Anna's Transformation Ch. 05

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Anna succumbs to Jack.
19.2k words
4.66
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Part 5 of the 9 part series

Updated 06/10/2023
Created 05/14/2021
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Wednesday - Day Five

Anna drifted in and out of sleep in the early hours, finally rousing when Andy said goodbye, kissed her and left for work. She yawned, and stretched out, noticing her toenails needed some attention.

She felt different this morning than any other morning. Her nipples were just a bit sore -- from Jack's attention. Her labia felt different -- from Jack's attention. "Seems to be a pattern here!" She giggled.

She thought about yesterday. 'Wow, started out going over to get some gift cards, ended up spending the day with him, ending up on the pool making out, him kissing and handling the girls, then taking off my bikini in front of him - and Tim, seeing his big cock, touching it, making him cum three times and him kissing my kitty! Never thought all that would happen. Sure glad it did. Oh, my, he made me feel so good, so feminine -- and seven orgasms! And we almost had sex -- he wanted to put that big huge pole inside my kitty -- god what would that have felt like?'

As she was sitting up her phone chimed with a text from Jack:

>good morning, beautiful!!!! 😊

She giggled and texted back:

>starting early with the flattery, I see!

>it's the truth!

>how do you know -- you haven't even seen me yet today?

>I don't have to see you to know that, neighbor girl!

>You are so bad, Mr. Mitchell!

>What time should I expect you for breakfast?

>Really? i thought you were kidding

>No! Just got back from the farmer's market with some good stuff!

'I should say no, it would be safer, but I want to be with him.'

>Ok, you convinced me -- 30 minutes?

>See you then!

By this time the Jack Effect had struck and her nipples were at full mast. She did her bathroom routine, finishing by combing her long, curly blonde tresses. She pondered what to wear. 'Do I want to encourage him, or cool him down a bit?' She spied the slingshot. "How does this contraption even work? Might was well try it on."

She stepped into it. Two straps ran straight down from her shoulders and barely covered each nipple. They converged to create a tiny panty, then one thin strap that ran under and between her butt cheeks and back up to where it split again below her shoulders. The single back strap went straight from her butt crack to her shoulders, not even touching her back.

"Jeeze, all this thing covers is my pussy and nipples -- and gives zero support for the girls!" Her aureoles were visible on both sides of each strap. It felt very sexy -- and dangerous. She tapped her finger against her lips a few times. 'Well, I was naked for the guy yesterday, so why not?'

She wrapped herself in the sarong, placed her phone and some other items in a small beach bag, slipped on her sandals and headed to Jack's.

*****

He was sitting at the table on the pool deck, sipping some orange juice, when he saw Anna turn the corner and start down the walkway. He wore loose shorts over his newly-purchased swimsuit, a crisp button-down shirt open down to the last 2 buttons and no shoes.

They smiled at each other. He stood as she approached. As always, his heart skipped when he first saw her. She set her bag down and he took her hands in his and kissed them both. She giggled. "I was right, you do look beautiful today! 'Good enough to eat!"

"Thank you, Jack, you look nice yourself." She looked him up and down. "God, I want to just eat this studly man right up!

He guided her to her seat, close by his. She watched him pick up a bright pink flower he had just cut and a hair clip. He looked at her.

"Do you mind?"

She cocked her head slightly. "Huh?"

He stepped behind her and pulled a lock of hair in front on each side back behind her head and secured them together with the clip. Then he gently placed the flower in her hair, just above her right ear, adjusting it just so. He sat down to admire his work.

Anna blushed -- never had a man paid any attention to her hair! "Didn't know you were a hairdresser, neighbor man."

"It's my feminine side coming out!"

She burst out laughing. "Trust me Jack, there's no feminine side to you -- I know for a fact that you're all male!"

"Oh well, can't blame a guy for trying!"

She touched his hand and batted her beautiful eyes at him. 'I desperately want to kiss this beautiful, sweet man.' "You are a sweet man, Jack Mitchell." and she pulled him close for a kiss. He touched her cheek and started to pursue with vigor.

She pulled away.

"Are you trying to seduce a girl before you feed her a promised meal?"

Jack grinned. "I'll plead the fifth!"

She touched a bruise visible on his shoulder, under his open shirt. "What's this?"

He grinned. "Last night I was bitten by the most beautiful woman in the world."

She blushed at Jack's compliment and that she had actually bit a man. 'That's a first for me.'

"Wow, Jack -- you set quite the breakfast table!" A chilled bottle of champagne nestled in an ice bucket. One plate held a selection of small cakes, while the other held at least a dozen varieties of fruit. A single red rose in a vase caught her eye. She looked at it and looked at Jack. No words were exchanged.

'I hope the rose wasn't a step to far, too fast.' A last-minute idea, he had clipped it from a bush up the street.

She thought, 'A rose is something a man gives his lover. Are we lovers? Will we be lovers? OMG.'

"Champagne?"

"Sure!"

He deftly poured 2 flutes and passed her one.

They tapped glasses and sipped, looking into each other's eyes and smiling. "I am totally and absolutely in love with this incredible woman -- I'll die if I can't have her. But am I just a fling for her? Oh, yea, and there's the small matter of her being married!'

'He's GOT to be the most attractive man in the world. God, I so want him. Will he want to have sex today? Will I let him put his big thing inside me?'

They chatted easily for a while, nibbling at the cakes and fruit and finishing most of the champagne. "You kissed my hand in the driveway - no man has ever done that. And you open the car door for me. And you put this flower in my hair. You are such a sweet man, Jack." She reached out and held his hands, giggled and blushed. "And such a naughty, naughty boy, too!"

"Can't help myself on either one. It comes natural with you,"

"So, I -- well we -- did some things yesterday that I'd never done before," she whispered.

"I'm hoping you enjoyed them -- It seemed like you did." His cock stiffened at the memories.

She nodded, and they looked into each other's eyes for a long minute. 'He has the most wonderful smile.'

"So, are you ready for a swim, pretty lady?"

"I believe I am, sir!"

"I sure love your sarong. But I am wondering which suit you picked."

"Really -- I can't imagine you'd be wondering about that. I decided to go with my old one that I wore Sunday."

Jack just started at her, unable to mask his disappointment.

She laughed. "Gotcha. No, I'm wearing something a nice man bought me yesterday. You may like it."

He grinned and they stood up. She started to undo the knot holding up her sarong, then stopped. "You first."

Jack undid two buttons and tossed his shirt on the chair. He watched her admire his chest.

"Nice." she whispered.

He slipped off his loose shorts to reveal his new suit. She stared, her mouth agape.

The front was basically a loose, stretchy, pale blue pouch holding Jack's well-endowed manhood. It hung from what was basically a string, circling low on his waist.

His large, semi-hard penis pushed out, curving down arounds his oversized balls. The pouch hoisted his package up, making it project out. Sort of like a bra for a man. He slowly turned around, showing her the G-string back -- his muscular ass fully on display.

"So, what do you think of my new purchase?"

She looked at his face briefly, them back down to his huge bulge. "Oh, Jack, wow. It doesn't leave much to a girl's imagination!" 'OMG -- I may faint!'

He reached out and lifted her chin with his index finger. "Hey, my face is up here!" he said, grinning.

She turned crimson red. He kissed her gently. "It's ok, I don't mind if it's you looking."

He started pulling her knot loose, slowly, as she looked into his eyes. 'I can't believe I'm letting him reveal me -- but it's so exciting! Those nipples feel ready to burst.' The knot gave way and he unwrapped her. He moved to put the sarong on his chair -- but instead just dropped it.

"Oh my god!" He whispered.

Two thin, electric green straps led from her bare shoulders out and down her huge, magnificent breasts. They widened to about 2 inches as they crossed her up thrust nipples, barely covering them. There was a half inch or so of gap between the taut strap and her upper breast. The straps continued downward, converging into a tiny panty that showed off her labia. The forward projection of her breasts created a gap between the straps and her tummy. She was all but naked. 'Look at him -- he's stunned!'

Jack was indeed stunned.

'This is soooo naughty!' She turned sideways, thrusting her breasts and bottom out, then turned and showed him her back. The suite was only a thin strap, appearing as if from nowhere out of her butt cleavage and running up to under her hair. She faced him again and looked at this crotch. His manhood was rapidly expanding, stretching out the swimsuit pouch obscenely.

"Well, it seems like part of you likes the suit you picked out!"

"Oh god yes! You -- you look incredible, Anna!"

She smiled. He was on the verge of attacking her when she grabbed her bag, took his hand and led him to the wide chaise lounge they'd been on last night. Her breasts and bottom bouncing and shaking, his engorged cock preceding him like the bow of a sailing ship.

She laid face down. "How about putting some suntan lotion on my back, Jack?"

"Glad to."

He sat next to her, opened the bottle, squirted some on his hands and started rubbing it onto her beautiful back, massaging it in. "Oh, you have great hands, Mr. Neighbor - that feels so good!"

Subscribing to an expansive definition of "back", Jack rubbed the sides of her breasts, most of which ballooned out to her sides.

"Oh, yes....." She moaned.

He added lotion, moving slowly to her lower back, then her butt cheeks. "Um, hey, mister, those aren't my back."

"Sorry, I must have gotten lost on my way to your legs." She giggled. 'God, this is incredible!'

He rubbed and caressed her upper thighs and bottom. She spread her legs slightly to allow him better access, and he took full advantage, rubbing her inner thighs and brushing up against her barely-covered pussy. This caused his cock to surge. He adjusted himself so that his erect shaft was pointing upwards instead of down. Fully hard, it stuck almost straight up, tenting the pouch way up and pulling it away from his waist.

"Oh, don't you dare stop that," she moaned, so he didn't, speeding up. "Oh god," she groaned, and her body tensed as she climaxed. "Oh god!" He slowed down and she came down from her orgasm.

He leaned over and whispered in her ear. "That's one...."

She giggled.

"...of twelve scheduled for this morning."

She opened her eyes. "Pretty bold prediction, big boy."

"Care to wager?"

"Loser makes lunch."

"Deal."

She rolled over, causing a breast to pop out from under its strap. "Ops! Wardrobe malfunct-" She giggled, then stopped short. She stared, stunned at the sight of his prodigious erection rearing up towards his navel, pulling the pouch tight against his ball sac, showing its impressive size. She reached out and caressed the pouch, first with one hand, then both. "Jesus, Jack."

He saw her breast, free of its constraint, its nipple engorged and hard, and lost control. She saw and felt his shaft pulse and shoot a load inside the pouch, then a second. She reached up and pulled the waistband up and off, freeing his missile, which she grabbed as it spewed forth it's third shot, which arced up about three feet before landing on Anna's arm and exposed breast. This erotic scene set off her own climax. "Oh god!"

The fourth shot followed the same trajectory, with the last one just oozing out onto her hands. They looked at each other, both panting. Jack pouch, which still held his balls, was a cummy mess. Anna was the first to speak, her heart rate through the roof, still panting. "That's one for you, and now two for me!"

"You had one too?"

She nodded. "A nice one." They laughed together.

"I'm a mess, Anna."

"So am it, thanks to you." She said scooping up some cum from her breast. She looked at her finger, looked at Jack, shrugged and licked it. "Yummy! We better get this messy suit off you." 'I want him naked.' She pulled it down and he kicked it aside, his big shaft bobbing right in front of her. He took her hand. "Let's clean off in the pool."

'I want to be naked with this man!' She peeled off her slingshot and jumped in after him. They were on each other in a second, her legs wrapped around his waist, his arms around her back, their mouths locked together. He slipped his still rock-hard erection between her legs and pushed up, lifting her with it.

The feel of his hot cock in her vaginal cleft, with no cloth between them, lifting her up, brought her to a short, sharp orgasm. Jack grabbed the closest breast, squeezed it and bit down lightly on its engorged nipple. She broke the kiss and screeched, loud and long as another orgasm rippled through her.

Her heart raced. She couldn't think, couldn't speak, couldn't move. He held her close, slowly rocking her on his hard cock, her head on his shoulder. "That's four for you, one for me."

She looked at him and smiled. "You're just amazing. I'm rather enjoying my special pool seat." She reached behind her and caressed the end of his cock as it slid out from under her beautiful bottom. "you have a big, beautiful, hard cock, Jack Mitchell -- I love it!" 'Is that really me saying something so naughty?' "So. I'm noticing a pattern, Jack, of us losing what little clothing we have on and ending up naked."

"Yes, I've noticed that too. We'll have to research the cause."

"You, Mr. Mitchell, are the cause of that!" She giggled.

They kissed, and fondled and caressed for a good half hour, occasionally whispering in each other's ear and laughing. Jack's cock lost none of its stiffness. 'God, I want this big thing inside me, it would feel so good, he's so big, so hard. Would it even fit? God, to feel it cum in me, oh my, I would cum so hard. He's been hard for so long. Will he try to just take me? What would I do?' "So, is it normal for a man to be hard for so long after climaxing? I thought it only lasted for a few minutes."

"Oh, yes, it's entirely normal if it's my cock and you're sitting on it!"

She grinned. "Ha- good answer. But you need to catch up on the scoreboard, big boy. Isn't this big thing ready to erupt again?"

"Yes, it is."

He lifted her up about ten inches by her butt cheeks, allowing his cock to rise up, pointing right at the gates of heaven. He gently lowered her until his head was nestled against her opening. She grabbed the sides of his head and, touching her nose to his. "Um, where do you think you're going with that big boy?" 'Oh, god, it's right there, nothing between us, it's so big, so hard, so hot, I'm so wet, he could just put it in, take me, take my sex. I want him inside me, need to feel this huge thing - but I'm married!'

'Going for broke here -- all or nothing.' "I want my next orgasm to happen deep inside of you. I want to make love to you in the worst way, Anna, I want us to be lovers."

She looked at him, tears welling up in her eyes. 'He wants me, wants my sex, wants to be inside me. I want him inside me. Oh god. What if he's just using me? What do I do? I'm married!' "Oh, baby I want it too, so bad. I'm so conflicted -- I'm married, and I don't want you to think I'm leading you on and my god what about Andy and oh, I'm just a mess!" She started sobbing against his shoulder.

He lifted her up a bit, slipped his cock out of her entrance and gently set her down on the pool bottom. He held her loosely and caressed her head until she calmed down some. He touched his nose to hers. "I would never want us to do anything that you don't want to do. I am so happy to have had these two days with you, I don't want to mess that up. I'll take whatever part of you you're able to give me, and I'll love every minute of it. I'm so sorry if I've upset you, Anna." He stopped short of saying what he really wanted to: 'I love you, Anna.'

She looked deep in his eyes for a good minute -- the longest minute of Jack Mitchell's life. 'Oh god, what he just said.' "Let's get out," she said, very quietly. They walked up the stairs, Jack ready for it all to come crashing down. Tears streamed from his eyes.

'What -- why is he crying?' "Baby, why are you sad?" She said, her eyes widening and her fingers tracing over his tear-covered cheeks. Suddenly, she figured it out, and placed her finger vertically against his lips. 'He has a heart -- a great big heart. I'm not just a female body -- he cares about me.' She whispered. "Don't say anything. There's no cause for tears." She paused and looked deeply into his eyes. 'Now I know the right choice. It's time. I want him inside me.'

"Take me to your bedroom and make me your lover, Jack Mitchell."

They kissed, sweetly and softly. "Oh, Anna," he whispered. He took her hand and led her to his bedroom. He stopped short, smiled at her, put her arms around his neck, reached behind her legs and easily picked her up. She giggled. "What are you doing?" "Oh, my god, girl, this must be what being swept off your feet means!"

He kissed her nose, brought her through the doorway and set her gently on his bed. He sat next to her and pulled her into his embrace. Their mouths locked, tongues dueling and probing. Their hands exploring, caressing, rubbing and squeezing, faster and faster.

She held and stroked his stiff manhood. He caressed her soft, moist labia. She broke the kiss and laid down with her head on his pillow. "Anna, you are the vision of beauty."

She smiled. "Flattery -- well, that's going to work this time."

She slowly spread her legs and pulled him between them, his heavy erection settling on her tummy, his chest against her mounded breasts. She reached down and caressed his throbbing cock. 'God, it's enormous, so hard, need it in me.' "Baby, you're re bigger than my husband -- way bigger. I don't know if it will fit in me -- please be gentle, Jack."

He kissed her. "I would never do anything to hurt you, baby. I'm going to get you ready." She gave him a 'huh?' look. He scooted back and began kissing the soft skin on the inside of her beautiful thighs.

"Oh god, oh Jack!" She began moaning and he moved closer and closer to her labia. The sweet smell of her musk made his nostrils flare and his cock pulse. She pulled her legs up, wrapping them around his neck. He applied his lips and tongue to her pussy which caused her to arch her back and cry out in passion. "Oh Jack!!"

He raised her temperature by inserting both his tongue and a finger into her warm, wet vagina, and that set her off like a bomb. She screamed as a sharp, intense orgasm struck, her body trembling, her legs locking around him, her hands unconsciously holding his head hard against her pussy. He prolonged it by curling his finger up, finding her g-spot, causing her to scream and buck again. After a minute he could sense it was time for her to come down, so her pulled his finger out and gently kissed her quivering pussy lips, now drenched in her wetness. She finally released her death grip on his head, still panting. He looked up to see her look back at him, her blue eyes glazed.