18 to 99byfurryfan©
All characters are of legal age.
Chapter One: Bored and alone.
It was Saturday night and it was getting late. I had watched COPS for an hour, having gotten my weekly dose of schadenfreude from watching people with lives even more miserable than my own have theirs go down the tube in front of the whole country, and now I was sitting in front of the computer finishing my final beer of the evening.
I wasn't looking for anything in particular, but was just skipping around from site to site, hoping to make my eyes tired enough so that sleep would come easier for me. That was what my life had been reduced to after my wife passed away a couple of years ago at the age of 53.
After she died, I lost interest in much of everything. Sold our house and got rid of most of all the stuff we had collected over the years as well. So now here I was in a very modest studio apartment, pecking away a keyboard. For the hell of it, I visited a dating site and scrolled through a bunch of pictures of people, hoping to find someone that I knew.
For some reason, the prospect of seeing a familiar face there had always interested me, and was what had probably kept me from putting my own picture on one of them. To me, it seemed like an act of desperation to do that. Whether my reluctance to do that meant I wasn't desperate enough yet, or had gone beyond the point of desperation, was something I wasn't sure of.
I was just about to move on to somewhere else, perhaps to go read a story at literotica that would move me enough to have a goodnight wank, when a picture caught my eye. I clicked to enlarge it, and found myself fascinated by the woman. Fascinated enough to read her profile that accompanied the photo.
"Not a very discriminating woman," I said aloud as I examined what qualities she was looking for. Apparently she was looking for a man of any race, height or weight aged 18 to 99. The brief note attached said only that she was very shy and was looking for a nice man.
"I'm your man," I noted as I examined the picture closely, and the more I looked at the girl in the photo, the more aroused I got.
I'm betting that the chances are good that most other guys that had ever stopped at her image had got an erection from looking at this woman's picture, but I'm not most other guys. I've always had what most people would consider a contrary view on what type of woman I found attractive.
Jan or Marcia Brady? Jan in a landslide. Mary Ann or Ginger? Not even close. I thought that Adrian looked hot when she worked at the pet store in the beginning of the movie "Rocky". For whatever reason, the more plain and awkward a woman was, the more they turned me on.
Maybe it was because they weren't as full of themselves as the classically attractive women often seemed to be. Perhaps it was because I'm no Brad Pitt myself. My late wife was probably considered plain at best by most people's standards, but she excited me from the first day we met right up until the end.
This woman didn't look like my wife, so that wasn't what attracted me to the photo. This girl wore thick glasses and had a facial expression that made her look like she was in pain. She had thick, bushy eyebrows and mousy brown hair that went down to her shoulders.
She had posed next to a fence, wearing a shapeless sweater and slacks, and while it was tough to get any sense of proportion from that, she seemed to be above average in height and skinny. It was almost as if whoever had taken the picture was trying to make her look as unappealing as possible, and judging by the length of time her ad had been on the site, it apparently had worked.
For the heck of it, or maybe because of the encouragement of the alcohol, I answered the ad. I told her that I found her quite pretty, and thought I had the qualities she was looking for, namely because the only qualifications she had set down were to be a nice guy between the ages of 18 and 99.
After replying, I promptly forgot about it, until a few days later when I got an e-mail from someone whose name I didn't recognize.
Chapter Two: I'm Gail.
It took a minute for me to figure out who this person was before it finally registered. The girl from the ad. She had replied to my response to her ad, and said that I seemed like a nice guy and would like to meet me.
Her exact response was...
"Hello. My name is Gail. You answered my personal ad. You seem like a nice guy. If you want to meet me, tell me what day and time and I will meet you at the mall."
Nice guy? All I had done was to tell her that I thought she was pretty and that I fit all the qualifications she had set forth in her profile. There were no qualifications, so how she thought I was a nice guy from that was baffling.
She didn't even seem to want to know anything about me, only offering to meet me at the mall. I was fully prepared to tell her everything she wanted to know with complete honesty, and after I did that I would have expected her to run for the hills.
What would I have told her?
"Hi Gail. My name is Chuck. I'm 56 years old which means I'm probably old enough to be your grandfather. I haven't been laid in almost a year and I'm so horny that the crack of dawn looks good to me. I like homely girls because they turn me on and because they aren't used to having guys make runs at them, and I'm not particular about age or the looks either. Only the gender.
What do I want to do on a date? Besides going to a movie and having dinner? Besides having a nice conversation and finding out all about each other? Hell, I want to kiss, neck and have sex. On my perfect date I'd love to eat pussy and have my cock sucked. I don't really need an extended courtship. I'm pretty easy in that regard. Let's just get in bed and go nuts. The rougher the better, too."
Well, maybe I wouldn't have said it in those words, but if she could read minds that's what she would have learned. So I answered her, telling her that I would be at the mall on the bench in front of Friendly's at 5 Saturday afternoon, wearing a green cap.
Gail said fine.
Chapter Three: Meeting Gail.
I saw her first, I believe, even though I was only going by the memory of her picture. She was walking along the fronts of the stores as she headed toward Friendly's where I sat waiting as promised.
Her glasses were so thick that she probably couldn't see all that well, and as she got closer, I learned that the picture hadn't been insulting to her, but might have even put her in a good light.
She was a combination of Rocky's Adrian, Jane Hathaway from the Beverly Hillbillies, and Ugly Betty. She looked meek and almost terrified to be out in public, as her head darted around at every sound in the crowded mall.
What was my reaction to seeing this train wreck of a girl for the first time in person? I was hard as blue steel. Our eyes met briefly when she approached the entrance of the restaurant and looked my way, but when she saw me she quickly looked away and kept walking.
"Oh well," I said aloud as Gail skittered down the mall walkway and out of my life.
I mean, I know I'm not Brad Pitt or anything, but I'm not that bad looking, even if I do look a little scary. I look a little like Patrick Stewart from Star Trek, but I'm 6'3" and about 240 pounds, and because I work construction I'm still very fit for my age.
So when this girl went running away, I figured that I had hit rock bottom. When women like this Gail run away, I guess it may have become time to stay home and spend my remaining years jerking off to porn.
While I sat there and contemplated my next move, I happened to look up for a minute, and when I did, I saw the reflection of Gail in the glass of the store window. She was on the other side of the mall behind me, looking at me as she walked slowly around the circuit.
Well, well, well, I thought. Isn't she clever? Checking me out like that, and the very thought of it brought my hard-on back. There was hope for me after all, so I stayed on the bench and waited. And waited. And waited some more.
Finally, I saw her coming around again in front of me. This time I pretended not to notice her, figuring that she would be less nervous than if I was sitting there leering at her like the Big Bad Wolf.
Here she comes... and there she goes, walking right on past again. I started laughing as she went down the length of the mall again, and was not surprised at all when I saw her reflection once again as she walked behind me.
This was cute, and I was enjoying it in a strange way, but it was getting a bit old when she did it yet again, so after she made the grand circuit once again, I decided to end this and get down to business.
After she passed behind me and went down to the far end of the mall again, I got up and ducked inside of Friendly's and waited for her to come around again. This time, when she saw the empty bench, she looked around, her head darting from side to side as she tried to figure out what had happened to me.
"Hello Gail," I said as I came up behind her, and her purse flew out of her hands as she jumped in shock.
I helped her pick up the contents of her purse, which consisted primarily of a bunch of rolls of life savers that were in various stages of fuzziness and size, and handed the stuff to her as we rose.
"Sorry," I said. "Didn't mean to scare you. I just got dizzy watching you walk around the mall like you were."
"Oh," Gail said, mumbling into her jacket.
"Didn't like what you saw, or couldn't make up your mind?" I asked in as soft a voice as I could manage.
"Dunno," Gail mumbled.
"Well, would you like to get a bite to eat or something?" I offered, gesturing toward the restaurant.
"Okay," Gail said, and as I escorted her inside, I shook my head in disbelief, wondering if the 3 words I had coaxed out of her so far was any indication of what I was in store for.
Chapter Four: Gail talks.
Gail took her jacket off, but the shapeless sweater gave few hints as to what was underneath, except that there didn't seem to be much. That was fine by me, because I have never been much of a breast man. Just a handful, or even a mouthful was fine by me.
Gail's fingers were skinny and the nails looked like they had been chewed very short. Her hair was medium brown and fairly long, and she had big teeth. Her glasses dominated her face and obscured her thick bushy eyebrows, and the specs sat on the bridge of a nose that was a little on the large side.
"So, Gail," I said as she perused the menu. "How many times were you going to walk around before you came up to me?"
"Dunno," she said. "Never did nothing like this before."
"Plus, you didn't know my name," I added.
"Yeah, I forgot to ask."
Eureka! A more than one word answer. I liked the shyness of the girl, and her looks were growing on me.
"Well, my name is Charlie - Chuck if you prefer."
"My name is Gail."
"I know," I told her. "How old are you? You're 18 I assume."
"No," Gail said, and a wave of terror washed over me as I looked around for Chris Hanson and the ambush cameramen. "I'm 20."
"Oh good," I said with great relief. "Want to know anything about me?"
"I dunno," Gail shrugged. "You're big. Tall, I mean, and you look like you got lots of muscles. Kind of scary looking."
"Well, I'm 6'3" and I guess I am rather strong, but I would never hurt you," I assured her. "The scary part, well, I guess I can't help that."
"You look like that guy on the TV," Gail said, seeming to rack her brain trying to remember who she meant, before her eyes lit up.
"Mr. Clean!" Gail announced with great joy.
"Oh, well, I guess that's not too bad," I said. "Could be worse."
"Yeah, he cleans stuff good," Gail informed me. "We use his stuff at work."
I managed to discover that Gail cleaned offices on the midnight shift, so things were really picking up on the information front. I soon found out that Gail liked cheeseburgers too, since that was what she ordered.
"You look like somebody too," I said. "Let me think for a minute."
"Guy at work told me that I looked like Julia Roberts," Gail opined.
"Really?" I mused, trying to figure out how in the world Gail would look anything like the star of Pretty Woman.
"I think it's because I got hair under my arms," Gail informed me. "One time he peeked down my sleeve and saw it."
"Oh," I said, and while being a child of the 60's, that sort of thing not only didn't bother me in the least but in fact made her more interesting, it seemed to be a lot of information to lay on someone so early in our relationship.
"I was thinking more along the lines of Shelley Duvall," I said. "She was in "The Shining"."
"Oh, I know her. She was in "Popeye" too," Gail proclaimed proudly. "Don't know if she has hair under her arms or not though."
"I don't remember," I answered, almost choking on the water I was drinking. "Maybe she shaved hers."
"I suppose," Gail said. "I wasn't allowed to."
"Really?" I asked. "Is that for some religious reason?"
"No," Gail replied in a matter-of-fact manner. "Daddy wouldn't allow it."
Chapter Five: Gail and Daddy.
"Oh," I answered, grateful that our food arrived before the resulting silence got even more uncomfortable than the conversation had been.
"You're old, aren't you?" Gail said between bites of the burger that she attacked with vigor.
"56. Is that too old for you?" I asked.
"No. My Daddy is 58."
"Your father seems to be a big influence on your life," I said.
"Yeah. He's not around anymore."
"Oh, did something happen to him?"
"He's in jail," Gail informed me.
"Jail?" I choked out. "Why is he in jail?"
"He got mad at somebody."
"He's got a powerful temper."
"I see," I answered. "So, you live with your Mom?"
"No, she went away a long time ago," Gail said. "Dunno where."
"So you live alone?"
"Yep," Gail said, polishing off her burger and looking for the waitress. "I think you get a free sundae with this meal."
"Sure, you can have one either way," I said, enjoying the glint in her eyes as she ordered her ice cream with extra sprinkles.
"I'm glad you snuck up on me," Gail announced. "Else-wise I would have just gone home."
"I'm glad I did too," I told Gail. "Have you met other men from this dating website?"
"No, I just got a computer a few months ago. No way Daddy would let one of them in the house, and he would kill me if he found out. You're the first man I actually met. I had a few other guys come up to the mall, but..."
"You walked around in circles until they left?" I asked, and Gail nodded.
"I was kinda afraid to meet them."
"So you don't date very much?"
"Does this count as a date now?" Gail asked. "Because if it is then this is the first one I've ever been on."
"Your first date?" I exclaimed. "Ever? Not even back in school?"
"Heck no," Gail said. "Daddy wouldn't let me date nobody."
My cock surged in my pants as I thought of the possibility of getting into some pristine territory. A virgin!
"He was strict, I take it?" I asked.
"Oh yes," Gail said, her spoon rattling as she dropped it into her empty sundae dish. "Strict and jealous."
"So then I guess that means you were Daddy's little girl?" I suggested. "I suppose that means that you've never been out with a man before?"
"Is this a date?"
"I suppose you could call it that," I said.
"Then this is the first."
Chapter Six: More with Gail.
"That seems strange," I said. "A pretty young gal like you not going out with guys."
"I'm not pretty," Gail said glumly.
"You are to me," I opined. "Beauty is in the eye of the beholder. Haven't you ever heard anybody say that before?"
"Not to me."
"Well, I might be old and scary looking, but I am honest, and I find you very attractive," I said, enjoying seeing a little color rise in Gail's pale complexion.
After we left the restaurant, we walked around the mall for a while. There were no movies playing that Gail wanted to see, but thankfully, as we walked Gail became more relaxed and the conversation improved greatly.
When we first started conversing at the restaurant, I initially thought that she was either mentally challenged, or at the very least, what we used to call slow. All of the monosyllabic answers and odd references led me down that road, but as we kept talking, I learned that wasn't really the case.
She didn't have a speech impediment, and wasn't a dullard. She was just very nervous and painfully shy. It was like she had been locked in a cellar all of her life, and had just recently been let out to see the world. Sadly, that wasn't really far off the mark.
"Did you have a good time?" I asked as I watched the stored starting to close around the mall.
"Yeah. You're a nice man."
"Just like I told you," I said proudly, not believing that I had just spent four hours with this girl, and that the time had not dragged at all.
"Would you like to go out on another date?" I asked.
"Really?" Gail answered, with a look on her face that suggested I must be crazy.
"You said you had fun," I said. "Maybe next week?"
Gail agreed, and after not giving me her phone number, claiming to not have one, she also declined my offer of a ride, saying she had driven.
Gail also didn't want me to walk her to her car, saying she was parked way in the back, so I settled for a handshake at the mall entrance. As we shook hands, I leaned forward and gave Gail a kiss. Not anything major, just kind of a peck on the lips. She seemed shocked, but smiled afterward, and actually said thanks before heading out to the parking lot.
I watched Gail walk through the lot, and she kept looking back at me for some reason. I ducked out of sight, thinking that she must be really paranoid or something, not wanting me to see her car license plate number or something.
Suddenly, just before I started to walk back through the mall to my car, I saw Gail darting between the cars. I figured she might have forgotten where she parked, and having done that a few times myself I could understand that.
Instead, she went over to the bus stop and ducked into the glass enclosed waiting area out in the center of the parking lot. My first instinct was to go get her and insist on taking her home, but I thought that might freak her out, so instead I went to get my car.
After starting to drive home, I decided to drive around to the bus stop, just to see if she was still there. As I approached the kiosk, I saw her getting on a bus along with a bunch of other people, so just for the heck of it I decided to follow the bus to see where she got off.
Stalking? Maybe, but I had no evil intentions, and was just curious as to why she was being so secretive. The bus headed downtown, and it was a slow and stop and start journey, but it wasn't like I had anything else to do, so I kept at it.
The bus kept going and going, and headed into areas of the city that I hadn't been in for many years, and with good reason. Her trip had started in the suburbs and went into what might be politely called a depressed area, finally ending in an area that seemed to fall in a category well below ghetto.
I watched from afar as Gail walked down the depressing street before disappearing into a house that didn't seem fit for human occupation. The ride home for me was not a happy one, and it wasn't because I thought anything less of her for living where she did, just because I felt bad for her.
Chapter Seven: Date number 2.
Our method of conversation became e-mails, and we chatted all during the week and got to know each other a little more. We arranged through e-mails to meet at the mall that next Friday, and this time when she saw me she came right up to me instead of circling around. When I mentioned that, Gail giggled and shyly buried her chin into her jacket, making her look more adorable than ever to me.