Dressing Up Night Pt. 02

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After breakfast, Sam goes shopping for more clothes.
1.4k words
4.33
25.4k
17

Part 2 of the 4 part series

Updated 06/07/2023
Created 02/16/2015
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Sam woke up the next morning still enclosed in the cool satin and began to harden at his memories of the previous night. He realized he didn't actually know the barmaid's name, but then spotted a note on the table to the side of the bed. He picked it up and opened it.

'Samantha Honey, I brought you some more things but didn't want to disturb your sleep, you'll find them in the bathroom. I'll be cleaning your room, so feel free to leave things out. Kat x'

Sam sat up and saw the wig on the writing desk under the mirror. He walked over and tried it back on, looking at himself in the mirror. He was still wearing the now smudged bright red lipstick, and biting his lip in an attempt at a coy look realized he could still taste Kat on his lips.

Looking at the time he decide to go clean himself up before breakfast. At the top of his new pile of things were some makeup wipes and nail polish remover and so he set about cleaning off before slipping out of the teddy and into the shower.

Grabbing the first towel from stack to dry himself off he was surprised to find some Talc and a pair of black, lacy panties. He rubbed the talc into his body and found his nipples hardening as he felt how soft and smooth it made his skin. He stood in front of the full length mirror and stepped into the panties pulling them up over his stiffing member. After admiring himself for slightly longer he grabbed some pants and a shirt and headed down for breakfast.

Downstairs the bar was empty other than Kat and the other barmaid working the breakfast shift. They giggled as he walked in and Kat showed him to a table at the far end of the room. She came back a few minutes later to take his order, unbuttoning the top of her blouse as she approached, and sat down opposite him.

Kat leaned forward over the table and Sam's eyes were drawn to the pedant dangling between her breasts.

"She doesn't know," Kat said, "I just told here you were hot and I was going to flirt with you. Would you like a coffee?"

"Uh, yes please."

"Cooked or continental?"

"Cooked"

"Are you wearing them now?"

Sam glanced towards the bar.

"Act normal Samantha and she'll never know. Are you wearing the lacy panties?"

"Yes."

"How do they make you feel?"

"Sexy."

"Did you wank off in the shower?"

Sam hesitated. "No."

"Why not?"

"It wouldn't be lady like."

Kat laughed, leaned in closer and whispered.

"I fucked myself with my fingers in the shower this morning. I imagined it was your hand. Do you wish it was?"

Sam was taken back by how direct she was being. Kat just started fiddling with a strand of her hair.

"Yes."

"How would you like your eggs?"

Sam was thrown again.

"Sunny side up."

"Are you going to wear those panties to your conference?"

"Yes"

"Good girl. I'll be back with your food."

After she left the other barmaid kept stealing glances at him and smiling. Kat brought his food back ten minutes later.

"I'm working a late tonight. I'm going to take you clothes shopping this afternoon. Meet me outside at five and bring the wig."

The conference was a tedious as he expected and so at five he was stood outside the pub and hopped straight into the car as Kat pulled up.

"Hi Honey", Kat said in a sing-song voice as he got in, "did you have a nice day?"

"The worst. I knew this conference was going to be hard work, but I didn't think that was going to be in trying to stay awake."

Kat giggle, leaned over and gave him a kiss on the cheek. "I hope you have a better evening Sugar. Are you nervous?"

"Slightly. I don't feel very feminine, people might stare."

"Don't worry Honey. That friend of mine I told you about. She runs a very discrete shop, and is opening up late just for us."

Discrete was an understatement. The shop had no obvious advertising and was a run down building in the middle of no-where. Kat helped Samantha put on the wig and then took her hand as they walked to the shop.

"Relax Honey, just have a good time."

Inside was Danielle and Samantha found it hard to see her as anything but, with long hair and a cutting figure.

"This is my new friend Samantha. She's still a bit shy. We want something I can take her out in that doesn't look so masculine."

"Let's see what we've got to work with. Strip please Samantha".

Samantha's eyes went wide in fright and she looked towards Kat. "It's okay Honey, she's see it all before."

Samantha stripped down to her panties and Danielle looked her over in approval.

"Nice legs. I see a ring. Does her partner know?"

"Her wife doesn't, needs to stay that way."

"Okay, so need to hide the legs. What about something tight. Leather or rubber?"

"Leather, best she doesn't get a rash or friction burns."

Danielle walked off and came back with some black leather pants, a matching jacket and a tight white top. Samantha pulled them on and, after seeing the approving look from Kat, looked at herself in the mirror. Turning to look at her ass she couldn't believe the difference.

"A winner," said Kat, "and first attempt. I knew you wouldn't let me down. Now I also want something a lot more girly, for the bedroom."

Danielle went off and brought back another pile. "Strip and shut your eyes, I want this one to be a surprise," ordered Kat.

Samantha did as she was told.

"Step."

Samantha lifted each leg in turn and then felt something lacy and tight pulled up her body.

"And again, one at a time."

This time Samantha recognized the feel of stockings as they were pulled up her leg and fasted at the top.

"Arms."

Samantha felt some long gloves pulled up each

"Ready?"

"No panties?" Samantha queried.

"No. This is your slut outfit. I want easy access to you."

Her eyes still closed, Samantha felt the unladylike stirring.

"I know you like the smooth feeling between your legs, but this is for me."

Kat kissed the back of her neck and Samantha whimpered.

"Open your eyes."

Samantha did so to see she was wearing the most beautiful lacy ivory basque, with shear ivory stockings and matching elbow length gloves.

"Do you like it?" Kat whispered into her ears before giving it a playful bite.

Samantha hardened some more at the feel of Kat's warm breath, and gave out a small sigh.

Kat reached wearing an ivory silk glove and took hold of Samantha's growing embarrassment.

"It's okay Sugar, I know you can't help yourself," she whispered as she started stroking up and down, "just let yourself go."

Samantha looked in the mirror, not at herself, but at Kat's hand upon her. She found her breath quickening as the tension built up inside her. Kat reach round and grabbed her nipple through the lace.

"You can return the favor later Sugar," Kat whispered, "now just let go you slut, I want to feel you shudder and go weak."

With that Samantha couldn't hold back and several shots of thick ivory cum shot out and hit the mirror, with the last few pumps dribbling over Kat's glove.

Kat pulled her around. "Was that good my little slut?" Samantha nodded as Kat lifted the glove to her mouth and licked them off. "Mmmmm, I thought you'd taste good."

Kat pulled her close for a kiss, sliding her tongue into Samantha's mouth. "Now be a good slut and put Sam's clothes back on. I need to get to work."

Once Sam was dressed Danielle came back into the room and caught sight of the ivory streams running down the mirror.

"Did the job then Kat," she stated. "I thought you'd like it. On the house love," she said nodding towards the security camera high up on the wall, "I do like a good show."

With that they left and Kat drove back to the pub.

"I'm got a late shift Sugar and need to get away, so can't see you later. We'll have to see what happens tomorrow..."

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2 Comments
DaveXX80DaveXX80about 9 years ago
Yes!

So many feelings from reading....and so erotic! I want to be Sam! A dream fantasy! Looking forward to the next installment (please?!).

AnonymousAnonymousabout 9 years ago
Fantastic 2nd chapter

Please continue. I can't wait to read what happens next. I must tell you that I can really relate to this story because just like Sam/Samantha I cross-dress but my wife doesn't know. One day I might tell her but for now I would love to find a female friend like Kat to help me bring out the inner woman in me. I truly want to go out in public and I can't wait for that to happen. Please continue with the next few chapters.

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