Country Club Fun

When I was in high school, I'd decided I wanted to do something in business so focused on that and when I got to University, I went into business admin with a couple of financial courses. Dad hadn't been able to get a college or university education but was quite supportive of me being able to do it. To save money, I stayed at home and the deal with my parents was that they'd cover my expenses to the same degree as my marks so if I had a 72 average, they'd cover 72 percent of my expenses. I still needed a part time job but unlike a lot of my buddies, I saved the money and studied so I could get better grades and pay out less. I'd been running an 80%-83% average for the last couple of terms so had saved enough to buy a decent used car.

A buddy of mine had gotten me a job at the local golf/country club. It wasn't much, I was basically a grounds-keeper or whatever they needed kind of guy but before and after hours, employees had free access to things like tennis and the pool. I'd played tennis in high school and was pretty good I I often took advantage of the courts and enjoyed a swim afterwards on the hotter days. One day I was just finishing at the tennis court and one of the pro's said 'hi', mentioned that I was a pretty good player and suggested that if I wanted to make a little more money, there were often members who wanted a partner for doubles or singles and would be happy to pay or at least tip generously.

That took me to staying after work or going in evenings and weekends and quickly found that I could make more in a week doing that than I was making actually working there. I knew eventually I'd want my own apartment so the 'extra' money was being put away for that as well as a few other things I wanted.

Of course, in my 19-year-old mind, I often fantasized that one of the ladies would want more than to play tennis but other than enjoying a flash or two of boob as they moved the right way and the occasional view of a panty covered pussy, nothing else ever happened but I enjoyed it all anyway.

I got along well with the rest of the staff and managers which is likely why I got my next break. I was just finishing my day's work and putting things away for the day when the banquet manager came up and asked if I could help him out that night because a couple of the guys had called in sick. I was tired and really just wanted to go home but when he told me I'd get $200.00 for the evening, I quickly agreed. After a quick shower and changing into the uniform he gave me, I was good to go.

My job was to take drink orders, refill buns/butter/condiments and keep the tables cleared. Thankfully I had a good memory so I was able to get the drinks back to the right people fairly quickly and got quite a few tips extra as well. All in all, by the end of the evening, I was up over $300.00 and was offered a spot there instead of my grounds work which I happily took. It meant some later hours but for the pay increase, it was well worth it.

Unlike a lot of my buddies, at 19 I was still technically a virgin. I'd had girlfriends but other than feeling a few tits and giving one or two a good licking which they seemed to enjoy, I'd never actually had sex. A couple had jerked me off until I came but had then not wanted to go all the way. The only blowjob I'd ever gotten was from a stripper that my buddies hired at my 19th birthday. I was so worked up that by the time she got the head in her mouth, I let go and she ended up almost choking on the cum. I'd never had a long-term girlfriend and I kept telling myself that I was pickier than my buddies but it was likely also just that I was too busy to worry too much about dating. Of course, I'd watched hundreds or maybe even thousands of porn flicks so I had a pretty good idea of what sex was and how to do it.

I'd only been working the lunches, dinners and special events for a month or so when one of the ladies, Donna, asked if I'd be interested in doing similar work at an event she was having at her estate and it would be $500 for the day which definitely got my attention. I'd played tennis with her a few times and not only had checked her out but noticed that she seemed to be checking me out as well. All I really knew was that her and her late husband had started a company and made lots of money. Let's face it, at 19, getting checked out by a well-built, attractive 40ish woman made for a great day. She'd been tipping me quite well through the evening so after checking with my boss to make sure there wasn't a 'conflict of interest' or anything, I let her know I'd love to do it. When I asked what I should wear, she surprised me by saying it was a beach themed pool party/dinner so a white t-shirt and black swim trunks would be fine and to be there by 11am or so.

When I got to Donna's estate, I was somewhat amazed. The front yard was the size of our whole property, the house was huge and when I got to the back yard, the pool was easily 30' by 60', there was a hot tub, sauna, a huge deck and lots of flower beds. It was a nice day so the trunks and shirt worked fine and when I met the other 2 guys who were there to help, I recognized one from the club and the other one seemed really chill as well. Before we started, the guy I knew from the club pulled me aside and asked, "So, how much did Donna tell you about the party?"

"Not much, only that there'd be 30 or so guests, mainly women, it's beach themed and I was here to help with food/drinks and possibly help with some of the activities like volleyball or whatever."

He just grinned and said, "Well, that's the one side of it. Here's the other - it's mainly a women's drinking day and a lot of them will be pretty sloshed by the end of the night. Odds are really good you're going to get your ass grabbed, body hugged, kissed and maybe more. I've only helped once before and by the end of the evening, there were topless women in the pool or hot tub and more than one with nothing at all on. After a woman grabbed my cock beside the pool the first time, I asked Donna what I should do and her answer was 'as long as they're the ones that start it, feel free to enjoy but just don't be the one to start anything.' By the end of the night, I'd been grabbed, kissed, stroked and gotten a hand job. I even had one woman ask me to go down on her but she was too old for me to want to play with so I declined. Just relax and it'll be one hell of a day/evening!"

Everything was ready, the company doing the cooking was there and by noon the guests were arriving and by about 1pm almost all of them were there. The youngest would have been in their min 30's and the oldest in their 60's but most were between 40 and 50. I recognized quite a few of them from the country club and the ones that recognized me usually gave me a quick hug. There were lots I didn't know and there weren't many guys there at all. It didn't take long for either the wraps to come off or for them to change and soon I was enjoying over 40 women in bathing suits, some were one piece, some were two piece and a few fairly small bikinis. The majority of the women were in pretty good shape and a lot of the suits didn't cover a lot. Big boobs, little boobs, firm boobs, saggy boobs and some were thin enough to actually see nipples but I enjoyed glances at all of them. I was kept pretty busy getting wine, beer or other drinks and it wasn't long before I got my ass grabbed for the first time. When I turned around, there was a 50ish woman standing there with a big grin on her face who said, "I thought that would be a nice way to get your attention for a couple more drinks."

I just grinned back and said, "No problem, what would you like?"

After getting the order for her and her friends, I went and got them and when I got back, she was bending over slightly beside the pool talking to a friend so I gave her bum a quick squeeze and when she turned around, I smiled and said, "I thought that would be a nice way to get your attention to let you know I had your drinks."

She smiled, then laughed and said, "I like the way you think...I'm keep that in mind when I need another drink."

Shortly after that, I was asked to join a game of keep-away in the pool with a group of women and a couple of the husbands. It didn't take long for that to be an excuse to one of the women to brush up against me, grab my ass or cock so I returned the attention. Thankfully the water was cool so in between gropes, I was able to 'relax' enough that when I either got out of the pool or was in the shallow end, there was no embarrassing bulge.

By then the BBQ supper was ready which helped 'stabilize' some of the people who had been drinking a little too much and by dusk, about half had left. Those that were still there more than made up for it as the orders for drinks seemed to be coming even faster and sure enough, there were several ladies who were now topless in the hot tub, pool or somewhere in between. I wouldn't have said any of them were 'model' material but at 19, pretty much any topless woman looks good and a couple of them looked great. One of them had both nipples pierced and when I took her a drink she asked, "Have you every sucked a pierced nipple before?"

When I said I hadn't, she cupped both boobs and said, "Then I guess these will be your first!"

The invitation was plain so I happily took her up on it and was rewarded with both a few moans of 'Mmmmm, yes!' and then a hot kiss when she finally pulled back. That seemed to set the bar for the next little while as I was rewarded with drink deliveries by either getting to suck their nipples, getting kissed or both. I noticed the other two guys were doing the same so as much as I would have liked to think it was just me, I knew it was likely just a bunch of horny, drunk women.

When I delivered a fresh red wine to Barb, one of the other women I'd met at the club, she spilled a bit of it on her bare chest and with a grin suggested it was my job to clean up any messes. I happily did that and when I kept following the 'dribble' down across her belly to the top of her suit she said, "Oh, I really don't want to get my suit stained" and arched her bum up off the lounger.

That invitation was pretty clear so I pulled her bikini bottoms off and was treated to the sight of a trimmed but not bare pussy. Often in porn, the women were shaved bare but I certainly didn't mind the trimmed look either and her pussy lips were definitely larger than I'd seen before too. After that quick look, I went right back to licking except now I was able to lick right down and across her pussy. "Oh fuck! It's been years since my husband has done that, please don't stop!"

I really didn't have any intention of stopping unless she told me to, so for the next few minutes, I happily licked, kissed and nibbled on her pussy until she finally grabbed my head and moaned, "Yesssss, cumming!" before letting go, smiling and saying, "Thank you, you're very good at looking after the guests!"

About 15 minutes after that, Donna pulled me aside and said, "So, I hear you took Barb's suit off and went down on her?"

I was in a bit of a panic as I replied, "Yes, but one of the other guys you'd used before said as long as they initiated it, that it was ok to continue and I was sure that's what she wanted."

With a big grin Donna said, "Oh, that's what she wanted all right. In fact, she made a point of telling me and several other ladies just how good a job you did and now others are asking if they can 'borrow' you for a few minutes sometime before they go home."

Relieved that I wasn't in trouble, I said, "Oh, ok. So, what should I do?"

"Follow me so we can talk a little easier" and with that, she headed into the house. I was expecting to chat in the kitchen or living room but instead she led me right to a spare bedroom.

"You've obviously figured out that a lot of the women are looking for a bit of harmless fun while they're here and about the only thing that doesn't often happen is actual sex, at least not as far as I know. A lot of the women here are friends, but they're also either married to someone or somehow connected to a company that I work with so if they're happy, I'm happy. There's a good chance I'd be breaking the law if I asked you to do anything sexually with any of them and possibly make some money but if you wanted to, I'm sure that a few of them would be quite happy to come in here and sample the oral skills you'd given Barb except a little more discretely and I'll bet you'd get some nice 'tips' too."

"So, you're saying that if I just 'happened' to be in here, there's a good chance that a few of your friends might pop in, enjoy a bit of a licking and possibly leave me a tip?"

"Ya, that's pretty much it. You've been working pretty hard so I'd have no problem if you wanted to stay in here for a bit of a 'rest' if you'd like."

Damn, a chance to see and taste a variety of pussies, likely get tipped and who knows maybe one of them would want to get fucked, either tonight or another time seemed like a dream come true so I quickly agreed that a 'rest' might be a good idea.

With an even bigger grin, Donna said, "I hoped you'd say that and seeing as I'm already here..." then without saying anything else, she peeled off her one-piece bathing suit and I was treated to the sight of her fully nude. Even though there was a slight sag to them, her boobs still looked quite firm and her nipples were nicely hard. She definitely spent time at the gym because she was in far better shape at what I'd guess were high 40's than some of the women. Unlike Barb, her pussy was totally bare and when I suggested she lay back and enjoy, her reply was, "I was thinking more like you lay back and I'll straddle you and enjoy."

I was fine with that so I lay down and she moved so her knees were on either side of my head and her pussy was right over my mouth. Then for the second time in the evening, or in my life for that matter, I was enjoying the feeling and taste of a woman's pussy who was old enough to be my mom. Her pussy was already slightly wet and as I started licking, it quickly got wetter and wetter again. From her growing moans, I figured I was doing a good job and when she did cum, it was with a loud, "Oh fuck yes!" and I could feel the wetness of her juices trickling down the sides of my face.

When she moved off, she said, "Well, you certainly do have a talented tongue - I'll let any of the ladies who are interested know that you're 'resting' in here."

It didn't take long before the first woman came in and by the time the party wound down, I'd likely eaten a dozen different women, some of them more than once. Some were shaved, some trimmed, some totally natural. There was a noticeable difference in how wet they got and two even squirted when they came. One of the older ones, I think her name was Judy, must have had a bit of a kinky streak because as she rode my face, I heard her say, "There's an extra $50 in it for you if you're ok using your tongue on my bum."

I'd never done that with anyone before but figured for $50, I'd find out if I liked it and if not then it would be the last time I did it. As it turned out, other than the kinkiness of it, it really didn't do much for me but she certainly came really hard. Who knows, maybe it would be something I'd surprise a girlfriend with somewhere down the line but then again for another $50, there's a pretty good chance I'd do it again for her if she wanted me to. It was well past midnight when Donna came back in and said, "Well, that was definitely a successful party! Everyone else has gone home, so I thought I'd give you a personal good bye."

I was expecting her to want to get eaten one more time so I was a bit surprised when she undid my belt and eased my pants down. Apparently, I wasn't the only one surprised because just as my cock came free, she said, "Holy shit! If the others knew you were packing like this, I'd never have gotten them to go home."

I'd watched enough porn to know that I was fairly well hung at just over 9" and pretty thick but didn't consider myself huge. In real life, I'd never seen another guy hard so I was judging my size against what I'd seen in porn videos. Apparently, Donna thought it was impressive because even as she was licking and stroking it, she kept whispering, "Damn you're huge!"

My first clue that she wasn't kidding was when she was only able to a bit more than half of it into her mouth before she started to gag a bit. It still felt damn good but just as I was getting close to cumming, she stopped. I figured that was it so I was quite happy when she looked at me and said, "I'd planned on sucking you until you came but with your size, I've just got to feel that inside me" and with that she straddled me and lowered herself onto my cock.

It took a bit just to get the head inside her and when it went in further, she moaned, "It's been a while since I've felt this full" and then proceeded to go all the way down until I was fully inside before lifting back up again.

I'd seen lots of sex in porn flicks and knew it would feel good but the sensation of her hot, slick pussy sliding up and down over my cock felt hundreds of times better than any lubed hand I'd ever used when I jerked off. Thankfully there'd been a bit of a break between her sucking me and sliding onto my cock so I was able to hold off a little bit longer but after less than five minutes of her riding my cock, I couldn't hold back and was soon filling her pussy with cum. It had been a while so by the time I was done cumming, it was already oozing out around my shaft.

"Oh my God! I'm not only glad I came back in but that no one else got a chance to find out just how big you are. If you're not in a hurry to get home and think you can get hard again, I'll bet you could last a whole lot longer the second time."

I definitely wasn't in a hurry to get home and she was right; I lasted a whole lot longer the second time and with her on her back and her legs up, I was also able to get even deeper which made all the difference and she must have cum 5 or 6 times before I came again. There wasn't any passionate kissing or touching, but the sex was amazing and when I slid out, I heard her say, "Wow, that was the best sex I've had in a long time. I'll bet you've pleased lots of women."

Hearing her say it was the best sex made me really happy but I wanted to be honest with her so I said, "I'm glad! Not only was it the best sex I've ever had, that was the first time I've ever had sex with a woman."

The look of surprise on her face said it all as she stammered, "What? That was your first time to fuck a woman?"

I nodded and said, "Ya, after a bit of groping and maybe a hand job, they always decided they didn't want to have sex."

She just grinned and said, "With the size of your cock when it's hard, I can understand why but I sure as hell loved it! I think you'd better call your parents and let them know you had a couple of drinks and will be crashing here tonight instead of driving because you've got a lot of catching up to do!"

Damn, she was right! Over the next 8 or so hours, we fucked, had sex and first thing the next morning we had a long, slow session that was the closest we could get to making love without actually being in love. We tried all the basic positions, a few one or both of us had seen in porn and then went back to the ones we enjoyed the most. I had no idea how many times Donna came but it was well over 10 and by the time I'd left, I'd just had my 5th one. We chatted a little and I found out that Donna's husband had died 9 years ago and she had a daughter about my age but she'd gone to a university in another state so she wasn't around much anymore.

After getting home and grabbing a shower, I went to my room to count my 'tips' for the night and on top of the $500 that Donna had paid me, I had almost another $500 in tips from the various women. Any time after that she had a party, I was always 'hired' to help and each time I came home with around $1000 more than I'd had when I left. I got together with Donna on a regular basis and we always had a great time, she showed me everything she could about sex and how to please a woman.