All characters are over 18. This is the first in a series I'm writing. IRL I do (and have for a long time) traveled for a living and am writing about some of my experiences. This is a work of fiction but is based on some trips I've taken over the years.
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Alexandria, VA -- 1993
This was my second business trip, heading down to DC. I landed at then Washington National Airport and took a cab across the river to my hotel. I unpacked my suitcase and headed down to the hotel bar and restaurant. I was young and naive back then, ignorant to some of the realities of sex. I had not yet realized that what is pleasing to the eye, and what is pleasing to the touch are rarely the same. Truth be told, even then I had certain fetishes... older women, and chubbier women. An older woman walked in and sat next to me at the bar. She ordered a glass of wine. I sat there and ordered my steak. I finished my dinner, and the bartender asked if I wanted desert or another drink. At 23, I had champagne taste and a beer wallet, so I thought about it and said no to both.
Without looking at me, the woman next to me said to the bartender "Get him another drink and put it on my bill."
Of course, I thanked her profusely.
Again, without looking up she asked, "First business trip?"
"Second", I said, "I'm Jack.".
"Lorraine."
"Pleased to meet you."
With that she finished her meal and ordered a second glass of wine.
"I travel every week. It keeps me sane. I am not the type to stay in an office all day. And besides, I love the perks."
"Perks?" I asked.
"Yes. When you do this more, you'll understand."
"Do you mean like airline points and upgrades and free travel?"
"Yeah those are a few but I don't need them. I have plenty of money and nothing to spend it on."
"Well what other perks do you mean?"
"Jack, IF and ONLY IF you're a good boy for the remainder of the evening you may find out."
Hmmm, I wasn't really sure where this was going, but I was definitely curious. With that, she said she needed to use the ladies, and this was the first time she turned to me. She was medium height, a little on the heavy side... a smaller BBW. She looked to be 50ish. Her tits were big but not enormous... a strong D cup. Interesting thing about bigger ladies... first, though I didn't know it at the time, they universally give amazing head. I have had good head from smaller women, but I've also had some not so great head. I have never been blown by a fat girl when it was anything short of spectacular. The second thing about BBW's is how they carry themselves, and their shape. I'm not into women where in the words of Andrew Dice Clay, "you can't tell where the tits begin and the belly ends." If her belly sticks out further than her tits, it's a showstopper. This woman was the opposite. She was curvaceous. Slim but round butt, wide hips, and what appeared to be extraordinarily strong very sexy legs.
"I'm going to use the Ladies. Order me another glass of wine and another drink for yourself, on my tab. Have the bartender bring the bill as well. When I return, we will get to know each other a little better."
I did as requested, as did the bartender. Upon her return she took her seat, and we made some chit chat. Turns out she was a partner in a NYC IP law firm. Divorced, no kids, doesn't want any. While we were chatting, she kept leaning into me, showing cleavage, and would occasionally brush her leg against mine. As is typical of a 23-year-old guy, a stiff breeze gives them a hard on. I wasn't full on hard but had a semi that was getting extremely uncomfortable. I politely excused myself to go to the bathroom, take a leak and re-adjust. When I got up her eyes went right to my jeans and checked out the noticeable bulge. Upon my return, she had just finished her wine.
As I finished my drink, she said "Okay, Jack, I'll let you in on one of the perks. There are a lot of lonely people on the road. We are away from spouses, boyfriends, family. Sometimes, it's nice to have a little company."
"Okay," I said.
"So, here's the deal. This is my spare room key." She slid the key card over to me. "No pressure. If you are interested, be in my room in 20 minutes. Just let yourself in. It will be dark. Have a seat on the sofa and wait in silence. If you do that, we will be friends for the week. After that, it's no strings attached. No phone numbers, no emails, nothing. If you are not there in 20 minutes, I will have the room rekeyed, and we are done. Fair?"
"Fair", I agreed.
She looked at my bulge again and gave me a wry smile,
"I have a funny feeling you won't disappoint."
I went up to my room and took a very quick shower, dressed and looked at the key. 1220. The penthouse floor. Off I went. When exactly 20 minutes had passed, I used the key and opened the door. I started to say something, but she cut me off.
"You must be a good boy."
So as requested, I sat on the sofa. Once I was seated, she lit some candles.
The first thing she said was "Okay, the first rule is let the first one happen."
