First Year After High School Ch. 01

My father was of German descent and my mother was an immigrant from Panama. They had 3 children. Troy, the oldest, Regina, a year younger than him, and me, Victor. I was born 6 years after my sister, and I always suspected I was an accident...

Being the youngest, I was spoiled from day one. My older sister was like a mini-mother to me. As a kid, I looked like my classmates, except my skin was darker than most.

When I turned 13, my growth spurt began, and in my senior year in high school I was already 6'0", 170 pounds. I liked swimming and was the top free-style swimmer in school. Rigorous training shaped my muscles. My face changed a lot too. My sister, who used to call me 'little brother,' started calling me 'Mr. Stud.'

My success with girls was the envy of my friends. They pretended to joke about it, but I saw their eyes following me walking by with frequently changing hot girls.

My 18th birthday happened on the first day of my senior year. Ten months later, I already had sex with 3 girls, yet my experience was fairly limited. In addition to playing with tits and rare oral, it was mostly missionary or doggy-style positions in the car or a dark corner in the park.

My scores at school were reasonable, nothing more. The average was B. Except for sports, I was the faster typist in class, likely due to the constant phone messages I sent to my girlfriends.

My average performance could have been a big hurdle if I was keen on going to a highly-sought-after profession in a lucrative college. However, I had no clue what I wanted to be in life! My parents and older sister tried to direct me to different professions, but neither one was interesting enough.

Toward the end of the year, I made up my mind. I'd take a year off studying, find a temporary job, and hopefully know better how to continue. I started looking online for job seeker sites. Most ads demanded higher education, certain skills, or a couple of years experience. Not having any of the above prevented me from applying. I continued searching, and one day I noticed an ad for an assistant to a clothing factory boss. The requirements included high motivation, hard work, occasionally unusual hours, and frequent travels to places where their merchandise was sold. The ad was vague, and it was obvious the boss left himself a lot of room to select a candidate based on the interview. For 2 weeks, I didn't see anything else I could apply to, so I called the office. The receptionist did not ask questions or refer me to anybody but gave me a date and time for an interview.

...

I thought being clean shaven and nicely dressed would show respect, and likely increase my chances, but I wasn't sure what to expect during the interview. As I entered the large office, I saw an older woman in her 50s sitting behind a large mahogany desk. She smiled, pointed to the chair, and said, "I assume you are Victor. My name is Helen Cronin. I own this firm. My former assistant quit a week ago to take care of his sick mother. I cannot function optimally without an assistant. You read the ad I placed, so, are you ready for the job?"

"Ma'am, I took a year off of my studies to decide what profession I wanted to follow. During that time, I plan to work hard and help in any way I can."

She stared at me, "In the ad I did not mention specific tasks on purpose. I require absolute commitment. If you are not ready because your time is limited or you have other plans, let me know now, and you can leave."

"Mrs. Cronin, I have no other obligations that would tie me or limit my time. I am basically a free bird."

She smiled, "The next question may sound intrusive, but I must know the answer in advance. Do you have a girlfriend, and if the answer is yes, how often you see her these days?"

"I started going out with a girl my age about 2 months ago, and lately I see her every weekend."

"Well, remember I travel by plane or car often, and occasionally the trip lasts more than a week."

"I do not see it as an obstacle. I am sure she'll understand."

"Victor, you are probably 18 years old, I'd say around 6'0" tall, and quite handsome. But everything I just said refers to your look. Please tell me a little about yourself."

"I'll be 19 in several months. As I said, after finishing high school, I chose to work for a year and decide later how to continue."

"Can you type?"

I grinned, "I may not know much in certain areas, including the clothing business, but I can type faster than most people I know."

Her eyes inspected me behind her silver-frame glasses, "Victor, before you, I interviewed 4 other candidates. I have a hunch we'll be a good team, so I'll offer you the job. The first few days you'll spend learning about our company. You'll have a small office next to mine, and you'll always sit there when I am around. I may ask you to help me carry stuff, deliver or bring me packages, and accompany me each time I go on a business trip. I'll try to give you a 24 hours notice before any planned trip. I'd like you to start as soon as possible, even tomorrow if you can. And just so we understand each other, you'll do for me ANYTHING I want, am I correct?"

"I'll do everything you wish, as long as it is legal. And if it is OK with you, I'd like to start Monday."

...

Monday morning, I arrived at 8 am and brought donuts for everybody, trying to make good first impression. The 5 young girls giggled. They inspected me, thinking I did not notice. Was it because I was new at the place? Because I was the only male? I wasn't sure, but I let it go. I'd have enough time to know them better.

Helen entered the door at 8:30. She looked stern, even crabby. I hoped she wouldn't turn up to be the boss from hell like Meryl Streep in The Devil Wears Prada. I let her settle down for a couple of minutes and knocked on her door.

"Victor, common in." How did she know it was me?...

"Mrs. Cronin, would you like coffee or tea? There are also donuts if you are interested."

She smiled, "Coffee will be fine with a touch of milk and a Splenda. I do not eat donuts. At my age, I need to keep an eye on my figure."

She removed her coat and I glanced at her. She looked good for her age. A few wrinkles were seen under her eyes. However, her face was almost pretty, and the short, dirty-blond hair gave her a noble appearance. Her conservative suit hid a lot of details but she wasn't too fat or too skinny.

"Ma'am, it's none of my business, but from the look of you, diet shouldn't be a concern."

She laughed, "Victor, it is your first day so I'll explain to you some of the rules. First, my name is Helen. Unless we have outsiders around, I'd rather you call me by my first name. Second, if you do not want to get in trouble, be extra careful when you mention weight around women. This is a sensitive issue for most of us."

I raised my hand, "I promise to never again mention your figure looks great in this suit."

She gave me a strange look, "Honey, you are playing with fire, and this is your first day... I want you to take 3 packages to VIP clients in town. You drop them in their offices, and if somebody asks questions, just tell them to call me. By the way, in 3 days we fly to San Francisco for a couple of days. I have to meet a group of designers for the next year's fashion. Talk to Ronda about buying plane tickets and reserve 2 rooms at The Grand Hyatt."

I drove to the 3 offices and left the packages there. When they noticed Helen's name, they just said, "Thank you and say hello."

Ronda worked with Helen for 5 years and was familiar with her wishes. Helen liked to fly United or Delta. She had frequent flyer account with both. Her favorite hotel chains were Hyatt and Wyndham. She preferred vegan foods but would eat chicken or fish on occasion. The first day passed fast. After making the deliveries, Ronda briefed me about the office, telling me it was the main office. The company had 3 other offices in different cities.

The following 2 days I continued distributing a few more packages and started answering Helen's phone calls.

One evening I called Barbara, my girlfriend, to go out. She was busy helping her cousin prepare for her wedding. We agreed to meet when I returned from San Francisco.

...

The flight to San Francisco was uneventful. Helen worked on her computer and I watched a movie on my laptop. We took a taxi to the hotel, and I carried our luggage (I had a small carry on, and she had a large suitcase and a purse).

When I opened the door for her, she removed her 3" heel shoes and sighed, "I hate flights. My feet are killing me."

"Helen, I do not have anything better to do. Would you like me to massage your feet?"

She smirked, "That's an excellent idea. But if you do a good job, I'll ask you to do it after every flight."

"I was hired to help you any way I can. I'll be happy massaging your feet, knowing you'll like me better..."

She washed her feet, rested on the sofa, and placed her small feet on my lap. I never acquired official knowledge of massaging feet, but one of my former girlfriends loved massages and taught me how to do it in a pleasurable way. You guessed right - With my girlfriend it wasn't only foot massage, and most times it ended with satisfying sex.

I began massaging Helen's feet gently. Five minutes later I increased the power. Helen leaned back, closed her eyes, and muttered, "Victor, your magic hands are doing fantastic job. Starting today, after every flight, you give me a foot massage, and by the end of the month, you get a bonus."

"Thank you, ma'am. And if you ever want a body massage as well, let me know. I have some experience, although I have never studied how to do it."

"Did you train to do it on your girlfriends?"

"Yes."

She grinned, "I thought so. It feels great, and almost erotic..."

When I was done, I asked about our plans.

"I didn't arrange anything tonight, because every so often the plane is delayed. I am not hungry, but I won't object to go to the bar later. If you decide to eat dinner, put it on the hotel tab."

"Helen, I'd like to accompany you to the bar, unless you rather I stay here."

"Go eat dinner at 6:45 and come pick me up at 8. We'll go to the bar together."

...

I wasn't very hungry either and grabbed a small sandwich. At 7:55 pm I knocked on Helen's door.

She opened the door and rushed back to the bathroom. I got a glimpse of her back. She came out 15 minutes later and glanced at me, waiting to see my reaction.

I ogled her, and blurted, "You are my boss, but if you were my date, I'd whistle!"

I wasn't lying - She was without the glasses, probably with contact lenses. Her face had little makeup and light-red lipstick, which made her look years younger. Her dress was long and covered her legs, but the upper part displayed amazing cleavage. The tops of her creamy tits were amazing!"

She blushed, "At work, I am dressed conservatively. I thought going to a bar I'd dress up differently. I remembered too late I was going with an 18 years old guy. Victor, if my dress embarrasses you, I can change."

"Please, don't! Going to a bar with such a gorgeous lady is every young man's dream."

She whispered, "You are such a flatterer... Let's go."

The bar had 3 other couples sitting, drinking cocktails, and chatting in a low voice.

"Helen, what would you like to drink?"

"A Mojito will be fine. What are you going to drink?"

"I'll take a sangria. I always liked it. If it's made properly, with red wine and not too sweet, it's my favorite."

She chugged her Mojito and stared at my face.

I asked her, "Where is Mr. Cronin?"

"He died 4 years ago. He was much older than me. He had a stroke and died 2 days later."

"I bet it isn't easy to live alone."

"I was too depressed for a year or so, and then tried my luck with eHarmony. I had multiple options. I tried three of them but neither was for me. I won't bother you with the details." She continued drinking the Mojito and soon her glass was empty.

"Shall I order you another one?"

"Yes, please."

As I was sipping on my sangria, I watched her gulping down her second Mojito.

I inquired Helen about the history of the company, and how successful it was.

She started by describing how she borrowed money to start it. In the beginning, it was rough, but 2 years later, the firm became profitable, and these days it was making millions every year with branches in all the big cities.

Her answer lasted 20 minutes. When she started talking, her voice was normal, and turned slightly slurry later on. I waited for her to finish and suggested, "Helen, I think we should go back to the room."

She mumbled, "Good idea."

Helen stood up and seemed slightly wobbly. I Grabbed her hand and helped her to the elevator. She leaned on the wall and closed her eyes. When the elevator stopped, I helped her again to her door. She fumbled with the key, and eventually the door opened. She turned to me with a smile, "Would you like a nightcap?"

I knew she was under the influence, and wanted to make sure she made it safely to her bed, so I accepted.

She sighed, "This dress is nice for evening events. Let me go to the bathroom and have something more comfortable."

Helen came out wearing a short red nighty. She was somewhat unsteady on her legs and lay on the sofa. She gazed at me, "Victor, your foot massage earlier was wonderful. Would you be nice and do it again?"

"Yes, ma'am."

I sat near her, lifted her legs, and put them on my lap. By doing so, her hem climbed up her thighs. I started rubbing one leg. Soon she moaned softly and spread her legs slightly. This opened the robe and I could see her sheer red panties covering a bald cunt. I stared at her face. Her eyes were shut and immense pleasure was written on her face.

After 10 minutes, I moved to the other foot, and she left the first one on my knee. The robe opened further, and the valley between her breasts got exposed. The sight was unexpected and erotic. My pecker began throbbing. It signaled trouble, but I couldn't change its trajectory. I tried to think about the last movie I saw on the plane, and then about needing to go more often for my exercise routine. However, my prick refused to obey. It continued expanding. It didn't help that Helen's body started rocking slightly from side to side, and she was groaning. Shortly after her right breast became uncovered. I always assumed at her age the breasts sag significantly, yet hers sagged minimally, and her dark nipple looked very tempting. My cock hardened at a faster pace.

I continued massaging her foot and heard her whispering, "Victor, I feel something hard there. Are you horny too?"

I lifted her legs, stood up, and said, "Helen, let me help you to bed."

With her eyes closed she mumbled, "Oh, thank you, I thought you'd never have the guts..."

I put her to bed and said good night. She was asleep before I closed her door behind me.

...

We met for breakfast. Helen wore one of her work-suits and looked professional. Nothing in her face or demeanor suggested she remembered the previous night. As we ate, she explained the agenda; Initially, we'd sit and listen to 2 other speakers, who would elaborate on current fashion trends in the USA. Then she would present her vision for the future based on the changing demographics, styles, and colors. My job was to carry her laptop and a bag with fabrique samples she planned to introduce.

It was the first time I attended her presentation. I relied on Helen. When we entered the large room, I took a seat behind her. I won't bore you with details, but the reaction to Helen's talk was enthusiastic. Everybody clapped and later she answered questions for half an hour.

Frankly, I was bored. However, the thrilled audience energized Helen, and when she was done, she grinned, "Everybody loved my ideas! Even Mr. Thompson, who never agreed with me before. I feel wonderful. Three people invited me to go out with them. I pretended to be tired. Let's celebrate it together in the best restaurant in town and then, if we are still on our feet, we'll go to a dancing club. You can dance, can't you?"

"Well... I went to 2 disco clubs before, and everybody was shaking and pretending to dance. I think I can fake it, but I am no dancer."

She laughed, "Good enough for me. After the successful talk, I am full of energy and better take it out dancing. You are my guest, so you choose - Italian or seafood?"

"I think you'd rather go for seafood, so I'm in."

"Great. Fog Harbor Fish House is my favorite in Frisco. I know the chef. I'll call him to ensure a good table."

We ended up at a table for 2 near a large window, facing a breathtaking view of the bay. I was so fascinated by the calm water, boats, and sea lions, that I hardly paid attention to the food I ordered. I just recall it was tasty... Helen also ordered a bottle of white wine. By the time my glass was empty, the bottle was empty too. Helen must have liked alcoholic drinks very much...

After the meal, Helen asked an Uber to drive us to Tope, a known dancing bar/club in town. It was still early, and only 10 people were there. Helen won't be denied; She asked the DJ to play slow music. He did and whispered that if we were interested, later on, a fantastic comedian would have a show in the club.

We smiled but were noncommittal. She pulled me to the floor, where 2 other couples were moving slowly. Helen placed my hands on her waist and hugged my neck with hers. The first dance was OK; we barely moved. Helen's eyes were shut and she had a satisfied smile. I liked to see her happy, and the 'dance' was only a minor stroll on the floor, so it didn't bother me. During a short break, before the next song started, her body clutched to mine, her head leaned on my chest, and her soft tits bounced against my pectorals. I didn't know if she wanted to relax by leaning on my body or felt unsteady on her feet, but her jiggling breasts woke my member, and it began stiffening. It kept engorging and eventually Helen felt it. She whispered, "Victor, I like being close to you, but you are very naughty."

I whispered back, "Sorry, Helen, but I cannot control my cock. He thinks you are very sexy."

She raised her face, looked into my eyes, and grinned, "Thank you."

We continued dancing and I noticed 3 additional couples joined. It felt better to be less noticed, especially with the tent in my pants. It grew, hardened, and separated us slightly. Helen chuckled, caressed it lightly, and muttered, "Can't you tell him to wait until we are back in the hotel?"

I smirked, "I explained it to him, but when you are too close, he ignores my wishes..."

Her eyes met mine again and she blurted, "Tell him I'll take care of him in the room."

Knowing Helen was tipsy, I bent my head and said to my prick, "Hey, buddy, did you hear that? Helen promised to care for you later, so be nice."

Helen watched my bulge for a minute, but it never decreased. She sighed, "OK, Victor, time to go back to the hotel."

A taxi took us back. throughout the ride, Helen peeked at my groin multiple times, and as a result, the bulge diminished only slightly. I walked with my hands in front of me to hide the unwanted growth in my midriff.

In the elevator, I ensured she didn't wobble. She didn't, so I followed her. Her cute butt swayed exquisitely from side to side, which in turn lifted my poor cock again...

We reached her door, and she turned to me, "Victor, come in."

She watched me walking to the sofa with my covered erect cock leading the way. She stood before me and said, "Show me what is wrong with him."

I glanced at her, "Helen, that's OK. In a minute or two it will soften,"

"I thought so too, but for more than 30 minutes it didn't budge. Show me!"

"Helen, please, you drank too much, and now you say something you don't mean to."