We were sitting at a window table in a cozy restaurant called The Spinnaker and marveling at the beauty that is San Francisco at night. The Spinnaker is located in the chic community of Sausalito, which is just across the Golden Gate Bridge in Marin County. Years ago Sausalito was just another struggling fishing community on the bay but since the late 70's when land prices soared out of sight it became a playgrounds for the rich and famous of the City. We had driven across the bridge for dinner and were just finishing off the last of our wine and waiting for the check so we could head back to the apartment. My name is Jeremy Scott and tonight I am an invited guest of my roommate, Ashley Lawton and her mother, Jaime.
Ashley and I are both nursing students at San Francisco State University where Ashley is a junior and I'm just two months shy of graduation. Ashley and I also share an apartment off of 19th street near the university, a building that has eight apartments on two floors that has, for some reason, always been rented to the universities' nursing students. My guess is that the landlord has always felt more comfortable renting to nursing students that he feels are more responsible than the normal radical student population. On the other hand he is an old man and maybe he just enjoys the company of all the pretty nursing students, present company excluded.
I daubed at my mouth with a napkin and looked across the table at our host. "Mrs. Lawton I want to thank you for inviting me to dinner, it's always a pleasure to have you visiting with us." As I said this the waiter slid the check in an expensive leather folder under her right hand.
"Jeremy I've told you a thousand times, its Jaime and you're more than welcome honey."
I had first met Mrs. Jaime Lawton two years ago after her daughter had answered my ad on the student union bulletin board for a nursing student roommate. Ashley had immediately liked the apartment but not the idea that she would have to share it with a male. However because we were both nursing students and had a number of mutual friends in the nursing program we sat down and talked our way through most of the issues and she agreed to move in the following weekend. Her mother took two days off from work and drove up from Los Angeles to help her daughter get settled into her new digs and to bring some things she wanted from home.
Jaime is the senior vice president for marketing for a large aerospace corporation in Los Angeles and according to Ashley makes a seven-figure salary. She divorced Ashley's father almost six years ago and for the life of me I don't know why he ever let her go, to my way of thinking she is quite the woman. The story goes that Jaime was married just after high school and Ashley was born some six months after the wedding so I figured that made Jaime around forty. She is a statuesque woman and reminds me of a fashion model, standing at least five foot eight without heels and with a body that is proportionate to her height, her breasts excluded. The first time we met she came to the apartment and used her daughter's room to change from a business suit into a pair of shorts and a tee shirt and I immediately fell in love with her small breasts and long legs. Jaime is a redhead with sea green eyes and her creamy white skin is covered with beautiful tiny red freckles. As we helped move Ashley's things into the apartment I kept watching Jaime and I thought that she was one of the sexiest women I had ever seen but I never said anything to Ashley, after all that was my roommates mother I was ogling!
I turned 22 this summer and since graduating from high school I've had had only two real girlfriends and both of them were during my freshman year at State. Oh I've dated on occasions and it's not that I'm ugly or gay or anything like that, in fact most of the girls in school actually think I'm kind of cute. My real problem is that I just don't have a lot of confidence when it comes to women so I'm content to let them make the first move, if there is one to be made, and then take it from there.
Jaime signed the tab and slipped her credit card back into her purse and we left the restaurant. We had a short wait while the parking attendant brought her rented Lexus to the front door for our twenty-minute drive back home. I sat in the backseat and let Ashley sit up front with her mother and listened as they chatted about school and her old friends on the drive. Jaime had decided to stay at our apartment on this trip, something that she did on occasion, and I had once again gallantly offered her my room but she insisted that she would be fine on the couch and that was that. Once we found a parking space for the car, no easy task in the City, we walked back to the apartment and Ashley put on a pot of coffee then went into her bedroom to change clothes. Jaime and I sat at the kitchen table and had a light conversation about school, living in the City, what I wanted to do after graduation, yada, yada, yada. Then all of a sudden, like a sirocco blowing across the desert, she hit me with 'the' question.
"Tell me something Jeremy, after living together for two years why haven't you and Ashley... uh... well, you know, dated."
Although I knew what she was asking, it definitely wasn't about dating it was all about sex. The question had caught me off guard and I stuttered while trying to think of a good answer. It was obvious that Ashley hadn't told her mother that she was gay and it certainly wasn't my position to 'out' her to her mother. "Uh... well, I guess that we just decided it was prudent to stay good friends and roommates. I mean she has her friends and I have mine and well it's best that roommates not become too involved, especially now that I'll be finished with school in a couple of months and she still has another year to go."
"Alright Jeremy I understand that, but you do find her attractive don't you?"
Duh! Of course I did, after all Ashley was almost a clone of her mother, only she was the younger version and had bigger boobs, but she just wasn't into guys. "Uh, well sure I do. I mean Ashley is a beautiful person, both inside and out, but I think its best that we just remain friends." I was hoping that would end the conversation but Jaime wasn't about to give up so easily.
"Hummm, well I guess that kind of surprises me Jeremy. I mean for Christ's sakes look at her... she's in excellent shape and what a body! Christ she looks just like I did when I was twenty, except for her breasts, their amazing! 36D's and absolutely no sag to them at all... of course she's still young but what I wouldn't give to have breasts like hers! God knows she sure didn't inherit them from me, just look at these." She cupped her small breasts through her blouse and held them up towards me.
"Uh, well I think you have a wonderful figure Jaime and in fact I tend to prefer women with small breasts!"
"Really, how come?"
"I really don't know but I've always been attracted to small breasted women. My girlfriend in high school was practically flat-chested and most of the girls I've gone out with here at school have had small breasts too. It's just something that attracts me." At that point in our conversation Ashley walked back into the kitchen.
"My God Jeremy, are you actually discussing breast sizes with my mother?" She giggled as she said it.
"Well she started it," I protested, "telling me that you're a 36D and that she wished she had your boobs!"
"MOTHER! That's private information, how could you?"
I could tell that she wasn't really mad at her mother even as much as she chastised her.
"Well you're both nursing students so why can't we have an adult discussion about human anatomy" Jaime asked.
"Oh God mother, you're horrible. The next thing you'll think of is to have a strip show so Jeremy can decide which of us has the best set of tits!"
"Hey... that sounds like a great idea too me!" I called out. They both turned and starred at me and not in a good way. I lower my head and looked down at the floor. "Sorry." I whispered and they both laughed then Ashley got up and poured us all more coffee.
It was just after midnight when Ashley announced that she was going to bed. "Sorry gang but I have clinical practice tomorrow at San Francisco General so I've got to get some sleep. You go ahead and stay up as long as you want, I'll close my door."
Ashley left for bed and Jaime and I continued to talk until almost one in the morning then she decided to change for bed. "Jeremy would you please pour me a half of cup while I get changed."
"Sure." Jaime got up and went into the living room and grabbed her pajamas and walked down the hall to the bathroom to change for the night. I washed out her cup and poured a half of cup of new coffee and had just set it down on the table when she walked back into the kitchen. When I looked up and saw her my knees went weak and I suspect that my jaw dropped open and I only hoped that I wasn't drooling. Jaime had changed into a pair of dark green satin lounging pajamas that clung to her body and showed off her figure perfectly. The top of the outfit buttoned up the front and there were these small gaps in the material and I could see her creamy skin showing through. I knew that she wasn't wearing a bra and the movement of her breasts, even as small as they were, captivated my attention as she walked across the kitchen and sat down.
"Are you alright Jeremy? I mean you look a little pale."
.... There is more of this story ...