tagTransgender & CrossdressersDressing Up Night Pt. 03

Dressing Up Night Pt. 03


Sam woke early the next morning and lay there thinking about the previous evening. When they had got back Kat told him that she would take Samantha's clothes until the next day, to build his anticipation.

The conference was even worse than the day before, especially as he spent half the time wondering what Kat had planned for him that evening.

When he got back to his room he found Kat was already there and she had laid out an outfit for him in the bathroom. It was the leather pants and jacket from the night before, along with a silky thong and bra.

Sam stepped into the panties first, pulling them up and squirmed slightly at the new feeling of the thong running tight between the cheeks of his ass. Next was the bra and again another new feeling of the straps tight across his back and shoulders. Next he slipped on the wig.

Samanthat admired herself in the mirror and stroked her nipples through the fabric making them stiffen. She put the rest of the clothes on and realised that not only could she see the bra through the thin white cotton of the vest, but that it was slighly padded giving her more of a bust.

She went back out to Kat who smiled and told her to sit down for make-up. Kat began carefully applying all sors of make-up to Samantha's face, and then gave her nails a bright red coat. When Samantha looked in the mirror she couldn't believe how feminine she looked and felt.

"What are we doing this evening?" she asked Kat.

"Do you trust me? Really trust me?"

"I think so."

"Think isn't good enough. I want you to trust me, to do whatever I ask without hesitiation. can you do that for me."

Smanatha thought for a moment, and then let out a soft "Yes"

"Good girl. Take your wedding ring off, I'm taking you out to a quiet hotel bar I know. We'll just talk and work on your feminine side."

Kat took her by the hand and walked her out to a waiting taxi. They slid in the back and the driver pulled off. The driver tried to make conversation but as soon as Kat told him they were "on a first date" he quickly went silent.

Kat whispered into Samantha's ear.

"I want you to kiss me now, gently, I want you to be comfortable with me in public."

Samantha turned her head and leant in to kiss Kat. She was surprised by how soft Kat's lips were and pushed harder against her. Kat pulled away.

"Gentle I said."

Samanthat tried again, this time controling her urge and gently placing het lips on Kat's. This time Kat responded willingly, parting her lips and letting Samantha taste her mouth.

On reaching the hotel Kat pulled away and paid the driver. She again lead Samantha by the hand into a bar that, as promised, was nearly empty. Kat ordered them a couple of glasses of wine and they found a table out of the way in the corner.

"So you can kiss convincingly, but now we need to work on your voice, you're far to harsh and need to soften it up."

They talked for a while until Samantha's voice came naturally, but were interupted by the barman bringing over a bottle of wine "from Frank at the bar". Samantha looked over and her eyes widened slightly.

"What's wrong?" Kat asked.

"I know that man, his name isn't Frank, it's George, and he is attending the same confernece as Sam. He sells cars and he's married,"

"I need you to be calm, he won't recognise you,we should have some fun,"

Samanatha tried to object but before she had a chance Kat had beckoned him over.

He again introduced himself as Frank, and claimed to be in the area looking for property to add to his portfolio.

"and what are two fine ladies doing here alone?" Frank asked.

"We're not alone, we're with each other," Kat said, leaning in and kiss Samantha, "it's our first date and I'm trying her out."

"What do you mean?"

"Samantha here is my slut. She'll do whatever I tell her. If she's good enough I'll take her out again."

Samantha blushed, and panicked slightly as Frank looked at here in disbelief.

"Kiss him Slut", Kat ordered.

Samantha did as she was told, and leant over to kiss Frank. As she did so she smelt his excessive aftershave. She kissed him gentle on the cheek.

"Properly Slut"

Samantha reach up and gently turns his head, planting her lips on his.

"I know the truth about you Frank," Kat said, "you came in here hoping to pick up a one night stand and saw us, and now you're wondering if you're man enough to satisfy both of us."

"I've a room upstairs."

"One condition. I'm breaking my new Slut in, so you don't get to do anything to her unless I say you can."

Frank stood up and started walking back to the lobby. Samantha looked scared into Kat's eyes. "Trust me," Kat said, "I won't make you do anything you don't want to."

In the lift Kat told Frank he could feel Samantha's ass if he wanted, and so he reached over and gave it a squeeze.

"Nice and firm," Frank declared and Samantha blushed.

When they got to Frank's room, Kat put the TV on a music channel and told Samantha to start dancing.

"What do you want to do to her Frank?" she purred.

"I want to feel her against me."

"Why don't you then."

Frank walked up behind Samantha and pulled her against him. His hands reached up and squeezed her small pert breasts and Samantha could feel how hard he was against her ass.

"Slow down Frank, I'm not sure she's ready for you yet. Step back."

Frank did as he was told.

"Turn around Slut," Kat ordered.

Samantha dis as she was told and couldn't help notice the bulge in Frank's Pants.

"Get you your knees. Good slut. Now unzip Frank and let him out."

Samantha complied.

"What do you think Slut?"

"It's so big."

"Lean closer Slut. WSee how he is twitching in anticipation. What do you say to that?"

"Would you like me to suck it Frank?"

"Yes Bitch", Frank replied.

Samantha leaned closer and opened her mouth slightly, breathing out over Frank's hard rod. She looked up at him and saw his grin. She looked back down and opened her mouth more fully, leaning closer. She closed her eyes and licked her lips, her tongue narrowly missing his tip. She leaned closer.

A phone started ringing and she jumped back.

"That'll be your wife George," Kat stated matter-of-factly, "wondering whose mouth you were about to stick your dick into."

George panicked and grabbed the phone. Kat grabbed Samantha by the hand and dashed out the door. Samantha didn't know whether to laugh or be angry.

They jumped in a taxi and headed back to Samantha's room, Samantha now shaking and Kat holding her tight in back of the car. "Good girl," she whispered, "I said you'd be safe."

Once in Samantha's room, Kat gave her a bag with the other outfit in. "Go change," Kat told her, softer this time, and playfully added "Slut".

Samantha changed into the ivory basque and went back out to join Kat. Kat had moved a chair into the middle of the room and beckoned Samantha to sit in it. Once she had done so Kat began rubbing her shoulders and gently kissing her neck.

"Did you enjoy that?"

"I'm not sure."

"Would you have taken him into your mouth?"

"I didn't want to, but I wanted to please you."

"That isn't an answer."

"I don't know."

Kat moved around and sat on Samantha's lap, her breasts in front of Samantha's face.

"That still isn't an answer. Answer me Slut, would you have sucked him off for me?"


Kat leaned forward and kissed her before she could answer, one hand on the back of her head pulling her in, and the other hand down between her legs.

Samantha felt herself stiffening.

"You don't know what you want," Kat said, "your still confused, which is why I was pushing you, I want you to work out who you are and what you want."

Samantha just looked at her.

"I know what Frank wanted," Kat said, "this."

Kat slipped back and on to her knees infront of the chair. She slipped her mouth around the stiffness between Samantha's legs, and as she did so Samanatha tipped her head back and let out a sigh, the wig falling to the floor.

Sam began to feel his nipples under the lacy fabric, and reached down running his other hand in Kat's hair.

He felt his shaft harden further as Kat's lips surrounded it, her wet mouth lubricationing it as she slide it in and out of her.

Kat looked up at him, running her hands over his stockinged legs.

Sam found the combination of senses begin to overwhelm him, until he began to feel the tingling welling up inside him, his breath quickening even Kat was doing all the work, gentle moans passing from his lips.

Abruptly he could contain himself no more, and started releasing himself into her willing mouth. He shudder several more times until she finally pulled away from him.

"That's what Frank was after," she stated, "but I don't think you're ever going to give that to someone."

"Thank you," Sam panted.

"Sam, Samantha, someone else, it's your choice, I just want to help you work out who you are. Regardless, tomorrow we're going to a night club."

Report Story

bysimon_baker© 1 comments/ 15100 views/ 9 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartAngelSexy1, algolfcrazy and 7 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (1 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (1)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: