It was a cold morning in December and the house was finally empty. I stood for a good few minutes, drinking the last cup of coffee from the oversized commercial maker and soaking up the silence after a week in my in-law's home. Not that things weren't polite with the family, Mrs. Jones, my wife's mother, apparently owned this coffeemaker just on the rare occasion that I'm here, since no one touched the coffee but me each morning. it seemed like no one's schedules quite meshed, and there had been at least one other person in the house at all times since we arrived days prior. Either Tammy's mother was vacuuming a room, or Mr. Jones was wandering around with scotch in hand, seeing if you were watching whatever sporting event was conceivably on at that moment. Finally, on our second Tuesday morning as houseguests, I had at least 2 hours alone. It could have been years as far as I was concerned.
I finished my cup and walked up the heavy carpeted stairs to the 2nd floor. My wife and I were waiting for our first house to be finished and needed someplace to stay for the weeklong gap between our lease at the shithole apartment we'd been in and our soon-to-be dream home. Unfortunately, her parent's gracious offer of a guest room for a week had coincided with a freak ice storm, and we were staring down the barrel of an indefinite stay. The situation was starting to wear on all involved, since neither us nor my in-laws had gotten much privacy.
I grabbed a women's catalogue from the wicker magazine basket next to the floral print recliner in my Mother-in-law's Martha Stewart homage of a home and adjourned to the bathroom that connected to my guest bedroom. It was a full bath, with a door on each end of the room. The door opposite our room opened onto a sitting area at the top of the stairs. I locked both doors and sat down on the toilet with the catalogue, wishing I had real porn. Oh, well, I thought, supermodels in boy-shorts would just have to suffice.
As I looked at the pages, my mind started to go off into kinkier territory. Urges like this hadn't come over me so strongly since junior high, and I felt like a schoolboy. I assumed I was just super horny from the situational celibacy and I decided to run with it, chasing my first real sexual pleasure in a week. I had always enjoyed it when Tammy, my wife, played with my ass during a blowjob, and thought I'd take my jack-off session into "wild" territory. Little did I know at the time what "wild" territory even looked like. I slid off the toilet and sat down on the tile, but jumped up almost immediately from the cold on my ass-cheeks. I moved over to the bathmat in front of the tub and started to stroke myself while I tickled my ass. I found a bottle of hand lotion under the sink and squirted some on my fingers and began to slowly finger myself. I had liked Tammy's slight probing, but was still shocked at how much I was liking this. My middle finger flicked against my hole and popped inside. As my finger entered me, I felt my cock growing harder and harder. I began to just stroke the top of my rock-hard cock, petting it as my fingers (two now!) slid in and out of my ass. I noticed I was rocking with it, fucking my hand. It felt good.
I bit my lip and got on all fours, bucking my ass against my hand. What the hell had come over me? In a heart-stopping moment, I heard the door to the hallway click.
My Mother-in-law stood in front of me like a scowling librarian. I'm certain if the bloodrush from blushing could kill, I would have exploded. All of the blood in my cheeks seemed to have been diverted directly from my penis, which had shrunk to a terrible, pathetic size. My fingers were still in my ass. She looked me sternly in the eye and cleared her throat.
"Jim, you will get dressed and meet me in my sitting room in five minutes." She turned sharply on her heel and shut the door behind her.
It took me at least two of those five minutes to unfreeze from my pornographic pose on the bathmat. I washed my hand and toweled off my still-horrified dick, then went and put my jeans and teeshirt back on. How did I not lock the door? Why the hell was she home? The sheer weight of life-ending embarrassment almost made me vomit, but I walked solemnly to my Mother-in-law's room on the other end of the upstairs. There she sat in one of her uncomfortable-looking floral chairs, legs crossed. Her hands rested on her knees, her skirt showing no thigh at all. Stockings, real stockings (of all the things a wife could learn from her Mother....) flowed out from under the black skirt down to what should have been sensible black flats. They had been traded for black leather riding boots, calf length. My Mother-in-law was an attractive woman. Her hair, though surely grey at this point, was dyed perfectly black and coiffed in a 50s style that she had obviously never lost confidence in. Though a bit heavy, she did have curves. I was noticing them now, at possibly the worst time. Her consistently schoolmarm fashion sense seemed to have shifted now into something else. The woman in front of me held the fate of my life, my marriage, everything in her hands...and she looked sexier than ever to me.
"Jim, have a seat."
There were no chairs in the room. She saw my confusion and added, "On the floor."
I sat down cross-legged, unsure what to expect.
"Jim, I've always known a few things about you." I felt my face turning red again, my shame burned. "One, you aren't enough of a man for my daughter. Two, she loves you too much for me to tell her that. Now, today I learned something else. That's why I let you have some time this morning, Jim. I knew with a little rope, you'd hang yourself. That's why I drugged your coffee before I left the house, and that's why now we both know what secretly gets you off."
I was stunned.
"I know you look at older women. Tammy found some magazines when you first got engaged. Women my age, right Jimmy? I guessed foot fetish, but she told me you tried to lick her asshole once. That's a dirty little boy that does something like that to make his peepee hard."
Tammy's mother reached behind her chair and pulled out a garment box. She slid it over to me with the toe of her boot.
"Stand up, strip naked, and put these on." I opened the box to find panties and a bra.
"But...look, Mrs. Jones, about earlier" I mindlessly tried to salvage some control over the situation but was interrupted.
"There is no discussion about earlier. I drugged you, but all it did was let out the need inside you. Now we'll work on trying to salvage some pleasure for my daughter's marriage to you. Strip naked, and put on the frilly things."
I did as I was told. I marveled a moment that my hardening cock was somehow as embarrassing now as my shriveled dick was earlier. I tucked a shamefully growing manhood into the panties and stood before my Mother-in-law.
"On your knees."
I got down onto my knees and Mrs. Jones stood and walked toward me. I thought I saw a strange sway to her skirt fabric, but wrote it off. In a moment she had her hands on my shoulders, pushing my ass down onto my feet. She took my hands and placed my palms flat on the floor in front of me, so I was leaned out. Her hand stroked the curve of my back, enforcing it, and ended with a small pat on my ass. I was in heaven, and more scared than I had ever been in my life.
"Look at me" she said, stepping a few paces out and turning to face me. She stared me in the eye and unhooked something on the side of her skirt. The fabric fell away to reveal her garter belt, no panties, simply straps and fabric framing a massive, 10 inch strap-on cock. The veins were ribbed up and down the monstrous shaft, and the skin tone looked as if she had matched it herself with care.
"You, my little boy, are the sexual inferior of my glorious daughter. I could smell it on you when you first asked her out, and if we lived in a real society, I would have turned you over my knee that night and taught you how to serve the way you should. But instead, you just deluded my little princess into thinking she'd found a real man. Silly boypet, your generation is almost entirely the product of single women. There are no real men anymore, just puppies for our procreation, and playthings for our desires. You know it's true, don't you?" As she continued, she began stroking the massive strap-on dangling before her. Her dark red fingernails curled around the head of it, and as her fist tightened she moved her hand down the shaft. Cock poured from her right hand as her left touched under my chin, bringing my eyes to hers. "Don't you feel the conflict in your heart?" She slid her fist back to the base of her shaft slowly, then turned her hand and shifted her weight, digging a finger deep into her cunt. She took her shining finger and wiped a large, clear string of pussy juice onto the head of the dildo. One gleaming drop shone at the tip. "Don't you want mommy's cock?"
WIth that, she guided the head of the cock into my mouth, which was slack and open. my panties were full of cum, I could feel it though I didn't touch myself at all. Her hands stroked my throat and she cooed softly to me, her eyes locked to mine, her cocked sliding in and out of my mouth. "That's it, my little cocksucker. I know. Mommy knows. Take it all, sweetie, take all of mommy's big cock...that's right..."
I suckled on her cock for what seemed an eternity, tears running from my eyes. Once, she reached behind her and fingered her ass, then wiped it under my nose. "This is training, boypet, not playtime. Mommy needs you to lust for her scent, doesn't she? All her scents. That's a good boypet." I realized I had her cock lodged completely to the harness and hadn't gagged. Something in me had finally accustomed to the activity. "There we are, son. I knew you were made for this. There's hope for you yet, yes. Not the man she deserves, but you may be quite something."
She pulled the dick from my throat and pushed me back, my ass resting on my heels. My mother in law leaned down and kissed me. Her lips were barely an inch from my ear when she whispered "You are about to learn your role in this family, Jim. You thought it would be that of the man, and so did my daughter, no doubt. But you always knew you also needed this, and it's okay. Mommy can give you what you need."
She cupped my neck under my chin and pulled my head forward. I moved my hands and shifted my weight until my ass was in the air.
Mrs. Jones walked behind me and knelt down. She stroked a finger up my panties then pulled them halfway down my thighs. I heard her squirt a huge amount of lube onto her cock and she began to stroke herself.
"My boypet, I know your sex life with my daughter is lackluster. She knows something is missing, and has asked me to fix you. My daughter is a woman of great sexual potential. Trust me, I know. After my training, though, you will belong to me and not her. Someday, I will give you back to my daughter to control, but that's a long way down the road for the both of you. For now, I see this as the best way to begin that journey. Sex can be amazing. After we are done here, you will have fulfilled your desire for this extreme, and can begin to give my daughter a taste of what real men bring to the bedroom. Eventually, you will know and love all kinks from both sides of the power balance. For now, though, you are my sissy, and I think you'll like it a lot."
Her fingertips ran down my spine and she pushed against the small of my back, flipping my ass up. I took the hint and got in my best remembrance of a pin-up pose. Her middle finger slipped into my ass, testing the waters. I moaned. She guided the head of her cock to my hole and pushed in. As the tip popped inside me, she stopped. A hand reached up and took my throat as my mother in law leaned up to whisper in my ear, "You are mine, and my cock is your drug. I will make you crave this, boypet, and your sweet cunt will ache to be filled by it."
With her fingers still around my throat, she slid her cock deep into me, rooting herself into my sexual desires as she forced inch after fleshy inch into my ass. Once she was buried to the hilt, her laugh filled the room and she paused her fucking.
"That was the front door, boypet. Tammy, darling? Is that you? Come upstairs!"
I looked up from my reverie to see my beautiful wife holding her Christmas shopping in the doorway to the room. Without missing a stroke, my mother-in-law pulled almost out of me, then drove her dick back inside, forcing out a moan from me inspire of myself.
I heard the bags hit the floor as my cock let go a spurt of cum into the carpet.
"Shut the door and come here, Tammy. It's supposed to snow again this afternoon, and your father should be back soon."
"Jim?" Tammy had tears in her eyes as she looked toward the point where her mother's thick cock was vanishing into my newly minted fuckhole. "Jim, I'm sorry to have set this up, but I hoped...I..."
"It's okay" I started to say, but her mother cut me off.
"He loves his mommy's cock, don't you boypet?"
I looked from my wife back over my shoulder to the proud woman who's veiny dick was splitting my asshole apart and fulfilling sexual fantasies i had only begun to dream about. I looked back at my wife through my own tears as my Mother-in-law pressed her cockhead against my prostate and a voice from far away poured out of my mouth.
"Yes, please ma'am...I love my mommy's cock!"