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Chapter 18
by
SamanthaDane
A letter from Prude World and life with Tommy and Tracey
Tommy’s first days at school
Tommy was dressed in an outfit picked by his girlfriend Samantha Dane. It was a long sleeve, rainbow colored, mini fishnet dress. It hugged his slender feminine frame accentuating his curves and making his butt pop. He wore no panties not seeing the need for them. His boots were a white thigh high with a 4 inch heel. His makeup made his eyes explode with sexual energy.
Tommy had been encouraged to explore his gender from the time he was adopted. Tom and Tiffany taught him and his sister to live a sex positive lifestyle. As Tommy’s stiletto heels clicked he remembered his first panties, stockings, and teddies. The undies were from his sister, the stockings he bought himself, and the teddies were from Tiffany. After she had caught him in her closet. What surprised him was Tiffany was not upset or horrified but hugged him and was supportive.
Tommy loved his mother and father they were there for several important issues. Getting a driver's license right after their birth mother passed away. During that first summer, He and Tracey went to school-sponsored driver's education. Tracey dressed in short skirts and heels, while he went for a fishnet top shortly shorts and high tops. They both always had perfect makeup when they went to class. Tommy had a crush on his teacher.
Tommy arrived at the gym. It wasn’t that he hated P.E. On the contrary, he loved seeing everyone getting changed and comparing sizes and shapes. But this was to be a new experience, Tommy walked into the class like he owned the walk. He stop short when the students were all naked and running with dildos inverted into their butts. There were others in 69. Not just boy and girl, but girl on girl, and boy on boy. This was a little slice of heaven. Even more so than the last week's moving in party. Tommy’s ass started to tingle, his mouth was dry, and his cock smeller to its full 8 inches.
With a boom came, “All right ladies 10 more minutes we’ve gotta build up that cardiovascular build up that stamina. It’s all about maintaining hardness and keeping that heart pumping moving it move it move it. We’ll switch it another 10 minutes. You people doing the 69 get your faces deeper into those cracks, hit those important spots finally the clits guys it’s the most important fee feature girls. Make sure that that throat opens wide and takes all that cock all the way down your nose should be touching those balls every damn time. You ladies having sex hold off do not come don’t come for another 10 minutes until we make the switch.” There stood a Demigod 6-8, with broad shoulders, and a muscular physique that tapped to a hard butt and legs for days. The god rounded on Tommy “So you the new student from Prude world, what's your name?” It took Tommy a moment to remember how to talk, he couldn’t take his eyes off the thickest and longest cock he had seen. It had to be 4 inches wide and a foot long if not more. “I’m sorry yes I’m Tommy Armstrong”. “Excellent Tommy the office said you like to be fuck in the ass, well that's what we do in gym class. Now bend over while I fuck your tight boy pussy”, and Tommy was anal rapped in front of the class. “Mr. Armstrong, we are half done I will assign you a locker tomorrow, so have a seat and observe. You can call me Mr. Mann.” Tommy found himself in the gym but not being ****.
Tommy sat on the bleachers watching the naked Demi god a.k.a Mr. Mann with a student doing doggie style. He pulls the boy out of the girl's ass and thrusted her monster hard and fast into the redhead. The girl screamed “Holy fucking shit!”, Mr. Mann smiled “See that is the response you should get every time.” He pounds the redhead's ass in and out, never giving the girl a moment to recover. He keeps stretching the young woman’s pucker hole. Tommy wish it was him taking all that lovely hard throbbing cock up his bum.
Then “Armstrong come here get on all fours this young man needs help and you are the only one not engaged.” Tommy walked out to where Mr. Mann was hearing the guy say “I didn’t do guys!” Tommy was pissed at such wanted disrespect. “Who says I’m a guy” dropping to his knees and inhaling the guy's cock in one go. All 8 inches without gagging. Tommy made the cock wet and sloppy, “Well done Armstrong way to take control. Now Phawker here’s how to fuck an asshole or repeat the year, again.” He went in hard a fast with lots of lube. “Holy fuck!” Moaned the redhead. “See Phawker that’s how it done.” Tommy positioned with his butt high up to expose his pink pucker hole. Phawker set the tip against the hole and pushed. The pain was too much for Tommy he flipped out doggie then had Phawker on the mats grabbed the lube used a generous blob and found Phawkers prostate and pounded it hard. Phawker moaned I’m coming” Mr. Mann “That’s the way Phawker give it to…” seeing Tommy on top riding with enthusiasm and abandoned. Mr.Mann smiled “Way to go Armstrong make him your bitch.” Tommy felt powerful he whisper “Now your my bitch, I own your mouth, ass, and cock. When you see me you will kneel and suck me off, if it’s lunch then I get your ass like now.” Phawker didn’t say anything not sure if it was a joke. Tommy dropped several gallons of femboy jizz in Phawker’s ass. When Mr. Mann called the class.
“Excellent work ladies A+, now I want to give a shut out to Tommy Armstrong new student from Prude World who is a natural butt fucker. Showed a native how to fuck. Hit the showers you got 10 to the bell.” As the rest of the class headed for the shower Mr. Mann approached Tommy. He pulled Tommy into a loving embrace and kissed Tommy. Tommy felt the floor disappear as Mr. Mann positioned Tommy onto his lubed cock. “I live femboy they make no bone they want cock. You want cock don’t you?” Tommy just nodded yes Mr. Mann pushed 4 inch wide crown into Tommy. Tommy moaned and smile up into Mr.Manns face “Fuck me, Daddy”. Mr. Mann pushed all 14 inches and stretched Tommy’s asshole super wide. Tommy was in heaven, in and out up and down. Tommy had his feet locked behind Mr. Mann’s head as he used Tommy like a jerkoff toy. “Phawker this is how you fuck anal,” said Mr. Mann. Then there was a grunt as Mr. Mann rabbit fuck Tommy’s boi pussy. It felt like a fire hose full of cum blasted into Tommy’s belly. Mr. Mann held Tommy tight “That was incredible what are you doing after school?”. Tommy smiled “I hope to go on a date with a handsome P.E. Teacher”. And they kissed.
Rest of the day
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Moving to the Sexworld
Adventures in a Sexy Alternate Universe
An ordinary family immigrates to an alternate reality without sexual taboos
Updated on Oct 13, 2025
by Shendude
Created on Dec 19, 2010
by Shendude
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