Chapter 8

As I walked home at 1:43 a.m. I was right about the starched uniform. The stiff fabric of my black and white checked pants played hell with the chafed head of my dick. But rather than wince and trouble me with the irritation of my parts I was fascinated enough at how it had come about, chuckling, and shaking my head every hundred feet or so.

I finally realized what it might have meant when Sister Natalie and Rina Strelnicov had said to me throughout our relationships about me being “special.” Since I firmly felt they: Natalie, Rina, and now Samantha were the “special” ones, and I was just the convenient young male who happened to be in the right place at the right time I thought about the string of females I had had sex with since the tender age of fourteen. It started with Sister Natalie who gave me my first blowjob and then insisted on me servicing her fellow nuns. She had finally put me together with Sister Mary Cecile who was the only girl I had truly fallen in love with. She left the convent under mysterious circumstances and no one, even Sister Natalie told me what happened to her.

Kathy Warren and Rosie Kowalski were neighbor girls younger than me with whom I had sex. Sure, the fact I had been introduced to sex by an older woman made me more confident. But I was also encouraged by my friend Ray, Kathy’s brother who was having an incestuous relationship with his sibling. Rosie just became part of the mix as Kathy’s friend. I expect that it would have happened anyway which made more sense in the scheme of things. But my relationship with Sister Natalie certainly gave me more confidence as well as created the beginnings of a more skillful lover.

A coincidence with Rina Strelnicov which unbeknownst to me was set in motion by Sister Natalie, I finally figured out that “Sissy” (the sexual name Natalie insisted I call her in our liaisons) had put it together with her friend Rina who at one time had been a nun with Natalie as a young sister in that convent

Before this spectacular experience with Samantha Onassis, I had had sex with seven females. Though I would have liked to have shouted it from the rooftops I don’t say it to brag. I say it more in awe of what had happened to me so early in my life. Being human, I can’t help but tally the number, not so much in the vein of notching my ivory-handled six-gun, but in the satisfaction of being inside them with so little effort on my part. I was still young enough to marvel at the mechanics of sex, always thrilled with how good the feeling of a hand, mouth, or vagina felt on my penis. And I was equally happy to know how thrilling or satisfying I was being to those females. In my mind, I was just an ordinary college freshman with uncommon experiences. But having just been involved in such a phenomenal experience with Sam I still couldn’t fully grasp why all of this was happening to me.

Make no mistake, the sex with Kathy and Rosie was great. But with each new experience with Sister Natalie, Rina, and now Sam I felt like I was being taught by experts whose purpose was to mold me into the kind of lover every woman wishes for. And every suggestion they made went into my mental user’s manual. Life just keeps treating me so well. I hope nothing goes wrong and the shit doesn’t hit the fan.

From the time she was a little girl Samantha’s dream was to manage her father’s business. Unlike her sisters who intended upon getting married and have families, Sam had vowed to never fall in love with a man. She didn’t want anything to deter her from her ambition of running Sig’s and eventually developing it into a more successful enterprise. She had lovers along the way but found that too many men were interested in using and controlling her. By nature, she was a natural manager who knew how to manipulate people for her purposes. Often, she did it to her and their satisfaction as well. Additionally, she like her sisters was elegantly attractive. Though Greek they had no Turkish influence, all possessing the ancient elegance of the stylized, mythic goddesses with blonde hair and blue eyes. Samantha looked like Rosana Podesta who played Helen of Troy in the 1956 movie of the same name.

A highly sexual individual who always found partners that, if not sexually adept, Sam quickly tutored them to be. And being a natural psychologist, she used her sex as an adjunct to managing her business most efficiently and profitably, an example of which was the way she managed to have Harley Norton cut her a more attractive deal on the frozen custard machine and install it at no charge. For her personal preferences, she was what we call today a “Cougar” who prefers sex with men younger than her. For the last ten years, her sex was mostly conducted with John’s Hopkins students who worked part-time at Sig’s which turned out to be an outstanding interlude for both she and the students.

Her latest employee, Toby Wakefield from Ohio was quickly becoming her most prized part-timer. Unlike his predecessors who were strictly students in their field, Toby had a much better work ethic. He had also quickly proved to her how keen his logical acumen was by coming out with the idea of installing frozen custard machines in Sig’s diners which had just given her the most profitable day of the year. And there was something about him that made her nipples tingle whenever he looked at her with blue eyes that were sounding her soul.

When he took over running the frozen custard stand that day, she kept watching the way he worked and thought he does everything with such a confident purpose. And the way he makes the customers feel good when he jokes with them is so natural. She couldn’t help but notice his cute, young ass. Then when he turned toward her gaze she glimpsed his lips, his hands, and his crotch. Is he hung or does he have a little boy pee-pee? she thought I’ll take either one or show him how to use it. It was her style to wait for a few months before ravishing the help (she had seen her father do it with the waitresses and it always seemed to work). But there was something about Toby that made her need to act more quickly.

She felt more comfortable on her home turf but there was also the urge to do it in the apartment where Brandon Cornwell from Michigan had spent three years, the same apartment Toby lived in now. She liked the place. The doctor who owned it, Sergei Strelnicov had entertained her there numerous times before he got married. He had been a regular at Sig’s as had his wife before they moved and started renting the place to students. But she decided to take Toby upstairs, take him to bed and celebrate with him. There was a vibe about him that made her want to make the young man part of the décor of her apartment.

There was something about seducing and regularizing sex with young men who worked for her that fit into Samantha’s routine. She made it a ritual: taking a shower with the diner’s dirtied food worker, fucking him, giving him a freshly starched uniform, knowing his sensitive penis would be irritated by the stiff fabric ... and putting the discarded garments in the laundry bin downstairs. But with Toby, she found herself being more purposeful ... as if he fit more appropriately into the order of things.

The blowjob in the bathtub showed her the difference. First, his was one of the most magnificent cocks she had ever had the privilege of having in her mouth. With the others, her purpose had always been to make him cum and desensitize the usually inexperienced young man. But Toby lasted until her jaw was numb and the water running past her nose made her feel like she was being waterboarded.

When she took him to bed, she forcefully mounted him. The feeling of his huge knob opening her was so expansive that she felt like her eyeballs would pop out. Rather than tightening her vaginal muscles, she relaxed them which brought forth the surreal vision of her epithelial duct acting as the mold for his sculpted penis. She imagined she could feel his veins and musculature as if they were manifestations of a French tickler. With the magic of his bulk filling her insides she rode him frantically. Out of breath and fatigued she was baffled by his endurance. With all her inexperienced lovers she had often said, “Please don’t stop.” But with Toby, she thought Jesus what IS it with this kid? Sucking maniacally, she pulled off and flailed his obstinate erection with her hand, finally imploring, “For Chrissake Toby CUM for me,” and he finally popped.

Completely out of breath she rolled on her side and pulled him into a spoon. As she thoughtfully fondled his flaccid, slimy bulk she pondered what do I HAVE here and said, “You certainly have been around Toby, haven’t you?”

“I’m not a virgin Sam if that’s what you mean.”

“I’m not a virgin,” she mimicked in her mind and you’re not a bullshitter either. JESUS. “Let’s say this Toby, you do have an idea how to please a girl. I don’t need to know the specifics of your frolics and am impressed that you’re not bragging about it. You’re a special young man, my friend, I hope you know that.” She felt him pushing his ass into her at

the compliment.

She was blown away when this eighteen-year-old kid said to her, “Why don’t I climb over and spoon behind you, I’d like to fondle your breasts and do some other stuff.”

“Other stuff Toby?” she mockingly said, “What are you talking about?”

“I-I...” lost for words he said, “I don’t know how to tell you, Sam, can you just let me over and show you? SHEESH.”

Not waiting for her to move he hoisted himself over her body as she thought nope, he’s not like the others. When they had wiggled themselves into position and he thrust his hand between her right arm and body then ever so gently tweaked her nipple she thought this kid just might know something. Proving part of the “something” he feathered the backs of his fingertips to every sector of her right breast then began rolling her nipple between his index finger and thumb. As she started to say, “Squeeze it,” his finger and thumb were already tightening which caused a shock that emanated to her clitoris and toes triggering a mini climax that caused her vagina to seep with her feminine secretions. “That was good Toby,” she sighed and was surprised when he eased his hips back from her ass and pulled on her hips to roll her on her back.

Gently grasping her right knee, he coaxed her legs open and, as he kissed the side of her neck began barely touching her inner thigh as his titillating fingertips toward her the juncture of her legs. Geeze, she thought this fucking kid is giving me goosebumps. He felt them with satisfaction as his hand neared what seemed like the oven of her quim.

When he continued using his fingers on her outer labia like a safecracker she couldn’t help saying, “Where in hell have you learned all this Toby?”