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Summer Sissy

Category: Fetish
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It was the summer after my senior year in high school, just three months of killing time until the start of college. I had just turned 18, and I had been single for the entire previous schoolyear. Small town, small school, and small dating pool made for an incredibly dull senior year. My girlfriend for the first three years of high school, the girl I lost my virginity to (the only girl I’d ever slept with) was a year older than me and had gone off to college.

Of course, I’d gone on a few dates, horrible and awkward affairs that had left me coming to terms with my routine of fantasy and masturbation. I was starting to think that I’d had all the sex my lame social existence would ever allow. Still, being an 18-year-old boy, the only thing that I ever thought about was girls, and my complete failure with most of them had not ended my dreams of lust. Instead it had led me to broaden my sights until I fantasized about nearly everything imaginable. A light breeze was enough to get my dick stiff as a board physically, and mentally my fantasies had become limit-pushing fetish quests. I poured over the 900 number ads in the tattered porno mags I had, imagining every delicious and perversly advertised kink.

I had been mowing lawns since junior high, my summers spent in 100 degree heat and high humidity shoving a gas mower around the yards of everyone in my neighborhood. People moved over the years, spreading out my net around town so that at times I was piling the lawnmower into my VW beetle and driving a few miles to go mow lawns.

Ms. Vann, while not exactly a shut-in, was easily the fattest woman I had ever seen in real life. She was tall, a huge and sturdy woman always dressed in flowing muumuu dresses. I never really thought of myself as having any kind of fetish for that, but I had found a magazine once dedicated entirely to overweight women and had to admit that there was something appealing about it. Maybe it was the outlandish curves, the smallness of me in relation to these women, the power of a giantess, who knows. Maybe it was just the sense that these women existed outside the standard realm of attraction, and so were potentially more likely to venture beyond standard missionary position. In this particular case, I couldn’t have known how right that was.

While shoving the gas mower in concentric rings around the yard in weather that felt like waterboarding, I often had fantasized about Ms. Vann. One hot afternoon in early June after I was done mowing, I was trying to wipe the sweat from my face onto a completely soaked shirt. Since I had mowed Ms. Vann’s lawn for years, I didn’t feel too terribly awkward going into her house to get a towel and a glass of water. When I didn’t see her around immediately, I went to the kitchen and poured myself a glass. The AC felt amazing, and soon I was shivering a little in my wet clothes. I finished my water and went down the hallway to the guest bathroom, hoping to find a towel to dry myself with. My pants were sopping with sweat, and once in the bathroom I took them off and began to dry my legs.

I had lost quite a bit of weight over the last year, and was still shocked by my skinny legs since I had always been a chubby kid. I peeled off my sweaty shirt and blushed. My legs may have lost all baby fat, but it was beginning to look like I would have fat kid “bitch tits” my entire life. I held the towel up over my chest, trying to ignore the shock as the fabric touched my sensitive nipples. I taken off my green grass-stained shoes at the door, and had stopped wearing underwear at the start of the summer thanks to something I read in an old Playboy. I looked at myself in the mirror of the bathroom, turning to see my butt and legs, trying to ignore the unmanly, supple, fat breast curves of my torso. I covered myself with the towel the way a girl would, the hem up around my armpits. My pants and shirt were in a wet pile, and I bent to pick them up and spread them out to dry. The towel fell forward and cold air drafted across my backside as the door clicked open suddenly. I turned in shock, dropping the towel. Ms. Vann stood immense in the doorway, her sharp intake of breath turning quickly to a hearty laugh as I scrambled to pick up my cover.

“Why on earth are you naked in my bathroom, Mr. James?”

She walked into the galley bathroom, taking up the full space with her girth. I stumbled backward, toward the toliet and stammered a reply.

“I was sweaty and my clothes were wet and I needed a towel and…”

“Shush. Put some clothes on like a normal person and…are you aroused, Mr. James??”

Sure enough, my dick was betraying me. Despite the fear and embarrassment, I was hard.

She stepped ever closer and took the towel from me. Her huge fingers and thick hand brushed my face in a calming manner and she put her other arm around my back. I fell into her fat bosom, the adrenaline of the moment draining out of me.

She just stared at me for what seemed an hour. I started to squirm under her gaze, hoping soon she would at least say something, give some hint as to how over my life was now. I tried to swallow and my throat let out a half-sob.

“Shhhh, shhhhh, Billy……this could change things. I’ve seen you look at me with that teen-boy lust, before, Billy.”

She placed her hand on the bathroom counter and it creaked slightly under her weight.

“Not many men ever look at a woman like me with that kind of want. But I’ve seen it on you. I’ve seen it, and I’ve waited. You just had a birthday, didn’t you?”

“Yes, ma’am.”

“Yes, I thought so.” She stepped back, but kept the towel. “What about me makes you horny, Billy?” Her hands ran down her sides suggestively, then she ran a finger up my bare and hairless chest. Her finger traced lightly under my tiny breasts and flicked my hard nipple. Before I could answer her, she remarked, “You have the chest of a pubescent girl.”

Tears welled up in my eyes.

“No no, it’s beautiful, little one. I find your body incredibly sexy. I’m not ‘conventionally attractive’, but I see something about me is working for you too…I know you’ve watched me, and thought about me, Billy, and I’m almost certain you’ve masturbated thinking of me. I hoped I’d have this chance once you were legal, and I don’t want to waste it.”

Ms. Vann moved forward, causing me to step back until my bare back was against the bathroom wall. She pressed up against me until I could smell her skin. I couldn’t move around her, and her weight was against me like a threat. She shifted one hand between us and brought it up under my chin, holding my face to meet her eyes.

“Are you still turned on, Billy?”

My cock pressed hard against her flesh, trying to stand straight.

“Yes, ma’am” I whispered.

“I like some pretty kinky stuff, Billy.” Her hands pressed up my chest again, cupping my fat. Her left hand moved up to my throat and closed lightly around it. I looked in her eyes, my dick so hard I was leaking out pre-cum.

Ms. Vann leaned her mouth down to my ear and whispered, “Would you like to know what I like, Billy?”

“Yes’m” I breathed out shakily.

“Mommy likes to be worshipped. I own the things I fuck, and I’ve been watching you for years. I want your sexuality, I want to own you like a whore for the next three months. I want you to worship me, Billy.”

I stared up at the incredibly large woman who had to be my mother’s age, trying to put in context the pornographic language coming from her lips.

“When a woman has the body I have, it’s not enough to simply have some sex and move on. I have needs, little one. And I want you to fulfill them. In return, I will fuck you like nothing ever has. I will give you the sex you imagine late at night when you think even God is asleep. If you agree to be mine, to worship at the altar of my lust, then get on your knees and be baptized.”

Tears rolled down my cheeks as I sank to my knees naked. Ms. Vann lifted the hem of her dress and tucked it under her monstrous tits. With one hand she held up her stomach, revealing a hairless and dripping pussy tucked between her giant thighs. her other hand touched the back of my head and moved me toward her snatch. My tongue reached out as my palms hit the floor in front of me to hold me stable. She pushed my face into her womanhood and moaned. I could barely breathe, her juices and scent were acrid and strong in my mouth and nose. I felt my cock spurt its load onto the floor as Ms. Vann let her stomach fat down onto me, both her hands now holding me in place as she ground her cunt into me. I heard her say, “Now, boypet, you will be marked by your mommy. Cup your little titties and pinch your nipples, then open your mouth and prepare to receive my sacrament.”

I did as she said, leaning back on my heels and cupping my tits like a slut. My mouth was open and I stared into her eyes as she began to pee. At first I flinched back, but her huge hands grabbed the back of my skull and pulled my mouth to her flesh. I drank her piss, marked by this giantess, my sticky little cock stiffening again at the sheer lust on display. She finished peeing and wiped one hand across my dick. she placed her cum-covered finger in front of my face and spread the semen on my lips.

“If you get dressed and leave now, I understand. It’s a lot to adjust to, having the opportunity to have the kinkiest sex you’ve ever imagined. If you choose to stay, you’ll be in my bedroom in 5 minutes. I need my baby boy to lick his Queen’s asshole until she cums. She put one hand behind her back and then wiped under my nose, the scent of her musty ass filling my nose.

“Mommy has so much in store for you, my little girl-boy. I’ll see you in my room.”

She moved from the bathroom, her dress falling back down as if nothing had occurred. The door clicked shut behind her. The air conditioner shut off, leaving me in a still silence. Ms. Vann’s piss was drying on my face, mixing with the sweat on my skin. My dick was covered in my spunk, but still half-hard. I was on the edge of horny abandon, my nerves skittish and jumpy. I closed my eyes and thought of all the perverted things I’d done to myself in the last few years, the times late at night when I had licked up my own cum from my hand, or beat off furiously while doubled over, shooting in my own face. I thought about the wet dream I’d had of a woman taking me from behind, of the one time I had tried to accept my shame about my body and had tried on one of my mom’s bras, then fucked my asshole with a cucumber until I came without touching myself. To now discover that Ms. Vann was as perverted as me, maybe even more so…I rose to my feet still smelling her ass and her wet pussy on my lips. Her bedroom door was open at the end of the hallway. I heard her deep, matronly voice call to me.

I entered her bedroom stroking my cock absently. My eyes searched the room but there was no sign of the giant middle-aged woman who’s piss I wore. I heard her voice again, and looked into her master bathroom. There was what I assumed was a walk in closet through the bath, and I entered to discover that the closet opened up to a room hidden from view, a half-bedroom made possible by shortening the living room wall on the other side. Ms. Vann sat on a high throne, a wide and sturdy chair on top of a short stairstep. Her seat was angled so that she was laid forward into supports that were carved to resemble the breasts and torso of a Wagnerian opera singer. It was almost viking in its style. The place where her crotch rested had some kind of protrusion extending from the chair seat into her pussy. I could hear a subtle hum. The wood below the chair was stained a dark gloss from what I assumed was years of her juices. She motioned behind the chair to what I realized were kneeling pads. I placed my legs into the chair and my body was guided into a position supplicated behind her ass, which hung above me thrust out and spread open by the chairs construction. The vibrator in her cunt laid next to a small trench in the wood that guided a dribbling stream of pussy juice and sweat out the back of the chair, and without hesitation I licked up a mouthful of the nectar. My tongue then found her asshole, the musty and dark scent and taste of her most profane and dirty spot. I licked slowly across ever part of her voluptuous fleshy ass, and then settled again into her hole. Her great hands pulled her cheeks further apart and she cooed sweet nothings to me as I drank her lustful river and cleaned her most hidden places.

Finally, after what seemed a trance-like eternity, I felt the hum switch off and Ms. Vann stood up from her throne. The vibrator made a slick suckling noise as it came free from her pussy. I stood up and backed away from the chair, my eyes fixated on the dildo.

“I see you want it. Suck it clean for your mommy.”

I walked toward the throne and climbed up the steps, getting my face to the height where I could taste this woman’s sweet toy. It shone with her juices as I put my lips on the dildo, sucking it all in and licking the device clean. When I got down from the chair, I saw Ms. Vann had put on some sort of harness around her massive hips. Her heavy breasts were held up by a combination of leather and latex in a domination fetish bra. She commanded I get to my knees.

“You drank my piss from my cunny. You licked inside my ass. You’ve let me say ‘Mommy’ a few times, and given no argument. You went down on my vibrator. and if i’m not mistaken, you’d like even more. Am I right, little one?”

“Yes ma’am. Yes, Ms. Vann. I don’t know why I’m like this. I’ve always thought about dirtier and dirtier sex. I think what turns me on is kink in general. I’m sorry, i’m sorry…”

I began to cry.

“No, no, no baby. Don’t cry. I couldn’t be more thrilled that you feel that way. I had fantasized about seducing you, and hoped you’d be into a few things…big women, first and foremost, obviously. But now I want to show you how deep this rabbit hole can go. We have this summer. We can do anything we want. I’ll call you parents and tell them I need some in-home help this summer, projects around the house. I’ll even pay you, and you’ll be my little whore. Would mommy’s little whore like that?”

I looked up at Ms. Vann. Her hand found my throat and she held my gaze to hers.

“Would. Mommy’s. Little Whore. Like that?”

“Yes, please Mommy, anything for you.”

“Good. Now I’ve got a bra and panty set my niece left here last year and I think it will fit those little a-cups of yours nicely. Once you’re all pretty for mommy, I’m going to introduce you to my strap on cock. I think you’ll love it when I take your asshole and make it my pussy to fuck, don’t you Billy? Mommy’s cock will fit just perfectly inside your boycunt. Now run find your babygirl clothes so I can teach you to service your ruthless Queen’s fat dick.”

She gave me a light swat on my ass as I got up to go to the closet between this playroom and her bedroom and bath. In the closet was a wire basket full of giant bras and undergarments, unmistakably Ms. Vann’s, judging by the amount of material. Folded neatly under those things was a much smaller pink pantie and bra set. The bra had padded cups and the panties had a tiny bow in the front. They were carnation pink. I stepped into the panties and pulled them up, tucking my stiffening dick back between my legs. I looked behind me and saw my pert little bottom in the girlie cotton and shivered, thinking of Ms. Vann’s plans for me. The bra was tricky, but I figured it out and finally was ready to present myself to the new center of my sexual life. I walked into the playroom to find Ms. Vann stroking an enormous flesh-colored dick attached to her harness. It had to be a full foot long, as wide as a soda can, and it matched her pearly, pale skin almost exactly. The leather straps matched her corset, and she snapped her fingers at me. The action caused a jiggle to run through her entire body, obscene amounts of flesh poured from every seam of material. Her fist ran up and down the length of her cock.

“Oh, you look so sexy, baby girl. turn around and show mommy your backside.”

I turned and got down on all fours, bowing my back and perking my ass up into the air. one hand rubbed my tits through my bra, then slid down to stroke my little rosebud through the fabric. I closed my eyes, almost fainting from the anticipation of Ms. Vann’s dildo. Instead, I felt the pressure and quick pop of a large buttplug going into me. I had never experienced a professionally made anal toy, and the perfectly contoured shape of the plug was a welcome pleasure. Ms. Vann attached a collar and leash to my neck and led me off the bed and onto my knees. The cock bobbing out from her huge pale crotch was in proportion to her weight and stature, a grand and obscene manhood for this outsized and mountainous woman. She rolled the leash around her wrist and pulled my face to the end of her dick.

“This is my cock, babygirl. This is your mommy’s fat, beautiful dick. It is the greatest gift you can receive, and you will love every second of my time inside you. I will bless you with regular fuckings, and your little asspussy is going to become the finest piece of tail anything has ever fucked. For now, though, just let that plug get you ready. Look upon mommy’s cock. Kiss on it. Lick my shaft. Put your lips around the head of my thick and powerful dick. Slide mommy’s cock down your little whore throat and become my dicksucking princess. It’s okay here. It’s okay with me. Your Queen commands you to be the slut I see in you!”

My drool-slick lips parted and caressed the head of her dick. She guided the monster into my mouth and down my throat. I relaxed and opened up, my eyes rolling back as my Mommy Queen made me a cocksucker. My ass ground the plug back and forth inside me and I licked and sucked on Ms. Vann’s strap-on. Finally, she pushed me away from her, pulling the leash to place me on my back, on the bed. She stood before me and pulled my panties halfway down my legs, then lifted my feet and crossed them at the ankles. I felt the buttplug come out from my asshole, but the emptyness was soon filled with the pressure of her giant cock.

“Push out, babygirl. Open up that cunt and let mommy fuck you. That’s it…Mommy’s wants to give you her dick, babygirl. Mommy wants to give you her dick…”

She thrust forward, the head and first inch of shaft leaping past my sphincter before she stopped again. She wrapped the leash tighter around her hand and pinned me to the bed by my throat. Her other hand reached to the nightstand and picked up a cordless phone receiver. She began dialing and slid anouther inch into my ass. My feet dangled over her shoulder, panties on my ankles. She put the ringing phone to her ear.

“Mrs. James?” she asked as she pushed her cockhead further into me. I flushed bright red at the fear of my mother on a phone here, now, in this room, while I lived out my darkest fantasies.

“Oh no, everything is fine. I had billy do some extra chores around the garage for me, some honey-do’s, you know…I have a few boxes in the attic I’d still like his help with. I was just going to order him a pizza, but wanted to let him check in with you. Here he is.”

With that, she held the phone receiver to my ear and stared me in the eyes. She began to slowly slide her cock deeper into me as my mom spoke in my ear.

“Billy, are you being nice and helping out Ms. Vann?”

“Yeah, mom, it’s just moving, uh, boxes, uhh, and stuff…” I could barely put a sentence together staring into Ms. Vann’s eyes while feeling her dick move further into me.

“Well, your father and I have that Rotary thing tonight, so we probably won’t see you until tomorrow morning. Don’t stay out too late once you’re done at Ms. Vann’s. Be nice to her, do whatever she needs, okay?”

Ms. Vann’s voluptuous flesh touched mine as her cock completed its penetration.

“Anything she needs, okay, yes’m. Okay, love you mom. Gotta go.”

Ms. Vann pulled the phone from my ear and spoke into it again. “Yes, no it’s no problem, he’s been a godsend. Thanks, you too.”

She put the phone back on the nightstand and pulled the cock half-out of my ass. Her hand curled around my throat as she slid back to the hilt. She leaned over me, her face inches from mine. We held like that for a few minutes as she fucked my ass. I was beginning to truly enjoy the feeling of her moving inside me, the head of her gorgeous dildo rubbing against my prostate as her endless flesh filled my sight.

“Call me Mommy” she said into my ear as she wiggled her dick in my ass.

“Mommy” I whimpered. Her cock puled out and filled me again as if she was driving her will into me with every stroke.

“Call me your ruthless Queen.”

“You are my Queen.” Stroke.

“Ruthless.” She was finding a rhythm now, and I noticed myself changing my posture slightly to accommodate the complete and total supplication of my asshole to this hulking goddess’ fake cock.

“Ruthless Queen Mommy please I love it please I want it please please I want to pray to your cock and drink from your holy cunt”

“Open your mouth, my boypet.” I obeyed. She spit into my mouth and I swallowed it down. I was turned on by any secretion my Mommy Queen produced, I was her little fuckbitch and I knew it in my soul.

She released the straps on her harness and left the giant dildo buried inside me. Her knees caved in the edge of the bed as she moved up to place my tiny dick inside her pussy, her muscles milking me to a quick completion. She then crawled up my body and held herself open at my mouth, peeing just a little as she loosened my seed from inside her. My own cum poured from her lips and onto mine as I drank it down, her cock sliding out of my slick boypussy. We rolled over on the bed and I began to suckle at her breast while she stroked my hair, occassionally dipping her finger into her snatch to give me a fresh taste of our sex.

We were like that for hours, and I dozed off dreaming of what the summer could hold.

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