Transferred

Jay couldn't believe his fate. After graduating from high school, he took a year off and did what many guys in his situation do - he got bored, hung around with the wrong crowd, and then got in deep trouble. The justice system gave him a choice: pay a large fine and restitution, spend a year in the city jail, or submit to a year's stay in a reform school. Jay had quickly decided on the reform school option, since he had not earned a penny after getting out of school, and didn't want to spend a year around the unsavory types of people in the city jail.

In the reform school Jay became quite rebellious - in a nonviolent way. He frequently broke the house rules, and seemed impervious to the threat of serving additional time there. The school psychologist correctly recognized that Jay would like nothing better than to stay there for an extended period of time, and annoy the system - much the same flavor of rebellion that got him into the institution. The reform school then did what they did with all incorrigible inmates - they sent Jay to the girls' reformatory.

The most significant difference was that the girls' reform school dispensed ample corporal punishment. The girls' school also welcomed male "guests" for the humiliation aspect of their punishment.

As Jay rode in the transport van, he recalled his disbelief when he was told that he was being sent to the girls' reform school. He was speechless because, although he considered begging them not to do that, pride got the better of him. He had heard rumors about being sent to the girls' school and how the inmates' bottoms were kept sore from spankings, but had considered them unfounded. Now, with regret from his delight in pushing the system, he had no idea what lay ahead of him.

The two hours in the van had been uncomfortable, and the driver, a staff member from the reform school that he was leaving, did not want to talk. They stopped and passed through two guarded gates, and then arrived at the admissions center.

Two strong looking female staffers escorted Jay, whose hands were bound behind him, into the admissions bay. Beginning then, he experienced a series of surprises.

His eyes met those of the uniformed nurse inside the admissions bay. He immediately blushed. It was Catherine, a girl he'd had a wild crush on in high school. They had several of the same classes during the last two years of school. Catherine was blonde, slender, and pretty, with a sweet engaging smile. He recalled with embarrassment that during high school days she had frequently caught him staring at her legs. He had habitually fantasized lying next to her, both of them naked, handling and stroking her smooth bare legs while kissing her sweet lips and preparing to enter her. Jay had spent many moments in the paroxysms of ejaculation while thinking of the beautiful blonde Catherine.

And now, he was before her -- being admitted to a girls' reform school.

She smiled. Her smile was every bit as sweet as he remembered. His embarrassment deepened, as he saw the recognition in her eyes. She leafed through his file, and her smile faded. She pressed her lips together for a moment and continued reading his file. When she finished, she picked up the phone and pressed a few digits.

"Miss Allison, this is Nurse Catherine. We just got an M-ten in admissions. Health clean."

After a pause of several seconds, Catherine said, "Yes Ma'am," and hung up.

"The head governess would like to have a few words with you," she said to Jay. "After I give you an enema."

Jay's feeling of humiliation and shame deepened as he imagined the object of his high-school crush doing something so intimate in a clinical setting. The two guards escorted him to the nurse's station. Catherine walked ahead, and Jay's stomach fluttered when he saw the smooth slender legs that he had so often fantasized about.

In the nurse's station, one of the guards released Jay's wrist cuffs.

"I want you to strip, Jay," Catherine ordered, her voice taking on a crisp quality. "Everything off. I'm going to give you a three quart soapsuds enema, which you will retain for five minutes."

As Jay removed his clothing, Catherine continued, "I am required to note all instances of non-cooperation in your file." Then she snapped on a pair of disposable gloves and placed a firm bolster pillow in the center of the table.

"On your tummy now," she ordered, patting the examination table. Jay nervously climbed on the table and lay face down. The bolster pillow raised his hips, which added to his humiliation. She bound his ankles to the table with firm binding straps.

"Let your arms hang down the sides of the table," she instructed. When he complied, she fastened binding straps around his wrists.

"Okay now, we're ready to begin."

Catherine lubricated a gloved finger and inserted it past Jay's sphincter. She worked it all around inside him, and he wished that she would get it over with. She withdrew, put some more lubricant on, and applied it again.

He waited as she prepared the enema. He heard water running for a while, and then the sound of the full bag being clipped to a stainless steel stand.

He felt Catherine spread his nether cheeks, and for about twenty seconds, a soft object lightly touched his back entrance, moving around. Suddenly he felt a sharp pain as Catherine rapidly shoved the inflatable retention nozzle inside.

"AAAAAAH!" he yelled. The pain persisted for about a half minute. "Aaaaaah! Aaaaah!"

Catherine gave the attached bulb two squeezes and inflated the retention nozzle. It expanded inside jay's back portal, and he immediately felt extremely full.

"Ohhh! Uhhhhh!"

"I'm going to start the enema now. After it's inside you then you'll hold it for five minutes."

Catherine released the hose clamp, and the soapy solution began to flow. Jay felt a few jets of water shoot into his innards, and then the stream became steady. In almost no time the pressure became intense.

"Aaaaah! Ohhhhh! I'm FULL!"

The relentless enema persisted.

"Please! I can't...."

"Oh, yes you can," Catherine interrupted. "It's all going in before I start the retention timer." She decreased the flow rate slightly.

Jay continued to squirm, grimace, and complain as the enema expanded inside him. When the flow became blocked, Catherine gently rocked him from side to side, and then gave the bag a healthy squeeze. Jay shouted as the enema resumed.

"Aaaah! Oh! Ahh!"

He had never felt so full in his life. He forgot about his humiliation as the cramps gripped his innards. It took several minutes for Catherine to work the enema until the bag was drained.

"Five minutes now!" she said sweetly and looked at her watch.

Jay struggled and pleaded as his body desperately sought to expel the intrusion, but couldn't.

Catherine calmly stood by, and checked her watch every half minute or so. She was aroused by the scene before her. 'I'm enjoying this more than giving it to a girl,' she told herself. She also knew that she would greatly enjoy what was to come.

Near the end of the retention period, Catherine released the wrist and ankle binding straps. Then she deflated the retention cuff and pulled on the hose until it emerged.

"You can get up and expel," she announced. "Take your time - then we'll get you showered and present you to Miss Allison." She felt a twinge of arousal between her legs.

Her thoughts wandered as she sat and waited for Jay to completely get rid of the enema. About twenty minutes later she attached ankle cuffs connected by a short length of chain to Jay's ankles and led him to the shower stall.

"In you go, and get nice and clean all over," she ordered, and watched while he scrubbed himself and dried off. She cuffed his forearms together behind him and asked the staffer to escort him.

Jay's humiliation came to the fore and he asked, "Like this? Can't I get dressed?"

"Miss Allison wants to see you as you are now," Catherine replied, and turned around and led the way. As they walked through the long corridor, they encountered two instances of a new female inmate being led to admissions. Each time, the captive female stared probingly at Jay's nakedness, much to his embarrassment.

"I'll tell Miss Allison that I'm ready to present you, and then I'll be back to get you," Catherine told Jay, implying that he and his escorts had to wait in the hall. She unlocked a door and went in. A few uncomfortable minutes later, she emerged and asked the escorts to lead Jay in.

They traversed a receptionist's area and into an office with an open door. A name plate on the large desk said "ALLISON". The woman at the desk told the escorts they could leave Catherine and Jay with her, and to lock the door to the corridor.

Miss Allison, a dark haired woman in her mid thirties, was dressed in a white blouse and a grey skirt. The tone of her voice was crisply efficient, and her face seemed attractively sculptured.

"So this is a male from the other reform school. Listen, Jay, things are quite different here. That's why they sent you over here. Corporal punishment is freely given, and I daresay after looking at your file that you will likely have a constantly sore bottom until you learn some important lessons. It will go much better for you if you voluntarily comply with what you are asked to do."

Miss Allison waited a moment for effect, and continued.

"I will give you an introductory spanking now. Do everything you're told, or it will be worse."

She opened a desk drawer and pulled out a box of disposable gloves, a tube of lubricant, and a medium sized latex butt plug. When she had spread them on the desk she surprised Jay by unbuttoning her blouse and taking it off.

Jay could not resist staring at Miss Allison's breasts. He had never seen such perfect, seductive breasts.

"Jay, I want you to bend over across the desk while Nurse Catherine inserts this rectal plug."

Jay's heart was fluttering. His mind was confused, and he didn't know what to do. He was in a girls' reform school, naked and bound, and had just been told to bend over to accept a butt plug from his high school fantasy girl, by a woman who had just bared her attractive breasts.

"Catherine, perhaps he needs some assistance."

The blonde nurse gently pushed Jay up to the desk and guided him into a bent over position. Then she snapped on a disposable glove and put ample lubrication on a gloved finger. Jay flinched when Catherine inserted the lubricated finger between his nether cheeks, and worked it around rather brusquely. She withdrew, removed the glove, and retrieved the anal plug. After spreading some lubricant on the plug, she inserted it to the sound of Jay when he groaned, "Uhhhhhh".

Miss Allison then spoke. "I want you to stay bent over until I tell you otherwise. Keep your chest against the surface of the desk. I'm going to give you a caning now. You will receive ten strokes of the cane across your buttocks. Two extra every time you get out of position."

The bare-breasted governess retrieved a straight handled rattan cane and fiercely whisked it through the air several times, causing Jay to shudder. She stood to Jay's left side, extended her arm, and tapped the cane several times across his vulnerable uninitiated nether cheeks.

"I will deliver each stroke about five seconds apart. Catherine, please count them aloud," Miss Allison instructed.

There was a whippy noise followed by the unmistakable sound of the instrument making contact with bare skin. Miss Allison had placed a cane stroke directly across the center of Jay's buttocks, propelling the instrument so that the tip of the cane curled around slightly at the opposite end.

Jay immediately felt a sharp hot striation across his bottom. It seemed to intensify even after it had been delivered.

"AAAAAAAAUGH!" he screamed, and halfway stood up.

"One," Catherine's sweet feminine voice counted.

"Get back in position," Miss Allison ordered. That's two extra."

Jay bent down again. Miss Allison went through the ritual of tapping his buttocks several times before delivering the next stroke.

Whippppppp-SMACK!

"AAAAAAAAAAH!"

Jay kicked his legs.

"Two," Catherine announced.

"You may kick your legs as long as they both don't leave the floor at the same time. If both feet leave the floor, that counts as getting out of position."

Whipppppppp-SMACK!

"OHHHHHHHHH! AAAAAAAAAAAH!"

"Three," Catherine's voice quavered with excitement.

The next stroke landed immediately adjacent to the previous one. Jay furiously struggled to stay in position as he yelled. Catherine's voice was shaky when she counted out the fourth stroke.

Whippppppp-SMACK!

"AAAAAH! OHHHH! OWWWWWW! NO!"

"Five!"

Jay squirmed and kicked mightily through the sixth and seventh strokes. When the eighth stroke striped his bottom, he bolted upright again.

"That's four extra. Get back down there."

Miss Allison placed the ninth and tenth strokes near the upper part of Jay's buttocks. The stripes from the previous strokes were evidence that Miss Allison knew how to give a punishment caning.

"Catherine, please remove his rectal plug, and then I'll finish his caning."

"Yes Ma'am."

Jay flinched visibly as Catherine tugged on the plug and withdrew it.

"I'm going to administer your penalty strokes faster than I did the others," Miss Allison announced. "It will likely take considerable effort to stay in position, but the same rules apply -- two extra every time you get out of position. Consider this as motivation to take your strokes properly the first time."

Catherine stood rigidly, her legs pressed firmly together. Her eyes were wide.

The first stroke cut diagonally across Jay's bottom, intersecting several previous striations. Just as he started to shout, the second stroke landed. It cut across the other weals as well. His shout intensified, and he kicked one leg. The third and fourth strokes whipped across his buttocks and he kicked both legs.

"That's two more," Miss Allison ordered. "Get both feet on the floor, right now."

"Please, no more! Please!"

"You are not in a position to negotiate. Stay bent over with both feet on the floor for the next two, and we'll be done. Keep getting out of position, and you will be here for a long time."

Jay was breathing hard, and presented his striated bottom. He gave a loud shout with each stroke, and writhed. Catherine had seen many canings before, but this one was especially arousing to her. It was somewhat refreshing to hear a male voice under the striating cane, and to see a male's bottom and thighs twist and writhe. Although Jay was not the first male at the girls' reformatory that she had encountered, it was an infrequent situation and she was acquiring a taste for witnessing male humiliation.

"You may stand up now," Miss Allison stated. "Catherine, please unfasten his hands."

Jay, after his hands were released, turned around.

"Stay facing the desk, Jay. We're not finished yet," Miss Allison ordered, and stood up. Catherine was anxiously anticipating the next move. Miss Allison retrieved a strap-on harness with an attached probe, and laid it on the desk in front of Jay. Jay had never seen a strap-on dildo before, but its function was obvious. It had a mysterious sensuality to it, and he felt his stomach flutter. Catherine felt her panties dampen as her arousal increased.

Miss Allison picked up the strap-on, turned around so that only her back was visible, and removed her gray wool skirt and her panties, and placed them on the desk. She stepped into the harness and adjusted it so that it fit snugly around her hips, and turned around. She had a determined expression on her face. The sight of her standing there, legs spread, hands on her hips, lips pressed together, presented a frightful picture to Jay. He did not have to guess what was coming next. He didn't know, however, how intense his humiliation would be.

"Jay," she said, "I want you to bend over across the desk. Right now."

He didn't think he really had a choice, so he cautiously leaned over.

"Now reach back and spread your bottom cheeks. I want you to keep them spread until I tell you otherwise."

The striating pain from the caning gave way to embarrassment. He again thought of the sweet-looking Catherine, and how he was having to do these humiliating and private things in front of her. He placed his hands back and spread his nether cheeks somewhat apart.

Miss Allison nodded at Catherine. The nurse donned a disposable glove and generously squirted some thick lubricant on one finger.

"Open wider, Jay," the nurse's sweet voice instructed. He pulled a little harder. "More still. I want you to spread them completely open!"

With a flush of red returning to his face, Jay pulled his nether cheeks well apart. Catherine inserted her lubricated finger and probed around. Jay groaned when she pressed hard against his prostate a couple of times.

Catherine stepped back, and Miss Allison, with her ominous probe sticking out from her hips, walked around in back of Jay. She had kept her black high heeled pumps on.

"Very good, Catherine," she said. "Jay, I want you to keep your cheeks spread until I tell you otherwise."

She spread a thick coating of lubricant on her strap-on probe, and then brought it so that it just touched Jay's sphincter. With precision from obvious practice, Miss Allison pushed gently until the probe penetrated about an inch, and stayed there a moment. Then she steadily pushed until she was in as far as she could go. Jay gave a loud "Uhhhhhhhhh-Aaaaaaaaugh!" shout as she sank in.

She stayed like that for a moment for him to fully experience the feel of the probe when it was in all the way.

"You may release your hold on your buttocks now," she told him. "Reach across the desk and grasp the other end, and don't let go."

When he had done as she ordered, she slowly and deliberately pumped her hips several times, each time bringing the probe almost all the way out, and then pushing it completely in. Jay emitted a loud groan with each thrust.

After a moment of this Miss Allison withdrew and smeared more lubricant on her probe, and entered Jay, driving her probe to the hilt. He groaned again.

With a rather casual and careless flair, Miss Allison then subjected Jay to a prolonged and thorough fucking. She pumped with varying force, tempo, and penetration. As she fucked, Jay's reaction was an almost constant litany of choked utterances of surprise, humiliation, and discomfort. Catherine looked on with increasing arousal as Jay wriggled, twisted, and writhed under the continuous assault of the strap-on probe.

Miss Allison continued fucking far beyond the point where Jay complained of being sore from the interminable snaking in and out of the probe.

Catherine had seen Miss Allison previously use the strap-on dildo on a few recalcitrant female inmates - it was not something that was done as a matter of course. This is the first time she had seen it used on a male. Catherine believed that Miss Allison always knew what she was doing, and probably had a good reason for subjecting Jay to this grueling period of discipline and humiliation.

Miss Allison stopped her prolonged fucking of Jay's back way when she sensed that he really was getting too sore to continue. She slowly pulled out and told him to stand up. She bound his hands behind him, and told Catherine to summon the escorts to take him to his quarters. Then she got dressed.

As the staffers were leading the weary and humiliated Jay away, Miss Allison asked Catherine to stay.

"Next week, before his enema I'd like you to shave his legs and pubic area," Miss Allison stated. "Then bring him here. If you're ready, you can use him with the strap-on."

Catherine smiled and thanked Miss Allison.

She walked down to hall to her station and felt a damp tingling between her legs as she visualized pumping the strap-on probe into Jay until he begged for mercy.