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Chapter 37
by
Jjaymes94
What’s the condition?
Cum deep inside her
Dean watched as his girlfriend, Brooke completely submit to his virgin roommate.
“You have to cum deep inside my pussy!” Brooke said.
Dean was shocked, that wasn’t the plan at all. What was happening? The plan was that she was going to have sex with Richard anally for his first time. Dean was frozen in the closet, was he supposed to come out and catch them? He would also be caught in that situation, he let too much go already without stepping it. His cock was still as hard as ever.
“But what if I get you pregnant?” Richard asked. “Don’t worry sweetie, I’m on birth control, now please fuck me.” Richard was hesitant, he didn’t know what he was doing, he was a virgin after all. Brooke stroked his cock, encouraging him to fuck her, she was almost begging for it.
Dean was unsure why Richard hasn’t enthusiastically said yes by now, what options were to be weighed right now? Brooke who is a hot woman wants to have sex with him, he would finally lose his virginity.
Brooke took initiative and pushed Richard on to the bed. She climbed on top of his hard cock, she rubbed it on the outside of her wet pussy. Richard’s toes curled from the pleasure. “It’s going to feel even better once your inside my pussy” She said, “So do you want to lose your virginity or not?” Brooke demanded.
Richard shook his head up and down. Brooke immediately lifted Richard’s big cock up and slowly lowered herself onto the head of his cock. “Oh my god!” Brooke said, you would have thought she was losing her virginity with that outburst. Brooke got no more than the head of Richard’s penis in so far. “Your cock is so thick!” Brooke said as she tried working herself onto his long cock. She had to pause a second, “I’m sorry” she said to Richard. “Are you okay?” He said to her. “It’s just that I’ve never had a cock this large, you’re stretching me out. It kind of hurts but in a good way” she reassured him. Brooke continued to work Richard’s dick into her pussy, she was about halfway down when she started moaning. Brooke was bouncing on only half of Richard’s big cock, he still wasn’t fully inside her.
Dean watched as Brooke moaned more on half of Richard’s cock than she ever has on his dick. Despite losing his virginity, Richard looked comfortable with Brooke riding his cock, he was experiencing what a vagina felt like on his cock for the first time but didn’t look like he was going to cum any time soon. His hand wandered to Brooke’s heavy chest, fondling her as she struggled with his cock.
Brooke tried working her way down Richard’s large cock but she didn’t look like she was getting anywhere. She wined on every downstroke unable to take more of Richard’s cock.
Brooke stopped once again, only half of Richard’s cock inside of her tight pussy. She apologized once again, this time she was out of breath, “I’m sorry… I’m trying…” she was struggling with his large cock but she was determined. She caught her breath then took a deep breath before impaling herself with Richard’s cock. All at once the last half of Richard’s cock entered Brooke, “oh fuck!” Brooke yelled. She collapsed on top of Richard, she was feeling pain and pleasure from the largest cock she’s ever had inside of her.
Richard now was feeling Brooke tight pussy around his entire cock. “I’m gonna cum… get off!” Richard said but Brooke was in no shape to move, he tried to push her but she stopped him. “Baby, let me get used to your size,” Brooke sounded in pain, she stayed frozen on top of Richard. “I can’t…” Richard started to say before grunting. “Cum deep inside my pussy, please?” Brooke said.
Richard began to twitch and his hips moved slightly as he filled Brooke up with cum. “Oh baby, fill me up!” She moaned. Dean could see that Brooke started playing with her clit. Richard was just breathing heavy now that his orgasm was over, his cock still fully inside Brooke.
Brooke finally was used to his size and started to slowly bounce on Richard’s cock. His cum starting to slowly ooze out of her pussy and down his cock. Brooke was getting herself off on Richard’s dick which didn’t seem to be getting soft anytime soon.
Brooke was hard a work riding Richard’s cock. Every stroke got longer and longer, his dick never seemed to end. Brooke must have cum a couple times in a row because her moans never ceased. Exhausted Brooke laid down on Richard but didn’t get off his cock.
“How was that?” Richard asked Brooke shyly, he had no idea what sex was like. Brooke laid there with her eyes shut trying to catch her breath. “That… was… the best sex I’ve ever had…” Brooke said, it sounded genuine too.
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A story about being a generous roommate
Dean and Brooke have been dating for quite some time now, completely comfortable together. They love to experiment in the bedroom and try anything. Richard is Dean’s nerdy roommate, they have know each other most of their lives with their parents being friends and neighbors. Dean feels bad for Richard because he has had no luck with the ladies. A virgin nerd who use to live in his parents basement until Dean was convinced by his own parents to have Richard move in with him. Dean figures he could help Richard out once more and share Brooke with him and tap into another sexual fetish of his... win-win? Right?
Updated on Jan 28, 2026
by Jjaymes94
Created on Sep 12, 2020
by Jjaymes94
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