Accepting a New Role

My name is Chris, and I had just separated from my wife of several years (Stephanie) and she had temporarily moved to her parents' place a few hours away. She had packed up some essentials, but left most of her stuff behind, planning to come back after getting her own place.

I was left home alone with a lot of time to think about what went wrong. One thing she said to me in one of our last fights kept replaying in my head. "Maybe you're a fag and that's why you can't keep it up or ever last long enough give me an orgasm." I didn't respond to that (which I think was more designed to hurt me than be a real accusation about my sexuality), but she'd hit closer to the mark than she probably realized. The truth was, I had fantasized about being with another man since middle school, and probably masturbated more times during my marriage to the thought of being with another man than the number of times I'd actually made love to my wife.

While part of me wanted to try to get her back and make it work, part of me felt like I had failed at being a heterosexual husband, maybe it was time to try something new, and maybe I had been lying to myself that I was bisexual but mostly straight who just had some strange fantasies that he'd never act on. I worked up some courage and registered on a dating site as bisexual, and after some deliberation, listed myself as a versatile bottom (although almost all my fantasies involved me exclusively as a bottom, maybe I couldn't fully admit that online). After a few weeks, I got a message from a good looking guy. (It was weird for me to think that, because despite all my fantasies, I never found myself actually attracted to men in real life, and didn't really consider myself "emotionally attracted" to men.)

His name was Jim, and he was about 45 years old, 6'4, 225 pounds, dark hair and a salt and pepper, neatly trimmed beard, and said he was a psychologist. (I on the other hand was a fairly petite 5'8", and about 155 pounds, with no facial hair and about 35 years old.) His profile said he was a top. I guess you could say he was a "bear" and I was a "twink" (which is embarrassing to admit). My heart was racing when I agreed to meet him for dinner on a Friday night.

We met at the restaurant and I was a little self-conscious when he gave me a hug and a kiss on the cheek before we sat down. I had never even told anyone that I had any gay fantasies before, and here I was, getting kissed by another man in public! We had a nice dinner and good conversation and I found myself surprised to enjoy his somewhat flirtatious tone and obvious interest in me. He was definitely acting like "the man" and pursuing me as if I was "the woman," which was something I'd never experienced before and found both exciting and a little strange. He was very masculine (and I wouldn't have even known he was gay outside of the circumstances), and he even picked up the check like a real gentleman! This really turned me on, because it felt like I was no longer trying to project the "strong confident straight man" I had spent my whole life striving to show the world. Jim acted like he knew who I was deep down (a bottom) and made clear that he was the one in charge.

I had come by an Uber and he had driven, and he offered to give me a ride back to my place. I offered for him to come in and join me for a drink, and he parked his car in my attached garage (my wife had taken our car with her when she left).

Jim had asked me at the restaurant about my separation and pending divorce, but now he started asking me some more personal questions. "What was the first fantasy you had about another man," he asked over a beer on the couch. He was sitting close to me and had put his arm around me and my heart was racing. Was I really doing this?

I asked if this would be private between us, and he promised it would and he really put me at ease, and I figured, why hold back at this point. He's here, I admitted online that I was a bottom, and I might as well be honest and open for a change.

I replied, "I always fantasized about being wrongfully sent to prison, and being cellmates with an older man. The man would notice how terrified I was at being small and vulnerable and clearly not knowing how to fight, and would tell me a very self-serving, but also somewhat comforting, narrative about how there are (and have always been throughout history) people playing male roles and female roles in every setting, even when there are no women around like in a prison, or in the Roman army, or on a Viking ship at sea. He would ask if I had ever thought about what it would be like to be a woman, and I would sheepishly admit the truth (yes), and he would then make his offer. For my time in prison, when there wasn't going to be any judgment from the rest of society, he would tell me it was my opportunity to be a "woman" for a few years and experience something I had wondered about before.

"In exchange for protecting me, he'd give me a girl's name, I'd be in charge of cleaning his cell and giving him massages, and would be expected to give him blowjobs and let him fuck me in the ass at any time. He would respect my wishes within reason and not be rough with me, but I would be expected to dress in anything he gave me (including women's clothes) and to always obey him, and he would treat me firmly but kindly, like I was his wife. In the fantasy, I would nervously accept his offer, and after a period of some hurt pride from the knowing looks of other prisoners at my lengthening hair and woman's skirt, getting used to the discomfort of a sizable cock in my mouth every morning, accepting the degrading sensation of swallowing his semen, and some discomfort at an erect penis plowing into my butt every night, I eventually would come to enjoy my role and even develop feelings for my "prison husband."

"Chris, that is an amazing fantasy, and thank you for being so honest in sharing it," Jim replied. "Would you consider being my woman, even if it was just in private?"

Now I was really excited and nervous at the same time, and I somewhat quietly responded, "yes."

"Would it be OK if I talked to you like I was your prison husband, firm but kind, and paternalistic about your status as a kind of "prison wife" here at your home? If it gets to be too much, just stop me," he asked with a twinkle in his eye, which told me he wasn't just doing it to fulfill my old fantasy, but for his own pleasure too.

"That sounds like it might be fun. OK."

At that, he came in for a real kiss on the lips. He pushed me back on the couch like I was the girl, and we started making out passionately. It was really strange making out with a man for the first time, and feeling his rough stubble on my smooth face, but also a massive turn-on. After a few minutes of kissing and grinding on each other, it was clear we were both very aroused. He unbuttoned my pants and I worked to unbutton his, and the next thing I knew, we were both naked.

We were kissing and I was rubbing my hands on his shoulders, bare chest, and stomach. I was used to women being "soft," and he was much "rougher" and firmer, and had a fair amount of body hair and a little paunch.

His penis was much longer and thicker than mine, and when he stood up from the couch and put it in front of my mouth, I was really nervous, but just decided to go for it and started licking the head. It was very soft (but hard underneath), and I started to take it into my mouth. I was licking the ridge of the head and could feel the soft texture of his foreskin on my tongue. I started trying to take more length into my mouth. I was actually sucking a dick now - no more fantasies. This was a real man's erection in my mouth.

"Good girl. Try not to use your teeth, and breathe out through your nose. That will make it easier on you and stop you from gagging on it," Jim said. Calling me a girl was a little humiliating, and also made my cock even harder.

I wrapped my hands around his hips and his butt (which was also a little furry) and he had his hands in my hair. I'd never had something this big in my mouth, and breathing through my nose like he told me was helping control my gag reflex.

After a few minutes, he started picking up speed and really fucking my mouth. His hairy scrotum was in a bit of a rhythm and hitting my chin. It felt warm when it touched my face. My jaw was starting to hurt a little from being open and the muscles being in this uncommon position for this long.

"You're doing great, Chris. Look me in the eyes while you suck. That's good. You're a natural at this. I think I might have to start calling you Kristen after this."

I was trying to move my head faster and his hands were speeding me up. As he withdrew a little before each thrust, I tried to move my tongue around his head and along the bottom of his cock as much as I could, thinking about what felt good when women had given me blowjobs. Trying my best to please this man.

I felt my tongue on the slit at the end of his dick, and I thought I tasted something different (his precum maybe), and then he took control of the pace. My eyes were starting to water when I heard his breathing quicken and some hot cum started shooting out into the back of my mouth. I started swallowing it and tried to "run through the finish line" by continuing to pump my mouth back and forth at a fast pace with as much tongue on his head and shaft as I could. After a few seconds he started slowing down and I was very thorough at "licking him clean" before he pulled out.

"Kristen, you're officially a great cocksucker," he said as he bent down and kissed me. I took a sip of my beer to wash down his semen.

I still had a raging erection, with a bright spot of precum of my own at the end, and Jim said, "Do you want to try something else that might help you with that," motioning to my penis.

"Sure," I replied, and he took my hand, pulled me off the couch, and led me upstairs towards the master bedroom.

"I like my girls clean before I fuck them. Do you have an enema here?" I had actually anticipated this, and bent over to pull it out of the cabinet under my sink.

"You are one prepared little Girl Scout, Kristen. Why don't you get down on the floor like the picture on the box and I'll help you out with this."

I got down on my knees and put one side of my face on the cold floor. It was a very vulnerable and open feeling as Jim got behind me and slipped the tip of the enema tube into my anus. The hard plastic hurt a little poking through initially, but felt OK as he penetrated it further into me. Then he gave the bottle a big squeeze and I felt the fluid filling up my insides.

I started to feel like I needed to shit, and he said, "The longer you stay down, the cleaner you'll be."

After some deep breaths, he patted my butt and told me to use the toilet. Once I was done, I walked back out to the bedroom and he was already in my bedside table, correctly predicting where some lube was.

"Did you already have this or did you buy it after your wife left?"

"I tried to talk her into trying anal once, but she wasn't really into it and I couldn't really get hard enough to penetrate her."

"Did you try to think of yourself getting fucked in the ass to get it up for her?"

"Yes," I responded surprised. "How did you know?"

"A lot of guys in the closet try to fantasize that they are the woman to get aroused enough to have sex with their wife, but it doesn't always work. Lie down on your back on the edge of the bed and hug your knees into your chest."

I did as I was told and could feel my rectum open up a little. I thought that this is how girls must feel spreading their legs for a man, and that Stephanie sometimes got in this same position, on this very same bed, and that now I was the girl, opening myself up to this man I'd just met tonight. I wondered what she would think if she could see this now.

He squeezed out some lube onto his right index finger and worked it around. Then he put his left hand on my right knee and started inserting his finger into my butt. It burned a little when he first pushed it in, but then started feeling kind of good.

"How does it feel?"

"It feels kind of nice."

"You are so submissive. I love it."

He continued to finger me and gradually worked up to three fingers in my butt, pumping gently in and out.

"Can you feel this," he said as he found my prostate and started pushing down on it as he pumped.

"Yes, it kind of hurts but feels good too."

"This is going to be how you cum from now on, Kristen. Stand up now."

I was wondering why he'd have me stand up, and then he sat back down on the bed where I had been and leaned back on his elbows with his legs off the bed. He had a nice new erection at this point. "Lube up my cock - you're going to want to put a lot on there to make it easier on you."

I squeezed a bunch into my right hand and then started slathering it onto his cock. It was hot and hard and I got it really greased up.

"For your first time, I want you to sit on my cock. Show me you want it by actively sitting on it and putting it in your ass. It will be an admission through physical action that you're gay and that this is your choice and desire to be buttfucked by an actual man."

I turned around and kind of awkwardly squatted. I grabbed the base of his penis kind of underneath and behind me and aimed it towards my butthole.

I started working the head into my butt, which was pretty greasy too.

"Push out like you're taking a shit. That will make it easier to get it in and more comfortable once I start fucking you in earnest."

I went ahead and did what I was told. It was really a turn-on to be ordered around by a man like this in a kind of dominant, matter-of-fact manner. A real man. I wasn't feeling much like a real man as his penis started sliding further into my ass, which I guess was the whole point.

I kind of felt like I needed to take a shit, and my ass felt like it was burning a little. My legs were shaking. It was kind of like doing wall-sits in a workout, except naked and with a man's erection slowly working its way into my anus. I was squatting a little bit up and down, wanting to sit all the way down to rest my legs, but the more I sat down the more full I felt with the discomfort of his cock sinking deeper into my ass. My breathing was a little uneven as I got used to this new sensation.

"You're doing great, Kristen. Just try to relax," Jim said as he caressed my hips, back and my sides. That made me feel even more feminine than I already did (if that was even possible with a cock buried in my butt).

Finally, I hit bottom and was resting on his lap with his cock all the way in. I could feel his black pubes on my butt cheeks. The exertion, and the discomfort of having a large penis in my butt, had deflated my erection, even though I was still incredibly turned on and my penis looked like it was leaking from being turned on for so long without any relief or direct stimulation from Jim. I guess this is what I had to accept as the "bottom" in our rapidly progressing relationship.

"You made it. Good girl. Now start working at it. I'm not going to be able to empty my balls into you without some more effort on your part."

It was kind of amazing that a month ago I had a wife and was totally straight to the outside world. Tonight, I'd been kissed by a man in public in front of a restaurant and taken him home. Jim had taken total control, and it had really taken off when I'd admitted my "prison wife" fantasy to him.

First kissing me, getting me naked and getting his cock sucked by me with no objection, then calling me Kristen, and now he'd spent the past 15 minutes getting my ass cleaned and lubed, and was now ordering me around about what it would take to "empty his balls" into my butt. Outside of a coach or a boss, I'd never let a man order me around like this, and certainly never in such an intimate, masculine, and somewhat demeaning manner. It was a little humiliating, and amazing at the same time. I suppose this is how a lot of women feel with a dominant man ordering them around and using them for sex. My role was to please this man and make him ejaculate now. I was clearly not "the man" here. Those days seemed like a rapidly receding memory at the moment.

I started trying to pump up and down on his cock and Jim started moving in rhythm to me. I could tell I wasn't moving as fast as he'd like, and after a minute or two he said, "OK, Kristen, I think you've proved to both of us that you wanted this. Let's change positions."

He kind of guided me onto the bed as he sat up a little and flipped me over (expertly keeping his hands on my hips and his cock still inserted into me so he never fell out). I was now flat on my stomach with my legs kind of off the bed and spread as he was standing behind me. "Put your hands on your butt cheeks and spread them apart as best you can."

I obediently did what I was told and he started fucking me faster. Once he was in a good rhythm, I let go of my butt cheeks. I was emitting an uncomfortable little grunt with every thrust and he was hitting my prostate. It felt like I was either going to pee on the bed, or orgasm, or both, although my dick was probably only like 10% hard and leaking cum at this point. Even my penis seemed defeated by this act of total submission to a bigger, stronger man and his bigger, more virile penis (which was quite hard and having no potency issues whatsoever, for better or worse in relation to my butt). The force of his thrusts, and his firm hands now grabbing ample handfuls of my butt, had me thinking that my butt cheeks might have some visible imprints by the time he had finished copulating with me.

He was now picking up the pace and getting close to the end. He moved a hand up to my left hip for a better grip as he rounded the bases for the finish.

After a few loud grunts, I felt some hot semen jet into my anus. He did a few more pumps to make sure he'd gotten it all out, and then slowly withdrew from me.

"Well, how does it feel to officially be a full-blooded homosexual catcher?"

"Kind of degrading and painful, but also strangely satisfying," I admitted as I gingerly pushed myself off the bed and started half-limping toward the bathroom.

He looked down at the bed and saw my cum in a little spot, and said, "It looks like you came, and your erection is gone, so I guess I took care of it for you as promised."

"I guess so, but I wasn't very hard and it wasn't like any orgasm I've have before."

"Yeah, it's almost like I fucked the cum out of you without a full orgasm. That happens to a lot of bottoms like you. You might have a full orgasm from time to time once you get acclimated to your role and your butt has an easier time of accepting my cock, but it won't be every time. Just like your wife's orgasms, probably few and far between."

I blushed a bit at this, and he noticed. "Did you ever give her an orgasm, Kristen?"

I was embarrassed and admitted, "I don't think so. I didn't last that long when I did make love to her."

"I understand. You were trying to be something that's simply not in your secretly feminine nature. It must have been really frustrating for you and her both."

"She kind of called me out on it at the end and told me I couldn't satisfy her because I was actually a fag."

"That's a harsh statement, but isn't there a little bit of comfort in accepting it's the truth? At least now that you're a catcher, you don't have to worry about getting it up or about how long you last. Your weak little penis isn't relevant anymore, since your role is to receive pleasure by pleasing a real man's cock."

I was really embarrassed (and turned on at the same time) by all of this. He was really treating me like I had fantasized a prison husband treating me. The fact that this man who was a stranger a few hours ago had completely diagnosed me and the problems in my marriage, and had used me for sex like a woman, and was now simply stating without qualification that I was gay. He was even speaking as if there was no going back, and I would be exclusively gay from now on. I had a sinking feeling he might be right, and that there would be no turning back to a normal life as a seemingly "confident straight man" after having experienced all of this.