My First Experience with an Older Woman

I worked for a financial services firm, traveling around five-states, visiting companies that were our agents.  Much of the job was entertaining.  I was 28 and between girlfriends.

A great big Savings & Loan bought my company and also took over many Savings & Loans that were in my territory.

They wanted me to connect our agents with our new owners.  Top management came in from out of town.  I found a good restaurant to meet and discuss plans.

I went early to the restaurant before the dinner meeting, making sure everything was in order.  Going in, I noticed an attractive older woman sitting at the bar having a drink and smoking a cigarette.

My eyes “took in” her body.  She was wearing a tight grey knit dress.  She had attractive legs, and hips, with just a bit extra around her belly.  She had nice breasts.  Her hair was dark with grey streaks.  I thought, “For an older babe, she is hot.”

Sitting at the table, my eyes were still glued on the older woman at the bar.  A waiter approached her and led her to our table.  She was one of the “big shots” I was meeting for dinner.  Her name was Jill and we lived in the same Metro-Area.  She was drinking Scotch and ordered another one.

She told me we would be working together visiting clients.  The other people came for dinner, and we had our meeting.  After everyone else left, Jill and I ordered another drink and we continued to talk, both business and personal.  I was imagining what she looked like naked and was getting hard.

It was getting late.  Being the gentleman, I walked Jill to her car.  Walking to her car, she stumbled, and we grabbed each other.  We walked to her car with me holding her.

At her car, we stood for a moment with me still holding her.  I kissed her on her lips.  There was no reaction from Jill.  Then she asked, “Why did you do that?”  I thought to myself, I did a dumb thing.  Jill was high enough in the organization that she could fire my boss’s boss.

I apologize and told Jill it seemed like the natural thing to do.  Jill kissed me back passionately.  She said she was drunk and had a hotel room nearby.  She asked if I would drive her there.  I told her I would need to get my car.  Jill said, “Don’t worry.  We’ll get it in the morning.”

In her hotel room, we sat on the bed and kissed.  I laid her down on the bed, took off her shoes and then pulled her dress above her waist.  I took off her panty hose and then her panties.  She was naked from the waist down.  I started feeling her pussy and began to eat her.

Jill had a beautiful pussy.  As I was eating her, Jill kept saying, “I didn’t think men liked to do this.”  Eating her pussy, I occasionally tickled her asshole with my finger.

Jill had an intense orgasm.  I kissed her on her lips and she told me, “I can taste myself on your lips.”

Then Jill told me it was my turn.  We both got undressed and she started sucking my cock.  We arranged ourselves in 69 with her on top.  I again started playing with her asshole.  She told me she liked this.  I then moved her and licked her asshole with my tongue.

She moved off of 69 and just sucked my cock.  She told me if I came in her mouth, she’d give me a kiss.  I came, and we shared my cum with a kiss.  Years ago, I did this with a High School girlfriend, and I still enjoyed it.

We played around some more and I was hard again.  Jill’s pussy was wet.  I got on top and started fucking her.  After I came, Jill went to the bathroom to get a warm wet towel so she could clean my cock and balls.  While cleaning me, she tickled my asshole.

I was hard again.  Jill got on top and started fucking me.  Jill was amazed I was hard again.  She told me her last boyfriend was 10 years older than her and had trouble getting hard.  This was my third orgasm; I was glad I hadn’t jacked off for a while.  We fell asleep naked.

In the morning we fucked again.  Jill called my boss and told him she needed to spend the day with me to discuss business.

We had breakfast, went back up to the room, and fucked some more.

She drove me to my car.  I got to her office in the afternoon.  She locked her door and I fucked her doggy style with her dress up while she leaned forward on her desk.

That evening, Jill and I spoke on the phone.  She said she was sore from all our activities.  In a 24-hour period, I ate her, she blew me, and we fucked five times.  She mentioned her last boyfriend that couldn’t get it hard.  I was 28 and Jill was around 48.  Her last boyfriend was around 58.  Today I think, “Poor guy.  They hadn’t invented Viagra yet.”

We started making plans for our business trips together.