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Samantha's First Time

By: Samantha

It was an ordinary Saturday lunchtime for Edward, he was having lunch at a restaurant with his female friend Lisa. He was a young 24 and she a young 25, their relative closeness in age a result of both meeting at first year of Uni.

Their conversation was halted somewhat when Lisa spotted two of her friends, Sarah who was a juvenile 18, and Ellie a more mature 22 year old.

"Hey you two!" The two came over to the table where Ed and Lisa were sat.

"Hi Lisa, Hi Ed" the two chimed.

"Sit down, sit down" Lisa urged and beckoned to 2 adjacent seats.

"How's things? I see you've been shopping"

"Good good, yeah, we got some good bargains too"

The three women chattered and tried to involve Ed where they could, though the chatter was of a feminine nature.

"I love your skirt, Ellie" effused Lisa

"It's lovely isn't it, I got it a couple of weeks ago"

"It is so cute on you, really pretty, don't you think so Ed?"

"Wha... oh yes, it's very pretty, looks lovely on you" Ed was slightly flustered by the female chatter, what did he know about skirts?

"Well it wouldn't look very pretty on you Ed, unless..." Ellie winked.

The three women giggled.

"Yeah we'd have our work cut out to get Ed in that skirt" they laughed

"Aww sorry Ed, we're just teasing, ignore us" said Sarah

"You know, I think Ed's secretly enjoying the tease, if I didn't know better" Ellie teased further

"Yeah, your skirts knock-out, but I would look better in it" Ed fought back a little, then instantly regretted what he said. That sounded like a dare, he hoped it hadn't registered with Ellie.

"Oh? Well we can fix that, can't we girls" Ellie looked for confirmation from the other women. They grinned and nodded to each other.

"Sure, we can fix that" said Sarah

Oh shit... what have I done, thought Edward to himself. The three women noticed the look of trepidation on his face, which made them laugh that little bit harder.

"Hey, you's aren't doing anything this afternoon are you?" Ellie enquired of Lisa and Ed.

"No, are you?" Ellie looked at Sarah in acknowledgement "No we're free all afternoon"

"Why don't we continue shopping, we could drag poor Ed along!" said Sarah

"You don't mind do you Ed?"

"Erm... well I guess"

"We'll get you a skirt as pretty as Ellie's, I promise"

The three giggled. What had Edward done? Him and his big mouth.

The group of 4 left the restaurant after paying up. And headed to the shops. They made their way into the first shop along their way, which also had a sale on. The women perused the clothing, while Ed hung around, rather self-consciously. The women chattered among themselves and finally called over to Edward.

"Hey Ed, come here"

"What is it?" Ed came over

"What do you think of this skirt, it's really pretty don't you think?"

"Erm... I guess so"

"And Ed, you did say earlier... and look here, they have it in a size that will fit you, isn't that lucky! What do you say girls?"

"Let's get it! Are you up for some fun, poor Edward?"

Edward knew he was in for it now, him and his big mouth. The women couldn't not giggle together at the expression on his face.

"Now we need to find you something pretty to go on top" chipped in Sarah

"I saw a darling blouse earlier, let's go buy this skirt, then we'll go get that" said Ellie

They bought the skirt, and headed out to the shop where Ellie had seen the most darling blouse, as she put it. That was soon purchased aswell.

"We're gonna have to go the whole way with this, you know girls, we'll have to get him some underwear"

"Yes!" exclaimed all 3 women.

They headed over to a lingerie store, and set about finding the most feminine underwear they could for Ed, it was 'a mission'.

"This bra and and panties set are to die for, and they'll fit him" the women settled on a pink lacey bra and pantie set, with ruffle trim for extra femininity.

"And notice, the panties aren't too skimpy, so he'll have room to tuck, err, himself in" the 3 women laughed at that.

"Poor Ed!"

"Lucky Ed!"


Little shopping expedition over, for now, this time, the foursome headed back to Lisa's apartment. Oh poor/lucky Edward, what has he let himself in for.

They entered the apartment, and they placed their bags down.

"Who wants a drink?" chirped Lisa

"Me" everyone else replied

"I'll go open a bottle of wine then, white okay for everyone?"


They all had a drink and chatted about other things, as if to lull Edward into a false sense of security, or keep him on the hook longer. After they each had finished their glass of Chardonnay, Lisa spoke up.

"Well, we won't put this off any longer shall we girls?" she said looking at Edward, smiling

"Y'know, you did kind of force our hands, you shouldn't have said Ellies skirt would look prettier on you, you asked for it"


"Resistance is futile, dear Edward" said Sarah

"Come on, we've got work to do, and you've got a shower to take Ed"

"Why?" asked Ed

"We've got to get rid of that icky man hair, if you're to look pretty, and you want to look pretty don't you?"

Three against one, Ed's odds weren't good, so he submitted himself to his feminine fate.

"Look in the cabinet, you'll get a new razor in there, we want everything gone, and I mean everything" Lisa said in a faux stern voice.

The three women chuckled.

Ed, resigned to his fate obliged, and headed to the bathroom, pausing to collect a bath towel Lisa handed him.

He locked the bathroom door behind him, and started to undress, trembling slightly, and found a new disposable razor from a multi-pack in the cabinet. He ran the shower for a moment, and stepped under it to get wet, and found a bottle of foam to shave with. With slightly shaky hands he then went about shaving everything, as instructed.

Rinsed off, and hairless below the neck, Edward stepped out of the shower and set about drying himself off. His legs looked weird all fresh and smooth, but it wasn't dislikeable, it felt sorta nice.

Dried off, he wrapped the towel around himself, and unlocked the bathroom door and stepped into the hall. The three women were waiting in the living room for him, and looked around when they heard the door unlock.

"He's even wrapped the towel around like a girl!" laughed Sarah, the others joining in the apparent hilarity.

"Aww, bless"

Edward blushed.

"Now come with us through to the bedroom Edward" said Lisa

"Well we can't call you Edward can we though, Lisa?"

"That's right, we decided that instead of Edward, you're now Samantha, I think that's more appropriate, eh girls"

The three nodded, and Edw... Samantha blushed harder.

"Now, come through, and we'll get you looking all ladylike"

Lisa led Samantha through to her bedroom, the others in tow.

"Here's your new underwear Samantha, go take it through to the bathroom and put it on, we'll wait here" instructed Lisa

"Come out and show us when you've got it on" chimed in Ellie

"Don't forget to tuck yourself in!" added Sarah with a suppressed giggle

Samantha, resigned to her fate, did as instructed, and took the matching bra and panties through to the bathroom, noticing a chill on her legs as she did so.

The panties were easy enough to get on, and Samantha managed to tuck the offending manhood back and under satisfactorily. The bra was a little bit of a dilemma though, with having no such experience of putting one on before. But with a little thought and application of engineering, it was soon on. Samantha braced herself, and stepped out of the room to face the women.

"Oh you look divine!"


"He's even got the bra on properly, I think he must have done this before, don't you think?"

All three laughed. Samantha blushed.

"You're so smooth Samantha, doesn't it feel lovely?" asked Ellie

"Well... I guess" replied Samantha

"Not one for many words just now are we? That's ok"

"Here, now we'll get you in that pretty skirt, it's going to look super on you, I can tell" Lisa handed him the skirt. It was black, figure hugging cut, with a subtle floral design through it.

Samantha sat on the edge of the bed, and placed either leg into the skirt, and stood up to pull it up to the waist. Fastening it at the front and swivelling it around to sit in place, rather too expertly. The women noticed.

"Are you sure you haven't done this before... hmm" Lisa looked curiously at the other women

"She's a little too good at this I think, I'm suspicious" said Sarah

"I haven't done this before, honestly" insisted Samantha

"The lady doth protest too much methinks" observed Ellie

"Come on, now the blouse" Lisa held up the blouse for Samantha. It was ivory, with sheer pouffy sleeves, and a high neck, replete with a bow, and dainty buttons down the front.

Samantha donned the blouse, and did-up the buttons, finalising with straightening the bow on the front of the neck.

"Beautiful woman you!" cried Ellie

"Give us a twirl!" cried Sarah

"You look soo divine, girl" cried Lisa

"Go on, give us a twirl, girl" repeated Sarah

Samantha blushed and obliged, giving a twirl for the girls.


"But girls, we're missing something, she needs heels, and I've got just the pair" said Lisa, going over to her closet.

She had a rummage in her closet, and stood up, turning around to produce a pair of 4" black high heel court shoes.

"These will work, you should be fine Samantha, you're only one size bigger than me, and anyway, a girl's gotta suffer to look good, the sooner you learn that the better"

The others laughed "Too right".

"Sit down and I'll get them on you" commanded Lisa

Samantha obliged again, and sat on the edge of the bed, while Lisa knelt down and placed the heels on Samantha's feet, albeit with a squeeze.

"Stand up"

Samantha stood up, a little unsteadily

"Now walk through to the living room, and back through here, see how you walk in them"

Samantha did as told and walked gingerly through to the living room and back through to the bedroom. The girls giggled at the awkwardness of motion.

"Hmm, we'll have to work on your deportment I see, but we have time"

"We do?" asked Samantha, looking at Lisa.

"Sure we do, you don't think this is a one-off do you?"

"I... I..."

"Of course it isn't, you're having fun aren't you, you're a natural" Lisa interrupted

"Eh girls, this is just the beginning right?"

"Sure is, we have work to do with you Samantha, but don't look look like that, you'll thank us in the end"

"She sure will" added Ellie

"And who knows, once we've got you the right wig, and taught you the secrets of good make-up application... you'll be irresistible to the guys" said Lisa

The other two women nodded in agreement.

"We've got plans for you, and you know you can't resist us... Don't worry girl, you'll go far with us by your side"