Deflowered by Sis

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Sensing mischief in his big sister’s voice, 18-year-old James is curious as to what Lynda has invited him round to her room for. He soon finds out. Lynda, 20, and her lesbian lover Jenny, 22, have a wild and kinky new idea that they want to try out after seeing it in a porno. They want to employ strap-on dildos to bugger a bloke. Young James is trusted, and his arse is firmly in those two kinky lady’s sights.

(This is fiction. All persons are over eighteen. This is a sex story. It includes descriptions of: Incest – brother and sister, Anal, a Threesome – FFM, Sex toys, Lesbian, Masturbation, Oral, and possibly other sex acts.)


With both parents being workaholics, I was used to spending quite a bit of time either on my own or round at my big sister’s. Lynda, my only sibling, wasn’t much older than me and had looked after me a great deal during childhood. Now that I too was at the Uni where she lived in halls with her girlfriend I often visited her there.

It was a Saturday and with my parents working today (they were both doctors) I was sitting around at home on my own. I phoned a younger friend to see if he wanted to come over, but he was being dragged to the shops with his mum to buy school-uniforms. It was only early August, the summer holidays, but evidently my mate’s mother was keen to be prepared for the start of the new school year in a month’s time.

“My mum’s annoying,” my mate had grumbled to me on the phone, “We’ve only just recently finished school for the summer and she is hauling me off to stupid sodding shops to buy sodding stupid school stuff for me stupid sodding final year. I don’t want to be reminded of another year o’ school by trying on sodding uniforms.”

So that left me to sit about the empty house.

Naturally, being an eighteen-year-old boy, it didn’t take long for me to decide to take advantage of my solitude by jerking off. Since I’d discovered the delights of wanking I couldn’t get enough of it. I retrieved my laptop and stripped naked. Soon I was kneeling on my bed and pumping my stiff pecker as I perused favorite sites and the naked ladies within.

Half-way through jerking off, the phone rang.

“Bloody fucking buggery,” I snapped, having to tear myself away from the delights of self-abuse.

Naked and with my rigid cock jutting from my hairy groin at an obscene 90-degree angle, I padded downstairs and found my cell.

“Yes?” I asked, with all the discourtesy of a typical eighteen-year-old boy.

“Hey James,” came the familiar voice of my sister, Lynda.

“Hi Lynda.”

“What are you up to?”


“My my, you must be up to something! Something naughty, I’ll bet!”

“No!” I snapped, defensively, as if somehow my sister knew I had been whacking off, “I wasn’t doin’ nuthin’!”

“James, it’s a simple rule. If you ask a boy what he is up to and he replies ‘nothing’ within half-a-second, that means he’s up to something, probably wanking.”

“Whatever. I’m not a boy, and I wasn’t wanking. Whaddya want?”

“Fancy coming over?” Lynda asked, cheerfully.

“Now? Um…okay.” I enjoyed popping over to Lynda’s. I had a bit of an impossible crush on her lesbian lover, Jenny.

“Hurry on over then. We’re going to do something cool!”

“What?” I asked, intrigued. I had started playing idly with my erection.

“You’ll find out. Come on over. Now!”

“Right now?”

“Yes. Hurry hurry hurry. Unhand it, get dressed and come over.”

“I … I am dressed,” I immediately snapped as I stood there naked. I blushed as I looked down and took my hand away from my cock. How did my sister know these things?!

“Just hurry over little brother. See ya!”

She hung up.

I went upstairs and was considering continuing my wank, but I had lost my erection and my sister had said I had to hurry, so I got dressed in jeans and a T-shirt and left the house.

Lynda and Jenny lived in halls at the Uni on the other side of the small city. It only took me ten-minutes to drive over there.

“Hiya James,” Lynda said when she answered the door.

“Hi sis.”

“Come on in sweetie. Take your shoes off.”

Lynda was aged twenty, two years my senior, and she was studying Psychology. She was five-foot-five (three-inches shorter than me) and very slender, with long brown hair. She had a sweet face, big brown eyes (like mine) and an almost perpetual smile.

She had ‘come out’ last year. Our parents were liberal minded and, although they were somewhat shocked at first, neither was all that bothered that Lynda was a lesbian. All our mum and dad cared about was that their darling daughter was happy, which she quite evidently was, especially since moving rooms next to (actually with) her girlfriend, Jenny, at the break. Our parents had met Jenny on a number of occasions and they all seemed to get on well.

I trudged up a flight down a corridor and into Jenny’s small room done up as their sitting room, closing the door behind me. I took off my shoes and plonked myself antalya escort down on an armchair. Lynda stood nearby and we both glanced round as Jenny came into the room through the door from the loo a few seconds later.

Right now Lynda wore a tight white T-shirt that hugged her firm round boobs and ended just above her navel, showing of her flat midriff. Lynda also had on tight denim cut-offs that showed off her slender legs. My big sis often dressed scantily so I did not bat an eyelid when confronted with such an arousing display of female flesh.

“Hiya James,” Jenny greeted me, sweetly, and she sat down on the sofa.

“Hi Jenny,” I said. Like I said, I had a bit of a crush on Jenny and I blushed a little.

Jenny was a twenty-two-year-old legal letters student. She was an inch taller than me at five-foot-nine, reasonably slim with a nice firm and slightly plump arse and heavy tits that at the moment, as she sat on the sofa opposite me, were trying to burst out of a tight white sweater. She had black jeans on that hugged her hips and firm thighs. I could certainly tell why my sister had fallen for Jenny.

The busty young woman had a really sweet and pretty face, a gentle smile, a tiny lightly-freckled nose and such gorgeous, dreamy blue eyes. She had short red hair that was always splayed out and deliberately disheveled, to look as if she had just gotten out of bed (having been up to something more than just sleeping.) Like most red-heads, she had pale skin, which contrasted with Lynda, who like me was lightly bronze colored.

It was funny the way the two women’s personalities contrasted with each other. Lynda was hyperactive, outgoing and very chatty, whilst Jenny was quiet, reserved and often shy around people she didn’t know. Although Jenny was the elder of the two and was likely to be the primary breadwinner of their future household, it was my sister who came across as more dominant simply because of her loud and extrovert personality. Jenny seemed content to sit back and let her energetic young lover take control of most situations.

“So what’s this cool thing we’re going to be doing then?” I asked Lynda, who stood nearby.

“I’ll show you in the bedroom,” Lynda giggled, trading a glance with Jenny.

“This is weird,” I announced, “You two are up to something.”

“We sure are,” Lynda responded, and she reached down and took my hands. “C’mon.” She pulled me up and I got to my feet. My sister then let go of my hands and turned, strolling out the room.

I then felt a hand pat my arse.

I turned and saw Jenny, grinning as she stood behind me.

“Follow your sister darling,” the delicious red-head urged me.

I smiled. I was definitely intrigued as to what these two gorgeous women had planned, my curiosity heightened by the way Jenny had patted my arse and called me ‘darling’, which the reserved woman had never done before.

“James, hurry!” came Lynda’s voice.

I walked out the sitting room through the connecting loo into the small bedroom next door, Jenny following me.

The bedroom was very feminine, with light red painted walls, plenty of houseplants, white furniture and a single large bed under a big, pink-curtain-framed window. The bed-covers were pink and along with several plump pillows were two big red heart-shaped cushions. There were two dressing tables; on top of one were tonnes of make-up and perfumes, and on top of the other was Jenny’s collection of teddy-bears.

The walls held various pictures, the sitting room, some landscape paintings, the bedroom arty black-and-white photos of female nudes. It was a novelty being in this room as I’d only ventured in a couple of times.

Humming cheerfully, Lynda opened a drawer in one of the bedside cabinets and produced from it the last thing I expected her to produce…a strap-on dildo.

With a giggle, Lynda flung it onto the bed, my eyes naturally following the device. I had seen strap-ons in pornos, but I’d never seen one up close. Now, I could never again doubt their existence. It was about seven-inches in length, white and smooth looking, and fitted to a thin leather strap with a silver buckle.

“Cool eh?” Lynda giggled.

Jenny stood near me, smiling and blushing.

“Whoa, a strap-on,” I sniggered, “Cool.”

“Isn’t it great?” Lynda asked, and she picked the strap-on up and waved it towards me.

“Um yeah, great,” I responded, my surprise at being shown this item being pushed aside by my curiosity as to what this was all about. “What’s all this about?”

“Jenny bought this for me yesterday,” Lynda continued, referring to the dildo rather than my question, “We used it for the first time last night. It’s better than our old strap-on. Much bigger! I made Jenny cum three times in succession with it.”

Jenny sniggered, blushing harder. Naturally, whilst jerking off, I’d imagined Jenny and Lynda sucking and fucking each other. It was only natural. I’d seen them kiss a few times – quite passionately once, when they didn’t know alanya escort I was watching – and I’d wanked off to the memories of such sights. Even if one is your big sister, no male who is old enough to masturbate can fail to find the image of two beautiful ladies kissing mind-blowingly erotic. I glanced at Jenny and felt my cock stir as I imagined her and Lynda fucking one another with the strap-on.

“I came several times too with this big thing wedged up me,” continued Lynda, eyeing the dildo as if it were some sort of magical object, “It’s the best prezzie ever. Especially when strapped to Jenny!”

“What’s this all about?” I asked, repeating my earlier question.

Jenny just giggled, clearly expecting Lynda to do the talking.

“Well,” Lynda began, “Jenny and me want to fuck you up the arse with this dildo.”

“Oh,” was the only response I could think of.

“You see,” my sister continued over Jenny’s sniggering, “we were watching a porno the other day and there was a woman who fucked a guy in the arse with a strap-on. Apparently it’s quite fun, for both parties. A reversal of gender roles I guess. Jenny and me want to have a go but we don’t trust any guy as much as you, so we thought you might like to lend us your bottom.”

“You want to fuck me,” I began, somewhat shocked, “up the arse?”

“Yes,” Jenny replied.

“With that big dildo?” I added.

“Yes,” Lynda replied.

“No way,” I said with a laugh, still thinking they were joking, “It’s too big.”

“No it’s not,” tutted Lynda, waving the dildo in my face, “It fits up my arse and I’m smaller than you, physically.”

“It’ll hurt,” I whined.

“No it won’t,” Jenny pitched in, “Me and Lynda enjoy having up our…bums.” I was amused and charmed by her shy reluctance to use profanities, despite the subject matter, and the fact that, according to my sister, this had all been Jenny’s idea.

“Girls and boys may be different round the front,” Lynda explained, “but round the back, bum-wise, we’re the same. If girls like to be arse-fucked, most boys would probably like it too. Not just gay ones either.”

I was wondering what the hell to say. Would it hurt being fucked with a dildo? Would I feel embarrassed? I was certainly reluctant to just back out and refuse. After all, even if what was being planned wold be a bit of ‘reversal of gender roles’ or whatever, it was still sorta like sex. I mean, shit! Sex! Getting nekked with two beautiful lesbians! How many eighteen-year-old blokes got offers like that?

“Um…” I stammered, still not having fully made up my mind.

“As a reward,” Lynda declared, flinging the strap-on to the bed, “you can fuck Jenny after we’ve fucked you.” She walked to her lover and put her hands on her shoulders, urging the blushing Jenny to turn round and face away from me. “It’s only fair,” Lynda continued, “We’ll both fuck you in the arse and then you can fuck Jenny up the arse.”

Lynda then undid her girlfriend’s jeans and then tugged them down to her ankles, along with her pink knickers.

“Bend over darling,” Lynda told her lover.

With a giggle, Jenny did so, bending right over, her lovely bare arse thrust right towards me. Her cheeks were pale, firm looking and smooth. Her anus – pink, hairless and puckered – lay snugly between those buttocks, beneath it her cunt, which was glistening. It was a superb behind. Jenny was reasonably slim, but in contrast to her fairly narrow waist and slender legs, her bum was somewhat plump. My cock was naturally rock hard in my jeans.

“Is this not a lovely bottom?” raved my sister like a car-salesman running his hands over a Ferrari, “Does it give you a stiffy James? I bet you’d love to fuck Jenny up her tight arse wouldn’t you?”

“Yeah,” I replied, deciding to match my sister’s confident attitude, “She has a lovely bum!”

“So you’ll do it?” Lynda asked, stepping away from Jenny, who stood up straight and turned.

“Okay,” I said, “Sure. Why not? Just be gentle.”

“Hooray!” Lynda said, and she gave me a kiss on the lips. “Let’s get naked people! C’mon, chop-chop.”

Jenny stood with her jeans and knickers still round her ankles. I was briefly transfixed by the sight of the neat triangle of red pubic hair at her crotch. Although her cheeks still blushed red (the cheeks of her face I mean) Jenny nonchalantly stepped out of jeans and knickers, then sat on the edge of the bed as she removed her white cotton socks.

Lynda, meanwhile, was hurriedly removing her clothes. I took off my own clothes, my eyes naturally flicking back and forth between my sister and her lover. Soon we were all completely nude. “What a sexy little brother I have,” Lynda said, approaching me once I stood there naked. She ran her hands over my slender chest.

“He sure is,” Jenny said, and she confidently strolled over to me, giving me a sweet smile as she reached round and ran her hand down my spine, making me tingle and shiver.

I was suddenly conscious of my inexperience. These belek escort ladies were well beyond my league. Not that this bothered my admiring audience. They seemed genuinely attracted towards me, Lynda in love with my arse which she was soon fondling as she knelt behind me, whilst Jenny ran her warm hands over my shoulders and chest.

“What a sexy tight little bottom,” came Lynda’s voice from behind me. I felt her part my cheeks, and I fought the impulse to move away and protect my intimacy. I instead let her spread my arse and she seemed to sigh with delight as she examined me back there.

“Nice and stiff eh?” Jenny commented, reaching down and lightly gripping my pulsing erection. She stroked me softly as I nodded, unable to speak as I felt the completely intoxicating sensation of a hand other than my own on my cock. Jenny gave me a soft kiss on the lips. I smiled at her. It was funny how, without her clothes, my sister’s busty girlfriend was suddenly a bit more outgoing and confident.

“Let’s fuck this charming bloke’s arse,” Lynda said abruptly, standing up.

“How do we do it?” I asked her, Jenny still stroking my erection.

“With lots of lube and lots of patience,” Lynda replied. She took the strap-on and began fitting it to her crotch.

“Come onto the bed darling,” Jenny said to me. She let go of my cock and I followed her in getting onto the large bed, the pink satin sheets cool on our bare skin.

Lynda soon had the strap-on dildo fixed to her crotch and buckled tightly.

“Boing!” she giggled, tapping the end. It wobbled slightly. I gulped at the idea of taking it in my tight young arse.

“I still think we might have difficulty fitting it up me,” I admitted.

“Then I shall demonstrate how easy it is to take in the arse,” Lynda declared, sitting on the bed, “Jenny? Bend over. Show my timid little brother how to take a big dildo up the bum.”

“Very well,” smirked Jenny.

I shifted aside and watched as Jenny got on her hands and knees, her lovely big bottom raised and spread. Her anus twitched nervously, anticipating it’s upcoming penetration.

Lynda shuffled over and knelt behind Jenny, the seven-inch white dildo sticking straight out from her crotch. It looked awfully big and thick relative to Jenny’s puckered anus.

“Open the top drawer and get out the jelly,” Lynda said to me.

I leaned over and opened up the drawer in the bedside cabinet. It was a treasure-trove of perverted implements! Several other dildos were there, along with something I assumed was a butt-plug, and also some anal-beads! I had seen some online web-surfing at home. I also saw a tube of jelly and I took it and handed it to Lynda. She used it to grease up the strap-on, slathering the greasy lubricant along the smooth shaft.

“Put some on Jenny’s arsehole,” she said to me, holding the tube out.

“Okay,” I said, excited at the prospect of actually touching a woman’s bum! I squeezed out some of the lube onto the tip of my forefinger, then started running the tip of the greased digit around Jenny’s arsehole. It felt funny.

“Ease your finger up there a bit James,” Lynda advised me.

I did so, squeezing the tip of my slender finger into Jenny’s anus. Her sphincter felt tight and rubbery. Jenny shivered a little and sighed softly, evidently enjoying this.

“That’ll do,” Lynda said, “Now I’m going to fuck this horny babe. Watch closely little brother.”

I took my finger out of Jenny’s bum and watched carefully as Lynda shuffled forwards and guided the tip of the slippery dildo to Jenny’s back passage. I knelt alongside both naked women, eyes wide with awe, conscious of the warmth of the body heat emanating from my sister and her lover who were so close to me.

“Uuuuuuh,” Jenny groaned as Lynda eased the tip of the dildo into her greased anus, “Oh yeah.”

“See it go in James?” Lynda asked me, her voice heavy with lust.

“Yes,” I replied, “Whoa!”

Lynda had eased a full inch of the dildo’s into Jenny’s anus. She paused a moment. Jenny seemed tense, getting used to the feeling of the dildo up her arse. There was little doubt that she was enjoying it though.

“Push it right up me,” the busty red-head urged my sister.

“You got it!”

Lynda thrust forth somewhat abruptly, pushing several inches of the shaft into Jenny’s rectum.

“Oh yes, oh yes! Further. Fuck it up me further!”

“Wow,” I cried, my prick pulsing erectly. I was as amazed at the way Jenny’s normally sweet and shy demeanour had totally given way to a lustful slut as I was at the plastic cock’s progress up her bum.

With a grunt, Lynda shoved the last remaining inches of the shaft up Jenny’s arse.

“There we are,” Lynda purred, running her hands across Jenny’s back, “See how much it took James? Look how Jenny squirms like a horny little bitch on the end of this dildo.”

“It looks like fun,” I admitted.

“Oh it is, it is,” Jenny said, looking over her shoulder, “Oh yeah…oh yeah, it’s good. Fuck me Lynda. Fuck my arse.”

My sister held Jenny’s hips firmly and began to ease the white dildo back and forth in Jenny’s shitter. Both of them moaned softly with pleasure. Lynda soon began to fuck Jenny a little faster.

I went to touch my cock but I hesitated a moment.

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