This is my first attempt at story writing, so please feel free to give me feedback and criticism!
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Amy and Brett had been dating since our freshman year of college, and both had never dated anyone else. Brett was the nerdy chubby kid in class, and considered himself lucky to be dating Amy. She was extremely attractive, skinny, had gorgeous brown hair, nice perky and firm 36C tits and a gorgeous hairy pussy. She was truly a dream for Brett. And he absolutely loved her.
Their typical routine was to head to Amy’s house after college let out and hang out together for a few hours until her mom got home from work, which usually consisted of them making out in the living room. Today was no different. They were laying on the ground, Amy’s tongue deep in Brett’s mouth as they kissed, her perky tits being explored by Brett’s hands, with her hand wrapped around his dick through his pants. Brett had been very open with Amy about his dick. It was only 3” long and very thin, and he absolutely loved being humiliated by her for it.
“You like me stroking your tiny little dicklett, Brett” Amy asked him between kisses. She knew he loved when she dirty talked to him. It took her a while to come around to Brett’s small penis humiliation kink, but she did enjoy how horny it made him and how much he seemed to like it. And as she did it more it become more natural to her, and let’s face it – he did in fact have a tiny dicklett.
“Oh God yes Amy, I love you stroking my tiny dicklett. It is so small. You deserve a much better dick than mine” Brett said nervously. He had been having fantasies about watching Amy with much bigger cocks after stumbling onto some cuckold porn. The idea of watching her suck a big cock, it reaching places in her mouth he had never been, or watching her tight hairy pussy being stretched to the point of not even feeling his tiny dicklett sent his mind into overdrive and always made him cum instantly. But he had never brought these fantasies up to Amy, so he wasn’t sure how she would react to what he said, but he was so horny in the moment that he couldn’t help but plant the seed and see what happened. He could always back peddle if he needed to.
“Mmmmmmmm, yea, do you think I deserve more than you pathetic little dick? You think I am worthy of so much more?” Amy whispered into his ear while she switched to stroking his dick with just 2 fingers. “I mean I only need to use 2 fingers to stroke your dicklett”.
That sent Brett over the edge and his cock erupted sending cum flying everywhere. Amy gasped as a stream hit her face and tits. She had never seen so much cum from his dick before. “Well I guess you liked that!” Amy exclaimed, rubbing some of the cum across her tits.
As Brett watched her, he decided now was his chance to feel it out. “You know Amy, I really meant it. I love the idea of watching you with a huge cock. The idea watching you be pleased in ways I never could. I mean I know we haven’t had sex yet or anything, but the idea of it all just makes me so horny”.
Amy just looks at him, “there’s no way that will happen. I am with you, and I only want you…tiny cock and all” as she gives him a wink and gets up to go clean herself off. Brett knows that Amy as always been open to his sexual kinks, but decided not to push the issue. He didn’t want to cause any problems. They spent the rest of the afternoon watching a movie and cuddling on the couch.
The next day Brett got to school and tried to find Amy like usual. He saw her from across the quad and was struck by how hot she was in her summer dress. It was accentuating every curve of her teen body, hugging her perky tits and her great ass. He looked down and just imagined that gorgeous hairy pussy under that dress. She made her way over to him and they kissed. “Good morning Brett!” She said. They went through the day business as usual and met up after school for him to give her a ride to her house.
When they got home they barely made it through the door before Amy turned around and started making out with him, pushing him against the door. She leaned away just a bit and pulled her summer dress down exposing just her perky tits. Brett couldn’t help but start to suck on her nipples while she ran her fingers through his hair. “I thought could do something new today” she said as she pulls him up into another tongue deep kiss. While they are kissing, Brett still leaning against the door, Amy slowly starts to lower Brett’s zipper and reaches into his boxers to start stroking his tiny dick. Brett let’s out a loud moan while they kiss as he feels her fingers wrap around his cock head, which is already slippery from precum from him picturing her in that summer dress all day.
All of a sudden she lets go of his dick and again leans back, looking him in the eyes with a smile. “I think you’ll enjoy this” she says as she slowly starts to kneel down in front of him. Her face is now eye level with the tip of Brett’s 3” dicklett and he can barely believe what is about to happen. She looks up at him and stares as she slowly opens her mouth leaning forward. Brett gasps as he feels his cock disappear into Amy’s mouth for the first time ever. Her tongue sliding along the bottom of his cock as she bobs up and down. He is in heaven.
“Are you liking me sucking your dick Brett?” Amy asks as she looks up at him. “Oh my God it feels so fucking good Amy, please don’t stop. Keep sucking by cock”. She smiles and leans back in taking his cock all of the way in and licking his balls. Brett moaned loudly, “fuck yes Amy, suck my cock!”
Amy pulls his cock all of the way out of her mouth and licks from his balls to the cock. “Do you wish I was sucking a bigger cock right now, Brett? Do you still want to watch me doing this to another guy? Instead of me doing this to your tiny dick?” She asks him while stroking his cock with two fingers.
“Fuuuck Amy, oh God yes”, Brett moaned hardly believing that was dirty talking like this. “I do Amy, I wish you were sucking a big dick right now. A real dick. Not my tiny little baby dick”.
Amy giggles a little bit as she is staring at Brett, gives him a little grin, “me too” she says as she engulfed his cock again in her mouth. She was sucking so hard Brett could hear the slurping sounds as she bobbed her head up and down. “I’m about to cum” Brett yells. Amy stops sucking and starts stroking him with two fingers. “That’s it baby, cum all over my face with that tiny dick. Only real dicks get to cum in my mouth”.
With that Brett couldn’t hold back anymore and felt the cum just start bursting from his cock. Shot after shot coats Amy’s face, dripping down from her nose onto her chin. Brett is catching his breath from how amazing this was, Amy stands up, gives him a quick kiss, and leaves the room to clean her face off without saying a word.
Brett is still standing against the door, his dick still hard as a rock as he replays all of this through his head. His first blowjob ever was incredible. And the dirty talk made it even better.
Amy comes back in, still in the sundress with her tits out on display. “So did you like that?” She asks.
“Uh, so fucking much!” Brett exclaims.
She walks closer, “I’ve been thinking about it, do you really want to watch me with a bigger cock? Why would you?”
Brett looks at her for a second, not sure if this is a trap, but again he decides to just go for it. “Yea, I really would. The idea of you with a cock that I can never have, a cock that you are worthy of is so hot. And I think the humiliation part is there. My tiny dick being ignored while you are with this real guy, it would be hot”
“But wouldn’t you want to break up with me? I mean, it is basically cheating on you?” Amy questions.
“Not at all! God I would love you even more, you would be even more perfect than you already are!”
She pauses for a bit, and he is afraid he may have pushed too hard as she looks unsure, “Who would you want it to be?”
Brett panicked. He knew who he wanted, but he didn’t want to tell her. He knew she hated the guy, but he also knew he really didn’t have much to lose at this point.
“Honestly, I would want it to be Justin” Brett whispered. Justin was Brett’s bully from high school who happened to live 4 doors down from Amy. He had always picked on Brett, was mean to him, and often called him a variety of names. But Brett loved the idea of Justin using Amy in ways he never could. And thanks to the urinals at school, he knew Justin was packing a very large cock. He could see the repulsion on Amy’s face. She hated Justin so much for bullying Brett all of the time, and couldn’t understand why Brett would say Justin.
“I know you hate him, I do too, but somehow if you were sucking his cock it’s like I win over him because I get to keep you! But the humiliation is there because he has something I can never have, a big cock that can please you in ways I can’t. Something about all of it just makes me super horny” Brett explains. He can see confusion on Amy’s face. But she leans in and gives him a kiss.
“Interesting” she says, and walks away. They go about the rest of the day like normal. Brett was at least glad she wasn’t mad.
A few weeks went by with Amy progressively talking more dirty to Brett, but not mentioning Justin specifically. She continues to ask if Brett was sure be wouldn’t be mad, wouldn’t break up with her, wouldn’t leave her. He reassured her, and told her he knew she wouldn’t do it, but loved the idea is all. They worked through scenarios while Amy was sucking his cock.
Summer was off to a good start for sure. One morning Amy sent Brett a text saying she was heading to the gym and that he should come over at 10 after she gets back from the gym.
A few minutes before 10 she sends him a text, “hey, I have a surprise for you, come in quietly when you get here”. Brett was confused, but just told her okay.
He pulls up to her house and walks in. She isn’t in the living room so he starts looking around when he hears her voice upstairs. He starts to head to the stairs and sees her clothes at the bottom of the stairs. Brett gets excited thinking about how maybe he was going to get to fuck Amy finally, she had been talking about finally having sex and Brett was excited to feel that hairy pussy.
He takes a few more steps up the stairs but stops suddenly. Brett hears another voice that he recognizes instantly. It is Justin. Is Amy upstairs naked with Justin Brett thinks to himself. He slowly climbs more but stops right as his head gets high enough to see into Amy’s room at the end of the hallway. He stops breathing when he sees it. There is Amy, standing totally naked in her doorway, facing Justin. Brett can only see a bit of Justin as he was in the room, but Amy was right in the doorway. Brett could feel his tiny dick going hard as he stared at the side of Amy, her perky tits and hairy pussy fully exposed to Justin, who was still fully clothed. A bush and tits that has only been seen by him otherwise.
“Damn, you are a hot little slut aren’t you? That little bitch Brett doesn’t deserve you. I always wondered why you were with that loser” Justin says to Amy as he reaches out and caresses her tits and let’s his hand drift down and brush against her bush.
“No he doesn’t, but he can’t know you are touching me, can we keep this a secret” Amy says to Justin.
“Oh absolutely, I have no problem enjoying you behind that losers back” Justin says. Without saying another word Amy leans in and starts to give Justin a kiss. He watches as they make out, tongues going back and forth for a solid 10 minutes. Justin using this time to grope Amy’s ass, tits, hair. Amy pulls away and slowly drops to her knees in front of Justin.
“Yea bitch, you want of my cock don’t you? Why don’t you go ahead and pull it out.” Brett watches as Amy slowly reaches out and slowly lowers his zipper. He watches as her hand disappears into his pants fishing for his cock. He sees her reaching further and further. Brett can’t take it anymore and pulls his tiny cock out too. Finally Amy frees Justin’s cock and he hears her gasp as it springs free. His cock is easily 8” long and thick. Brett watches as Amy falls back in shock, just staring at the massive piece of meat in front of her.
“It’s bigger than that losers isn’t it?” Justin asks.
“Yes, his is tiny. Yours is so much bigger. Nothing like his tiny little dicklett”. Brett shot cum out instantly hearing Amy tell his bully how tiny his dick was while she is completely naked in front of him with his cock inches from her face.
“That’s what I thought. This is what a real cock looks like. You know you want to suck it bitch”. Amy hated that Justin was talking to her like that, but she had to admit that his cock was incredible. It was much bigger than Brett’s, and she knew that he was looking just outside the door. “Kiss the tip of my cock bitch” Justin orders.
Brett watches as Amy nods, and slowly leans forward planting a kiss right on the tip of Justin’s massive cock head. Brett feels his tiny cock go instantly hard again. “Now kiss all of the way down to my balls” Justin orders again. Brett can’t believe what he is seeing as Amy keeps kissing Justin’s cock, working her way down the shaft to his huge hairy balls. “Good bitch, suck on my balls too”.
Without any hesitation Amy sucks one of his big balls into mouth and starts sucking it, stroking his monster cock with her hand. “So tell me bitch, I bet you aren’t used to having to use your whole hand around a cock are you?”
“No, usually I just use two fingers on Brett’s tiny dick”, while Brett starts using two fingers to jerk his dicklett, using his cum from before as lube.
Justin just laughs, “alright then bitch. Start sucking. Make a real cock cum”. Amy takes his dick into her mouth. She can only take about 4” of it before she gags. Brett has never made her gag before. Brett is stroking his tiny dick so hard watching his dream come true. Amy has a cock deeper in her mouth than he has ever been. Justin is feeling a part of Amy that Brett never has and never will. The thought of that makes Brett cum again.
“Good bitch, gag on my dick. Fuck your throat feels so good. Rub that tongue on my fucking cock you slut”. Justin places his hand on the top of her head. Brett watches as he holds her head still and slowly starts to rock his hips back and forth. Brett is watching as Justin is facefucking his girlfriend in her room. Brett could hear Justin’s breathing pick up. He could tell Justin was getting close to cumming.
Amy pulls her head away, looking out at Brett and making eye contact with him. “Cum in my mouth, make me swallow your cum. I only swallow cum from real cocks” Amy says as she is staring at Brett.
“That’s right bitch” just says as he grabs the back of Amy’s head and forces his cock back into her mouth. “Take my fucking cock, you love this cock. Not that tiny dick loser. I own this mouth. Fuuuuuck I’m going to cum. Swallow every single drop”.
Brett watches as he sees Justin’s cock pulse in Amy’s mouth knowing that he is shooting his load down her throat. She swallows every drop. Just pulls his cock from her mouth and her can see a string of his cum still going from her mouth to his cock and Amy is panting catching her breath.
“Give it another kiss slut”, and Amy leans forward kissing his cock head again while she stares at him.
“Brett’s going to be here soon, you need to leave before he gets here” she tells Justin.
“Alright, but I’m going to using that mouth more. So be ready” Brett hears Justin say as he heads down the stairs to hide before Justin sees him. He hides in the den as Justin heads past and out the back door. Brett rushes up stairs to find Amy standing in her door naked, smiling at him. He walks up and without even saying a word gives her a big kiss. He slides his tongue into her mouth as they kiss, tasting the saltiness that he knows is from Justin’s cum. Brett was so enthralled that he forgot his tiny cock was still out until be feels Amy start to stroke it with two fingers.
“You were right, I do deserve a big dick. And you get to cum now, but my mouth is only for real cocks” Amy says as Brett explodes into another orgasm shooting cum across the floor from his tiny dick. It was the best orgasm he had ever had.