Country Club Fun

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Donna had another party a month or so later and things went pretty much the same as the first except I took a few more frequent 'rests' to give some of the ladies a good time with my tongue. About an hour earlier, I'd enjoyed giving one of the women from the first party a repeat pussy licking, I think her name was Wendy. After she'd came, she gave my cock a good grope and looked quite pleasantly surprised at what she was feeling. "Damn, that's a pretty big cock you've got there. Maybe I'll have to try it out sometime."

I was making the rounds a bit later to see if anyone wanted another drink and one woman pulled me over to her little group of three. "Maybe you can help us settle a bet."

I said "Sure, what's the bet?"

My guess would have been something about cumming from oral, tastiest pussy or something similar so I was a bit surprised when the one that had pulled me over said, "I'm Carol, this is Deb and you've already met Wendy. Let's face it, all three of us have sucked a guy's cock before but obviously some are bigger than others and Wendy here said that you've not only got a great tongue but you're pretty damn well hung. We want to see who can take the most of you into their mouth."

Go figure, I was more than fine to help out and soon the four of us found a more or less private corner of the yard that was fairly dark. As one of them pulled my shorts down, all three of them mumbled a quick, "Wow!" when my cock popped clear.

I wasn't fully hard yet but a little stroking from Wendy did the trick and she went first. It took her a little bit of work and a little gagging before she quit at just over the half way mark. "I've always had a bit of a gag reflex but I do like to swallow" she said with a grin.

Then Carol gave it a try and stopped a bit further than Wendy had gotten. "I've taken longer, but damn you're thick!" was her comment.

Deb looked at the first two and said, "Thanks for warming him up for me. Now let's see what I can do."

Before she started, she looked at me, winked and said, "Oh, and don't hold back because I love to swallow too!"

With that, she started slow, licking and sucking on the head but as the three of us watched, more and more of my cock disappeared into her mouth. She passed Wendy's mark easily and then with a few more bobs of her head she got to where the other woman had stopped. When she pulled away, we all thought she was done but instead she said, "Damn you are big, I'm going to enjoy this!" and then went back to sucking.

To my amazement and I think the other two ladies as well, she took more and more of my cock in until I could actually feel the head and the first couple of inches sliding into her throat. I'd seen porn where guys got deepthroated but other than Donna, no one had even licked my cock so this was not only new but felt amazing. It wasn't long before I could feel her nose hitting my crotch with every bob of her head and that was too much for my 19-year-old brain to handle and it wasn't long before I erupted. I was fully expecting her to pull away when I started cumming but instead she just held my cock as deep as she could while I literally came down her throat with the first couple of spurts. She pulled back far enough to catch the rest of my cum in her mouth before swallowing most of it. With a cummy smile she said, "Damn that was a lot of cum! The only problem with deepthroating is if I don't pull back in time, I don't get to taste it."

Wendy said, "Holy shit, that was hot but I was hoping to taste him, maybe another time."

Without missing a beat, Deb said, "No time like the present!" and grabbed Wendy to give her a long, hot kiss with lots of tongue.

At first Wendy seemed to pull back a little but quickly relaxed and soon Carol and I were watching the two of them kiss as Deb shared my cum with Wendy. Not surprisingly, that got me slightly hard again. When Carol noticed she said, "Hmmm, that looks promising for later!"

I just grinned at her and said, "Just let me know, if not here maybe another time."

By the end of the night, I'd enjoyed the feel and taste of quite a few pussies on my tongue, a couple of others had tried sucking me but none were able to get all of me in the way that Deb had. Before I left the party, Donna and I spent a few hours fucking. She'd obviously heard about Deb deepthroating me because she tried that as well but couldn't get all of me in without gagging so I happily settled for fucking her to quite a few orgasms before I came myself. When I got home, I only had about $800 from 'tips' but that was because I'd told Donna that with all the other 'benefits' of the night, she didn't need to pay me anything herself.

Donna had told me she was ok with me meeting up with her friends outside of her parties as long as I was discrete. Judy, the lady who enjoyed my tongue in her bum had asked me to pop by her place one evening and I found that she enjoyed more than a tongue in her ass. After me giving both her holes another good licking, she pulled out some lube and said, "Donna tells me you've got a good-sized cock, I'd love to feel it in my ass."

I'd never done anal but like everything else, I'd seen enough movies so I was definitely good to try it. When I undressed, she stroked my cock a few times before saying, "Holy shit, that'll take more lube than I was figuring on and I might walk funny tomorrow but it's gonna be worth it. "

She coached me on when to push, how hard and when to pull back slightly. It took a bit of work before I was able to actually get all the way into her ass with her moaning and groaning about how good it felt even though it hurt a bit. I fucked her ass for as long as I could until I finally flooded it with cum. I never fucked her pussy but any time we got together; it was a given that I'd be sliding my cock into her ass until we'd both cum at least once.

Over the next couple of years, I had no shortage of women who were quite happy to have sex with me. Sometimes it was at one of her parties, sometimes it was at someone else's party and sometimes it was just a one on one with them. Some of the women were single but a lot were married so things with them had to be kept a lot more discrete, other than the few who's husbands knew and just didn't care as long as their wives were happy. I never kept an actual tally but between various parties, a few threesomes with a couple of the women or one on one's, I likely ended close to $15,000 ahead which ended up being my down payment on a house. I never technically charged for sex, if they wanted to give me something that was fine, if not then just getting laid was fine too. My mom often asked why I never had a girlfriend but seemed ok when I told her I wanted to focus on my education. Dad never said anything until one day mom was out, we were doing some yardwork and enjoying a beer. Out of the blue, he surprised me by saying, "I've heard through some of my buddies that one of the guys at the club is doing really well with the ladies and apparently making some money at it. I just hope he's careful and doesn't either catch something, get someone pregnant or piss of a husband."

Then looking at me he added with a grin, "Damn I wished I'd been able to do what you're doing when I was your age!"

Nothing more was ever said by Dad and I kept my job at the country club. After graduating, I got a promotion to work in the office and of course kept 'looking after' a few of the women I'd gotten to know. I met with Donna on a regular basis, Judy enjoyed my cock in her ass occasionally and Deb was a somewhat regular connection for an awesome blowjob/deepthroat and often a fuck too.

Flashing ahead another 15 years, I was not only still working at the country club, now I was managing the entire operation and was working on a deal to buy it from the current owner. I'd finally met a woman named Samantha that I quickly fell in love with. She enjoyed sex as much as I did and had no problem with the size of my cock. We'd gotten married about 5 years ago and while we weren't planning on having any kids yet, both of us were open to it if it happened. Marriage pretty much killed the 'extras' that I'd been having over the years but I still got together with Donna when our schedules lined up. Samantha had no idea that I was still having sex with Donna and seeing as my wife and Donna's daughter was the same person, we definitely wanted to keep it that way!

12
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5 Comments
Campus77Campus776 months ago

Definitely an upscale country club. I do know a friend who spent a summer in a similar situation. He bought a Vet. Thanks for entertaining me for a while.

PanelholesPanelholes11 months ago

Great story. Really enjoyed the premise… leaves a lot of room for sequels, spin-offs, etc.

One constructive criticism, a little more attention to punctuation will help it move more smoothly.

Got 5⭐️from me!!

TeenStudforOlderWomenTeenStudforOlderWomen12 months ago

Great story. I really enjoyed it. Thanks for writing it.

roveroneroverone12 months ago

Never mentioned him by name but...

sheesh...hung bigger than top-name talent, lots very grateful milfs and gilfs...

but would say he's playing with fire doing Donna while married to her daughter

PS and also worked at a couple of country clubs-they're interesting places...

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