Spy Games Ch. 02

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Boris the pickpocket / Amanda the actress.
6.5k words
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Part 2 of the 26 part series

Updated 06/12/2023
Created 03/22/2022
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Aaroneous
Aaroneous
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My dream of spending my last three days under my parent's roof boning my new tutor twice a day didn't happen. Instead, Mrs. Bancroft told me to read.

"Read what?" I asked. "I've already read all the American, British and Russian classics... to include War and Peace."

"I'm sure you have. Now it is time to expand your education. We'll start with some Harlequin novels."

"Harlequin? The romance novels? Aren't they for women?"

"They are. And that's why you will read them. There's been thousands published, but they're pretty much all the same. Once you've read a dozen or so, you've read them all."

"If they're all the same, why do women read them?"

"Because they describe the lives women want to live. The books are their escape from reality. You give a woman a Harlequin experience and she will do whatever you ask."

Mrs. B was right. After reading three of the romance novels, I knew exactly what would happen in the fourth and fifth and twelfth. But there was something missing. Sex. If they were movies, they would be rated G and currently shown on the Hallmark channel. That's when she introduced me to the next level. The erotic romance novel... what would later be labeled "Mommy porn". The plots were still the same -- beautiful woman meets handsome man, and they live happily ever after -- but the words changed.

In the romance novels, the leading man rode off into the sunset while the woman patiently waited for his return. In woman's erotica, he rode the leading lady bare back from sundown to sunup. "My lonesome lips yearned for his tender kiss" was replaced with "My wanton pussy yearned for his rock-hard cock."

"Pay attention to what a woman reads young prince," Mrs. Bancroft said. "What she reads is what she wants."

***

I didn't get another true sex lesson from Mrs. Bancroft until three days after our first encounter. We had just moved into a spacious three-bedroom flat located in one of Moscow's more affluent suburbs. I personally moved my stuff and her clothes out of my parent's house and into the large apartment while a moving company brought in the bulk of her possessions... to include one queen and one king sized bed. Yes, to my chagrin it appeared we would sleep in separate rooms.

That evening, she called me into her bedroom and again had me undress her. But when I started to remove my shirt, she said...

"Before we get to that, you have a few more things to learn. A doctor isn't taught to do surgery until he passes a basic anatomy course. Now sit on the bed and pay attention. The more you learn about a woman's body, the easier it will be to pleasure it."

I'll be damned if she didn't launch into a detailed lecture on her mommy parts. Stark naked. I mean, I got the standard "birds and bees" talk from Mom when I was thirteen, but Mom didn't use visual aids and it certainly wasn't a hands-on lesson.

"Doctors call these bits down here the labia majora or the outer lips," Mrs. B said as she lay next to me on the bed. "They're usually covered with hair but I, like many other women, prefer to keep them shaved. As I spread them apart, we see the inner lips. Go ahead, give them a feel but be gentle. As much as a woman may want you to play down there, you have to warm her up first. Now, if you open up the lower lips..."

It was an hour-long lecture. She started with her pussy and then had me run my hands over every square inch of her body as she explained how different women liked to be stroked in different places. At her request, I spent an inordinate amount of time massaging her feet, rubbing the crease of skin behind her knees and then fondling her nipples. After giving her left nip one last tweak, she brought my attention back to her pussy.

"Do you notice any differences in my outer labia lips between now and when we first started?"

"They uh... they're sticking out. They seem to be bigger."

"Good. And why do you think my pussy grew in the last hour?"

"I'm not sure," I admitted.

"I'll give you a hint. Why is your penis twice as long now than before we started this lesson?"

"Because I'm turned on?"

"Exactly. Blood flows to your penis to make it ready for sex and a similar thing happens to my body when it is aroused."

"You're aroused?"

"Of course I am. A handsome young man just spent the better part of an hour running his hands over my most sensitive erogenous zones. Put your fingers down there and feel how moist my pussy is."

I complied and confirmed that she was definitely damp.

"Remember when we talked about the g-spot? Reach into my pus with your two middle fingers and caress it like we talked about."

Mom always said I had piano hands... long thick fingers that could easily stretch across a keyboard to tickle the ivories. I never had the urge to play piano, but I finally found a use for my larger than normal fingers. Mrs. Bancroft let out a slight yelp when I buried my oversized digits in her slender snatch and fumbled around for the mystical rough patch of interior membrane that, when stroked, would allegedly turn a normal woman into a screaming nymphomaniac.

It didn't work. I'm fairly sure I found the right spot. It was bumpy and in the right place, but when I gave it several strokes, Mrs. B. didn't start moaning in ecstasy. Instead, she gave me an annoyed look and said...

"Did you think it would be that easy? Hopefully you don't believe one little tickle inside my vagina will set me on fire. No, my young prince. If you want to elicit an orgasm from a lady, you will have to work for it. Now keep those fingers inside of me and stroke my G spot like you are beckoning me from across the room. That's right, tell my body you want me to cum. I know I initially told you to be gentle, but we're past that now. Give me a good rub. Don't worry, you're not going to hurt me. My pussy is built tough, it's designed to birth babies."

So, I spent the next couple of minutes doing finger exercises and, sure enough, what once was a slightly wet pussy was turning into a river of lady lube. As I continued my ministrations, Mrs. B reached down with one hand and placed my right thumb on her clit. Then her other hand grabbed my left and moved it to her breasts. And that's how I brought my first woman to an orgasm.

It wasn't a powerful event. She didn't scream out in joy praising the day I was born. Her hips didn't buck my hands off her body. And she certainly didn't pass out from an overload of pleasure. But she came.

At least I think she did. Although I had been mistaken before. Whatever happened, the lesson was obviously over. Mrs. B extricated herself from my double handed grasp, climbed off the bed, and put on a robe.

She must have seen the doubt in my face. "Yes. I experienced an orgasm," she said. "Not a rip-roaring experience, but an orgasm just the same. In subsequent lessons, you'll learn to distinguish between the real thing and a good acting job. But be satisfied that, on this night, you pleasured a woman using only your hands. Now get yourself to bed. We have a busy day planned for tomorrow."

"That's it?" I asked. "We're done for the night?"

"Do you have a hearing problem? Isn't that what I just said?"

"No ma'am. I heard you but uh... I thought..."

"You thought what? That it was my turn to pleasure you?"

"Well... uh... I was hoping so." From the size of the bulge in my pants it should have been obvious that I was in serious pain. I had a boner that stretched down my left pant leg almost to the knee. I was so stiff I could barely stand upright.

"Listen young prince. Among my many other Company duties, I am tasked to teach you how to woo women... how to convince an unsuspecting female to do something she otherwise wouldn't. But I am under no obligation to ensure your own sexual satisfaction. However, there is merit in building up your stamina.

"Do you enjoy playing games?" she asked after a brief pause.

"I do. My parents and I play all sorts of games."

"Well probably not the sort you and I shall play tonight. But before I explain the rules, we must settle on a prize."

I not only didn't know what kind of game she had in mind; I didn't have a clue as to what type of prize she was considering. So, I did the smart thing and said nothing.

"Dishes," she finally said after several moments of contemplation. "Whoever loses does the dinner dishes the next evening."

"That sounds fair... but what's the game?"

"It's the game of endurance. We will make love to each other every night and whoever comes first is the loser."

It wasn't a fair competition. I was harder than a German Shepard at a Poodle show, and she had already come once just prior to our agreement. My oversized cock spent less than ten minutes between her boobs before I committed to kitchen patrol the next day. But I didn't feel like a loser. Most eighteen-year-old boys would clean a thousand plates in exchange for one night with my sexy mentor. I had an entire year to improve my game.

***

When I woke that first morning in Mrs. Bancroft's apartment, I lay in bed wondering if the events of the previous night had been a wet dream or if Mrs. B really said we'd have sex every night for a year. Realizing it was the real deal, I was a very happy teenager when I came downstairs for breakfast in a t-shirt and sweats.

"Why aren't you dressed?" Mrs. B asked in the accusing way adults must learn after turning thirty.

"For what?"

"Your new job."

"I have a job?"

"It's an internship actually. You certainly don't expect to spend your days lazing around my flat do you?"

"No, but I thought we would spend our days doing the mentoring thing. You know, teaching me about women."

"We will, as time permits. But taking you on as a ward does not relieve me of my primary duties with the Company. I still have to put in a full day at the office. And remember that I am not tutoring you to seduce women for your pleasure. My mission is to train you for service to your country. Now get your butt back upstairs and put on some appropriate clothes."

Wow! Mrs. B is definitely not a morning person. I think I like the nighttime, 'come fuck me' Mrs. B a lot better than the pre-breakfast, get your ass to work version.

Since I didn't know what type of work I'd be doing, I had no idea what would be appropriate to wear. Taking no chances, I changed into a coat and tie, ate a rushed breakfast, and walked with Mrs. B to the subway. After riding three different trains and two public busses, we ended up at the back door of an unmarked shop in one of the shabbier neighborhoods of Moscow.

As it turns out, I was grossly overdressed for my first day of work... as an apprentice locksmith. I was to spend three mornings a week learning how to install, fix and... most importantly... pick every type of lock known to man.

The following morning a different circuitous route took us to a firm that installed and maintained electronic security systems. Because what was the use of knowing how to pick locks if I didn't know how to disable the alarms? Apparently, I was being trained to be a burglar.

On the third day we ended up in the business district of yet another Moscow suburb. Mrs. B led me to a café where we sat at a table and ordered coffee.

"Is this my next internship?" I asked. "Am I also to learn how to serve food?"

"Not a bad idea," she said. "Some of our best information comes from waiters and waitresses. But we are here to meet your third and final tutor. He is sitting behind you but don't turn around. You can see his reflection in the mirror over the bar."

"The man in the suit by the window or the rough looking guy sitting in the corner?" I asked.

"The gentleman in the corner. In a few minutes, he will leave the restaurant and walk down the street to the right. When he does, you will follow him."

"Okay. And then what?"

"He will lead you to his place of business and you will learn?"

"Learn what?"

"Something you desperately need to know."

A cup of coffee later -- during which Mrs. B gave me a crash course on how to tail somebody without being discovered -- I followed a middle-aged man wearing a nondescript overcoat into what appeared to be an abandoned warehouse. Complying with Mrs. B's instructions, I stayed a good hundred feet behind the mystery tutor the entire time.

When I opened the warehouse door and stepped into the dark interior, it was like I had taken the first step into my future life. As soon as the door shut behind me, a bright light shone into my face making it impossible to see who held it.

"Are you the one the woman sent?" a voice asked with a working-class Moscow accent.

"I guess I am," I said, trying my best to not sound like the privileged, overly educated boy I was.

"She says you have a problem with buttons."

"Buttons?"

"And zippers, and snaps and bra straps. How do you expect to get laid if you can't even undress the girl?"

The man laughed and turned his flashlight towards a wall switch. "Turn on the lights so you can see my classroom."

I flipped the switch and almost jumped out of my skin. As the overhead lights slowly flickered to life, I saw a room full of body parts... mostly torsos without arms, legs or heads. But as my eyes adjusted and the lights came full on, I discovered I was in a warehouse full of mannequins... the plastic dummies clothing stores use to display their wares.

"I am Boris," the man said. "And this is my assistant Natasha" He wrapped his arm around one of the bustier mannequins. "You two should get to know each other, you will be dressing and undressing her a hundred times today."

It took a while before I got to a hundred. Boris was a stickler for detail. I guess you had to be in his line of work. He was the premier pick pocket of Moscow. A legend in the criminal world and even the local police respected his skills. He'd been in the business for over thirty years and had never been caught. Now retired, he agreed to help me learn the finer points of undressing a woman. Mrs. B was assuming that the skills required to clandestinely unbutton a man's coat to get to the wallet hidden inside were the same needed to smoothly unbutton a woman's blouse to get to the treasure within.

We started with large buttons on loose fitting blouses. Boris showed me his techniques and I practiced... hour after hour. Once I could expose Natasha's plastic breasts without ringing the tiny bells attached to her sleeves, the buttons got smaller and the blouses tighter. After a couple of weeks, Boris threw zippers and snaps into the mix. It was over a month before I mastered how to unhook Natasha's bra without ringing the bells.

That's what I did for the next three months while Mrs. B. was at work. I learned how to pick locks, bypass alarm systems and remove clothes from storefront mannequins. In the evenings and weekends, I was introduced to many more and different ways to bring my mentor to an orgasm... with my pants on.

The highlight of my week was Saturday night, when we played a game Mrs. B affectionately called, "first to cum serves." A variation of the first bedroom game we played, this was a no holds barred, cock free contest to see who could make the other cum first... with the loser serving the winner breakfast in bed the following morning.

I got extremely proficient in frying eggs and making coffee.

***

London.

Four months into my internship, Mrs. Bancroft was transferred to the US embassy in London and took me with her. I considered staying in Moscow with my parents, but when they announced that they too were being reassigned, staying with Mrs. B seemed the right move.

I never knew what Mrs. B did for the Company, but whatever it was, she obviously took a step up the pay scale with her new job. London, at the time, was one of the most expensive cities in the world. The monthly rent on her three-bedroom Kensington condo cost more than most people made in a year. The Company apparently thought her presence close to the high and mighty of London society was worth the price because Mrs. B's compensation package included, not only our lodging, but also a live-in maid.

Amanda Zimmerman, a twenty-year-old actress trying to break her way onto the London stage, was our first part time domestic. The servant's quarters, which consisted of a small bedroom with attached bath, were on the third floor of our three-floor condo. As usual, I got stuck helping Amanda carry her considerable wardrobe up the stairs.

"You've got thirty days to discover her secret," Mrs. B told me when Amanda wasn't in the room.

"She has a secret?"

"All women have secrets. But Amanda has one that only she and I know. You have until the end of the month to find out what it is."

"What happens at the end of the month?"

"We get a new maid."

"I don't understand.

"Figure out her secret and you will."

This might be a good time to review my experience with the opposite sex at the time in question. Thanks to Mrs. Bancroft's tutelage, I knew how to consistently bring a thirty-six-year-old woman to a rip-roaring orgasm if -- and I must emphasize the "if" -- she invited me into her bedroom and willingly let me remove her clothes. However, I had absolutely no idea how to transition from the "Hi, glad to meet you" phase of a relationship to the "Please let me ravish your body" level of intimacy.

To make my situation even worse, thanks to my overly protective up bringing, I had never in my life had more than a ten-minute conversation with a girl my age.

I wasted three days rehearsing different conversation starters that I hoped would eventually lead to a discussion of her deep dark secret only to get shot down every time with Amanda's one- or two-word answers to my well-crafted opening lines. After my twelfth unsuccessful attempt at making an inroad into the mysterious girl's inner thoughts, I finally admitted defeat and went to Mrs. B with the age-old question most boys ponder.

"How do I get her to talk to me?"

She laughed and asked me what I'd tried so far.

I repeated a couple of the thought provoking questions I'd asked the girl and Mrs. B laughed again, only harder.

"What's so funny?"

"Did you really ask her opinion of Melville's relationship with the whale?"

"I was going to use the story to transition to hidden meanings."

"And when that didn't work, you wanted to discuss the merits of the Sig Sauer versus the Glock?"

"Okay, I know that might have been a stretch..."

My lame excuse was interrupted when Mrs. B drew me in for a kiss.

"Listen my young prince. Girls Amanda's age will not be impressed by your knowledge of American literature or experience with firearms. Don't try to impress her. Let her know she impresses you."

"How?"

"Spend time with her. Listen to what she says. Acknowledge her worth and she'll eventually realize that you are an intelligent, good looking young man who is worth her time and attention."

"But how do I get her to hang out with me?"

"I've already taken care of that. Starting tomorrow, you will be her assistant. You are to help her with the shopping and cooking."

***

Our move to London did not make my life any easier. I soon had advanced internships with security companies, safe crackers and Mrs. B found an English replacement for Boris the pick pocket instructor. Now that we were back in relatively friendly territory, she also arranged for me to get some no-shit military weapons training plus tutoring in what they called "unarmed combat"... which essentially gave a UK special forces guy carte blanche to beat the crap out me twice a week until I learned how to defend myself. Not that I was complaining but, after a full day at the office, I was still attending Mrs. B's how-to-seduce-a-woman night school.

My point is, I didn't have time to take Amanda shopping and certainly didn't relish being her sous chef. My year of training under Mrs. Bancroft was starting to feel more like some crazy social experiment gone horribly wrong. But I didn't have much choice. I lived in her house, she paid the bills, and I had no idea where my parents were. "On a mission", was all Mrs. B would tell me when I asked.

Aaroneous
Aaroneous
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