More of my First Experience with an Older Woman

The tight grey dress she was wearing when I first met her, she borrowed from her 19-year-old daughter.

We first met with the other �Big Shot� Executives at a restaurant.  After everyone else left the restaurant, Jill and I stayed and had a few more drinks.  We lived in the same Metro-Area.  Jill didn�t want to drive home after dinner, so she booked a hotel room.  Jill was drunk and I drove her to her hotel.  In her hotel room, we started a 20-hour period of wild sex I previously described.

Jill and I traveled on business together.  We had to give the appearance that nothing was going on, so we got connecting rooms.  Sometimes we�d stay over for the weekend.  Some hotels printed receipts with different dates, so the company paid for our �Weekend Vacation.�

Although Jill was older, she had a bland sex life.  She liked exploring sex.  I was younger and Jill was also amazed that I kept getting hard.  Her last boyfriend was about 10 years older than her and had trouble getting an erection.

Jill liked oral sex and 69.  When I came in her mouth, we would share my cum with a kiss.  I liked this.  We masturbated in front of each other.

She liked me playing with her asshole and licking it.  She �returned the favor� and I enjoyed this.

I was the first guy to fuck her in the ass and she liked this.  I brought her a vibrator.  She surprised me by putting the vibrator in my ass while she sucked me.  I enjoyed this.  She sat on my face and I licked her asshole while she played with her vibrator.  She also licked my asshole while she or I jacked me off.

Jill didn�t live all that far from me so we saw each other when we weren�t traveling.  When her teenage daughters were not home, we enjoyed Jill�s great big house with it�s outdoor hot tub.

Life was great.  I was exploring sex with a �Hot MILF,� traveling and staying in First Class hotels, while eating in the best restaurants.  All at the company�s expense.