The diner was closed, but the waitress was open, all the way.

My first experience with a cougar happened when I was in college, and it kind of set the tone for my future relationships.

During my junior year I was holding down a part-time job as well as attending classes. One Tuesday night I got out of work shortly before 10 o’clock, and decided to grab a bite at a nearby diner before heading back to my dorm. I was very hungry, and my mouth was already watering as I envisioned a juicy cheeseburger and a big pile of fries.

But as I reached the door of the diner, a waitress inside was just locking up, and she shook her head at me through the glass as she flipped over the “OPEN” sign to the side that read “CLOSED.”

God, I was starving, having put in a full day of classes in addition to several hours on the job. I could practically taste that burger, and I wasn’t about to be denied. Summoning my most pitiful expression, I dropped down to my knees and began wringing my hands in mock desperation.

The waitress, who looked to be in her mid-40s, crossed her arms across her ample tits and just stared at me. I kept up my pleading act until she let out what looked like a sigh of exasperation, rolled her eyes and reluctantly opened the door. I jumped to my feet and quickly stepped inside before she had a chance to change her mind.

Once inside, under the fluorescent lights, I got a good look at her. She wore very little makeup, but she really didn’t need it. She had the beginnings of a few laugh lines around her eyes, but other than that she was beautiful. Add to that her double-D rack, full hips and shapely legs, and I was ready to forego my burger in lieu of her.

As she locked the door again I thanked her for letting me in and sat down at the counter. I asked her her name, but she ignored the question and asked me what I wanted. I told her, and she fired up the grill and the fryer and started preparing my order.

She obviously wasn’t interested in conversation, but I was intrigued by her raspy voice and no-nonsense attitude, as well as by her looks. I did my best to charm her, but to no avail; it seemed as though she just wanted me to finish my meal and leave so she could lock up and go home.

I went back there the next night, and the night after that, again just at closing time. Eventually she loosened up enough to tell me her name was Regan, and that she wasn’t just a waitress, but the manager. On the fourth night she told me the meal was on the house, and I knew she was starting to like me.

On the fifth night I arrived to find the door to the diner unlocked. When I went in there was no sign of Regan, but my burger and fries were waiting for me on the counter. I figured she was in the back office, so I wolfed down my food and made my way back there, where I found her hunched over a pile of receipts.

“Still here, college boy?” she asked, without looking up. “Feel free to let yourself out. I’ll lock up behind you.”

In spite of her attitude, I knew that wasn’t what she wanted; she had obviously set this situation up deliberately. I said nothing, but waited until she came out from behind her desk, and as she walked past me I grabbed her hand and swung her around to face me. I told her I wanted to thank her for dinner, and then planted a hard kiss on her mouth. It took all of two seconds for her to start kissing me back, and then her tongue was halfway down my throat.

I backed up until my ass made contact with the edge of her desk, pulling Regan’s plush body against me. She was wedged between my legs, her soft breasts mashed against my chest. I worked my hands under her skirt, palming her ass, knowing she could feel my raging hard-on against her belly. Though I wanted to crawl up under that skirt and suck her off, I kept kissing her, changing the angle, grinding against her until she began to moan and hump her body up against my cock.

“Damn, I’ve wanted to fuck you since that first night!” I told her. Then I pulled her blouse open, hearing the sound of buttons pinging against the wood floor, and tugged the cups of bra down to reveal her big tits.

God, they were awesome — full and round and begging to be sucked. I lowered my head, closed my lips around her long nipples and sucked hard on those extended buds. My cock was threatening to explode as I moved back and forth between her breasts. Squishing those big globes together, I made a mental note to fuck her tits and come all over them, once I had fucked her cunt.

Regan moaned and continued to grind her mound against my aching cock. I knew I had to get inside her soon, or I would lose it. Abandoning her luscious breasts, I switched our positions so that her back was against the desk, then dropped to my knees, feverishly kissing her stocking-clad legs from her ankles up to her thighs. I pushed her skirt up to her waist, and with one quick movement yanked both her stockings and panties down to her ankles. The heady smell of her arousal made me want to dive right into her pussy. I pulled off her shoes, then the stockings and panties, tossing them over my shoulder. Gripping her ass cheeks, I had her spread her legs wide enough so that she had to lean on the desk for balance. She was hot and wet, and I didn’t hesitate to bury my face in her crotch and lap up the juices that already oozed out of her hole.

I licked her wet pussy lips from one end to the other, delving between her folds to slurp up all the good stuff before penetrating her with my tongue. As I did that Regan suddenly went wild, pushing herself against my face, trying to get my tongue to go deeper into her horny cunt. She began to shake and cry out as an orgasm rocked her body.

While she was still in the throes of climax I got to my feet and unzipped my jeans, then turned her around and bent her over the desk. My cock was wet with precome as I took aim and slammed it deep inside her cunt from behind. She screamed and moaned as she experienced another climax right on the heels of the first.

I held myself still as she quivered and spasmed, waiting for her to calm down. Then, calling on all the control I could muster, I pulled back slowly, leaving just the head of my cock inside her, then pushed back in. I did that a few times, until neither of us could stand it any longer. Regan growled at me to fuck her hard, and that’s what I did, taking her with strong, quick, punishing strokes. I held her down with one hand so her upper body was flush against the desk as I pounded into her, feeling my heavy balls tighten up against my body as I got closer to the inevitable. Regan’s moans grew louder each time I thrust into her, until her cunt muscles seized up around my cock, and I bellowed as the first shot of semen jetted out of me. The release was incredible, and seemed to go on forever.

When it was over and I’d come back to my senses, I looked around the office and noticed a small loveseat in the corner. I pulled Regan over and we both collapsed on it. She started to adjust her bra, but I quickly put a stop to that. “Don’t cover them up,” I told her. “They’re beautiful, and I want to look at them. In fact, take off your blouse and bra, so there’s nothing in the way.”

“You’re crazy,” Regan said, but she did as I asked. I stripped off my clothes and started stroking my quickly reviving cock as I watched her.

“Now the skirt,” I said, and a moment later she was naked. I asked her to spread her legs, and as she did so I could see a trickle of my come oozing out of her hole.

“Dip your fingers in your pussy, Regan, and get some of my come on them,” I said. “Yeah, that’s it. Now rub it between your breasts.”

She was looking at me like I was indeed crazy, but she indulged me. I had her do it a couple more times, then crawled over her.

“Has anyone ever fucked your breasts, Regan?” I asked her. “Because, they’re totally fuckable.”

“I must be out of my fucking mind,” she muttered, but one look at her taut nipples told me she was turned on.

“Push them together for me,” I said as I slid my dick between her breasts, and she did. I started pumping my cock between her mounds, watching the head playing peek-a-boo with her magnificent cleavage.

“How does it feel?” I murmured. It felt incredible to me. This was something I had always wanted to do, and she was the perfect woman to do it with.

“I can’t believe I’m doing this,” Regan breathed. I started moving faster then, watching her face as she licked her lips, then closed her eyes, giving herself over to the sensation of my thick cock fucking her tits.

“Do you want to taste my come, Regan” I asked as I felt myself getting close again.

“Yes,” she panted, her words sending an electric thrill through my body. “Yes, I want to, yes!”

After a few more strokes I pulled away, sitting back on my heels and aiming my cock at her tits before moving it to her mouth. My first shot hit her breasts, the second splashed over her lips and chin, and when she stuck out her tongue to lap it up, the third shot landed on her tongue. She swallowed it down, then scooped up the rest of my come with her fingers and slowly sucked them clean, apparently enjoying the taste.

“God, I can’t believe I’m doing this,” she said again. “Fucking some college kid. You know, I have a son about your age.”

“Yeah, but you’re enjoying yourself, right?” I said, grinning at her.

She didn’t answer me in words. Instead, she lowered herself to the floor between my legs and started sucking my cock.

Regan turned out to be my main fuck for the next couple of years, until I graduated. After that I moved home and never saw her again. But to this day I am still drawn to older women, and I guess I’ve got Regan to thank for that.

—

She found the walk-in pantry to be a good place for lying down

When I turned 45, my husband informed me that our marriage was over. He’d found himself a much younger woman and wanted to be with her. I was totally surprised, but I signed the papers, bid him good riddance, and moved back to my home state of New York.

I did get a good settlement, which allowed me to get myself a nice condo in the city, within walking distance of my new job. I also reconnected with some of my old friends, male and female. Fortunately, I had kept myself in shape, and I didn’t think I’d have any trouble once I felt ready to socialize again. I wasn’t looking to get married again, but I wasn’t dead either, and sex was something I both enjoyed and missed.

One weekend Jesse, my old college roommate, invited me to spend the weekend at her beach house on Long Island. I’d always loved going out to the beach when I was younger, so I was looking forward to it. Jesse wanted me to take the jitney out on Friday afternoon, so we could hang out and catch up, since we hadn’t seen each other since college. On Saturday she was planning to throw a barbecue for some of our other old classmates and their families.

Jesse was divorced, with two kids in college. She hadn’t updated any photos on her Facebook page, so I had no idea what her kids looked like now, but I couldn’t wait to meet them and hang out with my old friends.

Jesse met me when I got off the jitney, and we headed back to her house. Her kids weren’t due to arrive till the next day. We had a great time grilling burgers and drinking beer on the deck, while we reminisced about our crazy college days.

On Saturday I helped Jesse get set up for the party, preparing food, filling the plastic tubs she’d placed under the trees with beer, wine and ice.

People started to arrive around five that afternoon, and by the time the sun went down the party was in high gear, and I was feeling happier than I had in years. A lot of our old classmates had brought their kids along, and there were maybe six or seven college-age guys tossing a football around the yard. But there was one guy who seemed to stay on the sidelines, and more than once I caught him staring at me with interest. I didn’t think anything of it, but he was handsome enough that if I had been closer to his age I would have been all over him.

At one point Jesse asked me if I would bring out some more ketchup and mustard to top off the dwindling supply. I wasn’t sure where she kept the condiments, but after searching through several kitchen cabinets I remembered she had a walk-in pantry just off the kitchen area. When I opened the pantry door I saw a cord hanging down from the light bulb overhead. I pulled on it, but nothing happened. I gave it a few more tugs, with the same results. Then I heard the pantry door close behind me, and suddenly I found myself in complete darkness.

I turned back toward the door and bumped smack into a hard male body, letting out a yelp as I did so.

“That light fixture has a short,” a voice said. “But maybe I can help you find what you want.”

“Who are you?” I asked. My hands had landed on his muscular chest, and I left them right where they were.

“Not really important,” he said. “But I’ve gotta tell you I’ve been hard as a fucking rock since I first saw you.”

I felt his hot breath near my ear as he spoke, and the heat from his body made me conscious of how long it had been since I’d been this close to a man. I figured this had to be the young man who had been watching me so closely. Did I care that I was probably old enough to be his mother? Well, if my mind cared, my body overruled it.

I slowly lowered my hand, and a moment later I found that the boy wasn’t lying. His cock was big and hard through his shorts. I rubbed my palm up and down the length of it, and lost all sense of reason.

“Oh my God!” I moaned, as I he licked a path from my ear down to my neck. My hand slipped into the waistband of his shorts and felt the slippery evidence of his arousal. He pushed me back against the far wall of the pantry and pinned me there as he pumped his cock against my hand. Then his lips were on mine and his tongue filled my mouth. I sucked on it as his hands worked my breasts, and suddenly I flooded my panties and shorts with come. I should have been embarrassed, but I was too horny for that. I wanted his cock inside me.

He stopped kissing me and pulled off my tank top. I wriggled out of my shorts and panties, and asked him if the door could be locked.

“There’s a hook,” he said, and I heard him do something to the door. Then he was back, sucking on my tits as though he was starving. My tits are super-sensitive when I’m aroused, and his sucking and tugging and kneading only made me wetter. I felt moisture trickling down my thighs, and couldn’t wait anymore.

“Look, I appreciate that you want to make this good,” I panted. “But screw the foreplay — just fuck me!”

I didn’t have to tell him twice. He pushed me down on the floor and pulled down his shorts. When I felt him between my legs I reached down to guide him. His cock was huge, much bigger than my ex’s, and I couldn’t wait for him to fill me with it.

I wasn’t disappointed. He thrust that tool into me and I yowled with pleasure. Now, I love my vibrator — never leave home without it — but compared to the real deal, when the guy actually knows how to use what he’s got, there’s just no comparison in my book. I didn’t even think about the hard linoleum floor I was lying on as he thrust in and out of me. All I thought of was how good his cock felt, how he rolled his hips on each downstroke and touched all the spots that needed to be touched, how I was seconds away from having the mother of all orgasms.

When it hit, it was nothing short of amazing. I must have screamed, because suddenly his big hand was covering my mouth as I came, my muscles squeezing and milking that cock that continued thrusting in and out as it emptied its liquid heat into my pussy.

After he rolled off me all was quiet, except for the combined sounds of our heavy breathing. My fuck buddy’s heavy, sweaty body lay next to me, having just given me the best fuck I’d had in ages, and I still didn’t have a clue as to who he was. Then suddenly, he leaned over and kissed me, slowly and thoroughly, until I had to come up for air.

“Who are you?” I asked him. “I mean, we’ve been gone a good while. Won’t someone miss you?”

“No worries,” he said easily. “My mom’s used to me coming and going.”

“Your mom?” I said, sitting up. “Please tell me you’re not James!”

“Yeah, I’m James,” he said. “And I know who you are too.”

“Oh my God!” I groaned, as I felt around in the dark for my clothes. I had just fucked my friend’s son! Somehow I didn’t think her hospitality included screwing her son in the pantry.

“You know,” James said then, “I’ve looked through my mom’s yearbook hundreds of times, and I’d know you anywhere. You haven’t changed that much, and you’re just as hot as you look in the yearbook. I’ve jacked off to your image for years, but I never thought I’d really get to fuck you.”

I was at a loss for words. This was just too weird, and I had to get dressed and get back to the party. But James had started touching me again, distracting me as I tried to fasten my bra.

“We have to get back,” I said, slapping his hands away from my pussy. “I don’t want to have to explain this to your mom.”

I managed to find my shorts, but I couldn’t locate my panties. No way was I leaving without those. “James, I really need to find my clothes,” I said.

“If I help you find them, will you meet me tomorrow?” he asked.

“Yeah, sure,” I said. I was going home the next day, so I wouldn’t have to worry about keeping a date with him. Then I heard a click, and the overhead light went on.

“I thought the light didn’t work,” I said, gathering the rest of my clothes.

“It works — if you flip the wall switch,” he said, smiling. “Now, about that meeting tomorrow — ”

“Sure, I’ll be around,” I told him, lying through my teeth.

“So will I,” he said. “In fact, I’ve already told my mom that I’d drive you back to the city.”

I didn’t know what to say to that. I just looked at him as he got dressed, and even then it was hard for me not to put my hands on him again. Well, a ride back to the city would be a lot better than taking the jitney. But was I seriously considering fucking James again? Well, in all honesty, I was. And the next day I did. Several times.

I just hope Jesse doesn’t read this.

—

He was her student, but he taught her a few things as well

I teach art history at a small community college just outside of Chicago. Most of the young people who take my classes do so for an easy credit, and show no more interest in the subject than they need to in order to pass the course. Occasionally, however, I get a serious student, with a real passion for art and an eagerness to learn, and it is those students who make my job worthwhile.

A couple of semesters ago I had one such pupil, who caught my attention in more ways than one. His name was Steve. He was smart and talented, and often stayed after class to discuss different artists and exhibits with me. Though I was 20 years his senior, he was taller than me, with a good build and an engaging smile.

It is often my habit, on my days off, to go into the city to visit various art galleries and exhibits. Since I dislike crowds, I tend to choose days on which most people would prefer to stay home. So it was a particularly rainy and dreary Tuesday when I set out to make my rounds, expecting not to encounter many people, and certainly no one that I knew.

Sure enough, when I entered the first gallery, there were only three people inside — but I was very surprised to see that one of them was Steve! If it had been anyone else I would have tried to avoid them, but as it was I found myself strangely glad to see him.

I called out his name and joined him in front of one of the sculptures. We chatted a bit, and ended up viewing the rest of the pieces together. We went for coffee afterward, and then decided to hit the rest of the galleries.

When we’d finished viewing the art at the last gallery, we shared a cab back to the station, and we were both soaking wet by the time we boarded the train back to the college. It was the middle of the afternoon, and we had a car all to ourselves. We were both chilled, thanks to the damp weather and our wet clothes, and it felt good to snuggle together and talk about the art.

After a while, though, the conversation died out, and there was a strange silence between us. I’m not sure how it happened, but the next thing I knew, Steve and I were kissing and fumbling with each other’s clothes. I knew he was much too young for me, not to mention being my student, but at that moment nothing mattered but the connection we seemed to have established between us.

I climbed onto his lap, straddling his legs, and let him unbutton my blouse. I was still wearing my raincoat and couldn’t take off my bra, but Steve just pushed it down, exposing my breasts. He sucked and licked them as I held firmly onto his shoulders while undulating my pussy back and forth against the long hard ridge in his pants.

After a moment I slid off his lap and knelt on the floor between his legs, then opened his pants and pulled out his cock. Steve was breathing hard as I lowered my mouth to him. I sucked him all the way in and just held him there, getting him nice and slick with my saliva. Then I wrapped my fingers around the base of his pole and sucked and stroked, sucked and stroked. I was only sorry that I wasn’t able to slide his jeans down a bit more, so I could suck his balls. But I had a feeling I’d get my chance later.

I love sucking a nice fat cock, and his tool was almost as thick as my wrist. I lapped at the head and opened my throat to take him in deep again. I looked up at him and saw that his head was back, his mouth open. His hands tangled in my hair, and he began guiding my head up and down on his stiff rod, pushing his hips up and fucking my mouth. I sucked hard each time he pulled back, loving the sound of his deep groans.

When he came I took in all of his love juice, swallowing some but holding the rest in my mouth. I then sat up next to him and kissed him, sharing his cream.

There was no discussion as to what would happen next. Steve came back to my apartment and we ordered some food from my favorite Italian restaurant. We got out of our wet clothes and made good use of the time while waiting for dinner to be delivered.

Steve spread me out on the bed and told me he was going to have an appetizer. He started kissing his way down my body, and didn’t stop till he reached my cunt. By that time I was squirming and writhing on the bed, begging him to suck my pussy.

Steve slicked two of his fingers with saliva and worked them in and out of my hole, making sure to rub them over my clit. I began making needy sounds of lust when his tongue began vibrating against my little button. I couldn’t remember ever being this horny, but then I’d never had sex with someone this much younger than me. I started moving my hips as his fingers and tongue worked me over. Then he withdrew his fingers and worked them into my ass, while teasing my pussy with his thumb. He swirled his tongue around my clit as he sucked on it, and he couldn’t seem to get enough of me. He ate pussy as if he’d been doing it all his life. His skills would have put some of the older men I’d fucked to shame.

When I came it was with a gush, but he didn’t stop until I’d calmed down and my body had relaxed. His face was slick with my juices when he kissed me, giving me a taste of my own medicine.

I couldn’t wait any longer for him to fuck me, and I told him so. Steve told me to get up on my knees, then pushed my upper body down on the bed. I was breathing hard, dying for him to shove his dick into my wet cunt. When I felt his blunt cockhead rubbing back and forth at my entrance, I actually whined with impatience. I went so far as to reach back to grab his dick, but received a stinging slap on my ass for my trouble. My pussy was aching and empty, and I found myself pleading for him to fuck me.

When Steve finally entered me, it was inch by painstaking inch. He pushed in a bit and stopped to play with my clit. Then he pulled out and pushed in a little further. He did this several times, and he wouldn’t allow me to push back. I rubbed my aching breasts against the sheets in frustration until his cock was finally seated inside me as deep as it could go. He was so wide that I felt stretched to the max. It felt so good to be packed with his cock that I had to wonder what it would feel like to have him work that fat cock into my ass. Would I be able to handle it? Well, with any luck I would find out.

When Steve fisted his hand in my hair and started pounding my pussy I thought I’d die with pleasure. That thick hunk of meat touched all my sensitive areas over and over again. It was never-ending bliss. I came and came again, and he still kept fucking me. Then he pulled me up, wrapping his arms around me, one hand holding my breast while the other reached down to rub my clit. And all the while he continued fucking me.

When he came, his hard strokes and hot jets of come pushed me into a final climax. I fell face down onto the bed again, but Steve was still holding onto me, so we rolled onto our sides as I continued to twitch and moan through a series of aftershocks.

I was still recovering when the food arrived. I threw on a robe to answer the door, but we ended up sitting naked on the living room floor, eating our dinner off my glass coffee table. I had a perfect view of Steve’s rapidly hardening cock through the glass, and he had an equally nice view of my well-fucked pussy.

We’d eaten about half our dinner and finished off half a bottle of wine before our libidos got the better of us. I’d been staring at Steve’s cock all through dinner, and though my pussy felt swollen from use, I still wanted him inside me again.

We moved over by the fireplace then. I had Steve lie down on his back as I straddled his hips, grabbed his cock, and slowly lowered my pussy down onto it. The fit was tight, and I was still sensitive from our earlier coupling, but I wanted this ride more than anything.

I rocked and undulated my hips at a leisurely pace, while Steve fondled my breasts and rolled my nipples between his fingers. I began moving up and down, my pussy making squishing noises because it was still full of Steve’s come. I braced my hands on his shoulders and let his cock slip completely out of me, then leaned forward and rubbed my wet pussy back and forth along the sensitive underside of his cock.

“I need to get back in you,” Steve moaned, and I slid him back into my hole. He began pumping up into me, his thrusts hard and deep and fast. Our primal grunts and moans were the only sounds in the room, until they were replaced by screams and shouts as my convulsing pussy milked his spasming cock.

I saw Steve discreetly off and on throughout the rest of the semester, but when the term ended, so did our relationship. Oh yes, he got an A in my class. But he earned it.