A New Job

Info trailmate
27 Oct. '18

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 myself a job and a place to live and find both quickly. Arriving the day before in a freight yard near Baltimore harbor 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.

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 nametags 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?”


“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 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 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 ‘residents’.

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 has trouble keeping up. Right now she says the gutters have been overflowing and there’s some other stuff wrong. If 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 the 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 realized that the downspouts were backing up. One was so bad, 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 so 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 guessed her to be 50 to mid-50’s. The age of her kids would put her a lot closer to 60 – it turned out that she was actually 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 neighbors 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 realize that you are around 20 years off – 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 and that impression did turn out to be 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 come 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 Lisa “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. As wild as 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.

Lisa recovered first: “Art, the rubber! It might come off inside me.”

I lifted up. On my knees with a limp dick hanging, the weight of the overfilled receptacle was starting to pull off the condom. Lisa ever the alert one and always ready with the right words: “Looks like we caught it in time.”

She took off the condom, packed it in a tissue and then wiped both of us with tissues.

Afterwards we lay close together under the sheet and blanket.

I kept thinking about how she’d planned it all – the ‘day’ excursion to the flea market that ended with us in bed in the B&B. The handbag that ‘happened’ to be in her car and ‘happened’ to contain my underwear, her toilet articles and night shirt, condoms. Should I be glad or worried?

Then something else occurred to me – the condom had fit pretty well. “Lisa, how’d you know my size?”

“Oh Art, I have to confess. When you showered at my house. Well, I peaked through the keyhole.”

“But still, you couldn’t really measure?”

“Art, there aren’t that many condom sizes. Besides, I saw right away that you were bigger than my husband so I picked the next bigger one.”

Now that surprised the hell out of me. She was surely 15 to 20 years past menopause, separated from her husband and she still knew his condom size! “You mean your husband and you, I mean you still…?”

“It’s complicated. He had some girlfriends and then, well mainly it’s because he was in prison and well, you know what can happen there.”

I could see she really didn’t like the subject of her husband or ex-husband, whichever it was, so I dropped the subject. We had a good sound sleep and got it on again early the next morning. Fortunately she had more condoms and tissues in the handbag and the host had been generous with the towel supply.

When we walked into the B&B’s breakfast room, the host and the other guests gave us smiles and knowing looks. Then it hit me that the room-to-room and upstairs-to-downstairs sound proofing probably wasn’t anywhere near recording studio quality and our night and morning thrashing in bed must have been heard by all. Lisa’s face got red and I thought she might turn around and want to leave. To take the edge off, I just started talking about the nice walk we’d had the night before and what a fine day it was.

The guests couldn’t have known that we were registered as brother and sister so they would have just thought we were an older couple having a secretive affair. The host on the other hand must have been wondering about an older brother and sister pair getting it on together. I really didn’t give a shit, I’ve got other worries when it comes to people wondering who I am.

On the drive back we talked about the work at her house and she mentioned that her friend Jolene might find an affordable place for me to rent. In fact she thought Jolene might even have a job for me.

Then out of the blue, she asked me “Art what do you do about medical care? I mean you can’t just go to an emergency room and ask for a checkup.”

“If you get injured, they have to fix you. About five or six years ago, I smashed a finger on a job. In the ER, I asked the doc a few other questions and together with the blood tests, it was sort of a checkup.”

Then she surprised me again: “I figured as much. Look, I hope you won’t be mad but I made an appointment for you tomorrow morning. Don’t worry about the cost, I’ll take care of it.”

“Jesus Christ, Lisa!”

“Jesus is not responsible for what I did! I did it all on my own and with good intentions!”

I mumbled something or other about being in charge of my own life but she cut me off with “Besides I’m getting a good deal with the work you’re doing so it’s not like charity! Oh and by the way, the doctor’s office won’t ask you for an employer’s name or address.”

I didn’t respond and it was quiet in the car for the next half hour or so. Then she dropped another bomb on me – this one a lot more to my liking: “Art would you mind spending the night at my house? Then I wouldn’t have to drive you back to Baker Street and collect you again in the morning.”

“And the nosy neighbors?

“Oh you can just hunker down in the back when we drive up and again when I drive you to the doctor’s office. Really, it’ll be okay.”

I protested about the potential for trouble but she sweetened things by telling me that she had more condoms in the bag and we wouldn’t have to face knowing smiles at breakfast. I didn’t have to consider very long and I complimented her on the good idea.

Back at her house she didn’t delay drawing a bath and made it clear that it was for both of us. I was rock hard before I even got in the tub with her and this really pleased her because she couldn’t seem to play with my dick enough, always backing off when it seemed I was ready to come. Finally when there was no more holding back, she held my dick so that I squirted all over her chest and chin. Afterwards we went to bed nude and carried out the same routine as in the B&B with KY and condom – albeit with a lot more abandon because there was no one to hear us.

The next morning we left the house with me tucked down in the back of her Ford. The doctor’s office was in a group practice. Lisa told me that I only had to give the reception my name and tell them that I had a 9 AM appointment with Dr. Henley.

“Oh yes, Mr. Chester, you do have a 9 AM with Dr. Henley. But first you need to go to the lab. When they’re done, come back here to this waiting room.” After parting with lots of little vials of blood and pissing in a cup, I went back to wait. I didn’t even get past the contents page of Time magazine when I heard a sweet voice saying “Mr. Chester, Dr. Henley is ready for you.”

Looking up, I saw a cute blond, maybe 5-2, slender, smallish breasts and wearing white scrubs. Her name tag said ‘Karen’. She showed me into an examination room, wrote some stuff on a form and measured my blood pressure and pulse. She told me Dr. Henley would be with me shortly and just as she was about to leave, she told me to strip to my shorts.

Dr. Henley turned out to be a tall, maybe 5-9 or more, sturdily built, mid-50’s woman with brown-gray hair tied back in a bun. All business, not wasting time with pleasantries, she got right on taking my medical history: sicknesses, injuries, operations, whether I could piss well, you name it. Then the usual listening to breathing and abdomen noise, tapping on my knees and elbows with her little hammer and so forth.

I was expecting it but still it still sent a little shiver down my spine because I have a hell of a time not getting a hard-on when I’m naked in front of a woman and I really hate having a finger stuck up my ass. Then she pulled on a pair of latex gloves and said “Stand up and drop your shorts.” Finger in my bag each side and cough. So far, so good, no hernia and my dick was still hanging. Then I had to bend over, head on the table and spread my cheeks. I’d had my rear end inspected before but she seemed to go at it a lot more thoroughly than other docs. Afterwards, she snapped off the offending glove and said everything looked good – whatever that meant.

Then came the surprise: “Now Mr. Chester, I need you to lay on your back on the examination table.” I gave her a questioning look and she said “Just put your shorts over there with your other clothes.”

Then over the intercom, she says “Karen, could you come in here please.” And to me she asked in a tone that wasn’t asking “You don’t mind having my aide in here do you?”

Now two women would be looking at my bared crotch so I’d have to double my efforts at staying under control. But double was not enough, Karen the aide was barely in the room and I was already at half mast. Then they were on opposite sides of the table looking at my crotch and it only took the doc to tell her to retract my foreskin as far as possible and I was standing out like a flag in a force 7 gale.

Karen pulled on gloves too and tugged my foreskin all the way to my groin as ordered and the doc, now with new gloves on, examined my tool from end to base, prodding with her finger, sometimes squeezing, face very close. My hard-on was raging and I had to work to control my breathing. Then “Karen, pull Mr. Chester’s foreskin as far forward as it will go.” Then another close exam.

Dr. Henley made a few notes on the clipboard and then looked at Karen and said “Well since Mr. Chester is already erect, we’ll do the erect measurement first.” From a drawer, Karen took out ruler-like instrument – essentially a ruler with a sliding stop and with a half-ring on one end. The half-ring went against me just above the base of my dick and with the ruler against the shaft, Karen moved the stop to the end, took the apparatus away and read off the scale: “Wow, Mr. Chester is 7 and 3/4 inches erect!”

“Karen, this is a medical practice. I think we can dispense with emotions.”

“Oops, sorry.” Then using a cloth tape, she measured the circumference and announced “5 and 1/8 inches diameter.”

Then to me: “Mr. Chester, now we need to check your ejaculatory function as well as your control. To do that, Karen will manipulate your penis while I observe. I want you to delay your orgasm as long as you comfortably can. Are we okay with that?”

I wondered who the hell she meant by ‘we’ but I mumbled assent anyway. Karen spread some medical lubricant on her gloved hands and took my rod in her right hand and balls in her left. She began by working me up and down at a slow and relaxed pace. The doc observed intently and turned to me “How are we doing, Mr. Chester?”

Again the ‘we’ question. If her crotch was getting wet, surely she’d know how she was doing and my throbbing dick was right out there for the world to see. Rather than the ‘okay’ most folks give the doctor, “Doc, I never knew it could be that good with latex. No, the eruption isn’t imminent.”

She made some notes and looking intently at my crotch: “Karen, you can step it up now.”

Eagerly, Karen stepped up the pace, at times letting go of my balls and going at it with lots of variety - alternating hands, both hands with fingers interlaced, hand over the end like a an artificial pussy, etc.. No doubt about it, this wasn’t her first medical hand job. Then her left hand went way down in my crotch and she stroked my balls and at the same time with her right hand, stepped up the pace on my dick. I couldn’t and didn’t hold back. Doc Henley stepped back to get out of the way. The first big spurt landed on Karen’s white scrub shirt. I thought she might let go and wipe it off, but dedicated to her work, she continued pumping and completely milked me out.

Doc Henley scraped some of my come into a pre-labeled glass tube and capped it. Karen proceeded to clean me up and wiped her shirt as best she could. The next surprise came when Doc Henley said “Mr. Chester we now have to measure your penis in the non-erect position. For that you’ll have to stand on the floor again.”

Some guys might have got mad and walked out at that, but what the hell, I’d just had a super hand job and maybe the doc would want to see how long it’d take me to recover and Karen would wank me off again. So I hopped of the table and stood there for measuring. With fresh latex gloves on, Karen took my soft dick in her right hand and laid it on the ruler. With the half ring against my pubic bone, she moved the stop to the end of my dick and read the result. “5 and 1/4 inches length soft.”

Dr. Henley, ever the stickler for professionalism, “5 and ¼ inches non-erect length!” Then she held the end of my dick while Karen measured the circumference with the cloth tape. “Okay, let’s see, yes 4 and 1/8 inches circumference, sof..., uh non-erect condition.”

Then Dr. Henley told me the exam was over and before saying goodbye, she told Karen to arrange an appointment in about 5 days to discuss the results, mainly the blood and urine tests. Then she walked out, leaving naked me and Karen alone in the examination room.

Karen, seeing that my dick was starting to get agitated again, said with a husky voice “Oh sorry, but we’ve got another patient coming in.”

I was thinking she might be wet right now and how nice it would be to not have to lube up – yeah just go right on in. Should I, a 60+ year old, ask a 20 year old medical assistant for her phone number? Would she laugh at me or would she coyly hand me a slip of paper with the number? Then Karen got called over the intercom. I got dressed and left after getting another appointment at the reception.

Lisa was waiting outside in her Ford. “So how was the examination?” And adding in a knowing sort of tone: “Did they find out how healthy you really are?”

When I answered by telling her that it seemed to be a really thorough exam and that the doc and the assistant made a really good impression, she coughed – probably to keep from giggling.

Back at her house, I got right to work and things went forward. That night and the next morning we pulled our little sneaky game of making it look like I was sleeping at the shelter, when in reality, I slept in the house with Lisa.

Wednesday afternoon, I had just finished all the priming, when I saw Jolene drive up in her white Mercedes coupe. After answering my ‘hello’ with a smile and a sexy wave, she rang the doorbell and I heard Lisa welcome her in. A little later, Lisa called me to come in and join the two of them for coffee.

After a few sips of coffee and a bite of cake, Lisa told me that they had found a place for me to live. It happened that in the strip mall where a friend of Jolene’s had an office, there was a bike shop with a studio apartment that a prior owner had illegally built in. Apparently, the current tenant couldn’t resist getting an extra $400 a month in tax-free cash for doing absolutely nothing. I moved in that evening.

Come Friday morning, I was nearly done with the second coat when it was time for my follow-up appointment with Dr. Henley. Again, Lisa drove me to the practice and waited outside. The consultation was over in five minutes and consisted mostly of Dr. Henley telling me I was in really excellent shape for a guy my age. Afterwards Karen gave me two envelopes, one with my name on it and one for Lisa, which made sense because she was paying the bill. In the car, I noticed the letter ‘K’ on my envelope and a 10-digit number, both lightly written with a pencil. As soon as I saw that the first three digits corresponded to a local area code, my question about whether to ask 20-year old Karen for her phone number was answered.

I finished painting that afternoon and after putting away the tools and leftover paint and cleaning up, Lisa called me in for coffee and pay. Over coffee she told me that she’d drive me home and that afterwards I should go see Jolene at her office – something about a job and I should shower and change to clean clothes to make a better impression.

Jolene’s company was named, of all things, ‘J & B Associates’ and from the outside appearance, the company could have been about anything – accountant, realtor, financial service, tax preparation service, even a law office for that matter. Inside, a secretary told me Jolene was waiting for me. Still wondering why she didn’t have me come to her house to look at what needed to be done, I went in and Jolene came right to the point.

“Art, I operate an escort agency and unlike most of the others around the city, I offer male as well as female escorts. Do you know anything about the escort business?”

Still thinking she wanted me to do some work around her house, I made an attempt at humor “I know I can’t afford to be a client of one.”

Laughing politely, Jolene said: “Art, you probably know that Lisa and I are friends and confidants. According to what she tells me, you wouldn’t need to use an escort service.”

“I didn’t know Lisa was a ‘kiss and tell’ type.”

“Art, please don’t be bitter about this. Lisa may have done what she did for me, but honestly, for her, it turned out to not be just strictly business. I asked you to come here because I want to make a proposal to you. If you accept, you’ll have a chance to get away from minimum wage jobs and sleeping in shelters.”

Thinking maybe she wanted me to become some sort of enforcer, maybe like a salaried pimp, I answered “Sorry, but I don’t own a pink Cadillac or a set of brass knuckles. Hell, I don’t even have a drivers license.”

Her reply just about made me fall out of the chair. “No, Art. I was thinking of engaging you as an escort.”

“Well I could die my hair, but the wrinkles in my face? No way am I going to get a facelift or get shot up with Botox!”

“Actually, you wouldn’t even have to die your hair. As I said, I run a special type of agency, offering both female and male escorts. My male escorts are mostly college students in there late teens and early twenties. That’s too young for some clients.”

“Jolene, I’m not gay and I couldn’t pretend to be either.”

“Art, hear me out please. I know you’re not gay. I’m talking about women clients. Especially more mature women – in their 40’s and up. Our escorts meet the clients in public, like in the lobby of a hotel, at a restaurant, at a museum, places like that. Together they go out for dinner, dancing, opera, theater, you name it. Our women clients want to go on a date with the escort, be romanced, they want to feel sought after. Can you imagine how self-conscious it makes a 60 year old woman to be on a date with a 20 year old man? We’ve even had women in their forties who weren’t comfortable being seen with a young guy.”

“So you’d pay me to go on a date with women clients. What’s the financial arrangement?”

“Art, it sounds like you’re interested.”


“Okay, I pay you $80 for taking the woman out to dinner, to a movie, theater, whatever. That’s for a maximum of 4 hours, like from 7 to 11. And all your expenses are paid, dinner, movie tickets, cab, whatever.”

“I thought escort agencies were for more than providing company.”

“They are Art. But I only get involved in the social side of things. Whatever you end up doing with the client and whatever she tips you is your business.”

“So how do I know what service to offer or what to charge?”

“Like I said, that would be your business and I wouldn’t want to get involved –officially. So how about if we go have a Friday afternoon drink together?”

We went to a TGIF Fridays a couple blocks away and there over gin tonics, she told me that basically, the minimum for an extra hour of fun was $300 and anywhere from $500 to $800 for an all-nighter. I damn near swallowed an ice cube from my gin tonic!

Then reality set in: “And you think women are going to pay me $300 – on top of your fee – for me to screw them?”

“No Art, not to screw them. They pay you to make love to them. According to Lisa, you do know the difference. Look, although we don’t get involved in that side of the business, we’ve had feedback that some of these young bucks don’t do much more than just pump it to the woman and can’t even get it up for a rerun.”

“Jesus, how much did she tell you?”

“Enough for me to know it was worthwhile to have her make the appointment with the Dr. Henley.”

My mind was spinning. “Jolene, the first time Lisa and I fucked was Saturday night. The physical was Monday morning!”

“You and Lisa didn’t fuck, you made love! In answer to your question, Lisa phoned me early Sunday morning when you were still snoring.”

It pissed me off a little to think how Lisa and Jolene had more or less taken over my life, but on the other hand if I could get the ‘tips’ she was talking about, hell I’d be able to go anywhere I wanted, how I wanted, and all the begging for minimum wage work would be over.

Sensing my aggravation she said “Admit it Art, don’t you find it erotic to hear that two women are talking about your sexual prowess and attributes. Speaking of attributes, I got the report from Doctor Henley. Good grief, 7 and ¾ inches! I’ve never had one that big in me!”

There was only one answer to that: “My place or yours?”

“Unfortunately, neither. You’ve got a date at seven-thirty this evening and we have to get you some suitable clothes.”

Fortunately traffic wasn’t too heavy on the Beltway so we got to Towson Center in less than 30 minutes. There at Nordstroms I got fitted out with a brand new navy blazer, blue and white striped shirt, tan slacks and dress shoes. Then we parked in front of the Best Western and Jolene gave me some instructions.

“Your date, Denise, will meet you in the lobby. She has light brown hair, no glasses and will be wearing a blue dress. Tell her you’re are ‘Ralph’ and give her this J & B Associates card. She needs to say that she’s ‘Denise’ so you know it’s her for sure. Make small talk and ask her out for dinner. There’s a bistro named ‘7-Extra’ in Towson Town. You’ll need to call a cab to get there and back. I have the feeling she’s never done this before so you may have to work hard romancing her. And remember, don’t charge less than $300 for an extra hour.”

With that, I got out and Jolene drove off leaving me to take on work I’d never dreamed of getting.

Inside the Best Western lobby, I saw a late 50’s woman in a blue dress, looking somewhat tense. I introduced myself and gave her the J & B card.

In a shaky voice and not really looking at me, she said “I’m Denise. So nice to meet you.”

I knew I had to put her at ease and quickly so I just sat down next to her and told her that the 7-Extra bistro in Towson had been recommended to me and made up a bunch of shit about how good my friends said it was.

“Well Ralph, I’m not from here so I’ll let you take the lead on that.”

“I’m going to have the concierge call a cab.” I didn’t want to give away that I didn’t have a car so I continued “That way there’s no worry about a second glass of wine.”

Already during the cab ride, she seemed to be calming down somewhat and by the time we were seated in the bistro, we must have looked like a normal couple. Of course she couldn’t resist asking about me so I told her that I had a small home improvement/maintenance business and due to a bad divorce, I had to supplement my income.

She told me she and her husband, a cardiologist with a big practice, lived in a small city in southern Pennsylvania. That of course reminded me that I wasn’t all that far from Chester, where I’d had to leave in a big hurry, but I put that aside and got busy with small talk. We had a nice meal with pleasant conversation and afterwards, sipping wine, we still hadn’t discussed any tip related service. I had to start some way so I asked her if she was in the Baltimore area for shopping or entertainment or just visiting.

“Actually both. As far as my husband knows, I’m here to shop for my granddaughter’s birthday. Ralph, I’m nearly 60, overweight and well, this is not so easy to say, but my husband has a big practice. Well you’ve probably heard stuff like this before – young nurses, hard work. I try to shut that out by doing lots of community work but sometimes, I think about other things, have fantasies. You understand?”

The word ‘fantasies’ was all the opening I needed and it didn’t take too long to find out what her fantasies were. To my great relief, her fantasies didn’t include any really weird shit - quite the opposite actually. Just talking to her about the fantasies gave me half a hard-on. Under the table, I put my hand on her thigh and she responded with a quiver of pleasure. We pretty quickly came to the agreement that she would pay me $600 to spend the night with her in her room. We skipped dessert and there was still some wine in the bottle when we left.

Back at the hotel, we took the lift up and in the hallway, Denise handed me the key card to her room. Inside the room, actually a suite, right away she took six hundred-dollar bills out of her purse and handed them to me. Then with a naughty smile “Now that’s out of the way, let’s get back to our date.”

I helped her off with her jacket and while I was hanging it and my blazer in the wardrobe, she went on into the suite. I found her standing in front of the dresser facing the big mirror over it. Taking a stance right behind her, I placed my hands on her hips and began by softly kissed her neck. At the same time that I expanded my kissing to her cheeks and ears - whatever I could reach - I moved my hands down over her hips to the bottom of her butt and the back of her thighs. Then back up the same way, my hands went on up to the flanks of her chest to graze the sides of her generous soft breasts. Then down again repeating the same thing several times before changing the routine to my hands moving forward over her hipbones and down to the front of her thighs. On the up movement, I then ran my hands under her breasts and hefted them slightly. All the while Denise was oscillating her head ever so slightly and softly swooning.

I had to let her know how I was doing so I held her hips and pressed my groin against her back so she could feel my hard-on. Taking her wiggling butt and continued swooning as encouragement, I reached up under her dress with both hands and stroked the front of her pelvis before moving to her vulva. Massaging her pubic area, I could feel the moisture through her panties. Leaving one hand to massage her pussy, I used the other to massage her tits. Both of us were still fully clothed but that had to change.

Whispering something like “I’ll be back”, I took my hands away from her pussy and tits and used them to unzip the back of her dress, unsnap her bra and pull down her panties. Now with free access, I massaged her tits and fingered her now very wet slit. When her hips got to oscillating so violently that I could barely keep my fingers in her pussy, I whispered in her ear “Denise, close you eyes and wait, I’ve got a surprise for you!”

I got two pillows from the bed and laid them on the dresser one atop the other. Then I undressed completely and again got myself tight against her back. She responded immediately: “Ralph, I can feel your hard penis against my back. I think it wants to be inside of me.” With that she bent over the dresser, elbows on the pillows and chin in her hands, and looked at herself in the mirror. In her bent over position, her pussy presented itself and I worked the head of my dick in between the lips and sort of worked it around to really get her ready. When she let out a pleasured moan and thrust her ass back, I knew that she wanted more. A light thrust of my hips and I had it halfway into her and began fucking her with slow short strokes. Bending over a little further, I took her tits in my hands and massaged them while I fucked her. In the mirror, I could see her pursing her lips and closing and opening her eyes, all the while swooning softly. Occasionally and especially when I made a deeper thrust, her swooning would be interrupted by a light squeal that I took to mean that I needed to be careful. At dinner, she had as much as said that her cardiologist husband hadn’t fucked her for quite some time.

I was getting close and I needed more so I pushed deeper and was surprised when she uttered something like “Ralph, yes Ralph, fuck me deep! Fuck me hard! I want your whole dick in me now!”

That was all I needed to really get in gear. At the same time, I wondered if I’d be able to hold back long enough so she could come too. Feeling the pussy juice on her thighs at the end of my in-strokes told me she was close but I still wanted Denise to climax first. She let me know that wasn’t necessary: “Ah, ah, ah, don’t hold back, come inside me now! I want to feel your hot come in my pussy!”

I let go of her tits, grabbed her hips and thrust even more madly. Then came the volcano. Denise reached back with both hands, held my hips and dug in her fingernails. The fresh flow of warm liquid that I felt go down my legs must have been our combined production.

After the eruption, her hands on my ass cheeks and her earlier fantasy confession told me I needed to leave my soft dick soak inside her and at the same time knead both of her tits with my hands. We stayed locked together like that for what could have been five minutes. I was beginning to feel like I might get hard inside her when she let go of my ass cheeks and stood up. My still soft dick slipped out and some more come dripped on the rug.

“Ralph, we should’ve put a towel on the floor first.”

“I had other priorities – like getting my dick in you as fast as possible.”

“You’re so romantic.”

“You’re the first to tell me that. We could just spill a drink on the rug as camouflage. Shall we go shower together?”

“Yeah and afterwards let’s use the tub spa in the bedroom. I’ll start running it full now.”

In the shower, we did an extra good job of soaping and washing each other. It turned out that both of us really got wound up when I got behind her, hard on against her back, and played with her soapy tits. Denise was overweight but sort of comfortably so. She definitely had a belly but it didn’t overhang. In a way it was sort of erotic, the way it stood out hiding a view of her pussy from close and above. Right away when we met in the hotel lobby, I noticed that her hips were fairly wide but that just seemed to make her more feminine. Her extra weight had two more advantages: It hid wrinkles in her face and it made her tits bigger. In fact her tits were too big for me to enclose in my big worker’s hands. In the shower I was really grooving on soaping them, rinsing them off, hefting them and then bending around to suck on her nipples. Just the thought of tit fucking those bazookas made my hard-on complete.

Still rock hard when we rinsed off, I would have fucked her standing up in the shower but she let me know that she had something else in mind. Still hard when we dried each other, I was surprised when Denise held a cold washcloth on my dick to slow me down. Then I remembered the tub in the bedroom and another of her fantasies.

In the tub we sat facing each other, her legs over mine. Considering that her husband hadn’t fucked her for years, it was no surprise that Denise had a fantasy about being pampered. Her arms spread on the sides of the tub, her head back and eyes closed, she let me take over. I lifted her mid-section to bring her crotch just out of the water and buried my face in her generous crop of light brown pubic hair, at first kissing superficially then becoming more specific by licking the slit. She, wanting me to use my fingers as well as my lips, moved her feet so as to support her mid-section in the dining position. I spread her lips with the fingers of one hand and raised her hood with the index finger of the other.

She had told me earlier that her husband had never come anywhere close to fulfilling Denise’s lifelong fantasy of having her inner and outer lips licked while her clit was being massaged. Determined to fulfill that fantasy and even more, I supplemented the licking by getting the tip of my tongue in her vagina. After looking up momentarily and seeing her fists clenching in ecstasy, her eyes still closed and her mouth opening and closing; hearing her scream and feeling the flow of juice hitting my tongue came as no surprise. Then she was quiet as her mid-section settled down into the tub. I had the impression that she had even lost consciousness.

After what seemed like a few minutes of her being out of it, she looked at me with a very contented and inviting smile. In fact her smile was so inviting I wouldn’t have needed to remember the rest of her fantasy to know what to do next. I got up on my knees and took her generous breasts in my hands, squeezing ever so lightly. Denise leaned forward and with her lips touching the head of my dick, she took it by the shaft with one hand and held my balls with the other. Knowing what was coming, I made up my mind to hold back so she could live out the rest of her fantasy. With the hand she had on the shaft, she pulled skin forward so it bunched up over part of the head. Then with lips pursed open, she moved her head forward so as to push my foreskin completely off the head. At the end of that motion, she would flick the head with her tongue. I was beside myself. She kept to that fucking like motion, pushing the foreskin back and then letting it slide forward as her head retreated, for what seemed like minutes. Adding variety to her blowjob, she used her left hand to hold my foreskin all the way back, like as if I were circumcised, and then she gave me a mouth fucking with as much stroke as the size of her mouth allowed. That did it. My first squirt went in her mouth. When she drew back, I thought I’d overestimated her capacity for kinkiness but she quickly interjected: “Ralph, in my face!” One jerk of her hand and a white blob was slithering down one side of her nose and over her lip to join the blob that was already on her tongue. Then she buried my dick between her tits and kneaded them so vigorously that I shot the next and last wad against her breast bone.

She let me get soft between her tits and then lay back against the end of the tub. After spreading and massaging my come on her neck and breasts, she gave me a coy smile and said “Ralph, I bet you’re holding back on me.”

I answered her by looking down at my now hanging member.

“Ralph, my doctor husband might not be fucking me anymore, but being married to a doctor, you do learn lots of physiology of the male reproductive system.” Then taking my soft dick in her right hand, she milked the rest of the come out onto her left hand and likewise spread it on her upper body.

Completely spent we both sunk into the tub and soaked and dozed. Waking to cooling water, we platonically washed and dried one another before going to bed naked and spooned together. Before dropping off to sleep, the question crossed my mind: Would I be able to service her again in the morning?

Hours later, I woke slowly to sun streaming in between the curtains and even more slowly realized I was no longer in the spooned position with Denise. Instead, I was on my back, the cover was down and she was sitting beside me, looking alternately at my face and at my groin. My still soft penis was in her right hand. “You don’t mind me fondling you do you Ralph?”

I answered with what I thought was look of assent and anticipation of pleasure and that is the way Denise took it.

“Ralph, you have a really big penis. Oh I’m sorry, but you don’t mind me saying that do you?”

“Denise, men like a woman to tell them they’ve got a big one – especially if they don’t.”

But you really do have a big one. It’s lots bigger than my husband’s. I could never get two hands on his shaft. Yours I can’t even cover with both my hands. When we were dating and the first few years we were married I used to give Mark head. His penis would go all the way in my mouth. With you, my lips don’t even get halfway down.”

I told her it was nice to be liked and I was glad she liked me. Then it occurred to me, Denise was begging for a compliment so I told her how much I liked her big tits and how good my dick felt inside her pussy.

Her fondling hand and the conversation were taking their toll. “Ralph, you’re getting hard right in my hand.” Then she bent down and gave the head of my dick a long smooching kiss. Rising up again “Ralph I’m glad you’re not circumcised. I like how I can make the head appear and disappear.”

I was about to ask her if her husband was circumcised but before I could, she volunteered the information without my asking. “My husband is circumcised. But honestly, that isn’t really the problem. But still, I really like playing with yours.”

As if the fondling and talk weren’t enough, Denise bent over, retracted my foreskin again and thoroughly licked the whole head of my dick before twisting her head and moving down and kissing and licking the shaft. That’s all it took. I was rock hard. Thinking she wanted to give me a blowjob, I continued lying on my back but that’s not what she had in mind.

Leaving one hand on my dick, she rose and snuggled her head up to mind and with a deep sexy voice asked “Ralph, could we screw – I mean the regular way? You know with you on top? Just use me! Really put it to me!”

So she wanted more aggression on my part and what she said and the way she said it put me in an aggressive male mood. I rolled her over on her back and before she had a chance to spread her legs, I spread them for her and got on my knees between them. My arms under her knees, I raised her legs so they were on my shoulders and entered her immediately and went in all the way. Her eyes were wide and her mouth open. Her tightness around my dick and her gasp told me she wasn’t completely ready so I backed off and fucked her slowly and going only partway in. This brought on a happy relaxed smile and we slowly got into the routine of a good friendly fuck – laughing, teasing, joking, talking dirty.

Sometimes I played with her tits, other times I held her hips and fucked with a maddening tempo. Obviously she wanted it to last because she kept breaking off the mad tempo by pulling my hands off her hips and on to her tits. Then even Denise couldn’t hold back and I felt the warm flow on her ass cheeks. For me the time had come as well and I shot a nice wad and collapsed on top of her.

Afterwards, we showered together and she milked me out. I only got half a hard on and Denise realized her night was over. I hoped she thought she’d gotten her $600 worth.

After drying off and getting dressed I got my answer. She gave me hundred dollar bill as a tip for what she called ‘extra attentive service’ and said she’d ask for me next time she went ‘shopping’ in Baltimore.

Elated with having made more money in one pleasurable night than I had made in almost two weeks of handyman work, I took a cab back to the strip mall where my apartment was and gave the driver a generous tip.

Inside, the efforts of the past night began to catch up on me so I went to bed and more passed out than went to sleep.

The doorbell brought me out of my deep sleep. Still in my shorts and tee shirt, I peeked around the door to see Jolene’s secretary, Maureen, standing outside. “Jolene wants to see you – say around 1:30. And wear your blue blazer and a nice shirt!” Looking at my watch, I saw it was already 1 PM. Remembering my new and easily acquired wealth, I couldn’t help but agree to be there.

At the office, Jolene told me she’d already heard from Denise and that there’d likely be another date the next time Denise came ‘shopping’ in Baltimore. There wasn’t another date lined up for me yet but I did get told to go to a nearby BestBuy and get a cell phone with a prepaid card and come back right away to give them the number. A half hour later, when I came back with my newly acquired cell phone and gave Maureen my number, there was another woman there. She turned out to be a local photographer who Jolene had hired to make a website photo of me. I didn’t agree to this until they showed me that the facial features of all their ‘models’ were blurred for the website. When you think about it, yeah, the clients have to have some idea what they’re getting.

After the photographer left, Jolene called me into her office and told me lots of stuff about how to behave and gave me lots of does and don’t-does. Finally, around 4 she indicated we were done. Disappointed because I’d thought she might have wanted to follow up on her interest in my 7 3/4 inches and hungry  because I hadn’t had breakfast or lunch, I headed over to my apartment.

When I got back to the building where my place was, there around the back of the store where the entry was, I heard a familiar voice: “Hey you really look sharp in the blue blazer.” It was Lisa in her car. “Had lunch yet?”

Over late lunch/early dinner, she didn’t take long getting around to asking about the happenings on my first ‘date’ for J & B. I’m not the kiss-and-tell type but she conducted an inquiry that would have done the 15th century Spanish inquisitors justice and before long, not only was I giving her all the nitty-gritties, I actually enjoyed doing it. About the time when Jolene had recruited me for the ‘date’ with Denise, it had crossed my mind that Lisa might be deeply pissed. Quite the contrary seemed to be the case – she seemed genuinely curious and the more I told her, the more her face sparkled.

Walking out of the restaurant she made the proposal I was expecting – namely ducking down in her Ford so she could get me in her house without the neighbors seeing. We had a couple gin-tonics in the living room and made out a little on the couch before she let on what the evening’s program would be.

Lisa went up to her bedroom first and told me to wait around 10 minutes before coming. When I came in, she was wearing a green dress and standing in front of her dresser, the top of which used to be covered with brushes, hand mirrors, photos and all sorts of decorations. Now on the dresser top, there were only a couple of pillows and a tube of KY. Turning her head slightly, she let me know that I wouldn’t have to put on a rubber. “After all, Dr. Henley said you were healthy.”

Except that I needed to lube up for Lisa, I pretty much replicated what I’d done with Denise. There was a difference though - Lisa was wilder and really enjoyed looking at herself in the mirror as she went over the top. The other thing different was that she insisted on me staying inside her after I came. “Your 5 ¼ inches soft is bigger than Ray’s –my husband’s name is Ray. You’re bigger soft than he is hard.”

No objection on my part, I’m a big fan of the post-fuck soak. Predictably, I got hard inside of her and we had another really good go at it. Afterwards, exhausted, we showered, went to bed and fell asleep pretty quickly.

Hours later, we were awakened by a noise downstairs and then we heard footsteps. The only weapon I could think of was a bedside lamp and I was trying to unplug it when from downstairs a man’s voice called: “Lisa, it’s me! Ricky’s lawyer got me out early!”

To Lisa I whispered “What the fuck?”

Whispering sharply: “It’s my husband Ray! Quick, grab your clothes and hide under the bed!” Lisa thought to put some of the stuff back on the dresser top and managed to get back in bed just as the bedroom door swung open.

That’s when I realized that being ‘separated’ from her husband had meant that he had been in the pen. I was also pretty glad that we’d been too pooped to fuck in bed because he would’ve noticed the wet spot on the sheets. The big question was how would Lisa handle him and how the hell was I going to get out of there?

What followed was to be a voyeur’s dream. The trouble was, I was too damn scared to really enjoy it – trapped in a room with a career criminal with mob connections and his wife whom I’d been shagging.

Lisa, excitedly and sternly: “Ray, you scared the hell out of me! I didn’t expect you out for months.” Then much softer and sweetly “It’s so great to see you again and have you back home. Oh Ray, I missed you so!”

Ray, sitting on the edge of the bed and pulling off his socks: “I missed you too Baby.”

From my cramped position under the bed I saw his pants drop. No sooner had he tossed his shirt away when his legs disappeared from my view and I heard him lie down on the bed next to Lisa. Then sounds of kissing, bodies squirming and two voices, male and female, proclaiming their everlasting love for one another. Then his shorts and tee shirt dropped over the edge of the bed. Was that really the woman I’d fucked twice less than a few hours before? Lisa was either a highly talented actress or she was a wanton sexual libertine – or maybe both.

Then the bodies shifted position and I heard Lisa’s moaning with pleasure. The lack of rhythmic thumping told me he must be giving her head. In spite of my precarious position, I had the presence of mind to wonder if he’d be licking up any of my semen. Her squeal told me he’d brought her all the way and then there was more shifting of bodies.

Ray, disgustedly: “Shit, I forgot to pick up some rubbers!”

Lisa, sweetly: “They’re in the little box in the headboard.”

Ray: “Still there after a year?”

Lisa, whispering sweetly: “Well I did take one out now and then just to remind myself of how it’d be if you were here kneeling between my legs.”

Ray: “And then?”

Lisa: “Oh, I’d roll it onto a deo bottle.”

Ray: “You mean you used a deo bottle as a dildo?”

Lisa: “No silly man. That was just a lead up to – well you know.”

Ray: “Did you think of me when you rubbed your pussy?”

Lisa: “You know I did Honey. Oh Ray I’ve so much missed having you here. Missed having you put your big dick in me. Come closer so I can put the rubber on you.”

Then after hearing bodies shifting position, tearing of foil wrapping and giggling, Lisa: “Ray, the KY, it’s in the box too.”

Ray, teasingly protesting: “But you were pretty wet already and I slobbered in your pussy too.”

Lisa: “Your tongue didn’t go in my vagina like your penis will. You know what you need to do, put a little KY where my vagina is and then put some on the rubber too.”

There was more moving of bodies, giggling and then I could hear his weight settle on her and from her outward gasp, I knew he had entered her.

I wondered if I should try escaping while he was in the throes of passion or wait till he fell asleep. Still naked because there wasn’t enough room to dress under the bed, I’d have to be sure and take all my clothes when I slid out. I decided to wait till Ray slept, of course taking the chance that I might have to piss long before then.

Gradually, the flesh smacking and slapping and the bed thumping got more and more intense. Moans of pleasure, gasping, deep inhalations, yelps, squeals, you name it, all got louder and louder. I started wondering if Ray worked for Jolene too.

All that action, not two feet above my face, and with the woman I’d fucked no more than a few hours earlier. I started getting hard before the thought of my dilemma brought me back to my senses. Then some loud male grunts and a familiar female squeal told me they’d both gone over the summit. I wondered how deep their juices would soak into the mattress. Then it was quiet as they cuddled for several minutes.

Lisa, sharply: “Ray, the rubber!” The bed squeaked as he rose. “Oh, there’s really a big gob in there.” I imagined her holding it up and the two of them admiring his deposit. “Let’s go shower, we’re both all sticky.”

As they got out of bed, I saw Lisa drop a hand down for me to see. Her upturned thumb jerking in the direction of the door to the hallway told me that I was to get out as soon as the getting was good. Upon hearing them talking and giggling in the shower, I slid out from under the bed and tiptoed downstairs carrying my clothes. Dressed again, I let myself out the front door. While walking back to my studio apartment, I couldn’t help thinking about Lisa’s acting talent. Or was she just so much more sexually liberated than the rest of the world - including myself?

I woke up late Sunday morning wondering about my next date: Who? Where? When? After breakfast it finally sunk in that the escort work might mean that my handyman days were really over – for good. Hell, I might even be able to live in a real apartment, not just an illegal studio in a strip mall shop.

Reflecting back on the events since that first morning at the Baker Street shelter, I started trying to put facts together. Clearly Lisa and Jolene were in cahoots and it had been Lisa’s job to check out whether I could get it up and put out a respectable fuck. Was Lisa’s husband Ray involved and did he know that Lisa conducted talent auditions? Were John and Martha involved?

Was Doc Henley also involved? A physical like she gave me couldn’t be standard medical practice. Then it occurred to me that I hadn’t even opened the envelope that Karen had given me. I knew it would show that they hadn’t found any STD, but would it show the size of my dick and the strength of my ejaculation? I ripped open the envelope. Sure enough the dick and ejaculation data were all there. But why did they need to do that for Jolene? It could only be that Jolene wanted to confirm Lisa’s evaluation. Sure they were friends but there’s the old saying ‘Trust is good, control is better.’

Glancing at the envelope, the ‘K’ followed by the 10 digit number again caught my eye. With Lisa’s husband back and taking my place, I started thinking about giving ‘K’ for Karen a ring. After a late breakfast and a Sunday afternoon nap, I got the nerve up to call. Karen sounded surprised to hear from me and was a little standoffish at first but she quickly warmed up and we arranged to meet the following Sunday for brunch – at her apartment.