VAMP.IT.UP Pt. 02

Story Info
Becky helps Paul to another first-time.
2.7k words
4.45
6k
6

Part 2 of the 5 part series

Updated 06/11/2023
Created 10/25/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This chapter explores another first-time for Paul, something he had often thought about, but never dared do.

Chapter 2: Be Who You Want To Be.

Paul was having a strange dream. In it, he was at a club and was having to fight off the attention of both men and women who all wanted to dance with him. A rather hot Italian-looking guy had managed to elbow a particularly gorgeous blonde out of the way and position himself in front of him. He was making lots of sexy, seductive moves. Paul wanted to look away but found himself feeling hypnotised and beginning to enjoy and encouraged the flirtation. Then it all went too far as the hunk leant in and gave Paul a kiss, while at the same time grabbing and squeezing his ass. Paul felt his cock being played with by this guy and then all of a sudden he ducked down.

Paul woke with a start and suddenly realised that his cock was actually being squeezed, in fact, it was being sucked. He shouted out "No!". Becky looked up from her work. "You want me to stop babes!" She said, "No!" He groaned, laying back on the pillow and letting the fabulous swirling sensations of her tongue and lips fill his mind with the most calming and satisfying thoughts. She was so talented, he wondered how she knew what to do, but, just as he began to relax again, she began to speed up and a moist finger began to toy with his ass in a most unusual way. That strange alien sensation completely flipped him over the edge and he erupted into her mouth.

Becky moaned in delight and after making sure she had missed none of his love juice, moved up the bed. Paul looked at her smiling face, her lips slick and shiny with cum. She straddled him and leaned in for a kiss and Paul reciprocated, loving the moistness of her lips on his. Then she did something he wasn't expecting. She forced his lips apart and let the cum she had kept in her mouth gradually flow into his, all the time swirling it around with her tongue.

"Did you like the snowball?" Becky asked, a big smile on her face.

"Snowball?" Paul looked puzzled.

"Don't worry, I can see you did." She rolled over and lay beside him.

"And what about last night, was that fun?"

"It was amazing."

"I'd second that, but I meant at the club," Becky laughed!

"Yes, yes, it was. It's a good club, but it was probably more fun for you than for me. I mean you were just so popular! How many guys did you end up kissing?"

"Ha ha! I wasn't exactly counting, but I wasn't that much of a tart! Maybe half-a-dozen. It's their prize for making me feel good by turning into loved-up puppies. Anyway, aren't you including the girls, or don't they count?"

"Err, I guess they count."

"They definitely do. My favourite kiss was with one of them. Do you remember the one with the brown hair, long silver necklace and big lashes, the one in the red minidress?"

"Yes, she was really hot. I had a dance with her too, but she seemed to prefer you!

"Well, to be fair, you do have to up your game a bit. You did know she was trans?"

Paul looked at Becky.

"What?"

"She had a dick."

"No way."

"You're not transphobic are you?"

"No, not at all. I just can't believe it! She was perfect. I'd have never known."

"Oh, you'd have known eventually!" Becky laughed. "So what about you? Did you have any success with anyone or am I the runaway winner?"

"Oh, you are definitely the winner. My highlight was when you grabbed me for the last few dances before we left and I could see the look of envy on guys' faces."

"So no snogs other than with me!"

"Nope, well, almost, but that was from some gay guy who took a liking to me and tried it on."

"Ha ha! You should have kissed him. That would have made you the centre of attention! You'll learn!"

"Well, it's obviously made an impression on me. I was sort of dreaming about it when you woke me up."

"Oh! And what exactly was going on in that dream? You were really hard!"

"Nothing really, he just touched me, and then I woke up, and it was you!"

"So you fancy guys then?"

"No," Paul paused, "well I'm not sure really, I don't think so. I think it's girls that turn me on. I love how sexy they look. But in my dream I think I was sort of being you, and the fact he wanted me was really exciting."

"Ha ha! So you see yourself as my rival then?"

"Well clearly not! I'm not even close to your league."

"Why not? I think you could scrub up well."

"What does that mean exactly?"

Becky studied his face.

"Yes, you've got the right features. I reckon you could be as passable as that brunette."

"What? A girl? No way Becky, she was amazing!"

"Do you want to see?"

"Err."

"Well, you had to think about it so that's a yes. Now, let me take a look at you."

Becky pulled the covers off the bed and studied Paul's body.

"Prepare to be amazed! Now come on, get up! We've got work to do!"

Paul had had his doubts, but there was a part of his psyche that he knew he had always fought. That he did sometimes suffer from a terrible feeling of how lucky pretty girls were, and that if only he had been born a pretty girl, how much easier his life would have been. He was so envious of their clothes and the way they looked. Was Becky right? Could he be a pretty girl? He didn't think so, but then a lot of things that he thought a few hours ago were no longer true. This was too good an opportunity to miss.

He baulked a bit when she gave him a lady's razor and told him to shave his legs and armpits, but they were not that hairy anyway and as winter was on the way no one would be seeing them. He just got on with following her instructions while she fixed some brunch. He loved the whole girly experience as he stepped out of the shower and began applying big blobs of body lotion to his legs and torso. The sweet jasmine smell and the amazing feeling of how soft and smooth his skin was, made him smile inside and his cock stiffen.

Becky had jumped into a 'bear' onesie which looked completely ridiculous, especially with her glasses on, but it left Paul free to wrap himself in her baby blue fleece dressing gown which felt absolutely sensuous against his skin. She inspected Paul's efforts and fixed a few places that she said he had not adequately depilated, including around his groin. Just being in her dressing gown with her fussing over him, he already felt so different.

She measured his chest with a tape and came back with a maroon bra and matching panties which she helped Paul into. She gave him a larger version of those breast enhancers she had flung on the bed the night before and he was quite impressed with how they filled out his chest.

For the next hour, Paul sat back as she painted his face. First, she trimmed his eyebrows, assuring him that she would just give them a little thinning and some more shape. She explained each of the next steps. Concealer; liquid foundation; powder; blusher; bronzer; eye shadow; eyeliner; false lashes; and, finally, lip pencil and lipstick.

Paul really wanted to see what she had achieved, but she told him to keep still, as she had not finished, and he was only to see her work when it was done. She had made him wash his hair in the shower, and now she began to trim it. He expressed his concern, but she assured him that she was just making his hair a bit more unisex. She applied some gel to give it some body and brushed and cut for what must have been another 30 minutes. Whatever she was doing he was going to have to live with, but once she had started he had no option but to trust her.

She finished drying and straightening his hair, touched up his face and applied some mascara. She stepped back and beamed at him. She grabbed her mirror from the dresser and Paul looked with some trepidation at what she had created. At first, he thought it was some trick, but when he blinked and smiled and saw the reflection doing the same he realised that she had indeed achieved the miracle she had seemed so certain she was capable of.

"So, what do you think?"

Paul was moving his head from side to side and playing with his hair.

"I mean, I know I'm not a girl, but I definitely look like one! I even look good, I can't believe it!"

"You do. And more than good, you're smokin' hot! Hey, you look a bit worried."

"It's the hair. I love it, but I've got to go back to being a boy."

Becky swiftly put him in a ponytail and brushed his fringe to the side.

"There! You looked good in that ponytail last night. What do you think."

"Wow, yes, that works well."

"Now let's get you dressed. Here, put these on."

Becky passed Paul a pair of tan tights, a dark pink plaid mini-skirt and a black top.

"Haven't you got something a bit less totally girl?"

"Only trackies, and after I've gone to all this effort to make you look stunning, I think wearing those would be an insult. You could wear jeans, but we'd need to work on a tuck, and we don't have time for that."

"Why? What's the hurry?"

"We need to go get you some shoes and the shops shut soon, I'm a size six and you are a size eight. Lucky really, anything more than that and it would be quite difficult. We can also get you a few other bits if you like: there's a Claire's in town that does clip earrings and maybe you can get a necklace of your own."

Paul had not really heard any of that and, somewhat dazed, replied, "you mean I'm going out like this."

"Of course! Why on Earth not? No one will have a clue you're a guy."

"Until I open my mouth."

"Good point. We'll work on that, but I'll try and do all the talking."

"Mmm!"

"Oh come on Paul!"

"Oh sure Becky, that's another thing, what are you going to call me when we are out? Paul?"

"Well, I could call you Paula, but that's no name for a girl. Hello Chelsea."

"Don't I even get to choose my own name?"

"Sure honey, what do you fancy?"

The truth was Paul really liked the name, Chelsea.

"Chelsea," he eventually mumbled.

"Good!" Becky laughed, "any other concerns Chels?"

"Well, yes, but like you said, the shops will be closing soon."

Becky grabbed her perfume and spritzed it over Chelsea's neck before grabbing her hand and pulling her up and out of the door.

If it had not been for Becky's never-ending set of instructions and orders Chelsea might well have felt paralysed by fear, but instead, she was overwhelmed with having to deal with all the somewhat subtle, but important, features of not just appearing as a girl, but also acting like one. She had to take smaller steps. Thrust out her chest. Keep her arms as close to her sides as she could. Try to place each footstep in front of the last to give a natural sway of her hips. Head-up. Chin-out. Act the part!

By the time they reached Primark, Chelsea was feeling much more comfortable in her new skin. Becky was no longer giving her a running commentary on her failings, but instead a lot of encouraging compliments. Chelsea had even made eye contact with a few people, and some had given her a lovely smile back. She had to admit. Becky was right. She could go out as a girl and pull it off.

Choosing shoes as a boy had been pretty easy as you just grabbed the cheapest pair of grey trainers, but there was so much more choice as a girl, and a look you were going for. As promised though, Becky made all the decisions and did all the talking. They left Primark with a pair of moderate-heeled ankle boots with a big silver buckle, some everyday pumps and a pair of heeled Roman sandals. In Claire's, Chelsea picked up some fabulous hoop earrings that clipped onto the ear and left with two sets and a silver necklace with a large 'C' on it. Becky bought everything on her card, which Chelsea was pleased about as that was another 'problem' dealt with.

Chelsea really felt the part with her shopping as they walked back to the residence and had both a natural sway and spring in her step. She hated shopping as a guy, but this had been really exciting, and she couldn't wait to get home and try on everything properly.

"Hey Chels, I'm famished. How about you treat me to a pizza at Zizzi's and then we're quits."

"Now?"

"Look, Chels, yes, let's just do it. I know it's a bit of a baptism by fire, but you'll see there's nothing to worry about. Everyone's very progressive these days and no one cares if you're a hot chick who's packing something extra. You're a hot chick. Right?"

Chelsea gave a worried smile, but so far everything has been very slick, so she went along with it, especially as she really liked Becky and felt that she definitely owed her a treat for instigating this rather amazing adventure. She was also really beginning to feel like a girl inside, and it was a wonderful feeling that she didn't want to stop. It was everything she had ever hoped it would be.

"When you talk, try to not use your throat. Speak from the front of your mouth. Your voice will still be a bit deep but will sound far more girly. Try it. Try saying 'A table for two please.'"

Chelsea did. It sounded OK. She repeated it a few times until she was standing in front of the greeter and listening to the reply, "Certainly ladies, please follow me."

It was a great meal for a pizza. Crisp and really tasty. Chelsea learnt a lot about the different challenges a girl faces, especially about maintaining her lipstick by eating small mouth-sized portions, keeping her hair out of her food by taking the food to the mouth and not bringing her mouth to the plate, and generally looking like someone who was enjoying their food rather than impersonating a ravenous wolf.

They even shared a bottle of prosecco and were both slightly tipsy by the end of the meal, so much so that they were both shamelessly flirting with the waiter who had been giving them extra special service during the whole meal. It turned out he was also the owner and gave them a free tiramisu and limoncello with their coffee.

It was now dark and fortunately, Becky's residence was just five minutes walk away. They giggled and laughed as they linked arms all the way back there and, no sooner had Becky dragged Chelsea into her room, than their lips met.

Chelsea would never forget this kiss. Her first kiss. The kiss of two sensual and caring women. Slow, soft, tender, loving and unbelievably sexy. Their lips gently caressed each other's, and each time little electric shocks sent sparks of pleasure running through Chelsea. Their tongues flitted about, exploring, but not probing. Then the feeling of their two mouths locked together, arms wrapped around each other, soft cheek against soft cheek, all within the cloud of delightful perfume that enveloped them. The feeling of their clothes, brushing against each other. Nylon on nylon as their legs rubbed together. It was simply beyond magical.

In a beautifully unhurried bout of sensual lovemaking, they progressed to the bed, having slowly unwrapped each other. They spent a long time in a soixante-neuf, pleasuring each other until the inevitable climax. Then they would kiss and caress until they could cum again. Eventually, they showered and Becky showed Chelsea how to remove her makeup. They slowly fell asleep in the darkened room. Chelsea spooned against Becky.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
Cristal_di_CantaCristal_di_Cantaover 1 year agoAuthor

Thanks Sabrina - my thinking was it's still a first time!

SabrinaGLangtonSabrinaGLangtonover 1 year ago

So loving this new series, I didn't see the transformation coming but I'm so glad it, um, came... Thanks for sharing...

Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Becoming a Drag Queen A trip to San Francisco descends into the drag queen world.in Transgender & Crossdressers
Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.in Transgender & Crossdressers
Southern Hospitality Milfy seductress does all she can to score the boy next door.in Transgender & Crossdressers
More Stories