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.
After dinner we all went into the den to watch television and finish off the remainder of the wine from dinner. Around ten Jerry yawned and indicated that he was off to bed. I thought that it would be prudent of me to do the same thing but Anna asked me to stay behind for a minute so I did.
"Tell me Alex, what kind of a roommate is Jeremy?"
Anna was sitting across from me in a large leather easy chair and I had a great view of her legs, her dress having ridden up to the top of her thighs while we watched TV. "Well, he is my best friend and we certainly enjoy each others company so I guess you couldn't ask for a much better roommate."
"I see, but what about girls? I mean does he date at all? Jeremy has always been quite private and he hasn't shared much with me. "
"Ummm, look Anna I'm not real comfortable discussing Jerry's private life, I hope you understand?"
"Oh sure Alex, I understand and I'm really not trying to pry, it's just that when he was in high school he didn't date all that much and I'm worried that he might be, well too shy and that maybe I've sheltered him too much."
"Oh I don't think you have to worry Anna, Jerry dates on occasions."
"How about you Alex, a steady girlfriend?"
"No, not really. To be truthful I'm on scholarship and really have to maintain my grades so mostly it's Jerry and I plus pizza and beer."
She laughed at my description of my life as a student then she rose up out of her chair and the movement allowed me to get just a glimpse of her panties. She moved over to the bar and held up the bottle of wine, offering me another glass. "Alex?"
"Uh, no thanks Anna, another time perhaps."
"Alright, I've got to go to bed too. Good night Alex."
"Good night Anna and thank you for dinner."
"Your welcome honey and I have to tell you that I think you've been a very good influence on my son."
Anna turned and walked back toward her bedroom and I walked out the back door and into the darkness of the night toward the guest house. As I came around the edge of the pool I saw the lights go on in the corner bedroom and when I looked in that direction I stopped dead in my tracks. Anna hadn't closed her drapes and I could see through the window as she stood in the middle of her bedroom unzipping her dress. I looked around to make sure I couldn't be seen and watched as the dress slid off of her shoulders and down onto the floor. She turned slightly then reached behind her and unsnapped her bra and took it off and she gently massaged her shoulders where the straps had dug into her skin. Anna had a wonderful set of breasts, standing proudly out from her chest and I wondered how much that might have to do with plastic surgery. Her panties were the next item to go and after they were off the auburn haired mother of my best friend climbed naked into the bed, pulled up the covers up and turned off the lights. I stood in the darkness for what seemed like an hour but was probably no more than a couple of minutes thinking about what I had just witnessed. Surly she must have realized that I had gone outside, so was that a show for me? And what about the questions about a girlfriend, what was that all about? Thinking about Anna's body but confused by her actions I walked into the guest house and climbed into my own bed and fell asleep, my cock in my hand.
The next morning Jerry woke me around eight and we wolfed down a quick breakfast before heading out to the country club for a round of golf. During the time we were in the kitchen Anna was nowhere to be seen and I wondered what she was doing. Was she still naked in her bed? Maybe she was in the shower playing with her pussy?
"Hey?" Jerry called. "Are you listening to me?"
"Uh, yea sure, what did you say?"
"I said get your mind on the golf match, now let's go."
It was just after two that afternoon when Jerry and I got back from the country club. Jerry parked the car and we got out and walked behind the garage and into the back yard. We had decided to take showers before eating a snack. When we rounded the corner I saw that Anna was lying out on the pool deck wearing a fairly conservative two-piece bathing suit with the top untied. She looked up as we approached, holding up the bra to her chest.
"Hi guys, how was the golf game?"
"Oh it was alright mom, I shot an 88 which is good for me but the stud here shot an 82, way below his normal score. God mother he's never shot in the 80's before. We skinned the guys we were playing with."
"So maybe Alex is some sort of a ringer?"
"Yea, maybe. Well look, we're going to take showers and clean up then get a snack. You need any help with dinner mom?"
"Nope, I've got everything ready. Dinner is at seven boys."
Jerry walked across the grass and into the house and I turned to go into the guest house.
I turned back to see that Anna was looking up at me. 'Yes?"
"Would you mind doing me a favor?"
"Sure, what do you need?"
"Well I've been out her for about a half an hour and I can't get any lotion on my back, would you mind?"
"Nope, not at all." I walked over to her lounge chair and leaned over and grabbed the bottle of lotion. I squirted some into my hand and then rubbed both hands together. "Ready?"
I started on her shoulders gently rubbing in small circles and going lower and lower. She just lay there letting my hands caress her shoulders, her back and her sides. I really wanted to drop my fingers down about an inch little lower, near her breasts but knew that probably wasn't a good idea. As my hands got to the small of her back I could see that her breathing had deepened. My fingers worked the lotion into her skin and I stopped at the top of the bottom of her suit. "There we go, all done."
"Would you mind doing my legs too?"
What the hell? She could obviously reach her legs. "Sure, no problem." I shook the bottle until some more lotion was in my hands and I started on her right leg. As my hands slowly moved from her ankles to her knees then to her thighs I could see her squirming just a little bit and I wondered if she was getting turned on. "That feel alright Anna?"
"Oh yes Alex, its wonderful. You have very strong hands, have you ever thought about learning how to give massages?"
"No, not really." I continued and I was positive that her butt was lifting up to meet my fingers as they neared her pussy. I finished off her other leg, capped the bottle and told her I was headed to the shower.
"Alright Alex, see you at dinner, and thanks."
"Your welcome." I went into the guest house and walked over to the fridge and pulled out a can of Newcastle Brown Ale and popped the top. What in the hell had that all been about? Combined with last night's conversation and then her exhibitionism in the window you would think that she was trying to seduce me. Naw, that Mrs. Robinson shit only works in the movies... still, I wouldn't say no to her. I walked over to the window and pulled back the curtain just a hair and looked out at the pool. Anna had turned onto her side, her back was to me, but I was sure that she had one hand inside her suit bottom and that she was rubbing her clit. My God what a sight!
At the dinner table that night Jerry told Anna that he had a date with Liz, his old high school girlfriend and that they were going to the movies.
"What about Alex honey, are you taking him with you?"
"God mother, it's a date not a threesome."
"Well that's just plain rude of you Jeremy. Alex is your guest and you should be thinking about him too."
I spoke up. "It's alright Mrs. Winston, I really don't want to go out anyway, I think the golf took a real toll on me. I'm not used to the humidity you have here in Florida. In Texas it's hot, but there really isn't any humidity. I'll be glad to just stay and enjoy the air conditioning." She huffed for a while and Jerry took the opportunity to slip away from the table and head out the back door. I stood up and help Anna clear the table. We worked together in the kitchen and cleaned off the dishes and got them into the dishwasher and pushed the 'do all the work' button on the machine and went out into the den.
"Another glass of wine Alex?"
"Sure, that would be nice." She poured a glass of cold Chardonnay and handed it to me.
"How about a movie?"