tagTransgender & CrossdressersDressing Up Night Pt. 04

Dressing Up Night Pt. 04


Sam awoke, still wearing Samantha's ivory basque and thought back to the night before and all his conflicting feelings and thoughts. He carefully stripped off and showered, realizing Kat hadn't helped remove any of the make-up. He felt disappointment as he did so, but knowing he had to be the perfectly groomed male before he could leave the room. At least Kat had left him the thong from the night before and he was feeling more comfortable with the way it pulled tight into him.

The conference was tedious as ever, although Sam noticed with some satisfaction that George, or "Frank", had left early. He counted of the hours and minutes until he could return back to his room. He returned to find Kat already waiting for him, wearing a tight and short silver dress.

"I've brought you some more clothes sugar," she purred, "I went back and asked Danielle for some thoughts on how to show off that figure of yours. Go get dressed and I'll do your make-up."

In the bathroom Sam found the new outfit. The first item was a black satin padded bra. He pulled it on and realized the padding gave him the appearance of having small, but wonderfully pert breasts. and he stood there just feeling and squeezing the material for a few moments.

Next was a full body stocking, which he stepped into and pulled up, as he did so he discovered it was crotchless allowing access between his legs. The stocking had a slightly lacy pattern to it, enough, he realized to mask his admittedly fine hair on his arms and legs. The feeling of being enclosed in something so pretty caused a slight stirring between his legs and he wondered how he'd control that aspect of himself.

The next item solved that a pair of control panties. Sam was initially disappointed that they didn't have the sexiness factor of the lacy thong and panties he'd previously worn in the week, but when he pulled them and saw the way they tamed his bulge, he realized they made his shape more flattering.

Finally there was a tight, and short, black dress. He pulled it over his head, and then pulled the zipper on the side until it was clinging tightly against him. Looking in the mirror, as he pulled the red wig onto his head, Samantha was amazed at how sexy she looked. The idea of ever going out in something so tight, or so short, would never have crossed her mind even just the day before.

Kat carefully applied lipstick and nail varnish, both a bright red, followed by a soft foundation and a mascara. Finally Kat produced a pair of red high-heeled shoes. Samantha stood in front of the full length mirror in her room and couldn't believe the transformation.

"Ready Honey?" Kat asked.

"Completely," Samantha replied.

They went down to the waiting taxi and a short ride later were being dropped off outside a busy looking club with a long queue. They walked straight past the queue and one of the bouncers waved Kat in. Samantha started to follow her but the same bouncer stopped her. "I know Kat, but I don't know you."

Samantha leaned in and whispered in his ear, "I'm Samantha, I'm Kat's plaything, if you're lucky, later you might get to play as well." The bouncer laughed, and let her in.

Inside the dance floor was packed but Kat led her straight into the middle and they began dancing and grinding to the music. Samantha lost herself to the dance, enjoying every time the crowd surges and pushed another body into her. Enjoying it even more when a body pushed up behind against her and knowing there wasn't a surge to cause it. Eventually Kat just stood to the side watching her lap up the attention.

After a while Samantha realized she was alone and started heading towards Kat, when she was abruptly stopped by a butch looking girl.

"I saw you with Kat earlier," she said, "keep away from her. She'll just use you and spit you out like she did me."

Without hesitation Samantha just hit straight back. "Listen Bitch. Two nights ago we were out shopping and she brought me off with her fingers in the changing room. Last night she went down on me until I came, and then she kept licking away until I was nice and clean again. Neither time did I have to do anything in return. Perhaps you should be asking yourself what I've got that you don't. Now fuck off out my way."

The girl flushed and just stepped aside. Samantha just walked straight past her without a second look, but inside she was beaming with joy, she'd just had her first cat fight and won so quickly it could barely be described as such.

"Anything wrong," Kat asked.

"Nothing I couldn't cope with," Samantha replied. She reached out and cupped the side of Kat's face, pulling her in for a long slow kiss. In the mirror behind the bar she could see the loser of her encounter watching with envy. She released Kat, "I'm having a fun night so far. Can't wait to see how it ends."

They stayed at the bar drinking, Samantha enjoying every admiring glance she was receiving, from both men and women, but always keeping in physical contact with Kat to ward off any direct approach.

Feeling slightly tipsy Samantha dragged Kat to the restrooms and into a cubicle. She pushed Kat against the cubicle wall, hitched up her dress and pushed a hand against her panties. Kat's eyes widened at Samantha's assertiveness and she started to speak but Samantha planted a finger on her lips. "Shhhh! I want to thank you for bringing me out. I've seen the way you've been watching me and I bet you've been thinking about this."

She slid a finger underneath Kat's panties. "See, you're all wet already." She eased a finger into her. "Wet and warm." She pushed down the top of Kat's dress and took a breast into her mouth, gently sucking and biting on the hard nipple." Kat let out a sigh causing Samantha to push a few more fingers into her, working her wet pussy.

There was a band on the door and a shout "find somewhere else, some of us are desperate." Samantha reached back and unlocked the door, but made no move to leave, instead moving to the other breast and pushing deeper into Kat. She paid no attention to the girl who came in and with a "fine then" locked the door and then sat down on the toilet. Once she left Samantha relocked the door and brought Kat off to a screaming conclusion.

They headed back out to the bar and stood watching the moving crowd of dancers, when all of a sudden Samantha felt a tap on her arm and a timid "excuse me". She turned and was amazed to see Sam's wife Jill in front of him, wearing a fancy dress school girl outfit, and then Samantha recalled the memory of her saying something about going to a bachelorette party while Sam was at the conference.

Jill continued, "I'm not sure I'm actually doing this, but I just watched you two making out in the restroom. And it made me feel a little turned on. And I'm at some awful party. And I wondered if, um, I might join you."

Kat looked at her, and then turned to Samantha.

"What do you think Sugar?"

Samantha attempted to say it was a bad idea, but before she got a chance Kat turned back to Jill.

"How turned on?"

"My panties got so damp, I took them off, here." She reached out and placed her damp panties in Kat's hand. Kat raised them to her nose and gave a sniff. Samantha tried to get Kat's attention, but without success.

"You little minx, I think you should come and play with us, but you have to do everything we say."

Jill paused for a moment, biting her lip. "Okay."

Before Samantha could object they were already in a cab heading back to Kat's flat. With Jill in the front Samantha finally managed to whisper into Kat's ear. "She is Sam's wife." Kat's eyes widened and her face dropped slightly. She turned back to Samantha. "She obviously doesn't recognize you. I think we have some fun and get away with this, just trust me."

Once at the flat Kat led them both to her bedroom. "This is the deal. Samantha here hasn't been with anyone but me before and told me she was also nervous, so you're going to lie on that bed and I'm going to make you wear a blindfold."

"A blindfold?"

"And we're going to tie you to the bed. I want you to be Samantha's plaything."

"I'm not sure..."

"Or I can ring a cab for you."

Jill hesitated for a moment, then walked over to the bed and picked up the sleep mask on the bedside table and slide it on. Then she led back on the bed.

Following Kat's instructions Samantha walked over and pulled the school tie from Jill, then pushed Jill's arms above her head and tied them together. She then unclipped the stockings and pulled them down Jill's legs, wrapping them around a few times at the ankle and tying them to the bed legs.

"Did you like watching her suck my breasts?" Kat asked.

Jill nodded. Samantha walked back over and unbuttoned her blouse, releasing her two pert handfuls of breasts, with the nipples already stiff. Sam's sex life normally had them covered with something like a slip, so Samantha took the opportunity to enjoy them properly, first just lightly touching the nipples and then gently pinching them. Jill let out a soft moan so Samantha lent over and took them in her mouth. "oh god that feels good. I never thought that could feel so good. Making me so wet."

Samantha continued to suck and caress Jill's but reached down and ran a hand up the inside of her leg. As she neared the top she'd lift her hand and start again on the other leg, getting slightly closer each time. "Please" Jill begged. Instead Samantha stopped completely and repeated the process with gentle kisses. Jill parted her legs as best she could and begged again. "Please you tease."

Samantha glances across at Kat, who was sat legs crossed in a chair one hand squeezing her breasts through her top, the other just resting between her legs. Kat nodded at her. "Stop teasing her and give her what she wants." With that Samantha lowered her face between Jill's legs and begin to gently lick. The moment her tongue first tasted Jill, Jill shuddered. "Oh god." Samantha wondered why Sam had never gone down on his wife, when she obviously enjoyed it so.

She licked harder and faster, as Jill's whimpers became moans, equally getting louder and quicker. "don't stop, please don't stop..."

"Stop." Kat ordered, and Samantha obeyed. "My turn. You can watch honey, why don't you slip out of that dress and those panties." Samantha did as she was told, stripping off slightly. As she pulled down the control panties, the part of her that was Sam sprung out, hard and thick. Kat climbed onto the bed and hitched her dress up revealing she had already taken off her own panties. She turned to face Samantha and then lowered herself above Jill's mouth.

In amazement Samantha watched Sam's wife begin licking out another women. Kat grinned and reached down to squeeze Jill's breasts. "mmmm, you're good at that" she purred. Looking straight at Samantha she leaned forward further and placed her hand between Jill's legs, sliding a couple of fingers into her. "Did you like watching Samantha do this to me earlier?" she asked, knowing full well Jill was too busy licking away to answer. "What do you think Samantha, do you like what you see."

Samantha was gently stroking Sam's stiffness, but nodded. Kat leaned further forward and tasted Jill for herself. "Mmm, she tastes good, I can see why you were licking her so hard." Jill began moaning again, and Kat stopped licking and lifted herself from Jill's face. "Not yet baby."

She climbed off the bed and took Sam in her hand. "Jill, I've just helped Samantha put on a big hard strap-on, would you like her to fuck you with it?" Samantha's eyes opened wide, and then Jill let out a soft "yes".

"Go on then Samantha. Fuck her. Fuck her with that big hard strap-on." Samantha looked hesitant. "Fuck her for me, I want to hear her scream in pleasure."

Samantha walked back over to the bed and climbed on. "Please," Jill whispered, "I'm so turned on, I need bringing off." Samantha eased Sam into her, and Jill let out a small moan as she did so. "That feels so hard. Oh god, please, fuck me with it." Samantha obliged, gentle rocking in and out of Jill, knowing Jill had never been this wet or willing for her husband. Jill began bucking underneath her. "Harder you bitch, fuck me harder, please"

Samantha built up her rhythm, pushing deeper and harder into Jill's willing pussy. She tilted her head down and began sucking Jill's nipples back to hardness, all the while hearing Jill pant and moan and beg like never before. Samantha reached up and grabbed Jill's bound wrists, hold them tight and pushing herself up so she could look down at Sam sliding in and out. Suddenly Jill shouted out "Oh god you bitch, I'm cumming". Samantha suddenly felt the tingling of no return and Sam shot his load into his wife, pumping himself several times more than he'd normally last, before collapsing onto her.

After a few moments Samantha realized what she had just done. "Oh god that was wonderful. I love you Sam, even if you are a big idiot sometimes."


Later Jill explained how she first thought Sam was acting so suspiciously about the conference she feared he was having an affair. She knew Kat from college and steered Sam to stay where she worked so she could check-up on him. Kat had discovered the outfit while Sam was eating that first night, and phoned Jill to tell her.

Jill had been shocked at first, until Kat had explained about her friend Daniel, and that it wasn't Jill's "fault". Together they'd hatched the plan to allow Sam to explore this side of him further.


Author's Note:

I hope you've enjoyed Sam's story. It took me longer than I expect to write as, although I always knew how Sam's story would end, the path took several unexpected turns. Plus, I've only written this when my girlfriend has been away for a few days so that I could slip on some of her clothes while I've typed.

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