Groomed to Be Gay

Never in my wildest dreams did I ever expect Bill Withers to ask me what he asked me that Tuesday morning. We had worked in the same stockbroker's office for a couple of years and we were sort of friends. Often we'd have lunch together, and his girlfriend Debbie and my wife Linda went out shopping together sometimes. But that morning he had a concerned look on his face when he came to my office.

"Mike, you've heard about my troubles?" he asked rhetorically, for it would be hard to find anyone in the firm who didn't know he was being indicted for manipulating share prices. When I nodded, he sighed and continued: "My lawyer says it's almost certain I'll get sent to prison if I'm convicted. The courts are cracking down on white-collar crime these days. And you know what happens to good-looking guys in jail."

I thought at first he was going to tell me how scared he was, but to my surprise he went off on a tangent. "I can't stand the thought of not being at least partially in control. All my life I've taken pains to be as prepared as possible for every new challenge. That's why I need your help to prepare for this." I stared, not following him at all. "Mike, I need your help to learn how to have gay sex."

I flushed. Now it all started to fall into place. I had once told Linda about a homosexual relationship I'd had with my college room-mate. She must have told Debbie who told Bill. Now he was coming up with this way-out idea. I looked at him and said "I've never heard such a crazy idea in my entire life!" But he wasn't going to be dissuaded. He talked to me for nearly half an hour, and I reluctantly admitted he had a point. If he went into jail knowing nothing about homosexuality, he would learn the hard way.

At least if he practised with a friend who cared enough to initiate him gently, it wouldn't be a complete shock to him. I still thought it was a weird idea, but he was so insistent.

"So, when would be convenient?" he asked, as though scheduling a business meeting. We decided that Wednesday afternoons were the slowest part of the week for both of us, so he said he would see me at 2 o'clock on Wednesday.

After he left I sat at my desk for a few minutes, bemused, till my secretary buzzed to say my next appointment was waiting.

Two days later, I took extra care with my grooming and dress before I left for work on Wednesday. Linda glanced at me with an enigmatic expression as I left, but I wasn't game to ask her whether she knew about Bill's idea. At lunchtime I was so distracted I could hardly eat and my paperwork was mostly done on automatic-pilot. Finally it was 1:55 and I buzzed my secretary to say that I wouldn't be seeing any more clients for the rest of the afternoon and she could switch the phone to the answering service if she wanted to leave early. She accepted before I changed my mind. At 2 o'clock on the dot, Bill walked in and I locked the door.

"So, where do we start?" he asked cheerfully. I nervously suggested that the first thing for him to learn was how to go down on another man and he nodded thoughtfully. We retired to the couch and with more than a little shyness I undid my belt, dropped my pants and wriggled out of my shorts.

This was the awkward part. I had never thought about Bill in a sexual way -- heck, I had never been that interested in guys since I left college. What if I couldn't get an erection with him? I needn't have worried. Between the bite of the cool air on my naked genitalia and the latent bisexual side of my nature, I began to harden as soon as Bill moved closer to me. He carefully grasped my cock, letting it slowly fill with blood as he stroked it. Finally I was fully erect and Bill's hand was stroking me as he watched with characteristic concentration. "Next step?" he said at last, and I had difficulty keeping my voice calm as I gave him a few words of advice on how to begin.

His tongue flicked out and he began to lick the head and shaft of my cock. His lips closed around the top and he started sucking gently on the head of my dick. A little groan of excitement escaped my lips. He began to bob his head up and down awkwardly, trying to take more of my cock into his mouth, but plainly having difficulty fitting it in. He frowned, trying different ways of holding my dick. I arched my back, heaving my buttocks an inch off the couch as I pushed into his mouth. He gave a little grunt of surprise as I thrust into him, but I was really starting to get into this and I cradled his head between my hands as I began to move in and out of his mouth, fucking his face slowly and deliberately.

Bill soon got used to the rhythm, and after a couple of minutes I felt my balls beginning to tighten. I had warned Bill not to try too much the first time, and I groaned a warning that I was close to coming. He moved back a little and finished me off with a couple of strokes of his hand. I yelped and exploded in orgasm, showering Bill's hand and his forearm with hot globs of sperm. He was interested to see how far it traveled ­ he told me later he'd never seen another guy shooting off. While I got my breath back, Bill washed his hands and put his jacket back on, looking as though he had just come from a meeting of the Stock Exchange. "So, how was that?" he said.

"Not bad," I said with a satisfied sigh. "I haven't had another guy go down on me in years, but I think you show definite potential."

He nodded and said "Next Wednesday then?"

It soon became a regular part of the week. Every Wednesday afternoon, Bill would drop over and I would fuck him. I soon stopped making love with Linda on Tuesday nights, so I would be rested and ready for Bill. (I never had the courage to ask if she knew what I was doing in those afternoons). The third week, I came in his mouth and he was more than a little discomforted. Getting a mouthful of thick ropy sperm was quite different to having his face covered in Debbie's pussy juice. But typical of the man, he persisted and after another month he could suck and swallow with the best of them.

I jokingly told him that he could always make a living if he didn't mind competing with the $50 whores in the red-light district. "Am I better than Linda?" he shot back and I laughed that it would be disloyal of me as a husband to answer a question like that. But in fact Bill had become a good cocksucker, and I noticed I started to get a hard-on as soon as he walked in on Wednesdays (but not during the rest of the week, thank goodness!).

Even Bill was a bit wary of the next phase, despite his determined attitude. For homework, I got him a five-inch vibrator and told him to practice at home ­ with plenty of lubricant! ­ until he could insert it in his rectum. After a couple of weeks he said he'd managed it without too much trouble, but I could see that he wasn't looking forward to the next stage. The following Wednesday, it was Bill who took off his pants and lay on the couch. My dick was hard and red, and I had to keep reminding myself that I was doing this as a favor to a friend, not to satisfy myself. I smeared KY jelly over my dick and over Bill's backdoor, and gingerly positioned myself behind him.

"Now relax, and it will go OK" I told him and he nodded nervously. I pushed against his asshole, but even with all that lubricant it was reluctant to yield to me. I needed some way to relax Bill. Reaching underneath him, I took hold of his cock, which was half erect. Bill gasped ­ it was the first time I had ever touched him there. I started to slowly jerk him off, and he gave a little sigh of pleasure as he became aroused. Then, while he was enjoying my manual skills, I bore down on his back entrance again. This time the blunt nose of my dick managed to get through the anal sphincter and popped into his rectum. "Ahhh!" he groaned, as he felt me push into his bowels. "Relax," I whispered, "imagine it's just the vibrator."

I started pushing into him, slowly and gently, thrusting my rock-hard erection into his oh-so-tight hole. Bill was making little groaning noises as I began to fuck him in the ass seriously. I tried not to be too rough on him, but I was beginning to really enjoy myself - Linda isn't that fond of anal sex and I hadn't sodomised her tight little butt for a long time. It was just as well the room was soundproof, between Bill's muffled cries of pain, my moans of pleasure and the noise of the springs in the couch as we bounced up and down while I screwed my dick into his virgin asshole. Finally I grunted with sheer animal lust and groaned loudly as I came spectacularly into his bowels.

I lay on him, gasping for breath for a moment, unable to move after the incredible orgasm I'd just had. I slowly extracted my cock from the hole, wincing a little from the now-too-tight sensation. Bill lay there as though exhausted, and I noticed for the first time that there was a big pool of cum beneath him where I had masturbated him to climax while I screwed him. I would have to clean it down later. For a few minutes Bill said nothing, then he rolled over with a sigh and looked at me. "I'm sorry if I was too rough" I said, feeling a little guilty.

He shook his head wearily. "You didn't do anything that I didn't ask you to do," he said. "Maybe next Wednesday will go better." Again, I had to admire his determination. For a straight man to schedule being buggered in the asshole every week took a lot of courage.

He looked pale when he left, and I was worried for the rest of the day, hoping I hadn't hurt him. But when I saw him on routine business the next day he seemed quite himself again.

The following Wednesday, I laid him over the coffee table and fucked him doggie style. This time I laid a newspaper on the floor beneath him, so I could jerk him off without worrying about where the cum would spatter. He was marginally easier to get into this time, and I enjoyed myself just as much as the first time, finding it difficult to remember not to screw him as uninhibitedly as I would have liked. Again, Bill's ragged breathing and the way his hands whitened as he clutched the table revealed how difficult it was for him to get used to having his body invaded by my penetrating thrusts. (When I threw out the stained newspaper later, I was intrigued by the pattern that the dried sperm had created where he ejaculated ­ I mused that this could be a very enjoyable way to found a whole new school of modern art.)

I was surprised by how quickly I'd incorporated this strange ritual into my week. I had assumed that my relationship with my college roomie had been just a phase of my juvenile years, but now Bill had awakened the sleeping bi-sexual in me. I wondered if he was stimulated or repulsed by my obvious enjoyment of his body - it was hard for me to hide my excitement when I was hunching over him, sighing and gasping as I was driving myself into his tight little hole.

Originally this had started out as a way to save Bill from being raped by some tattooed biker with a twelve-inch cock, but I had rediscovered the joys of gay sex, glorying in the feel of another man's hairy flanks beneath me and his pulsing climax as I stroked him to orgasm. I still enjoyed pleasant unhurried sex with Linda in our martial bed but this was different. Plundering Bill's virgin backdoor was one of the highlights of my week, but I didn't know if he shared my enthusiasm. Perhaps for him it was like going to the dentist ­ necessary and relatively painless, but not something you'd do for pleasure.

Our first few fucks went something like this:

ME:"Ummmmm, oh yes! [sighing] Mmmmmm."

BILL:"Agh! [grunting] Uhhh! Uhhh!"

ME:"Yessss, oh yeah, ahhhhhh!" [crooning]

BILL:"Mmmph! [moaning] O my God! OOOOH - OOOOH..." [high pitched keening]

It was easy to see I was having a lot more fun than my partner was. But Bill was a model of dedication, believing that you could get used to anything if you tried hard enough, and after another month he was bending over readily every Wednesday for my hard dick. I'd trained him to go down on me first to get me hard, then to take it up the backdoor like a regular customer at a gay bath-house.

After another couple of weeks, Bill was as regular a participant in gay sex as you could find in the headquarters of Gay Pride. I wondered if this was changing his sex life with Debbie, or was it purely a business decision for him. Knowing Bill, I suspected the latter could be the case.

Then one morning this week I arrived at my office and my secretary said to me "Have you heard about Bill? They've dropped the case against him! The prosecution's chief witness skipped town and the judge threw the case out of court." I was glad to hear that Bill's freedom was no longer on the line, but after I sat down behind my desk I pondered where it left our little training programme. Exactly how much had Bill gotten into this whole relationship? Was it still just part of his plan to prepare for jail time or were we actually having an affair? I knew I didn't "love him" but were we involved or not? I wondered.

It's 1:52 p.m. on Wednesday afternoon now as I write this. I suppose in ten minutes I'll know the truth about that.