Read Part 1 Here.

*****

Part 2…

Andy was at a loss for what to do next. Eva had left for her friend Charlotte’s house, and he was no longer in the mood sexually. He’d downloaded Grindr and started a profile, but he didn’t finish all the setup steps to use it. He wasn’t feeling very hot or sexy or anything. And he was getting tired of having that dildo up his ass pussy.

He went ahead and took it out and took a shower. He always felt weird after jerking off to sissy porn. Post-nut clarity made him feel icky. This was another level he’d never reached before. He was completely released from his sexual desires and left with the memories of what Eva had said.

He didn’t really want to be pussy free. Not right now. He might want to be the next time he was horny for it, but right now, that wasn’t anything he wanted to even think about.

He washed away all the cum and the lube from his ass, and he washed the dildo too. He figured it’d be better to do it now than later. He got out, toweled off, and put the dildo on the counter to dry.

He put on his boxers and sat down in bed alone. He looked over at his phone and saw Eva had texted.

He opened it up, and the video she had sent had automatically started playing:

“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-”

He couldn’t take anymore and closed out of the video. He could see her hand holding the dildo into his ass and her holding onto his dick with his ass in the air. It was much better lit than he would have imagined.

The video did make his little dicklette leap to attention again, surprising for him since he rarely came twice in the same day when he fucked Eva.

Eva texted:

“I don’t see you on Grindr. I’m searching for you, and I don’t see you.”

Eva texted again:

“I’m sure Charlotte or your mom would love to see this. Maybe your brother-in-law in the military would think it’s cute too? If you don’t want to find out, just set up your profile.”

Andy sat in silence for a second and looked at the screen.

“And send me a photo of you with the dildo in your ass too.”

He went and grabbed another beer from the fridge and sipped it while he looked at sissy captions. He looks at posts about men trying to get sissies pregnant with their cum. He watches clittys bounce up and down as real men fuck their ass pussies. He drinks some more and gets in the mood. He has a full-on hard-on again, and he feels okay with continuing.

Andy goes back and grabs the dildo from the bathroom. He lubes it up and finds a JOI POV humiliation video of a woman telling him that he has a small dick and isn’t a man and should learn to love getting fucked by men if he can’t be a man to women.

He gets on all fours and proceeds to push the dildo back into his ass. It goes in easier this time than it did when Eva put it in. He wipes the lube off of his hands with a tissue and takes a photo of the dildo in his ass, and sends it to Eva.

“Sorry, I am finishing my profile now.”

He sends off his proof and finishes his profile and questionnaires for the app. He uses a slightly cropped photo of his face so people might not be able to recognize him. He waits for the app to load his profile, takes a screen grab, sends it to Eva, and can really feel how full he is from the dildo he’s sitting on. He’s not really fucking himself, but he does find himself readjusting and moving his hips.

Andy needed another beer, so he held his dildo in his ass while he walked to the kitchen and back. He grabbed two so he wouldn’t have to get up for a while. The dildo nearly slipped out, but he got it back in before it did.

He sat down and saw Eva had texted again:

“Good. You need to message at least one guy and send me a screenshot before you go to bed. Also, find some porn to jerk off to and send me a video of you cumming with the video in the shot, and there better not be any pussy on the screen.”

Andy looked around the people on the app and didn’t like anyone he saw. He saw buff dude after buff dude, and it wasn’t anything he wanted to fuck at all.

He started to look at porn to jerk off to on his computer and decided he would look at some trans porn. It was easier for him to get into. He looked and looked and found one he had watched before and really liked. Great camera angles always had the girl’s clitty on display, and you could see it bouncing from behind as the man fucked her ass. He really liked that.

Andy started on Grindr for trans women, but he didn’t see any that he thought he would click with. He looked and looked and kept watching his porn but decided he better message someone before he came and hit post-nut clarity again.

He finally just picked any man that he saw and messaged them to get it over with. He sent as thirsty a first message he could muster, took a screenshot, and sent it to Eva.

He then started stroking his dicklette to the video he was watching with the dildo firmly implanted into his ass pussy. He furiously jerked with two fingers and no lube for no more than forty seconds and grabbed his phone to take a video of him cumming. He barely got the video started before he started shooting his load, and some of it got on his laptop keyboard. He made sure you could see the video on his laptop screen in the background at the end. It was just a shot of a man fucking an ass with a little dick, so it technically fit Eva’s requirements. He sent her the video with no message included.

He heard a notification sound he never heard before and saw that the man he messaged replied. Still, Andy had now cum twice in one night and had no interest at all in talking to any man. He slowly pulled the dildo out of his ass again and had no will left in him to clean it tonight. He just laid it on an old pair of boxers and wiped the lube and cum up with a shirt, and laid down in bed. Eva never replied, and Andy fell asleep pretty quickly, pretty tired and drunk at this point.

*****

The front door opened and shut quickly. Andy stirred and took a second to register that Eva was home. Eva was home, and she knew about his secret fucked up porn shit. She had a video of him begging to be pussy free and a video of him cumming to gay porn, and he could feel dry lube and cum all over him. Andy got up and rushed to the shower, nearly stepping on the dildo he fucked himself with last night. He picked that up so he could clean it again and rushed to the shower. He didn’t see Eva before he shut the door. Maybe she was already there and left.

He showered and cleaned up the dildo quickly, dried off, got on some sweatpants and a shirt, and walked into the kitchen.

Eva was making eggs and toast. It looked like enough for both of them. There was a bag by the door, a gift bag in all black with red tissue paper sticking out so you couldn’t see what was inside.

“Morning.”

“Oh hey, morning.”

She kissed him on the cheek, which he didn’t expect.

He sat down, and she plated up the eggs, buttered the toast, sat it down in front of him, and sat down herself. They started eating.

He at a forkful of eggs and stopped.

“Hey, so-”

“About last night?”

Andy put his fork down and looked at Eva.

“I don’t know if that was exactly what you were looking for, but it seemed like you liked it.”

Andy didn’t know what to say. He had never really talked about this with anyone. It was even harder sober and a little hungover.


”You liked it though, didn’t you?”

“Yes. I did like it.”

“Tell me what you liked.”

Andy thought for a second, stirred around his eggs, and picked up his toast.

“Take off your sweatpants and tell me what you liked.”

He sat confused for a second and sat up to slide off his sweatpants, revealing his little dicklette and balls to her as he sat back down.

“I liked you making me say those things. I liked that it sounded like you meant it. You made it sound so real. Just like in the stories.”

“Liked that I made you say what?”

Andy hesitated and bit his toast.

“That you’d make me pussy free and never touch my dick or my dicklette again.”

Eva looked under the table to see his dicklette raging hard, having to say these things out loud. She finished her eggs and started to rub some butter and raspberry jam on her toast.

“Do you think you deserve to have sex with women?”

“No. Not really.”

“How long have you felt this way?”

“A while now. I’m not really sure. I’d always felt inadequate, but I’d never really made up my mind that I wanted to be pussy free. It came to me over time.”

“From the porn?”

“I guess. I don’t know if it started from the porn, or I sought it out because I felt that way.”

Eva kept eating her toast, and Andy just sat there, trying not to look her directly in the eye but in her general direction.

“I love you, Andy, but I need you to be honest with me. Do you want to be pussy free? You can tell me.”

“I, uh, I don’t know.”

Andy didn’t feel like eating anymore.

“What do you think about it?”

Eva got up and started a water kettle to boil, grabbing the coffee container.

“I think you should do it.”

Eva took out a coffee filter and, placed it in the Chemex, started grabbing coffee cups from the cupboard.

“You’re meant to be pussy free, Andy. I couldn’t have told you that before finding out what that was, but it makes everything make sense. You were meant to be a bottom bitch with that little dick of yours.”

“Are you just saying this because of the things you read online? The porn? You still sound like in the stories, and it’s very confusing.”

The water was starting to stir in the kettle.

“I want you to be gay, Andy. Because I think you are gay. You are gay, Andy. Look at your little dicklette right now, as I’m saying it. It’s twitching raging hard right now, and all I’m doing is calling you gay.”

She was right; he looked down, and it was throbbing.

“I want you to be you, and whether you like it or not, you want to be gay.”

The water kettle started boiling and cut off. She rinsed the filter and poured it out, then poured the coffee into the filter and started brewing the coffee. Andy didn’t want to say anything else.

“Tell me you’ve never put something in your ass before last night. Was that the first time?”

“no.”

“When was the first time?”

“When I was fifteen.”

She finished pouring the water into the Chemex and gave it a swirl.

“Have you used my dildo before?”

“Yes, but I cleaned it off really well, I swear. You were on a trip with Charlotte for a few days, and I used it after reading a bunch of fucked up erotica and watching fucked up porn.”

She got out the half-and-half and poured it into his cup. She drank hers black.

“When was the last time you jerked off to straight porn? Or lesbian porn even?”

“I honestly couldn’t tell you.”

She waited for the coffee to finish brewing, pulled out the grounds in the filter, and threw it in the trash. She poured them each a cup and handed it to him.

“Do you think you’re straight?”

Andy sipped a little coffee, but it was too hot. He blew on it and let it sit.

“Do you?”

“Sometimes.”

Eva blew on her coffee and took a sip. She let out a breath, took a breath, and looked at him in the eye as he looked past her. She looked like she could cry, but she didn’t want to.

“You aren’t there when we fuck Andy. You’re not. You are somewhere else. And for a while, I thought you were fucking some Instagram model in your head to cum with me. That fucked with me, Andy. Made me feel like I wasn’t enough. It wasn’t pretty enough. It wasn’t thin enough. Wasn’t enough to make you cum.”

Andy felt like a kid again. He felt like he was small, and he felt too truthful, and he felt like he was put on the spot, and he didn’t like it.

“Finding out that you were gay was a relief, Andy. It wasn’t me because I was never going to be enough. I wasn’t what you wanted.”

Andy sipped his coffee again, cool enough now to take a larger sip.

“You want dick. You don’t want women. You don’t want pussy. You read about it and jerk off to women finding out that their boyfriends are gay. Would a straight man do that?”

She drank some of her coffee and looked away, annoyed because he always got quiet when they talked about anything serious.

“I’m tired of feeling like I’m not good enough, I’m not worth fucking, and I want dick. I want real dick. Do you think you want dick? Why do you think I have a dildo that’s over twice your size?”

“I’m sorry. I’m so sorry.”

Eva got up and grabbed the black gift bag with the red tissue paper sticking out.

“Before I went to Charlottes last night, I grabbed some things. Things I think you need.”

She took out the tissue paper and almost took something out of the bag before she stopped.

“I still love you, so I am going to give you an option. I can leave right now. I’m not going to send the video or anything. I won’t tell anyone you are gay. But I’m gone. We are done.”

“Eva, please-”

“I’m not finished. We can be broken up, and you can jerk off to your porn, and I can go get fucked or-”

She pulls out something he’d only ever seen online, in porn and photos and drawings, but never in real life.

“Or you can let me lock your dicklette up and become the sissy you want to be.”

It was one of the nice metal ones, all silver and much smaller looking than he’d imagined them.

“I’d still be in your life. We can still live together for a while. And I have some rules you’d have to follow.”

“Like what rules?”

“You’ll find out after you’re locked up. That’s the deal. I can leave, or you can get locked up and do what I say.”

Andy drank more coffee and felt his raging erection and balls in the open air and didn’t want to think.

She started to take off her clothes, first, her top, revealing her breasts, and then taking off her pants and panties. She stood in the kitchen naked and looked at him. She picked up her phone, took a nude selfie, and sat it back down. His penis which slowly began to wither.

She grabbed the cage and knelt to his limp dicklette, almost shriveled inside of him at this point.

“You tell me when to stop.”

She took a ring and pulled it through his penis. Once at the base, she pulled through one testicle at a time until everything was in place.

She looked up at him, and he looked away, averting his gaze.

She placed the cage over his dicklette and lined up the pins on the ring to the cage. Carefully, she lined up the lock into the hole and held it for a second before closing it shut.

“Look at me.”

He looked up from his penis inside the cage in her hands and looked her in the eyes. She took his hand in her other hand as she held the lock.

She snapped the lock shut.

He started to get an erection again, his dick slowly rising and starting to fight against the cage, straining. He could feel the chastity device being filled and his penis being resisted, not being able to do what it naturally had his whole life.

“How does it feel? Does it pinch or anything?”

“It feels a little tight, I suppose.”

“How do you feel?”

He didn’t answer that.

“What I said last night, about getting a man to fuck you, about making you find a man to fuck you, that was true. But since you want to stay together, that means we’ve got to be in an open relationship for now, at least, right? Especially if we aren’t fucking, since you can’t fuck.”

She went to get his phone and grabbed her own.

“If you can get a man to come and fuck you, I’ll watch him fuck you. I’ll help in any way I can.”

She hands him his phone.

“But if I can get a man to come over and fuck me, you’ll have to watch.”

“Eva, that’s fucking crazy get this-”

“Andy, we made a deal, and I’m going to keep you pussy free. I do not have that key. I left it at Charlotte’s.”

Eva flicked his cage.

“The deal was I leave you, and I wouldn’t send anyone the video. You can’t back out of anything from this point on. If you do, I send the video to your boss, your best friend, and everyone. I even gave you a head start last night. Did that man message you back?”

He opened Grindr and checked his messages, and he had replied. He opened it up, and it was a dick pic with no text. He couldn’t think of anything to say back.

Eva started texting someone quickly. He couldn’t tell if she was on an app or if it was someone she already knew. She put down her phone and grabbed something else out of her bag: a nondescript box and a new tube of lube. She opened it up, and inside was a set of three anal plugs.

“Take off your shirt and get on the couch with your ass in the air.”

Andy didn’t really know how to make this situation any better, so he complied. Getting up and walking to the couch was an odd feeling with the cage on. Every step made it hard to ignore its presence.

She came over with the smallest plug and the lube and sat down beside him. She started by pouring the lube directly onto his ass pussy. She slowly started rubbing the tip of the plug near his sissy hole and down to his balls, lingering near his perineum every time she did.

“I talked with Charlotte last night. Not really about this, but just about what I’m not getting from you.”

She teased at his hole again but didn’t press it in at all, just circled.

“And she mentioned that my stories about you versus my ex, Damian, are like night and day. Even when I sugarcoat our sex life, she can tell Damian did it better, way better.”

She slowly started to press the plug-in.

“And don’t get me wrong, I don’t want to get back together with Damian, he was a fucking asshole. But he is currently single and ten minutes away, and he never stopped sending me dick pics, ever.”

The plug slid in pretty smoothly; it was pretty small, and he had that dildo in him a lot of the night before. Her phone buzzed, and a notification popped up on her screen.

“I think this would be good for you too. I think you need to see that you aren’t a real man.”

She slid the plug all the way in, and Andy felt extremely full and frustrated and emasculated and horny. She picked up her phone and read the notification.

“And he’s on his way over. I just sent him that selfie of me in the kitchen and our address, and it was that easy. It might be that easy for you, too, if you actually tried, real men love to fuck. It doesn’t take much. I almost forgot that. You can sit down normally now if you want to. I dunno if you want Damian seeing you with your ass plugged in the air, he’ll be here soon.”

Andy sat down, feeling the plug push in almost even further and his penis straining against the cage. Eva started tidying up the apartment, putting up the plates from breakfast, finished her coffee, went and pissed and flushed. Andy didn’t know what to do, so he just sat.

The doorbell rang. Eva grabbed a robe and put it on.

“You sit there and wait.”

Eva opened the door. Andy couldn’t really see him, but he knew what he looked like. He had seen photos of him stalking his social media to find out more about him. He’d always been insecure about her exes.

“Hi, Damian.”

Damian quickly rushed into the apartment door, grabbing Eva on both her ass cheeks under the robe, lifting it as he did, and started to kiss her. She stood up on her tippy toes and held her arms around his neck, and he started to close the door when he saw Andy with a silver thing on his dick, sitting naked on the couch.

Damian broke the kiss and looked over at Andy, hands still on her ass though.

“Goddamnit, you got me over here to cuck this guy, didn’t you!? You fuckin conniving bitch!”

“Damian, be quiet for a second, please. Damian, this is Andy, Andy, this is Damian.”

Andy slightly nodded at Damian, and Damian gave a half-hearted wave back, a hand still not far from Eva’s ass.

“Andy is my boyfriend who is coming to terms with his sexuality. The only reason you are going to fuck me is if you listen to what I say, Damian. I could get Josh over here to fuck me if I need to.”

“Fuckin Josh Josh? Josh, you left me for Josh.

“Yeah, Josh, Josh.”

“Fuck, fuck okay, okay. I swear to Christ, you’re the third bitch to get me to cuck their husband.”

“Andy’s not my husband, he’s my gay boyfriend, and you’re not here to cuck Andy, you’re here to show him how a real man fucks.”

“That’s what cucking is, isn’t it?”

Damian looks at Andy, and Andy looks just as confused as him.

“Shut the fuck up and fuck me.”

Damian looks confused at Andy one last time and back at Eva as she grabs at his crotch and starts to undo his belt.

Damian kicks into gear at this point. Damian takes off Eva’s robe as Eva undoes his jeans and slides them down. She gets on her knees and rips down his boxers.

Damian has an impressive penis. It’s nearly the same size as Eva’s dildo, around seven inches if Andy had to guess, but thicker and much more real and veiny and real. Eva takes no time before she starts sucking Damian off, grabbing the base of his shaft while she does, and he grabs the back of her head and eases her head back and forth.

Andy was never wild about cuckolding stories where the man watches his wife get fucked. He didn’t hate them, but they weren’t anything he jerked off to. He was turned on, as well as sad, to see his girlfriend of four years sucking another man’s dick. Another man’s dick is twice his size. She hadn’t sucked his dick in well over a year. He missed that.

Damian took over and pulled her head back, redirected her to get down on her hands and knees, and got behind her. He pushed her back down to the ground, leveraged her ass up, and looked over at the couch Andy was sitting on. He reached over and snagged a pillow, put it under Eva’s hips, and grabbed her hips with both hands. He directed his dick into her pussy with ease in one smooth, practiced motion.

The fucking was intense. It was like porn in some ways but more tender. You could see they had a previous connection, and he knew the things she liked. Damian held her hips with one hand and rubbed her nipples with the other. He would sometimes slightly tug on her hair, and she would crack a soft smile and moan like Andy had never heard. Made him wonder if she ever truly moaned with her. Damian even put one of his thumbs in her mouth, she sucked it, and after a minute, he pulled it out and pressed it into her asshole. She never said she liked that before. Andy could see the thumb go in ever so slightly at first and then all the way to the first joint and stop. Damian kept his other hand firmly grasped around her hips.

“OH FUCK THAT FEELS SO FUCKING GOOD FUCK”

Damian pulled his thumb out of her ass and grabbed her waist with that hand when he reached down with his other hand and started rubbing her clit. Andy was pretty sure Damian was about to cum, and he knew for sure Eva would never cum in time with him at the rate he was-

“FUCK I’M GONNA CUM. PLEASE DON’T STOP PLEASE PLEASE PLEASE PLEASE”

Eva started shuddering uncontrollably. Her hips bucked, and her back arched, and she never even had to touch herself once as she did with me. She came so easily.

Damian pulled his hand back, grabbed her hips with both hands, and started grunting and tensing as he pulled her in as close to him as he could. He must have been coming.

He held her there, and he slowly sank into her and onto her back, grabbing her tits and keeping himself inside of her.

Eva patted him on the arm and signaled for him to get up. Damian started to gain his post-nut clarity and tried not to look in Andy’s direction. He grabbed his boxers and slid them on quickly, nearly tripping and falling over. Eva got her robe and put it on but didn’t close it all the way, so her breasts were still fully exposed.

“Don’t send me any more dick pics unless I ask you to Damian. You can go now.”

Damian slid up his pants, buckled his belt, and looked around for his shirt.

“Fuckin cucks man, kick a man out immediately, fucking using guys fuckin-”

Damian pulled down his shirt and walked out the door, slamming it behind him.

Andy could hear Damian back out and drive away as he looked at Eva with her hair tussled and tits out and looking down at him with a look of disdain.

Eva walked to the bathroom, and Andy heard her start the shower. Andy wanted nothing more than to jerk off at this moment, and he tried to rub his dicklette while the shower was running, but that didn’t work. He couldn’t jerk off. He couldn’t cum.

 

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.