Chapter 2 Building A Partnership

The next day, Thomas wakes up, feeling warm, fuzzy and a little dizzy. It takes him a few minutes to remember where he is, but he can feel the wool against his skin.

Did yesterday really happen? Thomas replays it in his mind: The dinner, the sex, the clothes, the warm embrace of Lisa's soft and wet pussy. He gets horny thinking about, his bulge is growing larger as his cock is getting harder.

Then he remembers her promise: They can do it every day. He smiles beneath his woollen hood at the though of it, just as he can hear Lisa waking up.

"Good morning, honey. Is my little woolie okay? We don't want to overdo this, let me get you of this."

She unbounds and undresses him. Thomas starts to shiver, and Lisa quickly puts a stop to it by tucking him inside a wool blanket with a red tartan pattern.

"I dreamt about you joining my business full-time, being my partner in everything. Doesn't that sound like a dream cum true, darling?"

"Yes, Lisa, it really does. When can we start?"

Lisa giggles.

"Oh, don't be so hasty, my friend. We need some breakfast first."

Over breakfast, Lisa tells him her plans. The business isn't going too well, but she is seeing brighter days ahead, if Thomas joins her. They need fresh money for the business to grow.

Thomas has never met him anyone like Lisa before. She is so full of ideas, of compassion, of spirit. And he has never been so much in love before.

"I have an idea. You have to say stop if you think this moves way too fast. But after yesterday, I think you are my soulmate. We two are as one. I'd like to move in with you and grow this business as much as we can. I thought I could sell my house to finance the expansion of the business."

Thomas waits for her answer as she chews with a quizzical look on her face. She is surely thinking about this. Finally, she is finished chewing, and opens her mouth.

"Are you sure, honey? Really? Do you want to be stuck with an old woman like me?

"Of course, Lisa. I'm dead sure. And you're not an old woman. You are the sexiest, most raucous woman I've ever met. We have something beautiful in common."

A smile widens in Lisa's face.

"Okay, my little woolie. That's so sweet of you. But I don't want to break up the nice rhythm we have established. Do whatever it takes during the days coming forward, but I want you to report back to here for dinner and fun every night."

And with that, a ferocious week started. Thomas has his days full with tidying, meetings with a real estate agent and getting rid of most of his stuff. There wasn't much spare room for his things at Lisa's house. Besides: The business was everything that mattered. Every night, he came over for supper and some frivolous, wolly fun. It was some of the best days of his life.

A week later, he hands over his keys to the new owners. They live in California, but want a second home in the North, where they can go skiing and relax when it gets too hot out West.

Thomas walks over and rings the doorbell. No one answers. He tries the door, which is unlocked. He walks in and puts down his only box on the floor.

He hears the clicking of heels approaching, and Lisa emerges in the hallway.

"Oh, there you are! So lovely to see you. You don't need to ring the bell anymore. After all: You're living here from now on."

Lisa is looking as sexy as he has ever seen her. She is wearing a long black ribbed turtleneck dress, which shows off her enormous breasts. It's obvious that she's not wearing a bra, as Thomas can see her perky nipples through the fabric.

A black leather belt with a golden buckle underneath really makes them pop out. Her feet is clad in smooth high-heeled leather boots, which underlines her dominating posture. She is wearing thick black wool mittens as well, giving him goosebumps at the thought of them touching him.

"To celebrate our new life, I want to a play a little game. You ready?"

Thomas nods.

"I can see that you're excited," Lisa says and points at his hard cock through his pants.

"First, I want you to completely undress."

Thomas takes off his clothes in a hurry and throws them on the floor.

"Very good. Now you can hand them to me, and wait here."

Lisa walks away with his clothes and returns a couple of minutes later. Thomas' cock is rock hard.

"We are going to play hide and seek. I'll give you five minutes to hide anywhere in this house while I sit and wait in the kitchen. If it takes more than five minutes for me to find you, you will be rewarded with a proper woolie handjob from these mittens. If I find you in less than that, I get to choose what happens next. Rules understood?"

"Yes, mistress," Thomas says with a giggle. He would really like that prize, but deep inside him he knows he wouldn't protest at the thought of her doing whatever she wants to him, as well.

"Okay. Starting now! I'll count loudly. 1.. 2.. 3"

Lisa walks into the kitchen as Thomas thinks about where to hide.

This is his chance to indulge in his fantasy like nothing he has ever done before. Thomas walks slowly up the stairs and into the bedroom as he can hear Lisa nearing the first minute.

There he sees an abundance of wool clothes. He settles on pink wool pantyhose and a thin merino turtleneck in the same colour as a baselayer. Then he puts on a long pink turtleneck sweater dress and two pairs of wool socks. He puts on two thick sweaters on top of the dress, before a hat, a scarf and thick mittens. He grabs a couple of blankets and throws them underneath the bed, where he lies down still and waits.

Then he hears Lisa shouting:

"Five minutes gone! I'm counting to five new minutes. If I haven't found you, you win!"

Thomas always reveals his position by answering her, but all he makes is a deep muffle as he realizes his near-mistake. Lisa takes three minutes downstairs, before she starts to climb the stairs. His heart is racing and his cock is throbbing in anticipation of his reward.

She's in the hallway when five minutes have gone. Thomas has won.

"You've won, sweetheart. Now, reveal yourself!"

Thomas gets out from under the bed and meets her in the hallway. She is smiling at the sight of him.

"I can see that you've really exploited the situation, my little woollie. Lie down on the bed, and you will get your reward."

Thomas smiles and lies down. He feels the thick mittens around his shaft, enjoying the sensational feeling. She starts slowly, caressing every inch of his cock. When she ups the tempo, Thomas starts to groan.

"Oh, you like this really good, don't you? Let's see how you react now."

Her hand goes fast as a blizzard in their home country. Nearing the edge she stops and starts again several times, inching him closer. When he finally comes, he explodes with cum all over the mittens, her dress and his clothing.

"What have you done?! I know you like it, but this wasn't part of my plan."

Thomas giggles. He loves the roleplay part of it.

"I'm so sorry, Lisa. I will make it up to you."

"Yes, you will, Woolie. We will make sure this doesn't happen again. You have gotten your reward, but I don't want you to spoil more of my clothes for the foreseeable future. I am sure you agree that we want this to be a thriving business, honey?"

"Yes, of course. I want it to succeed."

"That's good to hear. I see no other option than locking you up," she says as she takes out a tiny, little pink cage.

"This cage will make sure that you don't get a boner. And alas, you will not spoil anything on our valuable clothes.

She attaches it to his cock and locks it, hiding the key inside her dress.

"Don't worry, honey. Only you and I will know. And I will let it out when the time is fit. Sounds reasonable, doesn't it?"

It isn't, thinks Thomas, but he understands why. And knowing Lisa, he will be pleasured anyways. Either way, he has the wool on. And that's what matters the most.

"Great, my little sweetheart. Business before pleasure, you know."

Thomas nods in agreement.

"We have to start doing some proper work, now that you are satisfied. It's 2024 now, and we need a proper website to show all our items. I think there is a market for sexy women's clothing in wool, don't you agree? And for that, we need to show how a young woman can wear them in a sexy manner. But I'm not that young anymore, and I'm a bit shy in front of the camera. You would be the perfect model. Are you up for it, honey?"

Thomas hesitates. He agrees to the business plan, it sounds reasonable. But does it have to be him? He weighs the pros and cons. He doesn't want to look like a woman, he only wants to wear wool and satisfy his inner desires. But maybe this is the only way at the moment? She sure seems determined.

"Okay, then. As you wish. Anything for you, Lisa."

He breathes out. Maybe this is going to be quite nice?

"Oh, honey. I'm so glad you made that decision! I think this is going to take our business to the next level. You really are the cutest thing. I saw the hesitant look on your face, so to add a bit of spice, and in order to make this something else, I would like you call to me Mistress. That way, we make this a game, and not something you are dreading. Okay, woolie?"

"Yes, Mistress. This will be fun!"

He can instantly feel that he actually is looking forward to this. Dressing up is, after all, what he wants the most.

"We're going to have so much fun today. But we need to start with the basics, moulding you into a sexy woman."

The next hour, Lisa gives him the proper womanly treatment. He gets to take a long, hot shower where he shaves off all his body hair. Then she applies make-up and polish to his finger nails and toes.

She also puts on him gigantic fake breasts. After all, they want to sell the aura of big juggs with her clothes. He gets a wig as well, and when he looks at himself in the mirror, he gasps. This woman sure is hot. He can't believe that this actually is him. He feels his cock wiggle a little bit in its cage as a response to the sights.

"You look gorgeous, honey. Are you happy with your Mistress?"

"Very much, Mistress. I look hot, don't I?"

"You sure do, honey. Now it's time for the clothes."

In the bedroom, she picks out a sweater dress and high heeled boots for him. But she also gives him panties and a bra.

Thomas holds them in his hands, feeling the soft, lacy texture. This is the final line of resistance.

"Now, come on. Don't be so shy, honey. Without them, no wool for you."

He wiggles into the pink panties, which now hides his little cage thoroughly. You can't even see that there is something there. He gets help with the bra, which fits his fake boobs perfectly. So this is what it feels like being a woman, Thomas thinks.

He puts on the dress and the boots. He puts on the dress and his boots. His outfit is now complete.

"Very good, my little woolie. You look terrific. These photos will give us a nice bump in our sales."

The rest of the day, Thomas poses with tens of different outfits. They start to feel like a part of him now, and when Lisa finally is finished, he doesn't want to take it off.

Seeing himself in the mirror, he sees a sexy, big-titted woman with a pink turtleneck sweater dress, fastened with a pink belt with a large golden buckle. He sees dark pantyhose and high-heeled black leather boots. He sees flowing blonde hair, pink pouty lips and rosy cheeks. He sees white wool mittens, a thick white chunky scarf and a ribbed pink beanie.

He sees perfection. And he feels comfortable. He feels sexy.

"Can I... Can I... please keep it on, Mistress?"

"I've waited for that question, Woolie. And of course you can keep it on. You really look good in it. You need to take off your boots, but other than that, you can keep the outfit on. Now, go to bed while I upload these pictures. I can't wait to see what tomorrow brings. Sleep tight, my girly woolie. You will never dream as well as tonight."