Conjugal
A Short Story
By Maryanne Peters

We were brothers the way that real brothers never can be. We had been friends so long neither of us could remember our first meeting. With did everything together, we went to school together, we played sports together, we scored girls together, we did crime together.

I could not tell you how that started either. I did something, he did something, but then we did stuff together. It does not matter how it started. We were good at it. He was the brains, and he was big enough to be the muscle if we needed. I was the charmer, and the little guy nobody noticed - the one to get through the barriers and make the steal.

I am not talking about robbery or anything like that. I am talking about stealing the money nobody sees go missing. I am not about to tell you what we did, or how we did it. He worked it out, and ran all the programs, I just got them inside and kept them working.

I cannot tell you exactly what we do, because to give it away would be the end of it. It is all based on those who lose the money not realizing it until a whole bunch of it is gone, and then being too embarrassed to even report it. And if they were to, the police would in most cases be left scratching their heads and wondering what they were investigating.

We made money and we were never going to get caught. Not for what we did anyway. But when you start to commit crimes it is like the law does not apply to you. Not any law. Nate got nailed up for something that had nothing to do with what we were doing. His wife started seeing another guy so Nate dealt with it as a criminal might.

He tried to buy the guy off. He had the money. But it just did not go that way. He was in jail for up to five years and I was half a team and basically fucked. If we were going to keep making money, I needed him. I needed a clear line of communication

I made some calls. He said all the phone lines were monitored. I offered to visit. He said that visits were monitored too. “Only conjugal visits get privileged privacy,” he said. “Something about the sanctity of marriage or some shit. But I don’t want to see my bitch wife and she doesn’t want to see me. She has filed divorce papers.”

So what was I expected to do? Forget crime and get a job? All I knew was what we did, and without him we weren’t doing it.

Then I got a knock on the door and Nate’s wife is standing there. She said: “Nate told me that he was talking to you yesterday … well, he wants a conjugal visit but not with me. So you’re it. You’re on for next week, but first we have to get you ready.”

She just pushes past me into my place that slams large bag onto the table. Out spills a wig and some makeup and a frilly girl’s top.

“This is the last thing I am doing for him to get him to sign the papers,” she said. “You can be his girlfriend from now on. God knows you are closer to him than I ever was.”

Maybe I am not as smart as I think, but it was only then that I realized what she was talking about.

“Hang on a minute, you want me to dress up as a girl and go to see Nate as you?” I was still confused.

“Not me, you fool,” she said. “As his fiancée. The new girl in his life. The prison knows that we are over. I have handed over the privileges to Tammy. That would be you. I hope you like the name. We need to get you dressed up for a photo so you can get the fake ID lined up.”

It was not the first time that Nate had lined me up with something that caught me by surprise, but this time the surprise was a shock. And it kept being added to as she pulled from that bag other items, including a pair of fake breasts, and underpants with a padded butt.

“We can do it here on the kitchen table, but you had better shave down first,” she said. “Your whole body from the neck down. Your face I will deal with myself.” She was clearly in a hurry to get this done.

“Whole body? Why would I do that?”

“To get you girly, that’s why, Honey! You can only do this if you knock down what you have, and build somebody new from the ground up. And if you are thinking about dressing neck to knee, let me tell that every girl who turns up for a conjugal visit dresses like she wants a fuck, and all the guards know it. So I will make you look good for the ID but the look for the visit will be standard wanton slut.”

She went to work on me, and I let her. I realized that if I could get to see Nate once a week even if for less than an hour, we could make things work. All that was required was that I pass as a woman whenever I visited the prison. It seemed easy, but it wasn’t.

I was actually quite surprised to see that I made a pretty good-looking woman. It was something about my eyes and my lips, both inherited from my mother. Just a touch of makeup seemed to work miracles. I looked totally believable until I started walking or opened my mouth.

“We have to fix all of this and we don’t have much time,” Nate’s wife told me. “If you are serious you will need to work much harder. Listen to the way I talk. Watch the way I walk. Pay attention. Do you want to male this work?”

I did. This was the best way to get back to business.

By the time that the arranged conjugal visit came along I was ready. I was dressed in something skin-tight with the padded butt of full display, and the fake breasts looking very real and very large. I wore a wig that first visit and I was allowed to keep it on, but was told that wigs are not usually allowed.

I went into the appointed room with its double bed, and I waited for Nate to arrive.

The door opened and he saw me.

“Hot damn, Tammy you look so good I could eat you up,” he said with a grin. The guard had me stand back while they took off the chains around his ankles, then the had me step inside and close the door before they took his handcuffs off through the small hatch in the door. Unlike other cells in prison that hatch could also be shut from the inside.

“Tell me what you really think, Nate,” I said, when it seemed the guards had gone.

“I mean it,” he said. “You look great. Better than I had though you would. My ex has done a good job on you. Now let’s get down to work.”

It was like he had never gone to jail. It was like we were sitting in a room off the warehouse, not in the middle of state prison. We just went through everything we had too. We did not have the ability to drawn diagrams and make notes, but we had a policy of not doing that anyway. Things like that can be used as evidence. And it was not bad that we had limited time. We needed to go through things quickly.”

As we finished up we heard the guards knock for the last minute.

“I can’t wear a wig next week,” I told him.

“Get my ex to get you hair extensions,” he said. “I’ll pay for everything. And now start panting a little. Remember, for the last half hour I have been fucking the life out of you. Oh … and give me a kiss as you leave.”

There was another knock and he opened the screen on the window and had his hands re-cuffed. As he left, I did as e asked and planted a kiss on his lips. I thought that a little peck would not be sufficient, so I kissed him long and hard, but a Hollywood kiss with a closed mouth. I felt his mouth open a little and a tongue search for an opening. He was fooling with me!

The guard put a hand on his shoulder to pull him away. I was slightly relieved.

His ex-wife told me that she was prepared to give a little more help because she felt bad about abandoning Nate. It was just that she was not one of those girls who could wait for years. She arranged the appointment with the salon to have my hair extensions put in, and also to have a proper facial done.

“But you need to understand that a wigs with bangs can be taken off and put on the stand when you get home,” she warned. “Hair woven in will stay there. You will have to live with it. And a smooth face with shaped eyebrows and curled and tinted lashes will make it hard for you to pass as any normal male. You might pass as some effeminate gay man, if you can live with that?”

To be honest, I did not care. I had my network pressing on with plans as discussed with Nate. The guys I worked with would not care what I looked like so long as they knew I was back in contact with Nate and the old firm was back in business.

I told the guys that counted what was going on. So if anybody called up looking for Tammy, that would be me. That was how I was getting access to Nate.

But Nate’s ex was right, I was going to find out that it was easier to be her. I just wore gender neutral clothing and had to put up with being greeted in shops as “Miss”.

I was better prepared for my next visit to the conjugal suite. I greeted him with that Hollywood kiss and was quick to get rid of the guards so that I could get it on with my man.

“That hair looks great on you,” said Nate. “Get your ears pierced and I will get some nice earrings for you. I love the makeup. You could be a runway model, Tammy.”

I didn’t want to waste time, but he was complaining that I was so pretty I was turning him on. I could see it was true.

“You’re going to have to jack me off, Tammy,” he said, unzipping his pants.

“Hey, Nate! It’s me. Not Tammy, me!”

“I can’t help it,” he said. “You look so good, and not just because I am locked up. And I have to walk out here looking like I have had sex, and you should to.”

“I’m not going to jack you off, Buddy,” I said. “You will have to do that yourself. But do it quickly. We have lots to cover today.”

Nate told me that prison is a great place to plan criminal activities. You have time on your hands and access to experts. All you have to do is to keep all your information in your head or in jottings that nobody can understand. Then you need to pass on the thought and any diagrams to me, to put into effect.

What Nate had come up with was highly ingenious and involved, but it was also very successful. What it established was that working with Nate like this was going to make us both rich. All I had to do was keep up the regular meetings with him, keep him supplied with information and keep him on the job – keep him happy. That last part became my mission.

I had prepared myself to do the unthinkable on my next visit. I told him that we had done well with his last scheme and as a reward I was prepared to jack him off while looking him in the face, tossing my hair and puckering my lips. I would never have dreamed that I was capable of taking another man’s cock in my hand but somehow seeing Tammy’s hand with her pink fingernails and feeling her hair across my face made it seem as if it was not me, it was her.

I even moaned a little while Nate muttered – “That’s it baby. You’re just so hot you’re driving me crazy. Yeah, Baby, yeah. Wow, oh my God…!”

It seemed to me that if this was a partnership, then I was the junior partner. I was taking half the profits and keeping the other half for Nate, but I owed him more. A few minutes of pleasure was the least I could do.

“I’d like a picture of you for my cell,” he said. “Guys have photos of their girlfriends. Naked would be nice. Photoshopped I guess, but make it look real.”

I arranged it. I used a nude model with a good body but not an unrealistic one – normal sized tits, a soft flat belly and a trimmed muff, and my face. Nate loved it.

“Can we get you a body like this?” he said. “I know a guy who deals in steroids and hormones and stuff. He can get you what you need. I will arrange from here. You just need to pay. Take it out of my share.”

“No way. That would be a business expense. It comes off the top before we split.” That is what I said. Not “No way. I’m not taking hormones!” Like I said, I needed to keep him happy. And I was spending so much effort being Tammy it just seemed that hormones might make it easier. He did arrange them. They were patches under my breasts and pessaries to be shoved up my butt.

I had never pushed anything up my ass before I got those things. There were instructions that suggested lubricant and how to ensure that they were properly inserted so as to allow the absorption into the blood system from the anus. It sudden became obvious that that I could accept something inside me that way, if that was what Nate wanted to do.

We had done really well, with this job but time was running out and we needed to move onto something else. Nate knew it too, and he said he was working on something even better. It seemed to me that he needed to be encouraged, so I decided to offer him my ass.

I told him nothing about it, but I prepared myself and I had a tampon in and a panty liner on.

“Baby, you look great,” said Nate. Prison boxers and loose pants hide nothing, and I could see that he was turned on.

“Well, I have been using those pessaries you arranged, and my butt is looking round and soft,” I said. “Maybe you would like to check it out?”

I could see that he was going nuts with desire. For some reason that made me feel so good. He was nodded and panting like a puppy. I just turned around, flipped up my dress and slowly pulled down my pants so he could see the gel on my panty liner.

“Pull the cord and watch me open up,” I said, waving my butt and the string from the tampon.\

That thing came out ad his thing went in, and he was a happy as a man could be. I could hear him grunting and gasping, and I was in not real discomfort because of the preparation I had done. I was not expecting my own pleasure but hearing him happy seemed to give me a little of that. But I was not prepared for what happened next. A wave of pure pleasure came over me quite unlike anything that I had felt before. It was not like a male orgasm – it was something different. It seemed to last longer, and then it finished with a glob of jizz shooting out of my cock and across the cell just as he emptied his inside me.

It was an earth-shattering event, or at least for me it was.

It marked the end of my life as a man, although I did not know it quite at that point.

I turned to see the grin on his face, and I knew that I was smiling too. We still had some time allocated so we just lay on the conjugal bed together for a while, just looking at one another. Well, his hands were on me, but I was just looking at him. He seemed to me to be a completely different person. I had always admired him. Now I adored him.

“These titties are coming along nicely,” he said. “If you want implants maybe we could call those a business expense too.”

I just had to kiss him. I just had to show him that this was more than sex. This was something much deeper. We are a partnership, you see. He is the brains, and I do my best to facilitate what he dreams up, but my real function is to support him and keep him on the job – keep him happy.

And he won’t be locked up for much longer. He was just in a bad relationship. Now he is in a good one. And by the time her gets out on parole I will be fully healed down there, and we can then be married. It is what we both want, and the Parole Board will be happy too, as they have met me, and they approve.

It really is an endorsement of conjugal visitation. Some relationships are beneficial all round, not just for the parties to a relationship, but to society as a whole, disregarding the victims of our crimes, that is.

The End

© Maryanne Peters 2022

Author’s Note:
This is one of the stories from my nineteenth anthology on Amazon, and second collection of short stories on the theme of Crime and Criminal - Link: https://www.amazon.com/gp/product/B0BY5B83SZ