I started renting a small executive office space for my business in the downtown area.  I eventually met my office neighbor Jan, who was an older lady, a tad odd, but very nice.  She was a very interesting person after I got to know her, especially when I heard her talking to herself through the shared wall of our two offices.

After a year or so of talking to her and getting to know her methodology of investing, I decided to let her invest some of my money in one of my 401k accounts.  Jan and I kind of became friends, and would occasionally go out and have a beer after work.  She was older than me, I'd say she was pushing sixty.  One day, we had made plans to go out for a couple of drinks the following night.

The next day at the office, I saw Jan when she came in.  She was really looking nice, and I noticed that she looked like she had lost some weight.  She had on a very nice kne- length skirt, a very nice blouse with a jacket, and heels which were not as conservative as she normally wore.  She never wore anything less than conservative.  She looked liked she had just gotten her hair done, and even had lipstick on, which she hardly ever wore.

The day lapsed on, and after a long irritating phone call of hers ended, she came over and stood in the doorway of my office and said, "Well, I hope you're ready for a beer, I know I am."

I told her that I'd be ready in a few minutes after I shut down.  When I was ready to go, I walked over to her office and asked where she wanted to go.

She said, "We can just walk next door if you want?  That way I can leave all my stuff here, then walk back and get it before I head home."

As she was telling me this, she was rubbing her neck, like it was stiff.

I said, "Are you sure that you still want to go? You look like you're in a little discomfort."

She said, "Oh no, I need a drink. This one client is making me crazy."

Walking into her office towards her, I said, "Is your neck stiff? I can work it out for you.  I'm pretty good at it."

She said, "That sounds good about right now."

So, I walked over behind her and gave her a nice neck massage for about five minutes.  She seemed to enjoy it, and at times, she tilted her head back with her eyes closed and opened her mouth a little.  I was looking down at her, and for some reason started fantasizing about her giving me a blow job.

When I finished, she said, "Wow, that was really good!"

I said, "Well, I always thought about becoming an LMT.  If I was younger, I would probably get my license."

So we eventually locked up and headed to the pub next door.  We ordered a couple of beers and an appetizer and started chatting about the markets and other small talk.  After we pounded those beers, we ordered another round, and Jan excused herself and went to the restroom.  When she came back, I noticed she freshened up with her lipstick.

We talked for a while longer while we finished our drinks.  I just kept looking at her lips and wondered what they would feel like wrapped around my cock.  I thought to myself, 'I bet she gives a great blowjob.'

The waitress brought our bill and I picked up the check.  Jan said, "you should have let me get the bill, especially after that wonderful neck massage."

As we got up to leave, she seemed a little tipsy and fumbled around getting her purse.  It was getting dark out as we walked out the door and she said, "You better hold on to me, I feel like I'm going fall."

I grabbed her hand and we headed back to the office.

When we got in, I said, "Are you OK to drive?"

She said, "Yea, I'll leave in a bit."

I said,  "How's your neck?"

She replied, "Better, I'll ice it when I get home."

I said, "Would you like me to work on it again?"

She said, "Sure if you have a little time for an old woman."

I said, "C'mon now, you're not an old woman, you look great!"

With that, I went over to her like before, and started working on her neck.  She seemed to enjoy it and I was working her deep, occasionally reaching my thumbs under her blouse and getting a glimpse of her lacey bra.  She had to know I was getting some views.

When I was done, she said as she stood up and faced me, "You know, you're a very handsome man."

I didn't really know what to say to that other than, "Thank you, that's a nice thing to say."

Then she said, "This is going to sound a bit strange, but I've always wanted to kiss you.  Can I kiss you?"

Then before I could say anything else, she reached in towards me, and gave me a kiss.  We stood there for a bit and started making out.  It felt a little awkward making out with my financial planner, but man, was I enjoying it.  Our kissing intensified and we started sucking on each other's tongues.

Then she put her hands on my ass cheeks and said, "How would you like a little payback for the neck massages?"

I said, "What do you have in mind?"

She said as she grabbed my crotch, "Would you like me to suck your cock?"

I said, "Of course I would. As long as you're sure it's OK since I'm your client?"

She said, "It'll be fine, I won't tell anyone if you don't.  And besides, you're supposed to do what your Financial Planner tells you to!"

Then I replied, "What does my financial planner want me to do now?"

She said pointing to the corner, "Go over and stand in front of that chair."

I went over to a really nice leather upholstered chair in the corner of the room.  She turned on a little desk lamp, then went over by the door and shut the lights off to the room.

She came over to me and then said, "Now that's better."

We started kissing again, and she started unbuttoning my pants and undid my zipper.  Then she got on her knees and took my socks and shoes off so she could remove my pants.  After that, she started nibbling on my hardening cock through my underwear while looking at me in the eyes.  She was really good at this anticipation tactic, and I couldn't wait for her to slide my underwear off and start sucking me.

When she was done teasing me, she finally slid my underwear off and told me to sit in the chair and make myself comfortable.

Then she said, "Close your eyes and relax."

So I did, and she grabbed my cock and started licking the base of it, then she starting sucking my balls.  Then she started kissing and licking my shaft making her way to the head.  I just had to open my eyes and watch.  She gently started kissing the underside of the head of my cock and then all around it.  Finally, she took just the head into her mouth to tease me while gently sucking on it and rapidly swiping her tongue across the opening.

Her eye contact was unreal as she was working her tongue across the head of my cock.  Her lips gently encapsulated my dick head while she worked her magic tongue.  I noticed her lipstick was worn away, and I had this crazy urge for her to freshen up her lipstick.

So I said to her, "This is going to sound weird, but would you do something for me?"

She said, "Mm, hmmm."

I said, "Would you mind putting on some lipstick for me?"

She said, "Oh, you want me to redo my lipstick before I suck your cock?"

I said, "If you don't mind."

She went over to her purse and got her lipstick, then came back over and knelt back down in front of me.  While looking at me in the eyes, she pushed her lips out a little to apply a new coating of lipstick.  It looked so hot.  Then she handed the lipstick to me and pushed her freshly coated lips to my cock head.  

Then she said, "Do you like? If you want, you can put more on."

Then she put her mouth back on me and I started to apply lipstick to her lips and getting some on the head of my dick.  This was one of the hottest things I ever saw while getting a blowjob.  Now, I was ready for her to take my cock into her mouth.

After she was done teasing my dick head with her flickering tongue, she started to devour my cock little by little.  After aggressively sucking me totally down her throat, she released me and said, "Tell me what you like."

After a little breather, she went back to work on me, and as she was driving me wild, I was trying to think what I wanted her to do.

So I said, "I want you to remove your blouse."

She did so without missing a beat.  She had a really nice lace bra and large breasts.  I knew I was going to blow my load soon, and I didn't want to get it all over her silky blouse in case she didn't want me to cum in her mouth.

Then I said, "I want you to go all the way down on me and then lick the underside of my cock with your tongue."

She did exactly as I said.  She took my cock all the way into her mouth and throat and started licking the bottom of it.  I just held her head close against me while she did this.  I knew I was going to blow my load as soon as she started sucking me again.

So after a few minutes, I said to her, "I'm going to cum soon, where do you want me to cum?"

She stopped and said, "Wherever you want."

So, I pushed her back onto my cock, and while gently grabbing her head, I started her in a bobbing motion.  I knew I wouldn't last long.  Then just as I was ready to cum, I pulled her off my cock and held it against her nose and cheek and blew my load all over the left side of her face.  After I was done pumping, she took me back in her mouth to catch any final drippings.

After she let me out of her mouth, she took her finger and started to wipe the cum from her face and then brought it to her mouth and took down every drop.

Then she said to me, "Aren't you going to help me clean up your mess?"

I said, "Sure, where can I get a towel?"

She said, "There are no towels, use your tongue."

I thought that was an awkward request, but I was supposed to do what my Financial Planner told me.  So I licked the cum off her face and fed it to her.  I have never done anything like that before.  She sure seemed to be a hell of a lot kinkier than I ever imagined.

When she was all cleaned up, we made out for a while.  It was pretty hot being able to taste my cum while we sucked on each other's tongues.

We gathered up our things to leave and she said, "I guess we'll have to get together again soon and actually go over your portfolio.  I have to get home now because Tim is coming over later."

I thought that it was really weird that she had a boyfriend and just gave me a blowjob.  She never mentioned anything in our discussions about dating anyone.

It was getting dark out, so I walked her to her car.

She opened her car door and turned to me and said, "I hope you enjoyed your blowjob, I know I did."

I said. "I did, it was really great, it just caught me a little off guard."

She said, "I know.  Next time, we need to schedule an extra hour or two to go over your portfolio.  I do reviews at home on occasion!"