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Ruby and Friends Ch. 01

By: MarriedFun



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.

Ruby and Friends Ch. 02



Chuck had stopped and was sitting there in appreciation of what he just saw, and then she looked over to Chuck. Unbuttoning her blouse, she exposed her black lace camisole with small but firm breasts with nipples obviously excited. Again she was a new kind of beautiful. Then she crawled on her knees, her skirt sliding up as she moved exposing more of her sexy stockings. 

When she got over to Chuck, his legs were spread and his cock was hard and twitching, aching to feel her lips. Ruby got close to him and brought her face to his, kissing his neck then his cheek then his mouth. I knew that he was about to experience something he will remember for a long time. While the two of them "became acquainted" I saw that Chuck had brought up a bottle of wine and 3 glasses. I poured 3 glasses, brought 2 of them over to Ruby and Chuck. They sipped the wine and Ruby was sure to leave her lips wet with the wine. Chuck bent over and licked the wetness from her lips and they kissed again, this time more intently and more movement. 

Like she did with me earlier, she then began to unbutton his shirt and kiss his smooth shaved chest. Spending more time on his nipples, they both seemed to enjoy that. While doing that, she had already removed his belt and unzipped his pants and slid them off as she licked his chest on the way down. She knew based on the earlier talk, that he might not be able to hold back since it had been so long for him so she just went right after him. Probably realizing there would be more and did not want to use all of his energy as she began to ache to feel his cock deep in her pussy. The size made her soaking wet with excitement. 

Her lips wrapped around his cock and she slowly moved her mouth down over his large shaft. I watched intently and could see her tongue slip out and lick his cock as she slowly slid her lips further down his dick. His head was back and he was feeling good. She pumped his pole into her mouth, holding her head with both hands tangled in her hair. She was really enjoying this new cock and she wanted to taste his cum so badly that she just let him pump and pump until he began to quiver and he moaned to her "oh damn baby, oh oh I have to cum... you want me to baby?" Not losing a beat she moaned approval. He expected her to pull off but no she buried his monster dick into her mouth as far as she could, he twitched a few more times then let out a loud grunt, followed by a few more as he unloaded his stock of cum that had been building for a while. She took it all, swallowing his massive load and while doing so, we both did notice that she had slid her hand down to her pussy and was playing with her clit and the juices flowing around it and she too could no longer hold back. With his dick throbbing in her mouth she moaned loudly as she came too. It was very intense for both of them. Both of them exploding at the same time, what a great sight it was. 

Ruby, after releasing his dick from her mouth, moved up to his mouth, kissed him softly and with a little of his cum still in her mouth, slid her tongue over his and shared his hot cum. Lips parting, they sighed together and he held her for a while, saying "Thank you, Ruby. That was incredible". Her reply was "Yes, yes it was and your cock is amazing!"

Chuck needed to regain himself, so he asked her if he could use her shower and she said "of course, please do, but hurry back we have more for you!" Ruth and I talked and decided that she was going to fuck Chuck while I played with her and that way my guilt would be less and could still maintain some little amount of dignity!

With the sounds of the water from the shower in the background, we both stood up, all I had left on was my briefs so I took them off, then reached around her waist, unzipped her skirt and slid it down over her stocking covered smooth legs and tossed it in the chair. She lifted up her camisole over her head and also tossed it on the chair, I knelt down, licked her belly as I removed her panties which were on top of the stockings so she could leave them on. That's Ruby, always prepared! She was stunning standing there in only her stockings and garter, bright shiny red lips and dangly earrings still shining in the dim light.

She took my hand as she laid it on the bed and spread her legs in front of me as if to say "lick me? Please?" Of course I could not wait and sat on my knees next to the bed and kissed her thighs starting just above the black stocking lace and moving up to her pussy. The last time I tasted this part of her was part of my first threesome and if he remembered correctly it was wonderful. She was trimmed neatly with a small V above her clit; the rest was smooth, very smooth. I very slowly ran my tongue over her clit and she gasped and grabbed my head with her left hand and with the right she grabbed the bedspread as she tensed up. As well as she knew how to suck a cock, I knew how to lick a pussy. My tongue and finger took turns entering her vagina. Then I inserted 2 fingers cupping then up to get her g-spot and she was writhing on the bed as she almost growled and cried with pleasure, she too was about to cum again and I was not going to hold her back. Her back arched as she went quiet, I could feel her warm juices begin to flow and her cunt grabbed my fingers with each thrust of her hip off of the bed. This woman really knew how to enjoy an orgasm. "Oh my, oh yes, yes YES" she cried loudly with pleasure. 

She twitched a few times as her body came down from the thrill, and she firmly pulled me down to kiss her with passion. "We still got it" I said and she simply smiled and nodded her head in agreement. Chucked finished his glass of wine, offered us some and layed down on the bed with a towel around his waist. Ruby asked him to lose the towel, she had plans for that big cock. With that she climbed between his legs and took his limp and clean dick in to her mouth. It was not long and he was rock had and massive again. His head flat on the bed, she straddled him and was rubbing her dripping pussy over his dick as she kissed him. Then she sat up, facing away from him positioned her pussy over his rod and slid it down to engulf his cock slowly. She closed her eyes at first then opened them and looking at me and I could just read her mind. She had to be thinking this cock is so big, must be 10" and every inch was sliding into her cunt. With each stroke the bed bounced and I had the view of her riding his cock with her perky tits moving in rhythm with their pumping.

They were grinding and fucking was so very very hot to watch. Like a real life porno for me, my dick with my hand around it began to quickly grow. Their movement slowed and became easy and smooth as Ruby looked at me, gave me the come over here finger wave. Instantly I know what she wanted, she wanted me to stand on the bed in front of her facing them, basically between his feet and she wanted to suck my dick again. She took it in and their movements were perfect, she let me fuck her mouth with the motion of his cock gliding and pushing in to her dripping pussy. His moans got louder and lower in tone and I was thinking he will now be filling her cunt with his hot cum. She was pretty much coming back to back it seemed after she had my cock in her throat. I was close too, this session was too hard and too good to hold it back. Then he grabbed her hips, stopped his pumping as he blasted his cum up into her pussy. The sound of them cumming put me over the top and I pulled out, and unloaded all of my cum on Ruby's neck and chest. Damn, I am not sure I have ever cum that much at one time. When I got off of the bed, they were still joined and I could see his cock with their juices dripping out of her drenched pussy. 

She rolled over on the bed on to her back, then one of the sexiest things I have ever seen happened. It surprises me that I enjoyed it that much but it was incredible. Chuck began to slowly lick my cum off of her tits and neck. He would get some in his mouth, and then take it up to her lips and they would kiss. Their lips wet with my cum. It so different and surprising and it was beautiful too. 

We all showered, laughed, dressed and began to plan our next business trip... but not until after I would have my chat with Lorie.