This is a long one I'm afraid. Just a story I've been sitting on for a while, I hope you all enjoy.
When I was a teenager, my friends always found it strange how I never had a girlfriend. I mean, I’m not an ugly lad, I wasn’t back then and I’m not now, I was always and still am considered to be above average, I’m 6’0 ft tall, I’m in shape, with blue eyes, and brown hair, a born and bred rocker, jeans and a band t-shirt all the way, usually Iron Maiden. I’m nice and will do anything for anyone that I care about.
My problem was not that I couldn’t find a girlfriend; it’s that I didn’t want one. My interests landed squarely in the lap of older women, I found girls my age attractive, but I was mainly turned on by milfs, more importantly, cougars. It didn’t help that most of my friends had hot mums, and at 15 I was embarrassed by it. It all started when my mum used to have a friend called Diane, I was 13 at the time, and she always used to take my breath away. It didn’t help she liked to dress a little slutty and with her body that was impossible to ignore. She was a fitness freak, always toned, with paleish skin short blonde hair, large breasts and a firm tight looking arse. She was the one I masturbated through puberty to. She left the area when I was 15 and we lost contact with her.
When I turned 16 (16 being the legal age to have sex in England) I decided to get a girlfriend my age, because at this point, my friends thought I was either gay or something else, so I began to date a girl called Lauren, long brown hair, dark brown eyes with a naturally tanned, slim body, with lovely breasts and a gorgeous small yet firm arse.
I was attracted to her, and when I lost my virginity to her, the sex was amazing; I just couldn’t help but be more attracted to older women. My first sexual encounter with an older woman came from my oldest friend Tim’s mother Debby, she had known me all her life, seen me almost every day for 17 years and I was practically a son to her. At the time she was 38, with black hair, blue eyes, pale skin and a body to die for, half way between chubby and slender, with wide hips, a gorgeous round arse, and breasts that were still firm, and a good handful. She always wore long hippy style tie dye dresses, wore out of fashion flip flop shoes, and long sleeve cardigans.
One day while at Tim’s, I had accidently seen her in the shower, I got a huge erection, it was my holy grail. I decided that day would be the day I gave it a shot. Later on while she washed dishes, I purposely spilt a glass of orange onto the table, made to look accidental obviously. “Will, you clumsy idiot, come and get a cloth and clean that up” Debby had said with her usual playful banter. I walked over to her, an erection raging in my pants, this was my big chance, I leant in from behind, making sure she felt my cock, I knew she had, her face went red. I reached round, took the cloth in my hand, pushing my hips as much as I dare into her without my friend noticing. She had become flushed, the seed of the idea was planted in her mind, she would be thinking of that all day.
Throughout the day I would catch her looking over at me, from the corner of her eye, caught in a deep stare, or a passing glance. Me and Tim were in a band at the time, he was playing guitar through his amp, quite loud while we wrote songs. I needed the toilet and went to the loo. I passed Debby’s room on the way, and heard a faint sound, like someone talking under their breath. My heart pounding out of my chest, I slowly, quietly opened the door, the sight that met me, the smell, I was in heaven. Her tie dye dress pulled all the way up to her hips, her panties round her ankles. Debby was laid, knees in the air playing with herself. I could smell her wet pussy from the door, the sound of her fingers working magic filled the room, and she was moaning under her breath.
My cock was a raging monster, trying to burst through the zip on my jeans, I had to wait though, I had to let her make the move. After all, it might not have been me that got her like this. Suddenly her hips thrust into the air, bucking up and down, her legs shaking as an orgasm took her. The sight was amazing. After she had calmed, she sat on the edge of the bed, a look of disbelief, almost disgust ran across her face. “I...Can’t... He’s like my son”. Electricity zapped through my body, I’d done it, and she was mine.
When it came time to go home, rain was pouring outside, we were in the middle of winter, and the nights had become dark early. It was a 3 mile walk to my house through some woods. I was about to leave the house when a voice piped up from behind me, “Will, wait sweetie you can’t walk home through this” Debby had come running down the stairs, car keys in hand, she was always a good woman. “Are you sure Deb?” I implied, “I don’t want to be a fuss”.
“Don’t be silly of course it’s fine” she smiles at me, but there is something else there, guilt? Longing? I said goodbye to Tim, got in the car and we were off. 3 miles doesn’t take long in a car, but the quick way to my home was blocked by a crash, so we decided to go the long way, which would take us through the back roads. Debby was looking very red, more flushed than sweaty. Every time she checked her mirrors, I noticed a quick glance to my cock, this was my chance.
“Debby”? I said this in a playful; I want something voice, like you would when you ask your parents for money or something. “Yes... what’s wrong Hun”? She replies, with a quick smile. “Can we pull over? I really need to use the men’s room” I say with a giggle. “You animal” she says with a laugh “yeah ok, but be quick ok” she smiles again. We pull over in an overgrown lay by, I rush off and pretend to wee. When I get back in the car I leave my zip undone on purpose, and I know Debby has seen my erection nearly bursting through my underwear. At 17 my cock is 10 inches, and Debby is staring at it.
“If you want it Debby, take it” I say to her, I undo my top button. Her hand shoots over to stop me “Will, no please, what... are...” she is cut off, she has accidentally grabbed my cock, she can feel it in her hands, and her cheeks flush red hot, eyes widened with desperate longing. “It’s so big” she whispers. “It’s all yours” I reply and push my pants down, and kick them off. My cock is out, sprung to attention, staring Debby in the eye. The look on her face is as if she is in a trance, she grabs her skirt and panties by the hem line and pushes them off onto the floor. Her eyes fixed on my cock as she steps over and straddles me, she places my cock at her entrance, which is radiating with unimaginable heat, but she looks into my eyes at the last minute. “Will...We can’t, this is... this is wrong” She goes to move, but I grab her arse, “That’s what makes it so hot” I slam her down on to my cock, her tight pussy takes me by surprise and I let out a long moan. I see the shock and pleasure launch up Debby’s body, her mouth opens wide and she lets out a squeal as her eyes role back.
“FUCK!!” I’ve never heard Debby swear, her eyes lock with mine, and she has the look of a woman possessed. She begins to rotate her hips, clockwise, and then anti clockwise, she lifts her cardigan over her head and reveals no bra, just those perfect round breasts. She reaches back and lets her long black curly hair down, in this quick moment, she is a new woman. She begins to bounce back and forth on my cock, her breasts bouncing and jiggling with every impact. “Aw Yes!! Your cock feels fucking good” she squeals, the sound of wet smacking flesh fills the car. “Shit, Debby you’re so wet” I’m lost in passion, but I’m brought back to reality when she gets off me, I think she has changed her mind.
She has crawled into the back of the car; the seats can fold down, making a flat even surface. She lies on her back and beckons me between her legs. I come face to face with her, she guides my cock inside her again, and I begin to thrust, “Fuck me” she whispers, and I give a hard thrust, “Fuck me” another hard thrust, “FUCK ME” she squeals, and I begin to thrust hard and fast into her. I never thought the quiet hippy woman that I had known growing up was a closet whore. She moves her legs round my shoulders, and my balls smash against her arse. “That’s it you dirty boy” she purrs, “Treat me like I’m your dirty slut, and fuck me in the back of my car!!” The filth this woman is capable of baffles me, but I find it so hot, so sexy. Her body goes rigid her eyes go misty, her legs stiffen, and her hips buck as an orgasm rocks through her body “FUCK!! Don’t stop I’m Cumming!!”
I continue pounding her pussy, the orgasm won’t stop and my balls become drenched. The tightness of her pussy drives me insane. “Cum for me Will, fill me up, don’t pull out I want to feel every drop you have” the look on Debby’s face is priceless, she can’t tell whether to be disgusted with herself, or love every minute. “Shit, Debby I’m... aw!!” I shout loud as my balls empty wads of hot cum into Debby’s pussy, “Aw I can feel it!” Debby squeals in ecstasy.
I role off her, both panting, laid in the dark. “We don’t have to continue you know” I say to her, expecting her to break down at any moment. “Yes...Yes we do” she replies, I’m literally shocked. “I’ll show you everything, where the G-spots are, how to best get to them, and anything you ever want to try, I’m up for it.” The lust dripping from Debby’s words sends goose bumps over my body. “So if I wanted to try anal?” I say with a grin, “Even anal” she winks.
Debby was true to her word, she taught me everything I needed to know, which got me a lot of praise from Lauren in the bed room. I told Debby of how I prefer older women; she had asked if I wanted relationships with them, when I told her I just wanted sex, she said it would be a phase that would pass. I broke up with Lauren when she moved down south to go to college, we ended on good terms, which we wouldn’t have if she found out about Debby. I and Debby called it a day when I turned 20, I had been fucking other women by this point, but Tim had quit university to come home and get a job, so we found it hard to get the time.
My friends found out my attraction to older women when we were on a night out once, they were trying for the group of 19 year old lasses in the corner, and I had set my sights on a 40ish year old woman at the bar, I forget her name; it was a one night stand, but after I took her back to my University dorm room and fucked her stupid all night, my friends gave me the name milf hunter. I told them it sounded stupid and made me sound like a serial killer, so one of them decided to change it to Captain Cougar. I still hated it, but it was better than bloody milf hunter.
The lad that gave me the nickname, Milf hunter is called Wesley, he found it hilarious. I knew he wouldn’t if he found out I was longing for his mother Melissa. What a woman, 5’6, slender with long blonde hair, naturally lightly tanned skin, deep green eyes, average sized breasts with a tight little arse, she worked out a lot. She was 46 at the time, but looked 35, she was fantastic. They were a family from South Africa, Johannesburg I believe, the way she weaved her accent was stupidly sexy.
The main problem is that she was at the time, and still is now, married. So I had to take my time with her, plan it out. I had already planted the seed into her mind. We had all become close over that year at university, and Wesley had introduced me to his family. Melissa loved my energy instantly, how I was always happy, wanting to laugh and so on. She would always give me hugs. I hugged her from behind by surprise once; I did it for a laugh in front of friends, the reality was I had an erection, and used the same method as I did with Debby, with her.
She was flushed from feeling my cock, but I could tell she needed something else to get her to cheat on her husband. Wesley had a house party one summer afternoon, his sister Jen had come back from work over in Africa. She was an attractive woman, 26 years old at the time. She was between chubby and slender, but still sexy, a nice round arse, with large breasts, her mother’s blonde hair, and her father’s green eyes. She has 2 children; the father had left her before the first was born. She’s a well spoken woman, never swears, and never does anything abnormal. As the party went on I kept noticing her looking over at me, I smiled at her and she came over to talk. “Hi I’m Jen” she says with a smile. “I’m Will” I reply, returning the smile “It’s nice to finally meet you.” I add. Her accent is almost as sexy as her mothers.
“So are you the milf hunter” she says with a giggle, at this point I notice she is a tad drunk. I breathe out an annoyed sigh “I hate that nickname, but yes I’m him” she reads the disapproval in my tone, but ignores it. I notice Melissa head off inside the house and upstairs, as Wesley leaves to go get more drink from the shop, he would be gone for around half an hour. The music is loud, and suddenly I notice Jen was speaking the whole time. “What was that sorry? I was miles away” she looks at me with a strange look, then says again “Your the milf hunter, and I’m the milf, so hunt me” she winks then walks into the house, swinging her arse side to side, and heads upstairs.
A plan clicks to my head, if I fuck Jen while Melissa is upstairs and the music is as loud as it is; only she will hear it, which will make her think of my cock again, and show her I can use it. I felt bad about using Wesley’s sister like this, but I already wanted to fuck his mum, why stop there. I head off upstairs, I pass Melissa’s room where she is getting changed, and apparently from what I can tell someone spilt a drink on her. I walked into the bedroom next to hers, and Jen was laid on the bed naked already. I didn’t waste time either, my cock was hard from thinking about Melissa, and she would be dressed again soon, I also only had 20 minutes there about until Wesley got home. I flung my clothes off and walked to the bed, Jen got on all fours and crawled to me, taking my throbbing cock in her mouth and going to town, I could feel her tongue rubbing the underside of my shaft, this girl was a pro.
I pulled out of her mouth and swooped behind her, I wanted to face the door to see if Melissa would look in. “Eager aren’t we big boy” Jen purred, “Has it been a Wh...AW FUCK!!” Jen squeals as I shove myself to the hilt, she is tight, and soaking wet, she must have been thinking about this for a while. I pull her hair back and fuck her hard, I move my hips to reach the G-spots Debby showed me. “Shit you feel good” squeals Jen “Milf hunter indee...FUCKK!!!” she squeals as I hit the G-spot I wanted. I work magic with this woman, not a cougar obviously but I can’t do anything wrong, the boiling hot walls of her pussy undulate as if by command, from the head to the hilt.
She tightens around me as an orgasm erupts from her body “OH GOD!!! I’m Cumming!! You feel so good FFFUUCCKK!!” she smashes her arse back at me, meeting my every thrust, this girl is a pro. I notice movement at the door, I push Jen’s head on to the bed so she can’t see them... its Melissa.
She is looking me dead in the eye, a look of forbidden longing. She isn’t fazed by the fact she is watching a man fuck her daughter. I begin to reach the point of no return “Jen, I’m close babe” I manage to gasp. “I want to taste it please!” she begs. I pull out and she swings round on the bed and takes my whole cock in her mouth. She works her magic, her tongue doing wondrous things, but my eyes are still on Melissa. My balls tighten and I explode hot wads of cum down Jen’s throat, and she gobbles every drop. While Jen polishes my cock off I mouth to Melissa “You’re next” and blow her a kiss. She grows flustered, a faraway look in her eyes. I hear Wesley come in from the shops. I look down and Jen is smiling up at me “Just in time hmm big boy” she winks, kisses my cock and we get dressed. “We should do that again sometime” she says, a sly smile across her face “Oh you can count on it” I smile back; I might as well play along.
The party continues as normal after that. I keep catching Melissa looking over at me, I can tell she wants me, but she isn’t the only one. Across the room Jen and her friends keep looking over to, she must be telling them of our exploits. A couple seem uninterested, but I can tell some are tempted. As the day turns into night, and the party has reached full swing, Wesley decides we should all go to a night club in town. We call a mini bus to come pick us up, but before it arrives I learn Melissa isn’t going. I decide this to be my opportunity. I tell Wesley that I’ll catch them up in another taxi because I wasn’t feeling well. He jumps on the coach and I feel a quick squeeze on my arse, it’s Jen “Hurry along ok” she gives me a wink and bites her lip. Wesley’s dad jumps on last and they head off.
Melissa doesn’t know that I decided to stay back. I let myself in the house and close the door behind me, locking it quietly. Melissa comes round from the kitchen into the living room, when she sees me she jumps. “Will!! You silly boy, you scared the life out of me” she shouts, startled. “Sorry Mel, I just wanted to surprise you” I reply, I naughty smile stretching my lips. “Did you like what you saw earlier?” I take a step forward, she stays where she is. “I...Don’t know what you mean” she tries to throw the question away. “You know exactly what I mean, I know you saw me and Jen” straight to the point. “What you do with Jen is your own business” she replies, her voice begins to tremble as she moves towards me.
I pout “I put that show one for you though” the smile returns. We both stop in the middle of the room, inches from each other. “Will... I’m married, you’re my son’s best friend, and from what I can tell you are dating my daughter... this is wrong” our mouths move closer together, I brush her hair behind her ear. She is wearing a white ladies casual button up shirt, with short shorts, she is bare foot, and what I can tell through her top, she is wearing no bra. We kiss “I used Jen to turn you on, to make you want me” she tries to pull away, “That’s awful!” she falls into another kiss, our tongues doing a heated dance of passion. “You’re not the boy I thought you were” back into our heated kiss.
I undo her top to reveal her breasts, lovely round fleshy orbs, just a handful. I play with them, teasing her nipples. She begins to take sharp breaths. I stroke down her stomach and begin to undo her Shorts. I slide my hand down into her soaking panties, the heat close to an oven. The touch of my cold hands causes her to jump “You should sto...ahh...p” I slide 2 fingers in, she begins to lie back on the floor. I use my thumb to rub her clit, while 2 of my fingers work inside her pussy. “Oh god...Us...” she trails off, lost in passion. “What was that Mel?” I ask, kissing her neck. “Use Me” she whispers. “Can’t quite hear you” I pinch her clit and it sends a spasm up her body “Use Me...Use Me...USE ME!! I’m yours Will just take me!!”
She pushes her shorts off and kicks them away as I undo my pants. She pulls my shirt over my head and kisses my nipples as I pull my pants off, and my cock springs out to greet her “You’re so big” her eyes wide with passion and disbelief, she takes me into her mouth, lapping and slurping, surprisingly not as good as Jen in this case, she feels out of practice. She begins to get back in the swing of things, she feels fantastic “You taste good babe” she says between mouthfuls “Even better knowing Jen was on this earlier” I’m taken by surprise… did Melissa just admit she knows what Jen’s pussy tastes like?
For some strange reason, this sends me into hyper drive. I grab her wrists and pin her to the floor, she wraps her legs round my waste as I push myself inside her. She is the tightest cougar I’ve ever had; she can’t have had this for a long time. I begin to fuck this blonde bombshell hard. Her breasts bounce with every hard collision of our hips; my knees begin to get sore with friction burn, my balls slap against her arse “Oh god, you feel so good babe” her accent drives me wild “You feel amazing Mel” I manage to get through a gasp, this woman truly feels amazing. I grab her legs and lift them round my shoulders. I pound her pussy hard, rotating my hips looking for the deep G-spot at the back “Oh! Oh God!!... You’re so good at this… Oh god don’t stop” Melissa’s eyes role back, as if in and out of consciousness.
“Your cock feels so good…OH! There Right There Don’t Stop!!!!” She screams as I finally hit the g-spot. I fuck her as hard as a day is long. She begins to hit her hands against the floor, arch her back and pull at her hair. Her chest, neck and face begin to go deep red, flustered at the attention to her g-spot. Her pussy begins to flow with juices, which means one amazing fact, Melissa is a squirter. “You close Mel?” I ask her, she looks into my eyes and tries to focus on me, she calms her squealing enough to muster a simple response of “MmHm” then her body stiffens, her back arches, her head is thrown back as she screams into an earth shattering orgasm, her legs go stiff and spasm up my body, her toes curl going white hot before uncurling wide as if trying to separate from her feet “OHH GODD!! SHHIITT!!” Jet after hot jet of liquid squirts from her pussy, soaking me. My balls tighten, I suddenly reach the point of no return “oh god!! Mel I’m going to cum to!!” I shout “In me Will!! Fill me up!!” She is insistent, and I oblige. I pound her pussy hard, I’m mad with lust and my balls unload wads of cum into her pussy “Oh, Oh That’s good. I can feel it” she pants. We are both exhausted.
We lie there on the floor for almost 20 minutes before I turn to her and ask “What did you mean when you said about Jen before?” she looks me in the eye, her face still red and flustered, her body still has random spasms from her orgasm. “Jen is adopted Will” she finally replies “I told her when she was 18, I believed she was mature enough to know by this point, but I expected tears, not what she said next” she drifts off, a sort of fond reminiscing look goes over her face. “What did she say?” I ask. “She said she was happy I wasn’t her mother” she pauses “She saw that upset me, but she put her hand on mine and said, no Mel you have been good to me, and I don’t mean it like that. I remember her touching my face then saying, I’m glad you’re not my mum because now I can do this. Then she kissed me” I look at Mel shocked “She… Kissed you” I ask trying to believe it myself.
“Yes” she replied “I initially pulled away and asked what she was doing, but she grabbed me and kissed me again, and moved my hand she was holding under her skirt, she is stronger than she looks, but she wasn’t wearing panties, I felt her warm and moist… well you know, and before I knew it she was kissing my neck, and I was letting her” she pauses, a look of fond memory rather than self disgust on her face. “It’s like I had left my body and was watching myself do it, screaming to stop but I kept going. I’d begun to pleasure her, and she had slipped a hand under my dress and begun to play with me to. It felt so wrong, but it kept me going, I loved the whole taboo idea of it, I kept thinking, she’s not actually my daughter, I’m aloud to do this” she giggles and bites her lip.
“She had begun to say, I’ve been a naughty girl and need punishing Mel, please punish me, spank me, I deserve it” I was so turned on by the story my cock was erect, she looked over, noticed and straddled me, guiding it inside her “This will help me think” she says, gasping as my member enters her pussy. She slowly moves herself up and down my shaft and continues “I remember, she took her skirt off and grabbed her ankles, lifting them up, spank me she kept saying, and I did, hard” she began to move her hips back and forth, lifting to the tip, and as she said hard, slammed herself back down. It’s like she was telling the story with her hips.
“Spank me Mel, harder. That’s all she kept saying, and I did, I spanked her with one hand and poked her with the other. I remember looking at it, seeing how juicy it was, then I just remember going for it” she began to bounce on my cock fast and hard “I began to eat her out, I can still hear her squealing, Oh god yes Mel, don’t stop, don’t you dare” I grabbed her hips and met her thrusts “I couldn’t stop, I was lost in the moment, and then she squirted all OVER ME!!!” Melissa explodes into orgasm, taking me with her, I cum inside her again, and all I can feel is our juices mingled into one all over my waste. She lays on top of me face to face, both of us panting, recovering from another orgasm “And that Will, is how I know what Jen tastes like” she smiles, bites her lip, and kisses me.
We both got up after that, and had a shower, together obviously. I called a taxi after that and went to the club to meet Wesley and the rest. I managed to catch up being drunk with them and me and Jen would spend most of the night dancing and grinding against each other. I ended up leading her to the staff private toilet, I knew the bouncer so he always looked the other way. I had her bent over the sink when she said to me “So… was Mel as good as you hoped?” I looked at her and she shot me a smile back “Yeah she was” I replied, “Told me all about you” I smile and spank her arse hard “Ooff you tease” she winks “I have been a naughty girl with her a lot” she bites her lip as I pull out, pick her up and do her against the wall.
The affair between me and Melissa lasted a year. Somehow Wesley never found out about either me and Jen or me and Melissa. We never had a threesome, which I honestly regret, but I used to get videos sent to me over facebook, or on my phone of the 2 of them having sex. We only stopped because Jen had to go back to Africa to work, as she couldn’t find a job here, and Melissa and her husband moved down south. We rarely speak anymore which is understandable; it would have looked suspicious if we kept in contact. The last time I saw her was 10 months before this current event, when I was working a few weeks down south, and she would visit my hotel twice a week. We made a video for Jen and sent it to her, but we never heard a reply about it.
Now we are in modern day. I’m 24 years old and I work as a lifeguard at a local leisure centre. I’m lean, 6’1, but I still kept my rocker appearance. My friend Tim had come back to town for his birthday to see us and party old school. We met at mine for pre drinks “So Captain Cougar, you on the prowl tonight” Tim punches my arm with a bellowing laugh from him and the other lads “Hell Yeah, thought I’d start with your mum as a warm up then move on to the next feisty Lady” We all laugh, me most of all, as I had for a fact fucked Debby the day before while Tim was visiting his girlfriend, in Tim’s bed no less, I’d missed her, and she still had the moves, but we knew it would be a one off.
The drinks go down to easy and we head off to the local pub. Though I enjoy a night out, I had begun to lose interest in clubbing, so I would drink till last orders or before, then head home. We got to the pub and began to have the time of our lives. Wesley is out with us, and I learn Jen is back in town, and she hadn’t changed at all. “Hey Will” she smiles a broad smile and gives me a tight hug “Jen, it’s been way to long” I return the hug, and she slyly licks my ear while no one is looking “Much to long” she bites her lip and walks away. Jen hasn’t changed at all. She is wearing a crème dress that stops halfway between knee and hip, long enough so it manages to conceal her plump arse, but short enough to keep you interested, her back is revealed in the dress, showing down to just above her bum and the front reveals a nice eyeful of cleavage. Her high heel shoes match her dress with color.
11:30pm and the shots come raining in, we say cheers to Tim and down them all. I notice Jen head into the toilets; she gives me a quick wiggle of her arse across the room and vanishes into the men’s room. The camera outside has been broken for years, so she can get away with things like that. I follow her in and find her in the end cubicle, the only one where you can’t see under the door or wall, or look over, like its own separate room. She is just stood there looking at me, she lifts her arms up to the straps of her dress and pulls them down, revealing her gorgeous round breasts.
I walk in and close the door behind me, locking it. Her eyes half glazed, goose bumps going up her body with hot excitement “I heard you saw my mum a few months ago while in London” she says while biting her lip “Yeah I did” I run my hands up her arms “We had a good catch up, did you enjoy our video?” I turn her round and bend her over slightly, her face is pressed gently against the wall, one of her legs is lifted onto the toilet as I rub my fingers up the back of her thigh and up under her dress, lifting it as I went.
“Aww…” she purrs at me touch “I was so jealous, I’ve wanted you for so long Ah!... Aww” I slide 2 fingers inside her pussy “You did something with her in that video we had never done” her voice has become nearly a whisper, as if in a trance “What was that?” I ask, she moves her head slightly to look back at me “You fucked her in her arse, I’ve wanted that cock in my arse ever since. Go in… Shit!...” she has a quick spasm of pleasure hit her body “That felt good, go in my bag, there is lube” I stop fingering her and rummage through her bag, she takes her panties off and resumes her original position. I find the little bottle and lift her dress over her arse, and pour the lube over her arse hole.
“Oh, it’s cold” she giggles “Be gentle babe, I’ve never had a cock in my arse before, and you are pretty big” she bites her lip and smiles back at me “I’ll go gentle, I promise” she knows I’m lying. I place my cock at her arse hole and begin to push in, I can tell it’s painful for her, but she is enjoying it “Shit!..FFFUCKK! oh that feels good” I keep pushing, her arse enveloping my cock, inch by inch, and after 2 minutes of easing myself in, I’m at the hilt “Oh god, this feels amazing” Jen’s mouth is wide open, her eyes tight shut, I decide she has had enough time to adjust, I pull all the way out, and slam back in and begin to fuck her hard “AH!! OH GOD!! THAT FEELS GOOD BABE YES!!” she screams and shouts, lost in this new sensation “Shh, quiet babe, don’t want anyone to hear us” I grab her hips and fuck her tiny arse hole as she covers her mouth “Shit… Shit this hurts so good” tears begin to run down her face, thank god for water proof make up.
“Do you want me to pull out?” I ask concerned “Fuck no” she smiles back “I’m loving this” I smile and put one hand on the wall for leverage and reach round with the other to fondle her clit, I know we have to be quick, otherwise people will become suspicious. “We should…” she trails off, holding back a scream “Grab my phone, lets film it and send it to Mel” she drags her bag over to her and grabs her phone, she sets it up and starts filming herself “Hi Mel..Fuck! aww guess who I’m with, say hi Will” she turns the phone onto me “Hi Mel, miss you babe” I spank Jen’s arse and blow Mel a kiss to the phone.
“We thought we would give you something to watch, enjoy” Jen passes me the phone and a film me fucking her arse while Jen plays with her clit. “Will I’m close, I’m so close” Jen gasps “Me to Babe… Together?” I ask “Toge…Aw Aw Aw AWW!! SHI….mmm” I cover her mouth as she meets my thrusts, our hips colliding with the force of crashing cars as she explodes all over the cubicle floor “FFUUCCK!!!” I’m not far behind as I shoot ropes of hot cum into Jen’s arse, our orgasms nearly taking us off our feet. I pull out and get close with Jen “Hope you enjoy Mel” We blow a kiss then end the video. We straighten ourselves up and leave the bathroom separately. When I asked where I had been, I just said I had been with an old flame, “Captain Cougar strikes again!” Tim joked.
Jen sent the video via message on her phone to Mel, titled “Watch Alone!!” Me and Jen managed to stay off until the end of the night. I got a quick prod in the ribs at around 1:30am off Jen, she waved that she had a video message on her phone. “Will, you wouldn’t mind walking me home would you, I’m a little drunk” she giggles “Sure yeah” I reply “Let’s go” I tell the lads that I would walk her home, then get a taxi from her house to mine. We all hug good night then head off. We giggle and reminisce about old times, the private ones we couldn’t talk about in front of people. Wesley went home around 12 not feeling well, so we cut into a place called black alley on the sea front, a sheltered seating area that over looked the sea at the top of the hill. It was quite far off the path and the sea would drown out any sounds we made.
I sit on the bench, and Jen sits on my lap “Ready to see what she sent” Jen giggles “Yeah” I reply with a smile. The video starts and we see the video of us on the big TV in the background, this isn’t a phone video, the video is made on an actual camera. Melissa wanders from behind it, she is completely naked, and again hasn’t changed at all “Hey kids” she says with a smile “Jen, your dad is out at work tonight, so I thought I’d show you how much I like this video you sent me” she winks, blows a kiss at the camera, and she starts our video on the TV “oh and Jen baby, get that big cock inside you, ride along with me babe” I’m hard already from seeing Melissa. We stand up, I take my pants off and put them on the seat so I don’t get a cold arse, and Jen takes her panties off. I sit back down and put my cock at Jens pussy as she sits down on it.
“Aw that feels good” Jen purrs. Melissa begins to play with herself to the video we send her, and Jen rides my cock as we watch it. Melissa speaks “Oh… Fuck, I wish you 2 were here” she says breathlessly “Will I want your cock so bad, pounding inside me. And Jen I want you sat on my face, l can still taste you” Me and Jen are mesmerized by Melissa “Oh god, She’s so naughty” gasps Jen, she bounces on my cock so hard her breasts are bouncing and slapping, I meet her every bounce with a hard thrust, she somehow keeps steady hold of the phone, we are both fixated on Melissa.
“Oh god, I’m close guys, try and cum with me” Melissa’s back begins to arch, and me and Jen go into over drive “We have to cum with her!” I shout “Oh god yes Will! Fuck me!! Make me cum with her!” the bench squeaks and creaks with our passionate Endeavour. Melissa’s head whips back as she cums in the video, and at the same time, me and Jen cum “Fuck Fuck!! I’m Cumming!!” squeals Jen “Oh Fuck me to!!” I follow up. I grab her shoulders and fill her up, every drop inside Jen’s pussy, Melissa squeals and bucks on the video. Me and Jen sit there, I hold my arms round her waste so she doesn’t fall off, we are gasping for breath, recovering from orgasm. Melissa is curled up in the video.
She roles over and blows us a kiss then says “Miss you guys” then turns off the camera. I walk Jen home, when we get to her front door, she turns and puts her arms round my shoulders “I’ve missed you Will” she smiles and kisses me “I’ve missed you to Babe” I find that I do mean it, I have feelings for this woman. She walks inside, and closes the door, shooting me a cheeky smile beforehand. Jen becomes my frequent friend with benefits after that night, I find out she is permanently moving back to the area and is only staying with Wesley while she finds a place of her own.
She moves into a house that is a former farm house about 20 minutes outside of town, and I’m pretty much there every day. I usually start work at 12 in the afternoon, after she would drop her kids off at school, she would find me parked at her house where we would go and have sex and hang out for a few hours before I went to work. I found myself falling for Jen, but at the same time, there was something eating away at me and that something was stopping me from making us official and more than just sex. I could tell Jen was ready to become official, but that something was pulling me back, like unfinished business.
One night all the lads went out for drinks, when we got to the pub I found out that I had completely forgotten my wallet. I told them I would be back soon and walked back to Wesley’s where I had left it. I could have got a lift but I just fancied a nice walk, I wasn’t too bothered about getting drunk anyway. After half an hour I got to Wesley’s, grabbed my wallet and headed back. Listening to my Ipod seemed to make me walk faster, and being a fan of Metal, well I could walk pretty fast if lost in the music. For a moment I think I can hear someone shouting my name but pass it off as music, until a hand grabs my shoulder spinning me round to see a woman standing before me.
“Will, is that you?” she knows my name, but how. I take a closer look at the woman, she is familiar. She is wearing a black top that shows off her cleavage and revealing a toned stomach. She is wearing black leggings that cover slender legs and a round firm arse, and on her feet she wears high heeled shoes. Her hair is short and blonde with a side fringe. The revelation dawns on me “Oh my god Diane!” I hug her hard and we laugh and giggle.
“It’s been way to long” I say “Where are you staying?” the smile on my face begins to hurt; I’m overjoyed to see this woman. “Here… I live here” she points to the flat “I live on the top floor, would you like to come in and catch up?” The smile on her face is hard to say no to “Of course, lead the way”. I follow her upstairs; her arse is still as nice as I remember. Her face in the light shows she hasn’t aged much at all, the woman is 50, but doesn’t look a day over 40. “Take a seat, I’ll bring some wine in and we can talk” she heads off to the kitchen and grabs a couple of bottles. I learn that after she moved away she met a man and got married, but she had begun to miss the freedom of being single, so she left him last year, and moved back into the area.
“He never liked my dress sense that man. Always said I was revealing too much, but you know me hunny, I’ve always dressed like this” she said. “Yeah you have like” I laugh “You never did leave much to the imagination” we both laugh together “Cheeky bastard” she slaps my arm “But no you are right I never was one for being shy” she sends me a foxy smile, and my boner begins to rise. I take a sip of wine and try to calm myself.
“Anyway, as I recall, you liked what I wore… a lot” I go red and look at her; she has a very sly smile on her face “Oh yeah?” I reply “What makes you say that?” my body begins to shake. She takes a sip of wine and places her hand on my leg “You think I didn’t know you wanted me back then? I remember catching you in my bedroom masturbating into a pair of my knickers” she does a very sexy giggle and slides her hand up to my boner but I’m still lost for words, her direct approach blind sides me.
“Oh... There he is” she smiles broadly then bites her lip “You… you saw me do that?” I’m trembling “Don’t be scared sweetie” she coos “You were young and horny, your hormones all over the place, I didn’t blame you, in all honesty I was flattered. A young lad finding me attractive enough to cop off to is fine by me” she edges closer to me, and begins to rub my boner through my jeans, I begin to lose control. Diane looks me dead in the eye “Do you think I’m still sex… mmm” I grab her and pull her into a kiss.
She returns it and our tongues dance a heated tango of passion, she pushes me back on to the sofa “Sweetie, I didn’t invite you up here to kiss” she takes her top off revealing those perfect round breasts, firm and no droop in sight. Then she turns round and takes her leggings off, bending over and revealing her round tight and firm arse, and her hairless pussy. She comes over to me, swinging her hips from side to side. She undoes my pants and yanks them off, letting my throbbing cock spring free, as I remove my shirt. “That’s what I invited you up here for” she takes my cock in her hand and begins to work it up and down, I’m lost to this woman.
“Ever since I saw you jerk off into my favourite panties I’ve thought of nothing but having this huge cock inside me” she gives it a lick from hilt to head then back down, and pulls away. “I didn’t want you then obviously, much too young, I knew I had to wait. And I’m glad I did, look at you, all grown up” every dream of my puberty was coming true, I was about to fuck Diane. “You’re so sexy Di, oh god I’ve dreamed of this day” I’m practically whispering, Diane is a pro at working my cock, teasing me with her hands and tongue. She licks up my cock again then when she gets to the top, takes it into her mouth, burying my cock down her throat.
The sensation is driving me insane; she is such a perfect tease. She holds her head there for half a minute before coming up for air. “You taste good hunny” she smiles, pre cum dribbles down her lip “Every man I have been with, the only thing that got me through was imagining their cock was yours. Every time a man came inside me, or on my face I imagined it was yours” she took another 3 big blows of my cock, then she leant back, letting go of it. “You do look good hun... Whoa!!!” she is taken by surprise as I leap from the couch and lay her on the floor, as she lays back I part her legs and go to town eating out her pussy, all tongue and fingers “SHIT!! FUCK!! OH GOD YES WILL BABY THAT’S GOOD!!!”
I fuck her pussy with my tongue and fingers, hooking them and pinching her clit. Before I know it I have 3 fingers inside her and I’m nibbling her clit. She is holding the back of my head squealing in the background somewhere, but I’m lost in concentration. The taste, the aroma, she is intoxicating, addictive like a drug that I can’t help but take. Her hips buck “FUCK!! Will... I’m... I’M... AH FUCK!!!” she squirts all over my face, a never ending jet of hot liquid coating me, her and the carpet. She lays there twitching violently as the orgasm rocks her body. I kiss up her body to her lips, we engage in another passionate dance of the tongues. She breaks the kiss “Give me it... Give me your cock... I need it” she looks longingly into my eyes as she reaches down and grasps my throbbing member.
She rubs it up and down her pussy, and begins to guide it in “Shit... Di it’s yours... It’s all yours” I push in with her guidance and my cock is enveloped by the very pussy that made me who I was, that made me want to fuck all these older women, which made me Captain Cougar. I hoist her legs round my shoulders and begin to thrust in and out, slowly, savouring the moment I had waited over 10 years for. I knew Di, she was a slut through and through, I could only imagine the amount of cocks she had ridden, yet she was tighter than a virgin. Even with her pussy so drenched and lubed up with her juices, it was still incredibly tight. I get used to it, and begin to pick up the pace “Oh God... you’re so big” Diane purrs to me. She puts her hands round the back of my head and pulls me in for a kiss.
Her hold is tight; I use my strength and stand up, managing to keep myself inside her, keeping her legs round my shoulders. “Oh you’re so strong” Di winks and kisses me “Fuck me against the wall” I press her against the wall and begin to pump her pussy so hard my balls lift up and smack her arse with every thrust, her breasts bounce with every connection of our hips “Fuck!! Yeah that’s it babe... Fuck me... Fuck me!!!” the ornaments on the shelf nearby bounce and rattle with the impacts of our passion. “SHIT SHIT I’M CUMMING!!!” Di explodes again, drenching my balls and down my legs, the feeling of her pussy becoming even tighter nearly knocks me off my feet.
“Fuck put me down Will I can’t take it” her eyes are rolling back into her head; I take her to the sofa and lay her down. She spasms and twitches violently. Her hands holding her pussy, her legs clamped tight round them. Diane’s body is covered in goose bumps, her toes curled tight and turning white. “Fuck it won’t stop... Aw” she fights to control herself. After a few minutes she becomes reasonably calmed “Shit Will that was amazing” She laughs jumps up and throws her arms round me and into another deep kiss. “You ready to continue, I’m gagging to be inside you again” I shoot her a sly smile “Bedroom... Now Mr” she grabs my cock and leads me into the hallway, upstairs, and into her bedroom.
“Close your eyes babe” I do as I’m told. I hear her rummaging round for what seems and eternity until I hear a strict “AHEM” I open my eyes to see her stood holding 2 pairs of handcuffs in one hand and a wooden paddle in the other. “What are they for?” I become a little nervous “For me” she replies, a look of seriousness on her face. “I’ve been so... so naughty, and you have to punish me” she goes over to the bed, a pull up bar is quite high above the bed post. Almost by instinct I follow and handcuff her to the bar. She is knelt down but her arms hoisted into the air, she is able to stand. She stands up and bends over, sticking her arse out for me “Punish me Will” I stay still. I just stand quietly like an idiot. “Spank me... hard... punish me...” I swing the paddle at her arse, a loud smacking noise fills the room and she yelps.
“OW!! Yes that’s it... again” I spank her again “OW!! Oh god yes... Punish me... I’m so naughty” I spank her 3 times hard in a row, her knees buckle slightly, then she readjusts her stance “Oh... Oh god... I’ve been so naughty... I’ve longed for your cock for so long... I’m a naughty slut and I want you to fuck me!!” I throw the paddle down and lay down between her legs, she lowers herself down and I guide myself inside. “Fuck yes that’s it... I’m yours Will... Do what you want I’m your naughty fuck toy” Diane is exactly what I thought she would be in bed, a grade A no nonsense slut with a one track mind. She rotates her hips on my cock, and then slides back and forth, she moves as if she was 20 years younger.
She bounces on my cock, using the force of me thrusting up at her for a higher bounce and deeper impact, we are perfectly in sink. The room is filled with the sounds of Diane screaming in passion, the wet slurping sounds of my cock entering and leaving her pussy and flesh smacking against flesh. “Will... top draw next to you” I look over and reach for the draw, I open it to find a dildo. Suddenly Di stands up and straddles my face. I am overtaken by the hot moistness of her pussy. “Eat my pussy Will... Eat my pussy and fuck my arse with that dildo” I jam the dildo into her arse; I don’t bother easing it in. “FUCK!!! Oh god yes!!! Treat me like the slut I am!!” I lap and slurp at her pussy, the taste of our mixed juices is divine.
I shove the dildo in and out of her arse, treating her like nothing more than an object to satisfy my needs. “FUCK FUCK FUCK!!!!” she explodes over my face again, her juices cascading down my body. I slide from under her and position myself behind her. “Is it your turn to cum?” she pants and throws me a weak smile “You’re damn right” I grab her hair and pull as I shove the full length of my cock inside her. “SHIT!! Yes that’s it, fuck me, fill me up with your cum!!” I pummel her pussy with my cock, I wrench her back by her hair with one hand while playing with her clit with the other... then I feel it. As Diane begins to tighten again, so do my balls “Di... I’m” she cuts me off “Do it with me, fill my pussy up... fill it up... FILL IT..... AH!!!” she hits orgasm again, her tightness starting at the head of my cock, and working its way down, causing me to explode inside her. “FUCK DI I’M CUMMING!!!” ropes after rope of hot cum hits the back of her pussy “I CAN FEEL IT!!!” Diane pushes her arse back on to my cock hard, I hold her hips so she doesn’t lose a single drop.
We stay fixed in that position, panting and gasping for air. My vision becomes less fuzzy, I look round the room. I notice the clock; I left the pub nearly 3 hours ago!!! I find the key and Un cuff Diane. She sags limp to the bed. “That... That was amazing” She can barely speak. “You weren’t too bad yourself” I shoot her a sly smile, with a limp arm she gives me a weak slap. “What a send off you have given me you young stud” I look confused at her “What do you mean send off?” she sits up on the bed and lights a cigarette. “What have you noticed about my house? About me? Something I’m wearing perhaps” I look round the room and notice photographs on the bedside table. “This... Isn’t your house?” I ask confused “Got it” She smiles “This is my sister’s house, she was letting me stay here while I sorted things”
That’s when I notice it “Your ring... You’re still married?” a weak smile goes across her face “Yep... You got it hunny, we have just managed to work things out me and him. I was just heading out to enjoy my last night as a single lady when I saw you.” I blush, and as does she “I couldn't pass that chance up, to fuck the young stud I’d thought of for so long” she leans over and kisses me “Thank you for making me feel 10 years younger again”.
We both shower and get dressed. I found out Diane was moving the next day to be back with her husband. As I kissed her goodbye, I didn't feel sadness. I lay in bed that night, thinking hard, something was new. As the days after mine and Diane’s encounter rolled by I began to realise something. I began to show affection for Jen, I made it public we were going out with each other, I showed my affections in public rather than a dark secret affair. Diane was my unfinished business, my end game. All my lust for cougars ended where it began, with her.
I sat and talked with Jen one night, we talked for hours and we decided it was just us from then on, no more Melissa, no more sleeping around; it would be me and her. We are still together to this day, living happily in her house outside of town. If you had asked me the year before if I thought my lust for Cougars would be gone by this time a year later, I’d have thought you mad. It’s funny how life plays out
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This is Captain Cougar... Signing off
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