Chapter 2 – Chapter 2

The next Monday Allen went to the mailbox at his house and discovered another misdelivered envelope destined for Sam Strang on Oak Street. With trembling hands, he turned the envelope over. In the bottom right corner, a notation had been written: "Indian brave" and, below that, "8 pm Wednesday."

Wednesday evening Allen was scheduled for a pickup basketball game at the gay men's sports club that he hoped Jack would go to. The role-playing fucks at Sam's house had him keyed up and his juices flowing. He felt sexy and more open to the possibilities with other men than before. He was interested in taking risks he hadn't taken before. There was a thug of a guy who had hit on him at the club but that Allen had been afraid to risk. He didn't come out for the pickup games on Wednesdays, though. He was there on Thursdays. Allen thought he'd give the guy a try—all because of how Sam had opened him up to possibilities.

Allen was interested in seeing Jack again too. He felt that Sam, in just those two sessions, had loosened him up, made him sexier. He wanted to know if Jack would notice that—and would give him more attention.

There was no question where Allen was going on Wednesday evening, though. Sam met him at the door in full war paint. He was wearing low-rise deer hide britches, with a laced-up codpiece, moccasins on his feet, a breast-plate bone chest shield, leather bands dripping in rawhide strings around his biceps, and a feather headdress.

Allen wore a loin cloth and moccasins. He didn't wear the loin cloth for long, though. With a movie of Indian gang banging a white old-West cavalry soldier blaring on the wall, and tent-like walls around three sides of an area with a floor-to-ceiling pole in it, the Indian chief lashed the young brave to the pole, wrists bound high over his head, lightly lashed his naked body with a many-pronged rawhide whip until both he and the young brave were hard as rocks, and then unlaced his codpiece to free his erection, held the brave's legs straight out from his sides in a splits, and fucked him from behind to completion.

For a second "go" at him, the Indian chief staked the brave who Allen was portraying out spread-eagled on a mound of dirt in his backyard, face down in the dirt; tickled him with feathers, saying they were providing the effect of the ants from the hill the brave had been staked on; and, eventually, mounted the brave's ass and rode him like he was a horse loping across the prairies.

Thursday, the misdelivered letter in Allen's box gave the fantasy as "Plantation owner's son; time for company," with the date of "Friday" and time of "8 pm."

So keyed up was Allen over the prospect of another role play that he went to the sports club's Thursday pickup basketball game. He found out that the thug who had been propositioning him was a policeman named Larry. In a remote corner of the locker room—on the same bench that Jack had originally fucked him, Allen let Larry handcuff him to a bench, his arms over his head and a gym bag under the small of his back to give Larry's cock a good penetration angle, while Larry slapped him around, squeezed his balls until he wanted to scream, and gave him a brutal missionary fuck.

Lost in the fantasy of a prisoner being taken in his cell by a cop, Allen luxuriated in every minute of the taking. Most surprising was that afterward Larry told Allen he had been a lot of fun and that what he'd like to do to Allen would really stretch his limits. When he went on to tell Allen what that would be in graphic terms and asked for his phone number, Allen gave him his actual cell number.

Before Sam, Allen would never have submitted to the handcuffed fuck, let alone shown willingness to do something darker.

* * * *

"You are the step-son of a plantation owner on the Mississippi who has, along with your mother, gone to New Orleans for a week," said Sam as he led Allen back into a bedroom with a four-poster bed, with canopy, grasping the back of Allen's neck with one hand and latching onto one of Allen's forearms with the other. Allen was wearing the colonial dandy costume he had bought at the store—frilly and blousy white cotton shirt, tight britches, and something similar to ballet slippers on his feet. Sam was wearing coarse woolen britches and a Henley pullover shirt in the same coarse material. Playing on the TV on the wall was a DVD of a group of black bulls gangbanging a young white guy on a river bank.

"I am the overseer of the plantation and I have lusted for you for some time. You are flirty. You know I want you. You know you want men. I know you are mine for the taking. Your step-father and mother are gone. Your step-father has been preparing you for him to deflower himself and you have become increasingly receptive to that. But he isn't here. I am here. It is time for you to lose your virginity. And you are going to lose it to me."

Suddenly, without warning, when they reached the bed, Sam backhanded Allen across the cheek and Allen spun around and fell back on the bed at the foot of the mattress.

"You've been a little tease," the overseer growled. "This is your time." Pulling the britches and undergarments off the legs of the son of the plantation, the overseer pulled his own shirt over his head and, grabbing the young man's ankles, bent and pushed his legs up into his chest and rolled his pelvis up. The young man was still trying to catch his breath as the overseer attacked his cock, balls, and hole with his mouth. In short order, though the son of the plantation gave in to the attentions in little mewing sounds and soft moans.

The overseer turned him over on his back at the foot of bed, hooked one of the young man's ankles on his shoulder, and held his torso flat on the bed with an arm across his neck. He worked the young man's ass with the other hand, penetrating him with an increasing number of fingers until he had worked in four up to the knuckles. While the son of the plantation writhed under him and begged for mercy that was not forthcoming, the invading hand pumped him slowly, with fingers rubbing the young man's prostate. The young man yelped and fired his load as the knuckles breached the sphincter, pulling in the thumb as well, and sank in to the wrist.

Moaning deeply, the young man went limp as the overseer fist fucked him for a couple of minutes more before withdrawing.

"You've taken a fist before, haven't you?" Sam asked in a voice displaying some awe.

"Yes, but not for some time," Allen answered, his memories going back to the desperation and high arousal of his time in Afghanistan—of the other men in his unit who preyed on men. Of how rough they could be. Yes, he had been fisted before. Never had he taken it with so much want and need and sense of being fully possessed as he was doing now, though.

The overseer fucked him in a reverse position, the young man facing down, his torso streaming down to the floor from the foot of the bed, his fists buried in the carpet at the end of the bed to keep himself steady. His calves were on the bed, held there with the overseer's hands clutching his ankles. The overseer's trousers were flared and sitting low on his hips. His cock was buried, reversed, in the young man's channel and he was pumping hard.

"Break away," Sam muttered, "and head for the door to the corridor." Allen did so, coming up short, because the doorway to the corridor was taken up with the figure of a massive black man, wearing only torn and loose cotton britches held up with a rope. As Allen stood there, transfixed for the moment, the black man leered and unbuttoned his fly, and a huge cock flopped out.

"You have two choices," Sam barked. "There's a door over there. If you run through there and get to the front door of the house and touch it, you're safe and the role play is over. This is Jamil. He's playing a slave on the plantation who has lusted after you as much as the overseer has. The overseer has said he can have you after the overseer has fucked your virginity out of you. If you want the black slave to have you, try escaping around the other side of the bed."

Allen scooted around to the other side of the bed without hesitation, where the black bull caught him, forced him down on all fours, shredded his shirt in pawing his chest, covered him, mounted him, entered him deep, and fucked him.

The black bull was bigger than anyone Allen had taken before, but he'd just taken a fist, so he could manage. The experience of being power fucked like this by a black man sent Allen up to heaven, as he grunted and groaned in the effort to remain open to the churning monster cock.

When the black bull came up to standing, he brought Allen with him, still deeply skewered on the black monster cock. Allen held close to the black man's bare chest, with his hands locked behind Jamil's neck. Jamil's hand were under Allen's thighs, keeping his legs bent, not reaching the floor, and spread.

Sam walked over close to them, his cock still erect and in his hand. "Have you ever been taken by two men at once?" he whispered as he came in very close to Allen, between the young man's spread legs. "I know you can take it if you agree to it."

"Yes, I've been doubled. Yes, I want it." Allen answered, licking his lips and his mind going back to the trenches and the lieutenant—but not only the lieutenant. A sergeant as well, in combination with the lieutenant—after opening him up with a fist. Just like now.

"If you decide you don't want it, we'll let you break loose and head for the front door," Sam said. Allen let loose of his hold on Jamil's neck, Sam's chest being close enough into him that he wouldn't fall, and he embraced Sam, bringing Sam into him.

"Both of you, now," he begged in a husky voice.

Allen pressed his head back into the hollow of Jamil's shoulder, raised his face, and howled to the ceiling as Sam worked his cock inside him on top of Jamil's and started to pump. Allen writhed in the throes of the pleasure-pain ecstasy of the exotic feel of having two hung men working him at the same time, his mind racing back to the trenches and of being shared by the lieutenant and sergeant, the two of them making him forget where he was, the danger he lived under, the horrors of Afghanistan. The fisting he'd endured earlier helped him take the two cocks—as did the emotional pleasure of knowing he was taking two, one of them a black bull.

* * * *

Saturday morning there were two envelopes in Allen's mailbox. He'd staked out his living room window and thus was able to see that it was the greasy, thin clerk from the costume store who snuck up and put the misdelivered mail in his box. One envelope, like the others, was addressed to Sam's Oak Street house. The notation on it was "rent-boy lap dance," with the time set for 8:00 p.m. that night. Allen looked on that with disappointment. That evening was a regular visitation session by Jack. He would be sorry to miss the lap dance fantasy.

Except that he didn't miss it. The other letter, addressed to him from Sam Strang on Oak Street, contained the note, "If Saturday is the time for a visit from your sometimes lover, cancel that. You must learn not to be taken for granted and he must learn not to take you for granted. This is training for him as well as you."

"What do you mean I can't come over?" Jack had said on the telephone. "This is our regular Saturday."

"I'm sorry. I have other plans. Maybe next Saturday."

"I may not be available next Saturday."

"Then it would be a pity for us to miss a fuck," Allen responded, saying good-bye and disconnecting before Jack had time to object further and after saying, "I'll call you to check on whether you want to come next Saturday."

Sam met him at the Oak Street house door at 8:00 p.m. He wasn't in any particular costume. When he shed his coat, Allen was wearing his red silk jock strap, the lace-up sandals from his Roman costume, and a red sequined vest that didn't meet across his chest.

"You said this was a learning experience for me—and should be for my lover too," Allen said to Sam at the entrance.

"Yes. I could tell from watching you in the store and from what you bought that you needed to move up levels from where you were in sexual activity," Sam answered. "Little did I know that you've been up many levels at one time—that you both were fisted and doubled before—and what you need is to recover them."

"What is there in this for you?" Allen asked.

"I get a luscious little piece to play with," Sam answered, "At least until you've regained all of the expertise you once had and the assurance that you deserve and can get better than you've been getting."

"And the lesson for today?" Allen asked. "A lap dance seems pretty tame compared with being doubled by you and that black bull."

"It isn't the intensity of it—it's the lesson that it's the sexual arousal and release that is the focus, not the partner you're with."

They entered the living room, and there, in a straight chair in the center of the room, sat the beanpole, gawky, greasy-haired clerk, just in gym shorts. He was hunched over slightly, his chest concave. From the tenting of the gym shorts and the grin on his ugly face with the pronounced Adam's apple, Allen could tell that he was ready and looking forward to the session.

"Dance for him, blow him, and ride his cock," Sam directed. "Your role is that you're a rent-boy in a sleazy club trying to get money out of any man who wants a lap dance—and more money for more service. Phil here has money. Your job is to make him part with his money. He'll reward you periodically as long as you are doing him well. Remember that the training is to be able to be a rent-boy—focus on the sex acts and the rewards to be won, not the client."

Allen crouched over Phil's lap and bumped and grinded for him to music and two TV screens of rent-boys giving ugly old men lap dance fucks. He got his first big bill by taking Phil's head in his hands and giving him a deep French kiss, more for rubbing his chest on Phil's and moaning during the dance. Even more for kneeling between Phil's spread legs, pulling the man's gym shorts off his legs, and sucking him off, taking the cream on his face, and cleaning that and Phil's cock off with his tongue.

Phil took over in the fuck. Sliding Allen's jock strap off as Allen rose from the blow job, tucking his arms under Allen's knees and flipping Allen backward. Phil's arms were strong and he was able to pull Allen's crotch up to his face and, while he was recovering his own hard, he sucked on Allen's cock and balls and ate out his ass. When he was recovered, he let Allen down to do a few more gyrations of a lap dance and then took charge again, positioning his cock bulb at Allen's rim.

"He's going to fuck you now," Sam said. "He's not the handsome hunk you usually need to open for. His cock is big, though. He's going to put it in you."

"Yes, yes, fuck me," Allen whined, taking Phil's head between his hands and kissing him on the lips. "Give it to me hard, big boy."

Phil held Allen's body at the waist and slammed it down on the cock. Lift up and slam down. Repeating it for as long as it took for him to bottom. Yelping and writhing, Allen settled down, collapsing like a rag doll and completely docile before Phil started the serious pumping, letting Allen's body arch back to the floor, while Phil gripped his hips and pulled him on and off the cock in swift, powerful, deep strokes.

"Yes, yes, give it to me. Fuck me hard!"

Phil held off on ejaculation for almost forever—some time after Allen had shot off again—before he filled the bulb of his condom, leaving Allen in a sighing, purring heap at his feet.

At the door on the way out, Sam said, "Remember that. Their looks don't always match their sexual prowess. Phil could make you his willing sex slave if I let him—and I can see in your eyes that you recognize that. So, when you are in your rent-boy role, don't judge a client by his looks or even his diffidence. I'll bet this lover who doesn't fully satisfy you is an Adonis."

"Yes, he is," Allen admitted.

"To be satisfied by him, you will need more than a pretty face and a big cock from him. He'll have to want to fuck you so bad that he'd give you the attention you need. And remember for your own pleasure, Allen, that it isn't how handsome the man is or whether he is, it is that he has his cock inside you and that he knows what to do with it when it's in there. Keep your mind on the fuck."

* * * *

The follow-up instruction on misdelivered mail on what he was to do on Tuesday evening was more in this vein. "The Smallwood Rest Stop. Do two ugly truckers."

The first one was a pudgy man old enough for the fringe of hair on his head to be turning gray. Allen had bellied up to a urinal at the notorious rest stop on the highway to which he had been directed. He waited until an obviously interested trucker came in and moved into the urinal next to him. They held there longer than necessary for a guy to take a piss and long enough for them to signal each other with their eyes.

The older man turned toward Allen enough for Allen to see that he was in erection. Allen turned as well, and the man reached out and touched his cock, which helped it go harder. Allen had managed to harden up by running the image of ugly Phil and what he could do with his cock through his mind repeatedly. With effort, he found that the experience itself, this setting, was enough to arouse him. Allen reached over and more aggressively took the man's cock in hand.

"Can I suck you off?" the man asked in a tentative voice.

"I'd rather you fucked me," Allen answered. "Do you want to do that?" The man nearly lost his teeth in that offer.

"The stall over there," Allen said.

The man sat on the toilet, his pants down around his calves, and, sans shorts and briefs, Allen sat in his lap, facing him, and bounced up and down on the man's cock until the trucker came. The trucker had a very nice cock, Allen found, and he had a technique of kissing every inch of Allen's internal walls with its bulb.

Afterward Allen offered his ass to a tall, thin guy in flannel shirt, jeans, and cowboy boots leaning up against the side wall of the toilet building in the shadows and smoking a cigarette. They were around at the back of the building, between a huge air handling system and the back wall of the toilets before Allen realized that it was Phil, sent by Sam to check on whether Allen had carried forth with the assignment.

Allen raised his arms over his head, pressed his chest against the back wall of the toilets, and jutted his naked buttocks back into Phil's hands. Phil went down on his knees behind Allen, spread Allen's cheeks with his hands and attacked Allen's asshole with his mouth. He snaked a hand between Allen's spread thighs, milked Allen's cock, and fondled, squeezed, and distended Allen's balls until Allen gave him his cum. Then Phil mounted Allen's ass, gripped his hips, and fucked him hard for twenty minutes before coming himself, leaving Allen a puddle of putty in Phil's hands. They went back to the car Phil and driven, got in the backseat, and made out like teenagers after the prom, with Allen winding up on his back across the seat and the toes of one foot wedged into a side hook above a door and the other hooked on the top of the front seat, while Phil lay on top of him between his spread legs. They worked each other's mouths while Phil was pounding Allen's ass again.

Ugly is as ugly does, Allen was taught—and Phil did anything but ugly. Allen had to assume he'd gotten passing marks for his rest stop lesson.