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Jenny Pegged. All characters are fictional and over 18.


Guest pemilfton
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Guest pemilfton
What can I say about my big sister Cath? She's 35 years old and five years my senior. At 5' 5" tall and 112 pounds she is deliciously well formed with a perfectly rounded and proportioned figure apart from her breasts which are large and always make her lean forward slightly with their weight. She has long straight dark hair that is parted in the middle and always seems to curl seductively into her cleavage which she nearly always has on full display. Her eyes are green and piercing and her smile wide and bright making her slightly long nose wrinkle a little. Facially she is no stunner with slightly heavy features and that long nose but her infectious smile, twinkling green eyes, devilish dark hair and voluptuous figure are enough to hypnotise any man.

 

No wonder then that I have always fancied her terribly and harboured many, many wild and dark sexual fantasies about her. When I was 18 I caught sight of her large protruding, pink breasts one day when I passed her room and I spent the next few weeks masturbating myself furiously to the thought of those breasts and her long dark hair falling between them covered in my cum. I was racked with guilt at having such thoughts about my own sister but that seemed to make it even more dirty and daring. More exciting. I wanted to touch her. Fuck her. Suck on her. Cum on her. I wanted it so bad. But of course reality was, as ever, a boring smack in the face and before long Cath left home to live with some lucky bastard of a guy.

 

Years later and here I am 30 years old and still lusting after my sexy big sis despite having a failed marriage myself and a string of failed relationships. Cath too had never found Mr Right with the guy she left home to live with turning out to be a no hoper. So we both lived in our own little apartments on opposite sides of the town. We both had boring jobs and boring lives and it seemed to me that my life was going nowhere fast. Cath and I met up at least once a month usually at her apartment as mine was more often than not a complete mess!. Hers, in contrast, was always neat and tidy. And she had cable TV! So we often met there if neither of us were doing anything on a Friday or Saturday night just to talk and goof off as we had always done. Cath was a very open and honest girl and would talk quite openly about her boyfriends to me. 

 

I'm not sure if she ever realised how much that made me feel like shit but I, of course, could never give away how jealous I was of her boyfriends. Sometimes she would go into a little detail about her sex life with them but I almost always changed the subject. Despite her advancing years Cath was still gorgeous and had never really changed. She was a little more rounded and her face wrinkled more when she smiled. And of course her hair color was no longer natural but came out of a bottle. But she was still the same, sexy, scrumptious big titted, petite, ball of fun she had always been and I still wanted her as much as I ever had done.

 

One Friday night Cath and I were sitting talking after demolishing a Chinese takeaway and a bottle of red. We chatted about the usual boring stuff and eventually the conversation turned to our respective sex lives. Which as it turned out was a non subject for us both. Neither of us had had partners for some time now.

 

"We're both past it little brother!" Cath said swinging her legs up onto the sofa she sat on opposite me. She pulled her ankles into herself and shifted her body a little as if to get more comfortable and as she did I couldn't help but notice her breasts jiggled under her white t-shirt. She was wearing a bra under her tight t-shirt but still her tits seemed to have a life of their own.

 

"Speak for yourself!" I said taking a swig of my wine. "I'm only 30 sis you've got five years on me! There's plenty life left in me yet!"

 

"Jesus Christ Tom we're only in our thirties you'd think we were old farts the way we're talking! I guess we've both just been unlucky in love and all that shit!" Cath said as she put her wine down on the low coffee table in front of her and then rested her face against her right palm. She gave me a wry smile then suddenly lifted herself up into a kneeling position on the sofa. Cath was always fidgety and could never keep still and she knelt there now with her arms down either side of her with her palms flat on the sofa, leaning forward slightly and giving me a hell of a view of her amazing cleavage. Her long dark hair fell forward casting a shadow over her breasts and face which made her look absolutely stunning. 

 

She sat there still for a moment and I had to look away and reach for my wine once more. Cath adjusted her position again and sat normally on her sofa now and crossed her legs. She had tight jeans on but bare feet and I noticed now that her toenails were painted black just like fingernails. She leant back and sat deeper into the sofa making her hair fall against the mounds of her breasts where it curled into her cleavage. My pulse was beginning to rise as it always did when I sat with Cath like this. Her constant fidgeting and moving around was very distracting and made me notice how incredibly sexy she was all the more.

 

"This'll 'probly embarrass you Paul... " Cath said sitting forward once again placing her hands between her thighs. "But... umm... you look at much porn?" she asked with a slight shrug of her shoulders and tilt of her head.

 

I froze. It wasn't a question I was expecting and stared at her a moment. She just smiled softly and sat back again and crossed her legs folding her hands in her lap.

 

"Umm... pffff... well... " I responded and shrugged my shoulders. I put my empty glass on the table and gave her another shrug and a smile. "I'm a guy. What can I say?" I eventually said trying to sound calm and cool about it.

 

Cath giggled. "Course you do!" She said softly and pulled her hair back behind her left ear with her hand before taking a sip of her wine. "What do you like to look at?"

 

Her bluntness caught me off guard a little and I could only laugh at her as if she was just messing around. "Like I'm gonna tell my big sister!" I said laughingly.

 

"Aww... c'mon!" she said with a slight pout. "Spill the beans bro! You like big boobs and stuff I guess right?"

 

I looked down at my hands which I was now starting to wring together a little nervously due to feeling a bit embarrassed. "Well... yeah... sure... umm... ya know... " I struggled to say and had to cough to clear my throat. "Jeez Cath shutup!" I said with an attempt at a laugh.

 

Cath leaned forward and looked at me from under her eyebrows. Her hair fell forward into her lap. Christ she looked fucking hot. "I bet you're a right perv!" she said almost in a husky whisper then giggled. "Sorry little brother I'm just teasing" she said and sat back again and smiled. "I shouldn't talk about this it's embarrassing you!"

 

"Well... yeah. Kinda!" I said. "You're right though" I said sitting back and trying to relax. "I am a perv!" I said and grinned at her. She smiled back at me and shrugged her shoulders slightly and screwed her nose up briefly then just looked at me saying nothing. I suddenly felt an inexplicable rush of bravery, or stupidity! But almost uncontrollably I blurted out "I love looking at all sorts of pervy stuff actually. The dirtier the better." I tried to look her in the eyes as I said this but I looked down at the table and my empty glass. There was silence and I suddenly felt incredibly awkward and self-conscious. 

 

After what seemed a long awkward silence Cath simply said. "Such as?" I looked up at her and she was playing wither hair casually and didn't seem hugely bothered by what I'd said. I decided to see if I could shock her with the plan that if she freaked I could just say I was winding her up.

 

"Well I love watching guys being fucked by big boobed girls with strapons." I said flatly and looked her in the eye to watch her reaction. I saw her eyes widen then suddenly she burst out laughing!

 

"Holy shit Paul! Hahahaha... oh good god!" she laughed and gasped sitting bolt upright. "Are you serious? I mean... is that like something you would want to do?... or... I mean... have done... or... Jeez!" She said and giggled again raising her hand to her mouth.

 

I just grinned at her as her reaction did nothing to deter me. "Well... no I haven't but... well... yeah shit I'd love to have a big boobed girl bang my butt. Especially with me on my back so I could see her and cum on her!"

 

"PAUL!!" Cath almost screamed! "Holy crap!" And then giggled. "You're crazy! Hey I should get you and Jenny together she's into crazy shit I'm sure she'd oblige you!"

 

"Jenny?" I replied questioningly. Jenny was one of her friends and I'd met her a few times. A somewhat plump girl with blonde shoulder length hair and a pretty face. Her boobs were enormous!

 

"You mean... big Jenny?" I said smiling and gesturing with my hands to my chest.

 

"Yeah BIG Jenny!" Cath replied smiling. She's crazy when it comes to sex I'm sure she'd love to do that sort of thing to you. Seriously!"

 

"Really? No way! But Jenny always seems quiet?" I said which was true. The times I'd met her she wasn't very talkative and seemed shy and a little lifeless.

 

"Don't be fooled!" Cath scoffed. "She may not look it but she uses those jugs to good effect you know. Guys and girls she's not fussed."

 

"Really? Wow!" I said genuinely surprised.

 

"Actually... " Cath began suddenly looking more serious. "I... um... well... look you promise to keep this to yourself?"

 

"Uhh... sure!" I replied with sudden curiosity.

 

"Look... um... I'm totally straight you know. I'm only interested in guys. But... well... " she fidgeted and repositioned herself into a kneeling position on her sofa. "Me and Jen... we... well... we sometimes... do stuff" Cath said looking at me somewhat sheepishly.

 

My mind was genuinely shocked at what Cath was telling me but I decided the best response here was to be totally cool. So I just stuck my bottom lip out briefly and shrugged. "No big deal sis. Although c'mon what d'ya mean by 'stuff'"? I added leaning forward with genuine interest.

 

"Shit!" Cath replied. "Well you know... we... well... we get each other off sometimes. Just kinda friendly fun for kicks really."

 

"Yeah OK but WHAT do you guys actually do?" I asked grinning.

 

"Like I bet you'd love to know huh?" Cath replied. "Aint telling! All I'm saying is Jen is seriously up for just about anything. I'm serious. If you want me to ask if she'd... you know... screw you up your shitter I'll ask her. I'm 100% certain she'll jump at the chance. I know she's a bit of a big girl and no supermodel but... "

 

"Hey!" I interrupted. "Jen's pretty sexy really. I mean her tits are fucking huge! Damn you really think she'd do it?"

 

Cath grinned at me and leant forward. "I'm positive. I'll ask her. And yeah. Her tits are fucking huge just you wait. Her nipples are like cigar butts!" 

 

We both laughed. I sat there stunned at how this conversation had turned out. I'd known Jenny for about five years and she'd never come up in conversations between me and Cath before. We talked some more about her and I quizzed Cath for more details about what she got up to with her friend but she refused to divulge any details. Soon the conversation turned to other things and eventually it was time for me to leave.

 

"You sure you want me to speak to Jen?" Cath said as I was about to leave.

 

"Definitely!" I said raising my eyebrows and grinning. "Please do and let me know what she says!"

 

Cath sniggered. "Will do little brother. Catch ya soon OK?" she said and gave me a playful poke in the ribs.

 

A few days passed and then I received a text from Cath. "Hey bro spoke to Jen she's ordered one and is gonna bum you bad! Lol"

 

I was a little taken aback and stuck for what to say in reply at first. I just said "Cool. You gonna give her my number?"

 

"No. She wants to meet you in my flat when she's got it. Will let you know asap. PERV!! Lol"

 

I paused and then grinning to myself typed "Hope she remembered lube! ;)"

 

"Yuk!" she replied.

 

Three days passed then on the Friday I got a text from Cath. "Hey bro! Jen coming to my place tomorrow night with her new toy. 7:00pm ;)))"

 

"OK will be there. Hey are you going out?"

 

"Not planning to"

 

This made me think all sorts. Cath was going to be there when Jen was going to do this? Then I got another text. "Jen wants me there. I think she wants to play with me too ;))"

 

My mind raced. "Holy crap!" I replied. "OK I will be there sharp!"

 

"PERVERT!! :D" Cath replied. I sent a quick "lol" and put my phone away. Life was suddenly very exciting!

 

The next evening I arrived at Cath's place bang on 7:00pm. Cath greeted me at the door wearing a white t shirt and denim shorts. Her hair looked as if it had been straightened and was long, sleek, silky and mesmerizingly gorgeous.

 

"Hey Paul!" she said cheerfully then whispered... "She's in the lounge!" I looked at her and smiled feeling somewhat nervous and a little embarrassed. But I made my way to the lounge and there was Jenny sitting on the sofa.

 

I stood there a little stunned at her as she was sitting quite casually on the sofa wearing a tight dark red top that was very low cut. Her cleavage was a sight to savour as her breasts were bulging. Her hair was immaculately styled and a little longer than when I had last seen her. She wore tight fitting, calf length black leggings and was barefoot. Her eyes were heavily made up with dark eyeliner and her lips were bright red. I'd never seen her look so sluttish she had always seemed quite a plain, plumpish girl. Although a little overweight her body was well proportioned and the size of her breasts made up for any slight oversize elsewhere.

 

She smiled at me as I stood there somewhat transfixed. "Hey there Paul!" She said crossing her legs and leaning forward slightly with her arms either side of her. Her breasts bulged even more and her hair dropped off her shoulder. She smiled at me so seductively I felt my cock begin to swell.

 

"Hi Jenny!" I said in return trying to sound calm and collected.

 

"Jenny has her toy with her!" I heard Cath's voice say from behind me. I looked at Jenny in the eyes and she simply smiled and then screwed her lips a little.

 

"Sure have. I hear you wanna be butt fucked!" Jenny said looking at me with a cheeky, enquiring look. Behind me Cath giggled. I turned around and saw Cath standing there with her hand over her mouth to stifle her giggles.

 

I looked back at Jenny. "Umm... yeah... I... well... yeah I do!"

 

"Good!". She replied. "And you're about to be aint he Cath?"

 

"You go to it Jen!" Cath replied.

 

Jenny stood up and stepped towards me. She stood so close her tits were touching my chest. She looked at me expressionless for a few seconds, her eyes darting back and forth between my own then suddenly grabbed the back of my head and pulled me to her and kissed me hard on the lips. Her tongue slide forcefully into my mouth and she sucked hard on me pulling my tongue eagerly into her mouth. I made a slight noise in my throat through sheer surprise at the ferocity of her kiss before she broke off and took a step back.

 

"Take a shower!" Jenny said sternly. "Then come to Cath's bedroom. And don't be long!" 

 

I looked at her a second and then at Cath who was standing there looking a little embarrassed with a wide eyed grin. She nodded at me to go. I left the room and went down the hall to Cath's bathroom and hurriedly stripped, showered and wrapped a towel around my waist. Before I left I looked briefly at myself in the slightly steamed up bathroom mirror. "Holy fuck!" I muttered to myself. I could feel my cock was already semi erect and beginning to ooze pre-cum.

 

I left the bathroom and padded lightly with the towel around me to Cath's room. I expected to see Jenny there and there she was. Standing by the bed wearing a black bra and panties. Her tits were almost spilling out from her bra. But I was shocked to see Cath kneeling in front of her and sucking on the flesh coloured strapon dildo that Jenny was also now wearing!

 

"Jesus fuck!" was all I could say as I gawped at my sister sucking on Jenny's appendage. My cock hardened.

 

Cath stopped what she was doing and looked around at me. "Sorry Paul just couldn't resist!" she said smiling and gave the dildo a wiggle. "All yours now bro!"

 

"He's all mine you mean!" said Jenny. "Lay on the bed fucker! Face up. I want you to see me fuck you!"

 

"OK" I said suddenly feeling apprehensive and a little self-conscious in front of Cath of the bulge under my towel. I sat on the bed and looked at Cath who was just standing there. "Umm... you... um... I think we'll be fine now!" I said to suggest Cath left the room.

 

Cath smiled at me oddly then looked at Jenny who firmly pushed me back so I lay on the bed. "Guess what fucker? Your big sis wants to watch! Adds to the fun dontcha think?"

 

I looked up at Cath who just stood there with her arms crossed and a shy grin on her face. I looked up at Jenny and then at the large flesh coloured dildo wiggling from her crotch.

 

"Cath?" I said looking at her again. "Are you su... " I was stopped mid-sentence as Jenny suddenly reached and grabbed the towel and pulled it. She yanked hard and it slipped from under me revealing my 7" swollen, uncircumcised cock standing to full attention. Cath gasped and giggled.

 

Jenny stepped toward me as I lay there with my legs over the side of the bed. She ran her hands up my thighs and pulled my legs apart then gently took my cock in her right hand. She bent over and lightly licked the head of my cock with the tip of her tongue. 

 

"Tastes good!" she said looking up at me from under her thick blonde hair. "You're nice and wet." She added standing up again. "But we need that hole of yours to be nice and wet too don't we Cat?"

 

"Uhuh!" my sister responded. Then picked up a bottle of lube I hadn't noticed on her bedside table and handed it to Jenny.

 

"Get me a pillow as well Cat to put under him he needs propped up a bit!" Cath handed a pillow over with the lube. Jenny smacked my thigh and said "Up!". I lifted myself up to allow the pillow to be placed under the small of my back.

 

"That's better!" said Jenny aiming the strapon at my hole briefly. "OK let's lube you up first." She said taking the lube from Cath and squirting a generous amount onto her left fingers. She slowly placed her lube loaded fingers to my crotch and gently pressed them into me. I felt the cold wetness of the lube against my hole as Jenny slowly smeared the lube into my crotch. I groaned quietly at the exquisite sensation of my butt hole being smeared with cold, wet lubricant then gasped as Jenny suddenly inserted a finger into me. She pushed her middle finger right up into my rectum giggling a little as she did.

 

"I got my finger up him!" she said looking over at my sister. I glanced at Cath who was still standing watching with her arms crossed but as I looked at her she looked back at me and raised a hand to her face with what looked like a mixture of embarrassment and amusement. I then gasped again as I felt Jenny suddenly withdraw her finger and then shove two up me at once.

 

"Hmm... "Jenny purred. "He likes this doesn't he? OK. Now. Let's see... " she said as she removed her fingers and picked up the bottle of lube. She squeezed some onto the strapon and started running her fingers up and down its length to spread it. She wrapped her fingers around it and started to run her hand up and down the shaft as if she was masturbating her own cock. She looked at me smiling all the time and glanced over at Cath before getting herself into position and guiding the tip of her dildo to my waiting hole. She pushed gently but my hole was tightening. Partly at the thought of this huge thing being shoved up me and partly at the weirdness of the situation. Being pegged by this big breasted girl as my older sister looked on was making my mind race. But she pushed harder and I felt my anus begin to give in to the pressure. The head of the dildo slowly eased into me and as I felt my anus stretch and the dildo begin to fill me I groaned loudly.

 


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