The Girls College Ch. 02

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The lesbian tailor takes a liking to Paul.
4.4k words
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Part 2 of the 10 part series

Updated 06/08/2023
Created 08/09/2017
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TF2123
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The car drove through the huge front gates to London Girls College, parking itself in front of a large brick building with a triangular metal roof. Large blue metal letters above the big wooden doors spelled out "The Jane Marwood Hall". Above the letters was a large dark blue insignia with white letters on it reading "LGC".

"Paul," spoke the voice of Miss Smith, Paul looked at her and saw her left hand slowly creeping towards him. He didn't do anything to stop her as it wrapped itself around his flaccid shaft, starting to gently rub it. "From this point on, you address me as Headmistress, because that is what I am to you from now on. This school is run exclusively by women, and the boys that are admitted to it should be very thankful to us. You, as the only boy in your year, will spend your entire stay at this college displaying your gratitude to us. By us, I mean every single young lady and woman that graces the school grounds with their feet. Females are royalty here, and you will treat us as such. Understand?"

Paul's voice had been taken away at the gentle strokes she was applying to his penis, and he could only manage to reply with a quick nod. This obviously didn't impress the blonde lady, who quickly moved her hand from his shaft to his scrotum, pinching a piece of its skin between her manicured fingernails. He squirmed as she did this.

"Tut-tut," she said, shaking her head slightly. "Answer me properly now."

"Yes- Yes, Headmistress," he uttered as her hand started to play with his manhood again.

Paul's eyes shifted suddenly to the rear view mirror, seeing the reflection of the driver's eyes looking at him in the nude. He could see enough of her face to know that she was taking pleasure in having him humiliated before her, signs of a smile visible on her face.

"Good boy," said Miss Smith, talking to Paul as if he was a dog. "Judy will take you to the school tailor so we can get you fitted for your uniform. I will be seeing you soon."

The driver, whom Paul now assumed was called Judy, opened the driver's side door and hopped out, also opening Miss Smith's after she had closed hers. Miss Smith got out of the car and Judy closed the door behind her, he watched as they spoke briefly before the blonde walked off and Judy stood alone, gesturing for Paul to get out of the car.

He opened the door on his side of the car and got out, resting his bare feet on the warmer cement for a few seconds before turning and closing the door once again.

"Hurry up," said Judy, and he heard the slender brunette's voice for the first time. It reminded him of Miss Smith's with its high pitch yet controlling undertone. He walked around the car and she stopped him, making him stand before her while she carefully examined him visually. Her soft hands reached out towards him, taking his own from covering his manhood.

"There's no need to cover that up, not like there's much of it to hide anyway," she said, looking at the exposed genitals of the boy before her. "You don't need to worry about your briefcase; it'll be brought inside by one of the workers. Don't get used to women doing your work for you though; you're only here to serve us."

With this, Judy turned around and Paul followed her closely, taking a look at her school uniform from the back. It was a very nice uniform, he thought, though he didn't expect college students to wear uniforms. She wore a light blue dress that covered most of the thigh but didn't reach the knee. Covering up the top half of her uniform was a white blazer and on her feet were white ankle socks covered by black leather Mary Jane shoes. The small heels of the shoes made prominent clicking sounds as she walked and he followed, trying his best to hide his nudity though he couldn't spot any nearby onlookers.

*****

They reached a small building next to The Jane Marwood Hall, the door was already open and Paul saw a woman sat behind a desk as he peered across Judy's shoulder into the building. Judy stepped inside and Paul followed her.

"A new student?" asked the lady behind the desk, in a gentle and friendly voice.

"Yes, Miss," answered Judy. "He's here to have his whole uniform fitted, as well as to have all his measurements taken."

"Perfect, nothing out of the ordinary," said the woman. "I see he's already nude as well!"

The two women shared a quick laugh before Judy wished her goodbye and turned around towards the door. The spectacled stopped briefly to look at Paul again, patting him lightly on the bottom as she left. Paul stood at attention, opting not to cover his manhood as he did previously to no avail. He watched as the skinny lady got up from her chair, she was surprisingly tall. She brushed her short hair from her face as she walked towards him.

Miss Ellie Finch was very pretty, and looked much younger than she actually was. Now deep into her fifties, she barely looked a day over forty. She had short hair which was naturally blonde but dyed silver and cut into a classy bob style. Ellie was wearing a dark grey dress that hung below her ankles but didn't fail to show off her leather sandals that her long, slender feet were clothed in. The colour of her dress matched the colour of her fingernails as well as toenails almost perfectly.

Paul didn't dare move or speak as the tall woman circled him, her hand rubbing her chin softly as she examined him with her silvery eyes.

"Stand on the table over there," she said, directing him to a low wooden table, similar to the one he had been stood upon earlier in the cellar, with her long index finger. Her cheery tone she spoke to Judy with had disappeared and the gentle voice turned into a sterner one while still keeping a slightly gentle twist to it.

Paul didn't object, and hurried over to the table as the woman walked back to her desk to retrieve something. He stepped onto the table with his right foot first, and climbed on top of it, turning around to face the lady as she approached him once more. She was now holding a clipboard, pen and measuring tape.

The items in her hands were placed on another table nearby, and she walked back to her desk to retrieve other items from the drawer. Her hand emerged from the drawer, pinching a pair of latex gloves between the thumb and forefinger. The drawer was closed, and she walked towards Paul again, pulling the gloves onto her large hands so they fit onto them snugly. At their sight, Paul remembered about the pain still half-present in his backside, inflicted by the gloved hands of his new Headmistress.

"You're going to stand completely still until I allow you to move around, is that clear?" asked Miss Finch, pulling the glove on her left hand a tad tighter.

"Yes, Miss."

"Miss Finch."

"Yes, Miss Finch."

She smirked as she heard him say this, she loved her job. It felt great to have these boys submit to her and obey her commands. She loved spending as much time as possible exploring their bodies with her gloved fingers. Not that she was attracted to these boys at all, she much preferred people of the same sex as herself. It was just so enjoyable to put men in their rightful place, at the mercy of a woman.

The tall lady crouched down below Paul, so she was at eye level with his feet. She started examining him with her gloved hands, feeling each of his stubby toes and rubbing the tops of his feet lightly. Next she moved to his calves, running her hands up them while gripping them tightly. She slowly raised herself up as her hands now ran up his knees and then reached around his legs to feel his firm bottom. It was surprising how firm it was, much like a lady's, but this feminine feature didn't surprise her when looking at his body as a whole. The only body part she avoided was his dangling privates, as she ran her hands around his entire body. Paul was very confused as to why she was doing this, but he very much kept his thoughts to himself.

"Sit down, lean back," she said nonchalantly, and watched as the boy obeyed. He sat down slowly, so that his bottom was planted on the cold surface of the wooden table, before awkwardly leaning backwards so that his lower back, bum and thighs were uncomfortably rested on the table and the rest of his body hanging off it. Miss Finch shook her head at him.

"Feet up on top of the table, your head down on the floor, dear," she commanded, her tone turning slightly aggressive again. As he started to move around, Miss Finch wheeled a low stool towards the foot of the table so she could sit down.

Paul slithered himself halfway off the table, so that only his lower legs and feet were still mounted atop it. Miss Finch suddenly started tracing down the middle of his slightly dirty sole with her gloved right index finger, making Paul curl the cute toes of his right foot and let out a slight giggle. Though Miss Finch wasn't attracted to the opposite sex, she had to admit she found his feminine body cute and his little feet and toes immediately adorable. She was a keen, although closet, foot fetishist, but never quite felt attracted to men's' feet as she was to Paul's. He squirmed and giggled hysterically as she continued to absent-mindedly tickle his feet, trying to wrench them from her grasp but she kept them firmly in place. She giggled at his attempts of escaping her gentle torment.

"You do have some very adorable little feet. What did you say your name was, dear?"

"P- Paul," he stuttered through his bursts of laughter, the lady continuing to run her gloved fingers up and down his sole.

"Well, Paul, I must say you have enticed me with these," she said, and suddenly her dominance over him was gone. She stared attentively at her subject's soles. "I'm sure we'll have a lot of fun with them in the future, but I must get on with my work."

In the future? What she could've meant by that he thought to himself. His quick thought process was interrupted by a last lap of his soles by the pretty lady's fingers. She traced the outsides of both his feet with her fingers, and he giggled again. Though not enjoying the experience, he had to admit it was strangely erotic.

The lady finally let go of his feet, and his soles were uncomfortably tingling after her continuous light caresses of them. He saw her arm reach for the measuring tape she had placed on the nearby table. Her hands were out of his sights as her gloved fingers unravelled about thirty centimetres of the tape. The cold plastic tape measure was pressed against his right sole as Miss Finch measured the length of it.

She mumbled a series of numbers under her breath before moving the tape to his left foot, repeating the process again. After re-measuring both feet again, she put the measuring tape down on the table and picked up the pen to write down a 6 on the sheet of paper attached to the clipboard.

"Up on your feet," she said, turning back to the boy. He slowly got himself up again, stepping onto the table again and standing upright. "We need to get you measured for your dress now."

Paul's face portrayed a curious look as she said this. She simply smiled at him.

"Yes dear, a dress. This is a school for girls after all. Your penis doesn't make you an exception to the rules, in fact it does quite the opposite."

She got up from her stool and was at level with the boy's chest. Miss Finch, almost instinctually, tweaked both his nipples and produced a gasp from him. A smile appeared on her face again, taking the measuring tape in hand again.

Paul stood completely still, as her skilled hands wrapped the tape around his upper body. He stood like a statue as the woman took his body measurements, one by one, in no particular hurry. It felt like hours before she scribbled down her final measurement down on the sheet of paper, now filled with a list of measurements.

"That should be almost all," she said. "But Judy did explicitly say to take all your measurements."

She laid his flaccid shaft on the palm of her left hand. His testicles were rolled in between two fingers as she stared at it. Usually, she would find her subjects' privates nothing more than disgusting. For as long as she could remember, she was repulsed by the thought of male sexual organs. But as hard as she tried, she couldn't help but stare at his small parts as they balanced atop her palm. For the first time in her life, Ellie was aroused by a man's penis, albeit not in the conventional manner.

*****

He gasped as her hand gripped his cock suddenly; it was now free of the latex glove it had been encased in for the length of the procedure. It felt hot and sweaty around his shaft, as it slowly started to stroke it up and down.

"It is equally important to get an erect measurement as a flaccid one," said Miss Finch, for the first time ever gripping a boy's manhood with bare hands. Paul moaned as she stroked it sensually, realising that it was starting to harden. "Just relax."

This was, usually, the part of these procedures she either loved or hated the most. Getting a boy's penis to a rock hard state could only be properly done by manual stimulus. A lot of times she would have another boy from the college summoned to do the job. It was a humiliating experience for both boys that were involved, and it brought her great pleasure to watch them plead for it to stop. However, sometimes she would have to do the job herself. This repulsed her just at the thought of it, having to touch a young man's disgusting private parts intimately. But, just as she enjoyed looking at Paul's penis, she immediately loved stroking it too. The little moans that escaped his mouth only spurred her on to stroke it harder, more thoroughly, though not fast. She didn't want to bring the boy to an orgasm; her only goal was to get his penis erect. At least for now.

It didn't take long before the boy started squirming in his standing position, the mature lady's hand still masterfully working his member. She kept at it for a little while longer until it was obvious he was on the very edge. She let go, and Paul gave a sigh of disappointment, left on the verge of a climax with his throbbing shaft desperately bouncing up and down in need of just a slight bit of stimulus before erupting.

Unsurprisingly, his erect state wasn't much more impressive than his flaccid state. She could barely fit one hand around it; whereas she could easily fit two around other boys' she had measured before. The instrument she had used to measure his soft penis earlier was picked up again, once again being held against the length of his throbbing cock that was seeping pre-ejaculate from its tip. The fluids oozing from the shaking head of his shaft dripped onto the floor and landed perfectly in between her feet. She carefully took the measurement of his erect length, and scribbled it down next to the flaccid length on the sheet of paper riddled with other numbers.

It barely reached five inches, but as she turned to look at it again, there was just something so alluring to its small size and cute appearance that she couldn't quite describe. She swapped the measuring instrument she used for the length for the measuring tape for the girth. Her hand expertly wrapped the tape around his shaft and she checked the measurement. Once again, it was quickly written onto the sheet.

"That would usually be all," she commented, looking up at the panting boy that towered over her as she sat on the stool. He looked down into her silver eyes; his own conveyed a feeling of being unfulfilled. "Usually I would let you walk out of here with an exposed erection for the world to see. It would be so humiliating for you, I'm sure you'd hate it. However, since you've behaved so well and proven yourself worthy of it, I think you deserve a proper finish, don't you?"

"Yes. Yes, Miss Finch," he said, his tone was basically pleading for it now.

He watched in anticipation as she got up from the stool once again, walking to her desk and taking another pair of latex gloves from the top drawer. Miss Finch knew of the possible repercussions that an activity like this could entitle, but they didn't bother her too much in her aroused state. She wasn't thinking straight, and she knew she would probably regret it if she got caught, but she was very interested in this experiment and didn't want to stop now.

"Very well then," she said. "Off the table."

He carefully stepped off the table, and his feet made contact with the cold floor again. His eyes were locked onto the woman in front of him, as she pulled a latex glove onto each of her hands. Her slender fingers were enveloped by the soft, white material again, and she tightened both gloves to ensure they were snugly wrapped around each hand.

She circled the boy, until she stood closely behind him. He felt the soft material of her grey dress press snugly against the bare skin on his back and bottom. She pushed herself up tightly against him, and her arms wrapped around his front. Paul looked down as Miss Finch's thin right hand slowly wrapped itself around his erect shaft. Her left hand started to fondle his scrotum as her right set to work, slowly, on his cock.

Paul moaned as she slowly stroked him, her hand firmly gripping his erection. She tickled his scrotum with her other hand, making him squirm in her grip. Miss Finch could feel him shaking as she stimulated him with great expertise, though it was the first time she was ever milking a boy of his semen.

"Do you like it, dear? Does it feel good?" she sensually whispered in his ear as he moaned.

Her question was answered by a series of moans, as they crescendoed from his mouth and filled the small room. She smirked to herself; clearly she was doing a good job for a first-timer. Ellie's hand slowly picked up the pace of her strokes, and she felt as the boy's testicles tightened. Waves of arousal started to flow through Ellie's body as she felt the boy's body tense up multiple times. She started to grind against his backside, and he felt the soft material of her dress start to rub up and down his bottom. Soon Ellie was also moaning and whimpering, this somewhat spurring her on to stroke his shaft as quick as ever.

Paul's eyes closed as he felt his own scrotum contract inside Miss Finch's gloved hand that was fondling it. He moaned at his loudest as he felt his climax nearing, surges of sexual pleasure running through his lower body making his toes curl where he stood. The lady continued grinding herself on his backside as his scrotum tightened and he felt the first wave of his climax come over him. Miss Finch looked down to see the first spurt of semen erupt from the tip of his glans. It was the first time she had ever brought a boy to climax with her own hands, and she couldn't help but look as another, and another, and then another spurt of milky white fluid shot with great force from his throbbing shaft. His body went limp in her arms as she continued to milk him of his fluids. She helped him to his knees and he stood on them, out of breath and panting.

Miss Finch was still very aroused and could feel her crotch start to become wet. She could feel the fluids as they seeped from her vagina into her silk panties, the latex-clad hand that had been playing with the boy's scrotum shot to her crotch and rubbed across it vigorously as she bit her bottom lip. She wrenched it from her crotch, keeping herself calm as she approached the boy.

He didn't look up as she walked to stand in front of them. She looked down through her rectangular glasses and saw the pool of seminal fluids that had shot from the tip of his small penis. Then, she looked down at her gloved hands, her right palm covered in milky white liquid. She hated it, the sight of semen. Not even the fact that it had come from this boy she was strangely attracted to helped this fact. She nearly gagged as she saw it, and quickly rid her right hand of the semen-soaked glove.

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