These stories are fictional. While the stories were inspired by real events, none of the characters are representations of real people. Any similarity to persons, either living or dead, is purely coincidental.

1. Jen

There are two big problems for an over fifty man who marries an under thirty woman.

First, you don’t want to act like “Mr. Know It All,” and second, you are always a little afraid your performance may not always be as good as it was when you actually were thirtyish.

I met Gail on line and we made an emotional connection immediately. The first visit went well because we never got out of bed the whole weekend. I talked her into getting married so I could put her kids on my health insurance. After about a year of the best and most frequent sex I’d ever had, Gail saw one of those thinly disguised news programs talking up all the positives about the swinging lifestyle.

Gail fell for the propaganda and told me she wanted to try it out. I had a little experience with swapping back in my past, so I wasn’t very enthusiastic. I didn’t want to come across as thinking I knew everything, so I reluctantly agreed to give it a try.

Gail found a party and we went one Saturday night, when we could get an all-night babysitter. It was mostly people my age or older, although some of the wives were ten or so years younger than their husbands. However, none of the ladies were up to the level of Gail, so I felt like the person who always brings good stuff to a pot luck where everyone else brings napkins and paper plates.

Gail threw herself into swinging enthusiastically. We sampled several groups and found one that was not doing dumb stuff like rolling dice to pick an activity and partner while getting carpet burns on someone’s living room floor. From the parties, we evolved into meeting one couple and doing either closed or open swaps.

One of our favorite couples, Tom and Jen, had just moved to our middle sized midwestern city from Las Vegas. Jen had been a high-class prostitute in Nevada before she got together with Tom and gave up, “The Life.”

Gail wasn’t beautiful like an actress or model, and her body wasn’t going to be photographed for men’s magazines, but she had a great attitude about sex, loved to fuck, and would never use sex as a bribe or a weapon. She’d had three kids, so it wasn’t like doing a teenager, but she was game for fantasies, and got really hot when I talked dirty to her during sex. She was a natural red head, and she’d shave her pussy any way I asked. I liked her to keep a nicely trimmed bush to show off her red hair and shave her labia so she could pretend to be younger in role plays. She wasn’t shy about asking me to fuck her when she was horny and she never complained if I woke her up to fuck in the middle of the night. We were able to do just about any position, and our bodies seemed to fit together really well.

Jen was not model pretty either. She had nondescript dark brown hair, but she was slim, tall, and had a bikini model body. She had a great attitude, and she knew how to talk to a guy and make sure his insecurities didn’t get in the way. She had a wide mouth and full lips that reminded me of Carly Simon’s pretty face. Watching my cock disappear between her lips and feeling her tongue do all kinds of wild things to me was a real treat. She was the first girl to deep throat me, and I don’t think anyone ever sucked me better.

As I said, we met at a party and agreed to meet at their house for sex. All four of us were naked in their king-sized bed. Tom was giving me the typical, “This is what she likes, and hates” speech. He was telling me Jen had a difficult time reaching orgasm, and to just do my best and not let her failing to cum bruise my ego.

Tom went after Gail fast, and they were soon in the middle of fucking each other’s brains out. Gail was multi-orgasmic and pretty loud. I worked on Jen slowly, enjoying getting to touch, caress, kiss, lick, and suck the hottest female body I’d ever had permission to play with. Her C Cup tits were very sensitive, and she seemed to get past being the bored hooker letting a man play with her body as I tried new ways of stimulating her breasts.

I like eating pussy. I like it a lot. I also enjoy helping women cum. I ate Jen until she came a couple of times. I noticed Tom was watching Jen pretty closely, and it seemed like there might be a greenish tinge to his face.

I didn’t know if Jen was using her hooker skills on me or if she meant it, but all of a sudden, Jen pulled my face up to hers, kissed me hard, and said, “I need that stiff dick in my pussy right now. Shove it in me as deep as it will go and fuck the shit out of me, old man.”

A woman is really putting herself at risk if she puts it out there that she needs you, so it’s only polite to give a girl what she says she needs, right? I figured we’d had plenty of foreplay already, so I went right to work on Jen, fucking her as hard and fast as I could, right from the start. I was glad she’d sucked me off when we first started messing around because coming quick is very likely to generate ridicule towards you at the party you miss. Of course, I was enjoying playing with Jen’s bikini contest worthy body, so I wanted her to think well of me in the hopes she’d want a repeat performance someday.

Now Gail’s tits were nice. Nursing three kids hadn’t wrecked them. They were D cup, cone shaped, full and solid, and very responsive. Jen’s body was definitely a wet bikini contest winner and wet dream inducer. Her hips were just the right amount bigger than her waist to make a guy’s cock hard just from looking at her. She shaved her pubic hair completely, and that made munching on her more delicious than usual. I liked being able to see my stiff shaft sinking into her. Since she’d never had a kid, her pussy was tighter than Gail’s so when my perverted fantasies started going wild, Jen made the sights and tightness match what my twisted imagination was doing to some imaginary teenage virgin.

After about five minutes of hard pounding, Jen groaned loudly and said, “That’s it, make me cum. Make me cum so good! Make me cum soooo hard!! Don’t ever stop fucking me, you dirty old man.”

I kept fucking her, but I slowed down a little so I could keep going as long as she wanted. I bent down and started sucking on her big, brown nipples, and Jen came again.

Now Gail came hard, and we’d fucked enough that I’m pretty sure I could recognize a real female orgasm when I saw one, so I was pretty sure I was doing something right for Jen.

Jen whimpered, “Do me harder!”

I did, and she came again. This time she was a lot louder than Gail at her loudest, and from my peripheral vision, I caught Tom watching us. His face didn’t look happy.

Tom and Jen were both mid-twenties adults, and I figured if he was jealous, it wasn’t my problem. I was “in the zone,” as they say, and I was going to fuck Jen the best I could, for as long as I could. My brain didn’t think about anything else but pounding her pussy, and I turned up my thrust speed and strength to maximum.

Jen started cumming with no pause between orgasms. She squeezed my dick with her cunt muscles, and finally I couldn’t resist her any more. I dumped a massive load into her convulsing, cumming pussy. Jen actually screamed when she came. Her eyes rolled back, and she passed out.

Tom moved Jen into his arms, so that he was the one holding her when she came back to consciousness, from wherever her mind had gone. There was no chance for us to whisper sweet nothings to each other or build any kind of romantic feelings for each other.

The next week, I got a job offer from a company on the East Coast, and we moved away. Sometimes I wonder if Tom and Jen stayed together.

2. Jean

One of the things most men worry about is whether their cock is big enough. A man has to be fairly confident about his size, or just not care, if he gets into swinging. Most women either don’t know how to reassure a male partner, or enjoy making their man feel insecure.

Our midwestern city was immersed in baseball at all levels. It was the home of the College World Series, and there were several minor league teams in the area. We met Matt and Jean at a party and got together at a hotel after the party to swap. Matt was a ball player. He had that stocky ball player physique. He played in the outfield, so he wasn’t fat. He and Jean were black, with very dark skin. He was twenty, and she was nineteen.

Jean had long, straight hair. She was a former volleyball player, six feet tall, with A Cup breasts, a tiny waist, and legs that went on forever.

The hotel room had two Queen size beds. I was trying to pay attention to Jean so she didn’t think I was ignoring her. I nearly missed it when Matt took off his pants and his cock popped out. It was as long and as thick as my forearm and the head was as big as my fist.

Matt sank his big salami into my wife’s pussy. He went very slowly, and Gail had a determined look on her face that said, “I AM going to get all of this monster in me.”

Jean whispered in my ear, “Don’t worry sugar. Size isn’t all a girl needs. Yours is normal size, and I’m sure you know how to use it to make a girl feel really, really good.”

I thanked her for the reassurance and asked if I could go down on her. She said, “I suppose. I had a girlfriend who did me back in high school, so I’m afraid whatever you do won’t measure up. If you still want to try though, I guess it would be OK.”

I’d run into girls before who thought only another woman could eat her pussy right. I just ignored their female superiority complexes now, and ate any girl who would let me, just because I liked the taste and feel of having my face buried between a girl’s legs.

I went to work on Jean’s thin, strong body with my fingers, lips, tongue, and everything I’d ever read about getting a girl off. Apparently, I’d read the right books and magazines. Jean started cumming, and before long, she wanted the world to know about it. I got her into a rhythm that let me keep her cumming over and over.

Jean pushed me away and said, “Whoever taught you did a pretty good job. You don’t suck as a pussy licker.” She laughed at her own joke.

She pulled my face up to hers and whispered, “You got me hot. I need you to fuck me now. I’m going to act like the world’s biggest slut when you fuck me. I’m going to cum a lot and get pussy juice all over you. It’s been too long since I fucked a man who has an average size cock and doesn’t make me feel like I’m giving birth or about to have my pussy ripped apart. I’m going to love it.”

I sank my prick into Jean’s cunt. Her labia were swollen and fat. She sucked my dick inside herself with her pussy muscles. I gave her a nice slow fuck, grinding my pubic bone against her clit on every stroke. Then, just like she warned me, Jean went crazy and started cumming. She was jerking under me and screaming loud enough to break my ear drums. I kept going as long as I could, then creamed her pussy.

Jean cuddled up to me and whispered, “I’ll give you my number. Any time you need a little extra and can get away, call me. You know how to make a girl feel good. You pay attention to all of me, including my too-small tits, so I feel like you want all of me.”

On the way home, I asked Gail if she had fun. She said, “It was more like earning a merit badge. I got all of it in me, but it wasn’t much fun. I kept feeling like I was having a baby and was about to poop all over the gurney.”

3. Jeannie

I didn’t feel like I was prime beef cake that got the females at the parties hot for me. I was bored most of the time because there was no one worth talking too, and all the best looking women were going after the few status symbol guys. Jeannie was in the same boat I was. She was only there so she could keep an eye on her philandering husband, keep him happy by allowing him his vanity, and making sure no silly romances developed. She was closer to my age, perhaps fortyish, while her husband was older and already completely dependent on Viagra to maintain satyr like performance. He went after Gail with a vengeance, leaving Jeannie and me as odd persons out. Finally, boredom overtook us and we started talking to each other.

We found out we were a lot alike, liked each other, and I was enough younger than her husband for Jeannie to be flattered that I was interested. We wound up fucking, and soon became regular buddies at parties. Jeannie had incredible B Cup tits that stuck straight out from her chest. She was petite in every sense of the word, so her B Cup breasts were quite dramatic on her small frame. Jeannie also had nice, smooth skin. She wasn’t at all old looking or wrinkly. She glowed in the full bloom of womanhood. I especially liked her completely bald pussy. The skin on her mound and especially her labia was silky smooth and never plagued by razor burn or stubble. Given my love of cunnilinguis, her satin smooth skin, light fragrance, and mild flavor made her one of my favorite girls to feast on. She came quickly and she came hard.