MOM'S FRIEND [PREVIEW]

MOM’S FRIEND

Young Man Feminized by His Mom’s Friend

Clover Cox

CHAPTER 1

Jake knocked on Winona’s door, eager for another morning session with his mom’s friend. He was her personal trainer, and she had quickly become one of his best clients. Jake hoped to find more clients, but it was a lot of work getting people to sign up for his services, let alone to find people who would pay him week after week, but at least he had Winona in his life.

Winona was someone he’d known for years, seeing as she was his mother’s friend, but their relationship had taken on a new light ever since she’d become his client a few months ago. She’d lost over fifteen pounds and gained a level of confidence that was seductive to say the least. Now she smiled wherever she went, wore tighter clothes, and seemed happier than she did when she first became Jake’s client.

“There you are,” Winona said brightly as she opened the door, flashing another one of those warm smiles of hers. “I can’t wait to see what you’ll do with me today!”

“Lots of squats and push-ups.”

“No, not push-ups! You know how much I hate those!”

“Show me your guns,” Jake demanded.

Winona sighed and held up her arm to flex it, laughing when Jake patted her muscles and told her that this was what she was working for, that this was why she sweat bullets every time he came over to her house.

“You’re right! I know you’re right! Let’s get to work.”

Jake nodded and followed Winona into her house. They went straight to her backyard, which was where they normally worked out when the weather permitted. She had her mats out and everything else ready that they would need for their exercise session, so Jake put on some music and got to work right away.

“Stretching is so important before you do any exercise,” Jake said to Winona as he stood behind her and held her arms, moving them left and right. Up and down. He tried to swallow his desire, but to say that an attraction had been forming between them would be an understatement. They’d been close to fucking on more than one occasion, and to make matters worse, Winona now knew Jake’s secret.

She caught a glimpse of his lacy white thong when they were working out one day, and she hadn’t stopped teasing him since. She promised that she didn’t really care, but Jake had been terribly embarrassed. He wouldn’t even have been wearing the thong if he hadn’t been running late. He usually had time to change into a pair of briefs before he met with clients, but he had an impossible list of errands to run that day and just never got around to taking off his thong, much to his current detriment. They never got through a session without her bringing up the fact that Jake liked to wear women’s undergarments, but when it came down to it, he didn’t really care. Nothing compared to the feeling of a tight lacy thong against his naughty bits.

“How’s this?” Winona asked as she bent down to touch her ankles in front of Jake, pushing her bottom up against his crotch, moaning a little as she felt the plumpness beneath his shorts. “Am I doing it right?”

“Perfect,” he said in a strained voice as he tried to control his erection from growing stiffer, but honestly, what was the point when Winona had such a juicy booty? One he dreamed about when he closed his eyes at night. One he envisioned fucking when he touched himself.

“Are you sure?” she asked and pushed her butt a bit more firmly against Jake’s cock. “I can go lower if that’s better.”

Jake cursed under his breath as Winona wrapped her hands around her ankles and kept moving her head toward the ground, showing off how flexible she’d become since they started working together.

“Right there is perfect. Now start working your way back up.”

“Okay,” she said in a breath as she slowly pulled her body to a standing position, turning around to face Jake. She stared into his pretty brown eyes, an undeniable attraction bubbling between them.

Jake moved away from Winona before he lost control of his willpower, instructing her to do a few lunges across the yard now that she was stretched and ready for exercise. She pouted at him but did as he’d asked, doing lunges across the yard with her hands on her hips.

“Am I doing it right?”

“Perfect!”

“How many times?”

“Go back and forth five times. Then we’ll move on to push-ups.”

“No, not push-ups!” Winona smirked to herself as she continued doing lunges across the yard. She’d felt Jake’s stiff cock against her bottom and desperately wanted to play with it, but there was the fact that he also liked to wear women’s lingerie. She wasn’t quite sure what to do about that but had decided to embrace the idea and had a little present to give Jake once they were finished with today’s session.

“How do you feel?”

“Great! I still don’t want to do push-ups, though.”

“Let’s start with ten and go from there.”

Winona groaned as she dropped to the ground to do her push-ups, which she honestly didn’t mind that much, but she loved complaining to Jake. She loved the way his face looked when she groaned, and what was so wrong with being a little difficult? Jake always cheered her on once she got started, and there was nothing she loved more than the sound of his encouraging voice.

“Go for ten more!” he hollered once she’d gotten to ten push-ups. “You can do it!”

Beads of sweat were falling from Winona’s face, but she pushed through until she got to thirty push-ups, her arm muscles burning when she finally collapsed to the ground.

“I think you set a new record!”

“Really?” she asked with a hand on her stomach, trying her best to catch her breath, but those thirty push-ups had zapped the energy from her body. “Because I can’t breathe.”

“Yes, you did great!”

“Does that mean we’re finished?”

“No! You still have to do squats.”

“Ugh,” Winona said as she picked herself up from the ground. “You’re never going to let me off the hook, are you?”

“Never!”

They laughed as Winona got into position to do squats, even though her arms and legs were already burning, but there was something about having a young man watching her that gave her the energy to push through and finish with her exercise routine.

“Now we just need to do a few more stretches, and then we can stop.”

“Thank goodness,” she said. “You kill me every time.”

“If I killed you, you wouldn’t be breathing.”

“Always so literal. You know what I mean!”

“I’m just messing with you,” Jake said and placed a light hand on Winona’s shoulder, their eyes meeting when he did. The look they shared was intense. Jake knew they wouldn’t be able to ignore this attraction they had for each other forever, but he was not at all prepared for what she did next.

“Let’s go inside. I fixed us some iced tea and homemade granola bars.”

“No sugar in the iced tea, I hope.”

“You know me better than that, Jake!”

“Just checking. Some of my clients have a terrible habit of loading up on sugar and carbs after a workout no matter how many times I tell them that they shouldn’t, but I should know that you’re better than that.”

“Exactly,” she said brightly and gently pushed on his shoulder. “So, what do you say? Can we head inside now?”

“After you,” he said and gestured toward her patio doors.

She walked ahead of Jake and opened the sliding doors, nervous to give him the present she’d bought, but it was about time that they stopped lying to each other about what they truly wanted. After Winona had seen Jake’s white thong, she couldn’t get it out of her mind, which led her to do a little digging online, and she was shocked when she discovered that plenty of straight men around the world liked to get in touch with their feminine sides, so she was more than a little excited to help Jake get in touch with his… if he was willing. She worried that he would reject her present, but she at least had to try.

“Here you go,” Winona said and passed Jake a glass of iced tea as she sat across from him with hers. She had his present hiding in the pantry and was working up the nerve to give it to him, trying to imagine all the different ways he might reject it, imagining a scenario where this present could ruin their relationship, but she had to try.

“These granola bars are delicious.”

“And healthy,” she said, glancing at her pantry, telling herself that this was the moment she had to act. “I actually got you a gift.”

“A gift? For me?”

Winona nodded. “Would you like it?”

“Yes, please!”

Jake waited excitedly as Winona grabbed his present from the pantry. She folded her lips as he slowly removed the wrapping paper. She had no idea how he would react, worried that everything would come to an end once he lifted the lid from the box, barely able to breathe as she waited for him to get there.

Jake didn’t know quite what to think when he opened the box and found a gray jersey dress along with a pair of black heeled ankle boots. It was an outfit he would love to wear, but could he actually admit that to Winona? It was enough that she knew about his thongs, but to wear this was crossing another line entirely.

“Do you hate it?” she asked.

“No,” he said quickly. “I just don’t know what to think.”

“What if we tried it on?”

“Try it on?”

“Yeah, why not? It’s perfect for a cool summer day.”

Jake stared down at the clothes in the open box, knowing that he wanted to wear them, he truly did, but he’d never gone further than lingerie out of fear that he wouldn’t be able to stop once he did, but maybe it would be better with a supportive woman by his side.

“Promise you won’t tell anyone?”

“Your secret is safe with me,” she said.

He stared down at the clothes for a few more moments before slowly lifting his eyes and nodding, not entirely prepared to walk down this feminine road, but what the hell. Why not?

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