I first met Jerry Winston while we were standing in the freshman registration line at Case Eastern Reserve University. It was obvious that we were; a) new students and b) freshmen as we had the proverbial 'deer in the headlights' look about us. I started up a conversation with Jerry because everyone does while they're standing in long lines. By the time we actually advanced far enough that we could see the registrars' desk we were friends. By the time we actually got registered for classes we had decided to share a dorm room.
It was an interesting mix of cultures, the two of us. Jerry was from a moneyed if not wealthy family in Florida while I was from your typical middle-class family in mid-state Texas. Although it was obvious that Jerry, or at least his family, had money he didn't flaunt it at all, he was much more oblivious to the fact that everyone didn't have access to the same amount of capital that he did. I asked him why he didn't live in an apartment instead of a dorm room and he simply said that his mother wanted him to get the true flavor of campus life and to do that he needed to live in a dorm.
The afternoon we moved into to our room in Heater Hall, Jerry grabbed the bed by the window while I got the one next to the door. I remember Jerry unpacking some personal things and setting his books and pictures up onto his bookshelf, which included 'The Picture'. On his bookshelf Jerry set down a 9"x12" picture of a stunning beautiful woman. She was standing on a rock ledge overlooking breaking waves with a small, tree-covered mountain in the background. The woman was wearing a white, almost see-through, off shoulder, peasant blouse and a pair of very short, khaki shorts. Her auburn hair was blowing in the breeze and I could see freckles covering her shoulders.
"Damn Jerry, who's that?" When I asked he looked up, then turned to see what I was looking at.
"Oh, that's my mom."
Just like that, it was his mom! I knew that I had to be careful with where this conversation was going. "Oh sure, your mom, where was it taken?"
"In Hawaii. Mom took me to Molokai last summer. You know a graduation gift of sorts."
"Oh sure, a graduation gift!" Let me see now, what had my parents given me for a graduation gift? Oh yes, I remember, it was a Parker fountain pen, but it was a nice one. "How come your dad's not in the picture?"
"Oh, he was on another one of his business trips. Christ Alex he's always on a business trip somewhere. If it weren't for my mom no one would have seen anything I did in high school. Mom was at every one of my track meets and at my graduation but not my old man, nope, he would never let something like what I was doing interfere with one of his business trips. So why did you ask — about my mom I mean?"
I thought that it was fairly obvious that Jerry was upset at his father's absence from his life and that he didn't seem to care about what Jerry had accomplished. "Oh nothing really, I was just thinking that maybe it was your girlfriend, that's all." He turned and looked at me incredulously.
"My girlfriend? Christ Alex she's my mother! Do I look like I would go out with someone that old?"
"No I guess not, sorry." I looked back at the picture and tried to determine his mothers' age. The picture had been taken from about twenty feet away so it was hard to distinguish exactly how old she was but she looked like she could have been 25 just as easily as 45. Thinking that Jerry was probably 19 and if he was born when she graduated from high school that would make her... 37. If it were after college then she would have to be in her early forties. Still she didn't look that old.
The next four months went by quickly and before anyone realized it finals were upon us and we were excited about the upcoming school break. Jerry and I were fast friends not going anywhere on campus, or off for that matter, without each other in tow. We even double dated on a couple of occasions. Due to a quirk in scheduling that year we ended up with a seven day break for the Thanksgiving Day holidays to be followed in two weeks by another break, a three-week recess for the Christmas and New Years holidays. I had decided to stay on campus for Thanksgiving and use that time for studying then head to Texas for the Christmas break but Jerry was going home for both. Two days before the Thanksgiving break Jerry was talking with him mom on his phone when he turned to me.
"Hey Alex, mom wants to know if you would like to come home with me for Thanksgiving?"
"What? Home with you?"
"Sure, why not. I've told mom so much about you that she wants to meet you. Come on, we'll have a good time and besides, it's only a week."
I held up a single finger, indicating to him that I was thinking about it and I was. Why not I thought, beside it would give me the opportunity to actually see the woman whose picture I had been ogling at for the past four months. "Sure Jerry, if it's not any trouble for your mom, I'll be happy to tag along."
As I said, I had grown up in a middle class family, the only sibling of my parents, living in rural Odessa, Texas. If it hadn't been for a variety of scholarships I would have never been able to afford to attend Case Eastern, but not Jerry, nope, Jerry's family was wealthy enough that they just paid for everything. All I really knew about his family was that they lived a country club community on the outskirts of Lafayette, Florida and that Jerry's family paid for his schooling, room and board, and gave him a very nice allowance — one in which we generously used for pizzas and beer.
On Friday we packed our bags for the trip to Florida, took a cab to the airport and boarded a flight for Tampa. Two hours later we landed and Jerry picked up a rental car for the hour-long drive to his house. I enjoyed the scenery having never been in Florida but you can't even begin to imagine how I felt went we drove through the gates of the country club and up to his house. Amazed? Sure. Stunned? Absolutely. Beyond belief? All of the above and in spades. Sitting at the back of a fifty foot long driveway was a separate five-car garage. To the left of the garage was a single story house that was bigger than any house I had ever seen in Odessa. Jerry parked the car in front of the garage and we hopped out and Jerry led me inside the side door of the house, through a mudroom, which by the way was bigger than my parents' kitchen and into his kitchen where his mother was making iced tea.
"OH MY GOD! Jeremy, you're home!" His mother ran up and grabbed Jerry and kissed his cheek and hugged him. "Thank God your home safe." Then she turned and looked at me, "And you must be Alex." She hugged me too then pushed back, "Welcome to our home Alex, I'm Anna."
When she hugged me her breasts crushed against my chest and sent shivers through my body. "Thank you ma'am. And thank you for the invitation; I really appreciate your hospitality."
She looked me up and down. "My, my, a real gentleman." She looked at Jerry. "You didn't tell me that he had such good manners Jeremy. And Alex, it's Anna, not ma'am, alright?" She handed us the iced teas and before I could answer her, Jerry started giving me a tour of the house.
It was the first time I had heard that his name was really Jeremy not Jerry and I noticed he winced when Anna called him Jeremy. "So you don't like Jeremy?"
"Christ no! It was my grandfathers' name and I got stuck with it but if I hear you using it or telling anyone it's my real name I'll break both your legs... then I'll kill you."
I laughed at him. "No problem bro." The Winston house was constructed in a huge 'L' shape with his parents' bedroom on the long end of the 'L' while Jerry's was on the short end. And in between? Inside the house, in between the two ends of the L were a formal dining room, a formal living room a den that overlooked the outdoor 50' x 50', net covered, swimming pool and spa. Behind the swimming pool there was a guest house, which was a one-bedroom structure with a separate living room and small kitchenette that would be mine for the duration of the visit. Good Christ, how much money did these people have anyway? I went out to the car and moved my stuff into the guest house, changed into a swimsuit, and met Jerry out at the pool. For the next two hours we swam, tanned and sipped on iced tea.
That night the three of us ate dinner in the formal dining room, Anna having explained that Jerry's father was in Thailand for the next two weeks. Anna had changed for dinner, now she was wearing a short black cocktail dress that showed off her legs and was just cut low enough that the tops of her breasts also showed. Jerry had on a dress shirt without a tie and a pair of slacks and I was the shumck wearing a golf shirt and pair of jeans. I watched Anna throughout dinner, trying not to be too obvious about it. She was even prettier than her picture, standing somewhere around 5'7" and maybe a 120 pounds. Her hair had been styled since the Hawaiian picture and was now much shorter, and was combed back on the sides. I could only see the tops of her breasts but they looked gorgeous to me. What really caught my attention was her legs and butt, all I can say it they were to die for, her long, tanned legs climbing up underneath that dress and attaching themselves to her two very firm, and nicely rounded, butt cheeks. All in all she was quite the woman. I still couldn't get a handle on her age although I just finally assumed that she had to be in her early forties.
.... There is more of this story ...