Return to "Weekend School" Ch. 14

[This story involves bodily functions and sometimes severe disciplining, including caning and spanking, as well as crossdressing. If reading about those offends you, read no further. These stories may be read separately but do gain from being read in sequence.]

Laura Franklin wasn't sure what kind of response she would receive when she sent out notices by mail and e-mail for the next Weekend School she ran. Laura was all of 25 but quite mature for her age. She had started this school for middle-aged men and women to attend. There were two classroom teachers, two prefects, and a few other staff members.

The school experience featured corporal punishment imposed by the teachers and the prefects. The weekend students learned quickly that punishment was ordered immediately upon the commission of any offense, no matter how slight.

This weekend program was designed differently. Laura knew that many middle-aged men warmed to the idea of going back to school and being treated as females. So, she said in the notice that this weekend was for "girls and special girls." Special girls, it was readily understood, were men who were required to dress as schoolgirls, just as the women would dress.

The notice contained information on where to obtain the required schoolgirl uniforms. Instructions described how to measure for various items. Both men and women needed to obtain white blouses, short maroon skirts, white socks, brown oxford shoes, white cotton panties, plain white bras for women, and white training bras for the special girls. Upon arrival, the school provided hair ribbons in the school colors.

Melanie Andrews received the notice and mentioned it to her husband Frank. Both were in their mid-40s and their children were away at college. Melanie had previously attended a session and enjoyed being treated like a naughty schoolgirl and embarrassed appropriately by having her panties lowered for inspections and spankings.

She persuaded Frank that this would be a nice escape from their standard weekends at home. She knew that Frank did have a craving to wear panties, usually her panties when he was home alone. She had caught him wearing them and now ordered him to put panties on when she felt he needed to be disciplined.

"You'll be a special girl, Frankie," she grinned as she described the school to him. "It's a whole femmy world there. All the teachers and everyone are female. And you'll be dressed like me, as a schoolgirl."

Frank realized he would be terribly embarrassed but also found that just the prospect of going to this weekend school dressed as a "special girl" had given him an erection. Melanie noticed the tent in his trousers and smiled, "Frankie, I see that Little Frankie is already excited by this getaway."

His face colored in shame at being found out so easily by his wife. He did enjoy her taking charge of him, however. Melanie now found reasons to spank him on his bare bottom every few days and he had to admit that sex had never been better for both of them.

They drove to the school in the country on Friday at midday. They were greeted by Allison Kirby, a pleasant young woman who served as dorm resident. She explained that there were dorms for girls and for special girls. She would monitor both of them.

Looking at Frank, she asked him if he would need help in getting dressed in his school uniform.

"No, Miss," he answered, "because my wife has worked on this with me already."

Allison smiled and said she was sure he would enjoy his time at school this weekend. Frank looked Allison over, in her black skirt, white blouse, seamed black hose, and three-inch heels.

"Are you staring at me, Frankie?" she suddenly interrupted his reverie as he had been undressing her in his mind.

"No, Miss," he responded, "I was admiring your charming figure."

"That is not what we expect here from special girls, Frankie," she snapped. "Stand up and drop your trousers."

Frank was surprised at how quickly he had already gotten himself into trouble with this dominating young woman, who looked as if she were 30 but in reality, had just celebrated her 23rd birthday.

When he had complied with her order, she stood behind him as Melanie watched and pulled down his boxer shorts.

"You won't be wearing these clothes for much longer, Frankie," Allison declared, "so next time your panties will be taken down when you earn punishment."

She reached into her handbag and took out a small black graphite rod. Frank was ordered to bend over and grasp his ankles.

Allison held the rod, lay it across Frank's bare bottom, drew it back, and began snapping it across his bottom in a measured stroke, aiming and striking at all parts of his pale bottom cheeks. Sometimes the rod hit low, almost on his thighs and he was worried that she might actually hit his sensitive parts between his legs, such as the base of his scrotum.

Allison stopped the punishment after a flurry of strokes had overcome Frank's resistance and had him crying in pain. She threateningly poked the tip of the rod softly between his legs and touched his scrotal sac and then his now-erect penis, frightening him as she had intended.

"You better behave, Frankie," Allison remarked offhandedly, "or you might be feeling my little rod where it just touched you."

"Now, for both of you," she ordered, "Melanie, go into your dorms and get into your uniform. We will assemble for vespers at 6:00 P.M. sharp."

"Frankie, you will come with me to be measured and outfitted," Allison said sharply.

As she left, Melanie whispered to Frank that he needed to be very careful if he didn't want to get caned the first night.

Allison escorted Frank into the special girls' dorm where Miss Carmody and a prefect, Diana Prentice, were sitting behind a table. Also present were three other men. They were introduced as Sally, Annie, and Carol.

"This is Frankie," Allison announced to the group.

"He's already been naughty—staring at me," she reported.

Both Deirdre Carmody and Diana expressed their disapproval of this behavior.

"Young man," Deirdre said, "you had better learn to mind your manners if you don't want to be punished until you do."

"Now we will measure each of you for your uniforms," Diana, a gorgeous blonde, said. Looking at Frank, she ordered him to stand. "You'll be the first one," she declared.

He was ordered to strip, and he did so, placing his clothes on the chair where he had been sitting.

Diana looked him over, told him he had better figure out how to lose his erection, and brought over what she had decided was a pair of panties of the size she estimated would fit him.

Handing them to him, she snapped, "Put those on right now."

He pulled the white shiny panties up and was surprised at how comfy they felt.

"Now take them off," the prefect ordered.

He slipped them down and off and she handed him what looked to be a G-string, but with a plastic shield under the cloth triangle in front,

She told him to put this on and she helped him pull it up, gently pressing on his penis so that it pointed down and was covered by the plastic shield.

"That will give you a nice femmy look in front," she commented with a smile as Frank realized that his cock was now trapped pointing down beneath this shield, which Deirdre referred to as a "modesty panel."

Then Diana took a tape measure and ran it around his chest over his tiny nipples. She went to a rack in the back and returned with a white training bra that she helped Frank put on. She placed inserts into the flat cups so that now when it was hooked, Frank had apparently acquired two modestly sized breasts.

Then came the school white blouse and the short plaid skirt. Next, Diana handed him a pair of thin white socks and had him try on some childish-looking brown oxford shoes.

Finally, Deirdre had selected a brunette wig that when placed on Frank's hair, complemented his face with bangs and a flip.

Diana had hit sit facing a mirror and she applied some makeup to his cheeks—just a bit of blusher and some mascara dabbed on his eyelids. A slight coating of lip gloss followed, as she felt lipstick would overdo the effect.

The other men sat totally nonplussed by observing what had been done to transform Frank and now awaited their own reorientations.

When Melanie and Frank (now Frankie) arrived at the assembly at just before 6, they found a room full of women and men dressed in schoolgirl uniforms. Frank was surprised at how well the uniform fit him, although he did feel confined by the shield in the now tight little panties he had been provided with.

He sat next to two of the other "special girls" he had met in the dorm, Sally and Carol. They were dressed identically to him.

He recognized the older woman dressed in the standard teachers' outfit—which was a tweed skirt, colorful blouse, sheer hose, and pumps—who stood at the front and called the group to order.

"I'm Miss Carmody, and I serve as matron and dean of studies," she announced. "This weekend, I've been asked by Miss Franklin to fill in as well as a teacher, so some of you, eventually all, will be learning from me in the classroom."

"You all look quite nice," she smiled "and especially you special girls," she grinned.

"Now I'm going to ask Miss Kirby here"—she pointed to Allison—"who will escort the women, that is, girls, to their separate meeting. You special girls will stay here with me."

At a signal from Allison, the women stood and walked out of the room, leaving the dozen "special girls" with Miss Carmody.

"I need to go over the rules with you, because it is likely a new experience for most of you," she began. "You will find in your dorm that we have stall toilets. This means that you will sit to do your business—including peeing. Anyone found standing to pee will be disciplined. You don't know much about our disciplining, but I suggest you regard it seriously, as we mean it to be seen."

"You have all shaved off any facial hair," she went on, "which is excellent. Tonight, I want you to use an electric razor or a regular one to remove as much of your body hair as possible. This means under your armpits, your chest, and your legs. But leave your pubic hair alone, above your male organ. We like our special girls to have proper bushes."

"The training bras have been designed to fit you and to make you look more femmy, some inserts for the cups give you a fuller bust," she explained.

"The teachers, prefects, and dorm residents will be inspecting your panties quite frequently, because we know that special girls don't always adhere to immaculate hygiene in your underquarters," she observed.

"Again, please take this seriously because we do, and any stains will result in punishment being awarded," she declared. "So even if this is new to you, wipe the tip of your penis after you pee and be very thorough in wiping your bottom after you make a doody." She smiled at the perplexed looks that greeted her use of the childish term for defecation.

"I do hope you all are enjoying the chance to be special girls," she exuded. "We will be trying to provide you with a special feminine experience while you are here. Diana put a bit of makeup on each of you but Allison, who is now with the ladies, will come by to show you how we expect you to learn to apply makeup."

"The teachers expect you to comply immediately if they tell you you must prepare for punishment," she added. "You will come up to the front, lift your uniform skirt and make sure it stays up by tucking it into your waistband and then pulling your panties down just below your bottom, bending over, and making sure your legs are spread well apart."

One man whispered to the man next to him.

"What were you saying, Alfrieda?" Miss Carmody said sternly. "You will tell the group right now!"

The man wearing a flaming red-haired wig looked embarrassed and said, "I told him that spreading my legs like that and bending over was something I'd never done."

"Well," Miss Carmody said, "come up here and we'll give you a chance to demonstrate it to the group."

He walked up to the front and she motioned to him to do what she had just instructed them, so he did lift his skirt, tuck it through the waist to hold it up, pulled his little panties down below his bottom and bent over, with his legs apart.

The group could now see his open anal crack, his recessed dark anal opening, and the hair around it.

"Tonight, Alfrieda," Miss Carmody told him, "Allison will make sure you are shaved around your bottom-hole. Stay bent over and clasp your ankles now and hold on. No moving."

She picked up a small thin cane from the desk and held it in the air, which quieted the room even more. Then she stood behind the man who was bent over, lay it on his bottom, drew it back, and fired a searing stroke on the middle of his bottom."

Alfrieda (Alfred, of course) screamed but did not move, despite the horrible stinging pain he was feeling.

"I think that should give you an idea of what punishment means," Miss Carmody explained as she told him he could pull up his panties, let his skirt down, and return to his seat. "Your teachers, however, including me, will not stop at one stroke."

Everyone was quite worried now, but Miss Carmody told them they would now go to the dining hall and could relax and enjoy themselves.

"You will all be going to bed in the dorm soon afterward," she advised, "so enjoy yourself with your partner at dinner. You will not be seeing them after this meal until tomorrow."

Allison, meanwhile, had had the women stand, lift their skirts, lower their panties, and bend over with spread legs. She passed behind the, stopping to peer into every anal crack. She told a few of the women that they needed to clean their bottom-hole area more thoroughly. She could not see their looks of shame at being singled out for such intimate criticism of their hygiene. She did not apply her cane to any of them, though.

"Now you will join the special girls in the dining hall," she announced. "Do not think that you may go to their dorm or have them with you in yours. It is strictly forbidden for you or them to enter the other's dorm. That means, by the way, that there is to be no sexual contact between you and any of the special girls, including your partner, if he is here."

The next morning, when shaving at the row of mirrors in the large communal bathroom, Frank noticed that several of the men, now special girls, seemed to be fussing in a very feminine way about their appearance. He told himself that this must be par for the course.

After walking to the classroom to which he had been assigned, Frank entered and saw a seat vacant next to Melanie. She looked at him with love and patted the seat to indicate that he should join her. They did not have time to even say good morning when the instructor, Melody Hayes, a middle-aged, trim-looking woman, walked in and stood straight at the front of the room. She was accompanied by a younger, auburn-haired woman, who had a girl-next-door warmth to her, Frank decided.

Miss Hayes, as she stated she was always to be called, introduced her prefect, whom she referred to as Grace Janson. She said that this would be their homeroom for the weekend's lessons, but that they also would be taught by Miss Smithers and Miss Carmody, "whom I understand you have already met."

"You will immediately do what you are told, either by me or by Miss Janson," Miss Hayes began. "You will remain silent unless called upon and you will not be excused to use the rest room. Take care of those needs in the ten minutes between classes."

"We've found that you all need lessons in ordinary social niceties such as writing appropriate thank-you and other notes," she went on. "I will distribute some samples and then I want each of you to take a sheet of paper on your desk and draft a thank-you note to your aunt for a birthday gift."

The class began to focus on reading the samples, and a few began to write the assigned task.

Melody noticed right away that a blonde woman named Isabel was whispering to the woman sitting next to her, named Ginger. The latter had hair of that color to match her name.

"You two there, who were whispering to one another," Melody said sharply. "Put down your papers and come up here right now."

The two shamefaced women proceeded to walk to the front of the room. Melody pointed to the two chairs on either side of her desk.

"Get up on your knees on those chairs," she ordered. Then she walked over and flipped up each woman's short plaid uniform skirt, exposing their shiny white panties. She looked over at Grace and the prefect then came over and carefully lowered each woman's white panties to just a little below her bottom.

"The prefect will now give you some strokes, so you learn to keep silent when you are instructed to keep quiet," Melody intoned.

Grace picked up her thin cane, stood behind Isabel, and flicked her wrist to give Isabel three quick sharp strokes on her bottom, aiming at the top, middle, and then base of the bottom.

Isabel felt the strokes then the sting as she cried out from the immediate and lingering pain. The same punishment was given to Ginger. Then as Melody and the class watched intently, Grace reached into the supply drawer adjoining the teacher's desk and took out two small cylindrical objects. The women—the "girls"—in the class immediately recognized that these were tampons.

Grace tore open and removed the wrappers, dipped the tips of the applicators into a dish of Vaseline on Melody's desk, and then took her hand and held open Isabel's bottom-hole. She then deftly slid the lubed applicator into Isabel's anus slowly but completely, carefully removing the applicator after insertion so that the white string hung out from Isabel's anal opening. She then performed the same application on Ginger's bottom-hole.

Finally, Grace pulled each girl's panties up. Melody then told them they could stand and return to their seats.

"You have all now observed one of our little punishments employed here for naughtiness," Melody said. "Isabel and Ginger now have tampons in their anal cavities. They will retain them until they need to have a bowel movement and then they will come to Grace or to Diana, our other prefect, who will remove the tampon and decide if the girl merits insertion of another based on her behavior and for how long she has worn the tampon.

"You special girls may not be as familiar with tampons, which are usually used by women for sanitary protection during menstrual periods and inserted into the vagina for that purpose," Melody explained. "Here we insert them anally as a punishment. The teacher or prefect who is awarding the punishment determines what size of tampon the girl or special girl will be wearing internally in her rectum and for how long."

The class, suitably amazed at the diabolical nature of just this one punishment they had witnessed, focused on their assignment. When Melody came by to review their work, she looked at special girl Sally's note and saw that she had crossed out and had previously written to the specified aunt that she thanked her and hoped when she next visited the aunt, she could thank her in person by licking her cunt.

"Sally," Melody Hayes said loudly and with some annoyance, "that is disgraceful! Stand and follow me to the front."

When the surprised Sally reached the front, she too was made to kneel on the chair next to the desk, and the prefect, Grace, duly lift his skirt and pulled his panties down his legs almost to his knees. The real girls in the class tried to conceal their amusement when they saw the G-string still holding his male parts.

Melody motioned to Grace to apply her cane to Sally's posterior. Grace stood behind the special girl, lay the cane on his bottom, and applied three strokes slowly this time to permit each to sink in and begin to sting. Then she applied two stingers crisscross the first strokes to create a "gate" pattern on his bottom.