Cross-Dresser - Awakening Pt. 09

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Gerry is transformed and Samantha takes another from Penny.
1.9k words
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Part 9 of the 10 part series

Updated 06/11/2023
Created 07/18/2022
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Samantha arrived at work, as she strode across the car park she heard her name being called, she turned towards the familiar voice. 'WOW what have you two been up to?' Ginger tried to look innocent. 'As if I didn't know.'

Alice blushed as Ginger stroked her ass through very tight denim.

Samantha caught up to them 'MMMmmmm, I love the transformation'.

Alice was in tight boot cut jeans, satin blouse and low heels while Ginger was almost unrecognizable. Her prim and proper office suit was replaced with a low cut basque with fishnet covering the top of her ample breasts, a tight leather skirt caressing her ass with stockings and insanely high spiked pumps. 'Do you approve Mistress?'

Samantha looked at her from every angle 'Very much' and kissed the pair of them.

Samantha took Ginger aside and whispered in her ear, she gasped at the proposal and grinned, 'I'll be there Mistress.'

Samantha let them go and watched as they held each other close, clearly Alice hadn't been home for a few nights. Samantha looked around 'Now where the hell is he?'

A red sports car sped towards her, turning at the last second into a convenient space. Gerry emerged, 'Frighten you sweet pants?'

'Sweet pants' thought Samantha in disgust, 'Just you wait.'

'Hi Gerry' she ran to him and kissed his cheek.

'Well I didn't expect that' he declared.

Samantha played all girly, 'Well I could see you have been missing Susie and I wondered, well if I could do anything for you?' She stroked his swelling crotch..

Gerry looked embarrassed, 'Not here you can't, we'll meet after work.'

'Sure honey, I know of a quiet place' a helpful Samantha suggested.

Gerry went inside followed by Samantha. It was a different Gerry at work that day, no sexist remarks and keeping his distance from Samantha. He wanted her so badly and feared he would fuck her across his desk if she came too near. It was the quietest day at work Samantha had ever had and she smiled as the clock struck five. On her way out she saw Ginger, who smiled and winked.

Samantha waited for Gerry and they took her car. It didn't take long for Gerry's sexual frustrations to start boiling over, his hands were everywhere, Samantha moaned as he stroked her exposed thigh, he obviously knew his way round a trans.. Thankfully they soon arrived at Samantha's hideaway but as soon as she was out of the car Gerry's vice like grip grabbed her ass, she just smiled and ran her finger down his cheek.

Once inside they went straight upstairs, it was a small flat and she took him straight to the bedroom where he pushed her onto the bed and started to strip.

Hanging around the room were various fem outfits, 'Hope your not expecting me in one of those' Gerry taunted.

'Not yet slut' thought Samantha, 'Not yet.'

Gerry climbed onto the bed and lay back, Samantha meanwhile stood before him slowly taking off her top and letting her mini shirt drop to the floor. She was wearing matching red bra and panties, red holdup stockings and high heeled sandals. 'Would you like anything else removing honey?' she purred.

Gerry's cock was now rock hard, he grabbed Samantha's wrist and pulled her next to him. There was no tenderness and certainly no foreplay he merely pulled Samantha's panties to one side and tried to force his cock inside. Samantha wriggled so all he got was the torment of her pussy rubbing against his tip.

Gerry was frantic he wanted to fuck her so much 'Hey slow down baby, wouldn't you like this first?' Samantha spun round and slid his monster cock between her soft lips.

He cried out with happiness. 'Mmmmmm that's better.,' Gerry arched his back as Samantha ran her teeth around his shaft and worked her tongue over every inch, lapping at his hot cum hole. Gerry's eyes closed and relaxed.

'AAAAAIIIIeieieeeee' Samantha screamed as he pulled her hair, his cock slipping from her mouth.

'So little girl likes to play games does she?' Gerry was on his knees holding Samantha firmly while he wanked near her mouth. Samantha willingly opened her lips and placed her tongue under the purple head, Gerry panted as his hand rubbed faster. She tried to grab his balls but he was too strong, 'Later bitch, first you gotta taste this.'

His shaft pumped and he fired his load of thick, white cum. First it struck her cheek, the next pump hit her tongue, she tried to swallow but as her mouth opened more thick juice filled it and covered her face. Gerry finished by milking the last drop of his load and wiping it onto her tongue. He then used his tip to push cum from Samantha's lips into her mouth.

Samantha was gagging, she hadn't expected Gerry's load to be so fruitful and was thankful when she saw the door slowly open.

'Why Mr Henderson I'd never have guessed.'

Ginger stood in the doorway, wearing a tight, shiny, figure hugging black corset and between her legs hung a huge strap on. Gerry looked shocked but couldn't take his eyes from her, 'Oh don't get up Gerry, I've been hoping you would try and plug this little bitch.'

Seductively Ginger approached, Samantha cried out as Ginger slapped her ass. 'Do you fancy a Samantha sandwich?' cooed Ginger. Gerry smiled as Ginger forced her victim onto all fours. 'Now suck him off.' Samantha shook her head, 'I said suck him off' ramming the the huge strap on into Samantha's pussy.

Samantha screamed then obeyed, her lips engulfed Gerry's cock.

Ginger was riding her hard and Gerry was getting more and more aroused. 'That's better isn't it Samantha?.'

There was a meek 'yes' and slow nod.

Gerry, getting more and more excited, inquired, 'Will you pump me Ginger?.'

Ginger looked at him in disgust, 'Don't be foolish can't you see I only peg Gurls' and gave Samantha an extra hard thrust causing her to bite on his hot shaft, Gerry flinched.

Samantha didn't know how much of Ginger's expert fucking she could take but it was having the desired affect on Gerry. Slowly Samantha curled her fingers around his sacs and twisted, softly at first then growing in intensity until Gerry's head went back and his eyes closed tight, 'OOOOOHHhhhhh YYYYEESSSSSSSS'

He bucked his hips but Samantha's grip just tightened. Gerry was helpless, between being sucked off and the pain being caused by Samantha, he just couldn't get the thought of Ginger pegging him out of his mind.

Samantha couldn't hold out any more, her pussy grasped Ginger's weapon as she was hit by a massive orgasm. She shook and bucked as wave after wave was transferred from pussy to mouth and Gerry's cock was punished further.

'AAAAARRRRGGGHHHhh, let me cum you whore' Gerry struggled but Samantha's grip was firm, she let his cock slide from her lips leaving it pumping helplessly in the air.

'But Gerry' she gasped 'Let Ginger dress you, it will turn me on so much'.

He slowly shook his head, by now Ginger had sidled up behind him and began rubbing and twisting his nipples 'Please Gerry, you know you want to really' as she licked his ear.

By now Gerry was out of control, he so wanted to cum and so wanted to be fucked by Ginger 'Yes Yes Yes anything I'll do anything' Gerry whimpered as he sagged. Gently Samantha released her grip, being careful not to let him cum

Samantha winked at Ginger, he was theirs. 'Now take your pick'.

Gerry looked at the outfits, choosing a pair of mesh panties and tight mesh top. They dressed him, adding nylons and heels to his look. Samantha whispered in Ginger's ear, 'Well done baby, but where did you learn to fuck like that?'

'Well I had all weekend to practice on Alice didn't I' Samantha's eyes grew wide, 'Oh yes this slut has her own slut, if you don't mind Mistress?' Samantha smiled and kissed her.

When Gerry was ready he was paraded in front of the mirror, he licked his lips at the tight panties as they caressed his cock and ran his hands over his sexy feeling legs, 'I I I never thought it would be like this' he stammered, Samantha lay on the bed, Gerry was on all fours above her. Samantha held her clitty erect and stroked Gerry's sacs through the mesh, he moaned softly and took clitty orally for the first time, letting his tongue flick gently then pushing it down Samantha's cum hole

Samantha purred 'Mmmmm that's it slut, enjoy'.

Ginger parted Gerry's ass and slowly lubed around his man pussy, there was a squeal of delight as more lube was slipped inside and his pussy was stretched wider, 'OOOOOHHHHHhh'. Ginger knelt and grabbed his hips, slowly, oh so slowly she took his anal virginity.

Ginger began slowly at first until his pussy could fully take her tranny tamer.

Samantha could feel his hot breath as he took the thrusts. She ran her nails over Gerry's wet flesh, more moans of pleasure.

'Your liking this, aren't you?' asked Samantha, 'Just think it could be like this every day', Gerry sucked harder and gripped harder onto the latex monster 'You'd like that, wouldn't you?' Gerry nodded and tensed, his first pussy climax was near.

'Of course we could stop'

Samantha let her clitty slide from Gerry's lips, a mumbled 'No NO please no' as he continued to lapped and suck.

'AAARRRGGHHHHhh OMG' Ginger forced her way in fully as she too sensed Gerry was near, very near.

His clitty dripped cum as his mind was filled with the thought of being fucked. His pussy was on fire as he climaxed and gripped onto the hard latex, but he didn't care, Samantha thrust her hips high and gave Gerry her load. His body was no longer under his control as he fell onto Samantha the dildo finally easing from his love hole. 'That was fantastic why did I resist dressing fem for so long, I must tell Penny.'

At this Samantha turned on him, 'You'll do no such thing slut, not if you want to be fucked like this ever again' he looked shocked.

'But she's been trying for years to make me fem' whined Gerry

'Exactly, years' snapped Samantha 'And where's her form of seduction got her'

'No where' Gerry admitted..

Samantha twirled her finger through Gerry's hair, he melted. 'Your mine now, mine and Ginger's, understand' Gerry nodded, 'Your now Gerri and you only have a clitty and pussy' Ginger stroked both, Gerri sighed.

'Yes Mistress Samantha I understand.'

They all dressed, giving each other kisses and fondles until they were ready to leave. At the front door Samantha called out, 'Get all that Louise honey?'.

Another door opened and Louise stood there holding a DVD disc, 'Everything recorded, I must say babe I got quite hot myself watching you three at play,' Samantha smiled and blew her a kiss.

Samantha drove Gerri back, 'What was she talking about Mistress?'

Samantha smiled, 'Just a bit of insurance in case you resisted. A copy of that disc would have reached your friends and family by tomorrow, sorry sweetie but we need you.'

Gerri sighed, 'Well you've got me now.'

Samantha let Gerri out and looked at the passenger seat. There for all to see was a very wet circle, she laughed 'Gerri really did love her first pussy orgasm.'

Out came the list, another X, this time by GH.

'Only one to go' thought Samantha but hadn't a clue how to find the elusive Joanna.

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