Chapter 38
by
Raljo
What's next?
Kiara deepens her hold over Billy
When Billy’s bleary eyes finally blinked awake, he was slumped back in the chair opposite Kiara Beaumont’s desk, completely pantsless. With a groggy groan, he sat up, dimly registering how exposed his cock was before his attention went to the redheaded milf studying him from the other side of the desk.
Kiara’s clean white collared shirt was buttoned up again, albeit with the top two buttons left open to expose the juicy, full cleavage of her breasts, which rested loftily on her desk as she leaned forward. Their soft weight looked almost overwhelming. Certainly intimidating. She shifted slightly, and Billy balked at the way her smooth breasts rubbed against the top of the desk, seemingly without her noticing.
She was leaning forward, peering at him through those elegant black glasses on her gorgeous face. Her vibrant, silky mane of red hair was spilling over her shoulders, framing her big tits’ open cleavage so perfectly.
She had fucked him. This experienced older woman, this doctor, this intelligent psychologist milf… She had taken Billy’s virginity, and fucked him so good that he passed out. Her pussy had knocked him the fuck out. The cocky young athlete couldn’t help but feel a little tamed. A little docile. A little fond of the redheaded milf sitting across from him, and a little **** to please her.
He felt his bare, exposed dick start to stir. Why wasn’t she saying anything? Why was she just… Watching him?
He shuddered as he imagined this gorgeous, soft woman shifting his heavy, **** body back into the chair, leaving his dick as as she returned to her own seat and simply… Waited. Waited for the poor boy to come to after she had blown his mind. His dick had been exposed in more ways than one.
Deciding to break the silence, Billy opened his mouth. Or rather, he began to speak - with his eyes locked on those big, soft tits, his jaw had already been hanging open.
“I… I’m so… Um… I’m sorry…” he said, lamely. The words came out more emotional than he had expected them to sound.
He wasn’t sure if he was apologizing for trying to take control earlier, for getting knocked out by her pussy, or for staring at her breasts so obviously. Whatever the case, he felt he should apologize. He didn’t want to disappoint her, or upset her.
Things had been so hard for him lately. Anna had been bullying him at home… Karen’s controlling, bitchy attitude had kept him so stressed out, and that **** video only made things worse. He was still temporarily kicked out of the boxing club, and even though Coach Lucy hadn’t told the other students where Billy really was, he was sure there would be rumors. Rumors that Carly had fucked him up so bad he’d needed to run away and heal.
As the emotions began to well up within him, almost overwhelming him, suddenly Kiara was at his side. He hadn’t noticed her stand up and walk over, but he definitely noticed as those soft breasts pressed into the side of his head, her gentle arms wrapping around him, soothing the torrent of feelings swirling inside him.
She was just standing there, right next to his chair. Hugging him. Billy’s throat felt tight. His bare, exposed dick began to throb, hardening even more with each pulse, slowly standing up in his lap. Kiara just reached around his head, petted his hair, whispering quiet hushes above him as she pressed those soft, warm breasts deeper against him. Cuddling him to fight off those scary feelings.
“It’s okay… I know you’re sorry…” the words were calming, her tone loving. Billy could actually feel his tension melt away, his body relax - maybe even lean a bit into her hug.
“G-Guuhhh… Kiara, I…” Billy gulped. He didn’t even notice the way he had started to subconsciously nuzzle his face against her warm chest, but he did notice the beautifully melodic giggle that rose out of her.
Kiara changed positions, hugging him around the torso now. The milf therapist’s big boobs squished against his chest.
“There there…” she cooed. One arm released the hug and went lower, a single finger dancing over his shaft. Circling and swirling that throbbing, needy erection.
“I… Uhh…” Billy stammered, cut off as the doting redhead planted a soft kiss on his cheek.
“You’re such a good boy. Strong boy. I love boys like you, Billy.”
Billy’s heart pounded with joy as Kiara gave his face another manipulative smooch, showing him adoration and affection, making him crumble even deeper into her cuddle. All the fight had left this rugged boxing champion, as he let out a long, deep, shaky moan, leaning back in his chair and enjoying the way Kiara’s soft chest pressed into his hard pectorals. She was moving slightly now, up and down, rubbing her big boobs on him - imprinting their weight and feel deep into his psyche.
“You’re so hard…” she marvelled, with what sounded like an airy, delighted gasp. Billy wasn’t prepared for it as she shifted herself up, moved her panties to one side, and sat in his lap, sheathing that massive cock in her hungry, powerful pussy.
He gasped at the sudden sensation of her tight warm wrapping around him once again. Now her breasts were really smooshed up against him, both arms draped lovingly over his shoulders as she slowly bounced up and down in his lap, riding him.
“You looked so emotional… I thought you might be about to cry. Don’t be sad, Billy. I’m here for you…~”
Her soft voice took on a slight undertone of delighted, devilish plotting. Billy was too far gone to pick up on it. The sudden shift from cuddling to fucking had stunned him, and reduced his thinking to zero. All the response he could give was, mindless grunting, a deep look of focus on his face. Was he trying not to cum? Or was he trying to remember why he felt like he was in danger?
“Gruh… Uhn. Nngh.” a beat of sweat rolled down Billy’s creased forehead. Kiara’s laugh was heavenly.
“Oh? Is that all you have to say? Has my pussy devolved you back into a caveman, you dumb brute?” she smiled down at him, eyes twinkling. Then her lips pouted, playfully. “But your dick put up such a good fight last time…”
She leaned over and planted another soft, loving kiss to Billy’s cheek. She could actually feel his whole body jump at the affectionate touch, poor thing.
“Gruh. Nng. Milf… Pussy.” Billy barely managed to get out, his brain working slower than it ever had before to figure out what was going on. Why his instincts were telling him to get out of here, when being here felt so good. So safe… So warm…
“Ha! What a stupid boy you are… Such a mighty cock, tamed by playful bouncing…” Kiara smiled, slowly riding that delicious, fat dick.
She leaned forward, taking his face into both hands, and forcing him to look up at her. To look away from her wobbling, elegant cleavage, and stare into those powerful, intelligent eyes.
“Your mind is mine, Billy… Mine to play with…” she cooed. Her voice was so soft. So loving. She caressed his cheek with her thumb, reassuringly. “I know you’re just a stupid, useless knockout slut… I’m going to fix you. You let your own mother knock you out, you poor submissive thing… Fixing this ugly brain of yours is going to be a challenge. But I promise, I’m going to make you all better…~”
Billy didn’t really hear the words she was saying. He was just too emotional. But he knew she loved him. He knew she cared about him. He knew she was going to make everything better. She was going to fix the childish mess he had stupidly made… She was going to make everything right.
Billy was holding back tears as he shot ropes inside this milfy puppetmaster, gasping and quaking beneath her, helplessly bucking up into her pussy.
Kiara laughed. She actually laughed. Goodness, this boy had a GLARING weakness to affection, didn’t he? It was completely different to before. When he’d fought back, when he’d nearly beaten her. Now, he was just so needy.
“Awww… Poor boy… Did my pussy get you all emotional?” she teased, smiling down at his wet eyes and planting another soft kiss on his cheek. “That’s okay… Just let it alllll~ out… /all/ of it…”
As Billy’s cock spurted again and again, deep within her comforting folds, Kiara was softly grinding against him. Getting the last pumps out, breathing airily right next to his ear.
“I know… I know… It’s okay… You need me, it’s okay…” she whispered.
“Ohhhh godd…” Billy wailed, as his dick finally fired out the last of his pumps, and settled down inside her. “Oh god… Fuck… That was… K-Kiara, that felt so…”
“Oh honey… Poor darling… Yes, yes, I know… Shhhh…” she cooed, wiping a tear from his face with her thumb, hiding her grin.
There was a rush of delight she felt, reducing an athlete to this. Oh, how she wished she’d been able to see her high school bullies like this, back in the day…
Emotional. Needy for her affection. Totally under her control, and at her mercy. Their usual swagger and confidence, stripped away, all their vulnerabilities exposed… All their secrets laid bare…
But she wasn’t done. She wanted more. She wanted to make him worse. She wanted to bring SHAME to the dick that had nearly overpowered her pussy. She wanted to make sure it would never try to rebel ever again. So, cruelly, she lifted herself off of Billy’s big, shuddering dick… And, with smirking crimson lips, the redheaded therapist squatted in front of his seat.
She leaned forward, bringing her face up close to that wilting, spent dick. Close enough that her breath tickled it. Close enough to feel its warmth on her cheek as it throbbed and pulsed right before her, like the monster it was. A monster that needed to be taught a lesson. She leaned in closer.
“Mwah~~”
She kissed the glans, so so softly, and then pulled away. She held back a laugh at the shocked face Billy made, gawking down at her. The poor boy was stunned. That one little kiss was already rewiring him, burrowing deep inside…
That one little kiss was going to change everything.
This athlete was going to be such a wonderful, rewarding project for her. Billy’s cock tingled and buzzed as Kiara giggled, pleased with herself, and rose to her feet.
“Oh, did you like that~?” she asked. “That little cock kiss? You look lost for words…~”
Open-mouthed, Billy just nodded, staring up at her as she stood confidently before him. His exposed cock was already rock hard again now, standing straight up as he sat there in his chair. His dick was confused, bewildered, trying to understand what was just happened to it. A small lipstick mark was visible on the head.
Kiara flashed him a gorgeous smile, and buttoned her top all the way up again. Taking a thumb, and pressing it seductively against her bottom lip, she spoke.
“That’s all for our session today… I’m glad I was able to make you feel better, Billy. Get your pants on. I’m looking forward to our next session.”
What's next?
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Loaded Gloves
She has the advantage
Overconfident men getting their bells rung
Updated on Jun 12, 2026
by Raljo
Created on Jan 25, 2022
by Raljo
With every decision at the end of a chapter your game state can change. Here are your current variables.
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