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Chapter 105
by
Johnrocker
During the night…
Middle of the night jerk off
The night was enjoyable, just being body to body with a girl like Winter was any guy’s dream. It’s something he had missed doing, the first time they had been this close in weeks.
He snuggled up behind her, leaving no gap of air between their warm half naked bodies. Mark wrapped his arm around her tightly, occasionally rubbing against her breasts that were free from their confines under her t-shirt. Of course he had to secretly touch her up, it was only human nature.
As late as it was, Mark couldn’t get to sleep that night. Even with his former flame being wrapped inside his arms, Mark struggled to fall asleep. His mind was still too awake and his cock couldn’t calm down either, remaining firm and hard the entire time. His boner pressed up against her buttocks.
Winter who had drifted off to sleep eventually woke up again, noticing how much the boy in her bed was moving and tossing his body around.
“You okay back there?” she whispered to him.
Mark shuffled once more, laying back on his side, facing her back. “Yeah just can’t sleep yet,” he told her.
Laughing quietly, Winter pressed her butt back further, right up against his boner. She did a little shake of her ass cheeks, coming off as quite a tease.
“This got anything to do with it?” she said, referring to his boner.
“Certainly could sleep better with a bit of relief there,” he told her honestly.
It made her laugh a little more. Slowly moving her hand back, she made contact with his throbbing cock. It was still underneath the material of his boxers but it was trying to break through.
Winter teased him at first, just running her fingernails against it. The tickling sensation was too much of a tease for this time of night, Mark had to get himself some serious attention. He pulled down his own briefs and let them slide down his legs. It freed up his cock completely, giving Winter the chance to hold it in her soft warm palm.
“You going to stroke me from there?” he asked her.
“Mhmm.”
“Isn’t it difficult for you to do it like that?” he asked her as she slowly stroked him.
She shrugged while holding onto his penis, “I’ve played with this thing enough times to know I can get you off from any position.”
Winter wasn’t wrong, she knew his cock better than he did. Knowing that, he relaxed his shoulders and the rest of his body as the busty brunette goddess had her way with his dick.
She had stretched her hand back further and was jerking him much faster now. Mark enjoyed the sensation, making things even better for himself, he grabbed her large boobs roughly.
This was no light petting, he was now full on groping them. He moved his hands underneath the t-shirt to feel those pillows of joy much easier. Her tits felt as good as they always did. So soft and plump, they felt amazing.
Mark began to tug on her nipples, although they weren’t initially hard or anything, he was able to make them that way by constant pinching. It seemed to be encouraging her More, Winter tightened her hand grip on his cock every time he played with her nipples.
The squeezing of her breasts and the work rate of her opposing hand was enough to send him into overdrive. She kept wanking him, still not slowing down.
This had all gone a lot quicker than he thought it would. Mark just wanted to fuck her right there and then but he didn’t want to rush things too far, he just laid there, enjoying her breasts as much as he enjoyed the late night handy.
She pumped his cock faster and faster while he leaned forward, his head in her long brown hair. The smell of her hair conditioner just turned him on even more.
Then it all happened in an instant, he couldn’t control himself and he didn’t see it coming.
“Ughhhh god,” he muttered as he began to splurt cum all over her backside.
Mark couldn’t see the mess in the dark but Winter sure felt it. She now had cum all across her ass and up to her lower back, making her t-shirt wet.
“Fuck, I’m sorry, I didn’t give you much warning,” he told her as they both quietly laughed together.
Winter got out of the bed to find some tissues to clean up the mess. “It’s fine. You must have just done this to get me out of the rest of my clothes.”
As she said that, Winter removed her top completely, leaving her in just a pair of black panties. Her large tits now completely free of any covering, they bounced and moved with no effort at all.
Hopping back into bed, she cuddled up closer to Mark and he gave her breasts a nice honk before bed.
It all went quiet as the two settled themselves down, ready to finally sleep.
“Will this change anything between us?” Mark finally said, thinking about this white a lot.
Another pause of silence.
“I don’t know, we’ll see,” she said.
***
Mark slept like a baby after that, his cock now able to rest. They cuddled for the entire night before Mark got up early that next morning to head back to his own room.
What's next?
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Sophomore Year
The sequel story/adventure to ‘Freshman Year’
Freshman Year was wild but things are about to get a lot sexier in Mark’s second year at college. Follow his journey, dating/fucking college girls and still managing to find himself in a bit of trouble at times.
Updated on Jul 4, 2025
by chyoa_fan_9000
Created on Apr 15, 2021
by Johnrocker
With every decision at the end of a chapter your game state can change. Here are your current variables.
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