Back in 2000, I was doing a lot of traveling for my sales job. I was in the middle of a spring sales trip to the Pacific Northwest visiting clients and meeting a few new possible customers.

I was at the Portland airport bar near my gate when an attractive older woman approached. She was well dressed in classy business attire. She sat across the bar from me as I watched basketball on the TV. Our eyes made contact a few times, we smiled at each other, typical random interaction.

My gate was right next door to the bar so when staff finally announced that my flight was starting to board, I went to the restroom and then boarded. I sat in the fourth row on the aisle. The flight to Boise was not even half full so there were plenty of seats.

I was casually watching others walk past me to pick a seat when I saw the older woman. She smiled as she approached and asked playfully if anyone was sitting in the seat across the aisle from me. I laughed and told her “No, I think it’s empty. It’s all yours.” She introduced herself as Sharon.

Once the plane pulled back from the gate, she initiated the conversation. “So, are you going home to Boise or for business?” Sharon was fishing. I explained I was seeing three customers in Boise tomorrow and then on to Seattle tomorrow night. We asked each other about what we did, where we lived, etc. All innocent conversation between two business travelers.

When the flight attendants came by for drink orders Sharon told me, “Let me buy you a drink. I have tons of free coupons from Southwest. I travel three or four days a week.” One drink turned into two during the short flight. During this time, she asked where I was staying, and I simply mentioned the area. She told me that was where she was staying too, and her hotel name. My hotel name.

I laughed and said, “It looks like we’re at the same hotel.”

As we were walking through the Boise airport, I said good-bye and that I was headed to the car rentals.

“So am I.” The same car rental company. As we stood in line waiting at Hertz she handed me her card, “After you get to your room and get settled call me. I’m heading to the hotel bar later.”

Naturally, we ended up at the hotel front desk at the same time. We both checked in and as she was leaving, she asked me if I knew where the bar was located. “I’m here five or six times a year, of course I know where the bar is located. I hope Andre is working tonight.”

Her face lit up, “You know Andre too! I hope to see you there in thirty minutes.”

I went to my room, washed up a bit, and flopped on the bed. It was only 8 pm, but I was a bit tired. I really wanted another drink after my long day. I thought to myself, 'She’s hitting on me!' Then I thought, no, she is a business traveler like you, and is probably just lonely and wants some conversation, just like you when you’re on the road. After a few minutes stretching out on the bed, I headed down to the bar thinking it will be an innocent conversation.

When I entered the bar, I saw Sharon chatting down at the far end. She noticed me and told Andre, “There’s Mike, right there.” Andre turned around, recognized me, and waved.

I sat next to Sharon and Andre told us, “Two of my favorite regulars. What are the odds you two met on the plane?” She had obviously filled him in on our meeting.

Over the next ninety minutes, we had several cocktails, talked about business traveling, our jobs, relationships, kids, etc. I learned she was divorced, mainly due to her traveling. She was fifty-two, fourteen years my senior, and had twin daughters in their final year of college at USC. “I’ll be happy when I don’t have to pay tuition to USC!”

Andre came by and told us, “It’s last call, nine-forty.”

She leaned over and whispered in my ear, “I love sex. And I love sucking cock. Do you want to come to my room?” Then kissed me on the cheek. I looked her in the eyes and told her I’d love to accompany her back to her room.

Once in her room, I just went for it. I took the lead and she liked it. Our clothes came off as we kissed on the bed and our hands were all over each other’s bodies.

Sharon was a beautiful woman with a great personality. She had a magnetic energy. She had lovely long brown hair, brown eyes, and a sexy Mediterranean skin tone as she was 100% Italian. Average height, about five-seven I’d guess without her high heels, size eight, and nice rebuilt breasts, full 36D’s. I later learned she had a Mommy Makeover for her forty-fifth birthday. She was very passionate, loved foreplay, and had a high sex drive.

I was making her moan as I sucked her tits. I’d go up and kiss her, back to her tits, repeat. I kissed my way down her stomach and she knew, so she spread her legs. She had a cute thin landing strip, so I started to lick right down her trimmed bush and all the way down her pussy. As I slowly worked my tongue up and down, she let out a slight sigh, “Oh, that feels so good. Go slow, I like it slow.” So, I went slow.

After I inserted a finger, she got into a rhythm and continued as I had inserted two fingers. I was kissing, sucking, and licking her lips and clit, but all slowly and softly. Her hips begin to go a bit faster, so I started pressing up towards her G-spot. “Oh, yeah, now faster.” I love a woman who is confident enough to tell a man what she likes and give directions.

I focused on her clit and started sucking it hard, flicking my tongue as fast as I could. Sharon was squirming, moaning, and had both hands on my head when her breathing stopped, her body shook, and she climaxed letting out a loud, “Yes!” Sharon followed that up with a soft, “Yes! Yes! OMG! After a short pause, “Mike, you know how to eat pussy!” Her juicy pussy was flowing and there was a large wet spot on her bed.

I looked up to see her with a giant smile. “Come kiss me you stud.” I moved up and kissed her. In doing so my hand went between her legs and landed in the wet spot. I laughed and said, “Wow, you are wet!”

“Yeah, but I’m not a squirter.” We both laughed. But I questioned that statement.

As I held this MILF goddess in my arms we kissed some more, and she caught her breath. She asked where I learned how to give oral. I told her I had a college girlfriend who taught me everything. “She taught and showed me her bits, told me what felt good, and what didn’t. I should probably track her down and send her a thank you card.” We both laughed.

As I caressed her babelicious booty she reached down and took my dick in her hand. Upon touch, I was hard as a rock. She pushed me to roll on my back, “Remember, I love sucking cock,” Sharon giggled.

And suck cock she did. And balls. And give me my first rim job. I might have been more vocal than she was. Many “aahhhhs,” and, “oh yeahs,” with a couple of requests to either lick my shaft, suck my balls or focus on the head. After about ten minutes of enjoying Sharon’s oral talents, I told her to get on her knees.

She did as I told. As I kneeled behind her I admired her pussy lips between her legs. I licked my fingers and began rubbing her lips, “Mmmmm, yes. But give me your big fat dick. And fuck me hard.” Not wanting to disappoint this older beauty I rubbed the head of my pink steel up and down her pussy and slowly penetrated her swollen lips. She was so wet from sucking my dick that I entered her easily. I started with long slow thrusts of my hips, pulling back slowly, and then taking my head all the way out.

To spice it up a bit I grabbed her long hair and pulled her head back. “You want to be fucked hard? You like it hard and rough?”

Sharon muttered back, “Yes, fuck me hard. Make me your bitch tonight!” With that statement, I slapped her ass and just started pounding that pussy like the man possessed. Within a few minutes, she was breathing heavily and released a few primal sounds, so I knew she was about to orgasm again. Not five seconds later, I felt her cunt twitch and clamp down on my manhood.

Once she finished riding the pleasure wave I pulled out. My cock was covered with her cum, and she stated dripping my baby pearly jizz from her box. I told her, “Suck my cock. Taste your creamy juices. Clean up my cock.” And she happily obliged. It seemed that Sharon would do whatever I asked.

Without any break I then told her to get on her back. I stood up and pulled on her legs, so she is on the edge of the bed. I slapped my cock on her pussy and clit a few times and she grinned. “Oh, fuck yes. That feels so good. Give me your dick.”

I told Sharon to pull back her legs and I started to fuck her in a nice slow rhythm. Her big tits looked so good bouncing as I thrust, so I started to rub them and pinch her nipples. She loved it, “Pinch harder. Oh, that feels good!” But I wasn’t done with Sharon.

I told her I wanted to bang in a few new positions. Figuring with her age and wisdom she probably had a few up her sleeve. We motioned through three for a few minutes each. Hell, I didn’t know their official names but they’re fairly common now twenty-plus years later. She got me to sit in the club chair in her room, then started in reverse cowgirl and put her feet on the bottom cushion.

Sharon was doing squats and bouncing on my pogo stick with one hand on the arm of the chair, the other was playing with her clit. The sight of this in the dresser mirror was so damn hot! Another was on our sides, her leg up and I was the big spoon behind her. And the last was sort of a lotus thing with her legs wrapped around my waist as we sat upright and made out like sixteen-year-olds in the back of Dad’s Buick.

I wanted this woman to ride my cock in cowgirl so I could fuck her and suck her tits at the same time. She was happy to fulfill my desires. We started slowly first kissing, then I begin sucking on her tits. As I picked up the pace, she sat up a bit and the sight of her tits bouncing was intoxicating.

Recognizing her calling card as her breathing changed, so I knew she was close, and so was I. She leaned forward towards me a bit, and I just fucked her as fast as I could. We both were stammering words like, “oh ya,” and more “aaahhhhs.” when I felt her pussy clench onto my cock as she rode another wave of euphoria. The next thing I knew I was letting out a grunt and blew my big load of spunk in her pussy.

Sharon collapsed on top of me, and we rolled on our sides. I looked into her eyes and saw the look of a satisfied woman. I kissed her and told her that was fantastic. We lay there for several minutes as our bodies came down from the endorphin high.

It was late, almost midnight, and I figured I’d go back to my room for a good night’s sleep. As I begin to say something she asked me if I’d spend the night, explaining that she enjoyed sleeping with a man snuggled up to her. I joked and told her that was funny because I enjoyed snuggling sexy women. We chatted some and soon fell asleep.

Her alarm went off at 6 am. I was wondering where I was and then I realized I had a woman’s head across my chest. Oh yes, I’m in Sharon’s room. We looked at each other and kissed.

She said she had an 8:30 appointment and needed to get in the shower, but how about we meet for breakfast at 7:30. I went back to my room, showered, got dressed, checked my email, and made a few calls back east.

When we met at the restaurant, we both had our carry-on sized suitcase and laptop bag, two obvious signs of an experienced business traveler. We had a nice meal and talked about our “sexcapdes” from the previous night. I gave her my card and told her what a wonderful time I had with her. She told me that when she saw me at the bar in Portland, she was attracted to me. She asked if we could meet up again on our business travels. I told her I’d like that.

For the next five years, while I was with that job, Sharon and I would meet up about six times a year. Portland, Boise, Seattle, Reno, Vegas, and San Diego were our regular cities. We coordinated our sales trips and about half the time we spent more than one night together.

We became very good friends over the five years, and we were each other’s “Plus One” at several weddings. I was even her date for one of her twins' fancy wedding in Dana Point. The last couple of years, we even took several vacations together in Cancun, Maui, Austin, and Denver.

About a year later she called crying. She was moving back to her hometown on Long Island. She explained that her parents needed help as they were now in their late eighties. She had just resigned from her job and was selling her home in Orange County. She was moving in two weeks.

We kept in touch for almost three years with texts and calls, meeting up several times when she'd visit her girls in Orange County. After not hearing from her in almost two weeks, I called her and got a disconnected number. What? A disconnected number? I was truly worried. I called the number three times, including once manually. The phone number was no good.

After a quick search, I found one of her twins on Facebook and messaged her. Olivia wrote back the next day telling me that her Mom had been dating a man from Long Island for six months and she felt it best to cut ties with ninety percent of her California and work past, so she got a new phone number. And then in the next sentence wrote, “She really loved you. But she knew you would never leave California, and that the age difference would never work in the long run.”

I messaged her back, “Tell your mother I loved her too. But she knows that. Yes, the age gap. I will always cherish our deep friendship. And joked with her, "And tell your mother we’ll always have Boise.”