Chapter 37
by
Jjaymes94
What’s the condition?
Anal (Main Storyline)
“You’re not allowed to fuck my pussy” Brooke grins in a playful manner.
“What? What do you mean, how else am I supposed to lose my virginity?” Richard says confused.
Dean can only think how naive Richard is. Dean knows what is coming next. He tries to control his breathing and be as quiet as possible. Brooke is still following the plan.
“Baby calm down, you’re gonna fuck me in my ass!” Brooke giggles with excitement. “I’m sure you’ll enjoy it.”
“But... why can’t I just fuck you, like normal... in your pussy?” Richard says. “It’s my first time...”
Brooke interrupts his stammering, “Because I say so baby, trust me!” She smiles at Richard. “I know it’s your first time, I’ll help you through everything.”
Richard looks to be thinking and doesn’t say anything, maybe he’s contemplating it.
Dean is starting to get annoyed and is getting limp, he just wants them to do it already. Meanwhile Brooke is stroking Richard’s dick waiting for an answer.
“Okay fine.” Richard finally says. Brooke jumps up with excitement and lets out a squeak. She really wanted this to happen. Dean’s heart sinks, it finally going to happen. Dean again is hit with an array of different feelings. He has never seen Brooke more excited than she is right now... his penis starts to stiffen again. He of course starts to jerk off, his roommate is going to lose his virginity to his girlfriend’s ass.
Brooke has already thought of how everything is going to go down. She tells Richard all the details on what to do and how to do it and she answers any questions he has.
Brooke directs Richard to stand up. She takes her place on her knees in front of him sucking and jerking his cock a little more making sure it’s well lubricated.
*slurp slurp*
Brooke then takes some of that spit and wipes it on her ass, fingering herself a little bit too.
“Are you ready daddy?” Brooke says as innocent as possible.
“Hell yeah” Richard is cocky again.
Brooke stands up and bends at the waist over top of the bed leaning her arms and resting her head there. She bends her knees a little bit to accommodate to Richard’s height. She turns back to him, “Okay I’m ready, do what I told you now.” Brooke says.
Richard moves towards Brooke’s ass which is sticking up in the air, her back arched, face laying on the bed. He strokes his cock in anticipation, Dean does the same from within the closet.
Richard lines up his cock with her asshole.
“Take it slow baby, remember?” Brooke tells him.
Richard nods his head in agreement and continues. His dick makes contact with Brooke, she grins with excitement. The way they are positioned gives Dean a perfect view of her ass and her face.
Richard applies a little pressure trying to push his cock into Brooke, she tries to relax to make it easier. The head of his cock slips in, they moan in unison. He pulls it out and slowly starts again. To fit such a massive cock into her asshole is going to take some time. Richard slowly works his way to get deeper into Brooke. So far only the head of his cock has made it in.
Richard pushes on inch by inch deeper and deeper, Brooke’s ass loosens as he gets about half the length of his cock.
Brooke interrupts, “Wait!” She seems to be in a little pain, “Stay there for a little.” Richard starts to quickens the pace but only going halfway into her. They trade moans back and forth as Richard fucks her ass.
Dean matches the pace they are going jerking off his own dick.
“Okay I’m ready for some more...” Brooke says sounding unsure of herself.
Richard keeping the same quick pace pushes a little more with each stroke. Every time he pushes a little deeper Brooke’s face winces, it hurts but the sounds she is making she seems to be enjoying it.
“Wow you’re so tight, this is amazing, it feels so good.” Richard says.
Brooke stops Richard’s progress again. Dean can see that he still has a couple inches before he is entirely in. Richard has somewhat of an annoyed face, he wants to just fuck her fully already.
Richard has no patience, he slaps Brooke hard on the ass, she yelps. Richard pulls his cock out so the tip was all that’s left inside and rams it as deep as possible, she moans with pleasure. His thighs hit the back of her’s, his ballsack smacks against her wet pussy. She falls onto the edge of the bed no longer being supported by her feet or arms. Richard pins her against the bed. He pulls out and rams all of his cock into her again. Brooke doesn’t protest. He quickens the pace, fucking her furiously. Dean completely wide-eyed jerking his cock, he can’t believe what he is seeing.
Brooke screams “Yes” with every deep stroke with Richard replying with grunts. Richard slaps her ass again, she clenches her butt tightening on his cock which only makes him pump harder. Brooke is in a constant state of moaning at this point, her face filled with ecstasy. Dean can’t take it anymore, he bites his lip and cums in the closet, again, no way he was heard with how loud Brooke was being and the slapping of their skin together.
Richard seemed to be getting close at this point. Brooke could sense when he was about to come. “Cum in my ass, please please please.” She begged. Richard pumped hard and pushed his giant cock as deep as it could go. He groan and collapsed on to Brooke unloading his seed deep in her ass. Richard laid on top of Brooke, his butt clenching for a minute as Brooke’s ass squeezed all of his cum out.
Both of their bodies were covered with sweat and breathing heavy. Richard still laid on top of Brooke with his penis deep inside her.
Finally Richard gets up and slowly pulls his cock out. Brooke curses and moans a little when he is completely out of her. Richard lays on the bed with a big smile on his face and puts his hands behind his head, fully relaxed. Brooke slowly crawls up the bed and cuddles up next to him putting her head on his chest. He puts his arms around her.
Richard turns to her and says, “How was that?”
Brooke answers, “For your first time? That was perfect.”
They share a kiss.
Dean watches from the closet.
What's next?
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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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