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Chapter 5 by toddlertree
Visit a Therapist
Trip to see a Sex Therapist
After all of the excitement on the couch, Alex got up carefully so as not to drip onto the floor. He made his way to the bath and soaked for time, thinking. Exhausted, he fell asleep in the tub. The tub was heated, so when he woke it was only the wrinkling skin that got him to clamber out to dry with a fluffy towel. His mother had left while he bathed, and Alex knew it was far too late in the day now to bother going to school. So, he pinged his class assignments and plunged into studies.
Honestly, the classwork left a lot to be desired. So many of the programs were tracked toward girls. Science, Law, Medicine, Engineering, Politics, and Teaching all were restricted from him. That left Alex with Art, Phys Ed, Music, and a lot of Home Economics. So, he spent time on his oil painting. The canvas was mostly filled with a complex hue of saturated colors. Their swirls and tufts stood up enough to bring a 3rd dimension to his portrait of Christy.
Christy was more than just a girl in school. Christy wasn't Blessed, or even busty in particular. Still, in Alex's eyes, Christy was perfectly beautiful. Her demeanor was defined by being good. It was her angelic face, and her eyes that brimmed with laughter and light. Alex didn't lust after the girl, he didn't fantasize about her sexually. But somehow, at his very first sight of her, he was in madly in love. This was the kind of love that just wanted to give. Give his soul, protect her from harm, be around her enjoying her presence, bask in her beauty and kindness and goodness. Desperately, he wanted her to accept how he felt and bring him into her life.
Mastering oil painting takes a lot of practice, focus, and study. With no studies of importance or much of a future at stake in School, Alex had thrown all his efforts at painting, everyday for hours. Maybe this portrait will be able to say to her how he feels in a way that makes her understand. All his awkward attempts before never panned out. It's hard to talk with an angel. The painting caught her eyes like fire, her long reddish-brown hair cascaded lush and luxuriously down all the way to her slender back, and framed her angelic face in stunning detail. The world swirled behind her in fuzzy backdrop, her lips parting as if about to speak something terribly important. Yes, it was a fine painting.
Finally, Alex went to bed after midnight. Alone. Thinking about Christy got his mind away from the physical attractions that his mother had been parading about. Sex Therapist? Much better to concentrate on how Christy will react when she sees what he's done. You don't have to join a cult with Christy, just live a life with someone that could never hurt anyone... She's perfect and he's going to put her on a pedestal so high...
In the morning, Alex woke with an urge to pee and a hard-on. Grumbling, he made his way to the bath to find his mother already in the shower. Closing his eyes, he made his way to the toilet and bent far enough forward to get most of the bladder's contents into the bowl. Peeking his eyes open to help flush, he caught a glimpse of giant tits pressed against the shower glass. His mother was washing her hair and her tits were widened, flattened by the glass and white frothy bubbles were streaming down her cleavage and around the giant orbs. Alex turned away and got dressed.
After breakfast, instead of school Alex was led outside by his mother. She had changed outfits to be wearing a light yellow sweater and long blue skirt. The sweater was cut with a deep V neckline exposing a generous cleavage supported by a black plunge bra beneath. Eva had applied a thick coating of suntan lotion on her chest "to protect her skin for today's walk". Her skirt was pleated with a ruffles rubbing against her ankles. Her shoes were sensible flats, so she walked with a bit shorter stature than her son down the sidewalk. Side by side, holding hands they made their way toward the downtown from their county road. Eva's breasts shook gently as she walked, but jostled more heavily when she turned to talk to her son.
"Your appointment is in an hour", she said firmly. Eva went on to describe the plan. "Dr. Grudi Bol'shiye is a sex therapist from Russia. Her, accreditations are... impressive." "I'm not going to have my son end up in a barn stall or a feckless fapping colony. She'll get you straightened out." The widely spaced houses on the rural street gave way to closer packed townhomes. A new stretch of road with green and purple swirls ran alongside them. Signs were spaced evenly saying "WARNING! Blessed Lane Only".
Alex didn't pay much attention as Eva spoke, he didn't really want to go. But, what could he do? It's not like he could run off and get a job somewhere. If he could get a job without a reference, say, as a janitor, then someone would surely grab him up as he'd be alone and not collared. "Mom, I should be in school today." he whined.
"Son, sit down for a moment." Eva snapped back. Sure enough, they were passing a white, wooden bench near the sidewalk. It fronted a bakery which was busily catering to a line of commuters trying to buy pastries, coffee and tea. Alex sat down, staring at the bakery instead of his mother.
"Look at me!" Eva snapped again, her fore-finger jabbing her left boob. She stood between Alex and the bakery and leaned down at him. Still jabbing her boob, she stared into his eyes. "Boobs! You've got to focus on boobs. Not school, not painting, not your friends." Then, she moved closer and straddled his legs.
"Touch them!" she ordered Alex. He didn't move, so Eva grabbed his hands and pulled them to her chest. Her breasts sprang back at her sudden movement, then deeply compressed under her heavy squeeze with his hands held against her breasts. "These are the most important things in your life now that you're an adult. You've got to deal with tits. Dr. Bol'shiye will make sure you understand." Some of the shoppers paused from buying donuts to stare at the woman straddling her son.
"You've got to learn how to squeeze them, hold them, pinch the nipples." Eva went on. Eva started moving his hands to rub her breasts forcefully over her tight yellow sweater. "You've got to learn where your dick is supposed to go." And, with that she dropped to her knees and her chest collided violently with his groin.
Alex whimpered in lust, not believing how aggressive his mother had become. The Baker came out of her shop, white apron stretched tautly across her massive breasts, staring at the mother and son couple. Alex met the Baker's eyes, pleading for help.
Eva slapped Alex's face, hard. He turned to look in his mother's eyes. Eva began humping her chest against his groin. "Look at me, damn you!" she exclaimed. "This is what you're going to be doing. Not school. Not friends. Nothing but this!" she hissed. The Baker came closer, her nametag said "Clarissa" and her customers gathered around the little bench. Eva fished out her son's cock from his pants and wedged it into her open cleavage. Then, she started chanting "Titfucking" over and over as she humped his dick with her breasts.

Alex flushed in embarrassment. With nowhere to go and his mother violently forcing her breasts onto his dick, he just sat and watched his dick get titty-squeezed over and over.
"Titfucking", "Titfucking", "TITFUCKING!" she chanted and the crowd took up the chant.
"TITFUCKING", "TITFUCKING", "TITFUCKING", "TITFUCKING" they cheered. Clarissa came around to be behind the bench and dropped her breasts onto Alex's head. Murmuring "Titfucking" herself, she started rubbing her apron covered tits back and forth on Alex's head. Clarissa matched Eva's pace and got louder in the chant, "TITFUCKING!"
Eva's yellow sweater pulled away from her black plunge-bra, exposing all of her chest. Alex's hands had stayed on his mother's breasts and with a mind of their own were now pulling down her bra straps. Free, the oily cleavage was stroking his cock at a frantic pace. He couldn't believe he was actually fucking his mom's boobs.
"Mom, I'm going to cum!" Alex warned his mother. The crowd got louder.
"Cum in your mommy's cleavage" she shouted, stopping the chant and demanded cum. "Cum!, damn you, in my big titties!" "CUM!"
Alex's tongue hung out as he stared at his dick in his mother's cleavage. Pumping furiously, he tried to cum. The crowd fell silent, waiting. Clarissa was shuddering in climax, rubbing her nipples on his back and murmuring "Titfucking".
Eva slowed her frantic jug fucking and squeezed. Squeezed her breasts as tight as she could around her son's dick. She lowered her head, lips an inch from his cock-head and breathed heavily on it. "Cum for me" she said and stared directly at his cock.
Alex spurted directly onto her face, lips glazed with his sperm. He sighed and then tried pushing everyone off of him. After a few moments, he got free and pulled his mom away from the bakery and they finally made their way to the medical office.
The office was brightly lit, smelling of bleach and plastic horticulture. The receptionist pushed out a thick wad of forms for Alex to complete through a narrow window opening. Her outfit showed off a modest bust trussed tight in a corset with a nametag, saying "Anna". Anna also wore a red Trainee hat; she seemed to have trouble doing absolutely anything correctly.
After an hour and a half, Anna called Alex's name and ushered him into the examination room.
"The Doctor will be in to see you shortly, please disrobe and sit up on the chair." Anna paused, as Eva followed Alex into the room. "You might want to apply some oil first, the doctor has a lot of patients to see today." Alex gulped.
The Examination
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The Pillowy Prison
Trapped between Tits
The world has changed. Every day, bustlines inch forwards, cleavages grow deeper, and the aching need to titfuck swells ever larger. As more and more men sink into the cleavages of cruel TitMistresses, one question lies on everyone's lips: Is there any escape from the Pillowy Prison?
Updated on Dec 10, 2024
by Flauros
Created on Sep 30, 2017
by Flauros
With every decision at the end of a chapter your game state can change. Here are your current variables.
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