Jackpot! Desi


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I was in my very late thirties– 39 years old. I am an engineer, and at that point I had to travel for work often. I had recently retired from the military, and was now the low man on the totem pole at the company I worked for in Kansas City. I was the right man to go, though, and I loved to get away from the home office. This trip had me in Seattle for two weeks.

I had been chatting up a lady in Seattle. We had webcam at least once a week. She was a dirty redhead, blue eyes, and curvy in the right places. I had taken a chance and told her I would be in town, but she didn’t bite.

I was a little bummed out, but I understood. We did chat a bit, and she apologized, she wasn’t ready to meet. After a few days in Seattle, I was hanging out in the hotel lobby. I was waiting for some coworkers to come down, and we were going to go eat. After a few minutes of waiting, she walked in carrying a briefcase, wearing a navy jacket and skirt. She had a white blouse on and was wearing heels.

She was exquisite! Older than me, by probably a decade. There was no wedding ring in sight. She didn’t hide her gray. She had a head full of silver hair, neatly styled, and long defined legs. She had to be fifty, but she had it! Blue eyes, slim, and a bit of a chest that seemed to compliment her physique– B cups at best, but they fit her perfectly.

She headed for the bar in the hotel. I watched her walk by me. She glanced at me staring, but showed no signs of interest. I kept my distance. No doubt she would see me coming a mile away. I wrote her off, but I still took a good look. When my cohorts showed up– we left.

The next day the group from work was told we were having a social gathering at a local restaurant, Seven or something like that, they were on the water and the view was great, especially when the sun was setting. Well, I was at my mandatory fun, and across the restaurant was this platinum/grayhaired beauty with a full table. They were engrossed in something– all business attire. I gave her a look here and there, and got nothing in return.

We finished our fun time, and we all went our separate ways. I headed to a pub near the hotel. It was Tuesday and dead, until she walked in. She ponied up to the bar, and we gave each other a look and a smile. The empty place was a formula for success. She, the bartender, and I started talking. Her name was Beverly. We were a few in, and having fun. She was funny, engaging, and she had some piercing light blue eyes that she knew how to use– mesmerizing!

We walked back to the hotel, and we bid each other good night. I tore up my fleshlight thinking about those light blue eyes.

The next morning, I saw her at the hotel breakfast. We said a quick hello, and then after I sat, she plopped down across from me at the table. “May I join you?” She asked. I let out an “Absolutely!” We chatted over breakfast, talked about our work, and our lives as we had the night before. She was in a blouse and skirt and high heels. I said, I was looking forward to being done for the day, and she agreed that was her desire as well. I said I hadn’t been running in a couple of days, and I needed to hit the streets. She asked if she could tag along, and it was set. We’d meet after work in the lobby and go for a run.

That afternoon we met and hit the streets. She wore form fitting shorts and a tight athletic top. She looked fantastic. We ran a few miles, and then walked our way back to the hotel. I was having a great time. We stopped for a snack, and she asked what I was doing for dinner. I answered, “Whatever you’re doing!” She smiled, and we headed back for the hotel.

We parted ways, got cleaned up, and met again and hour later. She had picked another seafood restaurant on the water, but more informal than the previous night. She wore a skin tight dress that complimented her physique. She was bright and happy. We threw a few back, and this lowered our inhibitions. We ate, drank, and then walked for a bit. As we were walking, she took me by the hand, then wrapped her arm around mine. When we got back to the hotel, though, we went our separate ways.

The next morning at breakfast, she sat with me again, and got her laptop out. She texted someone and moments later, we were at a corner table chatting with a man Beverly’s age. She wanted to introduce me to her Beau. She wasn’t married, divorced for a decade– he called himself John. We exchanged pleasantries. They had been dating for almost a decade, but were “on and off”. They both laughed when they said it together. It was some kind of inside joke between them.

We wrapped up breakfast, and headed our separate ways. Beverly asked me to dinner later. I gladly accepted. “No plans, let’s find a place and enjoy.”

After work, I went for a run, then met her in the lobby about 6pm. She was in a sundress. She looked radiant! Those blue eyes were on full seduction mode. Her looks were deep, they bore into me, but in a desirable way along with her pretty smile.

We went in search of a place to eat, but ended up on the shoreline. We walked, talked, and she was wrapped around my arm, body against mine as we walked. I was being queued up– all the hints were there. I finally took an opportunity to face her at the sound, and wrap myself around her from behind. I leaned in and kissed her cheek as we stared at the afternoon sky. She snuggled into me, and she turned around, we wrapped our arms around each other tightly and began to kiss.

This went on for a few minutes. Gawkers, gawked. Then she began leading me down the shoreline. We came up on a little place, ate and had a couple, and then in the darkening evening, we went back to the shoreline.

There was a nice area to sit and enjoy what was left of the setting sun. The clouds were alight with some great oranges, reds and purple. She sat next to me, we were kissing here and there and talking. She spun herself over my lap and straddled me– the skirt of her dressed fanned over us. She was now looking me in the eyes, and explained what arrangement she had with her significant other. They both played, and were allowed to court and be romantic with other people (that was a polite way to say sleep with other people). She said they called it their “on and off” again relationship.

I immediately knew the inside joke. She kissed me, and we asked each other questions about it. She asked if I was alright with a casual relationship. I asked if she often engaged in casual play, and if she had regular play partners. She did, but she loved a new partner when she met the right person– she thought I would be a good fit. She liked my personality and physique.

I told her about my swinger/play activities, and there was a sparkle in her eyes and her voice. She hadn’t ventured into group , but had thought about it. I had been swinging with a couple for about 9 years at this point in my life. She was intrigued, but also glad I could have a good time, and be friends with them.

As we sat and talked, the kissing and conversation was getting more detailed and hot. My cock wasn’t at full mast, but it was growing. She could feel it, too. Her pussy was pressed against my crotch as she straddled me. She guided my hand under the skirt and rode my hand. Her pussy felt wet as she rubbed her lips over my hand and fingers. I was ecstatic that she didn’t have panties on under her dress. We stood up, and by this time my precum was flowing– I am a big cummer and I ooze precum like nobody’s business. There was a big wet spot on my shorts from precum. We had a good laugh, then proudly walked the shore back to the rental car.

We climbed in the back seat of the rental, and began making out. She quickly freed my cock that was now hard as a rock. She gripped my shaft tightly and stroked me. As my precum began to flow out of my tip as she stroked me, she murmured, “There it is.” She then lapped up the gob on my tip and the streamers running down my shaft and over her fingers.

She didn’t waste any time. She straddled me, pointed my cock at her pussy, and began sinking her hot snatch down on my cock. Her pussy opened up to me, got wetter, and she sank all the way down on my cock. She began grinding on me and as she bottomed out on me, with pleasure in her voice, whispered, “Jackpot.”

She rode me to orgasm, and as she came, her pussy gushed on my cock. I was soaking wet, and we moved easily in and out of each other. My balls were soaked, and she rode me fiercely trying to make me cum. We hadn’t started the car, so we got sweaty and soaked. She finally asked if I was going to cum, and I told her I wasn’t close. She asked, “Can we take this back to the hotel? So not only are you one cool cat with a big cock, but you have stamina, too?……. I am going to wear you out!”

She slid off of me, we kissed, then she hopped in the driver’s seat, fired up the car, and we headed back to the hotel. “Leave your cock out. I want to be able to see it while we drive back”. We smiled and she stroked me here and there as we made our way back to the hotel. Lots of precum was milked out of me on the drive, and when we got to the elevator at the hotel, she quickly cleaned my cock before we got to her room.

When we got to her room, we stripped and headed for the glass shower stall in the bathroom. We were all over each other. I bent her over the counter, and worked my cock back in her. I think she loved watching herself getting fucked in the mirror. We moved to the shower, and tried our best to lather each other up with the hotel soap. Lol.

She stroked and sucked my cock, and I explored her nipples and pussy with my tongue and mouth. When she wanted me in her again, she pulled my cock to her and slid me into her pussy. She had a long leg lifted and I easily slid into her. I brought her to orgasm again.

We killed the water, she toweled me off, and pleasured me with her mouth. She was a pro. She gave my tip the sucking of my life. My shaft was so hard a cat couldn’t scratch it. She cupped, mouthed and tugged on my sack and balls. She could even deep throat me. She was magnificent.

During my blowjob bliss, she stopped to “change” me. It was how she and her boyfriend measured cocks. Once she had me hard as a rock, she pulled out a change purse and laid quarters from my base to the end of my tip over the top– 8 quarters in all. She was happy with that “spare change”.

After she measured me, she went and hiked her ass on the edge of the desk in her room. She pointed at her pussy, and said, “Something is empty and lonely.”. I quickly caught up, positioned my tip and sank my cock back into her pussy. We got into a great rhythm, and kept it up till she came again.

At this point she said I needed to catch up. I hadn’t cum, yet, and she wanted me to cum like she was cumming. She wanted me to spew all over her, then she wanted me to cum inside her. I quickened my pace, and concentrated on the feeling of her pussy on my cock as I slid in and out of her. I brought myself to orgasm in minutes. I announced my orgasm, and she slid off the table to her knees and told me to cover her tits in cum.

I exploded on her Bcups, and spewed volley after volley on them. They were coated from top to bottom and side to side. She didn’t expect the size of the load. It coated her tits and was running down her body. She was looking at me and her cum covered body. She was ecstatic! (I love it when a woman loves cum!)

She smeared it all over her breasts and stomach. She rubbed my tip on her nipples. She licked her fingers clean. It was hot to watch!

We collapsed on the bed, and rested, enamoured with each other. She was quick to collect any juices that seeped out of my cock and coat her nipples with it. I, in kind did the same with her juices. We lapped each other clean with our tongues, and this got us going for another round. We got in a , and I enjoyed tasting her wellfucked pussy. I moved her so her breasts were in my face, and I made sure they were clean as well. She cleaned all her leftover juices off of my cock, and then we spun around and made out with our messy mouths.

She brought me to full mast, and then pounced on me. We were quick to find a rhythm, and then she planted herself on me, and asked if she could chat With John when we fucked. He would love to see it. I said, “Why not!” She got her laptop off the nightstand without sliding off my cock and connected with John in the chat app.

When he answered she was holding the camera so he would see her slowly riding my cock. He said “Hi Honey……. Whoa! That’s hot. Is that Jay?” She framed her face and said “yes”. Then she asked me to hold the laptop. She leaned back to give him a good view, and said, “John, he has a very thick twodollar cock!”. John was quiet, and then said, “Oh Baby, you look so hot with all that cock stretching you out and filling you……. 8 quarters! That’s a great cock. Jay, we need you as a neighbor!”

Then Beverly told him, “Jay swings with a married couple. They both fuck his friend’s wife at the same time. Imagine me with your dollarfifty cock and Jay’s 2 dollars stretching me out.”

John asked, “Are you ready for a threesome!” Beverly purred, “Yes, I think I am!” Then Beverly clamped down on my cock and blew through a hard orgasm. I could feel her pussy bucking hard on my cock. When she recovered, she said to John, “He also blew a huge load of cum on me, and he wasn’t shy about touching it or licking it up. You have some training to do when I get home!”

John was on cloud nine and excited! He whipped his cock out, and we both watched him cum almost immediately. We continued in various positions with John watching until she made me blow another huge load. This time deep inside her pussy she then rode my face to show John. After I ate her she had John watch us make out with my messy mouth. He came again watching us. They were both excited!

She hung up with him, and we rested, and went at it again. This time we chatted with my married friends, Rick and Lisa. We took turns performing oral and each other on cam for the others to see. It was a lot of fun!

The fun continued till the weekend when Beverly had to head home. We fucked for hours for the next couple of days. Work….. eat…… ! Jackpot! She left for home with two loads of cum in her pussy. It was a great trip to the west coast!

This Jackpot!