her skirt and remember the rule so I grab her ass and kiss her neck.
“You can rub my pussy in the elevator but that’s it” she said.
I feel her pussy through her panties and then push them to the side and feel her wet pussy.
“Oh fuck” she moaned.
We got to the room and she took off her dress as I got down to my boxer briefs. She was in a sheer, black bra and panties. She said my cock looked huge in my boxer briefs.
“I want to suck your cock so bad” she said.
She took off her bra and we kissed. She definitely had fake boobs. They looked amazing though. I complimented her repeatedly, knowing that she seemed into praise, which will make her cum faster.
She was on the edge of the bed when I pushed her panties to the side and entered her tight pussy. Fuck, I didn’t know her pussy would be this tight which might be a problem. After about only two or three minutes, she came really hard. She pushed me out of her while she lost control of herself from coming so hard.
“I told you the first one would be fast,” Shelley said.
She rolled over on her stomach and presented her little ass to me slightly in the air. I took off her panties and shoved my cock inside her.
We fucked doggy for around 5 minutes when I started to slow up. I still felt like I was in control though.
“Faster. Harder,” she said.
I fucked her and dirty talked my best lines while I spanked her ass and grabbed her tits. I had a disadvantage by not knowing her kinks but I figured out they were not pain. I could tell she was just tolerating spanking and hair pulling.
I started pounding her and she said she was going to cum. She collapsed into the bed, legs shaking.
She chose sitting up and legs in the air for the last position. Fuck. Why couldn’t she have picked cowgirl.
Her pussy was so tight like this and her tits were bouncing as I fucked her hard. I figured out her main kink was praise on her “hot, perfect tits” and “beautiful face.” She was moaning loudly now. I said “I’m going to cum so hard all over your perfect tits” as I pounded her and that was a trigger. She came for a third and final time. She didn’t seem too upset after now losing the bet. She just said “Guess I lost… fuck me how you want now.” She sucked my cock for a few minutes before I pounded her and came on her tits.
She gave me the money and headed out. “Bad luck at the roulette table, I guess” she said.
Source: reddit.com/r/gonewildstories/comments/127o2yi/1000_for_a_woman_to_cum_3_times_mf