Jan was out of the office for the rest of the week, which was kind of nice, because I thought it might be a little awkward between us after last week's activities.

Monday morning she was in bright and early, and came and stood in my doorway and said, "Good morning!" with her coffee in hand.

Man, she looked great.  I swear, every week she looked like she lost another five pounds.  She asked me how my weekend was, I did the same, and we just continued on with some small talk.  She had her lips covered in a fresh application of my favorite lipstick, and all I could think about was getting them wrapped around my cock again.

Out of nowhere, she said, "I really enjoyed Thursday night.  Maybe we can do it again sometime soon?"

That was music to my ears.  But I was curious about this Tim guy, so I asked her, "Who's Tim? Are you in a relationship?"

"Not really, we're just good friends.  We do hiking and some other activities, but other than that, there's not much romance.  In fact, we're kind of breaking it off, other than a hike or lunch here or there.  We were actually supposed to do a weekend hike next weekend, but I decided against it.  Any chance you might want to go?"

I said, "Where were you planning on going?  I'm not much of a hiker or an outdoors person, so I wouldn't want to ruin your weekend."

"The Grand Canyon.  There are some beginner trails and we could stop whenever you wanted to, and I'm positive you won't ruin my weekend.  Think about it, the weather will be perfect, and I have all the equipment.  And if you're worried about facilities, there are a couple of camping areas that are near showers and restrooms."

I had never really gone camping before, ever!  I kept thinking about it, and thinking how erotic it could be, to actually be having sex out in the middle of nowhere.

I hadn't seen much of Jan after that because she was pretty busy with clients.  Finally, Wednesday she stopped in my office and asked if I had given any thought to the hiking proposal.  I told her I had given it some thought, but wasn't sure if I was going to go.

She shut the door to my office, and walked over to me and asked, "Is there anything I can do to persuade you to go?"

I said, "I've just never gone hiking or camping before, and I don't want to ruin your trip.  I know you're very experienced at hiking, and I know it's harder than it looks."

She said, "I'll make you a deal.  If you go with me this weekend, I'll give you a blowjob right now, and I don't have a client coming in for forty-five minutes."

"That's a deal I don't think I can refuse!"

So, she walked over and locked my office door, then came back over to me.  I stood up, and we starting making out and she immediately started to unbutton my pants, undid my zipper and pulled my trousers off.

I took off my underwear and sat back in my office chair.  She then got on her knees and immediately started sucking me deep and I became hard in a hurry.  She was taking me all the way in right out of the shoot, and no oral foreplay today, just right down to business.

I was going to come in just minutes into her heavenly throat.  I knew she had an appointment, so I couldn't get her messy.  I told her I was going to come, and she just throttled all the way down on me and waited while I held her firmly on me.

Finally, I blew my load and pumped my seed down her throat.  She didn't even flinch.  After I was done, she just started sucking again, just like before.  Clearly she wanted more, and wanted it now.  I was in heaven with my cock totally in her mouth and throat.  I really thought that Jan gave the best blowjobs I've ever had.  Then I thought, 'if she can do this in my office, what would it be like out camping?'

Jan made me come massively one more time before setting me free.  Fortunately, I had some napkins in my drawer if she needed them, but there's was no mess to clean up.

She got up and I put my pants back on.  We made out for a little bit and I could taste my come in her mouth.

"Well, I guess I better get ready for my appointment.  Maybe after work, we can grab a bite and discuss the trip."

"That sounds good, I'll be ready around 6:00."

Six o'clock came, and Jan came into my office and stood in the doorway again, with that shit-eatin' grin on and said, "Well, it's 6:00!"

She looked so sexy.  I noticed lately, that she was wearing sexier stockings and heels.  A much-needed switch from her other school teacher look.

Sometimes women need to hear compliments, especially when they're in a transformation, so I said to her, "Jan, I just want you to know that you really are looking really nice lately, and if you don't mind the compliment, I'll use the adjective, hot!  You've really changed.  I hope you don't mind me saying this to you.

"No, that's fine.  I've been working really hard at it, and I'm glad someone noticed."

"Well, shall we go, I want to see if I can get you drunk."

"Sounds fun, let's go."

We just went next door like the last time, because it was convenient to walk there.  We had drinks, and something to eat, and Jan was sucking them down.  I only had a couple, because I thought I might have to drive her home.  Maybe that was her plan.

We were there for about an hour and a half and discussed her new diet, workout regiment, and some things about the trip, but she was getting hammered.

She said, "Well we should go, but I can't drive, so you're going to have to take me home.  I hope you don't mind?"

"No, I only had two, so I can take you."

We stopped back at the office and got our things, then headed to her house.

After we got inside, I noticed she seemed to be sobering up a bit.

"Well, looks like you're all set, so if you're good, I'll head home.  If you need a ride in the morning just text me."

"I was hoping you could stay, maybe just for a little while?"

I thought to myself, 'could I stand another blowjob today with that awesome mouth?'

"Sure I'd love to stay awhile."

"Would you like a glass of wine?  I have a Chardonnay and a Merlot."

"I'll take the Merlot please."

She came out to the living room with our wine, and we sat close together on the couch.  There wasn't a whole lot of conversation, just a little sighing and sipping on the wine.  Then she lifted her leg and crossed it over onto my thigh.  We then looked at each other and started making out for a bit.

"Can I be candid with you Tony?"

"Sure, what's up?"

"I really enjoy your friendship, and I love helping you financially as a client.  But, I really like you, and you really turn me on."

"Well, thank you!  You do too, and I really like doing things together with you."

"That's just it.  I need someone right now to handle me.  It's been such a long time since I've felt like a sexy woman, and I want you to take me upstairs and do things to me that you might not do with someone who you know, or have feelings for."

"You mean, you want to have what guys call, 'stranger' sex?"

"Yes, I believe that's what I want."

"Well, I can do whatever you're comfortable with."

"See, that's just it.  I don't want to comfortable with it.  I want to be uncomfortable with it.  I just want you to be comfortable with it.  I want you to take me to new places."

Wow, I surely wasn't expecting to hear that tonight, but it sure got my imagination going.  I guess she was putting me in charge.

We finished our wine, and I said, "let's go up to your room."

"I thought you'd never ask.  Give me ten minutes to freshen up, then you can come up."

"Okay, just don't change your clothes."

Ten minutes passed, and I headed up to her bedroom.  She was just standing by the dresser, looking into the mirror and applying fresh lipstick and teasing her hair a little.  There was a lamp dimmed low, sending just enough light for us to see each other.

I walked towards her, and she turned around.  We grabbed each other and started kissing.  Then our tongues got involved, and we proceeded to enjoy each other's mouths every way possible.

She could sense that I was starting to get hard because of our closeness.

Our kiss broke and I started to unbutton her blouse to remove it.  She looked so hot in her business attire.  I did notice that she did change her hosiery, but I didn't say anything.

After I removed her blouse, I sat her on the bed, then positioned her across the bed on her back with her head leaning down a little just passed the edge of the mattress.

My crotch was right at her mouth level, and I started to remove my shirt, trousers and underwear.

Then I knelt down and started kissing her while I started jacking my cock to get it hard.  I then stood up, and took my hand and stuck one finger, then two then three in her mouth trying to see how wide she could open.  I grabbed my balls and pushed them to her mouth and she eventually got them in her mouth and started to suck and lick everything that was now inside her mouth.  I held my cock out of the road so she could just concentrate on them for a bit.

I believe she enjoyed the experience of taking care of my balls and sack and now it was time for her gorgeous mouth to welcome my rock hard unit.  I pulled her head down a little more passed the edge of the mattress so that now my cock was nicely lined up with her mouth and throat.

I told her, "open your mouth for me." And she did as instructed.

I shoved my cock into her mouth and started to fuck it easy at first, then she let me push myself in as far as I was able, taking me all in.  Then I put my hands gently around her neck as I started thrusting in harder and faster.  She wasn't resisting me at all.  While I continued fucking her throat, I removed her bra and started massaging and squeezing her breasts while she sucked me to Nirvana.

I knew she was waiting for my load.  I couldn't believe she had my cock in her mouth just hours ago.

I expelled my third load of the day down deep down her throat, and much more aggressively than earlier.  She just seemed to love it all.

She was really making me hot for her as she took my balls back in her mouth.  I really wanted to fuck her now.  So as she was cleaning my balls, I pulled her skirt off.  I noticed then she had some sexy laced top thigh high stockings on (that I know she changed into when she first went upstairs) and panties that matched her bra.  I bent over her and slid her panties off while holding her legs straight up from the bed.  

Then, I pushed her legs apart as I reached around them with each arm and started to devour her pussy.  I started sucking, licking and probing her pussy like it was the last one I would ever see.  She was moaning and going crazy.

I couldn't wait to fuck her any longer.  I got on the bed and turned her so her head was on the pillows.  Then I got on top of her, grabbed my cockhead and rubbed it around her pussy getting everything nice and wet.  I mounted her and I couldn't believe how tight she was.  I grabbed her legs by the ankles and pressed them back towards her so I could go in as deep as possible.  I started pounding her as hard and as fast as I could.

She started telling me, "Fuck, me? Fuck me harder, fuck me as hard as you can.  I want you to come in me."

I did as she asked.  I don't think I could have fucked her any harder if I tried.  Then I came once again.  Jan was wearing me out.  I never in my life would have guessed what a fuck machine she was.

We then rested for a bit. Jan seemed to have enjoyed everything we had done.  Then out of nowhere, she asked, "Do you have any fantasies?  Is there anything you want?  I'll do it for you.  Just tell me."

"Anything?  Be careful what you wish for!"

"Yes, I'm sure."

"I really want to fuck your ass."

"Wow, really?  I've never done that, but I've always wanted to try."

"You've never had anal intercourse."

"No.  I've done it with toys, but never with a man."

She must be the only woman I know to never have had it up the ass.  And, since she said she did it with toys, she must have some kind of lube.

So I asked, "Do you have any kind of lubrication?"

"Yes, let me get it."

She went over to her nightstand, got the lube and handed it to me as she got back into the bed.

"How do you want me?"

"On your knees and place your head into the pillows to be comfortable."

She did as I asked.  I got behind her, and started to rub her ass cheeks, then gently kissed her in various areas working my way to the prized hole.  She loved it, as she started moaning softly as I started licking and probing her tight little ass hole.  After a bit of getting her nice, wet and relaxed with my tongue, I got the lube and applied it gently to her anus.  She was enjoying everything so far.

I then started to finger her with one then two fingers.  As I continued fingering her, I moved to the side and put my cock to her mouth.

"Suck me and make me hard for your ass!"

After a few minutes of her glorious mouth sucking me, I was hard as a rock and moved behind her, and applied some more lube to her ass and my cock.

I moved in close holding my cock just a bit behind the head and gently pressed it against her ass.  It literally slipped right in.  I started pushing in gently, and with ease her ass swallowed all my cock in just a few minutes.  Once I got all the way in, I just remained stationary, and felt her tighten then loosen her ass muscles around me.  Her ass felt like a heating blanket wrapped around my cock.

Once she seemed comfortable, I started gently pumping her, then we worked into a more vigorous rhythm.  I could not believe how easy her ass was to fuck and how hard she was actually pushing onto me.

"Oh, your cock feels so good in my ass. Fuck it, baby, fuck my ass!"

I knew I was on the verge of a major cum dump, so I pulled out and rolled Jan onto her left side.  Then I grabbed her right leg, crossed it up and over, and straddled her left leg.

I crammed my cock back up into her awaiting asshole and started pumping away as hard as she would let me.  Then, we started kissing, awaiting my load.

"I'm going to come in your ass!"

"Come in my ass.  Give me all your come, baby."

I pushed into her ass as far as I could and exploded.

I never took Jan to be such a power fuck.  She seemed to be such a conservative lady when I met her.  I guess you really cannot judge a book by its cover.

Jan and I went on the camping trip and continued to have great sex, in and out of the office for months until I eventually ended up moving out of state.

She stills handles my financial planning.  It gives me a good reason to visit.