[TG] If Wishes Were Kisses - Part 5 (Patreon)

Ben starts experimenting with more feminine clothing and makeup with Linda's assistance. 

~

Ben stepped into the cool, air conditioned hall. The floor was white, all around him were displays and shelves made of glossy black plastic and each surface was covered in makeup. He’d never cast more than a passing glance at the makeup section of the shopping centre before, let alone deliberately sought it out yet, here he was. He had been looking at Linda’s makeup table all week and developing a strange sort of envy. He didn't know who ‘Hope’ was yet but he did know one thing; she was beautiful and he liked it. Maybe he was vain but nobody had ever turned their head to look at plain old Ben, now he got subtle looks each time he left the house. Nothing lecherous, just the simple act of men and women alike noticing him. He was more than just part of the crowd now and he wasn't going to lie and say it wasn’t a major confidence boost.

From the outside, Makeup seemed like such a simple thing; a bunch of creams and pigments you smear on your skin, how hard could it be? He walked past rows and rows of items he’d never even heard of; bronzer, lip pencils, wing stamps; perhaps it was slightly more complicated than he originally realised. He decided to start easy; foundation. Something he had seen Linda apply a thousand times and yet even that was a mountain to scale; what tone, liquid or powder, what sort of brush? There was a glossy display poster talking about the importance of blending, whatever that was. Ben felt like he was drowning. Lacking any better idea he started holding his wrist out and dabbing testers on it until he found the right one. He then walked past the aforementioned bronzers and wondered if he needed them, or eyeliner? He started grabbing items at random if they sounded important. Lipstick was an obvious choice, but what colour. Red was the classic right? He held up a tube red so vibrant it almost blinded him.

“That’s called Victory Red.” A salesclerk said, appearing out of nowhere, “It was considered patriotic to wear it during the second world war.”

“Oh, that’s nice.” Ben replied awkwardly, was that a famous fact? Would it be strange for a woman his age not to know it?

Most little girls started playing with make up when they were children, somebody almost in their thirties should probably have at least a working knowledge of it. He didn't want to look like a fool.

“Do you think it would look nice on me?” He asked and the woman pursed her lips.

“You’d stop traffic.” She mused.

“Is that a good thing?”

The woman laughed, Ben couldn’t tell if she was laughing with him or at him, so he nervously giggled along.

“Perhaps, with that fiery hair it might be a bit much. How about we get you some muted pallets and pinks? Then some nice strong concealer to cover up those spots.”

Ben placed a hand on his cheek, eyes sliding to one of the many, many display mirrors. Were freckles bad? Now that she mentioned it, none of the models in the posters decorating the place had any, their skin was silken smooth. Had he been embarrassing himself all this time walking around showing them off? Why would Linda want a trait so unattractive? He just nodded, letting the woman apply half a dozen creams and powders to his skin at his own expense until he looked, in the woman’s words, ‘perfecto!

He looked in the mirror and felt his glossy pink lips twist up. He didn't feel attractive, that's for sure; the concealer was so thick in order to hide his spots that he feared one more movement might cause it to crack. The gloss on his lips so thick a single beam of sunlight caused them to almost glow. He thanked the woman and paid, walking out with two bags, one of his own random choices, another of the woman's. She did work at the shop, so she had to know what she was doing right?

~

It turns out no, she did not. The moment he walked in the door he watched Linda’s eyes widen and her lips purse into thin lines.

“Interesting look.” She said carefully, “Did you apply all that yourself?”

“No,” He sighed, explaining the woman at the store and how he had defaulted.

“Do you like it?” Linda asked after he was done, he thought for a moment and shook his head.

“I just wanted to look pretty.” he flushed, “I know that’s stupid, men don't want to look pretty but…I got a few compliments the last few days and-”

“Ben, you don't have to explain anything to me.” Linda giggled, “Everybody likes getting compliments. Everybody likes to know they look good, it doesn't make you any less of a man.”

“No, the lipstick does that.” he deadpanned.

“Actually, that’s lip gloss.”

“There’s a difference?”

Linda shook her head and took him by the wrist to the bathroom where she proceeded to clear the mess off his face. Ben sighed, feeling his pores open as they were exposed to the air once more.

“Those counter ladies just want you to feel bad about yourself so you’ll buy a bunch of crap you don’t need.” Linda explained, rummaging through both bags of his purchases. “Ah! Here we go.”

She took out a powdered compact and gently tapped a brush against the powder before gently brushing it across Ben’s cheek.

“Make up should be worn for you.” She continued, “so you can look how you want to.”

“I don't know how I want to look.” Ben admitted, Linda was leaning in close enough that he swore he could feel her body heat. Or perhaps that was just him blushing. “I just wanted to try something different, If I am going to be a woman why not embrace it, y’know?”

Linda hummed, putting down the contact and taking out the mascara, flicking it across his lashes.

“I can’t believe she made you cover your freckles.”

“They are a bit…ugly.” Ben looked away, “All splogy in some places and sparse in others.”

“Nonsense, it gives you character.”

“You're biased, perfect woman, remember?”

“So?” Linda put her hand on her hip and stopped for a moment, “Do you think I have bad taste?”

“No! Of course not!”

“Well then, there you go. By your own logic you must be beautiful. Freckles included.”

Ben blinked in shock and then giggled.

“Did you just bully me into feeling more confident?”

“Did it work?”

He thought for a moment.

“Kinda.”

They both laughed and Linda indicated for him to pout and stretch his lips as she carefully applied the liberty red lipstick. His chin was sitting in her hand and he couldn’t help but gaze up at her, dark hair framing the face he’d fallen in love with. Did he still love her? Could he after all that had happened? Love doesn’t die easily and despite everything, he felt a flush of warmth fill him watching her careful, focused expression.

“There.” She said quietly, releasing his chin, “What do you think?”

Ben turned to the mirror and gasped; gone was the stiff, overly smooth face the woman at the shop had given him. Instead now his skin was smooth but still showed those freckles across his nose and cheeks. His eyes were dark, lashes luscious and dark making his green eyes seem even more vibrant. Ben could understand now what the woman meant about stopping traffic, paired with his hair the bright red was certainly stunning but as his lips curved into a small smile he found he liked it.

“I look incredible.” He breathed.

“You know, I don't think I have ever heard you talk about yourself so positively without sarcasm before.”

Ben wanted to argue, he wasn't that much of a sad sack surely. But then he thought and realised she was right. He felt more confident and attractive in this moment than he had in years.

“I think…” He said slowly, “I think I’d like to go shopping again, try some more girly options.”

“Really?”

“Yeah, I mean, why not? What do I have to lose by having some fun?”

Linda squealed, throwing her arms around him in a happy hug before springing away awkwardly.

“Sorry!” She blushed, “I’m just having a lot of fun.”

Ben had to admit, he was as well. With a wry grin he put his feet up, resting them in Linda’s lap and stretched out.

“We may as well go all out, where’s the nail polish?”

It was late by the time they were done. Linda not only did his toenails but he even attempted to do hers, then both their fingers. After that it was hair, all the while they talked. Not about anything serious, just low steaks topics like tv and movies and the office drama Linda was watching from the sidelines. It was nice, homey; almost like the slumber parties from college films. By the time they were done they were both dolled up with nowhere to go but bed as the clock ticked past eleven.

“You can have the bed tonight.” Linda offered, “Then tomorrow we can both grumble while we try to wash lipstick out of the pillowcases.”

Ben bit his tongue; he didn't want to go to bed alone. After years of marriage a bed all to himself felt wrong and he didn't want to lose this warm, jovial atmosphere they had created.

“You can stay, if you like.” He whispered, “Not to do anything just…sleep.”

Linda looked conflicted for a moment before nodding. They undressed in silence, backs to one another; so much for retaining the warm atmosphere. Ben was still sleeping in his boxers with no shirt but somehow they felt…wrong, with Linda there in her nightgown. He grabbed an old shirt and threw it over the top, wincing a little as his breasts were squeezed. The discomfort might make sleeping more difficult but it was worth it just to have another person close by again.

As they slipped under the sheets Linda flicked off the light with a whispered ‘goodnight’ and they were left in dark silence. Ben could hear her breathing, feel the slight tingle of body warmth and rise of the sheets that told him another person was close by. Despite the awkwardness, it was comforting. Eventually though, tiredness won out over awkwardness and Ben’s eyes slipped closed. In that haze between sleep and wakefulness he swore he felt a pinkie finger intertwine with his own.

~

Something was tickling her nose. Linda sighed heavily, trying to push whatever it was away so she could go back to the lovely dream she had been having but it refused. Her dream melted away and the memory of it soon after, but the warmth and comfort stayed and she snuggled in deeper, hoping to doze in comfort just a little longer. Then her awareness began to return and Linda realised it wasn't pillows she was curled around but a soft, warm body. Her eyes snapped open and were met with a forest of red curls, likely what had woken her. Ben was asleep still, back pressed up against her chest. His make up had smudged in the night but somehow it made him look even more beautiful, the slight imperfections only adding to his natural, striking, beauty. Linda’s arm was around his middle and she was very aware of just how close her palm was to those lovely breasts. They were straining inside Ben’s shirt, desperate to be free and as Ben shifted slightly in his sleep she watched as the nipples hardened ever so slightly. A soft, tired sigh escaped his red lips and Linda had to bite her own. What was he dreaming of that was making his nipples harden? Was it that night in the study? The one she too dreamed of more nights than not? Ben’s lips parted and the tip of his pink tongue darted out to lick at them and Linda had to look away. Already her mind was filled with images of that tongue darting between her legs. She was sure it would feel exquisite and now that Ben knew what it felt like to be eaten out he was sure to be even better at it.

Unlike most men, Ben had always been eager to give her oral and more than once she had closed her eyes and imagined women in his place in order to come. Most of the time though, she didn't have to. Ben was talented when it came to eating her out and now that he was a woman, fuck, she knew she wouldn’t last long at all. Not that it was going to happen, she swiftly reminded herself, squeezing her thighs together as wetness began to form there. Once more she cursed Lucy Loving and her damn ironic potion; Ben had certainly got his wish. Linda had never been more attracted to him in her entire life.

It took so much restraint to uncurl herself from that soft body, she was so careful Ben didn’t even stir as she moved away. The temptation was there; Ben still loved her on some level she was sure. Waking up with her cuddling up next to him was sure to stir something in her husband but…she could not manipulate him like that. She had only just earned back his trust. Still…the need to release some of this pent up desire was necessary. Normally, she would just go to the shower and discreetly take care of herself but this morning, the computer was calling. That video was like a siren’s call; she was just about to open the door when a sleepy voice called out.

“You’re up early…”

She turned, Ben was looking at her with tired, sleep filled eyes. Her loins burned with want and she pushed it down.

“Yeah. Did you still want to go shopping?”

“Absolutely!”

Linda smiled tightly; a whole day of watching her sexy husband try on outfits, pose and strut his stuff. It sounded like absolute torture.

~

Ben eased his way into things; starting simply with slightly lower cut tops and shorter skirts. At first, feeling that breeze between his legs or knowing his tits were on display for all to see made him nervous. Once again that nervousness, the feeling of eyes on his back as if the sales clerk was somehow aware that he was actually a man, returned. But nobody laughed, in fact, more people gave him appreciative looks and his heart raced with excitement. He got more daring. Linda was a great help but he could sense her own discomfort; he knew her well, the way her cheeks flushed, her inability to look at him for more than a few seconds without getting flustered; she was getting turned on. Watching her perfect woman model in increasingly skimpy outfits was pushing her to her limits.

He should have felt bad, after all they had just managed to reignite their friendship but instead a wicked thought occurred and he began deliberately choosing more provocative numbers.

“What do you think of this one?” He asked innocently, posing with his chest thrust out in a green silk tank top and black skirt, “Does it make my butt look big?”

“Ye-I mean no, well, a little.” Linda choked out, “But in a good way.”

He turned, balancing on his tippy toes and pushing out his peachy ass.

“It’s not too short is it? Can you see my panties?”

“N-no…”

With his back to her Ben grinned; he had forgotten how much he loved teasing her.

“We almost have an entire wardrobe, think we could head home?”

‘So you can get yourself off? Not likely.’ Ben thought.

“One more thing, I want something for date nights.”

“D-date?”

“Yes, I figure I’d like to test this body out to its fullest. Looking like me I am sure somebody would be interested, don’t you”

She just nodded solemnly. She waited while he ran back into the shelves for one last nail in the coffin. He couldn’t be too obvious, he couldn’t go full lingerie but he knew there had to be a sexy outfit in here somewhere that would drive her wild. A flash of black and silver caught his eye and he pulled a rack from the shelves; a smooth, form fitting black dress, one size too small for him, it's only adornment a silver flower embodied at the hem. This was the sort of dress worn by women who needed no bells and whistles to be sexy; women like him. He bundled up the fabric and ran back to the changing room without letting Linda see.

He stripped off the tank top and skirt easily enough, revealing his bright red bra and panties. He’d bought them earlier, they were skimpy; the panties were basically a G-string made of red lace and the bra was similar with cups made of flimsy thin material and cups far too small. He’d grown to love such items; he liked being able to feel his hefty breasts bounce with no support and even more, he loved watching Linda try not to look.

He sucked in a breath and slipped on the strapless dress, it squeezed him tight, conforming to his hourglass figure so much the cleft of his ass was visible. He snapped it into place hugging his breasts, watching them jiggle as the elastic pressed them together. He turned a few times in the mirror; he was right about the dress being a size too small. The result was that the fabric had basically become a second skin; he felt like he was wearing nothing and looked about as close to naked as possible while still technically being decent. It took a full minute to wipe the smirk off his face before stepping out, a look of curious innocence on his face.

“Is this too small?” He pouted, “I feel a little…exposed.”

Linda’s eyes practically bugged out of her head. Her face going to red Ben was almost worried she would pass out. She cleared her throat a few times but no words came out.

“Linda? Are you okay?”

“Fine.” She croaked, “You look amazing.”

Ben felt arousal swirl in his lower stomach; it felt good, being so in control like this. For once he was the sexy one, the one being lusted after desperately. Their roles had been totally reversed and he knew now if he said ‘jump’ Linda would go ‘how high?’. He walked over to her slowly, watching her chest rise and fall with increasing speed as her breathing quickened.

“Tell me more.” He ordered quietly, “Tell me how sexy I look.”

“Oh God, so damn sexy.” Linda whimpered, reaching out a hand as if to touch him before hesitating. “I’m sorry Ben, I have been trying so hard but I…you just look so hot. Your hits being squeezed by that dress, your round ass, fuck.”

“Do you want to touch it?” He whispered, she nodded. “Beg.”

“Please.” There was no hesitation, “Please let me touch your ass.”

He grabbed her hand, reaching it behind him so that her palm pressed into one of his fat cheeks and both of them moaned. Linda’s hand immediately began to roam, brushing down the clear cleft in the dress as far as she could before returning and massaging the cheeks. Warmth and pleasure filled Ben’s whole body; it really had been too long. After so many years, knowing Linda was desperate to have him was such a turn on.

“Can I go under the s-skirt? Please, pretty please?”

“You may, just not the panties.”

Linda whimpered, slipping her hand under the short hem of the skirt and pressing her fingers into his warm skin. The panties barely covered any of his ass so she was free to squeeze and pinch the warm skin there. Each time she cupped the bottom of his ass, Ben felt his pussy throb. He knew Linda could feel it too, her delicate fingers were just inches away from his wanting hole, he could feel her temptation to slip them inside but he moved away before she could.

“Come on, there is something else I want to buy.”

~

For the rest of the afternoon Linda followed him like a dying man in search of water. She gripped his hand tight, occasionally copping a feel when he allowed it. The whole thing was one giant tease. He would pull her into an alley and allow her to touch him, running her fingers along his breasts and butt until he was so wet he was worried it might stain the dress. Then, just as Linda thought she was about to get a taste, he would make her stop and she always did. Each session went on slightly longer than the last and Ben knew she was eating out of the palm of his hand. When they reached the adult shop she was practically a gooey mess. She even moaned a little as he purchased the strap on, just like the one from the video.

“Do you want me to use that on you?” She asked as they left and Ben shook his head.

“I’m going to use it on you.”

~

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