I used to be a pretty good tennis player and won some fairly large local tournaments. Then I messed up my knee and could no longer play at the competitive level, so I ended up as an instructor at a nearby country club. Mostly I teach wealthy people who have more money than talent, though once in a while I get some players with real potential. My favorite clients are the bored housewives who come in just looking for something new to do. Sharon was one such housewife. She was a nice lady in her 40s with shoulder-length reddish-blonde hair and a slightly plump build. She had two grown children and a husband who cared more about business than about her.

After two lessons, it became obvious that Sharon was a flirt with a dirty mind, and I began to relax and have fun with her. During her fourth lesson, she reached for a stroke and the skirt of her tennis outfit flew up, showing me—and everyone around who cared to look—that she wasn’t wearing underwear. When I realized we were alone on the court, I began to enjoy the view and intentionally hit the ball out of her way, making Sharon stretch and show off her ass and cunt. I learned she had a thick bush and curvy ass. As I admired her, it became difficult to keep playing; my racing mind and hard cock were getting in the way.
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The light of day had just begun to filter through the blinds as I lay under the blankets, listening to the soft patter of rain against the side of the house. I flipped the covers back and the coolness of the room immediately hit my naked body. I quickly scampered down the steps to the warmth of my robe.

The house felt cool as I went around and straightened things up, but thinking about the last conversation we’d had kept me warm.

I walked into the bathroom and turned on the shower, letting the steam rise before dropping the robe behind me. I looked in the mirror and saw my age appear on my face. I wished for a moment that I could look the way I felt, but after studying my reflection for a moment, I came to the conclusion that it could be a lot worse.
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It was a beautiful, sunny day when my husband Bill and I decided to take some photos of me in the great outdoors. I love modeling for him in skimpy, sexy clothing just as much as he likes taking the photos. We headed to a secluded place in the country.

Along the way I got myself in the mood for the shoot by undoing a few buttons of my dress and exposing my stocking tops and clean shaven pussy as Bill drove. By the time we arrived at our destination, we were both quite excited. Bill pulled over and parked the car and we got out to take some shots. Then I crawled into the back seat on my hands and knees and stuck my ass in the air, posing so he could take some more photos.

I leapt when I felt two of his fingers playing with my wet slit, and when he replaced his fingers with his tongue, I soon had a strong climax. I screamed loudly, and I was glad we were out in the country or else I’m sure plenty of people would have heard me.

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When I was in college, I was at a friend’s house and we were watching an NC 17 movie. Being horny, I went into the bathroom to jerk off. But the latch on their bathroom door didn’t engage fully, and as I was in mid jerk, my buddy’s mom walked in on me. She looked at me and even made direct eye contact, but didn’t say a thing, even though she could clearly see that I had my cock in my hand. We both froze for a moment, then she got a slight smile on her face, and I boldly started pumping my dick again. Within a few seconds I shot my come all over their bathroom floor, and I never once broke eye contact with my buddy’s mom.

After I finished shooting, she simply smiled and left, never saying a word. I was almost certain she’d tell her husband or my friend or maybe even my folks, but she never said a thing to anybody, not even me. Whenever she’d see me after that, she’d always get the same weird look in her eyes, no doubt remembering that day. I had my own fantasies about her after that day, too, but none of them ever came close to being fulfilled. That’s what started my attraction to older women, though.

Anyway, last fall I was riding the bus home late one night, and at one point the only passengers onboard were me and this Spanish woman in her mid 30s. She wasn’t outrageously attractive, but she wasn’t ugly, either. She was, however, wearing a short skirt, and every time she crossed her thick, shapely legs, I couldn’t help but take notice. After 20 minutes she crossed her legs again, and I noticed she was looking at me. She smiled when she saw I was watching, and I smiled back at her. Then she uncrossed her legs and let her thighs stay open, giving me a full view of her panties.

We continued to ride like that, with her pretending to read and occasionally glancing at me, and me looking up her skirt. After a few more minutes I had a raging hard on, and when she noticed the lump in my pants, she actually giggled a little.

She was obviously having a great time with our game, and she upped the ante by spreading her legs wider and making a “jack off” motion with her hand. After a quick glance toward the driver, I boldly took out my cock. She spread her legs wider, giving me a view of her dark pubic hair around the edge of her panties, and a dark wet spot began to show at her crotch, too. Then the bus stopped, and the woman quickly stood and got off.

Not wanting the fun to end, I stuffed my dick into my pants and ran off the bus to follow her, hoping this wasn’t a setup or something. She looked back at me over her shoulder and smiled, so I continued to follow her. She led me down a dark, dirty alley, then suddenly stopped and turned to face me. Not knowing what else to do, I walked up to her. Without saying a word, she reached out and grabbed my cock through my pants. She unzipped me and pulled my dick free, then turned around and leaned forward over a garbage can in invitation.

Quick as a flash, I got behind her. I pushed her skirt up to her waist and tugged her panties down to her knees. I kicked her feet apart and moved in. Then I drove my cock into her as she cried out, “Dios mio!” I held her hips and fucked her hard for only a minute or two before I lost it and shot my come inside her. She moaned when she felt it, and then her pussy spasmed and she came, too.

When we finished, I pulled up my pants and patted her on the ass. “Gracias,” I told her as I hurried away, my cock wet from our juices and her still dripping my come from her freshly fucked cunt.

I ran into her again a few weeks later, but like with my buddy’s mom, she just gave me a knowing look and didn’t say anything. The fact that she was with some probably contributed to that, too. But that’s okay. Because I know there will always be another hot MILF or cougar waiting for me right around the corner! — R.A., Royal Oak, Michigan

I’m 19 and my roommate Brian is 21. I’m a sophomore in college and he’s a senior. We’ve shared a room in the dorms since my freshman year, and when he goes home for the weekend, I have the room all to myself. When he’s here, though, it feels a lot like when I used to share a room with my older brother as a kid.

Brian has an on again/off again girlfriend back home named Anna. Whenever they’re “on,” Anna comes to visit on the weekends. The last time she came, they went out to a few bars on Friday night and didn’t come home until 2:30 A.M. They didn’t turn the lights on when they came in, so they wouldn’t wake me up, and I kept really still, so they definitely figured I was asleep. I thought they’d just get into bed and go to sleep, since it was pretty late and I figured they were kind of drunk, but they had other plans.

Brian sat on the side of his bed and Anna stood facing him in the space between our beds. In the moonlight, I could see Anna’s sexy body as she pulled her sweater over her head and dropped it on the floor. She undid her jeans and pushed them down before she slowly and seductively slid her tiny panties off. That’s when I saw her awesome ass, and my prick grew hard.

When she bent over, her luscious ass stuck back toward me, and it was so close I could have easily reached out and touched it. Instead, my hand slowly stroked my hard cock as I watched Anna suck my roommate’s dick. Her body blocked most of the action, but I knew what she was doing by the sucking noises she made and the sight of her head bobbing up and down. Pretty soon I heard Brian moaning and saying, “Ahh, yeah! Swallow it! Swallow every drop, babe!” And it was obvious that’s what she did.

After Brian was finished coming, Anna stood up and went to the bathroom. When she came back out, she got into bed with Brian and for the next half hour I could hear their moans and gasps and the rhythm of the bed creaking as they fucked.

When things slowed down, I could hear them whispering to each other, and I figured the show was over. But, wow! What happened next really surprised the hell out of me!

Suddenly Anna was sliding into bed with me, totally naked. Her hand went to my now hard cock, and she started to slowly stroke me.

“I knew you weren’t sleeping,” she whispered in my ear as her hand kept pumping me. Then she asked, “Do you want to fuck me?”

With my heart racing and my head full of every fantasy that I’d ever had about Anna— and there were a lot— I squeaked out a quiet “yes.”

She pulled me to her and spread her legs as I got between her thighs. I easily penetrated her warm, sloppy hole, which had just been fucked by my roommate. I drove into her as if it was the last time I’d ever fuck again, and despite the fact that she’d just been fucked, her cunt was still tight and felt really good around my cock.

I came inside her pretty fast, then rolled off her so she could get up. She gave me a quick kiss, then climbed back into bed with Brian, my semen mixing with his and trickling out of her freshly fucked hole.

After she fell asleep, Brian asked if I’d enjoyed myself, and I said I had.

Now Anna visits more often, even when she and Brian are in one of their “off” phases, and we have our own fun together.— T.K., Milwaukee, Wisconsin