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Old Fun Regenerated Years Later

Well guys, have you ever seen that one women that made you fantasize and drool of what was under the clothes she was wearing and crave an opportunity to lick and kiss every inch of her velvety, silky skin body? When I met Jessica 25 years ago, I knew this gal was way out of my league. Jess was beautiful, confident and so damn desirable! I don’t know what Jess seen in me but somehow I won her over and within a year we were married. Jess and I (Jack) loved spending time in the bedroom, countertops, car and anywhere we could be together exploring each others bodies. We would sometimes have sex two and three times a day during our first year together. Jess was the sensual type of women that would melt in your mouth…. Literally..LOL The soft dental touch of Jess’s lips and hands would drive me absolutely crazy!

Jess knew exactly how to turn me on with her little innuendoes, body language and seductive appearance. I loved it when she would masturbate for me and then draw me in to lick her nectar. Damn she tasted so fucking good!

All was a perfect and within two years, motherhood was one of the greatest moments of our lives. Jess and I had a beautiful daughter and of course the care of our little one became priority and took a lot of Jess’s and my playtime. As most couples with children, life happens. All was great but in a different way. Family values and activities changed and we became responsible parents ultimately having less uninterrupted private time together.

We made it a point to go at least once a year to an adult resort to relax and reconnect with our intimate desires. We found this one resort that catered to open nudity and since Jess and I still had that free spirited frame of mind, we found excitement and a bit of risqué fun when there.

It wasn’t really a swingers resort but at times you could see couples enjoying themselves in semi private situations. While at this resort we were on the balcony of our room one afternoon and across the courtyard / pool area to an adjacent balcony. A couple were partially secluded and the female was engaging in oral sex with her man! Jess and I stood there on the balcony and briefly watch them. Jess said, look Jack, she’s giving him head right there where people can see! I said I see!! They were completely nude and just as we were gaulking at them, the guy looked over at Jess and I and waved his hand. Not to be rude or anything Jess and I waved back acknowledging we were watching them.

The female looked over at us and waved also with her free hand as she performed her oral skills. I was standing beside Jess watching them and I said it certainly looks like they’re enjoying themselves. Jess said yes it does! It was obvious he unloaded in her mouth and on her face as they finished. The female stood up looked back over at us, licked her fingers and waved at us. Jess and I couldn’t help but to smile and wave back again.

Jess and I went back into our room and said damn babe, did we just become voyeurs? Jess said I guess so and it made me horny! Jess reached out, grabbed my semi erect cock and said I’m not going to let them outdo us and dropped to her knees and began giving me a fantastic blowjob. Jess and I talked afterwards and said that was kind of hot watching them do that.

Jess and I showered up and got ready for a bite to eat at the resort bar & grill. This was a clothing only area. While having a cocktail and some chicken tenders, that same couple showed up and sat on the opposite side of the bar. They spotted us, waved and walked over to us and jokingly said, have we seen you guys somewhere before? We all laughed at the appropriate humor as Jess and I said I believe so with smirky smiles.

They introduced themselves as Chuck and Connie. They said they were from Ohio and come here once a year. We introduced ourselves also and found we had some things in common. They had two preteen boys that kept them busy at home and liked to get away from the everyday life to cut loose and be a little free spirited. Chuck said he wanted to apologize if they offended us by their actions earlier. Jess and I said no problem and we were kind of amazed with your carefree spirit. Connie spoke up and said she liked to take advantage of the fun as much as they can as this kind of recreation isn’t the norm back home with two rug rats constantly running around the house. Jess said dido to that!

After a little conversation Jess and I said our goodbyes and said it was nice meeting them and maybe run into them again while here. Jess and I went back to our room and agreed that Chuck and Connie were a nice couple and was impressed with their openness to interact in such a way that we could watch. I asked Jess how she would feel if she knew someone was watching us enjoying ourselves sexually? Jess said, oh my god I would freak out! But it does sound a little risqué and ornery. I said I never thought about it but the idea of someone watching you and I is a bit of a turn on. Jess said you bad boy, you're just horny and being ornery.

Jess and I discussed going out later to the resort club for another cocktail and maybe a little dancing. Jess was standing in front of the full length mirror brushing her hair when I walked over to look out to the balcony to look over the courtyard. Chuck was standing on his balcony and waved at me. Being this was a clothing optional resort, Jess and I spent much of our time nude when the opportunity was available and in our room almost always. With the angle of our rooms, we could pretty much see into each others rooms clearly when the curtain were fully open to the balcony’s.

I thought what the hell. I walked back inside up behind Jess and put my arms around her and began playing with her tits while she brushed her hair. I looked over and seen Chuck was still there casually looking our way. Jess still not noticing yet I pulled her a little closer and took one hand and rand my fingers around her mound. Jess leaned her head back on my shoulder and said don’t start something you can’t finish buster.

That’s when I slipped a finger in my wife’s pussy and to get her excited. I looked across the courtyard to Chuck and Connies room and I seen he had stepped back into his doorway and was playing with his dick. This was risky but I turned Jess ever so slightly so she was facing their room. Jess still had her head leaned back on my shoulder enjoying the attention I was giving her. I whispered in her ear that I think chuck our neighbor across the way was looking at us. Jess instinctively tried to step back and cover herself but I kind of held her firm so we were still visible. Jess said stop Jack, he’s watching us!

Jess still trying to cover herself the best she can and giggling a bit from my play. I said look babe, he’s playing with his dick watching us! Jess looked over and seen Chuck stroking his cock just inside his room. I whispered in her ear, he’s jacking off looking at your naked body! Jess said Oh God Jack! We shouldn’t do this! I said but look how hard you're making his cock! Jesus Jack, this is Crazy!

I could feel Jess’s pussy getting wetter knowing Chuck was watching me finger her. Jess was getting weak in the knees and I had to help hold her up. I was having fun instigating the situation. I said holy shit Jess…. You’re going to make him cum watching you Jess! She said Damn It Jack!!! As she climaxed on my hand!

I looked back over and Chuck had moved out of sight into their room. I was horny as shit now and I pulled our curtain closed and Jess and I fucked like two teenage kids on energy drinks! We laid there caressing each other giggling at our naughty behavior and agreed it was kind of fun doing something crazy like that and knew we would likely never see them again. We went back to that resort one more time and tried to be a little adventurous but the resort had changed ownership and the excitement wasn’t what it was.

Fast forward about 20 years, Jess and I deep into our careers and our daughter just finishing up college. Speaking of which she could be her mothers twin and it scares me to death as I can remember how I chased her mothers hot ass relentlessly. Jess and my wild and crazy times were way past us but we still enjoy or moments together. I still tease her on occasions that she could Mae another man cum in a heartbeat showing off that hot puss of hers. She would tease me back and said just maybe I will someday! LOL

Jess and our daughter were the best of friends and they hung out together doing many things. They loved to get dressed up and go to concerts together. Many people that didn’t know them took them for sisters they looked so much alike. Jess was a believer in taking care of herself and her appearance. Many of our daughters male friends called her a hot mom and behind my back called her a MILF.

Our daughter on occasions would bring her boyfriend and a couple of other couples over on weekends to grill out and hang out at our pool. Jess always catered to them making sure they all had a good time while visiting. One weekend a bunch of the kids were over and by this time they were of drinking age and I was sitting in our family room watching a ballgame while Jess catered to the kids. This one guy, I’ll call him Tom because he had a very unique name and if ever recognized one would know whom I’m referring to. Anyway, I caught Tom checking out my wife when she wasn’t paying attention or noticing. Especially when Jess was bent over and her lovely MILF ass was pleasingly in view. On occasions I seen Tom rubbing his crotch when nobody was looking.

I monitored his behavior for a while and could tell he had the hots for Jess’s sweet looking ass. I shrugged it off as normal young punk kid behavior as I did a lot of the same thing at that age. Tom was a good looking kid with blond curly hair and wasn’t with a girl or girlfriend? He seemed to be polite and offered to help Jess with anything while they were there. I assumed he just wanted to sniff around to see if he could get a better look at Jess.

I was proud of Jess being able to turn heads on young guys 20 plus years younger. I wondered how she would react knowing some young hunk was eyeballing her ass and rubbing his crotch?

Jess came back in to check on me and I said I was good but you better be careful bending over showing that hot ass of your infant of that blond haired kid! Jess looks at me funny like what are you talking about? I said I’ve been watching him checking you out whenever you’er out there conversing with the rest of the gang. I’m pretty sure I caught him rubbing his dick when you had your back to him.

Jess said don’t be silly Jack. That kids 20 some years younger than me and no way he’d be interested in someone my age anyway. I said don’t be surprised. These young guys like MILF’s and you certainly fit the bill with that hot ass of yours babe. Jess laughed and jokingly said wouldn’t that be the craziest thing you’d ever seen.

I said I’m serious. That kid has a hard on for your ass. I can prove if you’ll go back out there and bend over and work on the flower box beside the sliding glass doors. You’ll see his reflection in the glass and I’ll bet he watches you and plays with himself again. Jess looks at me like I’m crazy. I said come on babe, it would be fun to watch you turn on some young stud. She said ok I’ll prove you wrong. That kid Tom has zero interest in someone my age. Jess walks away and turns back with a grin on her face. The memories of when we used to get a little ornery came flooding back and I said make sure you bend over and give him a good view babe! About ten minutes later Jess came back out wearing a different pair of shorts that were slightly snug and would give a nice view of her back side and what was hiding underneath. Jess checked on the kids and went over to tend to the flowers. I was sitting where I could plainly see what was going on outside but you couldn’t see inside the house.

Jess started off by squatting down and tending to the flowers and I could tell Tom was glancing her way. Jess stood up and moved over a couple feet and this time just bent over with her legs straight with a good view of her ass. Tom immediately adjusted his chair around so the others couldn’t see him grab himself. Jess watch watching him play with himself in the reflection and even though see couldn’t see me through the glass, she smiled knowing I was right about this blond haired 20 something stud was playing with himself looking at her ass.

Tom even held his beer can over his crotch so others couldn’t see him playing with himself. Jess stood back up and turned towards the gang and said do you guys need anything? I’m going back in now. They all said they were good but Tom had a disappointed look on his face when Jess walked away.

Jess came back in and had this ornery smile on her face and I said, See I Told You!!! I said if that punk kid had a chance, he would have sit there and jacked off looking at that hot ass of yours! I said so how does that make you feel that some young stud thinks you're a MILF? Jess smiled at me and said well maybe I still have a little game left in this old girl. Jess walked over and kissed me. When she looked down she said Jesus Christ Tom, do you have a hard on!!! I had to laugh and said hell yea, I’m so proud of you babe and your still as hot looking as the day I met you! Jess reached down and squeezed my hard cock and said you’re being bad Jack. I said not as bad as you showing that young stud your ass and making his dick hard! She smacked me on the should and said stop it.

I said I wonder what he would do if he saw you naked? I bet he would jerk off and shoot his load clear across the room! Jess said stop it Tom! That ain’t happening and we’re getting too old for that kind of shit. I said by no means am I to old!! I’m just tickled that my wife can turn on a young stud with her hot ass!

I reached over and rubbed my hand between Jess’s legs and said Damn Babe! Feels like you’er getting a little damp down there yourself! Quit it Jack, I’m not wet, you”er just trying to start something. I can’t help babe. It just brings back some fun memories when you made that guy Chuck jack off watching us.

Jess said that was a long time ago and we don’t do that stuff anymore. I said so it wouldn’t turn you on to watch some 20 year old stud jack off watching you play with your pussy? Jess couldn’t believe I asked her that. As I was rubbing her pussy through her shorts she was definitely getting wet now and I called her out on it asking why she was so wet then?

Again she said stop it Jack, we can’t do this. Then she said (What if our daughter found out? I knew then she was contemplating the idea. I was so turn on of the idea I said I’ll figure out a way we can have some fun. Jess sat on my lap squeezing my cock with this crazy unsure look in her eyes. I stepped it up a notch and said I bet if he seen your wet pussy he would explode in 30 seconds or less. Jess said yea right.

I knew Jess was trying to imagine the scenario of a young hard dicked stud jacking off looking at her. I was also thinking of a way we could have some fun and was hatching out a risky plan. I told Jess to go change her panties because the ones she was wearing were soaked. She smacked me again and said damn you! LOL

I told Jess I think I have a plan. I was going to ask if one of the boys could come over tomorrow ad help me with a little project that I needed an extra strong hand with. If Tom said he would the plan would go into motion. If one of the other guys said they would come, I’d wait a while and say I forgot, that I had somewhere to be. If I was correct. Tom would gladly speak up and come over just for the opportunity to view Jess’s hot ass again.

Tom agreed to come over. I said I needed help changing out some light bulbs in our 18 foot vaulted ceilings and it was too dangerous for me to do by myself and I wasn’t sure Jess was capable of holding the large step ladder and pass the bulbs at the same time?

Tom came over around 1:00 and we cracked open a beer and chatted for a few minutes. Just a little guy talk and Jess came in with her run around the house outfit on. You know, those skimpy shorts that lets you see almost everything underneath and a old cut off t-shirt that barley covered her tits. I went and set up the ladder and Jess was talking to Tom thanking him for coming over to help me. She said those bulbs needed changed for a long time and she was too scared to help by herself. Tom said he was happy to help and just to ask anytime.

We all went to the great room and I climbed the ladder to the top and I asked Jess to come up half way so that Tom could hold the adder and pass stuff up and down to Jess. Jess went up about for steps and her crotch was right at toms eye level. I took out one of 12 bulbs and passed down to Jess. She had to go up one more step and it gave Tom a perfect view up Jess’s loose shorts with her pussy in plain view. Jess’s tits were also in full view when Tom was looking up. I know Jess had no panties on and Tom was getting an eye full.

Jess would stretch one leg out over Toms head each time she reached for a bulb. I spoke up and asked if everybody was ok? Jess said she was good and Tom could barely get any words out of his mouth! LOL

I was taking my good old time removing the old bulbs to get new ones. Jess kept looking up at me smiling and mouthed the words, oh my god and smiled again. She knew Tom was looking other pussy and tits. Each time Jess bent over to pass a bulb down to Tom she leaned over knowing full well Tom was starring other tits fully exposed. She said are you ok Tom? Tom said oh I’m just fine!

I looked down a couple times and seen Tom kept adjusting his shorts. Jess seen Tom adjusting his shorts also and she said I’m sorry Tom, I din’t mean to stand up here half dressed exposing myself like this. I thought you and Jack could handles this yourselves. Tom said oh no Mrs (….) Im fine and don’t mind at all. Jess smiled back at him and said are you sure as she pretended like she was hiding her tits a little bit. Toms face was beet red and he was sweating as he kept starring at Jess’s pussy and tits.

I spoke up laughing and said Damn Tom…. Are you starring at my wife’s tits and ass? With his beet red face he said…. Um…. A little bit sir, but I can’t help it! I jokingly said the old girl still looks good, doesn’t she? Tom just said Yes Sir. Jess reached down and rand her fingers through Toms hair and said thank you Tom you’er so polite. I spoke up and said polite hell it looks to me like he’s trying to rub one off standing there looking at you! Tom was speechless!

Jess looked back down at Tom and said. Tom…Are you being a bad boy looking up my shirt? Tom tried to gulp and just kept starring at Jess as she lifted her shirt intentionally to show Tom her tits. Jess said is this what you want to see? Tom could only shake his head in agreement. I said don’t do that babe. You’er going to cause Tom to get a hard on and cause me to fall off this damn ladder! Tom smiled, finally getting the idea we were tormenting him.

We finished up changing the bulbs and stepped back into the kitchen. Jess sat in a chair by the table as I grabbed us another beer. I said damn it’s warm in here and Jess said it sure is and pulled her t-shirt off and tossed it over to Tom and said it looks like you need work on something there Tom. I stepped behind Jess and played with her tits as Tom watched us. He had a raging hard on and couldn’t keep his hands off his cock.

Jess reached out with one of her bare feet and stroked across Toms crotch and said you better let that guy out before he rips your pants open! Jess pulled her shorts aside and started masturbating in front of Tom. That was the invitation for Tom to release the aching rod thumping in he is pants. Tom pulled out his nice size cock and was giving it long hard strokes right in from of Jess. Things happened much quicker than I wanted but Jess quickly removed her shorts and she had one of those little battery operated rabbit things and showed Tom her wet pussy as she used her little toy on herself.

I looked down and Jess was biting her lip as she watched Tom jack his rigid hard dick. I pulled Jess’s head back and kissed her. She was about to have an orgasm watching Tom only three feet away. Tom never said a word as his gut tightened up and he thrust his cock forward and shot hot cum all over Jess’s tits and belly! Jess still biting her lip as she had an orgasm when Tom shot his hot cum on her!

The moment quickly calmed down and I was impressed when Jess took her t-shirt and reached over and wiped Toms cock off. I said well it looks like we’re wrapped up for today. I said Tom thanks for coming by to help out. I assume you understand what we done is never to get out? Tom said of course. I said I knew you wanted to have some fun with my Jess when I filmed you with my phone yesterday while you were with the rest of the gang and rubbing your cock watching our daughters mom. I’ll keep that little video private too if you know what I mean. Jess said oh god Tom, don’t worry about Jack. He likes to have fun like the rest of us. Would you be interested in coming back over again sometime if we need help with another project? Tom said I’d be happy too anytime>

Jess and I aren’t what you would call swingers. This was the most bizarre ornery thing we’ve ever done. Jess said she got so horny watching Tom jack off and when he shot his cum on her, it drove her over the top knowing a young 20 something young stud wanted to cum on her. She asked if I was mad and I said of course not. We just had some good erotic voyeur fun.

After Tom left, Jess gave me a fantastic blow job and later we fucked like we did back in the day. I think we both have decided we need some erotic naughty fun in our lives again and Jess said let’s try some new stuff. She said she liked it when Tom came on her and wants to try it again. Maybe even a little touchy feely? LOL. Jess said she knows a girl that’s open minded and may want to have a little naughty fun with us sometime? I’m definitely up for that scenario!

We did invite Tom back over and things went much further than we had planned! I’ll write another story about it. Wow has our playtime ever changed for the better!