A no strings meeting with a stranger
A few years ago I placed an ad looking for someone to play around with. I had indicated that I had never cum on a woman before and also didn't have much experience. A woman answered and said she was looking for a similar type of thing, and after emailing back and forth all day she asked if I wanted to meet. The one stipulation was that her husband had to come with her. I didn't really care- if it meant I got to mess around with a woman then do whatever you need to do.
We set up a time to meet at a bar in between the towns we lived in, and if she was fine with things we would then move to a nearby hotel. I was nervous as hell, but arrived 15 minutes before they did. Just when I thought I was being stood up, a gorgeous blonde woman and a nice looking guy entered the bar. I literally said "holy shit" out loud when I saw her. She looked around the room and our eyes met. She smiled and mouthed "is that you?" I nodded, and they came to join me at the table.
Jenny (not her real name) introduced herself and her husband, then they took off their jackets to sit down. I quickly sized her up in the moment. About 5'4", 125 pounds, and size 36D tits (found that out later), and a little older than me. Jenny was a delightful woman and we got along immediately. It was like we were old friends. As soon as her husband got up to use the restroom, I leaned over and whispered "you are gorgeous!" in her ear. She smiled and called me sweet. We talked some more, then Jenny said "are you ready?"
We left, and I followed them. Once we got to the hotel, I walked in behind them. Jenny had an amazing ass, and all I could think of was "is this really happening?" We got to the room and made a little small talk, then Jenny turned to me and said "ok, you need to get naked." I quickly took off everything but my underwear, and then I asked her to pull them down. I loved watching her face as my cock bounced from my underwear. Now it was her turn. "You do it for me," she said.
So I pulled her sweater up over her head and handed it to her husband. Next, I took off her high heeled shoes and set them aside. From the front I unbuttoned her jeans and slid them down and off. "Now my bra," Jenny said. I unhooked them and she turned to face me. She had amazing tits and I blurted out a "wow!" That made her smile, too. The next to go was her thong underwear, and I finally got to lay my eyes on her nice and shaved pussy. This woman could easily pass for someone in their 20's.
I playfully swatted her butt as she passed me to crawl on the bed, and we both laughed. She patted the bed and told us to join her. Her husband was naked, too, and it was a bit weird being naked and hard with another man who was naked and hard. She was sitting with her back to the headboard, and we crawled up and either side of her. She took my dick in her hand and slowly started to stroke me. What came next is a quote I will never forget.
"You are huge! That is the biggest cock I have ever seen! Sorry honey!" I said something about yeah, right, and she said she had never seen anyone that big. Her husband was about 5" and skinny, so it could be true in her case. He just looked at her, then me, and then himself and just shrugged. A funny moment. We had agreed to no touching, but the next thing I know my cock has found its way into her mouth. I asked him if he was ok with that, and he just nodded. Like I'd ever pass up a blow job! She did that while I played with her tits, then I moved down to focus on her chest. He was on the other side sucking the other one, and she was having a blast.
Soon she proudly said something about being a lucky woman to have two men pleasing her. "Do you want to lick it?" she asked. I checked again for permission, and went to work. She was a great teacher and had me doing all the right things, and I actually gave her an orgasm. I started by rubbing her lips and inserting my finger for lubrication, and slowly rubbed circles around her very sensitive clit. Direct contact made her jump, so she wanted that saved for last.
I slid two fingers into her and rubbed her g spot until she trembled and pushed up against me grinding her clit into my tongue. The best part is that she is a squirter. I had only read about such a thing, so it was amazing to feel it on my face and see it in person. She was back to stroking me again while her husband was stimulating her with a vibrator and I was playing with her tits.
Not long after that she announced that she wanted me to straddle her and cum on her tit. This was an incredible thing for me to be jerking off just a few inches from her face and those blue eyes staring up at me. I shuddered and came all over her tit as she reached another one of her five orgasms. "Do you want to watch us?" Hell yes. He climbed on top of her, and I slid down to her waist. I watched from a few inches away as he entered her. I won't violate the no sex rule of ST, so after they were done I was ready to go again.
She had never been titty fucked so she wanted to take advantage of playing with a longer dick. We did that for a little while, and it was a little difficult without any lube, but I wasn't going to say anything. I held her nipples as she watched my dick slide between her tits, and then she told me to finish again.
Not moving off of her, I started to jerk off while straddling her and staring at her face and chest. It was too much for me, and I shot my cum right between her tits. Jenny moaned and I climbed off of her.
It was there room, so I got dressed and was ready to go. Jenny gave me a nice hug and a kiss on the cheek, and I walked down the hallway wondering how the heck that just happened. I wish I could say it turned in to something, but that was the last I saw of her. If she ever read this I would say this: you have my number, so text me.