Holly's First Encounter

In my previous stories I have described how blonde 20 something Holly was persuaded to remove her clothes as part of an "unplanned" striptease. In reality they were both planned but she was only tempted into it because her audience were under the impression, she was doing it reluctantly. What follows is the story of how she first took her clothes off in front of an audience, albeit one man on his birthday, and how neither were expecting it when they woke up that morning.

Holly's mom Kelly has a casual but intimate relationship with a guy called Paul. Paul lives alone and works as a freelance accountant which means he works from home most of the time.

On the day of the encounter, it is Paul's 45th birthday. Kelly is open minded about her daughter's sexual activities. Holly is a virgin and her experience with the opposite sex at the age of 18 is, as you'd expect, limited, which still gives her an innocent outlook on the type of things that men find sexually arousing. Kelly has bought her a vibrator, so she has at least had the feel of something inside her.

Kelly wants to give Paul a saucy present for his birthday and at the same time feels Holly needs to the experience of a real man. She is very broad minded so the thought of her daughter being offered up on a plate, so to speak, to her lover is doesn't faze her. Equally Holly trusts her mom implicitly so even though she doesn't know what her mom has planned, Kelly knows that she will go along with it. She knows Paul won't turn down the opportunity to sample Holly's delights if there is a chance, although at first, he will be nervous about how to approach the offer. Hopefully, all will become clear as the story unfolds.

Kelly has given Holly a card to drop into Paul on his birthday. Holly works as an office junior at a local firm. She walks home and passes Paul's house on her route.

Holly always dressed in office attire for work, smart but alluring. This day was no exception.

It's important to mention that Kelly occasionally liked to buy clothes for Holly. Items that she thought would take her from typical teenager to proper womanhood. Skirts, tops and sometimes even underwear. In fact, only the day before she had purchased 3 pairs of panties from a high street chain, all matching in design but in 3 different colours. This was part of Kelly's plan. She chose a style and colours that she knew were to Paul's taste knowing full well that Holly would wear one of them, or possibly even two, the very next day. She always liked to wear her mother's gifts as soon as the opportunity arose. If she was wearing tights, sometimes she wore two pairs, one over, one under, but mainly for practical reasons, but little did she know, tights are a big favourite of Pauls..

Around 5.15 Paul hears the doorbell ring. He answers it to see Holly standing there holding an envelope.

"Hi Holly, nice to see you, is that for me?" he asked.

"Yes, mom asked me to drop it in on my way back from work". She replied.

"Please, come in, would you like a drink, tea or something else?"

"Thanks, I'd love a coffee" she said.

Paul takes a few seconds to cast his eye over Holly's appearance. She always dressed in office attire for work, as you'd expect.

It had been another warm day, so she'd had removed her light jacket she wore that morning and carried it on her journey from the office. She wore a long sleeved white peasant blouse and a plum coloured mini skirt which stopped about 6 inches above the knee. It was totally smooth, by that I mean no seams. Paul guessed it was nylon or even a jersey type material. At the moment It wasn't tight enough to constrict her movement but he'd no doubt it would become more stretched when she sat down.. Her legs were sheathed in what looked like 10 denier glossy black hosiery, the form of which Paul was unsure. She always wore heels and today was no exception, shiny mauve to match her skirt.

Paul showed her to the lounge and quickly nipped to the kitchen and returned with two mugs of coffee.

After a few minutes chatting Holly suddenly remembers to give Paul his card.

"Sorry, I nearly forgot to give you this. I've been holding it ever since I go here" She hands over the envelope containing his birthday card.

"Oh wait, I just remembered, Mom said I should read the message she's written to you. I don't know why, it's not as if you can't see it yourself."

"OK, here, you open it then" Paul said smiling as he handed it back to her.

Holly took the card out of its envelope and looked at the cover.

"Gosh, that's quite a cheeky picture isn't it?" she showed it to Paul.

"That's typical of your mom, I'm not surprised she's picked something like that" he said.

I was a picture of a rather well-endowed young lady in a bikini. Holly read out the message on the front "Are you getting any older? Take this test"!

Holly opened the card and read the inside. "What colour are her eyes" If you haven't noticed then you haven't aged a bit".

"I can't remember" said Paul laughing. "So, you haven't aged then" laughed Holly, good for you.

"Oh wait, what's this?" she said. "Read the message on the back"

.

Holly turned the card over and read what Kelly had written on the back.

"Happy Birthday, this lovely present I've sent will make your big friend John Thomas stand to attention and make a special delivery in his favourite place.

Holly looked puzzled; Paul looked surprised.

"I don't understand, I wonder what it means" she said. "She didn't give me any present to give to you".

"Oh, that's strange" said Paul, trying to figure out the message himself but hoping his slight hunch was correct.

"I know she's arranged for a small get together at the weekend. She said she that would be her pressie to me, you know, arranging the food and drink at her place and everything". He explained.

"Well, I'm puzzled then" said Holly, "I don't have a clue what she's on about".

Paul hoped, his stomach had butterflies at the thought of it, that Kelly was up to one of her saucy tricks.

He thought maybe Holly was his present, but how to suggest that to her would be a nervous and risky conversation.

Kelly knew he found her daughter attractive and had discussed with him how much she wished she could have more experience with men but wanted them to be more responsible than the silly teenage boys she hung out with.

Kelly is very opened minded about their relationship, and he knew that she could trust Paul to treat Holly properly if the opportunity arose where they were together alone.

Likewise, Holly knew that if her mom knew a respectable man who could help give her some guidance in the ways of love, old or young and she'd try do what she could to excite him.

"Who is John Thomas, is he a friend of yours then?" she said innocently.

"Err, sort of I guess" said Paul a little cautiously.

"Is he a soldier or something?" asked Holly.

"Why do ask that?" Paul replied, slightly confused.

"Well, the message said stand to attention. Aren't that what soldiers do?" she said.

"Yes, you're right I suppose, I hadn't thought of it like that". Paul Laughed.

"Well, is he?" she repeated.

"Err, no he's not a soldier. I think your mom has used a name that sometimes can refer to a certain part of the body".

"Oh, I see" Holly replied.

"You know like a nickname" said Paul.

Although Holly was not 100% innocent it was obvious, she'd never heard the term before.

"What part of the body does she mean?"

"Well, I know your mom's sense of humour, and she's being a little bit rude". He told her.

"Why, what do you mean, is it embarrassing then?"

"Yes" he laughed, but at the same time trying to hide his embarrassment.

"Oh gosh, really, does she mean a part that's private?"

"I think she does".

Holly's eyes widened and her cheeks turned a light shade of pink.

"Oh gosh, that's really cheeky of her isn't it?, fancy her putting that in your card. I don't get what she means by standing to attention though" she questioned.

Paul's face reddened even further.

"I don't know if I can say, it's extremely rude".

"Oh" said Holly, her face deep in thought.

"Does she mean, you know, when it sort of, gets bigger?"

Paul's expression changed to one of surprise. He wasn't sure how much Holly knew about the facts of life. A bit naïve really, she is 18 and one would hope that she had some knowledge by now, even if it was just through girly chit-chat.

"Oh, you know about that then do you?" he asked.

"A little bit, not much, I know men's bits grow and get harder before they, you know, do it".

"Sorry Holly I didn't realise; you must think me terribly stupid". Said Paul.

"No not all, it must be embarrassing for you to talk to someone my age, especially as you know my mum, about private things like that" she replied.

"You have no idea Holly, look how you made me blush?"

"It's alright, don't be embarrassed. I have had some experience with a boy, gosh I can't believe I've said that".

"Oh, I didn't know, then why should I, its personal" replied Paul.

"Its OK don't worry, what's that last bit about, what was it, nectar or something?"

"Ah, well she's been rather poetic, I think, about what happens when the part gets, you know, excited".

"I think I know what she means. It's that the gooey stuff that comes out isn't it?"

"You could call it that I suppose" he said trying to avert his gaze from Holly.

"It's alright, Mom knows that I've seen one and touched it, I don't know if she knows but it got really excited. The gooey stuff went all over my hand".

"Oh really" said Paul, "look, you didn't have to explain if it's a secret".

"Oh, I don't mind, I know you so it's not so embarrassing".

Holly put her finger to her mouth in a thoughtful pose.

"I'm still not sure about one bit of the message she put in your card, what does it say again" she looked at the card.

"It says, the present I've sent, but she didn't give me anything to give you".

Paul's mind started to work overtime again and wondered if he should just say what he thought. Nothing ventured nothing gained. He was almost sure that Kelly's message referred to Holly as being his present and if he was wrong then he'd just apologize and think of an excuse to cover himself.

Before he could speak Holly said, "the only thing she sent is me".

Paul breathed an inner sigh of relief and felt a slight stirring in his groin. Still playing in carefully he asked

"Do you think she meant you are the present then".

"I can't think what else she could mean" replied Holly.

"Maybe me visiting you is the present".

"Maybe it is" said Paul "and a lovely present you are".

"Ah thank you" said Holly.

They continued to sip at their coffees and chat until Holly piped up.

"Hey, I just thought, what about that line in the card about, you know" she lowered her eyes, "making it stand to attention".

Paul's stomach took another flutter, part from nerves but mostly from excited expectation.

"Oh yes, I forgot about that" said Paul looking down at his coffee and desperately trying to hide the fact that he was fibbing.

Holly picked up the card again and read it once more.

"The lovely present I've sent, me..., will make John Thomas, your... err....... thing stand to attention. Wow, that means I'm supposed to make it doesn't it?"

"It very much sounds like that's what it means" said Paul.

"But how do I......, you know you, make it do that?"

Blushing again Paul replied, "What happened with the time when you played with one before?"

Holly cleared her throat.

"Well, it was with a boy at college, he said he fancied me, and I liked him a bit. We kissed and he put my hand on his lap and asked me to rub it, so I did, then he took his thing out and I stroked it".

"Oh, I see" said Paul, "and is that when it made a mess?"

"Yes, it got very stiff, it didn't take long, only a few minutes and then the gooey stuff came out". she told him.

"Did you do anything else apart from stroke it, to make it get stiff I mean?"

"No, I just stroked it. Why, what else can you do?" she asked.

"Did the boy ask you to do anything else?"

"No, but he made some noises especially when the stuff shot out".

"That's quite normal, but sometimes guys like you to do other things, you know help stimulate to make it get stiffer".

"What sort of things?"

"Well......If they're polite, they might ask if they can touch your body" Paul nodded towards Holly's well-endowed chest.

"Or they might try to look up your skirt or put their hands on your legs".

"Wow, I didn't think they would try to do that." said Holly, "Is that what would make yours stiff then, sorry, stand to attention" she giggled.

"I think it would for most boys or men" Paul told her.

"So, if part of moms present to you, I should try to make your, you know what, get stiff"?

"I think that's what she's suggesting. How do you feel about that?"

"Well, she has said to me in the past that I should learn about that sort of thing, and it would be better with someone I know who has experience, so I suppose it would be OK to have a go"?

"OK, if you're sure then" said Paul.

"What do you want to do then or is there anything I should do?" she asked him.

Paul hesitated. "Well, the things I mentioned before would be great, but I particular tastes are slightly different, you know, to get things happening quicker" he said glancing down and pointing towards his groin.

"Oh, ok" said Holly with a slightly confused expression.

"What sort of things then?"

Paul swallowed hard. This is it, he thought. A chance to explore the lovely delights of all things Holly and in a way that was most arousing for him.

"It's like this" he began. "You have a smashing figure Holly and what you are wearing is very appealing, I've always liked the office look, but I'm guessing it's what you normally wear to work".

"Yes, I wear the same sort of thing most days, different colour top or sometimes a longer skirt maybe".

"So, you haven't altered your look just for me today?"

"No, I didn't expect to be doing anything different today, so I just wore what I'd normally wear. Is it OK?"

"Yes, it's more than fine really. As I said, I prefer the office look".

"Is there a problem with it?" she asked.

"Far from it, in fact in maybe perfect for detecting something" he said.

"Detecting something, what can you detect, I don't follow?" she asked.

"To be honest, I'm still a bit nervous about discussing it, I might seem like a pervert or something".

"Don't be, I don't mind honestly" she assured him.

"Ok, if you're sure" she nodded her acceptance.

Paul began "first of all, I've been admiring that lovely black glossy sheen on your legs ever since you arrived".

"Oh, have you, that's nice, I like it too, they make my legs look silky don't you think?"

"Very sexy" Paul agreed. "Do you mind me asking what they are?"

"What do you mean?" she asked.

"Are they stockings?"

"Oh, I see what you mean, no they are tights, is that important?" she asked.

"It might make it tricky" he said.

"Make what tricky?"

"Err... finding out about something that might get things moving down here" he said pointing to his crotch.

"What sort of thing is that?"

"Oh, it's just that, I really like tights, and yours are gorgeous, but they tend to obscure another item of clothing that are one of my favourite items of ladies clothing".

Holly smiled, "I guess you must be talking about knickers, then are you?.... cheeky"

"Absolutely" he replied.

"You see, it's like this, sometimes I occasionally check out ladies in the street, if they are wearing tight skirt or trousers, to see if I can see their VPL".

"Their what?" she asked curiously.

"VPL, I thought you'd know what that is".

"No, I'm not sure what it means" she told him "What is it?"

Blushing a pale pink again Paul began, "Well it's sort of an impression or outline that a pair of ladies knickers make which shows on the outside, through the material of their skirt, or trousers, leggings, whatever. It stands for visible panty line".

"Oh, I see" said Holly "and wearing tights might obscure the outline you mean?"

"That's right" Paul replied.

"But what about if the girl is wearing her knickers on the outside her tights, that would be better wouldn't it?"

"I guess it would" he agreed.

"Well, that's good then isn't it?"

"Why, what do you mean, what's good?"

"Silly, can't you guess?"

"Guess what?"

"That I happen to wearing a pair of knickers over the top of my tights"

Holly placed her hands on her hips as if to establish the area where her knickers were situated. As if Paul wouldn't know.

"Oh, I see, is that right?" said, Paul trying desperately to look as cool as possible but its reality getting very excited at the prospect of seeing what the lovely Holly had decided to clothe her intimate regions in that morning.

"Yes, but I don't know if I have, what did you call it, a VPL?" she said.

"How would I know?"

Paul cleared his throat nervously.

"For the best way to find out you'd have to have your back to me. If you were facing me, there wouldn't be any sign, or very little, anyway".

"Oh Ok" said Holly, "Do I need to stand up then?"

Paul's pulse started to race. "Why, do you need to stand up?" he said.

"So, you can see if I have a VPL" she answered.

"I wasn't expecting you to show me, are you sure, it's very personal".

"What is?"

"You know, showing me, an older man, a friend of your mom, the impression your underwear might be making through your skirt" he explained.

"Please don't worry about that, I feel much more comfortable with you, certainly better than I do with some of the older men at the office. Some are old enough to be my grandfather, but I can see them looking me over sometimes. You know wondering what I'm wearing underneath and everything and trying get a look down my blouse.

"I thought you said it would help make, you know, John Thomas, stand to attention" she said smiling innocently.

"I'd love to think it will, in fact I'm sure it will, but it's still rather a private thing you're offering to do Holly?"

"Well, that's settled then" she said, "Mom had said that I am your present, so I should do my best and try to make it do what she says".

With that she rose from the sofa, smoothed down her skirt and looked at Paul eagerly as if waiting for his instruction what to do next.

Paul looked at her, surprised by her eagerness and willingness to go through with it, but not knowing how to start things off.

Before he could say or do anything, Holly spoke in a soft voice

"What should I do know?"

Paul stuttered a little then looked at the gorgeous sight standing a few feet in front of him.

"It's probably better if you turn round so you have your back to me" he said quietly.

"Ok, I guess that would be better" and she shuffled around on her black stiletto shoes until she had her back to Paul.

Now that Holly couldn't see Paul's face his expression became more brazen. With Holly's rounded cheeks filling out her skirt like two beautiful peaches, he rubbed his crotch gently and silently mouthed the words fuck me! to himself.

Holly's skirt fitted quite tightly but by no means clung to her cheeks so Paul couldn't make out much of a VPL at the moment. He figured that she may have to bend forward or just push her bum out to reveal any impression what she wore beneath it.

"Wait" said Holly. Paul's heart sank.

Had he gone too far with this fantasy and was she about to call a halt to his sexy birthday adventure.

"What's the matter?" he asked her.

"Oh, nothing really, but I was just thinking. Is this all you want to do, check my VPL?"

Paul was hoping that it would lead to a lot more, but he'd play along for now.