Chain Gangbanged Ch. 01

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A lot can happen during a 30-day jail term.
2.6k words
4.22
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107

Part 1 of the 2 part series

Updated 10/23/2022
Created 04/16/2008
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sr71plt
sr71plt
3,025 Followers

I was only in for thirty days, and then not because of something I'd actually done. My buddy Phil had left drugs in my car, and the cops found them when they stopped me because I was driving a little too fast when I pulled away from a country beer hall they were staking out. I should have known better. I was only nineteen, and I shouldn't have been in that beer hall at all, let alone drinking. But I'd just finished my first year up north at Yale, and I was on the top of the world.

Thirty days in a county lockup had been my sentence. And not a lockup in a suburban county like the one I lived in but in a county back in the hills, where life is a lot rougher than where I came from.

I stopped going to the workout room, but the inaction was making me so jumpy that I volunteered to go out on work details. This proved to be a big mistake.

On my seventh day, my first work detail came up. We were going out to a rural spot to clear brush from the side of a road running through a heavily forested and hilly area. It was with great dismay that when I jumped up into the back of the van, I saw both Bobby Joe and Maurice among those who were going out on the detail.

It was a hot day and the work was hard. We had small saws and machetes and were clearing brush and saplings back some twenty minutes from the road. There were six inmates and three guards. Maurice clearly was in charge and everyone there, including the two other guards, were afraid of him. Everyone, of course, except Bobby Joe, who seemed to be a special friend of Maurice's.

Bobby Joe was probably the best and fastest worker among us. It wasn't long until he was so heated up that he stripped off his shirt and undershirt and was swinging away, covered with sweat that matted the thick, black hair on his chest and arms into swirls and made his undulating muscles gleam in the sunlight. The other inmates quickly followed suit in stripping down to their waists--all except for me.

"Take off that shirt," Maurice called out to me in a booming voice. "Can't you see it's too hot to work in?"

I pretended that I hadn't heard him.

"Take off the shirt, I said," Maurice boomed again.

"I'm okay the way I am," I answered in the most pleasant voice I could muster. "But thanks, anyway."

Maurice stomped over to me, and all of the inmates stopped to watch us.

"I said for you to take off that shirt, son, and I meant what I said."

"Sure thing, Sir," I said and I stripped my shirt and undershirt off. My eyes flicked over to Bobby Joe, and I could see a wide smile of appreciation on his face.

"And because you didn't do what I asked, you can go ahead and strip all your other clothes off too and work that way for a while."

I was dumbfounded. "But, Sir, this is a public road."

"Good point," Maurice said with a big smile. "You can go on into the woods there a bit and clear brush over by the picnic area. We'll see that no one goes in there, but not much of a chance they will. Not many want to picnic next to where a chain gang is working."

I started to argue, but I could see that this would just get me into more trouble, so I started to move off toward the picnic area.

"No. You can strip here," Maurice said. "The clothes will still be here when you get back."

So, I stripped all the way down to my work boots and could see that this gave both Maurice and Bobby Joe a little thrill. I was in very good shape and was better hung than the average.

"Okay, now go on over into the picnic area and start working," Maurice said. You can't go there alone, and if a guard goes, that will leave too few guards here, so . . . Bobby Joe, you come on over there with us. The rest of you go back to what you're doing here."

"Oh, God," I thought, as I stumbled off into the brush, trailed by Maurice and Bobby Joe. The very worst situation I could think of.

Maurice and Bobby Joe watched me work for a while, and the first thing I knew they both had their dongs out of their pants and were working them. Bobby Joe had one of those championship dicks in length and Maurice's was regular sized but was extra thick, and his balls hung low out of his fly.

I tried to make a break for it then and run back to the road, where maybe I could get some help from the other guards. But Bobby Joe lashed out with a hand and caught me as I ran past him and slammed me up against a tree. The blow caused me to sink to my knees, my back to the tree, and Bobby Joe was standing up against me, his pelvis pushed into my face.

"Suck me," Bobby Joe commanded in a husky voice.

"Maurice," I called out plaintively, begging for help.

"Maurice ain't going to help you none, pretty college boy. Open those lips and suck my dick. And don't do nothin' funny while you're about it."

He grabbed my hair with one hand and his dick with the other and forced his tool into my mouth. I gagged as he filled my mouth cavity.

"Ain't done this before, have you pretty boy? Well, you're going to get real good at it in days to come. Open wider and get your teeth out of the way and your tongue runnin' under my dick. There, that's good. Now let it slide in and out. There, yes, like that. Ahhh, such a sweet, soft mouth."

I felt tears coming to my eyes, and I was having trouble not gagging. His dick was getting bigger and harder as he slowly worked it back and forth in my mouth.

"Now, I'm going to pull out," Bobby Joe said, "and I want you to suck on the head like a lollipop and to work your tongue around it. Ahh, yes, I like that. You're going to be a good bitch."

His dick head was big and the pisshole was leaking precum. It tasted salty. The sweat of his groin was giving off a strong musky smell. These were entirely new sensations for me, and were not all that unpleasant. I admit that when I was being propositioned in high school, I let my imagination play with the possibilities, and I could feel my own tool coming to life under these new sensations. I also admit that being forced took much of the guilt away and was also turning me on.

"There, that's good," Bobby was saying after he'd pushed his dick back in and had pumped my mouth for a couple of more minutes. "Stand up."

I did so, and he pulled away from me a bit. I was trembling there, close to him. He held my head between his hands and came in for a kiss. I struggled with him, holding my lips together hard, straining to create a solid barrier to him, my arms went between us, and I tried to elbow him away from me. He brought his chest in hard against mine and lashed out with one of his hands, backhanding me hard across the mouth. Then he brutally kissed me again, this time working his tongue into my mouth and causing me to gag as his dick had already done. My jaw came unhinged and I just let him have his way.

The next thing I knew, Maurice was next to us and was digging my arms out and swinging them up and around the tree, where he used handcuffs swung over a branch above my head on the other side of the tree to suspend my arms over my head.

Bobby Joe continued his long kiss, as his hands flew over my naked torso and explored my balls and cock, which started to engorge at his touch.

"Whooie!" Bobby Joe exclaimed, as he broke away from my lips and started to wander down my body with his lips. "You're one fine bitch. Candy, candy. How sweet."

My lips now free, I started to yell, trying to get help from anywhere it might come. The ever-helpful Maurice whipped a dirty handkerchief and a roll of duct tape out of his pocket and had me quickly gagged.

All I could do was tear up in frustration and make muffled sounds of objection as Bobby Joe tongued and teethed my nipples and continued working his mouth down across my belly and taking possession of my dick, which responded to his attention, and my balls. In no time, he had his strong hands under my thighs and jackknifed my legs up and off the ground and swung my ass up to his waiting lips and tongue.

I was being penetrated and wetted with his tongue, which dug ever deeper, widening and lubricating my hole.

"Ah a really tight ass," Bobby Joe was saying as he dropped my legs and stood and turned toward Maurice. "We got ourselves a virgin, Maurice. Young meat. Yum, yum. Can I have him? Can I get firsties on a fuck?"

"Yeah, fine," Maurice answered. "But then you gotta do me, Bobby Joe. I'm dying here. And you gotta go easy with the kid. You've got a real club. The damage can't show when we get back."

So this was how it was between the two of them.

"Thanks, Maurice. You got a condom and some lube? He's gotta be open a lot more if I'm goin' get up in there."

Maurice, the walking supply closet, produced a small tube of lubricant and a condom in a packet.

"Now, let's get him turned around and hangin' on a lower branch," Bobby Joe said.

The two of them manhandled me while Maurice released the handcuffs and got me turned facing the tree. Then he handcuffed my arms again around the tree on a somewhat lower branch than before. Bobby Joe pulled my legs away from the tree by the hips and his lips went to my asshole again. Maurice slipped up between my legs and hunched in front of me, with his back to the base of the tree. He proceeded to take my cock in his mouth and give me head, while Bobby Joe was lubricating my ass, first with his tongue again and then with his fingers, heavily laced with lubricant.

I grunted in pain as he worked first one finger, and eventually three, into my ass, probing ever deeper and opening me up. The pad of a finger found my prostate, and, under the spell of circular rubbings on that, I ejaculated down Maurice's throat.

Then both Bobby Joe and Maurice rose and stood near me, where I could clearly watch, as Maurice opened the condom packet and rolled a condom onto Bobby Joe's huge tool. The two of them hugged and kissed deeply and worked each other's tools until both were fully hard again. Then Maurice stood in front of me, his eyes glued on mine, his hands wrapped around his dick, as Bobby Joe got behind me, pulled my hips back again, positioned his dick head at the entrance of my asshole, and slowly worked the head in.

I was screaming in pain and shock behind my gag, and my eyes were tearing up again. Bobby Joe pushed in a couple of more inches and then his hands went to my butt cheeks, encasing them and squeezing them and pulling them apart, giving him as bigger opening. I lifted my hips as best I could and arched my back, trying myself to widen the opening, knowing that all was lost now and no fight was possible.

At the same time, a little guilty thrill ran through me. All of that dick was going to be inside me. I was turning this dude on. I was being forced, raped, and none of this was my fault. I was both in control of being the object of his lust and being controlled by a hot stud. All of my "what if" fantasies were being brought to life, and no one could blame me for what was happening.

I gulped for breath, pulling as much air as I could through my nose. Maurice saw that I was in distress and said that he'd pull the gag out if I promised to be quiet. I nodded my head in assent, and he ripped the gag off. My mouth now free, I couldn't help but grunt and whimper at the four inches of dick pulsating inside me. Bobby Joe was going slow. When he sensed my canal opening to him, he pushed in another couple of inches. Six inches in now, and he went into a slow pump, two inches out and then back in two inches. After a couple of minutes of this, though, he came in another inch when he pushed back in; seven inches up my ass now. I yelped when he did this, and his hands went to my pecs.

He stroked my nipples, and I began to tremble and sigh for him, not wanting to do so, but my anger at being violated was being overcome with a new sense of pleasure mixed with the pain. He took his dick in one hand and revolved it in my ass. My ass walls responded by widening to him, and he pushed in another inch. I flinched, but I was managing him now.

"That's so nice," he whispered as he brought his mouth to the side of my neck and nuzzled me there. "Don't you feel it? Don't you feel yourself opening to me?"

"Yes," I whimpered softly. "But please, please stop." But I grunted in vain, as he went in another inch; nine inches now. But of course I didn't know how far he was in me. All I knew is that I felt totally stuffed and stretched, and my ass walls began to tremble under the strain. I also didn't know how long that was for any normal person to take until he whispered it to me. "God, I'm almost all the way in, son. Do you know there aren't many that can take this much of me even after a long time of trying? You're one sweet bitch."

I was panting and giving little yelps and grunts with the progress of the last inch he had to give. He had his chest pushed into my back now, and I could feel the wet hairs of his pelt on my shoulder blades. He was giving off a sweaty, musky scent that I found heady.

When I felt his curly pubic hairs tickling my butt cheeks, I knew he was in all the way and assumed that this torture was close to the end. But the ordeal had just begun. He started to stroke me deep then, pulling the head of his cock back to where it rubbed across my prostate and then, slowly at first, and then ever quicker, stroking back into me to the hilt.

No more gentleness now, and Bobby Joe himself was no longer in control. Instinct took over, and he went into a primordial fuck, no longer being sensitive to how new I was to this. But by now, my body had adjusted to him, and the pain was tolerable. At length, I felt him tense and the bulb of the condom fill up, and he just more or less collapsed against me.

sr71plt
sr71plt
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AnonymousAnonymousover 3 years ago

No jail on the United States would put someone sentenxed to 30 days on ANY work detail for ANY reason.

RobJasperRobJasperabout 5 years ago
Sexy story

Sexy story with great descriptions!

AnonymousAnonymousover 5 years ago

Liked it.Some guys just ask for a 'dicking'

AnonymousAnonymousover 8 years ago
A Journey to Being Gang Banged

You are very articulate, as I will also attempt in this response. I am responding here to provide some insight into gang-banging from my own life experience since it is on your mind.

My journey enjoying being gang-banged is very different and I am now much older than you. Between the ages of 20 and almost 30 I was in a 10 year relationship with a slightly older man who was in medical school when I met him. He taught me most of what I learned about gay sex. We lived together. HIs cock was very big in diameter at the base with a much smaller diameter at the tip. His total length was seven to eight inches. He would use my butt on most days, and often during both morning and night. He loved to be insertive and I came to trust him a lot. Since he was in medical school and became a doctor while we were together he understood a lot about anal sex safety with lots of lubricants and how to drive me wild with anal stimulation. I cared about him and learned to really like having him inside me daily. I often would long for him inside me even with our daily predicable sex. We used many positions and I was more than happy to accommodate new ways of taking him in me as he wished. If I would think about him during the day I'd often get an erection thinking about what we had done together and the smell of him sweating during sex. I'd become great at cleaning myself out often in the evening, knowing what was in store for me at bedtime. Going to sleep with his cum in me felt really good.

The spiked quality of his cock was great as he would penetrate me easily and then wedge me open for lots of pleasure. His cock also had a curve that made my prostate area sing when I was on my back. Our repeated activity took a toll on me after about four years. I developed a tear in the outer part of my anus. Since he was a doctor in residency at the time he was able to get me surgically fixed with an additional modification to my sphincter by a surgeon. This allowed me to have a larger opening yet still have plenty of muscle control. It improved our sex life a lot because i now had a greater range of muscle control and could take the thick size of the base of his cock more easily. After a few minutes inside me I had great control over making it tight or loose for him.

When the relationship ended in year ten, I longed to have this specific kind of regular sex. Being 30 and single was hard after knowing only this relationship for most of my adult life. I missed him in many sexual and emotional ways, and did not feel emotionally ready to be in another relationship but still had immense sexual needs. At times I would obsess about just having any man's cock inside me. I just wanted raw sex and was really afraid of emotional intimacy. My respect for HIV kept me in a constant state of frustration over health risks of being a passive partner in gay anal sex though I very often thought about being gang-banged.

The biggest initial problem with getting gang-banged was that I wanted only men I could choose to do it. The notion of letting anybody in a bathhouse use my body for their pleasure was not appealing. It was also really important for me to "see" who was pounding me so that we could have face to face contact during sex. I loved watching my partners' expressions when they had the ecstasy of ejaculating inside me. So I went for several years with a select group I created of between five to nine men that I enjoyed sexually. I had personally only found two of them. They then found others I came to like. Half of them were really young and they would often take two turns and were very verbal about what they wanted to try with me. I kept it playful. I would always try to take the young ones first because they generally would always came fast. The difference between this kind of sex and my daily relationship sex for the decade prior was profound. I was very accustomed to having simultaneous orgasms with my partner during our ten years together with pretty much once or twice a day sexual activity, as he would usually ejaculate inside me about exactly when I ejaculated. We never used condoms the entire time we were together over that decade. Conversely, in a gang-bang it is really important to use condoms though it is really not as much fun no matter what side of the latex you are on. Extra lubricant became really important, and making sure all my men had the condom on all the way down to the base of their cock shaft if they were going to put it all inside me. Anything over eight inches was off limits for me. It is not fun to have the ringed ridge of the bottom of a condom constantly rubbing on my sphincter. When everybody ejaculates inside a condom there is no lubricant inside you from the last guy who ejaculated in you like in porno movies, so lots of lubricant is essential to keeping it safe and fun for everybody. I know of many men who became HIV positive from being gang-banged without using condoms. Having all that cum inside your butt is cool to think about but never worth the risk.

More importantly, and simply put, was the mental transition for me with regard to neglecting one's own cock when servicing many men with my butt. I found during the first penetration it was often helpful to stimulate my own cock. But invariably as the shift of focus becomes my profound desire to feel many men inside me, I would eventually just go limp with my cock flopping as I was repeatedly pounded with me legs spread and held in the air. My legs were mostly held up and pulled back by the men who were either waiting for me or were done already. My completely anal focus on sex was a sensual longing that became addictive for me quite rapidly. Quite literally I did not care about my own orgasm when being gang-banged. After an evening with eight to twelve penetrations I felt overwhelming sexual satisfaction and yet would often never ejaculate myself. If needed I would just privately jerk off thinking about them afterwards when everybody had all left. The ongoing feeling left in my butt after so many men in me was really satisfying. I would do sphincter exercises often before and after the gang-bang events, and enjoy the sensation which I believe the French term which when translated means, "well fucked." That feeling could last for days. Was a sex addict?

I would also always had a small buffet for my men to eat along with wine and beer in real glasses and dishes (not plastic) using lots of healthy fresh food for them. I set it up with the sex on a heavy duty massage table in a spare bedroom where they could adjust my height above ground for their desired insertion effectiveness. It was a very heavy electric massage table that was perfect for gang-banging. I stayed away from slings as I tried one once and did not like the instability of it.

The group was almost entirely single gay men except for one who was married to a woman. He was truly the most sexually vigorous and most difficult to ejaculate quick of the group. He knew I wanted him toward the end of our gang-bang sessions and would often show up late. Sometimes I had to ask him to stop after ten minutes or so and would jerk off on top of me. Over several years the group evolved with some leaving and others invited to join in. Those added were by my invitation and were always referred by others in the group. I would always meet them privately before they joined the group. The usual time was early Sunday evening at my place. Rules were that I was the only one being a bottom and that everyone had to feel comfortable with ejaculating in me or on me at least once during the evening. I had it set up so that I could suck the cock of the person who was next in line before they entered me. Mentally it was really nice to get them more aroused with a little oral sucking before they got the condom on and lubed up. That also allowed me to get a good vision and feel of their cock that was going inside me next. I would ask them if they wanted a loose or tight butt, and "try" to give them what they wanted as best i could. It was my impression that some of them would also get together elsewhere at other times to explore each other with anal sex, but I would never ask. Most importantly I tried to make it all light and playful which worked to have many of them reliably come over on Sunday for the "GB event" as it came to be called. Having the GB event on the first and third Sunday of every month was perfect for most of these guys. Occasionally somebody would show up on the wrong Sunday evening. If I was home and in the mood I would accommodate them after cleaning myself out for them.

From a sexual standpoint I really began to wonder if one man could satisfy me ever again. In my twenties I thought I wanted a monogamous relationship and had one to which I was dedicated. If anyone had told me that I would be doing gang-bangs at my house in my early thirties I would have told them they were crazy. During the monogamous relationship that took up most of my twenties I was groomed as a receptive sex partner and became very proficient, especially with the surgical modification to my sphincter to enable me to make it looser and tighter with greater range when needed or requested. I can honestly say I had no real desire to ever insert my cock into anybody else.

Through it all, continence has never been an issue, but the "profound" longing to have sex by making myself a total bottom seemed to be just who I was destined to be in life. On several occasions the GB event had several men who just would not cum fast enough for me and it monopolized me in a way that made others a bit unhappy, including me. If they could not fix this problem they were asked to leave by consensus. They usually fixed the problem or just jerked of if i did not want to be pounded by them any longer.

The most profound thing I can say to anyone who is headed in the gang-banging direction for their sexuality is that you have to be safe. That means knowing something about your partners, and having their respect, in addition to giving them what you know you both want. In the long term I believe that this kind of bottom oriented gang-bang sex can be highly addictive especially if you are doing it with a group of men you generally trust and enjoy sexually. You get to know their bodies well and their expressions when they are in ecstasy in addition to something of their personalities. That becomes special but it is not the basis of any kind of relationship outside the GB event. Most of these men were committed to being single and did not really have much potential for a committed relationship in my opinion. They had a "catch it when it is around" view of sexual conquest. The GB event may have been nothing more than a reliable release for many of them, which was nicer than the bath house because it was more relaxed, more personal, and very predictable.

It became clear to me after being gang-banged by the group several times every month that it was also not a sustainable thing as I was aging into my thirties though I looked like I was in my twenties. I went to the gym and kept a 28" waist with my height of six feet and always looked a little buffed, but not hunky with any highly developed muscles. My aerobic exercise was mostly distance running. I was the all American boy, blue eyes, tall, skinny, and blond with short hair. a few Asian guys and one black guy (married) were a big part of these events. It became a joke that I would take the Asians first.

I also discovered that if there were more than eight of nine men doing me on an evening that I could sometimes just go numb in my butt. When this happened I would stop because it became almost impossible to feel connection with the cock inside me or the person driving it. Only once did I turn someone away without them doing a load inside me or on me. Fortunately he came back to the GB event and I let him have me twice during the next gang-bang event. He was really nice, gentle, and very sexy to me. He came to a lot of the events during his college years.

After several years a new man came to our Sunday gang-bang event that was referred in by someone who thought he might enjoy me on a regular basis. By then the GB event had boiled down to about five to six steady guys. I really did not want to do marathon events any longer. I knew my body well. This young man was clearly not experienced sexually and about 15 years younger than me, which was about the outer limit of age difference for me in the group. Oddly,we became friends and started to actually do "dates" which was a foreign concept to me. In his innocence I found someone that I really respected and cared about deeply across our generational gap.

Now I am well into my 60's and he and I are monogamous partners for almost three decades. Like a reformed addict, I know the highly addictive power of being gang-banged by a lot of men on a regular basis. It is not love, but rather a profound sexual itch that one can cultivate easily into an obsession that is not easily satisfied. If you go down that road it is very important to be safe and take care of yourself to protect yourself from sexually transmitted disease as you develop this aspect of your sexuality. It is hard to do sometimes but you have to do it. "You" should provide the latex condoms and lots of the lubricant you like the most, and take the extra effort to know the men with whom you share your body for your mutual pleasure. If they don't want to make the effort to do things your way or are not forthcoming about themselves for you to feel comfortable they are not generally a good option for having reliable safe insertion sex with you. I also never could handle smokers.

So... I have told you all this because you have recently discovered the joy of anal sex and I undoubtedly needed to write this because I never have spelled it all out before.

AnonymousAnonymousabout 10 years ago
Guiltless

I have tried gay sex a few times. (Strictly bottom) and work my hole most nights with a dildo. I would love to be in this situation. I related to your MC. To be forced to take a cock in your mouth or in your ass, removes the guilt and in turn heightens the pleasure.

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