I Turned Myself Out Ch. 03

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..."

The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed.

"You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..."

In fact, I was naked, lying in the marital bed with my laptop, watching videos online and fucking myself with a huge, black dildo. (I had obtained a few sex toys by discreet mail order.) Needless to say, my kids were away at school and my wife was visiting with her sister in Buffalo, or I would be doing no such thing. I relaxed in the security of my privacy.

I had started following hypno sissy training when I became obsessed with the idea of sucking another man's cock. The trainers reinforced my desire, even multiplied it, until eventually I went out searching for dicks to suck. I had a few false starts. My first subject got cold feet and left me on my knees; the second, a trucker at a rest stop, turned me over before I could finish blowing him and fucked my ass. The experience was painful, quick and strangely satisfying, but such was my dedication in my quest to suck a cock to completion, I shoved it aside as a sideshow to the main event.

With my itch to perform oral sex on a man finally scratched, my mind more and more turned back to my experience with the trucker. I had survived anal sex; the only ill effects had been a bit of a tingling sensation that was shared parts pain and pleasure. I should add that I was lucky to have already accustomed myself to penetration using those same dildos or I'm sure I would have fared much worse.

Just as I had bolstered my courage and fed my oral obsession with hypno sissy cocksucking trainers, I now found myself exploring "anal slut training" videos.

"As soon as he enters the room, you drop to your knees. Your little dick twitches as he unzips to produce a tube of flesh much more impressive and masculine than your own. It is both long and thick. Your mouth is watering as he feeds you his cock. Its head slips past your lips and presses against your cheeks and tonsils as he proceeds to fuck your face. You have excited him; you can taste the pre-cum emissions that prove it. But there is a price to pay for teasing a man like this: he's going to take your ass and own it and you... you are going to let him."

I knew my cues from videos like these. With one dildo still deep in my ass, I began sucking and caressing another as if it was a real cock. The video showed men sucking dicks. The video clip compilation was unusually good for one of these videos; the cocksuckers all looked smaller and weaker than the men they were sucking.

My narrator continued.

"Lie on your back. You want to see what's coming. His face, his skin colour, his physique... none of that matters. You're only looking at his long, fat, drooling cock. It's why you came here; it's the reason you're paying for a sleazy, by-the-hour motel room. It's your job to give that cock pleasure, even if it causes you pain. It's your purpose."

The video had switched to a montage of close-ups on men's erect cocks. I continued to suck on my dildo until the video changed the theme.

"Here he is, the man who will initiate you into the mysteries of anal sex. This man is not like you. He is in complete control of both himself and the situation. As he approaches you, though you're afraid of being pierced by that potent tool swinging between his legs, your own smaller erection swells with arousal. The thought of being used for this man's pleasure teases you."

It was true. My arousal was self-evident. I was very into the scenario the video narrator described.

"You must remember that you exist in this moment only to be his receptacle. He's going to fill you like you've never been filled before and he's not going to ask you if it hurts or how you feel. You're just a sissy bitch; your feelings don't matter. Your top may even enjoy it if you weep or cry. He will use you and you will not resist; in fact, you will open yourself wide to receive him."

I spread my legs even wider. I was being strongly affected by the narrator's suggestions.

"That's right: raise your legs and spread your cheeks apart so that the cock of a superior man can stare down your puckered up, submissive little asshole."

I obeyed, spitting out the dildo in my mouth. All my concentration was focused on the sex toy in my arse.

"Take a deep breath and brace yourself for the pain. The agony of his penetration quickly passes and as the minutes wear on, your sobs subside into moans and sighs as your anal ring expands to absorb his invading flesh. He fucks your ass with the sense of purpose you always lacked when trying to take the initiative with women. Now you have found purpose as a fuck-toy for men. At first, you're disturbed because no true man would let himself be used in this manner, but you are quickly realizing that you are not a man at all; you're just a cock-serving sissy bitch. The thought makes your little dick twitch."

Jesus, this narrator was good. The dildo was deep inside me now. It was the largest object ever to penetrate my asshole and this was the first time I had ever got it in this far. The pain was real, but as I remembered from my previous experience, there was a real and growing pleasure as well.

"In and out, in and out, this superior man fucks you relentlessly, harder and harder. You let slip groans that are equal parts pain and pleasure and you know your ass will hurt tomorrow. You feel mastered by his strength and aggression; you feel weak and passive. You have submitted your ass to pleasure another. A part of you feels shame, but you are quickly coming to realize that this was what you were born for: to be a submissive cumslut for any man stronger than you... and they are all stronger than you. You are weak, meant only to be used. This is not a nightmare; it's your dream come true."

I fucked myself enthusiastically with the dildo, trying to match the incredible pace of the performer in the video.

"As he fucks you, you feel the slow burn of a building orgasm and you sigh as the last of your heterosexuality melts in its intensity. As his hips flex against your buttocks, you begin to meet his thrusts with your own feeble efforts."

My whole body pushed back against the rhythm I had established with the dildo I was poking up my ass.

"Do you know that from now on you will be eyeballing the crotches of every man you see, evaluating his potential to screw your brains out? You will need to be fucked silly and used often; not because you deserve it, but because all those men out there deserve to be satisfied."

I groaned, revelling in the humiliation prophesied in the video. I believed it was a true vision and the thought made the end of my penis wet.

"But the man using you now hasn't finished with you yet. He pulls out of you abruptly. You feel empty without his cock massaging your intestines. Then he grabs you by the arms, pulls you up and turns you over so you are face down in your pillows, with your ass up. He falls on you like a tree, and now his penetrating wood reaches an even deeper part of you. You are sure he has touched your soul as his thrusts build toward his climax. Again, you find yourself pushing back against his heaving body. When he groans and buries his dick deep inside you, you know he is coming. You feel the splash of his semen washing the inside of your bowels. It feels warm and comforting. You have served your purpose."

I emulated the bottom in the video, turning over with my ass raised and my face buried in the pillows, slowing the pace of my anal masturbation, but twisting the dildo around deep inside me.

"Your stud has collapsed on your back in an exhausted heap and you are flattened by his weight face-down into the bed beneath you. Is it the transcendent sensations of his twitching cock up your tailpipe or the sweet humiliation you have allowed to be inflicted upon yourself that triggers your own orgasm? For the first time in your life, a man has fucked the hot, sticky jizz out of you. You come for him, moaning and squirming like the little sissy bitch you are, with a cock still impaling your ass. You blow your pathetic little load all over the mattress beneath you without laying a finger on your little penis."

It took me a couple of more minutes—I paused the video—to achieve my orgasm as I pushed and pulled and turned the dildo in my ass. There was a strange burning in my hole and I enjoyed it fiercely. I thrust my cock against the mattress, maybe three or four times, before I felt the semen boiling in my balls. A moment later, I felt the sperm moving through me toward the head of my cock. I shuddered through a very powerful orgasm as my dick erupted spurt after spurt of hot cum. When I came in my bedsheets, as described in the video, I sighed and drifted off for a few minutes, laying in the puddle of ejaculate. When I poked my head up, I hit play on the video.

"The man puts his clothes on; what, did you expect him to cuddle with you, sissy? He hands his phone over for you to enter your contact information. He says that you will be ready to serve for him and his friends anytime they want, and you agree. That's the end of the conversation; after all, why would a real man want to talk to a passive cocksleeve like you? Other than giving you orders, what would a dominant male have to say to a submissive man-pussy like you? Even as you watch him go, you already feel an itch in your arse to take cock again. You know you will give your ass to any man willing to make it his."

In my post-orgasm stupor, I watched the video mindlessly, not realizing that the hypnotic voice was imprinting new commands in my mind.

"So, get off those dildos and get out there to give your ass away to strangers. Go to seedy bars and dark nightclubs, truck stops and public washrooms. You'll never be sorry and you'll never look back. If you need further encouragement, come back to this video for more training..."

After my orgasm, as usual, my determination to have my ass fucked retreated from active probability to vague possibility. I left the laptop on, playing the video on a loop as I drifted off to sleep...

In the morning, I woke to the video still playing and my cock stiff as iron. The overnight indoctrination session had made me incredibly horny, but not just for a quick tug; I wanted to be fucked in earnest. I felt an empty ache inside me; my ass was hungry.

"This will be the day," I said aloud.

As if in response, the narrator on the video said, "You know you will give your ass to any man willing to make it his..."

I wondered how to go about it. My quest for oral sex had been chequered with false starts; I wanted to get my ass filled on the first try.

"Go to seedy bars and dark nightclubs, truck stops and public washrooms..."

Nightclubs were out. I was a middle-aged man, too old for the likes of that twentyish crowd; besides, the younger generation listened to horrible music. Nightclubs and bars wouldn't open for hours yet anyway and I needed to get fucked as soon as possible. I lost my anal virginity in a brief encounter at the public washroom of the rest stop out on the highway, but on a Saturday morning, the place would be occupied by more travelling families than horny truckers. I finally sucked an old man's cock to completion in the public washroom in a shopping mall, but I was observed by a mall security/surveillance technician, who agreed to let the public indecency charge go... for a blowjob. I narrowly escaped being banned from the mall itself; it would be too risky to go there for sex again.

What about all the cocks I'd been sucking since I lost my oral virginity?

Both the old man and the security guy from the mall texted me from that day forward to arrange quick oral encounters, often in risky locations: underground parking garages, stairwells, elevators, cars. I had also become an on-call cocksucker for another three men: the plumber came to clean our pipes, and when I knelt before him, I returned the favour; a used car salesman who talked me down to my knees; and last, I have been blowing a co-worker in the closets and copying rooms of my workplace. These were all one-sided affairs; I pleasured the men without expectation of reciprocation, which was fine for blowjobs or sex; I expected, and believed I deserved, nothing in return. The only problem with these men was their attitude toward sex: they were each okay with receiving a blowjob from a sissy, but to actually fuck me would make them feel gay, and that wasn't how they perceived themselves.

So, I had to find someone new.

The criteria I set for my ass-fucking was simple. I needed a man who was bigger than me and willing to fuck me. I know I should have demanded that he was dirt and disease-free and that he would wear a rubber, but I was getting desperate. My lust for a cock in my ass had grown out of all proportion after my overnight loop.

I got up and immediately pulled the sheets off the bed to remind me to wash them before my wife returned tomorrow; it wouldn't do for her to find the starchy, semen stains in her bed linens after she'd been away a couple of days. I hopped into the shower and washed quickly, spending extra time on cleaning my asshole. Refreshed, I quickly dressed, threw the sheets into the wash and picked up my car keys.

A few minutes later, I was driving into the city and considering my options. I had heard that the park was a popular queer hangout, but the place would be full of families by this time on a Saturday morning, so it was not an ideal pick-up spot right now. The same was true for other public gathering places, like the library; too many women and kids and not enough single, horny men. The highway rest stop was starting to sound like an option after all.

Then I remembered my new gym membership.

My wife had signed me up at the local fitness club about a month before, and I had gone three of four times. It had occurred to me before that the gym was a potential treasure trove of cocks to suck; now I would check it out for men willing and able to fuck me. I am fond of saying I'm in decent shape for a man in early middle-age, but the truth is time is beginning to show on my waistline. So, I've visited the gym to run on the treadmill, ride the stationary bikes and lift a few weights. I had already lost a few pounds by this time, even though I wouldn't say I had a clear fitness plan in mind; I was really just checking out the ripped, sweaty men in their exertions... and the showers.

What did I have to lose? At worst, I'd go for a much-needed workout and take another refreshing shower. At best, I'd find a cock to tap my ass.

I had a gym bag in the car with workout clothes in it, placed there fresh after washing by my encouraging wife. Thinking what the hell, I took the drive out to where the gym was, out on the edge of town.

Once inside, I was pleased to see that the place was not busy. I found too many people distracting so this was a plus. I showed my membership card to the clerk at the counter and she waved me on.

"Not many people here today," I said.

"The majority of our clients come early in the morning, from five to seven, and in the afternoon from two to five weekdays. Saturday and Sunday are pretty slow usually."

Duly noted, I thought.

In the change room, there were a couple of guys just finishing up with their showers. I watched them, careful to look as if I wasn't. There was a skinny man in his early twenties with a thin dick cocooned in its wrinkled foreskin. The other man was heavy-set, fortyish and well-muscled, with a thick six-incher; he might be seven inches hard. He might have been perfect to cultivate as an ass-fucker, but I couldn't say anything with the younger man around. They were both changed and gone before an opportunity presented itself.

I finished changing and went out to the gym. I was still a stranger to that environment; I didn't know what I was doing with half the equipment out there. I worked away at various weight machines intended to strengthen all the muscles of the body, while looking around to find someone that might service be with their love muscle.

My eye fell on a pair of lean but ripped young men using the rowing machines and laughing together at some shared joke. I saw a couple of grandfathers with towels around their necks walking the treadmills, discussing local politics. There were perhaps a dozen other men of no special notice to me due to their age, too old or too young, or their physique, too petite or too fat. I wanted my first ass-fucker to be fit and forty to fifty years old but I was willing to think outside this box to some degree.

For example, my eyes locked on a late-thirtyish black athlete skipping rope near the change room doors. I estimated his height at taller than six feet, his weight at two-hundred pounds. His face and head were shaved and the sweat gleamed on his skin. He was wearing a t-shirt, but his chiseled body looked as fit as any I had ever seen. His enormous arms popped with muscles and veins. His legs might have been borrowed from some ancient statue of a Roman god. With his body in motion, it was hard to get a fix on his trouser snake, but I was definitely interested.

I was watching from the treadmill, where I was just putting in time jogging. By accident or design, the treadmills and the stationary bikes were perfectly placed to scrutinize the entire gym. I let my eyes linger on the handsome black man until he returned my gaze, our eyes meeting for just a moment. I broke off my stare. In my experience, superior men like to feel as if they can stare anyone down, so my eyes evaded his with the conscious intention to show deference. After a moment or two, I looked back at him again, only to find he was still staring at me. Again, I diverted my gaze, genuinely feeling the penetration of his glare. When next I dared to look back, he had put away his skipping rope and I watched as he walked through the change room doors.

I felt a clamp around my heart. This was my chance to approach him, but I was scared; of rejection, yes, but also of the good beating I might receive if my advances were ill-appreciated. My heartrate soared and my breathing was laboured; these effects were not from my exertions at the treadmill.

I powered down the treadmill and wiped it down, hoping that I was giving my great, black hope time to strip down for a shower. It had been about three minutes since he disappeared into the change room. I dared to follow.

I heard the shower running as I entered the tiled change room. I quickly stripped off my sweaty clothes and nervously joined him in the showers. There were no stalls; the showers were of the open variety, with three or four nozzles you could stand under, but with no barriers in between. I was able to view the man with ease and clarity.

His skin was a beautiful chocolate brown, and his torso was ripped and hairless. Between his legs, a curved cock swayed like a pendulum; even soft, it was probably nearly eight inches long.

He was perfect.

He was also staring back at me. I had not pressed the shower button that would set off a timed burst of steaming hot water; I had just been standing there gawking at him. Now, belatedly, I hit the button and a shock of cold water sluiced over me; the water quickly heated up, but not before I jumped in surprise.

The black man laughed at me and turned to face me directly as he soaped up his armpits. He plainly wasn't shy.

"So, are you another one?"

I couldn't believe I didn't have to start the conversation. For that, I was grateful, as despite my adventures in recent months reaching out to strangers to give them oral sex, my nature was toward shyness.