Gary the Obscure

She spat on to her other hand and spread that as lube on Gary's recovering dick.

"Oooh it's so large tonight."

He then thought so too. It felt as if the head was about to blow off under pressure.

They were on the back seat and Madison spread her legs like a champ and steered Gary in.

"Is that in far enough?"

"No the tip is only just in," she replied, sounding tense.

"How about that?"

"No more. You are supposed to go all the way in."

"What?" he asked in surprise. "I thought that applied only after the first time."

"Well I don't know and actually I don't care if it's wrong. It just feel like having it all up me and for me to hold you."

"Why do you want to hold me?"

"I don't know. Please get on with it Gary."

"What if it hurts?"

"I imagine I'll tell you."

A few moments later Gary said, "God you are leaking badly."

"Just push back in and stop fretting Gary. It's supposed to be an all-natural act."

That settled Gary and he was away. He'd chatted with his pals about sex but they'd never got down to details. The consensus was just push it in and bang away and remember to push into the right hole, and other irrelevant stuff like which of their teachers, er females, would be the best fuck and was it a good idea to have a try-out with one's older sister.

Gary plowed on and remembered all too briefly the great welling inside him, giving the feeling of being on top of the world, when he was hearing her screaming 'Oh glory, oh glory."

He exploded into her.

Madison looked at him with stars in her eyes and she saw him looking dumbly at the small packet in his hand.

"I forgot to put it on," he groaned.

She patted his shoulder and said it didn't matter, that she had been on the pill for a year.

"Confirm to me you haven't had your penis inside any female?"

"Yes that's true," he mumbled. "It's not been in any female or any male for that matter."

"Oh yuck," Madison winced.

She called him next day before leaving for the airport and said she felt she a little sore but was feeling glorious. How are you?"

"I feel something. Perhaps I feel manly."

"Oooh and I did that to you? Oh that's the power of women."

Then her dad yelled and she had to go.

"Goodbye my lover," she said softly and he said awkwardly to travel safely and the call ended.

Another eight years would pass before they talked again and arranged to meet. They went to different colleges, three hundred miles apart.

* * *

Sex was never far from Gary's mind that summer and it seemed about one in every four or five female former classmates he met was similarly preoccupied with sex. Annie was understanding and talked to him about sex hygiene and kept him supplied with condoms.

The one encounter he'd never forget was Jennifer Borland's mother.

Jennifer had called Gary a couple of days earlier and suggested they hire a kayak and paddle upriver for a few miles and have a picnic in a clearing in the woods. Gary thought he knew what she had in mind. But when he called for Jennifer it appeared no one was home.

He went around the house to check the pool and found Mrs Borland there alone, sitting beside the pool fully dressed and reading a magazine.

She looked up and smiled, recognizing Gary because he and Jennifer and hung out with the same group for a couple of years or so.

"Oh hi. Jennifer called didn't she?"

"No."

"God she can be so irresponsible."

Mrs Borland was on a sun lounger and saw Gary looking at her legs and quietly pulled her hem down towards her knees, looking away from him.

He colored and thought she had great legs for an old woman.

"Jennifer's father wanted her to go with him to visit his parents. She went meekly and muttered something about calling you about your date later this morning."

"It's okay. Perhaps her dad pushed her to get away."

"Go fetch a cold drink for yourself Gary and pour a coffee for me darling."

He returned with the drinks to find Mrs Borland had disappeared.

"Over here in in the shade," she called, reclining on another lounger.

Gary noticed her skirt was up higher than before.

He handed her the coffee and she smiled and said he was a fine-looking boy.

"Have you had sex with Jennifer?"

"No not yet, um I mean no."

"Are you sexually active Gary?"

He hung his head and muttered should they be talking like this and she didn't reply.

Gary sat facing her sipping his soda and couldn't believe it when Mrs Borland raised her leg and he could see her white panties.

He stared and she stared at him.

"Do you find me reasonably attractive Gary?"

He nodded and said she had great legs.

"How far up do my legs go Gary?"

He mumbled to her hips.

"Oh I expected you to say to my pussy."

"I should go."

Mrs Borland swung her legs to the ground and sat up.

"Do you really wish to go or should we go inside?"

Gary made the mistake at glancing toward the house and Mrs Borland jumped him and pulling him to his feet said, "Please don't be shy Gary, this is just um experimental."

"Experimental?"

"Yes I wish to bring myself up to date by examining a young man's penis."

"You do?"

Another mistake; he replied instead of fleeing.

"Yes Gary," she said, grabbing his butt and squeezing. "Come with me. No one will ever know."

Once Mrs Borland had stripped for Gary he saw she didn't have a hair on her body apart from head hair.

Her tits were large a hung down. She waggled them for him and his efforts to keep his dick from advancing beyond the half-erect stage collapsed. It went rock hard and strained to get inside Mrs Borland.

He undressed frantically and she smiled at him and held out a condom as he moved towards her.

"I only suck a dick if it's in a condom darling and then you can enjoy anal sex. I only engaged in anal sex when I commit adultery. My husband is entitled to believe my pussy is his but you may play with it."

"Yes Mrs Borland."

"Call me Christine darling."

Christine made Gary bang her four times and she got herself off each time.

Gary left at 3:30, a very weary guy

"Please don't fuck Jennifer anally Gary. She's too young for that yet."

"Right Christine. I'll never forget this day."

Mrs Borland looked very pleased.

CHAPTER 2

Gary went to Annie's old college when they found it was particularly strong on computer education. He knew he'd know no one there and would feel like an alien.

"You came to us as Gary the Obscure, knowing only Hogan and me in our community and now look at all those people you know in this city. Darling may I ask you something very intimate?"

"Sure shoot," Gary remembered saying and Annie had asked, "Have you had sex with Mrs Borland? I had coffee with her the other day and she made a comment that made me wonder."

"Jennifer wasn't home when I called and I have to say I fell under the seductive charms of her mother."

"Yes well she has a reputation for being promiscuous. Did you wear a condom?"

"Yes."

"Good boy."

And that was it. His mother now knew something Gary hadn't wanted her to know. He'd been seduced again by an older woman. God they could be so crafty.

* * *

Gary graduated in the top five percent of his class with a Masters in Computer Graphics and Motion Technology. His adoptive parents attended the commencement and met many of his friends. Although Gary had invited his birth parents to attend neither had replied to the invitations sent to their last known addresses. He was sad about that but sensible enough to know he should continue moving on.

A month prior to graduation he was invited to interview for a position with a large advertising company that had several clients that advertised heavily on TV, an area in which he desired to specialize. He was supplied air tickets and overnight accommodation to appear before the interview panel and was dismayed to find he would work at the tail-end of a line of people, being regarded as a junior who would be promoted in due course to his appropriate level.

Gary wanted to be regarded and assessed as an individual specialist rather than like a digit on the payroll. He believed the chain of command in place was inappropriate in that it would stifle original thought and enthusiasm. Two days later he called back and said he would only be interested in working as a senior graphic artist and the reply was corporation had no further interest in him.

Fair enough.

He left college without a job and his mom said she was going to London to a reunion with some of her old college friends now spread around the world and he could accompany her if he wished.

"Um I'm squeezed for money."

"I'm not," Annie said. "Your father is involved in a battle to win the design contract of a big civic project and can't come with me."

"Can I think about it?"

"I'd have to call the travel agent right now to..."

"Okay, I'll go. Thanks for the offer and your generosity. I'll happily escort you to events and try not to seduce your friends and their daughters."

"What about me?"

"It's funny you should ask that because..."

"Gary, don't be so disgusting."

Gary scratched his ear as the call ended wondering if his mother really had been disgusted at what she thought he was about to say or was she practically palpitating in excitement? It was difficult to tell with women.

Annie called an hour later to advise her flight was full but she'd booked Gary on a flight they would leave eight hours later.

"That's fine. I'm lucky to be going."

"You are lucky I'm still talking to you," she snorted. "We are looking forward to joining you in two weeks to see you honored."

Ah she was referring to $1000 prize he'd won earlier in the academic year by submitting the regional TV advertising campaign the university used for recruitment of students for the following year. A thousand bucks was peanuts compared with the boost that project gave Gary in his career ambitions and it would count as a gold star on his CV.

* * *

The Smarts would be staying in London with Louise and David Copeland. Louise and Annie had been best friends at high school and had gone through college together. Their daughter had been sent to Heathrow to collect Gary who was arriving eight hours after his mother, or actually more than nine hours later because of delays.

Philippa held up a notice 'Gary Gunn' and watched a curly-headed blond guy walking towards her and either reading the notice or focusing on her breasts and she almost dropped the notice when realizing he was grinning and walking straight at her.

"Mrs Copeland?"

Philippa was momentarily confused by that and then squeaked, "No I'm mom's daughter er Philippa."

"Oh hi Philippa. I'm Gary or Gary the Obscure as mom sometimes refers to me. Do we kiss?"

Not wishing to squeak, Philippa held out her face to be kiss and had a wet one planted straight on her lips.

Her knees almost buckled and she thought this guy was anything but obscure.

He went to pull out after the kiss but his hazel eyes bored into her green ones and he leaned back and gently licked her top lip.

Yes licked it!

Philippa thought he could have her and then thought god how disgusting to be licked by a stranger like that. She really didn't know what to think and said, "Nice flight?"

"It was okay."

He was looking at her breasts. She went to straighten her back to pull them back in but the wrong signals was transmitted by her brain and they pushed out, just a little thank god.

"Mom said you were a third year fine arts student."

"Yes, I wish to specialize in portraiture."

"Have you done a self-nude painting?"

"What? Heavens no."

"What about just of your tits?"

She stepped back from him and glared. "Would you please get your mind above your belt."

"Okay, if he can," he grinned. "Here please carry my laptop and take me to bag pickup."

Philippa smiled when he returned with a large soft bag.

"You may have to nurse that."

"Why have you been out shopping?"

"No," she said looking perplexed.

"I meant was the vehicle full of your shopping."

"Oh no," Philippa laughed. "It's what you might call a toy car."

They stood looking at the red toy car.

"What is it?"

"A recent fully restore 1975 Jensen Healey Roadster 5-speed, mom's pride and joy. She had taken her weekday car to take your mother to meet some of the girls."

"On that's nice. So you have sisters?"

"Only one and she lives in South Africa. By girls I mean other women who are here for the reunion."

"Can I drive?"

"No. Only mom and dad and I are registered as drivers with the insurance company."

The family lived in a big apartment in a place called South Kensington.

"We are an easy walk to Kensington Gardens from here, one of the Royal Parks of London covering 275-acres and it's an extension of Hyde Park."

"Oh."

"I meant if you run. It's open ground but the gardens are only open in daylight hours."

"Do you run?"

"Yes."

"Then so do I."

Philippa said actually that was no surprise because he looked very fit.

"So you have been studying my body?"

She looked away blushing.

Gary pressed in hard. "You appear uncomfortable with me?"

She hesitated and said he was very direct.

"Do you have a boyfriend?"

"Yes and that's what I mean by very direct."

He said if he waited for her to tell him that he might have had a long wait.

"He's in Scotland at present and yes I will go out with you as it's the polite thing to do."

Gary said there was no need to be overly polite with him.

"If you don't want me being polite then how should I be?" she replied but seeing his expression said, "No please don't answer that."

They laughed.

Philippa led Gary into one of the ornately decorated reception rooms.

"Wow? Did the Queen live here once? You parents must be loaded."

"They have money to spend if that's what you mean. Mom is a consulting pediatric surgeon and dad is a structural engineer, the senior partner in a large practice."

They moved into the kitchen for tea and Gary asked for coffee and Philippa laughed and said oh yes, that she'd have coffee too.

"Do you want to go to bed now after your tiring flight?"

"What if you mom comes home early and catches us?"

Philippa just turned her head from side to side and sighed as if dealing with a pathetic child.

"I'm not really tired. I had a drink at the airport and another couple of quick ones early after take-off and slept in bliss. Can we go somewhere?"

"Where?"

"For a run in the park?"

At the magnificent park Philippa filled Gary in about its history and yes he knew of Peter Pan when they saw the statue, Prince Albert (when they ran by the Albert Memorial) and Diana Princess of Wales (when they saw the memorial playground named after her and Philippa said Princess Diana after her divorce continued living in an apartment on the north side of Kensington Palace until her death).

He was most impressed.

They returned to the apartment, showered (separately) and leaving a note that Gary had arrived safely although ninety-minutes late, they went by Tube (underground train) to Piccadilly Circus and walked for hours looking at the sites and visiting places.

Philippa's mom called her to check they were okay. They were standing in front of a shop window looking at scale models to assembly and she moved away when she saw who was calling.

"Mom he's gorgeous."

"Lucky you. What do you intend doing with him?"

"I won't embarrass you by saying."

He mom laughed and said they would eat out locally and agreed on a booking time of 9:00.

"That was mom checking that we were okay."

"Well she's a good mom even if you are an adult. Did she ask you what I was like?"

"N-no, I-I m-mean yes."

"It's okay. You want to learn to relax around me. Here give me a kiss."

Philippa forgot they were on a very busy shopping street. She closed her eyes and the kiss just consumed them until he pulled away and said, "You kiss brilliantly."

Glowing, she smiled at him and checked her lips and the long-lasting covering was fine. She then couldn't help it. She took his hand and squeezed it and felt so happy when he wiped back her straying black fringe with his hand.

"Should we book into a hotel for a couple of hours?"

She replied she didn't know the location of that kind of hotel l and anyway they'd only be ripped off. She said to be patient, he could go to her room and hour after they returned home from dinner.

"You'll be sleep."

"That's very unlikely."

But at dinner her father ordered champagne and they drank two bottles plus a bottle of magnificent but very high-alcohol red wine and the apartment had been vacated by the time Philippa awoke in the morning, sad she'd missed an opportunity

She found a note from her mother, 'We're off to Harrods to meet everyone and we will lunch there. Behave now darling. Treat him gently as he's very sweet. Remember we need Gary tonight to partner Annie to our group formal dinner. We are booked for twenty'.

Philippa grabbed a couple of condoms and went to Gary's room, removed her night-shirt and slipped in beside him. She felt around and gasped excitedly, snaring a boner of good proportions in her fist.

He awoke.

"God it's you. I seem to smell your freshness before I awoke and thought my dick had gone to heaven."

"It's only in my hand."

"You can improve on that I would think?"

She giggled and throwing the bedclothes right off licked his dick wet and then climbed on to him and began pushing it in.

"Condom."

"Oh thanks," she gasped, and started from scratch again after rolling the membrane over the ugly purple head of his dick and down almost to his balls, noticing the absence of hair.

Philippa hung her tongue out the corner of her mouth when sitting astride, facing him, and slowly lowering on to his prong and gasping as he reached up and squeezed her boobs.

The 20-year old thought she was in for a great fuck and in time found her expectations had been exceeded.

They fucked five times that day, slept twice, snacked three times and they got up mid-afternoon and Philippa turned the air cycling option on the air-conditioning unit full on and changed the sheets in Gary's room.

"I've only seen these wall paintings as examples of your art. Do you have portfolios to show me?"

"Yep I'll get them."

Philippa waited impatiently for his comment and finally went off and switched on TV.

Gary arrived with coffee.

"Well?"

"It's the first time I've ever seen an artist's work stretching back to when they were three."

"My recent work, I want to know what you think?"

"Well you might not welcome what I could say."

"Gary give me your honest appraisal or I shall scream."

"God your tits look great even when you're dressed."

"Gary!"

He held up a hand and said all right, all right.

"Switch your focus from portraiture."

She wailed, "Oh no, not you too. Two of my senior lecturers have told me the same thing. They say unless you are brilliant in portraiture you can kiss a good career goodbye."

"I'd agree with that. You could think about specializing in wildlife painting. I think you already excel at that. Those three seagulls circling overhead to me appear brilliant and must have involved very hard work in getting everything just right as you have done. The two ducks landing on that pond, done in oils and expensively framed, would bring big money and your cat is one of the best animal paintings I've seen by a student and you must have been told that."

"Well yes."

"You would have a choice of career paths... paint and try-to-sell, door-knock and advertise for commissions or to seek to illustrate publications."