My wife was 55 when this adventure took place. First let say, my wife, Jill, not her real name, is very gifted at keeping her youth, even to date young men and women are floored when she discloses her age, she literally must proof how old she is. Part of her ritual is a daily visit to the fitness club.
We vacationed at a Texas coastal town and while we were out of town. We occasionally talked about her having sex with other men, her answer was routinely, no, this time I asked a bit differently. I told my her, we are out of town, there is not a chance that anyone will know, unless you or I reveal anything. So, would you have sex with a young man. She laughed saying, no young man would have sex with an older woman like me, but I noticed she also didn't say, NO. I know Jill is wrong, because when I was very young guy, I like many young men, took advantage of many opportunities that came my way and had sex with older single and married women. I work with many young men, I hear them talking amongst themselves and some have even confided in me, they like to have sex with older women because they know how to fuck, really good, they claim, cougars are great time in bed.
I felt the time and place were right to make a fantasy real, so I told her, if I get you a young guy will you have sex with him, Jill looked at me with an unsure look.
Without her knowledge earlier in the day, I had contacted a 23-year old local guy through a popular dating website. Slightly blurring out her face, I encourage Jill to dress more provocatively in public. I had some pictures of my wife in very sexy poses dressed in lingerie and heels, asking him would you like to fuck this mature hot wife? The young guy, I will call Danny immediately jumped at the chance, saying I will come over now, I knew I had him hooked, we are not immediately ready, send me a face photo, he responded immediately with my request. Danny was a very good looking young man, I told him, if you come over and you are not the guy in the picture, everything’s off, he agreed. I sent my phone messages to my laptop email. Danny sent two photos, a fully clothed full photo of himself and a close-up of his face.
I faced Jill and said, you never answered my question, will you have with a young man if I get one. She said, sure, why not, no one will know, I am not telling, but it will never happen. No young man will have an older woman like me. I responded, you really believe that, don’t you? I know you think I am saying this with a bias, I see you as hot sexy woman that any young American guy would love to fuck. Since you already said, yes, come here and let me show you the young guy that is coming over her to fuck you. I opened the email and showed her Danny’s photo and she said, WOW, HE IS CUTE! I showed her the emails and photos where he stated he wanted a chance to get at her hot body. After reading all the emails, she said, HELL YEAH! She was suddenly very excited saying, I really didn’t bring any sexy short skirts, I said, so that is going to stop you.
Jill started browsing the internet for the stores she liked to shop at and found them. It was 3:30 PM and I told her, he wants to know what time he should come over, she said 7:00 PM, we should be done by then. I text him and said we had errands to run and we would meet him in the lobby of our hotel at 7:00 PM. I know you probably were not expecting sooner, it cannot be helped sometimes, he replied for a chance to get between your woman’s gorgeous legs, I will wait. I showed his response to my wife, and again she said, "WOW, I was scared, but I’m like a young girl, now I want him to fuck me hard."
We went shopping and she bought a very short skirt, sheer black panties, high heels, a very low-cut top, and sheer nude stockings. We got from shopping and she showered while I set up my video equipment, I was not going to pass up a chance to record this adventure. My wife finally came out of the bathroom and she looked like a total fucking HOT WIFE! I got her to raise her skirt, do a sexy pose and I snapped some pictures. I grabbed her pussy and her panty crotch was already wet, I said, well you have no regrets. She replied, regrets? I am looking forward to this young guy to fuck the shit out of me, not too many women my age, get, a present like this. It was 7:00 PM and we headed to the lobby.
We were on the elevator going down, I looked at my hot looking wife and fought urges to fuck her right there, luckily the elevator door opened. We walked around the corner and we recognized Danny by the photo he sent earlier. I said, you are Danny, you match your photo. Danny looked at Jill and his eyeballs almost popping out of their sockets. I said, if you want to continue our meeting, join us in our room. We got into the elevator and the door closed. I did not plan this, but the event happened this way. My wife was standing to my right and one step closer to the elevator door. Danny was standing almost directly to my right staring at my wife’s ass. As soon as the elevator door closed, I quickly broke the ice, I immediately reached my wife’s skirt and raised it, Danny stared at my wife’s firm ass. I spread her legs and pulled her back by her pussy into Danny’s awaiting arms. Danny was kind of nervous, so I signaled him to put his hand on her crotch. My wife skirt was still raised as she leaned back on Danny. Danny started to finger my wife in the elevator and her breathing was getting heavier. The elevator was about to open so we all stopped and when saw that no one was there, we started walking down the hallway, I was behind them and Danny had her skirt raised and as his moved his hand under her panties massaging her bare ass cheeks, I could tell she was getting off with Danny.
We got to our room, Danny sat down on the couch, exchanged some pleasantries while having a drink. Jill turned to me and asked what do you want me to do before I let Danny fuck me? I know Jill loves to suck cock, so I replied, give our friend a blow job, if Danny doesn’t mind, Danny quickly said, I don’t mind. Jill threw a pillow on the floor and dropped on her knees, unzipped him and started jacking off his cock. Danny started to get hard, she started inserted his cock in her mouth, before long, she was breathing real hard was making sexual moans, ooh, ooh, ah as she frantically started going up and down on Danny’s cock. Danny now had a raging hard on, about a 9-inch cock, not a beer can in diameter, but still a respectable thickness. It was getting late, but the sun was still setting. I told Danny, we are on the 14th floor, take Jill out on the balcony and fuck her. Danny said, HELL YEAH, THAT WILL BE FUCKING HOT.
I got my video equipment and started recording all the action. Danny bent Jill over against the balcony wall and had her hold the top of the wall. When she was in position, he raised her skirt up her waist. We could see that Jill’s panties were very wet. Danny moved her panty crotch to the side and started inserting his cock in her pussy, Jill moaned, ooh, she was already so hot, Danny did not have a problem sinking all his 9-inch cock all the way until his balls were flushed against her ass. Jill said, damn that feels so fucking good, then she said out loud, FUCK ME GOOD, COME ON FUCK ME. Danny started ramming her pussy hard, his balls slapping against ass, SLAP, SLAP, SLAP, SLAP, Jill was going crazy saying out loud, FUCK ME, FUCK MY MARRIED PUSSY HARD. He fucked Jill, on the balcony for another outside for about 20 minutes, Jill was coming all over his cock, he finally said, I’m coming, I saw Danny tense up and he started dumping all his cum deep in her pussy, Jill was grinding backwards on his cock. Danny was a virile young guy and had lots of cum to dump, he kept coming until his balls were drained in her pussy. Danny told Jill, lady, you have great pussy. I have fucked a lot of girls, but you are the best pussy I have ever fucked, no lie, boy can you fuck. I remarked, see what I mean Jill, young man like to fuck mature pussy, because cougars know how to fuck. Danny said, HELL YEAH! I have a hot looking grandmother, I would fuck her if I could. I said, good luck and laughed.
We sat down and had some drinks. Jill sat beside me on the bed, Danny was on the couch in boxers, about 15 later Jill went over and sat by Danny and reached to his crotch and took out his cock and she started sucking it and she looked at him and said, I want more of this and started sucking his cock again wildly. Jill finally got his cock very hard, he had Jill lay on the bed and open her mouth wide and he inserted his cock and started fucking her mouth. Jill started breathing very heavy and it was very rapid, it was obvious Jill was enjoying her mouth being fucked by Danny. He was now fucking her mouth in a very rapid pace, and I told him, come on Danny fuck that mouth deep, come down her throat, fill that mouth full of cum. Danny started tensing up and started draining his balls in her mouth, he was coming so much, she had cum rolling out of the corners of her mouth. Jill finally finished swallowing all his cum and started licking his cock and balls until they had no cum left on them. Danny told me, man, you’re so lucky, you have woman that is a great fuck and is a fantastic cock sucker and I can tell she loves to have her mouth fucked, he looked at her and said you like your mouth fucked, don’t you? Jill said, hell yes, that was hot!
We sat down for some more drinks and it was getting late. About twenty minutes later, I was surprised when Jill walked over to Danny, stood right in front of his face, she raised her skirt, and said, do young men know how to eat pussy? He rolled her panties down to the floor and started licking her pussy, she started bucking her hips at his mouth, this is so fucking hot. Danny started fingering her pussy with two fingers and Jill was bucking her hips hard against his fingers, he removed his fingers and started darting his tongue in her pussy. I was recording all the action, so I moved to record a better view and Danny got up and started French kissing her, he unbutton her skirt and it dropped to the floor. Danny continued unbuttoning her top and he removed it and handed to me, she had no bra, Jill’s breasts were free. Danny immediately started licking, kissing and sucking her pink areolas, Jill was pushing her breasts hard against Danny’s mouth, while he sucked on them hard, this young guy was driving her wild.
Danny sat her on the bed, spread her legs, started eating her pussy hard. Jill started breathing very hard, moving her head from side to side, also rolling her eyes backwards, she was in a status of sexual bliss. I thought to myself, is this the same woman that thought no young man would want to have sex with an older woman, look at her now. Danny got her pussy so wet, there was no resistance when he started driving his cock in her pussy, he was in all the way with his balls against her ass, SLAP, SLAP, SLAP, SLAP. He put her legs on the bed and picked her up by her hips and he started pulling her by her hips against his cock. About five minutes later he stopped, and Jill said, don’t stop and she started bucking her hips upwards hard to take as much cock in her pussy as she could. As I chuckled, I said, you like that young cock? She was bucking her hips wildly hard against Danny’s cock saying your cock feels so fucking good. She responded, this young cock is so fucking good.
Danny withdrew and positioned Jill in a doggy style position and slipped his cock right in all the way and started thrusting in and out fast and hard, SLAP, SLAP, SLAP, SLAP, Jill started screaming, HARDER, FUCK ME HARDER, he continued for another five minutes and he withdrew again and laid on the bed and got her to start riding him. Jill was so wet she sat on his cock and it went all the way in without any restrictions. Jill started bucking her hips fast and hard on against his cock for about five minutes, then she started going up and down, she slapped her body against Danny’s, when they met, SLAP, SLAP, SLAP, SLAP, SLPA, I thought look at her go. She alternated between bucking her hips and bouncing up and down on Danny for about 20 minutes, then Danny said, I’m coming and he started shooting all his cum up her pussy, Jill started grinding her down hard on his cock, saying, I love it when a guy explodes in my pussy, I love to feels cum deep in my pussy, give it all to me.
Danny withdrew and said he had to leave, it was getting to late for him as he had to drive about 35 miles away and had to be at work in the morning, he said he had a great time and Jill said the same thing, he said, if you are in my area again, contact me, I would like another run at that pussy. Jill said, she sure would keep that in mind and he left.
After Danny left, I asked Jill, what did you think of your adventure? She said, she couldn’t believe she was doing this but once it was happening, she felt so naughty and hot fucking another guy in front of me, but she loved it. I asked, do you want to do it again? This time without hesitation she said, HELL YEAH, THAT WAS A LOT OF FUN! I said, we can have more adventures anytime you want to fuck another guy, you can pick him out. Jill replied, No, you have good taste, I will fuck anybody you want me to fuck, just make sure they men are safe, and the meetings are discreet, it would ruin at work.
I pulled her to the edge of the bed, spread her legs wide, held them straight up and said, I see Danny’s cum is still running out, I’ll push Danny’s cum back in your pussy, I quickly inserted my cock, her pussy was so wet and full of Danny’s cum. I had no resistance driving my cock all the way in until my balls slapped her ass and started slowly fucking and talking to her. I said, I always wanted to feel another man’s cum in your pussy, it’s an incredible feeling. Jill replied, I got so hot Danny fucking me in front of you, I did not realize it, but I it makes me so hot to have your cock in my pussy after another man has fucked me. It was such an incredible feeling fucking my wife after another man had just dumped his cum, her well used pussy was driving me into a very hot and excited state, I began fucking her hard like a wild man, Jill was also on fire screaming, AAAAAAAAH, AAAAAAAAH we fucked until we finally went sleep.
After that night, I made sure Jill had plenty of discreet meetings. One weekend out of town trip, Friday-Sunday afternoon, she had four discrete meetings with four different men, but those are other stories.