Bdsm Family

All in the Family

It was a week after my eighteenth birthday when the worst day of my life happened. My grandmother walked in on me while I was alone in my room. One might think I was masturbating, but it was so much worse than that.

I was a tall, thin geeky kid, with black hair that didn't behave. I was old enough to shave and I did that regularly, keeping my face clean. My hips stuck out and my ribs were visible. I had a decent-sized cock. I'd measured it and it was seven inches long and normal girth. I was circumcised and had plenty of black pubes. I was also a virgin. And a pervert.

I loved bondage, the idea of it. I also was a sadomasochist. Pain turned me on, both receiving and inflicting, though the inflicting had been, up to this point, theoretical. Since I was shy and had no idea how to find a kinky partner, I did things to myself. My favorite was self-bondage. And that's what I was doing when Granny walked in on me.

I was naked, of course, lying on my bed. I'd hogtied myself using leg cuffs and a wrist chain, attached to each other, so my arms and legs were in an 'X' shape under my butt, hog tying me. I made certain my bonds were tight enough that I couldn't escape. It turned me on to gag myself so that's what I'd done, using an actual red ball gag around which I slobbered, mouth forced open. My method of escape was a key on the floor on the other side of the room. I'd wriggle around across my bed, onto the carpeted floor, and across it to get the key that would unlock my wrist bonds and free me. The wriggling on bed and carpet felt good on my bare skin.

I start face down on the bed and had only just turned over onto my back, my cock sticking straight up from my pale, skinny body, the head shiny with pre-cum, when my grandmother opened the door. I froze in panic, eyes wide, as I looked at her. Her eyes got big and her jaw dropped too.

I thought she would close the door and leave in embarrassment but she overcame her brief surprise and came into my room, closing the door behind her. She came to my bed and smiled down at me. Granny was in her late fifties, I think, having had my mother young. She was in good shape - she worked out all the time. I'd seen her in a swimsuit and her skin, while soft and kind of loose from age, was better than other old women. Her features had sharpened with age instead of sagging. Her grey hair was "done" today, surrounding her face in a halo of grey curls. She did her makeup in a demure manner. Today she was wearing a grey dress out of the 50's, the thick material from waist to neck tailored to her shape, her breasts underscored by darts under each of them. The dress had long sleeves and, below the waist, the skirt flowed out loosely to her knees. She had hose on underneath and square black heels.

She came over to look down at me, naked and hard, on the bed. I was starting to lose my erection due to fear and vaguely wishing I was dead. "Look at you, all tied up," my grandmother said with a smile, then kneeled down to look down my body, from bare cock to face. I'd shoved a magic marker up my ass -- I liked how it felt -- and I was embarrassed because she could obviously see that too. "Oh, and you have something up your butt," she continued. I grunted around my gag.

"You are a kinky little boy," she continued. "But you're not a boy anymore, are you? You're a man." To my horror, my grandmother, squatting by my bed, knees bent, skirt-covered bottom on her heels, reached for my cock. I couldn't help it, I was trying to look up grandma's skirt but she kept her knees together as her hand circled my cock. Her hand was soft and warm, her long nails pricking the soft skin of my cock, causing a shiver to go through my whole body. I groaned around the gag and came instantly, white gel shooting out of my cock as it jerked, arcing up and then down onto grandma's hand and my own belly, getting into my black pubic hair.

"You like granny's hand," my grandmother cooed, taunting me, leaving her hand around my cock, squeezing it, not seemingly bothered by having my goo on her bare hand. She reached between my legs and pulled the marker out of my asshole, causing me to groan in pleasure. Granny smiled as she wiped the marker on my sheets and set it to the side. Then she stuck the forefinger of her free hand in her mouth to the knuckle, sucking it, making her cheeks collapse, her eyes staring at mine, then pulling it out. My eyes got big as I became more aroused. She gently shoved the wet finger into my asshole, making me groan again, then sawed it in and out. The pleasure from her finger fucking my ass made me groan again in ecstasy, and my cock, still hard, geysered another load of cum, coating Granny's hand more, plopping again onto my belly.

Until now, Granny was just grabbing my cock, not even rubbing it. She went beyond that now and started to rub her hand up and down on my cock, causing me to moan, as she jacked me off, her soft hand lubricated with my own cum, still fucking my ass with her finger. She did this slowly at first, then picked up speed, and I shot a third load. My grandmother finally let go of my cock. She brought her hand, covered in cum, to her face and touched it with her tongue, tasting it, then savoring it. "Mmmm," the older woman said, then wiped it on my sheet. Grandma stood up, smoothing down her skirt.

"Well, kinky boy -- or should I call you 'triple shot,'" she laughed. "This was fun." She leaned over the bed, her face in mine, her hair falling forward to brush my forehead. I couldn't help but look down at the swell of her breasts. "I'll come back next week," she whispered to me, her breath brushing my brow. "If you're just like this, I'll do even more to you -- and with you." At the door, the older woman pulled out her phone, and took a picture of me tied, gagged, and covered in cum. "For my memories," she smiled, but I was worried about what else she might do with it. Then she was out the door, closing it quietly behind her, leaving me to pant and sweat and start my journey to the key.

The Next week

At exactly the same time the next week, I was in exactly the same position on my back on the bed. My wrists and ankles were chained to each other in exactly the same way. I had the same marker up my ass and the same ball gag in my mouth. I wanted everything to be exactly the same in the hopes that Granny would come and do things to me. I had been fantasizing about it all week, the things she might do to me, the things she might have me do to her. Maybe she would untie me and let me tie her up. I imagined her naked. The anticipation of her coming had my cock hard and slicked with pre-cum.

At the same time to the second, Grandma came in silently, not surprised at all this time, not halting. Today she had her hair up, a knitting needle through her bun. She was wearing a tight white blouse, which accentuated her tits, which appeared quit big in this outfit, and a grey pencil skirt again to her knees. She smiled to see me where I was tied up. "You kinky man," she giggled. She came to stand over me, looking down at me again. "Look what I brought," Granny said, and pulled her hand out from behind her skirt to reveal a blue, hard plastic vibrator. "It was your mother's," she sneered and my eyes went wide with embarrassment and panic, but my cock quivered in erotick anticipation. "But first," Granny said and flipped me over onto my belly, crushing my hard cock, my ankles and wrists pointing to the sky.

I could hear Granny lubricating the vibrator with her mouth, slurping. I wasn't able to see as my grandmother pulled the marker from my ass and then started pushing the head of the lubed plastic dildo against my asshole. I grunted in pain as it started to stretch my butt. Then it was in and a wave of pleasure shot through me. Granny held the dildo in, my ass stretched open, and slapped one of my buttcheeks hard. I squealed around the gag and my whole body jerked, then the wave of pleasure hit as warmth spread across the buttock. Then she slapped the other one and the same occurred.

Granny went from the first timid thrust to slamming the dildo in and out of my ass, her fist hitting my tight buttocks, the plastic cock going in and out -- it felt great! Her spanking picked up speed and force. I squirmed at first because it hurt and then after that because it felt so good. My squirming rubbed my cock enough on the blankets to erupt pleasure in my groin, my spoo going onto the blanket. Grandma saw that and kept going until I was obviously squirming uncomfortably, then stopped. Later, I would see that my buttocks were dark red from her spanking, matching her hand. The old woman held the dildo deep in my ass as she flipped me back over, front up, facing her, eyes open, mouth gagged, cock in that halfway point where it tried to decide whether to be hard or soft. She jammed the end of the vibrator into the blankets so it would stay deep in my ass, then looked frankly at me.

Staring me in the eyes, the older woman unbuttoned her white blouse slowly to reveal the round mounds of her breasts -- opulent but not extravagant -- the white flesh peaking over the white lace of the bra supporting them. Looking at me slyly, my grandmother completed unbuttoning and pulled her blouse open before reaching behind her to unhook her bra. With practiced ease the gray-haired woman pulled her bra off without taking off her shirt to reveal her bare tits. They were pale, and round, and not saggy at all, the nipples pink and erect.

"The first time you've seen a woman's breasts?" she asked as my cock shot to attention.

"Mmm mmph," I said around the gag.

"Well, not first time, I guess," she chuckled, "But the first time as a man," meaning not as a child. My grandmother started to crawl forward over my supine form, straddling my naked body with her arms and legs, until my cock brushed the hem of her skirt and pointed up into it. Her breasts floated above my naked body and were soon above my face, where she lowered them to caress my face with their soft skin. She started crawling slowly back down my body, her hanging breasts caressing the bare skin of my chest, then my belly, then my abdomen, and then her pendulous breasts caressed my cock.

My grandmother stopped there and pushed her tits onto either side of my cock. I came immediately, groaning around the gag and thrusting my hips up. Granny smiled. A drop of the geysering cum hit her chin but most shot onto her bare breasts. I groaned again. After waiting for me to stop shooting my load, my grandmother started slowly moving her tits up and down on my cock, my cum lubing this tit fucking. As she got to the base of the shaft with her tits, she bent her head down and extended her tongue to gently touch the tip of my penis.

Granny laughed and then slid her tits back up until the head of my cock was hidden between her breasts. Then my grandmother started moving her tits up and down on my cock, slowly at first, then faster. The wet, soft flesh rubbing my cock sent the pleasure centers of my mind into overdrive. I gasped and slurped around the gag, my breath heaving. And I came again. Granny dipped her head to get a couple more drops of cum on her chin and let the rest fall again onto her tits.

The older woman released her tits and changed her demeanor. She straightened where she was squatting and then stood, still holding her tits. Switching to a one hand hold, she cast her eyes about and then found a pair of my shorts to wipe the cum off her skin, first her chin and then her tits. "Nice cum, good for the skin, you little pervert," the older woman smiled. "Next week?" I nodded, still gagged. "I'll see you then."

Triple Shot

I was waiting for her, of course. I'd bought a new ball gag and cum on it, smearing the cum around so that I would taste my own cum as I sucked on it. It was also bigger, making my jaw wider. I'd left the chains the same. They were cheap and cut into my skin. Earlier in the week, overcome with sexual energy, I had scraped the skin of my abdomen with a box cutter, leaving angry red lines on it.

Just in time, my grandmother entered my room quietly. She carried a nondescript bag. Her grey hair was done as before and she wore another collared white blouse, this one sleeveless, and a longer gray skirt, as well as her black square heels. "Ready for your treat?" the older woman cooed. I squirmed in arousal, my cock trying to get even harder than it already was. As I watched, the older woman undid her blouse, again revealing her round breasts, the only blemish the furrowed skin at her neck, and a white lace bra. Slowly and luxuriously the grandmother reached behind to unhook the garment restraining her breasts, then pulled it off in front, freeing her round, full breasts with their pink, erect nipples.

To my delight, granny stepped out of her shoes and reached behind to unzip her dress, then pulled it down off her thighs, tilting them up and down as she did so, pulling her skirt completely off, to reveal white lace panties maching her bra. She had just a hint of softness around her belly button and above the hem of the panties, and a few hairs escaped. Then she pulled the panties off, revealing a salt and pepper, yet full, bush. The naked woman stood proudly. "Like what you see?" she cooed, and I squirmed again.

"Mmm, mmm." That seemed to satisfy Granny. Then she reached down to her bag and pulled out an apparatus of leather straps. I didn't know what it was, but she stepped through one ring, then pulled a belt around, cinching it, before pulling another strap around her other thigh and cinching it. Above her bush was a flat leather panel with a plastic plug protruding. As I watched, Granny pulled out a big dildo, bigger than last week, and anatomically correct with rubber balls and veins and ridges and head and screwed it onto the peg. She smiled broadly as she dumped lube on it.

I panicked and tried to squirm away, hampered by my own excellent bondage. Granny, a tall woman, was across the room and pulled my knees to the edge of the bed before flipping me over. Without freeing either my ankles or wrists, she separated them from each other and bore one knee on my calves so my knees were on the carpet and my hips on the edge of the bed. Her whole weight on one hand pushing into my back, I was bent over the bed, still squirming in fear. "Here now," Granny said calmly, as the head of her dildo found my vulnerable asshole. "Relax and you'll love it." Granny started pushing her plastic cock into my asshole, stretching it, causing me to moan hoarsely around the extra-large gag and squirm again against my bonds. It was to no avail. The large dildo entered my asshole, finally stretching it to the full girth of the dildo. The pain suddenly turned into pleasure like a firework in my mind.

Fireworks exploded into my head and my groin and I shot my first wad onto the carpet, a true anal orgasm. "See?" Granny cooed as I came and relaxed. She started fucking me rhythmically, her soft thighs and leather straps hitting my ass. She bent over me so that her breasts pressed against my bound hands. "Mmm," the older woman cooed in pleasure as I groped and squeezed her soft, yielding tits, rubbing them in my hands, pinching her nipples. Showing amazing agility, the older woman kept pounding my ass while I squeezed her tits and she reached around to grab my cock, setting off my next orgasm. She laughed. "You sure are a butt slut!" she said, and I blushed but didn't want her to stop.

Granny pounded my ass relentlessly, her sweat mixing with mine, her tits in my hands, her hand wrapped around my cock, stroking it. "Mmmmm!!!!" I squealed around my gag as I came again, shooting onto the cover hanging from the bed. I collapsed, finally wishing Granny would stop. She seemed to feel it and did stop, pulling her plastic cock out of my ass, to my relief. Granny heaved my skinny body back on the bed and reattached my wrists to my ankles and stepped away to take off her strapon harness.

I had an office armchair in my room and she pulled it up to the bed and plopped into it. I had my head turned to her and, as I watched, Granny pulled up one thigh, leaning it on a chair arm, opening and revealing her pussy. Then she pulled the dildo off her harness, wiped it down, and slowly inserted it balls deep into her revealed pussy. With one hand, she started fucking her swollen pussy with the large dildo while she worked her clit with the other, her hand appearing boneless as it vibrated around the top of her pussy. She was soon moaning, her legs tense. Then the older woman pulled the big dildo out and, levering herself up with her legs, braced herself off the chair, and put the dildo under her. Guiding the tip into her ass, she settled down, penetrating herself completely. Reaching down to her bag, she pulled out the green vibrator she had called my mom's, twisted the base until it hummed, then started applying it to her already swollen clit. Sitting on the large dildo she had used to fuck me, three of her fingers knuckle deep in her soaking pussy, vibrator on her clit, she came, biting her lip to keep from screaming, hunching into herself.

Granny relaxed, gingerly removed the dildo from her ass and put it and the vibrator into her bag with her harness and her panties. She stood up, pulled a cloth from her bag and wiped her pussy and ass. Then she was putting on her bra and blouse, pulling on her skirt and shaking her hips, zipping it up and stepping into her shoes. Granny finger combed her hair, looked in my mirror and pursed her lips to even out her lipstick, adjusted her skirt one last time, and stepped out of my room with her bag, not looking back, leaving me bound just as tightly on the bed. I started to squirm towards the key.