Relationship Goals 4

By deepestshames.

Read Part 1 Here.
Read Part 2 Here.
Read Part 3 Here.


Part 4…

It had been two months since Eva had discovered Andy’s secret and he committed to being pussy free. Two months of jerking off to sissy and gay porn, two months of training his ass pussy with plugs and dildo’s, mostly staying in chastity, hell for the last three weeks she hadn’t let him out to encourage him to get out there and find someone to fuck the manhood out of him. Nothing.

It had begun to take it’s toll on both of them. He lost his job finally He said he kept making mistakes because he was so intensely horny all the time with the chastity on he couldn’t keep his mind on anything. That probably would have happened whether he was in chastity or not. He never held onto a job for long.

Money became tight. Eva made enough to be financially independent, but paying for Andy too was too much. This couldn’t go on much longer.

Eva was racking her brain on the situation on her way home from work one day, thinking about just going ahead and the bills and money and she saw her low air pressure light blinking on the dashboard. She started slowing down when she heard the wheels making a ka-chunk ka-chunk sound as she pulled over on the side of the highway.

She turned on her caution lights and looked to see if anyone was pulling up behind her and got out to check the situation.

Here passenger side rear tire was fucked. She didn’t know how she didn’t notice, but it was nearly completely gone, and she had been riding on the rim, which also looked fucked. It looked expensive.

She went to check her car insurance app on her phone to see if they did free tow jobs when she saw that she forgot to pay this month.

“Fuckin’ fuck!”

She kicked what was left of the tire and stubbed her toe.


She leaned back onto the car and eased herself to a kneeling position, examined her toe with her hand and sighed.

She pulled her phone out of her purse and started looking up tow companies when some blinking lights showed up on the road and started pulling up behind her car.

She stood up and shielded her eyes from their headlights to get a better look at them.

“Howdy! You need a hand?!”

The man spoke loudly over the engine, he shut the headlights off and parked, opened the door and got out. He was a relatively handsome older man, a bit of a pot belly but well kept.

“Yeah, I got a flat.”

The man walked over to Eva to access the damage.

“Ain’t no flat, damn tire is near gone.”

“Yeah I don’t know what happened, I just got a tire pressure low light and pulled over as soon as I noticed but this already happened.”

He bent down and inspected what was left, putting his hands on the rim and feeling around.

“Rim’s shot, you’ll have to get a new one. Might need a new rotor too.”

“Is that expensive?”

“Eh, you’re lookin at a grand and a half most likely with labor and parts, plus you’ll probably wanna replace another tire to even it out. Ain’t supposed to replace just one.”

Eva sighed and her head sank.

“I can’t afford a grand and half on this fucking car right now. My sissy ass boyfriend lost his job and I’ve been having to float him and me while he looks for something else.”

The mans ears perked up and he gave Eva a queer look.

“Sissy ass boyfriend?”

“Yeah I’m not very happy with him lately, he’s been-”

“You telling me your boyfriend is a sissy faggot?”

Eva didn’t really know how to handle this line of questioning.

“I’m sorry ma’am, my name is Bill. Yours is?”

He took off his work glove and stretched out his hand.


Eva took his hand and shook it.

“It’s nice to meet you Eva. Look here, I’m going to get to the point. If your boyfriend is a little bitch sissy and you’re willing to make a trade, I can fix your car free of charge.”

“Trade for what?”


Eva gave him a look, he looked alright but he wasn’t really her type.

“No, no not you! Him! Ass pussy!”

Eva still couldn’t believe this was happening, but it would really kill about four or five birds with one stone so she was willing to play ball.

“What can you tell me about the little sissy?”

“He’s in his early thirties, he’s been pussy free for two months and I keep him in chastity most of the time, I making him play with dildo’s and plugs mostly.”

“Interesting. Has he ever fucked another man?”

“No, never. It’s funny you should ask, I’ve been trying to get him to meet someone on Grindr or something but he never does.”

Bill let out a grunt.

“Oh yeah, a virgin sissy boy, yeah I’ll fix every bit of this tire and rim situation for a shot at that. You think he’d go for it?”

“I’ve had him in chastity for nearly three weeks now, I think he’d do about anything to get out at this point.”

“We got a deal?”

Bill held out his hand again, with a smile. Eva grabbed it again and noticed how massive his hands were, thinking about what he was going to do to her boyfriend with them.



Andy had been sitting at home all day waiting for Eva to get back. She texted him an hour or so earlier to get his ass ready, that she had a surprise for him tonight. He had nothing to do. No job, no friends, no way to jerk off. His mind was solely focused on sex. Any sex that could make him cum. He’d hoped that surprise meant him coming.

Ever since he lost his job Eva kept him in chastity as punishment. He hadn’t ejaculated properly in three weeks. He spent the first few days she was at work trying to get the cage off in earnest, but could never find the key and every time he tried to pry it off it hurt too much and he had to stop.

He tried in earnest to have a sissygasm. He tried every single day to pound his ass pussy hard enough that his prostate would release him from this hell but it never came. No relief. His normally small testicles had started to swell from the excess semen stored inside waiting for release.

Andy lubed his ass and the largest plug in his collection, and inserted it to the base quite easily. He had been working his way up since she texted through all of the plug sizes.

He saw flashing lights coming in through the windows, and heard a vehicle pull into the driveway that wasn’t Eva’s. He looked through the blinds and saw that her car was on a tow truck that pulled into the driveway. He quickly threw on a pair of sweatpants and a shirt and walked into the kitchen waiting for her to come in, feeling the plug every step of the way.

The keys jingled in the door and it opened, he saw Eva talking to the tow truck man for a second and she came in, leaving the door slightly ajar.

“What happened to the car?”

“Tire eroded somehow on the way home from work, it’s a long story.”

The door eased open and the tow truck driver eased his head in.

“Did he say yes?”

“Hold on Bill I just got in, give me a second.”

Eva went back to the door and whispered to him for a second and he nodded and she shut the door.

“Did I say yes to what?”

Eva came into the kitchen with a look on her face.

“Oh god you’re gonna fuck him to fix the car aren’t you?”

“No, no not that. Not that. Andy can you sit down?”

Eva pulled out a chair and sat down, and Andy followed suit.

“Andy, do you want to get out of chastity tonight?”

Andy wanted to get out of his chastity tonight, so he nodded.

“Well you know how money is tight lately since you lost your job? Well, this man outside, Bill, well he pulled over and towed me and we got to talking and he said he could make a trade to fix the car for free.”

There was a knock at the door.

“Give me a second Bill!”

They could hear Bill utter a response that sounded like it was in the affirmative.

“And he doesn’t want to fuck you?”

“No Andy, he wants to fuck you.”


“Think about it Andy! Do you have two grand lying around to fix that car? And if I can’t drive to work neither of us are making money. I have to get that car fixed.”

“But he’s got to fuck me?”

“Oh yeah, Bill made that very clear on the drive over. He kind of figured out you were a sissy and he made the offer, and it’s a hard one to refuse.”

“But you’ll let me out of chastity and he’ll fix the car?”

“Well, kind of, he’ll fix the car but he’s also stipulated that he’ll be the one to unlock you when the moment is right, he said. That was another caveat of his, but yeah, he said he’ll definitely let you cum, hell he wants you to cum. But he has to fuck you tonight or no deal.”

The door opened and Bill stuck his head in.

“What’d he say?”

“He said yes.”

“Wait a second Eva-”

“He seems like a nice guy, honestly probably better than any random person on Grindr, and I haven’t even been able to get you to do that. I hate to do this, but it’s either this or I leave and I send everyone the video of you begging to be pussy free.”

“That video is really hot by the way Andy, Eva showed it to me on the way over here. Told her I’d get her a whole new set of tires extra after seeing that.”

“See!? And a new set of tires! How could you say no!?”

Andy didn’t see any other way out of this. He looked over at Bill, now standing in the doorway looking at Andy in a way a man has never looked at Andy. Andy wasn’t totally turned off by Bill, he never really had an image of a man he would like to fuck, mostly he just thought about disembodied cocks with vague shadow forms, but Bill was not a disembodied cock at all.

“OK, so, I already told Bill about you wanting me to be there, and he’s fine with that, he says loads of sissies do that, it’s perfectly normal.”

Bill closed the door behind him and kicked off his shoes.

“Yeah, you’d hardly believe the amount of times I’ve done similar deals. Five or six times at least, it’s honest work. I personally enjoy it more when the wife or the girlfriend is there.”

Bill sat down on the couch and patted the cushion beside him.

“Come, sit.”

Andy walked over, feeling the plug in his ass for the first time since Eva came home as he did. He sat down and Bill edged over closer to him.

“Now, I know exactly how you feel. How you got here Andy. I see it all the time. You got a little dicklette and you feel inadequate with women don’t you son?”

Andy looked down at Bills pants and could see his erection forming in his pants.

“Are you going to do what I tell you to do if I let you out of that cage?”

Andy looked at Bill in the eyes for the first time.

“Yes, Yes I’ll do what you tell me to.”

“You’re going to have to call me Daddy for the rest of the night if you want that, can you do that son?”

“Yes D-daddy, I can call you Daddy.”

“Good, good. Get up and take off your pants and shirt.”

Andy got up, took off his shirt, and slowly eased down his sweats, bending over to take them from around his legs. As he bent over, Bill could see his plug in his ass.

“You been plugged up all day boy?”

“The last couple of hours or so Bill-Daddy.”

Andy sat back down beside Bill as he reached into his pocket and pulled out a key. The key. The chastity key.

“Now Eva there gave me this here key, and part of the deal is I get to take your dicklette out when I like. Ain’t that right Eva?”

Andy looked over to Eva, who was now sitting on the chair across from the couch.

“That’s right Bill.”

“And I like my boys to enjoy themselves, so I want to take your dicklette out. But you have to do what I say, you understand?”

Andy nodded.

“Yes Daddy.”

“Good. Now, she told me all about how you can’t fuck worth a damn. That your barely a man. That you got less than three inches of dick on you. Now, no woman wants that, now do they Eva.”

“No Andy, no woman does.”

“But you know who does want that son? Daddy does. Women don’t love little dicks, but Daddy sure does. I love seeing little dicks like yours swinging while their getting fucked, and other Daddies do too.”

Andy was blushing at this point, his balls bursting out from the ring in the chastity and his asshole was twitching.

“Women don’t desire you, but I do. Daddy does.”

Bill laid the key down on the end table by the couch. Bill undid his belt and his pants button.

“Unzip my pants and I’ll show you.”

Bill readjusted his legs and Andy timidly reached over and slowly pulled down on the zipper.

“Well you gotta pull it out.”

Andy pulled down on Bills briefs and reached his hand in to fish out Bills cock. He had to maneuver it but he got the eight inch girthy member out past the waistband as it seemed to get harder and harder.

“See? Your little dicklette all caged up and that plugged ass of yours did this.”

Andy noticed he kept his hand at the base of Bill’s cock and drew it back.

“Has he ever gotten you this hard, well, wet Eva?”

“He used to be good at eating pussy but not lately, no.”

“See son? See what you were meant to do?”

Bill got up and started to pull his pants down.

“Eva, do you mind if we start getting down to brass tax? I gotta get back on the road here in a little bit, dispatch is gonna have my ass if I don’t.”

“No Bill, please do.”

Bill took his shirt off and kicked his briefs and pants off, and sat back down beside Andy.

“Eva done told me that you are mostly in this to get fucked, and that’s fine by me, but you’re gonna suck this dick if you want that cage off. You want to suck Daddy’s dick?”

Andy was not at all into sucking dick but he didn’t think Bill much cared about that.

“Yes Daddy please let me suck your dick.”

Bill spread his legs wider, you could really see in how good of shape he was in. Muscular legs, and even though he had a pot belly he had pecs and well defined forearms. His balls were big too, lying on the couch under his massive erect eight inch veiny cock.

“Andy go on ahead and start sucking Bill’s dick.”

Andy reached out and grabbed the shaft again, leaned over and hovered his mouth over Bills dick. Andy opened his mouth and Bill could feel his hot breath on his cock.

Eva got up from the chair and pushed down on Andy’s head gently to force the head of the cock into his mouth. Andy closed his eyes and felt his tongue touching the cock and the hotness of it in his mouth.

“You’ve got to go up and down on it Andy, think about how I suck your little dicklette.”

Bill grunted.

“I’m sure there isn’t as much to suck there Eva.”

“Oh there isn’t. Do you remember how I sucked Damian’s dick Andy? Do it like that Andy.”

Andy thought back to all of the porn he’s watched and how his girlfriend sucked her ex’s dick and he started to mimic it as much as he could. He moved up and down with Eva’s hand guiding him, keeping his jaw as wide as possible trying to keep his teeth away from the mushroom head of Bills cock in his mouth.

“There you go boy, you’re doing just fine.”

Andy could feel a hand on his ass as he sucked Bill’s dick, it felt much rougher than Eva’s hand. He felt it toy with the plug in his ass, fingers pushing in on the plug and slowly pulling at it, back and forth, making Andy’s dicklette rage against his cage.

After a while Andy noticed Eva’s hand was no longer there as he kept bobbing up and down on Bills cock. He was starting to get more of his member in his mouth, close to half as he grabbed at the base of his dick.

“Play with his balls too Andy, you know how good that feels. Do what feels good on you.”

Andy grabbed Bills balls with his other hand, playing with them the best he could while slowly working the base of his shaft with the other and pulling his mouth off of Bills cock to lick it like Eva would do to him, like Eva did to Damian. Bill grunted in approval as he started to pull harder at the plug in Andy’s pussy.

“Oh god that’s not bad son ooooof. Uhh-uhh Eva, uhh could you bring me some lube?”

Eva got up and Andy put Bills dick back in his mouth, trying to continue at his previous pace but he stops when he feels the plug pop out of his ass suddenly.

“I didn’t say stop did I son?”

Bill throws the plug on the ground on Andy’s clothes and slaps him on the ass. Andy puts Bill’s cock back in his mouth and keeps sucking.

“Good boy.”

Eva walks back in the room and Bill holds out his hand, Eva squeezes some lube out and closes the bottle back and puts it by the chastity key on the end table. She sits back down on the chair, Andy looks over and see’s she is watching as he sucks Bills cock and Andy averts his eyes as he fills Bill start to rub the lube against his pussy with his massive fingers.

“Now your cock sucking isn’t too bad boy, but that’s not going to get you out of that there cage.”

Bill inserts the tip of his finger into Andy’s ass and Andy instinctively starts sucking cock harder than before.

“Unghhhh. Oh yeah keep doing that boy.”

Bill probes further into Andy’s asshole and Andy gets into a rhythm, getting back to playing with Bills balls as he notices how warm and humid they are in his hand. Bill starts wiggling his finger in Andy’s ass and he can feel it brush against his prostate, his sissy spot.

Bill takes his hand that isn’t in his pussy and pulls his head up to look at him.

“That’s enough cock sucking, I’m ready for the main event.”

He pulls his finger out of his ass and hands Andy the tube of lube beside him.

“Grease up my cock boy.”

Andy obediently opens the lube and pours it in his hand, cool at first. He starts to rub it all over Bills cock, from the tip to the base, making sure he gets it all over. Bill readjusts again, spreading his legs far apart as Andy finishes.

“Are you ready to become a faggot boy?”

“Yes Daddy, I’m ready to become a faggot.”

“I want you to sit on my cock. When your balls are resting on mine, I’ll be ready to let you out of that cage faggot.”

Andy didn’t need much encouragement. He had already sucked a dick tonight, and he didn’t even want to do that. He did want to feel Bills cock in him, feel it press against his prostate. He had begun to really start coming huge ropes of cum with the dildo in his ass when he jerked off so he knew if he got out of the cage he could do that again.

“Eva, are you ready?”

Eva pulled out her phone and pointed it to them. Andy didn’t care, didn’t question, didn’t even think, he just wanted to cum.

“Andy you need to grab the base and aim it towards your ass pussy ok?”

Andy got in front of Bill and grabbed the base of his dick and eased down as best he could until he felt the tip press against his pussy, his ass pussy. He slid up and down until he felt it near the opening and he started to ease back and sit slowly, feeling it open up his ass slowly. It didn’t feel anything like his plugs or his dildos, it was so much warmer and while firm and hard it had a give to it like nothing else he had ever had in his pussy.

Andy kept at it until he felt the full tip of Bills cock slide into his pussy. It was almost like a tiny plug, but the flared base was much wider. He sat there for a second and adjusted.

“You like that cock in your pussy boy? Do you like being gay?”

“Yes Daddy, I love your cock in my pussy. I love being gay.”

Andy started to slowly ease down in Bill’s cock. It hurt a little, it was bigger than his dildo, but he had prepared well enough today that he wasn’t in searing pain. He wanted to get to the base as fast as possible so he could finally cum, he had to cum.

He pressed down further and further past the discomfort and he felt Bill grab his thighs and pull him down for the final inch. The sudden rush of cock in his ass made him feel insanely full, and he sat there for a second as he felt his balls actually touch another mans balls below him. He felt Bill’s hands move, one grabbing his lock on his dicklette and the other going for the key.

“Are you ready to get out of that cage faggot?”

Andy could feel Bill’s cock twitching in his pussy.

“Yes Daddy please let me out of the cage Daddy!”

Bill put the key in the lock and left it for a second.

“Look at Eva, your girlfriend boy.”

Andy looked at Eva.

“Tell Eva your sorry that you’re a faggot sissy small dicked pussy and that you’ll never use your dicklette again.”

Andy looked past the phone to Eva’s eyes.

“I’m sorry I’m a faggot sissy small dicked pussy Eva. I’ll never use my dicklette again.”

Bill started to turn the key.

“Look at me boy.”

Andy turn his head back to Bill.

“Tell me you’re pussy is mine forever. Tell me you’ll never use your dicklette again.”

“My pussy is yours Daddy. I’ll never use my dicklette again Daddy. Please never let me use my dicklette again Daddy.”

Bill turned the key fully and free’d Andy’s dicklette. It had been so long since it was free, the cool air against it and the warmth of Bills hand with the cock in his ass created a wave of emotion in Andy was as in the moment as he could be. He could feel it growing in Bill’s hand, as Bill explored his balls and buried his face into his back.

Bill picked Andy up with his cock still in his ass and carried him to the bedroom. Andy looked back and saw Eva follow them there. Bill sat him down on the bed and grabbed his hips in the same way Damian did with Eva. Andy had always felt small with his dicklette, but never this small physically.

“Are you ready boy?”

“Yes Daddy!”

“What do you want?”

“Please fuck me Daddy!”

“Beg me to fuck you sissy faggot.”

Andy could see Eva out of the corner of his eye.

“Please Daddy please fuck me and breed me Daddy!”

Bill had let Andy control the pace up until this point but Bill began sawing into Andy hard. Andy could feel his little dicklette swaying back and forth as Bill’s balls started slapping against his ass. Bill grabs Andy by the back of the neck and continues at a punishing pace, every now and again Andy feels Bill’s balls slap his own as he fucks him.

Bill pulls out and grabs Andy’s shoulders and rotates him tot he missionary position. Bill glides his dick straight back into Andy’s pussy and starts jackhammering again, and Bill slaps Andy’s balls as he does.

“Oh my god that pussy is so tight boy! Unfff Unff-”

Bill sucks Andy’s neck and pulls back. He straightens up and pulls on Andy’s dicklette.

“I can’t believe you’d fuck anyone with this little thing you little faggot! Swear you’ll be pussy free for the rest of your life boy!”

Bill started pumping in a way that Andy recognized, Andy is sure Bill is about to pump his load into his pussy. He wants to cum while he does. He needs to get Bill to let him cum finally.

“Let me cum Daddy and I’ll be pussy free until I die! Please let me cum Daddy!”

“Swear you’ll never have children faggot! Swear you’ll never touch a pussy again!”

Bill started earnestly jerking Andy’s dicklette with his forefinger and thumb as he pumped his cock into Andy’s pussy. Andy started feeling his own orgasm rise, his toes starting to tense.

“I swear I’ll never even touch a pussy again Daddy please cum in my hole please breed be like a faggot Daddy!”

“Beg for me to breed your ass son!”

“Please breed be Daddy please breed me PLEASE!”


Andy felt Bill’s cock expand slightly as he held his cock in place and cum started spirting into his pussy, wave after wave of cum shooting deep inside his ass pussy.


Andy only took a few more jerks of his dicklette from until he started shooting cummies from his tiny pathetic dicklette, up to his face and hitting him on the cheek, rope after rope to his neck, chest, and finally to his belly button. Bill’s fingers left his dicklette quickly, and he eased his cock out of Andy’s faggot hole. He wiped his dick with the sheets on the bed, and stood for a second as he caught his breath.

“Fuck that was good, fuck. Eva, please send me that video at some point tonight.”

Bill started to walk out of the room as Andy’s post nut clarity hit him. He could feel his cum dripping down his face and his body and the cum beginning to ooze out of his ass. He’d finally become a sissy faggot.

“I’ll see you at the shop on Saturday Eva. Bring Andy by if you want anything else done.”

Andy sat up and watched as Bill walked down the hallway. He heard the rustling of bills pants and shirt and shoes and as Bill closed the front door. The tow truck rumbled to life and suddenly Andy and Eva were alone again.


To Be Continued…?


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