Summer Sissy Ch. 02bybartleby_prefers©
This, as the title suggests, is the continuation of Chapter One of Billy's adventures. Thanks to everyone who enjoyed the first part.
Ms. Vann, a long-time customer of my high school lawn-cutting service, had this day revealed to me her desire to make me her personal sex acolyte, indoctrinating me into a perverse world of sissydom and crossdressing. I, being an 18 year old small-town outcast with a penchant for sexual exploration, agreed wholeheartedly, and had been fucked like a back alley whore by an incredibly fat woman. Her weight wasn't all perfect curves made large, much of her flesh was dappled by stretch and cellulite, and her sweat was profuse and acrid. Still, I couldn't deny the days I'd spent mowing that fat woman's lawn, cock hard in my shorts at the thought of her mass crushing me into her privates. I'd never even dreamed of the heights of pleasure today's real experience with Ms. Vann had brought.
I had slept for a few hours, I assumed, since I was alone and the room was dark. I looked around the bedroom for a clock, feeling the lube between my asscheeks as I rolled in the sheets. The bedside digital read 8:12. With my parents out at a social event, I knew I had the night to continue this fantasy. Honestly, I had to keep going to prove the reality to myself. I still had a collar around my neck, and the leash meandered off the edge of the bed. I licked my lips, tasting the salty residue of my crazy afternoon. My hands slid down my sides, passing over the fabric of my bra, embracing my tits. I pushed past the feeling of shame, turning it into a contrary lust as my ass bucked out involuntarily at the caress of my femininity.
I went back in the bathroom, where the light of a scented candle illuminated the mirror. I strutted and gave my most sultry looks at the whore before me. I found my panties on the floor and put them on, letting my cock stick out over the elastic. I stroked myself to my own image, turned on by the duality of my sex. Finally, I dropped to all fours and put my ass in the air, bucking out my last few pulls as my cock shot cum onto the bathroom floor. I opened my squinted eyes to see the huge shadow of my Queen filling the doorway.
"Well, at least I know you aren't faking for my benefit. You really do want this, don't you babygirl?"
I looked up, still on my hands and knees and decided to embrace the moment. I nodded yes, then pushed two fingers into my ass and licked my seed off the linoleum.
"Oh yes, yes yes yes, little one." Ms. Vann moved to the toliet and sat down. By the time I sat up from my snack, I could hear the stream of urine splashing into the bowl water. She finished up and told me to flush the commode. I reached past her hulking frame and tripped the lever, disposing of her waste. Her rolls of fat hung forward off her, covering her pussy, and she slid forward on the seat and used her hands to reveal her cunt to me.
"Lick the dew from me, sissyboy."
I moved into position, genuflecting low before my Queen's piss-wet jewel. I licked the bitter drops of her golden pee and could taste our earlier adventures in the folds of her lips. I ground my ass into the floor at the memory.
She stood, shoving me away. "Meet me in the living room. Pizza is on its way. Put on the clothes on the bed. No undies, sweet. Understood?"
The question was clearly rhetorical, because she left the room as soon as she said it.
I left my panties on the floor and looked for the clothes. They were on the edge of the bed, a very short miniskirt and a low cut sweater. Thigh high white stockings, black wedge heels, a short pink wig and red lipstick were next to them. I blushed, but despite my fear I began to pull the stockings on, relishing the feel of the fabric on my skin. The sweater and the bra underneath showed off my breasts. The shoes fit too well to be an accident, and I began to think Ms. Vann had been serious about watching me for years. Once the wig was on, the only thing breaking my illusion of girlish charm was the hard cock lifting my skirt hem. I took the lipstick and went to find Mommy Vann.
As I moved down the hallway, I could hear the low sounds of a television. Ms. Vann sat in her overstuffed leather recliner, watching the flickering screen.
"Oh, wonderful, you're dressed", she said without turning. "Come here and kiss your mommy, pet."
I went to her. She sat reclined in the chair, her satin robe open. She wore black stockings held by thick black straps, her huge and pale thighs pouring out the tops. Her pussy lay bare, and she looked me up and down while gathering and releasing her pillowy breasts. She bit her lip and I sank into her lap. Our mouths met and we kissed, wet and sloppy and hungry.
"Where is your lipstick, pet?"
I handed her the tube, explaining that I'd never worn makeup before. We stood out of the chair and she walked me to the mirror on the wall, filling the view behind me as we faced ourselves. She took the lipstick in one hand and my cock in the other.
"You see, baby..." She began to apply the makeup as she stroked me. "You just put the lipstick on like so..." Her pace quickened and I struggled to remain still as she dolled me up. Suddenly, as she finished my lips, her hand slapped my cock. My erection cratered as I fell to my knees with a shout.
Just then the doorbell rang.
"Ah, pizza's here. Babygirl, you should answer the door. Without that unsightly dicky, Tommy's not going to know you aren't my niece Katy in for the weekend. Tommy and I have an understanding regarding his tip, so once he's good and hard send him back to Mommy's bed." She unhooked my collar.
'Nice and hard', I thought? Ms. Vann was already gone, and I walked to the door as the second doorbell chime rang out. Tommy was a big dope of a football jock. Not a star athlete, not the kid making the papers, just a big dummy I knew from his monosyllabic threats towards kids at school. "Hey" was Tommy's favorite word.
"Hey" said Tommy, as I opened the door. His frame was muscular and powerful, and he held out the pizza box as if it nearly offended him to have to waste strength on it. "Um.....is Ms. Vann here? She ordered this. I gotta, um, give it to her."
What came from my mouth next shocked me. In a faint and higher register voice, I answered, "Yeah, I'm her niece Katy. I'm just in from college for the weekend. My Aunt is in her room, she said to send you back once you were...ready."
Tommy smiled, the entendre clearly sinking in. He stepped into the house and sat the pizza on the table, unbuckling his jeans as soon as the door clicked shut. "Then get me ready, hot stuff!"
Tommy's cock was ridiculously huge. I had thought the dildo Ms. Vann had worn was a fantasy silliness, but here was something comparable in the flesh. I felt the warn weight of his dick as it began to stiffen in my hand.
"Yeah, get that look in your eyes, bitch. You all do. Look at my dick. Now lick on it. Yeah."
Tommy's lack of poetry didn't matter to me when faced with this thing. I put my lips to the end of it, my tongue mapping the fold of his head, the ridge, his every vein as the monster awakened in my warm and inviting mouth. He put his hands on my head and began to feed his cock into my throat, hardening into me like a velvet glove made to hold his dick. I opened my throat and accepted him, again and again, as his manhood gave my mouth purpose. It took everything in me to pull away from his fully engorged member.
"Finish me, slut!" Tommy nearly shouted.
"I can't. You're for her." I motioned down the hall and Tommy nearly fell over stepping out of his jeans to run toward the bedroom. I licked the precum off my lips and straightened my outfit, then had a slice of pizza from the box on the table.
After a few minutes, Tommy returned from the bedroom and walked to his jeans, his flaccid dick still huge between his legs. "Later slut," he said in passing as he moved to the front door. "If you're in town tomorrow, you should give me a call. Your Aunt's got my number." And with that, the first boy to put his dick in my throat was gone.
Ms. Vann entered the living room and immediately went for a slice. She sat in her recliner, ignoring me as she ate. Her sausage-fingers fumbled with the remote as she began to change settings on her entertainment system. The screen went black, and porn came up. It was a scene of a transexual stroking her thick cock. A young man entered and began servicing her, sloppily licking her manhood.
"Come sit on your Ruthless Queen's lap, sweet boypet." I did as I was told. She reattached my collar and leash. Her hand moved under me, cradling me, and I felt her fingers against my hole as our tongues played with each other. Suddenly she was inside me, fingering me as we kissed. I moaned without thinking, and felt her smile on my lips.
Her pace grew faster, and then without warning she pulled away. Her hand was on my leash in an instant as she rose from the chair and roughly pulled me to the ground before her.
"Drink me." she commanded, like some terrible Alice in Wonderland character.
I placed myself prostrate before her pussy and flicked my tongue up to her lips, awaiting the golden stream of my Queen's pee. Instead, a huge gooey mass of Tommy's semen began pouring from her and down my throat. It tasted different than before, different than mine.
"That's it, little whore. Look at me, you really didn't think I had something going on with my pizza guy? He's not like you, no, but I've got something he wants, I guess, and he gives me something I want." She giggled. "I guess now you want it too, little cum-drinker?"
She was right, I was suckling her pussy, my tongue digging for every drop of seed.
"Get it all, that's my good girl. Maybe someday mommy will let you have it from the source. I assume you got him hard by sucking him, not by a handjob?"
"Good for you. Did you like it? His cock is amazing, even though Tommy's kind of a dolt."
"Yes Mommy Vann, I did like it. I did."
I looked up at her, almost shaking at the thought of what this woman might get me into, and what I might be willing to do for her.
She let the leash go slack and I fell away from her crotch, a ribbon of cum connecting me to her inner flesh. She broke it with her dark red fingernail, curling the strand around her finger. She offered it to me and I licked it clean. "Good, good," she cooed. "Now, lick mommy's chair seat clean and I'll be right back."
She turned and strode away into the house, leaving me to my duties. I looked at the leather recliner behind me. As my tongue touched the dried patch of mommy-wet on the chair cushion, my eyes teared up at the wondrous direction my sexual awakening had taken.
Ms. Vann returned in a few minutes, dressed in an ankle-length red dress, obscenely shaped to her massive silhouette. I had never in my life seen her in clothes this suggestive. I had doubted anyone in town had. The dress split up the sides to the peak of her hips, making the skirt into a lewd shred of a loincloth draped before her billowing gams. I could see the pendulous sway of her strap-on beneath the fabric. The dress was pulled down under her tits, and she gathered and dropped them over and over as she smiled at me. It gave an effect like pouring her breasts through her hands. When she stopped, they fell heavy and full, her nipples like fingertips. She walked toward me and took something from behind the recliner. It looked like a harness for a large animal. Ms. Vann began to put it on me over my sweater, moving the leash from my collar to a ring on the center of my back. She settled into the chair and shifted the front of her dress aside.
"Kiss both mommy's nipples, little girl-boy, then take the bottle of lube on the table there and grease up my cock. I want you to oil it with the lube, get every vein nice and shined so it can move smoothly up your sweet little ass-cunt. Don't you want that, baby girl?"
"Oh god yes, ma'am. Yes." I wish i'd had more beautiful words to give her. My lust was causing me tremors and I wanted to die riding this woman's beercan-thick, 10 inch cock. I took the bottle and began to rub lube onto the dildo, my hands caressing every molded vein and ridge. I ran my palm down the shaft, feeling the swell and fall of the girth. I even lubed up the massive balls, with their strangely realistic textures. When there seemed to be a visible wrapping of lubricant on the dong, Queen Mommy Vann pulled hard on the leash and turned me to face the TV. She flipped my skirt up onto my back. I had never felt so much like a sextoy in all my life, and I fell into the part with total abandon. I wanted cock, I wanted cum and pussy juice and the sweat from the skin of anything that rutted and fucked. I wanted lust, pure lust distilled and poured down my throat through the asscrack of this obese goddess Mommy.
I felt her fingers push into my ass and spread me, preparing me to receive her. The dildo plunged into me, and though it was painful I let out a deep moan of pleasure. My back arched and I kicked my hips back, riding on her dick while she held me with the harness and leash. I crossed my feet at the ankles, bowing my back like a swayback mare, devoting my entire posture to the accomodation of my Queen Mother's blessed dick.
As she sank to her balls in me, her head rubbing against my prostate, I opened my eyes to see what new scene was on screen.
I quickly realized it was her bedroom. I was on the bed, Ms. Vann was over me. No audio was accompanying the video, but clearly I was taking the strap-on cock of a giantess while dressed in women's underwear. By the look on my face, I was enraptured. The video paused, the motion-blurred cock all the more terrifying as it held still in the assault on my bottom. From behind me, her cock shifting inside me in rhythm with her breathing, Ms. Vann began to take me through the video and give me notes on my performance.
"Here, baby girl, you can cross your legs at the ankles, like the old cheesecake photos, and the boys will love it. Pull your ass open for me next time, when i'm like this...do you see? Then I can go deeper into my babygirl's little puss. Ooh! And here, here if you'll suck my titties I can cuddle you in my arms and fuck you. Let's try that..." She turned me, the cock twisting in my ass. Her nipple found my mouth and I latched on, plugged with my mommy's pacifiers at both ends. She rocked back and forth in the recliner and watched ourselves on screen, rewinding and pausing the tape as my Queen found moments where I could be improved as her boypet, her summer sissy whore.
In just one day, I had gone from a frustrated lawn boy dreaming of the freedom of college to a sex-crazed fuck-slave, praying like a heathen to the alabaster Goddess who's cockhead was now in me like a second spine. I wept and watched the screen, listening to the cooing suggestions of the whoremaking fat suburbanite fucking me, my tears cutting through the cum on my cheeks. I smiled, beaming as her dick rubbed my prostate just right, and my dick exploded cum out onto my crossed legs. I flashed to the image of myself in my mother's things so long ago, feeling blessed at the chance to feel this accepting and intimate pleasure. I looked at the semen on my thighs, tasted the cum on my fire red lips, savored the strokes of my Mommy's endless cock. I was the luckiest boy ever in the world, becoming the sluttiest girl ever in my dreams.
As scared as I was at the thought of video proof of my perversions, I was still glad to learn more from Ms. Vann.