Ruby and Friends Ch. 01

As we get closer to 50, Lorie and I are trying ways to keep the sex fresh and interesting. Both have had many fantasies like soft swinging where there is another couple involved, but only light touching between the pairs but sex only with your partner. Also we have fantasized about having sex with another partner, as long as it was confessed right after. These stayed as just fantasies until a few months ago.

When I came back from a business trip out of town last week and told her that I had something to tell Laurie, right away that night while in bed. I was curious but not concerned since we love each other so much and have a very strong relationship. I told Lorie me the story of the 2nd night of his trip, at dinner and later that evening. My business partner Chuck and I were at Dinner when we ran into an old friend of mine, a lovely woman named Ruby. We have been friends for years.

At dinner, the woman at the next table caught my eye and soon I wondered if it was Ruby, his longtime friend from years ago? Having not seen her for over a year, my memories of her before Lorie and I met, flooded in my mind, from the incredible blow job she gave me at work, to my first threesome to her humor and boldness as she was never one to hold back anything. He had to ask, and yep it was her. She was by herself also on a business trip, leaving tomorrow. A few minutes later she had joined them and both could not help but notice this stunning woman with nylons in silky dark brown, black skirt just above the knee and glossy high heels with a smooth white blouse with buttons fastened just above the cleavage. Her hair was shoulder length and wavy, shiny and brown. The gloss of her shoes was matched by her perfectly puffy lips covered in cherry red lipstick.

Seeing her lips, he thought back to that glorious bj she had given him years back. He never forgot her oral skills and he remembered her mouth feeling better than any pussy his cock had ever been in. And her love of swallowing cum as she would move her mouth in with his dick deep in her throat as he shot his warm load in her throat, preventing her from gagging on his shaft and cum. After remembering that night, his cock twitched in his slacks and wondered to himself... maybe...

Anyway, Chuck and Ruby made small talk while Jack sat back and observed and soaked in her sensuality. She was never one to not talk about sex, it was still her favorite topic. And before you know it, I saw that look in her eye as she chatted with Chuck. I could tell that she would have Chuck's dick in her mouth tonight. Now all I needed to figure out was how to be a part of that. My arrangement with Lorie had been an open one. Either could have sex with someone as long as they admit it and talks about it right away. But it had not been tested, but it was about to.

After dinner and a few drinks, the three of them had so much in common, they were like old friends. Chuck was 32 and had been divorced for 3 years, not dated much so I can only imagine what was going through his mind. I picked up the check, and Ruby threw it out there. She said "why don't you boys come over to my hotel for more drinks and talk?" Obviously neither of us was going to say no to the invite so we made plans to get over there about an hour later.

Her hotel had a bar in the lobby which was convenient, so we looked around a bit and back in a corner was Ruby. She was still wearing her incredibly sexy outfit. It was a round booth so we picked a side and slid in next to her. The scent of her fresh perfume was incredible and she just smiled and said "Welcome boys". Again after some brief small talk of current topics, the chat was somehow moving towards the last sex that Chuck had and what a disaster it was. Lucky it was him and not me. Ruby felt bad for him and mentioned that maybe we could help? She sensed that Chuck was a little shy and having me go along might be less intimidating for him perhaps. Within an hour Lorie and I were heading up to her room while Chuck took care of the check and made a phone call.

As soon as her room door was shut, she turned me around against the door, pressed her body in to mine and kissed me with one of the most sensuous and soft kisses that I had ever felt. My dick slowly stiffened and she could feel it grow between us, pressing into her. She looked at me and smiled as she ran her hand down from my chest to the slacks over my cock. She knew of the agreement between Lorie and I and she asked, "Are you sure about this?" I answered with "yes, I am".

She took my hand and led me to the bed facing away from the door, sat me down on the edge and kneeled on the floor in front of me. Slowly she unbuttoned my shirt from the top, kissing my chest on the way. Spreading my shirt she started on the belt and pants. My cock was pushing my briefs up as she slowly pulled them down exposing the tip. In one quick move she pulled my underwear down and fully took my cock into her mouth going all the way down. I almost exploded into her right then, but she was a master. She knew exactly how to control a man with a rock hard cock in her throat.

She ran her tongue around my shaft while gliding up and down. The vision of her glossy red lips surrounding my dick was incredible. Her skirt still on sliding up her legs as she knelt. I could barely make out the lace at the top of her stockings, I had not been that turned on in years. I enjoyed sex but not with this intensity. I was struggling to hold back and she knew it. She kept pushing me to the edge and slowing, probably sensing and tasting my cum as it seeped out. I closed my eyes, rolled my head around and to my surprise, sitting on the chair in the corner of the room was Chuck, he had his cock out and was watching her give me this incredible blow job as he stroked his dick. I could see that his cock was much bigger than my average dick and I thought, "This might be fun to watch later".

Ruby ran her fingernails up my thigh and wrapped her hands around my dick as it was juicy and wet from my pre cum and her saliva. Sounds of slurping and sliding and her moans pushed me over the edge that even she could not stop. She felt me cumming, and a few seconds later the first shot went deep in her throat, but she knew men and she knew that Chuck would like to see cum all over her. She pulled my dick out of her mouth before the next few shots shot cum all over her lips, chin and a few drops on her blouse. Then I did something that I have never done before but I bent over, kissed her beautiful lips and licked some of my cum from her lips, tasted it slightly and then kissed her with my tongue and she sucked the cum off of my tongue. It was an incredible experience. We knew then, it was Chucks turn to cum.