Traveling for a living can be a boring and lonely existence. As a private investigator working within 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 Holiday Inns almost exclusively, for a number of years. With a few exceptions, they offer clean, comfortable accommodations at a reasonable price at locations all across the country.
The particular trip during which the following incident occurred found me in Chicago in late March. When in the Chicago area, I usually stayed at the Willowbrook, Ill. Holiday. I had stayed at that motel on this trip as well.
After a long day working in the Chicago inner city, it was good to get back to the friendly faces of the motel staff. 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 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 the lovely young lady. Her name tag read, "Mandy." Mandy was a statuesque beauty. At approximately six feet, she stood nearly a head taller than my five foot, seven inch height. Her pale a complexion, red hair, green eyes, and slender build captivated me. In later conversation, I found she was twenty one-years-old and a third year student at Northwestern University.
Mandy told me the closest Chi Chi's was located one mile west at the next traffic light to the north. 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 and since she had already caught my attention, 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 this lovely young lady pay for dinner. Hell, most college students are always broke anyway. The price of a pizza was usually an extravagance.
Her co-workers convinced her to go with me. They had known me for years and 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, but it was further than I had guessed. Mandy had looked a little nervous as we rode out of the area in which she had said the Chi Chi's was located. Fortunately for her, it was two miles west of the second light.
That difference allowed me to pay for 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.
"Oh, well, I guess I was wrong too. Looks like dinner will be on me," I laughingly told Mandy.
"Thank you." She replied while smiling broadly. I could see the tension leaving her face.
As we entered the restaurant, I said to her. "I know college kids are always broke. They are lucky to have enough 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 of reality.
"Why wouldn't a cute girl like you have a boyfriend?" I asked. I'm sorry for being so nosy. It's hard to turn off the investigator's curiosity in me." I told her, "If I were your age, you'd have to beat me off with a stick. There's a boy out there somewhere who is missing out on a sweet young lady."
She grinned broadly, shrugged, and offered a simple reply, "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 drink 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. She apologized, "I'm sorry. I don't drink too often, and I seem to be feeling a bit silly."
"There's no need to apologize. You're fun to be with, Mandy. I've enjoyed every minute of 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. You have had a bit too much to drink to drive very far."
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 with you?"
"Of course you may." I cheerfully replied.
Mandy took my arm again as we walked to my room. She was still in her uniform and would not be allowed to drink in the hotel 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 Mandy 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! I have been looking at you all evening. 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?"
Mandy took a sip of her drink and seemed to be gathering courage. She stood, lifted up her pull-over top to her neck, and said, "This!" She wore no bra. "My boobs are the size of eggs, and most boys my age like them much bigger."
Still sitting, I could see her breasts weren't much more than plump peaches. They were topped by quarter sized aureola and nipples the size of small peas. Given their small size, there was no sag whatsoever.
"Mandy, I think your boobs are more than adequate. They are much more than eggs." I told her. "I'd say they are more like delectably soft peaches. I like them. I think they look wonderful."
Mandy seemed shocked that I liked her chest. "Really? You like me ... er ... my boobs?"
"Absolutely! I think they look delicious. Let me show you. Come closer."
As 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 the rest of the way over her head and off her arms. Tossing her top to the floor, I turned her and pulled her bare back to my chest. I reached around her torso, cupped both of her small tits in my hands, and gently kneaded them. Her nipples quickly hardened and grew to the size of pencil erasers. Sure her tits were small, but they were more than enough to please a middle-aged man traveling alone.
Mandy moaned as I tenderly massaged her tits and rolled her hard little nipples between my thumbs and index fingers. She laid her head back on my shoulder and allowed me to kiss her neck and nibble her ear.
I pinched her nipples just a little harder.
"Oh! Mummmmmm." Mandy arched her back and thrust her chest out to my fondling hands. She abruptly turned and kissed me.
I sat on the arm of the couch and pulled her to me. Her tits were perfectly aligned with my mouth, and I took full advantage of the opportunity. With one arm holding her firmly around the waist, I sucked one nipple and most of a tit into my mouth and worked it with my tongue. With my free hand, I continued fondling her other tit and tweaking its nipple. After a little while, I swapped tits.
Mandy was softly mewing and holding my head to her chest with both hands. She intertwined her fingers in my hair and pulled firmly.
.... There is more of this story ...