Mrs Smith
When I graduated HS I was coming off football and track and field throwing event seasons, and was going to continue the throwing events at our local university. I was muscular with very little body fat, best shape of my life.
I had always been close to my aunt and uncle, he had done very well in rental houses and land purchases around town, from nothing to a multi-millionaire. They lived in a beautiful house in a gated subdivision and belonged to the local country club. I hung out at their house a lot, one because we had always been close even before the money, two, it was a beautiful place, and three because my aunt was a dark skinned gorgeous MILF who enjoyed going braless a lot and seemed to have more than a normal interest in me, but that's another story.
I had gotten my lifeguard certification at Scout camp a couple of years back and my aunt asked me if I would teach my cousins to swim. They were good kids and relatives and she was going to pay me for a couple of hours of work 2-3 times a week, which was more than I would have made at my 8 hours shifts nearly full time at the big box store I had worked at, so it was a no brainer. Not to mention I'd get to see my aunt jiggle around in her skimpy swimsuits a lot.
After a couple of weeks, my aunt asked me if I minded meeting them at the country club pool so she could talk to her friends. I was fine with it, they were mostly doctor and lawyer trophy wife young MILFs lying around the pool in barely anything drinking wine all afternoon while their kids played in the pool.
After a few weeks my aunt pulled me aside and said "some of my friends were wondering if you could teach their kids to swim too?" Most of them had mansions with pools like my aunt, some wanted me to teach them at home, some at the club. Easy money, MILF t&a, it was a dream gig. So I would take 2-3 famillies 3 times a week.
About midway through the Summer Mrs Smith (not her real name) asked me to teach her kids. She was a leggy blond with full pouty lips and a 34D natural chest. She was married to a doctor who seemed to always be gone. She asked me to come by a couple of times a week to teach her 2 kids.
She would always park herself by the pool in a skimpy bikini and polish off a bottle of wine by the time the lesson was over. I would catch her looking close when I would get out of the pool. I purposely started wearing unlined trunks that when they got wet would cling to me and show off the cock, which always seemed to be hard around her.
The feeling was mutual, I would stare at her as she would sun herself, her suit left little to the imagination. Her top was so skimpy I could see the edge of her nipples in the suit, and her thong bottoms showed off her perfect ass. She would catch me staring at her, I wouldn't look away, and she would just smile.
After a few weeks she started asking me if I would rub oil on her, of course I said yes, and the more weeks I did it, the more bold she would get. Like asking me to rub it on her thighs and parting her legs a little, undoing her top and having it down further on the sides. It was so obvious, it was clear she was enjoying it. And my cock proved I did too.
Finally one week I went over and went in the backyard to the pool like normal. She was laying out and the kids were gone. I asked about them and she said her husband had taken them to visit their grandma out of state and were gone for the week. I said ok I'll see you next week and she said no, its ok to stay I'll still pay you for the week. We laid out for a little bit, she had already taken down her first bottle of wine and started on the second.
She asked me to oil her and as I started and she untied her top and raised up and pulled it out from under her saying "I dont want to get oil on this its brand new. You dont mind do you?" Of course I didn't so as I was doing her back she would raise up slightly to slide her side boob up more to my hand. When I finished, she turned over and said could you do the front?
I was pretty shocked although it was hard to not see it coming. I was nervous because this had never happened and I didn't want to get in trouble and blow a good gig. I started to rub oil on her tits, not believing my good fortune. She pulled me down and kissed me and said let me rub some oil on you.
We switched places and she dumped a huge amount on my chest and legs and started working them over. As she got to my waist she pulled down my trunks and said we dont need these and pulled them off and squirted oil on my cock and started stroking me. I stopped her after a couple of minutes because I was already about to explode. She said "lets go inside I need some more wine" and she grabbed my trunks and headed inside leaving me naked to follow with her topless.
We went into a room and she got an old sheet and spread it on the bed and got some baby oil and we took turns oiling each other up. I took off her thong and she had a faint landing strip over her pussy. She took my hand and put it down there and started moaning. I knew there was no turning back so I started rubbing her, then licking. She started moaning more saying no one had licked her for years.
She pulled me on top of her and guided my cock inside and said "ooohhh gaaaddd" and started pulling me deeper inside her and humping me saying she hadn't been fucked in months. Apparently her husband had a side piece and was having an affair, she later told me this was her way of paying him back.
I started pounding her, I knew I wasn't going to last long seeing her big oily tits jiggling around. She's screaming I'm cominggg!!! and I'm doing everything I can to try to slow down and not cum too quickly. Finally on her second or third orgasm I couldn't take it, I told her I was going to cum and she said cum inside me, I'm on the pill. So with a couple of strokes as deep as I could push into her I started filling her with a couple of weeks worth of cum. It felt like I came for 2 or 3 minutes, so much my balls were aching.
We collapsed on each other and laid there. I couldn't believe it was happening. She was snuggled up on my chest and started kissing me. Then about 15 minutes later rubbing my cock which was already hard again from seeing this gorgeous woman nude in my arms. And here we go for round two.
This time I took over, flipped her over on all fours and started pounding her from behind. I pushed my thumb in her ass and it set her off. She was cuming and screaming oh fuck oh fuck, fuck me harder!!!!!!!, I lasted about 5 minutes, grabbed her hips, slammed into her and gave her every bit of cum I had left. We collapsed again and laid there for about 30 minutes, then showered and talked.
She said she had wanted to do that since the first time she saw me, she said her husband made her feel like she wasnt sexy anymore and she knew he was having an affair. I told her he was crazy that she was the hottest woman at the club pool. She kissed me and snuggled in my arms for awhile, then it was time to leave.
We only had one more chance to play before my time teaching her kids was over. When we would run into each other we'd smile and give that we have a secret wink. I heard she met someone else and ended up leaving her husband for him. She definitely taught me some sexual lessons, best summer ever.
