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 the night shift at some job he got from his uncle. Andy always blamed his new job on why he didn’t want to have sex. He was always tired from the 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 fucked had his girlfriend unexpectantly come 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 if 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 cum.’ The moment where the boyfriend is caught getting fucked and cumming when the girlfriend comes in. It all made sense. Andy 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 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 X (Twitter) accounts devoted to sissy captions. Eva had 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, and 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. Eva went to the bathroom to talk to him. She normally talks to him while he gets up from sleeping. She opened the bathroom door. Andy was just in his boxers, and he was peeing. His dick was barely sticking out of his underwear.

“Morning love,” Eva said.

“Morning, babe,” Andy replied. 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. Could we get something to eat? Are you hungry?” he asked.

Eva thought for a second. She was never going to convince a man to fuck him like in the stories. People write those stories horned up with cum brains, full of leaps of faith. But she could still get what she wanted.

“How about we stay in?” she suggested. 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,” Andy complained.

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 get into her jammies.

“This one is so good. God, I can’t wait. This is the first one with zombie Jason in it!” Andy said.

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,” Eva said casually.

This was her play: direct. Play on the shame from the stories. Andy 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?” she asked with a raised eyebrow.

Still, Andy was silent.

“I saw how many times that story was in your browsing history. How many years you’d read that same story,” she continued.

He gave a panicked look at her.

“I found out what sissygasms are. Sissy Hypno. POV JOI Humiliation. Futa dickgirl traps,” Eva said.

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,” Eva asked.

Andy hemmed and hawed and was very uncomfortable. “I don’t know,” he eventually said.

“I think you do,” Eva countered. “I think you know exactly what you want. If you want it, you have to say it.”

Silence again.

“Tell me. Tell me now, or I’ll tell everyone. I took screenshots.”

She hadn’t, but she knew this would get him. He’d never want anyone to know this fucked up fetish, even if he ever came out as gay or bi or whatever.

“I want you to watch me have sex with someone,” Andy said red-faced.

“Who do you want me to watch you having sex with?” Eva asked, intrigued.

“Umm, it could probably be anyone. Someone feminine, preferably. Feminine and uhh… with a dick.”

“That wasn’t what was in the story. I saw your other searches, and that has girlfriends with strapons and trans women and crossdressers fucking straight men. Still, the story I read had a man like you getting caught by their girlfriend while cumming by getting fucked by a man.” She wasn’t positive, but it seemed like this was the most humiliating option and the correct option for his first time. “Tell me what you want.”

She continued to stroke his dick and balls, and her hand trailed underneath to his perineum. She always knew he liked this, and it makes so much sense now.

“OK, OK, OK, I want you to see me get turned out,” he confessed in a rush.

“Turned out?” Eva asked with a grimace.

“Yeah, like turned out, turned gay, made to be gay. I want you to make me gay.”

She knew this was what he was getting at from his search history, but she wasn’t positive. Especially since he’s asking for it, he’s already bi or gay or somewhere on the Kinsey Scale, but he wants her to ‘make’ him gay. Men.

“You want me to make you gay?” Eva asked.

“Yes, yes, I want you to make me gay,” Andy said, nodding.

She sipped her wine, and they sat in silence for a minute.

She got up, went to the bedroom, dug out their lube, and she pulled out her dildo. He always seemed weirded out by it because it was 7 inches long and thick and veiny and very lifelike. She pulled out her phone and turned it on record, then put it back in her pocket. She came back and stopped before entering the living room.

“Take your underwear off. Get down on the floor face down and put a pillow under your midsection so your ass will be in the air,” Eva ordered.

She heard him shuffle and then silence. She walked in, and he was waiting, and she could see his legs were already spread, and she could see his little dick and balls and his asshole spread, but he still had his underwear around his ankles. She sat down the lube and dildo, pulled out her phone, and placed it behind him where it would see everything on a side table. She started by caressing his perineum again. She did this slowly.

“So you want me to make you gay, eh?”

“Yes,” Andy said.

“And you want me to watch you have sex with men, anyone with a real cock that can fuck you?”

She let a finger caress his hole lightly and moved back down to his perineum and balls. She did not touch his dick.

“Yes,” he said breathlessly.

“And that could be anyone, and the most humiliating of them all because you like the humiliation, right?”

“Yes, I do,” Andy agreed.

She cracked open the lube and poured it on her finger and onto his manpussy. “And the one you want the most is who?” She started to rub the lube around his cheeks and balls.

“I’d prefer to start with someone more femme, like a crossdresser or a trans top,” he said.

She circled his asshole, and she could feel him motioning back to her finger. “But the most humiliating would be with a man, right? Letting me see you be a little pussy boy and taking cock from a big strong man and cumming from just his cock going into your asshole?” She slowly pressed her finger in just a little and pulled it back out. “That’d be the gayest thing you could really do, right?”

He whimpered and motioned his ass back to her finger again.

“Because that’s how this is going to happen. I’ve decided how to make this work for me.” She pushed her finger into the first knuckle. “You are going to do all the work. I’m not going to get a man to come fuck you. You are going to find a man to fuck you. You can tell him whatever you want, but he is going to fuck you. And I will be there to see it for some part. However, that happens to work for me. If you find someone hot enough, I’ll even let it be like that bull cuckold story, and he can fuck me and then fuck you.”

She pushed her finger in as far as it would go and left it there. Andy was motioning back and forth with his pelvis, fucking the pillow and fucking back into her finger.

“Do you want that, you sissy?” she asked. Andy moaned in a way she never heard him moan before. She started fucking him with her finger. “Do you like me fingering your fuckhole?”

He moaned again. Eva removed her finger from his ass.

“Please put it back in!” he begged.

“Do you like me fingering your fuckhole sissy?”

“Yes, I like you fingering my fuckhole. Please keep going!”

She inserted her finger back in, but slowly. “Do you like me calling you a sissy?” He nodded his head, and she could see his dick pulsate. “Would you like it if I called your dick a dicklette from now on?” He nodded his head again. “You know what I don’t touch though. I don’t touch dicklettes.”

He looked back for the first time since this all started. “You’ll never touch my cock again?”

“It’s not a cock, Andy. It’s a dicklette. It’s barely three fucking inches. Your balls are bigger than your dicklette.”

You could see him fighting for his masculinity now. He was fighting his cum brain or playing into the fantasy. It’s honestly hard to tell.

“I can stop if you want. I can pull my finger out of your ass, and I can try to pretend I never heard any of this, but I’m going to tell someone eventually. And then they’ll tell someone, and then everyone will know you want cock in your ass, and your too much of a sissy bitch to do it on your own, and you love that your dick is three inches, and you haven’t made me cum in months. Do you want that?” she asked.

“Please don’t do that, Eva. Please, please don’t, baby,” Andy begged.

She started inserting another finger into his asshole, very, very slowly, to the first knuckle again and waited there. “Andy, I want what I want. I want to get fucked. I’m so fucking sick of not cumming. You cum every time we play around. Did you know that?” She slowly eases in more of both fingers and starts to rub on his dick and balls while she does with her other hand. “Do you know I’ve only cum from masturbating for months? It might have been a whole year since you actually made me cum, and I had to work so fucking hard to make that happen.”

She slightly tugged on his dick and got both fingers in as far as she could and let them sit there so he would accommodate. She hadn’t thought any of this would be hot in the slightest, but it wasn’t bad. She liked the power of it. “I found out about your weird fucking fetish, and this gets us what we both want. Fucked. I was a little hurt at first, but we’ve been nearly done for the longest time.”

She felt him start to fuck back on her fingers. She wasn’t sure if she lost him, but the shame and humiliation and, honestly, the truth of it seemed to be working. “And now I know why you barely want to fuck me. Because you want to get fucked, don’t you?” She started fucking him with both fingers, in and out. “You want to get fucked and cum inside and turned out into a sissy fucking slut and not have to admit you want it, right?”

She stopped rubbing his dick, and he whimpered again. “You want to be a little fuck bitch and cum from having your ass fucked. That’s what your dicklette is saying.”

She grabbed the dildo with her free hand and rubbed it down along his ass through the lube and down to his dicklette. He didn’t say anything or seem to care that it had come into play. She pulled her fingers out of his fuckhole and grabbed the lube. She sees his asshole gape slightly for a second, and he turns around to see why she stopped, slightly knocked out of his cum craze.

“Eva, please, it’s just a fetish. I don’t want to leave you! I don’t want to see you get fucked by another guy!” Andy shouted.

“Andy, you shut the fuck up for a minute and listen to me.” She pours lube on the dildo. “I will never see you the same again. I wasn’t kidding when I said I’d never touch your dicklette again after tonight.” She rubs the dildo all over with the lube and puts more on his asshole. He’s quivering and shaking from how horny and turned on he is, and he hates that she can tell. “You’re a pathetic, thirty-three-year-old with nothing. We aren’t getting married. I’d already decided that before I found out you’re gay.”

“I’m not gay!” Andy snapped.

She placed the dildo near the entrance of his ass pussy and pushed it in ever so slightly.

“You’re not gay, eh?” she said mockingly.

“I’m not gay, Eva! It’s just a fucked up fucking fetish, ugh…”

She held the dildo in just at the tip of the head and started really jerking off his dicklette. More attention than it had had all night. She knew she’d have to be careful, or he’d cum and it’d be all over.

“You’re going to make a promise to me right now. Promise me-” Eva gently but firmly grabbed Andy by the balls with the dildo still held in place. “Promise me you’re going to stay pussy free from now on. That you’re going to fuck a real man. That you’re going to leave me after you do so and move out and live with this man and be his sissy bitch for as long as he’ll have you, and never pretend to be a real man again.” She pushed the dildo in a little further.

“Eva, I… love… you…” Andy squealed.

He could barely say the words, probably because she was still slowly pushing in the most realistic cock he’d ever hard in his ass to date, twice the size of his dicklette.

“You don’t love me. You love the idea of being a real man. But you’re a pussy free bitch, and I’m going to make sure you stay that way. Look at the side table by the couch.” She squeezed his balls a little tighter than she ever had before. He jumped up a bit, turned his head, and saw the phone camera pointed right at his hard little dicklette. “I’ll send that video to your Mom. Your Dad. Your sisters. Your best friend from college. Your one other ex-girlfriend.”

She could see he was getting a little emotional now, but it was too far now. She knew she was setting him free. “If you don’t promise to do everything I say, I will send that video to everyone you love. Suppose you don’t stay pussy free for the rest of your life and let one man at least fuck you once. In that case, everyone will know about your small dick humiliation. They’ll have to google what a femme boy is like I did today, and they’ll never talk to you again.”

He twitched like he would move to grab the phone, but she squeezed even further on his balls. “I’m recording this one on my phone to the cloud. You’ll never be able to delete the video.” She pushed the dildo in to close to five inches now. The balls of the realistic dildo were nearly at his own. “Promise me you’ll never fuck another woman again, and I’ll touch your dicklette one last time tonight, and no one will ever see the video.”

“I promise,” Andy shouted.

She let go of his balls and started stroking his pathetic little dick. “Promise you’ll be gay from now on and only take cock into your ass. Promise me the next time your dick is touched, it’s by a man. Promise me the only way you jerk off from now on is to gay porn. You never put that pathetic dicklette in any cis woman ever again, and I’ll make you cum one last time.”

She pushed the cock all the way into his ass, the balls of the dildo finally touching his own and furiously jerking off his tiny little fucking dick. He continued to moan, and he was about to cum. She screamed, “PROMISE ME!”

And let go of his dick again, leading to one of the worst ruined orgasms of his life. His tiny dicklette let out a tiny spurt of cum, and he had to do anything to finally cum.

“I PROMISE I’LL BE PUSSY FREE FOR THE REST OF MY LIFE. I SWEAR I’LL GET FUCKED AND TAKE DICK AND NEVER FUCK A PUSSY AGAIN. I SWEAR, I SWEAR, GOD PLEASE JUST LET ME CUM, BABY!”

She held the cock in and grabbed his dicklette for the last time and stroked it with the lube and a tiny amount of cum mixing.

“TELL ME YOU LOVE COCK AND HATE PUSSY!” Eva shouted.

“I LOVE COCK. I LOVE COCK IN MY ASS. I DON’T EVER WANT PUSSY AGAIN!” Andy responded.

She could feel his cock nearly vibrating from how much it was pulsating, he was going to cum any second, and she wanted him to never forget this cum, his last time coming with a woman. She started fucking his ass with the dildo.

“SWEAR YOU’LL NEVER TOUCH A PUSSY AGAIN, OR I’LL SHOW YOUR FATHER YOU’RE A FUCKING FAGGOT!”

“I SWEAR I’LL NEVER TOUCH A PUSSY AGAIN,” he promised.

He started shooting rope after rope of semen out of his tiny fucking pathetic dicklette. Eva let her hand go just as he started coming and started fucking in and out of his ass and grabbed his balls and pulled on them. She knew that he liked that. Eva wanted this moment of shame to be mixed with as much pleasure as it could while letting him shoot his load out of his dicklette without her touching it ever again, just pathetically twitching out pent-up cum by itself. She waited for the cum to stop, and she slowly pushed the cock all the way back into his ass. She wanted him to have to remove it after he came.

“Don’t you fucking move,” she said.

She got up, grabbed the phone, stopped the recording, and placed it back into her pocket while it finished uploading. She wasn’t happy about all the lube and sissy ass juice on it, but she would clean it later.

He was still coming out of cum-brain and entering post-nut clarity. “Holy fucking shit Eva.” Andy rolled over and looked up at her. “I’ve never cum that hard in my whole life. That was so fucking good, just like in the stories. Holy fucking shit.”

Eva grabbed her car keys and opened the blinds. She thrust open the front door. The dildo was still firmly lodged in his ass, and his underwear was around his ankles. He could barely stand due to the earth-shattering cum he just had.

“I’m going to Charlotte’s house and tell her we fought about money or something stupid,” Eva suddenly said.

He started to remove the dildo from his ass, but he stopped mid-stroke. “Wait, what?” he asked wide-eyed.

She pressed the panic button on the car keys, the sirens started blaring, and the neighbors started turning on their lights. Andy stayed down on the ground, away from the window, and held the dildo in place.

“You’re going to download Grindr tonight and make an account with your real photo and real name.”

He started to wiggle back on the floor away from the door and windows and tried to get his underwear on and dildo out of his ass at the same time.

Eva continued, “And you’re going to keep that dick in your ass the rest of the night. You’re going to go sit down and keep that dick in you and get used to it. You’ll have that dildo in you every day from now on. And if you get horny again from that dildo pressing on your prostate, you’ll jerk off to more of your fucked up sissy porn.”

She cut off the alarm as people started opening their front doors. She talks in a hushed tone. “You’ll never touch that dicklette again without a dick in your ass, real or fake. I wasn’t kidding, you’re staying pussy free. If you don’t want me to tell Charlotte and your parents the real reason I’m gone, you’ll message some men tonight. I don’t expect you to find dick by tomorrow, but you’ll work on this every day, or you’ll be pussy free, and everyone will know about your little dick and fucked up fantasies. Now put that cock back in your ass.”

Andy sat silent for a second but began to slide the dildo the rest of the way into his ass.

“Do you understand me?” Eva asked firmly. “Nod, yes, or I press the panic button again and scream.”

Andy nods furiously, holding the dildo in as far as it will go.

“Do everything I just said, or I swear your Mom and Dad will see your tiny dick coming and screaming you’ll be pussy free forever. Everything.” Eva goes to the door, puts on her shoes, and grabs her purse. “I’m doing this as much for me as I am for you, Andy. I want us both to be happy. You’ll see soon.”

Eva closes the door and leaves Andy on the floor in his cum and lube, sitting on the dildo and staring at the door as she cranks up the car and leaves.

 

To Be Continued…

 

*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.