Andy was a little pussy loser. Thirty three years old, a shitty job, and a three and a half inch dick.
Andy somehow had a long term girlfriend, Eva. Andy and Eva had been dating for four years. They had sex once a month, at best. Andy was bad at sex. Eva had never cum from having penetrative sex with Andy, and lately would barely cum when he went down on her or fingered her.
Eva couldn't keep living like this. Andy had no prospects of a better paying job, no inclination he intended to marry her, and she was fairly certain he no longer enjoyed vaginal sex. She had attempted to bring up seeing other people, but the time never felt right.
Andy didn't have a password on his phone, and didn't have the fingerprint lock on. Eva one day opened his phone and he still had his web browser opened up to a page on Literotica.com. Andy had been asleep for a while now, he was working night shift at some job he got from his uncle. He always blamed his new job on why he didn't want to have sex, he was always tired from night shift. He wouldn't be up for a few hours.
It was at the end of the story, page three. The part it was at was about a large man who was having sex with another man. They were having sex and the man getting fuckeds girlfriend came home. In the story the girlfriend could see her boyfriend getting fucked and the man fucking him was looking at her and smiling. She screams out, and the boyfriend turns around just as he starts to cum purely from being fucked in the ass by this larger man. The boyfriend tries to calm her down as he is still coming and looking back at her, and the man fucking him came as this was all happening.
She started looking at Alex's browser history. He had opened up this story after he got off work but before he came home. He must have jerked off somewhere before he came home. Other similar stories of men having sex with other men for the first time, sometimes with their girlfriends there watching them and getting cuckolded, as a part of a deal for the girlfriend gone wrong, or the girlfriend walks in and sees their boyfriend getting fucked and humiliates them.
Eva looked a little further and saw history on porn sites of people having 'sissygasms'. She had no idea what this was. A sissygasm is apparently when someone ejaculates from anal penetration only, and no stimulation to the penis. She saw searches for "POV JOI Humiliation", with videos of women telling men that they don't deserve "pussy", that they are homosexual or at least bisexual, making fun of their penis sizes, and telling them that they can't satisfy women so they should satisfy men. Also stories about crossdressers or even trans women fucking men and humiliating them while doing it.
This search history went far back. Back before they even got together.
Eva opened the story back up to where it was before, and thought for a second: this is where he came. The moment where the boyfriend is caught getting fucked and coming when the girlfriend comes in.
It all made sense. He barely looked at her when they did fuck. He had his eyes closed, and it took forever for him to cum. He's been jerking off to this, all of the time, and he's thinking about this to cum with her.
Eva put his phone down and went to grab her own and text her friend Charlotte to ask what to do when it hit her: Eva had her way out. She had felt so guilty about wanting to break up with Andy, but if she caught him having sex with another man she'd have to leave him. No one would feel bad for Andy. He'd never even be able to defend himself.
In some way she still kind of loved him, if she could lead him to the path he truly seems to want to take, maybe that would help him too. By doing this and breaking up with him she'd be helping him, and finally get fucked by a real man.
Eva turned on her private browser and started doing research. She had never read and looked at so much fetish porn and sex stories and twitter accounts devoted to sissy captions. She'd never seen anything like this in the porn she watched (mostly just vanilla hetero sex, the occasional lesbian video shot by and for women, and a mild interest in nipple play videos). She was reading up about futarni, fem boys, traps, and spent more time on 4chan than she was comfortable with.
She was listening to some sissy hypno videos when she noticed Andy had woken up and gone to the bathroom. She closed out of all of her tabs and tried to act natural. She went to the bathroom to talk to him, she normally talks to him while he gets up from sleeping.
She opened the bathroom door. He was just in his boxers, and he was peeing. His dick was barely sticking out of his underwear.
"Morning love."
"Morning babe."
He finished pissing and kicked off his boxers and she could smell the old cum smell on him.
"What were you wanting to do today? I know it's getting kind of late but I want to do something with my night off. We could go get something to eat? Are you hungry?"
Eva thought for a second. She was never going to convince a man to fuck him like in the stories. Those stories are written by people horned up with cum brain, full of leaps of faith.
But she could still get what she wanted.
"How about we stay in?"
Andy had a soft spot for cheap beer. Loved it. Would drink 18 of them in one night, easily. He was also much more pliable when he was drunk.
"I'll go grab some beer and wine for me, and some frozen pizzas. We'll watch a Friday the 13th movie even."
She hated horror movies and he was too dumb to notice that she was playing him instead of being nice.
"Yeah, sure, that sounds good too I guess. I am pretty tired. Fuckin' work and nights, Jesus."
She kissed him goodbye and looked at his little dick before she left the room.
"I'll be back soon little guy." She booped him on his small penis before leaving. She wasn't sure if she was being too overt or too coy, either way he didn't seem upset. Maybe he should be upset, who knows how this humiliation thing actually gets initiated.
She was thinking the whole drive how to make this plan work. It couldn't come on too forced, or at least she had to do it the right way if it was. He'd have to be horny to follow along with any of this. He'd have to have cum brain. She didn't know if she could get him to bring it up or not. He'd have to be drunk and have cum brain and asked the right questions, to make it seem like it was his idea. This wasn't a part of the fantasy in most of the stories, but that's the only way it would work. She went and got a twenty four pack of his favorite beer and the frozen pizzas and some red box wine and some sour gummy worms, mostly for herself.
When she came back he was on the couch, dressed, and he had his favorite Friday the 13th movie loaded and ready to play. She through the pizza in the preheated oven and brought him his beer. He slugged the first one back in the five minutes it took her to get her glass of wine poured and into her jammies.
"This one is so good, god I can't wait. This is the first one with zombie Jason in it!"
He hit play and she got him his next beer. And his next. She barely watched the movie because she hated it, she mostly looked at her phone and thought about how to make her move. She knew he didn't want to fuck, but she knew how to make him at least horny. She put her phone in her pajama pocket, got up and got him another beer, and he drank it and she thought and waited.
On his fifth beer she knew he'd be open. He was halfway through and watching intently when she laid her hand on his leg. She rubbed him slowly on the leg until he needed another beer, got it, gave it to him, and her hand went back a little higher up.
He loved having his balls and dick rubbed. He never said no to that. He might not fuck after, but his little dick would get hard. She started slow, with the balls, pulling them and his small dick out of the hole in his boxer briefs while working his dicklette.
He was enjoying it but he was also enjoying the beer. His dick was pretty much hard, as hard as it would normally get for her. He tried not to acknowledge her.
"I saw what you were jerking off to after work last night."
This was her play: direct. Play on the shame from the stories.
He was stone silent. His dick did get harder though, harder than she had seen it in a long time.
"Is that what you want? What was in that story?"
Still silent.
"I saw how many times that story was in your browsing history. How many years you'd read that same story."
He gave a panicked look at her.
"I found out what sissygasms are. Sissy hypno. POV JOI Humiliation. Futa dickgirl traps."
He backed away from her a little on the couch, and his balls were as tight to his body as they could be. His dick was red and purple and he was breathing very heavily. She went and got him another beer, cracked it for him, and handed it to him after taking his empty.
"Tell me what you want. I want you to tell me exactly what you want."
Andy hemmed and hawed and was very uncomfortable.
"...I don't know."
"I think you do. I think you know exactly what you want. If you want it you have to say it."
Silence again.
