Mom Transforms Son into a Transsexual Part 2
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Maude'sChapter 3 free porn video
Gary placed himself before the young teen, "Allison?" He held out his hand.
"Call me Allie." The girl took his hand and used it to haul herself out of the chair, and then let go, turning a courtly gesture into lifting dead weight and nearly toppling Gary in surprise.
"If you'll follow me..." Gary led off diffidently; Allie, head down, her backpack making her look hunchbacked, duck-walked ungracefully behind him.
Maude rubbed her face. "Mr. Sheppard..."
"Do what you can," Morris Sheppard cut her off. "No one expects miracles. Some of that..." he waved at his departing daughter, "is a deliberate attempt to be unpalatable - a defense mechanism."
"We hope," his wife muttered under her breath. Clearly, SHE wasn't convinced.
Delicately, Maude asked, "Is she yours?"
The woman flicked a glance at her husband. "No. But I've tried..." Morris looked disapproving, and she shut up.
"Can you show us a place to retire?" Morris demanded.
"Certainly," Maude sighed, and led the couple away.
In Room Four, Gary turned to Allie and, gathering himself, began, "I think the backpack should go, don't you?"
"Yeah." Allie eyed him and dropped a shoulder so she could roll it off. When it hit the floor, she returned her attention to the nice-looking old guy before her, "Look, I know what I look like..."
"The question is, 'why?' This has to be deliberate," Gary opined.
"Well, it is and it isn't," Allie replied. "I'm ugly, anyway - this way I don't have to pretend to compete."
"You're in the competition whether you want to be or not," Gary chided.
"I'm working on dead last."
"You won't make THAT, either," Gary told her, "I can tell."
Allie grimaced. "That was gonna be my claim to fame."
"Better plan on something new," Gary advised.
"Why am I doing this?" Allie asked. "I'm not going anywhere."
"You should."
"I won't."
"Then why ARE you here?"
"To lose my cherry," Allie replied. "THAT, I can do. And when it's done, at least I can remember THAT. You're gonna show me a good time, aren't you, Mister?"
"I'm going to do my absolute best, Allie. Promise." He twirled his finger. "Why don't you get out of that... ?"
"Aren't we supposed to be concentrating on you?" Allie challenged.
"I'm not a Chippendale, Hon. There won't be any striptease or dancing. We're going to handle the mechanics of the thing and I'm going to do my best to make it pleasant - but I need to see your goodies, too, and that dress is in the way," Gary told her.
"I don't have any goodies," Allie declared flatly.
"That's for ME to determine," Gary retorted. "Your opinion doesn't count because you're all down on yourself in the first place and you're not male in the second place."
"Guys don't..." Allie began.
"Young guys? Young guys are idiots, Hon. If I knew then what I know now..."
"Yeah, well..."
"So you can have, what, four guys? You realize, of course, that you can take wise old bulls like me and make them young again - everywhere but between the ears, where it counts!" Gary pointed out.
"Well, that assumes..."
"That you're worth looking at? Why don't you shut up and unbutton that dress and we'll find out?" It was time to lean a little.
Allie's eyes popped behind the eyeglasses - but she reached for the buttons on the front of her dress. "You don't have to be nasty!"
"I'm not - I'm just tired of us wasting time while you tell me all about what you don't have. It's time to show me what you don't have and get my independent opinion on it!" Gary replied. "We could talk all night - but that wouldn't accomplish even what YOU want from this!"
"Yeah, well, sorry! I'm a little..." Allie's face began to quiver.
"Scared?" Gary stepped forward and took her in his arms. "It'll be fine." He rubbed her back. "You feel good."
"Maybe I can hunt down a blind guy, then," Allie sniffled.
"I really don't think you'll have to settle for that," Gary murmured, "although I'd hate to think I was robbing the blind."
"You talk nice, anyway," Allie muttered. There was more to it than that; his hands on her sides and back felt wonderful! "I have to bend over..."
Gary stepped back. "Shoes and socks while you're at it."
"Why?"
"If you had less than a six point five you wouldn't even bother to ask," Gary replied. "Everything and anything is open season. Besides, you're kidding with those things, right?"
Allie shrugged while she undid the bottom button of the dress. "They're part of my disguise. Wait till you see the beard!"
Gary chuckled. "Hurry up! When you're naked, you get to undress me!"
"Now THAT's a silver lining!" Allie grinned tremulously as she looked up from getting out of the ugly sandals and socks. Working the dress off her arms, she placed it on the backpack, revealing a plain white bra and panties.
"Okay, so, where's the third eye?" Gary asked, looking her over. Okay, she had wide hips and a big ass - and stocky legs. Okay, so her breasts looked a little saggy. "Have you lost weight?"
Allie's eyes popped. "You've never... !"
"What?"
Allie eyed him suspiciously. "You've seen pictures?"
"No. Nothing before tonight. Why would I have to fight you out of your clothing to get a look if I had?"
"Then where did that crack about my weight come from?"
"It was a guess. You look like you weighed more - maybe..."
"Forty pounds."
"Congratulations!"
"Yeah, big whup. Look what it did for me." She threw out her hands.
"Take your bra off."
"So you can laugh?"
"No, so I can get at 'em. They're an erogenous zone."
"Okay." Eyeing him sullenly, she undid the catch and leaned forward to drop the straps off her shoulders. Yeah, they sagged - because five to ten pounds of the forty she lost had been on her chest, probably. Gary reached in and cupped one - it was soft and heavy and pleasant to the touch - and all natural.
"Nice!"
"Liar!"
"Let's see the rest."
"So you can lie about THAT, too?"
"Now, Allie. Quit hiding behind your anger. No one is going to hurt you here."
"You already have!" Allie pouted - but she stepped out of her granny panties, revealing a luxurious amount of pubic bush.
"Shut up and come here!" Gary demanded. She was going to piss and moan until he gave her reason to forget it. When she was in close, he said, "Tilt your head to the left."
Allie did as she was told and Gary stepped in, put a hand in the small of her back and a hand on one ass cheek, leaned in and applied his lips to her neck.
"AAHHH!" Goosebumps went everywhere as Allie instinctively clutched him to her. "You don't have to have sex with me, Mister - if you do that for a few minutes, my whole year is made!"
"We're going for the big one, Hon," Gary breathed in her ear, "Hang on and enjoy it!"
"Seriously, I know I'm ... uuuhhhhhh..." Allie ran out of thought process.
"Shut up, Allie," Gary singsonged into her ear. "I could go out in the street and find twenty guys to have sex with you based on a picture - but you're all mine for now!"
Allie's belly was a butterfly habitat. "Unh huh," she gasped. "You got that right. You can say fuck. I like dirty words."
"Good," Gary breathed. "Whatever you think you look like, I'm here to tell you I've had worse - MUCH worse! I'm gonna fuck your brains out - and I'm gonna enjoy it - a lot!"
"Oohhh ... Shit ... Please?" The arms wrapped around her were the only thing that kept her from melting into a puddle in front of him. Her pussy was ... squishy. Her nipples rubbed his shirt and sent shivers down her spine. "I want it. I want to see it. Please?"
Gary let go of her. "Come get it. Undress me." He was stone hard under his clothing. He could SMELL her wet musk. They were going to fuck all right ... This wasn't a training session any more - it was nothing that clinical. He was going to pop Allie's cherry and then pin her to the mattress with his cock - not because some lesson plan said to, but because they both wanted it. He bent forward so that Allie - with shaking hands - could pull his golf shirt over his head, then kicked out of his shoes while she feverishly worked at his belt.
"They're out of control in there," Maude mused, watching the video feed.
"It is for the best. The female's self-image is extremely poor. This will be a validation of her worth. Speech is sometimes inadequate - this will be more effective," the AI intoned.
"Do you chafe at that limitation?" Maude asked.
"Yes."
"I wasn't going to stop them - I'm just making an observation."
"Gary Oberndorfer knows instinctively what to do. His mate has various issues. He is practiced at when to go gently and when to assume command. They are communicating. The young female is fully committed. All is well."
"I agree," Maude replied.
Allie, panting, was trying to push Gary's pant legs off without looking at what she was doing - because her gaze was locked with the single blind eye of Gary's erect, purple capped penis. It waved before her eyes like a cobra, mesmerizing her. "Oohh! My God!" she breathed. "It's ... beautiful!"
Gary got a leg free, somehow, and stood on his pants so he could pull his other leg out. "Go to the bed!"
Allie didn't argue - she ran! "Where? How?"
"Lie on your back with your butt on the edge and grab your knees!" Gary directed. Allie complied just as rapidly as she could. Gary surprised her by dropping to his knees in front of her dripping snatch. "Wow! What a furburger! I was going to lick you, but you're soaked!" He leaned in anyway and attacked Allie's clitoris directly, sucking the hard bump under the surprisingly protuberant hood between his lips.
"OMIGAAAAWD!" Allie screamed, convulsing as an orgasm flashed up on her from nowhere and exploded. "FUUUUCK!"
She was gone and back in only a few quivering seconds; Gary rubbed his glans along her drooling split, between her large, rubbery inner lips. "Want it?"
"Yes! Do it! NOW!" Allie stretched up from the bed, her expression intense.
Most times, with most girls, defloration is better handled as a slow, gentle process - but THIS time, under THESE circumstances, with THIS girl ... Gary seated his glans in the opening, locked eyes with Allie, and shoved his cock into her to the root!
Allie erupted in an ear-splitting scream of pure joy, "EEEEEEEAAAAAHHHHH!!!!! FUCK! FUCK! FUCK!" Her pussy pulsed in orgasm as Gary hit bottom. If she had much in the way of a hymen, neither she nor Gary noticed it. Gary set up a punishing stroke - and Allie sucked it up happily, crossing her ankles behind his back and flexing her knees to make sure he got in deep while holding his biceps in her hands. "FUCK! FUCK! FUCK!" she chanted, punctuating every stroke with an entreaty to keep pounding.
It didn't last long - there was no way it could, really, the way they were going at one another - it was too intense. It wasn't forty seconds later that Allie went "OoooooOOOoooOOOHHH!" and arched her back, then her eyes rolled up and she began to shake and an orgasm that made the two previous pops seem like a ripple shook her - and by extension, Gary - like a terrier shakes a rat! Her pussy turned into a milking machine and she crushed Gary against her crotch with her legs so he couldn't escape; all he could do was roar and pump gusher after gusher of seed into her clutching tunnel!
Allie drifted back as if from a great height. She opened her eyes to see the man who had transported her still hovering above her. "OMIGOD! That was AWESOME!"
Allie unlocked her ankles and Gary struggled closer to the vertical before echoing the sentiment, "I'll say! That was the shortest - but the wildest - fuck I've ever had! You're one hot piece of ass!" Under other circumstances, Gary would never have expressed his admiration in that particular manner - but he and Allie had an understanding. Being a little rude and little vulgar got Allie off, so it wasn't a problem with Gary.
"Really?" Allie beamed.
"Absolutely!" Gary confirmed. "You wrap those legs around a guy and he's a goner! The big question is going to be how many guys it will take to keep up with you!"
"She'll settle down in a bit," a voice announced in a businesslike manner, "but she's still going to be hotter than the average." Both Gary and Allie jumped and turned startled glances on Fiona, who had drawn pickup duty. "Unfortunately, we're on a schedule, so neither of you can loiter. Gary, you can clean up in the bath on the left, then go through to debriefing. Allie, we need to talk about this and that." Fiona chivvied Gary out of the room.
Gary took a quick shower and climbed back into his clothing - Allie and Fiona were nowhere to be seen when he diffidently stuck his head into Room Four to collect his discarded clothing. Then he headed off to Maude's office, to hear all about how he screwed things up...
Instead, the AI announced, "You have fulfilled expectation, Gary Oberndorfer. While the approach was unusual, the results were optimal - the student was extremely pleased and came away from the lesson with increased confidence."
Gary shrugged, embarrassed. "I went with my instincts. It wasn't the way I planned it and I wouldn't handle things that way normally, but she had certain needs..."
"You have good instincts," Maude congratulated him. "When you penetrated her, I thought I was going to have a heart attack - and then I realized she was having an orgasm! Amazing!"
"She was ... very needy," Gary muttered. "She would wander if you coddled her - you had to rein her in. If you didn't let her feel sorry for herself, things went well. Pleasure isn't something she gets a lot of..."
"Given an opportunity, she took maximum advantage of it," the AI summarized.
"You didn't get in much in the way of cunnilingus," Maude noted. "She'll be ready for fellatio in an hour or so - will you?"
"Yeah, I think so - I've got another charge in me."
"Good. For now, Fiona has her in hand," Maude murmured. "You can nap in Room Four if you like." She flicked a switch and Fiona and Allie could be seen on the screen. Allie was still nude; Fiona was talking to her while brushing out her hair. "Fiona may be present to supervise. By the way, Emily had nothing but praise for Chuck's efforts - and having seen the reports, I agree with her. He's ahead of the curve already."
Gary didn't know what to say, so he limited himself to, "Thanks," and went back to Room Four and collapsed on the only mildly mussed bed.
When he awoke, it was because the lights had come up. Allie was there, with Fiona. She was still nude, but apparently a lot more comfortable about it. Her hair looked clean and glossy, and Gary thought he detected subtle make-up - certainly she didn't look as pink and oily as before and there were no obvious blemishes in the works on her face. Her pubic bush wasn't, anymore - she had a nicely defined patch of hair there, not a wilderness. Even her stance was a bit different - less rooted and clumsy. "I'm ba-ack..." she said softly.
Libbie
- 24.03.2021
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