Wednesday well before the crack of dawn, brought me the answer to the previous night's question. I woke to Martha's hands on my shoulder and her tongue in my mouth. When she broke the kiss, she said, "John, you hesitated before you told Mary No last night. Have you ever had a cock up you ass?"
"Huh? No, nothing more than fingers."
"Well, all Mary could talk about last night after you left was how she was going to fuck your ass. Sooner or later, she's going to get you to let her do it, too. I'd really like to be your first, and not just to beat Mary to it. How about it, will you let me peg you?"
That was one hell of a wake-up call. All I could think to say was, "Now?"
"Yes, now. We have a little over an hour before we have to get ready to leave. That'll give us plenty of time to do it right."
"Um, for you, okay. But I'll need to pee first. And I hope you have something smaller than Mary used on you last night, because I've never done this before."
"You'll need to do more than pee. I want you to clean yourself out. There's an enema kit in the top of the towel closet. I can help with that if you want."
"No, I think I can manage that." Weird. I'd eaten my cum out of this woman's mouth and cunt, and I was about to let her shove a rubber cock up my ass, but I was too shy to let her see me shit. It's funny how our minds are wired.
"Alright. As for something smaller, have a look." She opened her robe and there it was, a pink dildo attached to a harness, sticking out from her belly. "Here's the one from last night," she said, hauling a black dong out of a pocket in her robe. The one she had on was smaller, maybe an inch or two shorter and noticeably not as tick. "And don't worry, I promise I'll be gentle," she said with a leer. "Now, get your ass into that bathroom and get yourself cleaned out so we can have some fun."
When I'd finished in the bathroom I came out to another big hug and kiss from Martha. It was really strange to feel her cock pushing up against mine. But kind of exciting, too.
"Now, I want you to lie on your back in the center of the bed and spread your legs, then grab your legs behind your knees and pull them up a little. It might be a little easier to fuck you doggy fashion, but I know you like to watch my face when I come, and I want to watch yours when I put my dick in your ass."
I did as I was told, then Martha got one of their little lube plugs out of the bedside table and started pushing it into my ass. It felt pretty good as it molded itself to me, then melted. After that she climbed onto the bed and positioned herself between my legs. She moved her hips forward until I could feel her cock pressing against my asshole. "Gentle or hard," she asked.
"For Christ's sake, gentle," I said, and she began to push. Suddenly that cock felt a lot bigger than it had looked. Dammit, it hurt! Martha could see that from the grimace on my face, so she stopped pushing and said, "You'll like this a lot better once I get it all the way in you. Now try to relax your sphincter. I'm not going to put any more into you until you do."
Eventually I felt myself getting used to the pressure in my ass, and that must have showed on my face too, as Martha began to push again, gently. Suddenly, I could feel the knob of her cock press past my sphincter. "There we go, Hon, I'm in." She dropped down on to my chest and gave me a big kiss, then told me I could let go or my legs and try to wrap them around her, like she did when I was fucking her from the front.
After that Martha began raising and lowering her ass to pump in and out of me. The sensation of her cock sliding in and out of my stretched asshole was actually beginning to feel pretty good. "That's good, Hon. You look like you're beginning to enjoy this." Then she brought one hand down between us, grabbed my cock and started to jerk me. Between the sensations in my ass and her expert handjob I had no trouble coming, big. She scooped some of my cum off of my stomach and licked her fingers clean, then leaned in and kissed me, coating my tongue as well. Slowly she pulled back onto her knees, which produced a short of pop when her cock came out, and lifted my knees up and apart again. "I wish you could see this, Hon, you are really gaped. Next time I'll need to remember to bring a mirror so you can see. Now, I think we really do need to get cleaned up so we can go to work."
Once she got rid of her rig, and we were into the shower, she insisted that I return the favor by eating her out until she came.
Then the less exciting part of getting into the day began. We had breakfast coffee with paczki before Martha drove me over to the garage. On the way she asked me to call as soon as I knew which way the wind was blowing with Jack Doe. She passed me a card with her private number on it, not the answering service, and told me not to let anyone else see it. All very businesslike, or schoolmarmish. No goodbye kiss, but I was getting used to not expecting one outside the apartment.
Except for a few short breaks to clench my ass muscles and think back to my wake-up pegging, and the half hour I stole to put together the outlines of a business plan, my morning's work was involved enough to keep my mind occupied and my nerves down. At least I made it to lunch time without costing anyone any money. But when lunch time came, no longer distracted by work, my nerves started to act up. I really felt like skipping lunch, but my head said I shouldn't go to the Jack Doe meeting on a completely empty stomach. I figured I'd have plenty of time to digest before then, so I grabbed something at a restaurant near the bank. To this day I can't remember what it was.
After that I went back to apartment hunting. I got lucky, and took the first one I saw that afternoon. It was no-frills, but clean and within a reasonable walking distance from Mary and Martha's condo, though far enough off the water to be out of their high-rent district. It even had a garage space where I could park my car for an extra 10% a month, and was close enough to the L that I could leave the car and save the downtown garage fees when I felt like it.
It was unfurnished except for appliances, so I spent the rest of the afternoon buying furniture, linens and kitchen stuff, all to be delivered Saturday. That suited me just fine since I didn't want to leave the bedroom next to Martha's before I had to. Next I bought some toiletries and headed back to my new apartment where I cleaned myself up a bit. Then it was time to get back down to the loop and face the music with Jack Doe.
Jack Doe's office was, as befitted a man of his wealth and power, on the top floor of his very own skyscraper, with a magnificent view of Lake Michigan through its glass north wall. You got to it off the private elevator that led to a lobby the size of a tennis court with a board room off one side, and who knew what behind a closed door on the other side. (I found out later that it was his main frame computer, surveillance and communications systems room.) Behind the receptionist's desk was a door that led to Doe's private secretary's office which in its turn had the door to the inner sanctum.