Starting Over

After a lousy night's sleep and an even lousier breakfast at the homeless shelter on Baker Street, I knew that I needed to find work and a place to live, and find both quickly. Arriving the day before in a freight yard near Baltimore harbour after riding all night in the end of a hopper car, I was completely filthy. I'd managed to get most of the filth off my face and hands by washing in a public toilet but there wasn't much I could do about my clothes - at least not until the nearest Salvation Army store opened. At the shelter, the night porter or gate keeper or whatever he was called, had taken my name and given me a cot number and instructions that breakfast would be at 7:30, and afterwards I would have to leave by 8:30, rain or shine, sleet or snow, hell or high water. No, there would be no help from that arrogant sourpuss.

It was at that point that I even started questioning whether it had really been necessary to run away from Chester and the comfy situation with Ellen and family. Would the mob types from the club really pursue me? Taking a job below minimum wage, no bank account, no ID, they had to know I had a shady background. But how shady? In retrospect, I realised and accepted that they couldn't be sure I wouldn't go to the law and try for a deal. Yeah, running had been the right thing to do.

As I was leaving after the 'breakfast', to my surprise and relief, sourpuss was not in the reception cubicle. Instead in his place was an elderly couple with name tags indicating the church they belonged to and their names: 'John' and 'Martha'. John, a quiet reserved type whose face I couldn't even begin to read, looked the part of a retired bureaucrat. Martha, on the other hand, seemed to be one of these caring sympathetic types (some folks would say a bleeding heart) or maybe she was just skilled at looking that way -- over the years I'd seen all types.

I turned to her and got her eye before opening with a thanks and "Miss Martha, I know it's not your job but I'm just trying to get back on my feet. I know how to do lots of different kinds of work around houses and gardens. You must know somebody who needs stuff done -- like gutter cleaning, clipping, mowing, painting, repair. Heck, I can do lots of kinds of home repair work and construction, I just don't have tools or transportation."

"And you don't have a social security number or drivers license either?"

So Martha had been around the block a time or two. I gave her a look that said she had read me correctly.

"Well do you have a name?"

"Art."

"And a last name?"

"Chester. Art Chester, you know like the 21st president's except in reverse order and without the 'A' in the middle."

The night porter had surprised me when he'd asked for my name and I'd fallen back on my old system of using the name of some city where I'd been -- 'Chester' in this case. When he'd asked whether 'Chester' was my first or last name, I decided to say it was my last name because Chester as a first name sounds a little fancy for a guy sleeping in a homeless shelter. And the 'Art' I did get from the 21st president's last name. I've used lots of systems to remember my phony names -- when I was in Chester, Pennsylvania, I used 'Al' as a first name. Why? The letters 'A' and 'L' are short for 'at large', which as a bail jumper, I was.

Martha: "Well we don't need anything right now at our house, but let me think a minute. Oh, why don't you wait outside and maybe I can think of something."

So I waited outside on sidewalk. Maybe something would turn up. It must have been around nine when the two of them came out and I got up and looked expectantly at Martha. She turned to me and said to meet them in the parking lot around the corner on Mountmore in 10 minutes. I knew I was in luck because she was supposed to just say they weren't allowed to arrange jobs for 'clients'.

In the parking lot, Martha was standing next to the passenger side of the car, her husband John was sitting behind the steering wheel. Obviously she was the arranger and doer in that marriage.

"My friend Lisa has a home that she's having trouble keeping up. Right now she says the gutters have been overflowing and there's some other stuff wrong. You wait here. She'll come by for you in a half hour or so. You'll have to mention our names so she knows who you are. Oh yes, and be sure to use the same name that you gave me and remember which one is the first and which one is the last name."

I agreed, at the same time ignoring her barb. What else was there for me to do? Guys like me have to eat a lot of shit along the way. Then I sat down on the curb to wait.

Sometime later, a light blue Ford sedan stopped and the lady driver with grey-streaked black hair put down the front seat window and looked at me.

"I'm Art. You must be Lisa. John and Martha told me to expect you."

"That's me. Hop in Art."

The drive to her house didn't take as long as I'd expected and not much was said on the way. When we got to her house - a two-story brick bungalow like they built in eastern and mid-western cities in the late 40's and 50's - I saw right away that the place was an example of deferred maintenance. The lawn was mowed but it looked like some kid had done a 'lick-and-promise' job of it. Lisa showed me where the gutters had overflowed and showed me the ladder in the garage. Being a bungalow design, the gutters were only around 16 feet up so it was easy with the ladder. There were lots of rotten leaves and dirt in the gutters and from the way it clung to the gutter bottoms, it looked like they hadn't been really flushed out for years. After I got most of the stuff out, I told her I needed a long hose for flushing.

"The company that cleaned them last didn't need a hose."

"They needed one but they didn't use one. That's part of the problem."

Her hose wasn't long enough so we borrowed from a neighbor and I spent another half-hour or so flushing the gutters and then realised that the downspouts were backing up. One was so badly blocked, I had to take it all apart to get the crap out. By the time I got the gutters all cleared and clean, it was around noon and Lisa told me to come in for lunch. Over a lunch of bread and cold cuts and salad, she asked if I could make her lawn look better.

The sad sack who'd been mowing for her had missed spots and hadn't even tried to get close to the hedges and edgings. I got out the mower and mowed the whole thing like it should have been done in the first place. Then I went to work with the grass shears. Lisa came out of the house and asked where I kept the rest of my clothes -- mine were already pretty sad looking when she picked me up and cleaning gutters sure hadn't helped. After I told her she was looking at my whole wardrobe, she asked my sizes and said she'd go to the Salvation Army store and get me some spares. I was pulling weeds from the flower beds when she came back with several pairs of jeans, a couple shirts, underwear, socks and even a denim jacket. She asked me to come in for coffee and said I should shower and change into some clean clothes. I guess I must have really looked pretty ragged and smelled bad if she wanted me to shower and change before finishing work. I was glad there was a real man's shower in the basement so I didn't have to fuck with a bunch of fancy rugs and cosmetics and towels and shit like most women have in their bathrooms.

Over coffee Lisa tried to find out where I came from and how I got so far down and out. Evasive as usual, I answered in generalities and deflected her questions with questions of my own. She wasn't very forthcoming either but I did find out that she was separated from her husband and that they had two grown children in their late 30's -- one living in living in Ohio and the other in Arizona. The age of her kids surprised the hell out me because I'd estimated her to be 50 to mid-50's. The age of her kids would put her a lot closer to 60. (Later on she told me she was 66.)

Around five, she had me quit and paid me $90 for a little less than six hour's work. I told her I could paint and pointed out the peeling and faded paint on the garage door. Actually all the window frames and trim were in bad shape too, but I would keep that for tomorrow. We agreed that she would collect me at the shelter the next day early so she could give me a real breakfast. Lisa even said I should just leave my 'new' clothes in her house and said she was sorry that I couldn't sleep in her basement (because the neighbours would talk).

The next morning after breakfast, we went to a Lowe's store and bought paint, brushes, sandpaper, sanding block, putty knife and a razor edge scraper. (Her husband must have done absolutely nothing on and around the house because his tool collection was not much more than a hammer, pliers and some screwdrivers.)

Lisa was really surprised when I was done prepping and priming the garage door by around ten. I could almost see the wheels turning in her head as she calculated how cheap she could get all the window trim painted and sure enough, before the primer on the garage door had dried, she said I should start prepping the windows. Now I knew I had several day's work at least and I figured there'd be more by referral.

That afternoon a woman in a white Mercedes coupe parked in front and as she walked up the sidewalk, complimented me on the work I'd done and was doing. Lisa asked her in and around a half hour later, Lisa asked me to join the two women for coffee. Jolene, the friend, was one of these women that you first take to be in their thirties but up close, you realise that your estimate was around 20 years too low -- in other words, she was a damn nice early 50's and dressed very stylishly and tastefully. She also gave the impression of being a no-nonsense business woman - an impression turned out to be very correct. Several times as we were having coffee, out of the corner of my eye, I caught her giving me an appraising look.

Right from the beginning, Lisa had been very correct towards me, although at the same time, somewhat standoffish. After Jolene's visit, Lisa did seem to be more cordial, sometimes it seemed to me that her cordiality even bordered on flirting.

The rest of the week went pretty much the same. Lisa would collect me at the shelter, give me breakfast and I would get in a full 8 hour day. By Friday afternoon I had prepped all the ground floor windows and I was more than $400 richer than I'd been on Tuesday morning and I thought that by Saturday night, another $120 would come on top of that. Talk about a good story for Forbes magazine, I could see the headline: 'Arthur Chester Increases Net Worth 8-Fold in One Week!'.

When we got to the shelter, she told me that she wanted me to help her with something else on Saturday. It turned out that Lisa wanted to go to some kind of artsy furniture flea market in Hagerstown and she wanted me to go with her -- she'd pay all expenses and give me 50 bucks besides. What the hell, I didn't have anything else lined up for Saturday anyway and it'd be nice traveling without running away from somewhere or somebody.

So the next morning she collected me early and on the way to Hagerstown, we had a super breakfast at a Holiday Inn on the way out of Baltimore. At the flea market we walked and looked and walked and looked and by around one in the afternoon, she decided on an old mirror to hang in her upstairs hallway. At lunch in Hagerstown, she sprang the next surprise on me.

"Art, we don't really have to get back today. I know a nice little B&B along the Potomac over in West Virginia. You'd sleep better there than in that Baker Street shelter. How about it? It'd be so nice to stay out of the city a little longer."

Well what could I say? She had the car and she had the money. So I said the only thing I could: "Lisa, I don't have a toothbrush or a shaving kit with me."

"They sell stuff like that here too. Any more excuses?"

At the B&B, she went in alone to see if they had a room. A few minutes later she came out and announced that they had one left - with twin beds.

As we settled in to the room, I was a little surprised at how much travel stuff Lisa 'happened' to have in an oversize handbag that 'happened' to be in the trunk of her Ford. She thought to explain: "Oh, I've sort of made a habit of taking extra stuff along when I go on these little shopping excursions."

After dinner at a local restaurant, we went for a walk along the Potomac and got back to the B&B about the time it got dark. Lisa took a bath and came out in a light blue mid-thigh length sleepshirt that had 'happened' to be in the handbag that she had taken along out of habit. It was obvious that she had taken some time with her hair and body and the air in the room was laced with the scent of an enticing perfume that I couldn't ignore.

She had to notice my look and I thought she was about to signal me to join her in the other bed but instead she simply said very sweetly: "Art, the shower is free. Oh by the way, I brought these along for you." With that she handed me a pair of boxer shorts and a tee shirt that 'happened' to be in her handbag.

Glad to be able to put on clean underwear and with the beginnings of an erection, I went straight to the bathroom and showered, using lots of cold water to get my erection under control. Coming out in my fresh underwear and holding the soiled stuff over my front to hide my partial erection, I found Lisa sitting up in her bed, covers up to her waist.

"Art we need to talk."

I took a step in the direction of my bed and she said sweetly "Just so we don't have to talk too loudly, in this bed, if you don't mind."

At that I gave up trying to hide the bulge in my shorts and slid under the covers beside her.

"First of all Art, you don't have to hide your erection from me. I'm 66. At that age a woman is really honored to give a man an erection. So let's just put the covers down and be open with one another."

We turned the sheet and blanket down to our thighs but not before I got completely hard. I must have misaligned my shorts because just like that my pecker popped out of the pee slit. I heard her catch her breath and was about to put my hand under her sleepshirt when, with a panting whisper, she says "Art, the second thing is that, well you know I'm 66. Women my age don't get wet down there so easily."

I mumbled something about being an understanding sort of guy and she came back with "But Art, all the same my hands are actually better than ever. Why don't you take off your shorts and make things more open for me?"

I barely got my shorts down past my feet and she was already sitting up and holding my balls in one hand and gently stroking my throbbing dick with the other. In no hurry whatsoever, she continued with a slow stroking, alternating her gaze from my groin to my face, she seemed intent to drag my foreskin as far forward over the head as possible, holding slightly and then back down. Obviously she wanted this to last and there was no hurry because when it seemed that I was on the way to the top, she nearly stopped, just lightly holding my dick and balls. Then she would look at me with a sly smile and resume the slow stroking. All the while the tension kept building in me and I finally begged her for the release. She turned to the bedside and pulled a packet of tissues out of the handbag. "I told the host that we are sister and brother. It wouldn't do if they found stains on the bedding, would it?"

My look must have said 'I couldn't care less, just keep up the good work' because she didn't waste time resuming the hand job. Holding some tissues in her left hand a few inches over the end of my dick, ready to catch the expected fountain, she resumed stroking my dick with her right hand, faster and faster. Her breaths came faster and louder -- actually panting and emitting sharp little moans. My knees raised slightly and my legs stiffened. Lisa bent over so she could watch the semen come out and then it came. The look on her face told me she was enjoying the volcano-like spectacle. Before I even got completely soft, she was cleaning me up and I could see that she enjoyed that too.

Afterwards she lay down next to me and pulled the sheet and blanket back up. "Art, your cum is really strong, I could feel it splatter right through the tissues. You must have really needed that. Has it been a long time?"

I couldn't very well tell her about what happened barely a week before so I just gave one of my non-committal replies "Lisa, you can imagine my social status wouldn't exactly lend itself to me making a big splash in the dating scene."

"It must be tough sleeping in shelters, all those cots close together. I mean you can't even masturbate. Oh sorry, I didn't mean to get into that. I just can't help being curious about you."

I knew it was time to steer the conversation in another direction. "Lisa, you said you don't get wet down there so easily. Did you get wet down there just now?"

"Maybe a little. Why don't you check it out?"

I reached under the sheet and put my hand between her thighs, which quickly parted. Working my way, up I found moist outer lips, which I stroked lightly before exploring the rest of her hairy vulva. Stroking her clitoris brought forth sharp breaths and soft moans. I worked my finger in between the inner lips and even before I fully grasped that they weren't ready, she whispered: "Wait Art, let me give you something."

Again she reached into her magic handbag and came out with a tube. "Hold out your finger." She squeezed some jelly onto my outstretched finger and asked the rhetorical question "Do you know what to do with this?"

After repeating what I did before with the outer lips and clitoris, I went in and gently massaged her inner lips, which then got looser and seemed to generate some lube on their own. Lisa was now breathing sharply and moaning ever so softly. I had the feeling that this was something she hadn't had for some time. I touched the entrance of her vagina, but finding it still dry and tight, I backed off and resumed my massage of her inner lips.

"Al, please hold out your finger again."

I did and then with my KY jelly laden finger, I worked my way in to her vagina. When it responded pretty quickly, I followed with a second finger. Her squirming and panting didn't go without effect on me and I now had a pretty fair hard-on. When I made a move to get on her, she stopped me.

"Please Art. I want it very much but I want to be careful. Please understand, it's nothing against you." Again she reached for the handbag and this time I knew what she'd be taking out.

She handed me a small foil envelope. "Okay?" she asked.

I answered by ripping open the pack. Hell, I might have a shitty place in society, but all the same, I don't want to get AIDS or any other nasty shit either.

"Art, you hold the end and I'll unroll it." She didn't fumble one bit, just smoothly unrolled the condom and then after putting a little KY on it, "Well, it looks like we're both ready."

On my knees between her legs, I quickly got the head in between her lips, getting a nice sharp gasping response from her. "Don't spend too much time there, I want all of you."

I went on in slowly and she quickly loosened up. She responded to my thrusting, at first with moans and gasps and then also by thrusting back. My mind was buzzing with the anticipated release inside female warmness. Things were getting wilder but despite how wild things were getting, she suddenly thought of the mess we'd be making on the bedding. "Art please get a towel for us to be on!"

Ever the obedient and disciplined handyman, I got a towel and slid it under her and quickly resumed our fucking. Towards the end, I held her by the hips, her ass was off the bed and both of us came at nearly the same time. Now all sweaty and nearly out of breath, we collapsed together on the bed. My soft dick was still in heaven's folds and I was thinking that an internal recovery might be in the cards.