Traveling for a living can be a boring and lonely existence. As an investigator working in the trucking insurance industry, I spent roughly three weeks per month on the road.
It didn't take long to realize that the better hotels and motels are the only places to stay. You just never know what you'll get with the cheaper places. Therefore, I have stayed at the Holiday Inn almost exclusively, for a number of years. With few exceptions, they offer clean, comfortable accommodations at a reasonable price at many locations across the country.
The particular trip during which the following incident occurred found me in Chicago. When in the Chicago area, I usually stayed at the Willowbrook, Ill. Holiday Inn. I had stayed at that motel on this trip as well.
After a long day in the Chicago inner city, it was good to get back to the friendly faces of the Holiday Inn. I had enjoyed a very successful day. I had saved my client insurance company several hundred thousand dollars by recovering a stolen trailer and its cargo.
I was in the mood to celebrate. My celebrations usually consisted of going to a nice sit-down restaurant, instead of a fast food joint, and having dinner and a drink. Normally, these dinners were spent alone.
I knew there was a Chi Chi's Mexican food restaurant somewhere near the Willowbrook Holiday Inn. That seemed to me like a good place to go that night. I just couldn't remember exactly where it was located.
As I passed through the Holiday Inn lobby, the desk clerks were in the middle of their shift change. I waited patiently for things to settle down at the desk and then asked them where the nearest Chi Chi's was located. A new desk clerk, who was just getting off work, offered me directions. I was immediately taken by that lovely young lady. Her name tag indicated said "Mandy." Mandy was a cute young thing. At approximately six feet, she stood nearly a head taller than I. With red hair, green eyes, and a slender build, Mandy was a statuesque beauty. I later found out she was twenty one-years-old and a student at Northwestern University.
Mandy told me the closest Chi Chi's was located one mile west at the next traffic light. I seemed to remember it was about a mile west of the second light. But no matter, I'd find it.
"Are you sure?" I asked her with a smile.
"Yes, quite sure." She replied.
She was a cute young gal, so I offered her a deal. "I'll tell ya what I'll do. Come to dinner with me. If you're right, I'll buy. If I'm right, you buy." Either way, I had no intention of letting her pay. Hell, most college students are always broke. Her co-workers convinced her to go with me. They had known me for years. They knew I wouldn't do anything stupid to hurt her. They also knew I wouldn't let her pay for dinner, no matter who won the bet.
Mandy giggled and agreed to the bet. She grabbed her purse and off we went. We were both wrong! The Chi Chi's was west of the second light as I had thought, not the first. Mandy had looked a little nervous on the ride from the area she had said the Chi Chi's was located. Fortunately for her, it was two miles west of the second light. That allowed me to buy dinner without looking like I was giving her a gift. Hell, I was just happy to have such a cute young lady with whom I could share dinner. Laughing, I told Mandy, "Oh, well, I guess I was wrong too. Looks like dinner will be on me."
Mandy smiled broadly and said, "Thank you."
As we entered the restaurant, I told her, "I know college kids are always broke. They are lucky to have the money to buy a pizza."
"They sure are. At least this one is." She said with a smile.
"What's your boyfriend going to say if he finds out his girl went to dinner with an old fart twice her age?" I asked.
"I don't have a boyfriend. Never have had a steady boyfriend." She seemed just a little irritated with that bit reality.
"Why wouldn't a cute girl like you not have a boyfriend?" I asked. It's hard to turn off the investigator's curiosity. "If I were your age, you'd have to beat me off with a stick. There's a boy some where who is missing a sweet young gal." I told her.
She grinned broadly, shrugged, and said a simple, "Thank you. I guess my height scared off the high school boys, and the college guys seem to want the more glamorous girls."
The waitress appeared about then to take our orders. She opted for a Margarita and I ordered a CC & Coke to sip while we waited for our dinners to arrive. We finished the first drinks and ordered a second as the food was served. We chatted through dinner about my job and her school classes. By the time we had finished, Mandy was getting a little case of the giggles. "Sorry, I don't drink too often, and I seem to be feeling a bit silly." She apologized. "There's no need to apologize. You're fun to be with, and I've enjoyed your company. I'll see that you get home safely." I promised. I paid the check and left a tip as we prepared to go. Mandy took my arm as we stood to leave. She stayed on my arm out the door and to my car.
"Thank you for dinner." She said. Mandy then gave me a sweet little peck on my cheek.
I told her, "Thanks are not necessary. It's been my pleasure to have dinner with such a sweet, cute, and humorous young lady. If you'd agree, I would like to do this again the next time I'm in Chicago. If you don't have a boyfriend by that time, that is."
"I think I'd like that too." She then hugged my arm to her chest and kissed my cheek again.
We continued to chat as we returned to the Holiday Inn. As we pulled into the parking lot, I asked her, "Where's your car? Or, if you prefer, I can take you home."
Mandy stared at me for a few seconds as if deep in thought. She then she smiled and asked, "May I come in for another drink?"
"Of course you may." I cheerfully replied.
Mandy took my arm again as we walked to my room. She was still in her Holiday Inn uniform and would not be allowed to drink in the bar. So, I ordered our drinks through room service.
We sat on the love-seat sized couch and chatted while waiting for our drinks. The drinks arrived soon enough, and I handed Many her margarita as I returned to the couch. Turning toward her, I raised my glass and toasted her. I said, "Here's to the cutest dinner date I had in a long time."
She smiled, took a sip, and said, "I guess most boys don't think I'm cute. Take a good look at me."
"I am, Mandy! You have a cute round face surrounded by a lovely halo of soft, curly, auburn hair. You have beautiful green eyes and a nice slender body. I don't see a thing about you that isn't likeable. There's not a thing about you I don't find appealing? What's not to like?"
"This!" Mandy stood and lifted her pull-over top. She wore no bra. "My boobs are the size of eggs, and boys like them bigger."
Still sitting, I could see her breasts weren't much more than plump peaches. They were topped by quarter sized areolas and nipples the size of small peas. Given their small size, there was no sag whatsoever. I told her, "Mandy, I think your tits are more than adequate. They are much more than eggs. I'd say they are more like delectably soft peaches. I like them. I think they look wonderful."
"Really, You like me...er...my boobs?" Mandy seemed shocked that I liked her chest.
"Absolutely! I think they look delicious. Let me show you. Come closer." Mandy took a couple of steps closer to me. I stood and hugged her tightly. Then without any resistance from her, I pulled her top over her head and off her arms. Tossing her top to the floor, I turned her and pulled her bare back to my chest. Reaching around her torso, I cupped both small tits in my hands and gently kneaded them. Her nipples quickly hardened and grew to the size of a pencil erasers. Sure her tits were small, but they were more than adequate to please a middle-aged man.
Mandy moaned as I tenderly squeezed her tits and rolled her hard little nipples between my thumb and index finger. She laid her head back on my shoulder, and I kissed neck and nibbled her ear. I pinched her nipples just a little harder.
