How I caught a Cougar. I fuck a woman twice my age. [MF]

Sorry for the long introduction, but I think it’s worth the read. Skip ahead for the juicy bits if you must.

This happened to me the summer after I graduated from college. When I was in college, I worked part time as a groundskeeper at a gated community. It was a good job, didn’t pay very well, but it was an easy job and my boss would let me work on summer break or whenever I was home from college. I worked there on and off over a number of years throughout high school and college.

Lisa was the supervisor for the housekeeping staff. She was a 40- something, single, divorcee, about 5’6”, 145lbs, shoulder length dirty blonde hair, blue eyes, a nice rack, and round ass. She usually wore a blouse with tight black slacks that really showed off her ass, or sometime she’d wear a skirt with heels that made her legs look really nice.

She had always pretty friendly with me, but that summer, she seemed up the ante. Maybe it was my 22 year old brain, or maybe it was from reading a few too many Penthouse letters, but it seemed to me that she had taken a keen interest in me. During lunch break, she’d invite me over to sit next to her at the picnic table in the break area. She would sit really close to me, her leg next to mine, pressing against me, or she’d give my arm a squeeze and compliment me on my tan.

She often complained about her ex-husband, Dan, what a dead beat he was, etc. One day, I’m not even sure how it came up in conversation; she complained that he was terrible in bed. He wouldn’t go down on her and he was a one pump chump that rolled over after he was done and left her unsatisfied. “That’s a real shame,” I said. “Yeah it is, it’s so hard to find a good man,” she said wistfully.

Now, I never thought our flirting would go any further than that, she was twice my age, and a supervisor at work (not my actual boss, but a supervisor in the same department), things could go bad for me quickly if I wasn’t careful.

A few days later, Lisa twisted her knee at work and had to have surgery on her ACL, she was going to be out on convalescent leave for several weeks. Meanwhile, the summer was coming to an end and I was shipping out for the Army in a few weeks. I figured I had missed my opportunity, if there ever was more than just some good natured flirting with an attractive lady.

Over the next few weeks I hatched a plan…

I was shipping out in less than a week, so technically I wasn’t an employee at the company anymore, and I had a good reason to drop in and see Lisa at her house. I’d bring her some flowers and a “get well soon” card. If I was wrong, I’d be the nice guy that dropped off flowers. If I was right….well, then I was about to experience a Penthouse Letter. “Dear Penthouse, I never thought this would happen to me, but…”

From our lunchtime chats, I knew that Lisa lived alone. I drove by Lisa’s house to make sure she was home, then stopped off and bought some flowers and a “Get Well Soon” card, and headed over to her house. I tucked some condoms in my back pocket, Just In Case, screwed up my courage and walked up to the front door and rang the bell.

It seemed like forever before the door swung open, and…

SHIT! Some woman that was definitely NOT Lisa opened the door, “Can I help you?” she asked. “Uh yeah, um, is Lisa here? My name is Justin, I have a delivery for her.” I stammered. Shit, shit, shit. This was not going as planned. I know this is her house, she lives alone, and her car is the only car in the driveway. Shit. “Yes, she is, hold on a minute.” She closed the door partially, and I heard her say, “Lisa, there’s a young man here for you, his name is Justin, where do you want the flowers?” “uh huh, ok…”
“Come on in,” she says opening the door all the way. “Hi Justin, I’m Nancy, Lisa’s neighbor.”
Well, shit, that’s better, but still an unexpected development, I think to myself. As I walk into the living room, Lisa is sitting on the couch with her right leg propped up on pillows. Lisa beams a great big smile my way and gets up to give me a hug. She’s wearing some short cut off jean shorts and a sleeveless white button up shirt, I can see the outline of a dark colored bra through her shirt. As she hugs me, I feel her breasts press into my chest, and her hug lingers for a second longer. My dick stirs in my jeans a bit. “Aww, you brought me flowers, that’s so sweet!” Lisa says. Nancy says “I’ll get a vase for them.” and disappears into the kitchen. “Oh, I got you a card, too,” I say, producing the “Get Well Soon” card. Lisa gives me another hug and a peck on the cheek, then offers me a seat on the couch next to her. I think to myself, this could still work out in my favor, just need to get rid of Nancy…

Nancy returns in a few minutes from the kitchen with the flowers in a vase and sets them on the coffee table. Nancy says, “Ok Lisa, I better get going, I’ll see you tomorrow. Give me a call if you need anything.” “Nice meeting you Justin.” she says as she heads out the door. Whew!

Lisa and I make small talk for a few minutes, she thanks me for the flowers and the card again. She apologizes that her air conditioning is not working. Lisa says, “I’m a little warm, can you turn on the fan? As I get up to turn on the pedestal fan next to the couch, I say, “You do look pretty hot.” “That’s not all you can turn on,” she replies with a grin. Oh boy…

As I walk back to sit down, I ask her, “How is your knee is doing?” “Pretty well,” she replies, “I can walk on it, but I’m not ready to go back to work yet.” “Do you want to see the scars?”

I pause and look at her leg stretched out on the pillows, I notice her red painted toenails (I love red painted toenails) as I study her shapely leg, I squat down at her foot as she points out the four tiny scars on her knee from the arthroscopic surgery. As I look up, she shifts her left leg slightly and I catch a glimpse of her white cotton panties with wisps of dark brown pubic hair peeking out. My dick stirs in my pants as I stand up and sit back down on the couch, wondering if Lisa moved her leg on purpose to give me a view, or if she noticed the growing bulge in my pants.

As we continue to make small talk, I tell her how much I enjoyed working with her and that I was shipping out for the Army next week. She asks me if I’d like some lemonade and gets up to go in the kitchen. My gaze follows her out and I check out her ass in those cut-off jeans as she disappears into the kitchen. She returns a few minutes later with two glasses of ice-cold lemonade, as she bends over to give me my glass, she gives me a perfect view right down her shirt! Lisa has a nice set of C-cups and I can see that she is no longer wearing a bra! As she sits back down next to me, I notice that the top two or three buttons on her shirt undone. Now the game is really afoot! Am I imagining things or did she flash me her pussy, then go in the kitchen, open her shirt and take off her bra so she could let me look down her shirt?

As Lisa sits back down on the couch, she holds the cold glass of lemonade against her neck and says, “I am feeling really hot, now.” A watch as a droplet of condensation rolls down her neck, along her collar bone, down her chest, then disappears into her cleavage. She leans forward and puts her lemonade down on the coffee table, then turns to me as she puts her left arm around my neck, and says, “Why did you really come here today?” My mind races! Shit! I am so busted! I begin to reply, “Well, uh I…” but I don’t get to finish as she leans in and kisses me. I kiss her back, awkwardly at first, then more passionately as our tongues intertwine. She takes my left hand and places it on her right breast as she leans in closer, kissing me. My semi-hard dick really springs to life, as I slide my left hand through the open buttons on her shirt and cup her breast softly, my thumb and forefinger teasing her nipple. She moans softly and gently bites my lower lip as I shift my weight and step over her left leg, now facing her and pushing her back into the couch. She grinds her crotch into my left thigh as I kiss her again, my right hand working a few more buttons free and teasing the nipple of her left breast. I kiss her neck softly below her left ear and work my way down to her collarbone. I step over her left leg with my right leg, and gently spread her legs wider with mine as I begin grinding the bulge in my pants against her mound. She moans as I unbutton the last remaining buttons of her shirt and eagerly begin kissing her bare breasts. They are a nice, natural, full C-cup, not perky, but not saggy, her nipples taut from my teasing and kissing.

I feel her hands rubbing my boner through my jeans as she fumbles with the belt buckle and zipper on my jeans, then my dick twitches as I feel her reaching into my boxers and gently stroking the shaft. My right hand wanders south to her inner thigh, then up through the leg of her cut-off jeans, I rub her mound through the thin cotton fabric, then slip a finger under her cotton panties and feel the heat and moisture dripping from her pussy. She gasps grips my dick tighter in her hand as I slip a finger in.

Using both hands, she grabs the waistband of my jeans and pulls them down around my knees. My dick springs free from its confinement and stands at full attention, straining against the fabric of my boxers. I’m standing in front of her now, my dick pointed at her face. She scoots forward to the edge of the couch, pulls down my boxers, and leans forward taking my dick in her mouth. She moans as I fondle her breasts as she strokes and sucks my dick, her tongue circling the frenulum on the underside of my dick head. She reaches around and grabs my ass, forcing my dick deep into her throat. “Is your knee OK?” I ask as she continues to ravenously suck my cock. Without even stopping for a breath, she nods her head, mumbles “Umhmm” and shoves my dick down her throat again. I’ve never had a deep throat blow job before, so it didn’t take long before I felt my balls begin to twitch and contract. “I’m about to cum” I said as she dug her fingernails into my ass cheeks as I blew my load down her throat. “Let’s go to the bedroom,” she said as she stood up. I put my hands on her shoulders as she shrugged herself out of her shirt, leaving it on the couch. I quickly kicked off my jeans and T-shirt and followed her down the hall. As she walked down the hall to the bedroom, she dropped her jean shorts to the ground and kicked them off.

As I entered the bedroom, she turned and faced me, I could see the outline of her pussy lips through the fabric of her panties was wet and see-through. “You’re wearing too much clothing,” I said as I knelt down infront of her. I nuzzled her pussy with my nose through the fabric of her panties, as I inhaled her musky scent. I hooked a finger into the waistband on each hipbone and slowly peeled her panties off. She laid back on the bed crossways, with her ass on the edge of the mattress. I stood up and carefully lifted her legs straight up in the air and began kissing her painted toenails, feet, and calves. My dick pressed against her pussy. I could feel the heat and moisture as her pussy pulsated and throbbed against my dick. “Oh yes,” she moaned. “Not yet,” I said as I slowly kissed down her legs until my tongue slithered into her pussy. I pressed her legs together and pushed her legs toward her head, her pussy lips peeking out at me. I licked and sucked and fingered her pussy until her legs began to shake, then gently sucked on her clit as I inserted two fingers into her pussy and curled them towards me until I felt the upper wall of her pussy, I rubbed gently until I found the spot I was looking for.

I felt her pussy contract around my fingers as I worked the G-spot and clit until Lisa screamed “Oh god, yes, I’m cummmiiiinnngggggg” as her entire body trembled and shook with a powerful orgasm.

“I have a condom if you want me to wear one,” I said. Lisa shook her head and said “I’m on the pill, I want to feel every throb of your dick inside me.” I was still standing at the side of the bed, I raised her legs in the air, wrapped one arm around her thighs and rubbed the head of my dick on her slick pussy lips, and slowly eased my dick in to her pussy a faction of an inch at a time. Her breathing became sharp and she moaned softly, “I’m coming again” as she attempted to grab my ass an pull me in deeper, but her arms were not quite long enough to reach as I slowly pumped in and out of her pussy at an agonizingly slow pace. This, of course, was driving her absolutely crazy. I let go of her thighs as her legs dropped to the side I began to thrust harder and deeper, each thrust driving her further onto the bed until I climbed on the bed and continued pump and fuck her until her eyes rolled back in her head and wave after wave of orgasm rolled over her. “I’m about to cum,” I grunted, “do you want me to pull out?” She dug her nails into my lower back and pulled me close as I filled her with cum.

“That was amazing,” she said, “I’ve never cum that many times at once in my life!” We laid there awhile longer until she fell asleep with her head on my chest. I left her there asleep with a smile on her face.
Five days later, I shipped out for the Army and I never saw her again.

Source: reddit.com/r/gonewildstories/comments/7egvaf/how_i_caught_a_cougar_i_fuck_a_woman_twice_my_age