Steve Meets A Cougar Ch. 01

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Eki 27, 2023 // By:analsex // No Comment

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I finished work, and drove home, as usual. I stopped at the Mall to pick up a birthday present for my mom. I gave a lot of thought about what to get her. She was forty-five and had just about everything she needed and most of what she wanted. But since dad died in a car wreck two years before, mom just kind of faded, and I wanted to cheer her up. I found a nice robe that I thought she would like; the robe she wore around the house was, to use mom’s word, “ratty.”

Dad had enough life insurance that money was never going to be a worry. Mom used some of that insurance money and bought me a pickup truck when I finished High School. I wanted to see what it was like to have a regular job before starting college. The truck got me to and from work and it was handy for running errands. .

I didn’t have any luck with girls; I guess I am kind of shy around girls. People told me what a good-looking “boy” I was. I thought I was ordinary looking. I was tall and gangly, a pretty good basketball player, and that, was about it.

Once I did manage to get a date with a pretty girl. We parked someplace dark and she let me feel her breasts. That made me cum in my pants and the girl laughed and laughed. I have a few guy friends, but the ones who didn’t go off to college, were busy with jobs and their girlfriends.

I used to wonder about mom. She and dad had a very active sex life. I could often hear them “doing it” through the wall between their bedroom and mine. I got to recognize the difference between the sounds they made when they came. And I made my own stifled grunts and moans when I ejaculated while listening to my parents having sex.

Now, though not as often as before, I could hear the characteristic sounds mom made when she was cumming; a series of long grunts finished by an “AAhh.” I wondered what she masturbated to.

For as long as I could remember, mom had been the woman of my jack-off fantasies. One time mom walked into my room just when my sperm was arcing high in the air and splatting on my chest. She had a look of horror and quickly left my room. Later, she apologized for barging in on me. And the next day she gave me a little sign that hooked over a doorknob and read “Do Not Disturb”

“Now Steve, you won’t have any embarrassing interruptions by little old ladies like me.”

I blurted, “You’re a beautiful woman, Mom. I was thinking of doing it with you when you caught me.” And as my face turned red and purple and I wanted just die, Mom touched my cheek very tenderly and kissed me softly on the lips.

“Steve, there’s just the two of us her, so we can talk plainly. I’ve wanted take you to bed, even before your father died.” She held my eyes to hers and said, “But we both know that ain’t gonna happen. Don’t we?”

I had to agree that of all the wrong things I could do, fucking my mom would be the wrongest.

But I was a nineteen-year-old virgin boy with boiling hormones. I was too shy to pursue girls. Besides, they didn’t seem as sexy as the older women, women my mom’s age. Maybe next year, in college, things would change.

Mom got all dressed up one day to go to one of the political meetings she was busy with. It was a woman’s political club and I had seen some of her fellow club members. They were in their forties and fifties and in my virgin mind, a few were extremely fuckable. God! I would have drank their bath water. That’s how bad I had it.

All alone in the house, I got on the internet and clicked on a link that said, “Find cougars here.”

I had heard the term “cougar” but wasn’t quite sure what it meant. It was a dating site that specialized in bringing “older women” together with young studs. As I navigated around the site, I was thrilled that women, attractive women, of my mother’s age, were advertising for young guys like me. I got out my credit card and signed up.

I used the search function on the site and found quite a few good-looking older babes looking for a good time with a young stud.

I hung my Do Not Disturb sign on my doorknob and settled down with a hand towel and read through the profiles of the women. Most had posted their pictures and they were good-looking for their age. They were not a bit bashful about what they wanted from a young guy like me. I couldn’t believe this was real. Reading their profiles made me so hot that I shot two loads into the towel.

With some of the pressure relieved from my balls, I was able to navigate through the site with a clearer head. I filled out my profile, giving honest answers to the questions, typing “virgin” into the experience box; and I uploaded a week-old photo of myself. It was a good shot of my face and bare torso. Mom had snapped it after I finished shooting baskets one afternoon. My hair was tousled, I had a crooked smile; rivulets of sweat glistened on my thin chest.

I wondered how many–if any–responses I would get. My imagination and sex glands took over and I shot two more loads into the hand towel.

All the İstanbul Escort next day at work I had visions of my inbox filled with emails from “cougars” who couldn’t wait to get me in bed. Finally, I got back home, wolfed down supper and went to my room. I made sure that the “do not disturb” sign was on my doorknob.

There was only one email in my inbox. The message read, “Wanna chat? Say about 7 tonight?”

I looked up the profile of the woman. She had posted two pics of herself. The first was a head and shoulders shot showing a brunette with short cut hair. She had a plain oval shaped face with a pert nose and a generous slash of lips. Her facial expression looked stern. There were crows feet wrinkles at the corners of her eyes and lips. Some of the cords of her neck were visible. Overall, she was very pretty for her age, which she claimed was forty-five. The same age as mom.

The second picture gave a different impression. She was exiting a car, smiling at the camera, holding a martini glass. Her skirt was hiked up, showing a lot of shapely, nylon clad thigh, the straps of her garter belt stretched tight. Wow! And she wanted to chat with me. My heart was beating hard even as my cock grew to its full length. I replied to her email, saying I’d be online at seven. It was almost seven already.

The cougar website had a chatroom function for cam chat with audio.

I got set up in the general room and looked for her screen name among the more than hundred on the list. A message box appeared. “Go to private room, ‘nylons.’ “

I’m not much of a chatroom fan, so it took me a while to figure out how to do that.

When I entered the room, I saw her screen name and mine beneath it, saying I just entered the room.

With a lump in my throat I typed “Hi!”

“Do you have a cam?” she typed back.


In a few moments and after a couple of false starts, we could see each other and talk.

“You are really a cute ki…guy.” she said.

She didn’t look as rigid as the face picture in her profile. Now she seemed softer, sensuous–eager, even. She was wearing a dark robe, closed to the neck. I told her she was beautiful and I meant it.

“Are you really a virgin,” she asked. That’s hard to believe for a guy as good looking as you.”

“Well, I am. I don’t know how to prove it.”

“Why do you want to have sex with an older woman?”

“I don’t really know…I’m just attracted to older women. Why do you like young guys”

“Because they can fuck all night instead of taking all night to fuck,” she said matter-of-factly with a smile. Then she stood and let her robe slip from her shoulders.

My cock was already hard as I stared at her image on my screen. I was speechless. Her breasts were not overly large and they sagged a little. Still her nipples pointed up. Lower down her waist looked thick, but not overly so. A garter belt held up her nylon stockings. She had great legs and my mouth watered at the sight of the dark hair between her legs.

“Now let me see yours,” she said with a chuckle.

I stood up, undid my jeans, and lowered them with my boxers to my ankles. My cock pointed straight up.

Nice cock,” she said. Can you make it cum for me?” I love to see a cock cum.”

“Yeah,” I croaked.

“Do it, then.”

I sat in my chair and adjusted the cam until she was satisfied with the view. She did the same and immediately began fingering her pussy.

I began stroking my cock for her while staring at the image of her fingering her pussy. In less than a minute a torrent of semen exploded onto my chest and belly. After I caught my breath, I wiped up my cum with my jackoff towel.

“That was very hot, honey,” she said. Just what I was looking for. Can you do that again? I mean tonight?”

“I can do it at least six times a night.”

“Can you get away tonight? I mean did you have a date or anything?”

“No, I was gonna stay at home.”

“Do you want to be with me tonight?”

“Hell yes!”

She gave me a name of a motel and the room number. I knew where it was; i passed it every day going to work. It was about ten stories, advertised free continental breakfast and had a dimly lit lounge. I had a beer there once, just to see if they would serve me without looking at ID. They did.

“I’ll be there at eight o’clock,” she said. Her screen went dark.

I was trembling when I rapped on her door. I realized we didn’t even know each others name. The door cracked open, she looked me over, opened the door wide, and pulled me inside.

There was a king-size bed facing a television and a low chest of drawers. In back was the bathroom. Just inside the door was a table with two upholstered chairs. On the table was a small leather purse, a bottle of whiskey, a couple bottles of club soda and a plastic container of ice cubes.

She was wearing a white blouse and a grey skirt. Her grey jacket was draped over one of the chairs.

She was short with a perky look. She looked up İstanbul Escort bayan into my eyes and said, “God! You’re so young.”

“i’ll be nineteen next month,” I said. She looked doubtful, so I showed her my drivers license.

She took it and studied it, handed it back. “You’re exactly a year younger than my son,” she said quietly, with downcast eyes. “And I’m nervous as hell, Are you nervous, too?”

I held out my hand, fingers spread. The tremor was very noticeable.

“Let’s have a drink and calm down,” she said.

With the drinks poured, we sat at the table and introduced ourselves. We both took deep swallows.

“Things never moved this fast when I was your age, Steve.”

“What do you mean, uh, Joann?”

“Call me Jo, Steve. Well, when I was your age, a million years ago, I had to pretend I didn’t want to fuck until my wedding night. That was expected of a girl then.”

It shocked me to hear a woman my mother’s age talk like that, but I acted cool. “So you waited until you were married?”

“I waited as long as I could. I found out it was a lot easier to get a boy to stop pawing you if you gave him a quick blowjob. I sucked quite a few dicks before I finally let someone–my late husband–get in my pants. Actually, I got to be quite fond of sucking cock. And got very good at it, too,” she said with evident pride.

My cock was uncomfortably stiff in its denim confines.

She tossed off the rest of her drink and I followed her example. She refilled the glasses. I was beginning to feel relaxed and I saw that the tension had left her face. We both sipped from the fresh drinks.

She wanted to know about my sex life; she couldn’t believe that a “good looking boy” like me didn’t have all the girls he wanted.

“All the girls I want are right in this room,” I said, feeling bold.

The remark sort of startled her and she smiled widely, and maybe was just a little embarrassed. “Aren’t you the smooth one,” she said, placing her hand on my bare arm.

I shrugged, confused.

Then a peculiar look came on her face. “Steve, this old lady wants to re-live a little of her girlhood.”

I met her eyes over the rim of my glass and nodded.

Jo set her drink down and dropped to her knees. She tugged at my legs until I got the message and bumped my chair over to get my legs completely out from under the table. She pulled my knees apart and placed her face close to my crotch.

Her fingers traced the outline of my cock under my jeans. Oh God! It’s really going to happen, I realized. She put her lips on my bulge and blew. Her breath through the denim was incredibly hot. She smiled up at me and asked, “Like that?”

“Yeah,” I croaked.

She tugged open my zipper, a few strands of my pubic hair sprang out. She pressed her nose into my open fly and held still for a few moments. I could hear her inhaling deeply. “Mmm,” she purred softly.

As I looked down at the back of her head, I noticed for the first time a few grey strands in her brown hair. Her head moved up and she fished my dick out of my jeans. When she had it in the open, she sat back on her haunches and stared at it. That was all I could take.

My cock started spurting a geyser of semen. Jo’s eyes grew wide and a smile of delight appeared on her glossy red lips. After the third squirt she put her mouth over my virgin cock. My first blowjob. I never could have imagined how good it could feel. My orgasm became almost unbearably intense and I cried out loudly and shuddered from head to toe.

Even after I stopped ejaculating, Jo continued to suck and make small sounds of pleasure.

Suddenly she stood up and said, hoarsely, “Let’s get naked and get in bed.”

I was out of my clothes and in bed in a jiffy; so was Jo, though she left her nylons and heels on. She wrapped herself around me and pressed her lips to mine. She slipped her tongue into my mouth and I felt a thrill in my cock and balls.

The two of us were writhing in pleasure and excitement. Her hands were all over me and i thrilled when my finger entered her cunt. My cock was still hard and ready, even after just cumming in her mouth. Gradually, we wormed ourselves into a position where Jo was flat on her back and I was on top of her. My cock rubbed against her coarse pubic hair. Jo reached between us and guided my virgin penis into her experienced cunt.

If the term delicious could be applied to the sense of feel, it certainly applied here, my first piece of ass. With my cock deep in Joann’s cunt, I seemed to have entered another dimension, where the only thing that existed was delicious pleasure.

Images without form raced through my mind. I was aware that my cock was slamming in and out of Jo’s well lubricated cunt at a steady rate. And I was aware of Jo’s nylon clad legs wrapped around my waist. There was only unbelievable pleasure and something else. I had the realization that Joann and I were ONE. The carnal pleasure in which I was immersed, became enhanced by this Escort İstanbul new…spiritual? dimension. I understood then, that I was in love with the older woman under me. My orgasm swept over me and everything went black.

When I came to my senses, I was on my back; a pillow under my head. Jo was lying beside me, stroking my hair; she was wearing a maternal smile.

“I love you,” I blurted.

“I know, dear, I know,” she said softly.

We lay in each others arms for a long while. Afterglow, I thought. Pure contentment.

Jo wiggled away from me, saying she had to “tinkle”. When she returned from the bathroom, she went to the table and began fixing drinks. I was sitting on the edge of the bed.

Jo turned around and handed me my drink. Her crotch was at the level of my eyes, and I stared. Jo cocked one leg up on the bed to give me a good look. I looked up and met her eyes.

“It’s all yours, honey. You can do what you want. That’s why we’re here, right?”

I touched it, gingerly. It had a puffy, swollen look. The hair at the entrance was damp. I could smell her and it was an animal smell, an intoxicating scent. My deflated cock grew rigid again.

Then she urged me back into the bed and had me lie in the center. She pulled my legs apart and knelt between them. She licked my shaft, then moved lower and licked my balls. I raised my behind to make it easier for her. She sucked one of my balls into her mouth and moaned. I moaned, too.

I couldn’t believe this was happening. Two hours ago I was a virgin; a woman of my mother’s age had sucked me and fucked me and she was now sucking my balls. I was now in an adult’s world now; I felt that in my bones.

Joann pulled my knees up until I held them high in the air. I felt her tongue moving around behind my balls. I inhaled sharply and moaned when her tongue licked my asshole. I had seen this done in porn videos, but never thought it would be done to me by a sexy older woman.

She alternated licking my asshole and sucking my balls for a long while. From time to time I heard her murmuring little sounds of pleasure.

In my position with my legs held high, my hard young cock was pointing at my face. A thin strand of clear fluid extended from the slit in my cock to my pubic bush. The action of Joann’s lips and tongue on my balls and asshole had me hovering in a zone of pleasure I never knew existed. I could have spent the rest of my life having my balls and asshole sucked and licked.

But Joann was going according to her own plan. She lowered my legs and took my penis into her mouth. In a few moments, my cock always in her mouth, she knee-walked around me until her hairy cunt was right over my face. It was the first time a woman’s pussy was so close to my face, but instinctively, I knew what to do.

I began licking through the wet pubic hair around her entrance and soon reached the pink inner petals of her pussy. The taste I recognized, was that of my own virginal semen, mixed with Joann’s copious vaginal fluid. I lapped it up eagerly.

The smell of her crotch was pleasant, yeasty, as rising bread dough, but not quite the same. I inhaled deeply, adding to the pleasure I felt from her sucking me.

Then Joann inserted a finger into my ass. It didn’t add or subtract from the pleasure that was washing through me; it was the idea that an older woman had her finger in me that tipped me over the edge and I ejaculated into her mouth. I heard her sort of choke as the first squirt took her by surprise, but she quickly recovered and swallowed all the semen I shot into her mouth.

Joann quickly climbed off of me and reversed her position so we were face to face. Her lips glistened with my cum and I could see that the lipstick in the center of her lips was worn away. She held my head in both hands and kissed me with tender passion. Her tongue slipped into my mouth and again I could taste my semen.

She cuddled against me, her head on my chest. “You must think I’m an awful slut,” she said. It was a question.

“No, I don’t,” I said honestly.

“Well, I want to be your slut, Steve. Her hand was feeling around my cock and balls. She moved a little and sucked my nipple. My cock grew hard in her hand.

She raised up and looked down at me. “I’m feeling anal, Steve. Would you like that?”

I was confused for a moment before I understood what she said. She wanted me to fuck her in the ass. The idea was exciting, and I said, “I’d like to try it.”

She went to her purse and took out a little tube of lube and a small vibrator. In less than a minute, Jo had my cock slick with lube from top to bottom. Then she worked some into her asshole

My heart was pounding as Joann straddled me and guided the tip of my dick to her anal ring. She very carefully lowered herself onto me. My cock felt terrific as it squeezed slowly into her. A couple of times she inhaled sharply; I could tell it was pain instead of pleasure. I had read and heard enough about anal sex to know there was pain involved with it. She finally had all of my cock in her ass.

It felt great to me but I sensed that it was hurting her. “We don’t have to do this it it hurts you, Jo.”

She smiled lovingly and said, “Just don’t move until I tell you. It does hurt, Steve. but it’s a good kind of hurt.”

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