From Chapter 11:
All of a sudden, it started to become clear to him: could Hugo really intend to use his asshole as a vagina? How could that battering ram ever gain access without tearing him apart; could it fit? If he did not want to be a cocksucker he sure as hell did not want to be a pussy or a cunt; but now he was a cocksucker, he enjoyed it... no he needed it and the cum it resulted in.
Chapter 12:
He said a confused good morning to Hugo, stopped by his locker, got the fleet enema bottles and went and took a shit. He had to strain a little and he looked at the stool to discover that it was about the same size as the shaft on Hugo's cock; but, how in the world would the crown fit in? Finishing up his morning's needs he met Hugo and Thomas going to breakfast. As he was leaving to take Thomas to the first class, Hugo said to him, "Plan on meeting me at the cubicle right after lunch."
After lunch, the younger boys had a rest period so that Hugo and Jeff were free. Hugo allowed Jeff to take his clothes off and strip down himself before he lay down on the recliner. He told Jeff to get on top of him, Jeff's head to Hugo's toe. In that position he could lie there while Jeff knelt on his knees which were placed on either side of Hugo's body. This position placed Jeff's face equal to Hugo's cock and balls and Jeff's ass about half way between Hugo's belly button and his face, allowing Jeff complete oral access to Hugo and Hugo a clear and unobstructed view of Jeff's crack and rose bud.
Hugo said, "Get started with your cock sucking practice. From now on I want you to set your watch for 30 to 45 minutes early every morning so that we can get up get dressed and come down here for a practice session. I want you sucking me off at least 3 times a day, morning, noon and night."
It was impossible for Jeff to respond as he was in the process of trying to get Hugo's cock into his throat. He stopped and reached over, got the lube and spread a large portion onto Hugo's cock, making it possible for him to try and get the cock into his throat. This was the first time that he had tried to swallow the cock rather than have Hugo insert it as he leaned back giving a straight shot.
He was having a tough time getting all of the cock into his throat. Hugo said "I want you to go to a site called HYPERLINK "http://www.sikihow.com/suppress-the-gag-reflex" www.sikihow.com/suppress-the-gag-reflex and read the info they have."
Although Jeff's response was garbled, Hugo could make out "what does it say?"
Hugo's replied, "You can read it later, but it says for you breathe through your nose, lift your legs into the air, put a little salt on your tongue and to hum. Maybe that is why guys joke around about getting a hum job. Try humming a little and see what happens. Oh, by the way when I get ready to cum I am going to pull out and I want you to let me cum on my belly for one or two shots and then put it back into your mouth for the rest of it. Do you understand?"
"Yes" answered Jeff, as he put Hugo's cock back in his mouth, swirling his tongue around the head and into the slit, and tried to figure out what song to hum.
Hugo slapped him on the ass and said "Hum dam nit; try Yankee Doodle Dandee."
Hugo took the lube from him, greased up a couple of fingers and got started with the stretching exercises on Jeff's asshole. Jeff tensed up so Hugo slapped him on the ass again and said "relax and let me have access".
Jeff closed his eyes and tried to think of something other than the very large cock being forced into his ass. On the one hand he had begun to enjoy having Hugo rubbing him, stretching him and what he was reluctantly beginning to realize was making love to his pussy. That thought so unnerved him that without thought he pushed his head down and swallowed, allowing Hugo's cockhead into his throat. He also started to hum which all but caused Hugo to lose his nut. With some effort Hugo got himself under control and continued his work.
As he played, rubbed and stretched Jeff's back passage, Hugo thought back to the research he had done on line concerning anal intercourse. According to sexinfo101.com he should start with his finger, and should rub and massage the area getting his partner (read this as slave) ready. He used lots of lube and had not gotten to the second step which was the insertion of his finger into the anal cavity. While he had put lube and his finger into the cavity he had not really done it other than to spread the opening and to help insert the lube. Hugo had taken to heart what the article said, "As with any form of intercourse, the anus must become use to the activity." He realized that he had enough influence and control over Jeff that he could do whatever it was that he wanted to do, but he wanted Jeff to want it also, which puzzled him. Jeff was nothing more than a slave, at his beck and call, so why did he care? Hugo began to realize that what he really wanted was not a slave but a partner who would accept his direction and control like a slave, but someone who he cared about and was his partner. He wanted a lover that he could control like a slave; a lover who so loved him that he was a slave to his love for Hugo.
From reading the articles, he knew that he had to take his time so that Jeff would not get tense; that he would not tighten up his muscles; and use enough lubricant. He was fascinated by the 5 major guidelines:
use enough lube; be prepared to stop if Jeff resisted; take it slow and with patience; disclose what you are doing; there has to be more than mere desire; there had to be a feeling of need.
Hugo realized that what he wanted to be able to accomplish was for him to be able to fuck Jeff in the ass; for him to be able to unload what felt like gallons of cum into his anus; to be able to get Jeff to get into the experience so that he would have an orgasm without touching or direct stimulation of his gentiles. He knew from his reading that feces were not stored in the rectum, which really was nothing more than a passageway, although some small amount of feces might be left after a bowel movement. That was the reason that he had instructed Jeff to use a fleet enema after each movement; it cleaned the passageway without going into the colon.
Following his research, he slowly inserted his index finger into Jeff's anus after a liberal application of lube into the passageway and in addition well lubing his finger. After about one half inch he felt the sidewalls in an effort to feel the two sphincter muscles, marveling in the fact that they were so close together. He was fascinated by the fact that the first muscle was controlled by Jeff through his central nervous system and that it could be tightened and relaxed like any muscle. He played with it, rubbing it and gently getting Jeff use to it being loosened and accepting of things being inserted. Just beyond it was the second muscle which is not controlled by central nervous system, but rather is an involuntary reaction meaning that it reacts to fear and anxiety. Here was the reason that butt fucking hurt. Yes, the first muscle could be hurt by breaching, but it was the second muscle that had lead to the clichés over the years about being so scared that you could not get a broom straw up my ass. He was also very happy that he had performed a Google search under "anal intercourse."
After a while, when Jeff had relaxed and was accepting of the finger rubbing inside his passageway Hugo decided to have some fun. While he continued to play with Jeff's backend, he decided to relax and enjoy the blowjob simply allowing himself to cum. Jeff was doing an incredible job and all too soon Hugo pulled his dick from Jeff's throat so as to allow the first two shots of ejaculation to accumulate on his stomach before reinserting his cock in Jeff's mouth for him to eat the last of the load and to clean up the head and slit. While Jeff was carrying out the cleanup routine, Hugo began to carry out his plan. He first took his index and middle fingers and got them covered in his sperm, and then he gently inserted these fingers into Jeff's rectum. Jeff could see him lubricate his fingers with the sperm and could feel them find his asshole. Jeff realized that Hugo had inserted his two sperm coated fingers into his pussy, and was overcome by a feeling of being subjected to, controlled by, and submission to Hugo. He now knew that in fact, he a guy, had a pussy. He felt Hugo's fingers slowly make their way into him feeling the sidewalls of his rectum as they made their slow progress.
All of a sudden, it was as if someone had reached up inside his dick and grabbed him. Jeff thought for a moment that the feeling hurt, but then he realized that it felt so good that it did in fact hurt; it simply felt too good. Hugo's fingers stopped their progress and slowly started to rub this area. Jeff had no idea what was going on but he realized that if Hugo kept it up that there was no way he could keep from cumming. He started to wiggle, squirm, moan and finally spit Hugo's cock out of his mouth.
"Please master, please" cried Jeff.
"What's the matter" responded Hugo, "Am I hurting you"?
"No it does not hurt, but you are going to make me cum!" gushed Jeff.
"You better not cum," warned Hugo, smiling because he knew that there was no way that Jeff could control what Hugo was doing to him and his body. Hugo wanted to make Jeff cum in spite of Jeff's efforts not to cum; he wanted to exercise control over Jeff and he wanted to Jeff, to enjoy himself but most especially he wanted Jeff to cum with no one and no thing touching Jeff's cock or nuts.
Hugo continued his massage of Jeff's prostate. He intended to make Jeff cum, but he wanted Jeff to cum so as to not mix the two boys' cum together because he intended to take the remnants of his ejaculation lying on his stomach and rub it into Jeff's upper lip, insert some into his nasal passages with a Q-Tip and to rub the rest on his hands so that while no one could see the remains Jeff would smell Hugo's essence every time he breathed in through his nose, licked his lips or brought his hands to his face. Then he was going to make Jeff lick up any leftovers and his own cum off of his stomach.
All of a sudden Jeff started to cry, his body shook, his eyes closed, he sobbed and came all over Hugo's cock and nuts. Some of it ran down between Hugo's legs into the crack of his ass. He had never felt anything like the orgasm that he had just experienced; but what was Hugo going to do to him for cumming without permission?