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.
"FUCK!"
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."
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?"
"Pussy."
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.
"Deal."
-----------------
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."
"Uh-huh."
"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.
