Mason The Masseur: The Beginning

To the readers, as you read the story, you'll notice that I've never finished high school, so if my writing is not up to par, bear with me...

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Hello, my name is Al. I am 33 years old, 6' tall and 178lbs. I was born in the USA to parents who emigrated from Scotland. I am not married and as far as I know, no children yet.

My life story was normal until the age of 17.

Then an unfortunate accident at work turned out to be fatal for my father, who was the bread winner for our family.

After his death the compensation from his work was very low (The company claimed that his injuries happened as a direct result of his negligence...) and his life insurance turned up to be inadequate.

Mom was an excellent mother and a cook, but she never worked outside the house.

In fact, she didn't even drive or knew how to use a computer.

My older sister was in her 1st year in college and the younger one just started high school.

As a result of losing our only source of revenue, I had to quit high school and look for a job.

It wasn't easy to find good jobs, especially for somebody who was a minor and didn't finish high school.

After several weeks of search, a guy who owned a small construction company accepted me on one condition. I wasn't supposed to say that I was a minor. I worked my ass off and earned OK money, but it was much less than what our family was used to have when dad was alive.

Until my 18th birthday most of my time was dedicated to hard physical work. Subsequently my muscles developed nicely.

Since I spent my days with other construction workers who were all men, I wasn't concerned or aware of my looks.

On my birthday my older sister came from college after several months that she hasn't seen me.

"Al, you are so tall and handsome! I bet girls are all over you all the time..."

I blushed and remained silent.

"What is going on? Are you too shy to tell us about your free time adventures?..."

"Sheila, stop bothering Al! Isn't it enough that his salary supports your college tuition? Be nice to him, please," mom was annoyed.

"Mom, Al is a young attractive man. Are you telling me that he never get's to go out with girls?!..."

Mom stayed mum.

"Al, on Saturday you are going with me and my friend Barbara to a club. I want you to see that there is life beyond work!..."

All my life Sheila was my idol. She was older, smarter and... very pretty.

At home, before she went to college, many friends both girls and boys visited her frequently. I adored her.

Sheila was always nice to me and earlier in life she helped me in school homework too.

I interpreted her current inquiry about my personal relationships as pure curiosity and trying to help. But I didn't answer, because I had none...

I wasn't sure about going to a club, but I didn't wish to argue, so I agreed to go.

Saturday night Sheila drove us to pick up Barbara, who I have never met before.

"Hey Sheila, who's the stud? I thought that you and I go together... You know that I hate to be a third wheel!..."

"Oh shut up Barb, this is my younger brother Al. It's time for him to learn that there is more to life than work!"

"Sheila, if he is not engaged yet, can I have him? Please..."

My face was crimson red.

"Sheila, he is blushing! He is so cute... I love him from first sight! Al dear, if you are interested, remember me, I am and always be available for you."

Sheila had a big laugh. Was Barbara really interested or she was picking on me?...

We arrived and saw many people, mostly young ones near the door.

Sheila approached one of the guards and talked to him. After a short discussion he let us in.

Being first time in a club was overwhelming. The noise, the colored lights, the deafening music, such a loud crowd...

Sheila tried to talk to me, "Al, I'll be here. Why don't you walk around and watch the people. You may find somebody interesting to talk to. You look especially nice this evening, so you might encounter an attractive girl. Is it OK? If you are bored, you can come here and stay with Barb and me."

I hesitated. Everything was very new and mind-boggling. I was confused.

But then I decided that I had nothing to lose, so I agreed to walk around.

I started moving among the crowd, simply watching the large number of guests.

Some girls stared at me and smiled. Was it a sign of 'hello'? were they interested?

I didn't feel confident enough to approach them.

I needed to pee. On my way there a lady touched my shoulder.

She was about 5'8" tall, fairly pretty and looked to be around 35 to 40 years old.

"Can I talk to you? I have a proposition for you. If you are interested, let me know." And then she gave me a card that said 'Holly Jeffries productions'. Her phone number and e-mail were attached.

I smiled at her, put the card in my pocket and went to the bathroom, forgetting all about it.

The rest of the evening I met 2 girls that were my age or slightly younger. I chatted with both, but I wasn't educated or sophisticated enough to find common subjects to talk about.

Another girl, around 25 years old was more direct. "Hi big guy. I haven't seen you here before. I like you. Would you like to get some fresh air? Or better still... have a night cap at your home?..."

She was attractive , but too aggressive. I smiled and didn't bother answering.

After about an hour I joined Sheila, "Where is Barbara?"

"She is dancing with an older guy. She signaled to me that she'd be with him, so I could leave her here. Do you want to go back home?"

"Sheila, I hate to ruin your plans. I could sit here and wait for you until YOU wish to go back..."

"Oh nonsense, I am tired too. I danced with few guys and even kissed one of them, but neither clicked with me. If you are ready, we can leave."

Less than an hour later I was brushing my teeth and getting ready to go to sleep.

I removed the stuff from my pockets and found Holly's card. I left it on my dresser.

After a dreamless night I woke up at 9 am, happy that I didn't have to go to work.

I noticed the card again and decided to call and find out what was the lady's offer.

She answered by the 4th ring, "Hello, who is it?"

"This is Al. You gave me your card last night at the club..."

"Oh, yes! Listen, why don't you meet me for lunch at Spago's, let's say 12:30?"

"Ma'am, I'd love to, but I can't afford it and I have no intention to be embarrassed there..."

Her laugh was pleasant, "Al, you won't have to pay a dime. I have enough money. And since I invite you to lunch, everything is on me. OK?"

"Lady Holly, I'll be there on time."

"Great. Just do me a favor and call me Holly. Lady Holly sounds like a title of an old woman..."

I met her at the reception of the restaurant. She smiled and led me to a quiet corner table.

She inquired me about my life and work. Then she looked me in the eye and asked, "Are you happy with your life or you want more?"

"Holly, of course I'd like to do something that is less physically demanding and get more money..."

"Well, how would you like to earn at least 3 times your current salary, doing less demanding and much more pleasurable job. Of course, if you turn up to be good at it, additional bonuses will follow."

I got curious, "Does it have anything to do with killing somebody? Becoming a drug smuggler?"

She chuckled, 'No Al. The work is about escorting women to certain events or parties, being nice to them and courteous to the ones they meet. Some of the ladies may be interested in other services, but that will be up to you to agree or not. However, you'll be required to ALWAYS be polite, even if you decide to refuse their requests. What do you think?"

"Do I keep my current work too? How many days a week you want me? How many hours do I spend with the ladies? I do not have nice clothes to go to high society events..."

"Al, let's start slowly. You keep your job for now. I want you to go to Nordstrom Monday evening. At the men's clothes counter you'll find a woman by the name of Clare. Tell her that Holly sent you. She'll take care of you. By Saturday you'll have everything you need in order to meet me at 8 pm at my home address. We'll be going to a party at my friends. I want you to accompany me, smile when you can and try to be nice. Learn table manners and get used to these people's talk. Most of them try to impress others with their riches, business success, new expensive purchases and knowledge about everything. Gossip is always on the agenda as well. I expect you to listen and learn. If you have something smart to say that won't sound offensive, say it, but unless you are sure, being quiet and smiley is usually good enough to deflect attention..."

The next evening I went to Nordstrom. The lady heard the name Holly and rushed to take care of my needs. She took detailed measurements of everything, from my chest width to my shoe size. To cut the story short, three hours later I had 3 suits, 2 jackets, 5 new shirts, 2 sets of long pants with matching belts, 6 ties, 5 pairs of socks and 3 pairs of shoes...

After the shopping I ended up more tired than after a day's work... I slept like a log.

Saturday evening I showed up at Holly's house with my beat up Toyota Corolla. She looked at it... and let me in.

Her house was big and VERY luxurious, but I didn't have time to explore it.

Holly was ready 2 minutes later and led me to her BMW. She drove us for 20 minutes to another large mansion.

Another lady opened the door. They kissed and then Holly introduced me as 'My buddy Al'.

The other woman eyed me up and down quietly and turned back to Holly, "Good catch my dear. He looks like a good prospect!"

Then we sat at a long table that already had 8 other people around it.

Holly mentioned to me all their names, titles and professions, but I didn't remember much. I just smiled...

Waitresses in white uniforms served the meal as if we were in Louis the 14th court. Did I mention pompous?!...

I observed the way they ate, what utensils they used to what food, what type of wine was coupled with each meat & fish and LISTENED!

By the end of the night I shook the hands of the men and kissed the hands of the ladies.

When we got out, Holly seemed impressed, "Al, for your first time out you did extremely well. Here is a $1000. Now think carefully whether you are still interested. If the answer is 'yes', let me know and I'll see you again here at 6 pm next Saturday. However, next time it will be a different affair and your bonus will reflect it too..."

She kissed me on my cheek and disappeared into her house.

I was dizzy... $1000 for eating gourmet meal and doing absolutely nothing?... It was too good to be true...

I left a message on Holly's answering machine that I'll be there next Saturday as planned.

Next weekend I arrived to her house and was let in.

Holly told her maid to leave and only the two of us remained in the big place.

We sat on a loveseat in a magnificent living room. A bottle of wine was on the table.

Holly poured a full glass for both of us, smiled and said, "You need to get used to drinking wine. In our society the question is not if you drink alcohol, but WHAT you drink."

We chatted about my life story and about my work.

Every time my glass was about to be empty, she filled it to the rim again.

After emptying my second glass, I felt good and free. Holly was a good friend... She cared about me...

At one point she put her hand on mine and caressed it lightly. It felt good, so I smiled at her.

"Al, I like you... In fact I like you a lot!... I think we'll be able to work together in a way that both of us can enjoy..."

Her hand pulled mine and placed it around her shoulder, "Isn't it better for friends to sit like this?..."

Holly's perfume was intoxicating.

I glanced at her. Her face was definitely pretty. Her tits pushed her dress forward. The nipples protruded nicely...

I felt my dick beginning to grow.

Her hand was now on my thigh, trailing down and up, from my knee to my groin and back.

My prick expanded further and a tent became visible on my front.

Holly noticed it and whispered, "Al, that's OK! I can help you with that... Please kiss me..."

I was totally in the dark. With no prior experience, I had no clue what comes next...

I bent to her face and tried to kiss her cheek, but she turned toward me and our lips met.

It was a short, closed mouth kiss.

Then her hand pulled my face toward hers and she forced my lips open. My first French kiss.

Her hand found my bulge and lightly rubbed it.

It felt great! But I was afraid to cum in my pants..."Holly... if you are not careful..."

"Sshhh, beautiful boy. everything will be taken care off... I saw you ogling my boobs. Why don't you touch them?..."

My head was spinning. The alcohol... The pretty lady... My aching cock... It was all too much for me...

"Al, go to the bathroom, pee and clean up. You'll find me in my bedroom on the second floor..."

I went to the bathroom to realize that I really needed to pee. I took a short shower and wanted to think it over. Holly was offering herself to me... I wasn't sure what and how to do it. But she was pretty... and experienced... my cock was already pushing me to go ahead with it... and afterwards I'd get a bonus...

I couldn't think right!... Well, what the heck. I had nothing to lose...

I went to holly's bedroom.

She was naked under a thin sheet that showed all her curves...

My cock stirred again.

"Al, please undress and come here..."

I took off all my clothes and lied by her side. She took my hand and put it on her ample breast.

It was another first for me... It was soft, but with a very hard nipple.

Holly's palm found my erect pole, "My oh my! Your cock is a big one... And it salutes me already... Please kiss me again..."

I turned to her and kissed her luscious lips, this time inserting my tongue into her mouth, exploring her cavity.

She moaned and pulled my body above hers.

I removed the sheet, exposing her beautiful body. Her mature tits sagged somewhat but were perfect in my eyes. I sucked on her protruding nipples and she moaned again.

Her hand was pushing my cock toward her cunt.

I was to close to a climax and decided to postpone the penetration for now.

I crawled down on her body, reaching her pussy with my face in record time.

She smelled good. I licked her juices, getting used to the unusual taste... I inserted 2 fingers inside of her and licked her puffy clit. She gasped. Her pulse and breathing increased rapidly.

Suddenly her body jolted in the air and she began to cry...

Her snatch contracted on my fingers several times and her whole body convulsed from side to side.

Her cries gradually diminished and her body became limp in my arms.

Holly's eyes were shut. I let her recover.

But my engorged pole reminded me that I wasn't done yet...

Yes, I definitely wanted to sink my rod into this amazing lady's pussy!...

My hand found her big tit and began to knead it.

Her eyes were still closed. She smiled.

Her palm covered mine and together we kneaded her gorgeous tit.

I moved up and knelt by her head.

She turned to me, wrapped her lips around it and started descending on it.

After taking about half my length into her hungry mouth, she began bobbing while sucking hard.

I was again fast approaching a massive orgasm...

I pulled out in spite of her trying to stop me.

I moved between her legs and buried my cock deep inside her soaking cunt.

Holly's mouth opened and a loud groan escaped. She was on her way to another climax...

I was able to pound her body for like 60 seconds before reaching my peak.

I exploded inside of her, drowning her vagina with hot lava.

Holly's climax started as my seed was flooding her snatch.

Her periodically contracting tunnel on my cock enhanced my experience even more!...

I leaned back trying to regain my breath.

I was thinking, 'This was my first sexual fun... It was great!'

I closed my eyes and began to relax.

I was awaken by a mouth milking my deflated prick...

Holly continued sucking me, cleaning the residue off my organ.

Once it was spotless, Holly glanced at me, "Al, you did a wonderful job. You are very young. How many partners did you have before me?"

"Holly, I am embarrassed to tell you, but you are my first... I was a virgin!..."

She laughed heartily. "For your first time you were excellent. I am proud of you!"

Holly went to her bathroom, freshened herself and then opened a drawer.

She put $2000 in front of me and said, "Dear Al, the ladies I was talking to you about need an escort to feel safe, to help them look good during social events and sometimes they would be interested in extra benefits, like the one you expertly performed today. Now it's up to you to decide whether you are interested or not . As you can see, your wealth will go up significantly if you continue to be good, nice and pleasant. I emphasize again - You'll get this job ONLY if you are pleasant to every woman, even if you decide to reject her offer! You do not have to answer now. If the answer is no, never contact me again. But if you want it, call me by next weekend."

I dressed up took my money and left the house.

My brain said 'yes', my body said 'DEFINITELY YES', but I felt that I was somewhat under the influence...

I still needed 24 hours to digest a simple fact. From a construction worker earning poor salary, I was about to become a gigolo... Is it going to be the same as a male prostitute?...

The next day I phoned Holly and left her a message, "I am willing to try, but I do not want anybody to know my real name or address. For them I'll be Myles. And I need to get in advance the details of the person I'll going to be escorting."

An hour later Holly called me, "Myles, I agree. A reminder though, you are ALWAYS POLITE! And if you refuse to escort more than 2 of my ladies, friends or customers, the deal is off"

"Holly, it sounds fair. Now if you agree, I'd like to begin on weekends, because I won't quit my construction job until I see that I can do what your REAL OFFER is and it is worthwhile for me moneywise..."

Holly chortled, "Myles, you are right. Don't leave your job yet and your first 3 customers will be meeting you on the next 3 consecutive Saturdays. In terms of money, I'd be less worried. The customers I'll be sending your way have 'special needs', but if they are happy after your... encounter, trust me that they'll be VERY generous!.

Myles, your first lady is Ashley Fordham. She expects you at her residence by 6:30 pm. Please don't be late!"

On Saturday I was at the right address 7 minutes early. It was a large mansion sitting on the river bank.

I waited in my car until 2 minutes to 6 o'clock and then rang the bell.

A smiley woman of about 50 answered the door. She was about 5'2", 120lbs, gray hair and elegantly dressed.

"I assume that you are Myles. My name is Ashley. Come on in. If you care to drink something, the bar is over there. I'll be finished in 10 minutes, so sit down and relax. We'll be going to visit my sister."

I checked the bar. It was huge and had every drink that anybody would like, from beers to wines, to Cognacs and Champagnes. And on the side there was a stack of $20 bills... Was it a test to see if I steal the money?!...

I poured myself a glass of white wine, sat down and admired the room.

I was no expert, but obviously somebody with good taste decorated this place.

Ashley reappeared and announced that we needed to leave.

On the way she explained to me that during the visit she may tell others that I was her lover. I was obsessed with pretty cougars... She will put her hands on me and even kiss me in front of other guests.