Starting Over

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...? I thought you were separated."

"It's complicated. He had some girlfriends and then, well mainly it's because he got put 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 how the pleasant morning probably meant that another a fine day was in store.

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 a sharp retort. "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 cum. 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 back 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 a 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 being a professional nurse dedicated to her work, she continued pumping and completely milked me out.

Doc Henley scraped some of my semen 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 1/4 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 to the neighbors 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 over the offices in the back. 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? And no way am I gonna get a facelift or get shot up with Botox!"

"Actually, you wouldn't even have to die your hair. As I've said already, 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. You might think that's ideal, but 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? And that's to say nothing about the difficulty in communicating. You might find this hard to believe, but we've even had women in their forties who weren't comfortable being seen on a date with a college age 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."

"Yes."

"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 openly 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."

I felt my face reddening with the thought that the woman sitting across from me had gotten a blow-by-blow account of my bedtime exercises with Lisa. "Jesus, how much did Lisa 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 last 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. The tone of her voice alone would have been enough to tell me that you really treated her well. But she did give up enough details for me to see that you'd be ideal for this business."