Trans School

Trans School: Daughter's Arrival

Summary:My daughter visits and discovers the school's BIG secret.

Note 1:Thanks to Tex Beethoven for rejuvenating this old story and illustrating all the parts.

Note 2:This is the fourth part of a planned marathon series about my adventures at Chateau Johnson School for Girls in southern California.

Note 3: Please note that this story was originally written with illustrations, but new Literotica policies have made that no longer possible.

So, instead, I will describe the pictures that were originally going to be there. As with the previous part, feel free to e-mail me for a copy with the illustrations. Please be patient as it is a big file and I will send it as time permits.

In part 1, A TEACHER SEDUCED, I relocate from Canada to teach at a private school in extremely rural southern California, where I gradually unravel a secret... that the students are all trans. The cat is finally let out of the bag when I'm seduced by the virtually all-powerful trans Headmistress, then learn that as a result, I've just become the Bottom Slut to all my fellow teachers when I'm used by their former Bottom Slut. I then have a romantic-ish encounter with Amanda (the Headmistress's (very) personal secretary) Amanda, (where I get to do the fucking for a change, because she's even more submissive than I am), and Chapter 1 ends with my submitting to Nicole, the school's most dominant student.

In part 2, COCK WORSHIPPING, I am initiated by the senior trans students in a marathon suck and fuck session that lasts all day.

In part 3, COLLEAGUE WORSHIP, I am initiated as Bottom Slut by the entire female teaching staff in a lengthy lesbian sex-fest.

Trans School: Daughter's Arrival

It was a few weeks later when I got the biggest surprise of my life, and I'll get to that soon. But first, some backstory:

By this time, I'd somewhat gotten into a routine.

Every morning, before I got ready to go to my classroom to teach, I put on a pair of stockings (and nothing else) and went across campus to see Nicole for my morning treat.

Sometimes I blew her.

Sometimes she fucked me.

Sometimes she had Lisa join us for some double treats.

But it always ended up the same way... with a load (or two) in my mouth, or maybe on my face and my tits instead.

PIC 1: ME ON MY BACK (IN BEIGE THIGH HIGHS) WITH LISA FACE FUCKING ME IN WHITE NYLONS UPSIDE DOWN WHILE NICOLE IN RED STOCKINGS MATCHING HER HAIR FUCKED MY PUSSY.

PIC 2: ON MY TOES, BENT DOWN, MOUTH OPEN AS I TAKE TWO FACIALS. ONLY LISA'S JUICY COCK EXPLODING CUM IS IN VIEW.

Then I'd return to my own room (yes, a daily cum walk), clean myself up, get dressed, and go teach.

Now that the full hierarchy had been established and the amended rules were now being followed... amended because all the seniors and all the teachers had now been initiated (I'd been the final teacher), anything outsiders would consider inappropriate still didn't occur during school hours... not even during lunchtime. No change there, but read on.

Maybe right after my last class of the day, and definitely after supper, I spent every night taking at least one cock inside me... usually two or three... plus it was rare when I didn't also service at least one of my fellow teachers' pussies.

Each Saturday was Cum Dump Day, which I spent on all fours on my bed between the hours of noon and three o'clock, and lots of my students came into my room simply to fuck me from behind and dump their loads inside me. I was blindfolded the entire time, and there was no talking. Then afterwards I was tested whether I could guess who'd fucked me, and in what order.

PIC 3: ON MY BED IN RED STOCKINGS AND BLINDFOLDED AS I GET FUCKED FROM BEHIND AND TWO OTHERS WAIT FOR THEIR TURN.

Needless to say, by 3:00 my pussy was always a veritable swamp!

PIC 4: A CLOSE UP OF MY CUM FILLED CUNT.

It was always an exhilarating day... although by the end, my knees were aching.

On the first Saturday, I guessed only two of the girls correctly.

Which meant the Cum Dump Saturdays continued... until I could succeed in naming all the cocks in the right order.

Which wouldn't happen until May.

Anyway, that's not what this story is about.

No, it's about the big surprise I mentioned at the top... what happened two weeks after my cock and cunt initiations. (Which were described in Chapters Two and Three.)

But to tell this part of my story properly, I needed to interview my daughter, Headmistress Alexis, and Amanda, to learn all the details of what happened before I arrived in the Headmistress's office and learned... to my astonishment... that my daughter was on campus instead of still in Toronto! So I'll write the rest of this chapter from the omniscient point of view.

So here is my daughter Tiffani's story...

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.....

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Moving to Toronto to attend college had deliciously awakened Tiffani's sexuality. Coming from a much smaller town in Alberta (which isn't nearly as cosmopolitan as Ontario), she'd kept her lesbian curiosity a closely guarded secret... even from her family... including her many fantasies, and her avid fascination with watching porn and reading erotica. She wasn't a virgin when she left for the big city, since she'd lost that to her boyfriend Pablo. He was an oversized Hispanic linebacker on her high school's football team, so at the time she'd considered him quite a catch. Her first time was a month after she'd turned eighteen, on prom night. It happened in a nice hotel.

It had lasted all of three minutes!

She didn't even come close to having an orgasm!

She was super annoyed, given the money and effort she'd put into the lingerie she'd been wearing beneath her prom gown. (Black lace bra, a garter belt, matching black stockings, and of course, no panties.)

PIC 5: TIFFANI ON HER BACK IN LINGERIE AND STOCKINGS IN A HOTEL ROOM BEING FUCKED BY A CHUBBY HISPANIC MAN. TIFFANI'S TRADEMARK (WELL THEY WOULD HAVE BEEN IF THE PICS WERE ALLOWED) GREEN GLASSES IN VIEW AS SHE MOANS IN ECTASY.

Needless to say, she dumped Pablo immediately.

Then, when she moved to Toronto, Tiffani decided to let the freak inside her out to play before she started college.

She went to a glory hole and sucked three strangers' cocks. Two of them shot in her mouth, and one on her face.

PIC 6: TIFFANI AT A GLORYHOLE SUCKING A BIG FAT FUCKING BLACK DICK.

She then went to a lesbian club, got picked up by a pretty woman in her fifties, and was taken back to the woman's house, where she ate her first pussy, and hers was eaten, resulting in her first orgasm ever that wasn't stimulated by her own hand or a toy.

PIC 7: TIFFANI AND A GREY-HAIRED WOMAN TRIBBING ON A BED. TIFFANI IN SEXY YELLOW STOCKINGS, WHILE THE GILF IS IN BLUE STOCKINGS AND A SEXY PIECE OF LINGERIE.

While Tiffani was leaving the house, she passed a man, presumably the woman's husband, asleep on his reclining chair with the television still on. (She thoughtfully turned it off for him before she left.)

During her first year of college, Tiffani explored her sexuality by dating both men and women. She indulged in a few wild encounters during her freshman year, including taking part in a gangbang with a girlfriend, and also seducing the mother of one of her boyfriends (while he watched from the open bedroom door), and pegging one of her short-term boyfriends in a log cabin in a forest.

PIC 8: TIFFANI SUCKS AND GETS FUCKED WHILE HER BLACK FRIEND DOES THE SAME.

PIC 9: TIFFANY ON A BED KISSING AND TOUCHING A MILF'S PUSSY (SHE IS ON HER BACK) AS THE BOYFRIEND WATCHES FROM THE DOOR IN SHOCK. A VERY SEXY PICTURE.

PIC 10: TIFFANY IN GREEN STOCKINGS PEGS HER BOYFRIEND IN A REALLY ROUGH PIC.

Then during her sophomore and junior years, she settled into two serious relationships. One was with a guy named Matt, and the other was with a girl named Mary. (She didn't cheat on them... each of them knew about the other... sometimes more than they wanted to know!)

But as Tiffani's senior year began, she was single again and was in no hurry to invest herself in another serious relationship. At first, she was hoping just to find a no-strings fuck buddy for those lonely nights, plus maybe a submissive girl who could please her whenever she needed a lesbian fix. But alas, neither of those stopgaps happened, so a month into her final year she was enduring some serious sexual frustration.

To tide herself over, she watched an unhealthy amount of porn (either lesbian or gangbangs, depending on her mood). She decided that if she had to choose only one, she'd want to be with a woman. They ate pussy better by far, and although she presented a shy nerdy look to the world (including to her mom), she was mostly a dominant in the bedroom (although she could also be submissive if the situation arose). On the other hand, whenever she was with a man (or more than one), she was usually submissive.

As has been mentioned, Tiffani read a lot of erotica, especially stories written by a woman (at least allegedly, you couldn't ever tell for sure on the Internet) who called herself silkstockingslover. She (for the sake of argument) wrote in a lot of different genres, and it was often really kinky shit! While Tiffani knew she'd never commit incest herself, the writer's sex scenes were so hot that she often came while reading about a son fucking his mom, or a daughter dominating her mom. A few of her stories had also gotten Tiffani curious about being with a BBC, which she hadn't yet found any opportunities to explore, and she'd also begun pondering the idea of being with a trans woman. In fact, a trans might be the perfect companion: she'd have the beauty of a woman, plus the thrill of a cock.

Tiffani found it interesting that all her favourite author's stories featured nylons. Ever since she started high school, Tiffani had always worn nylons... which was maybe her mom's fault, since her mother had worn them almost every day for as long as Tiffani could remember.

The following discourse illuminates Tiffani's growing concerns that soon led to her entire life being turned upside down.

"You're sure nothing is wrong?" Tiffani asked after a couple minutes of generic 'How are things going?' questions, and received nothing but vague answers in return. Her mother had to be hiding something from her... which sheneverdid!

"No, things are going great down here," her mom answered, still without giving her daughter any details. She seemed preoccupied... just like she had the last couple of times they'd chatted.

"You'rereallysure?" Tiffani asked again. She was very concerned! Her mom had recently skipped their regular seven PM call (California time, which was ten PM in Toronto) three days in a row, which was very unlike her. There was also something odd and guarded... as if she felt the need to censor herself... in her tone, and in everything she said.

"Yes I am,honeeeeey," Jasmine answered, trying to stifle a moan.

"Mom!" Tiffani blurted out. "You sound awfully strange!"

"I'm just fine, honey," Jasmine said, trying to control her moans while taking a big dick in her well-fucked pussy. "I'm just a little stuffed up at the moment," which made Nicole smile at the wicked sexual innuendo the oblivious daughter would never catch onto.

PIC 11: I AM STANDING TALKING ON THE PHONE AS NICOLE FUCKS ME FROM BEHIND. BOTH OF US IN SEXY LINGERIE AND, OF COURSE, STOCKINGS.

"Okay," Tiffani said helplessly, not believing a word of it. Her mom obviously had some sort of elephant in the living room she was hiding from her daughter, which greatly annoyed Tiffani, so she wasn't at all okay. But there wasn't much she could do, since she lived thousands of miles away. Tiffani hated that her mom had moved to California... it was sofuckingfar away! Sure, her mother had hated it when she'd left Alberta to attend college in Toronto, but kids aresupposedto leave home... not their parents!

"Can I call you back a bit later, honey?" Jasmine asked. Her orgasm was rising, and she knew she wouldn't be able to control her moans for much longer.

"Uh, yeah, sure," Tiffani said. "But please remember I'm three hours ahead of you, and I have classes tomorrow morning."

"Okay, thanks honey," Jasmine responded abstractedly, and she hung up without saying goodbye, desperate to focus on the dick inside her. "Oh, yes Nicole, give me that dick!"

"That was so much fun... and so hot!" Nicole said delightedly.

"Then pound my pussy and give me your big load," Jasmine demanded, shifting smoothly from secretive mother to wanton slut.

"As you wish," Nicole said, making her deep thrusts faster before she dumped her load into her hot teacher a couple minutes later.

That so-called conversation was the last straw for Tiffani! Her mom was acting stranger and stranger every time they talked, and she was giving her nothing but brief and vague answers to all her questions. And even stranger, she'd stopped asking the plethora of questions she'd always asked about her daughter's school and her life... plus the phone calls recently were way shorter!

While Tiffani couldn't pinpoint what it might be... there was something really off with her mom... she was acting differently... secretively... maybe even guilt-stricken... and Tiffani was becoming very concerned about her wellbeing.

So without giving her mom a word of warning, Tiffani booked a flight to sunny California. Partly to find out whether her mother wasreallyokay, but also partly to take a break from her college routine for a few days.

This was Tiffani's final academic semester before beginning her internship to become a fully accredited teacher, so she could only get away for a few days. Just before she left, she worked her ass off to get a bit ahead, and then she flew off to see her mom, hoping to surprise her, and to make sure she hadn't gotten herself brainwashed, and then idiotically joined some cult.

On the other hand, Tiffany had to admit to herself that maybe she'd just talked herself into a panic about nothing. She knew her mother very well. She was a sweetheart, but she was also rather boring, and she wasn't ever a risk-taker. Tiffani had recently watched Quenton Tarantino's Once Upon a Time in Hollywood, and it had planted seeds of concern inside her that maybe she was now blowing out of all proportion.

Her flight landed in Los Angeles early... which was a first in her life... then she picked up a rental car and drove three hours East to this remote (and thus mysterious) private school, where her mom was now teaching. The entire time, she kept thinking it was very suspicious that such a prestigious school (she'd looked it up, and she'd encountered a very impressive list of alumni) would be located so far away from civilization.

She found the school (thank goodness for GPS) and parked in a spacious but almost empty parking lot. The buildings on campus looked like they were very recently built and well-maintained, as were the spacious lawns. She followed some prominent signs that directed her to the Visitors' Entrance.

Tiffani went inside and followed some more signs to the Main Office, assuming that at 2:30 in the afternoon, her mom would be teaching. It would be fun to surprise her by just strolling into her classroom, but first, she'd probably need to get permission from someone, and also find out where her classroom was.

Tiffani was certain those very clear signs had led her to the right desk (there was a placard on top of the desk reading Reception), but there was nobody sitting there, so she tapped on the old-fashioned bell, which made a nice loudding. She then waited for a couple minutes, while she admired the pictures of alumni hanging on the walls. They were incredibly impressive! The high school she'd attended had once graduated a boy who'd gotten into the NHL, and a girl who'd appeared on the short-lived Canadian Idol. (She'd finished fifth, and was now a waitress at a local bar.) It certainly hadn't graduated anyone who'd... for instance... gone on to become anything like a U.S. Senator!

The door to what was obviously an Inner Sanctum opened, and a very pretty blonde came out, with what was clearly cum on her face!WTF?!Tiffani thought to herself.

PIC 12: A PIC I LOVE LOVE LOVE. AMANDA WALKS OUT OF HEADMISTRESS'S OFFICE IN A SEXY DRESS SO SHORT IT REVEALS ALL HER YELLOW-GOLD THIGH HIGH STOCKINGS... BUT MORE SCANDALOUS IS THE MASSIVE LOAD OF CUM ON HER FACE. TIFFANI IS DRESSED CASUALLY FROM THE FLIGHT AND DRIVE AND IN UTTER SHOCK.

Amanda asked (as if there wasn't anything scandalous on her face), "Good afternoon, Miss. May I ask what you're doing here?"

"Um... I... well..." Tiffani stammered, totally flabbergasted by the load on this woman's face, "...I'm here to surprise my mother."

"Your mother?" Amanda asked, trying to figure out exactly who was standing in front of her.

"Yes, Jasmine Winston," Tiffani explained, still processing the surreal situation she'd suddenly found herself in.

"Oh my," the secretary said, instantly processing how to deal with this suddenly unorthodox situation. "Well, that will be a pretty big surprise indeed!"

"I was hoping it would be," Tiffani said lamely, as she got a really good look at the massive facial. Jesus! How could the woman walk around looking like that? At work!

PIC 13: A CLOSE-UP OF THE SEXY AMANDA WITH A FACE FULL OF CUM.

"Well, she's teaching right now, but I'm certain Headmistress Alexis will love to meet you," Amanda said, knowing she had to inform the Headmistress about their surprise visitor right away! "Just give me one moment, if you please." Her impeccable courtesy was completely at odds with her scandalously decorated face.

Tiffani shook her head in puzzlement as the secretary went back into the Inner Sanctum and closed the door behind her. Tiffani pulled out her phone and found there wasn't any service. Her creepy cult suspicions were emerging again, given those two strange revelations... the cum and lack of any cell service... within just the first couple minutes after she'd met someone.

A minute later, Amanda returned with instructions from Headmistress Alexis, and she said warmly, "She'll see you, but first you'll need to change."

"Change?"

"Yes, we have a very strict Dress Code, and we require all students, employees and visitors to abide by it."

"Oh! Even your guests?" Tiffani asked. This policy seemed very unorthodox.

"Yes, it's a long-held tradition here. It goes way back to the foundation of the school!"

"And whatisthe Dress Code here?" Tiffani asked, kind of curious. For a secretary, this pretty lady was dressed very nicely, even wearing nylons, which she wouldn't expect to find in a locale where the climate was so hot.

"It's not very complicated, actually. You just need to put on some nylons," Amanda answered. "Which I can easily provide. What colour would you like? I have a very large selection you can choose from."

"Really?" Tiffany asked, nylons being something of a relic in today's society. She'd begun wearing them sometimes, inspired by her favourite writer of erotica, who mentioned them in all her stories, anddefinitelynot because of her mother, who'd also always worn them. She couldn't deny they succeeded in enhancing her legs, and they drew favourable attention to her from both men and women, just like the author frequently said they did. Deciding to choose a very unlikely colour option to test the claim that they had averylarge selection to choose from, "Do you happen to have them in purple?"