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.
“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 much 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.
I spent fifteen to twenty minutes attending to Mandy’s tits. I put a small hickey on the inside slope of each tit. As I firmly placed a kiss between her tits, I let my hands slide slowly down Mandy’s back. I let them land on her tight round ass. Squeezing both of her butt’s cheeks, I pulled her tightly to me.
Her hands continued to hold my head tightly to her chest between her tits. I placed another hickey there.
Slowly, I slid my hands down her legs to behind her knees. Then moving my hands up again, I raised the back of her skirt as I went. I again squeezed her pantyhose covered ass.
Mandy stepped out of her shoes and kicked them aside.
Releasing her butt, I unzipped her skirt and let it fall to the floor. She stepped out of her skirt and kicked it aside as well. She stroked the hair on my head laying between her tits as I lowered her pantyhose. I pushed them off her butt and rolled them down her legs. She stepped up and allowed me to push them off her feet. That left Mandy standing before me in nothing but silky white panties.
She was moaning and groaning as I kneaded her ass and the back of her thighs. As I was rubbing up and down the back of her thighs, Mandy opened her legs just a little. I continued rubbing the back of her thighs but moved my hands further around her legs. As I slid my hands up the inside of her thighs, Mandy spread her legs wider.
I kissed my way down her flat belly. She giggled when I delved my tongue into her belly button. With Mandy still stroking my hair, I kissed my way down to the top of her panties. Slowly and gently, followed her panties’ waist band with kisses as I lowered them off her hips, I kissed my way down her abdomen until I was in a position to kiss the top of her slit. I then quickly pushed her panties to her knees. Her pubic mound was covered with a bush of curly red hair that matched that on her head. When I kissed her in the middle of that bush, I pushed Mandy’s panties to her feet. When she stepped out of them, I tossed them onto the pile of her clothes.
Taking one of her butt’s cheeks in each hand, I pulled her to me and licked the top of her split.
“Oh!” Mandy gasped. She spread her legs wide, pivoted her hips, and pushed her pussy toward my face.
I gave her slit another quick lick before I reached up and took both of her hands in mine. I stood and held her arms out to her sides. Looking her up and down, I said. “You’re beautiful, Mandy!”
She lowered her head and said nothing.
Lifting her chin, I looked her in the eyes and told her, “No, really! I think you are beautiful. There are a lot of guys who don’t know what they’re missing. I’m so glad you agreed to have dinner with me and you’re here with me now.”
Mandy slowly raised her head. She was smiling broadly. She then practically leapt at me and we both fell back onto the couch. I fell to a sitting position, and she straddled my legs as we landed.
I massaged her nude ass, and she passionately kissed me. In the mean time, she unbuttoned my shirt and pushed it off my shoulders. We stood again let my shirt fall to the floor.
I then scooped her slender body up into my arms. I carried her the few steps to the bed and gently laid her down.
She didn’t say a word. She simply stared as I unbuckled my belt, unzipped, and lowered my pants. Her eyes widened when she saw the bulge in my shorts. She gasped as I lowered my underwear. A thick six and a half inch cock popped out and stood at attention for her. She continued to stare but said nothing.
With a chuckle, I asked, “What’s the matter, Baby? Haven’t you ever even seen a man’s cock before?”
“Yes! But it was my dad as he came out of the shower a long time ago. I was about thirteen and it wasn’t that big or pointing up like that.” Mandy seemed a bit frightened.
“Oh shit! You’re a virgin! Mandy, honey, maybe you better get dressed, and I’ll take you home.”
“No! It’s OK. I want to stay.” Mandy pleaded. “I’m an adult, and I…ah…want to…ah… be with you. You’re the first man who didn’t laugh at my little boobs. Even Dad teases me about them.”
“Are you sure, Baby? I’m twice your age, and I don’t want to hurt you.”
“Yes! I’m sure. It’s OK. Come to bed. I’m just a little scared.” Mandy was almost pleading as she held out a shaking hand.
How could I, or any red blooded guy, refuse such a plea. I took her hand and crawled in next to her. I turned the lamp off but left the bathroom light on. The light coming from the bathroom gave Mandy a beautifully soft glow.
Mandy cuddled up to me and we kissed. Softly at first, the kiss built in passion. When we broke our kiss, I slid down her body and resumed kissing and sucking the nearest tit while fondling the other. When Mandy’s breathing began to quicken, I trailed my hand down to her crotch.
Mandy tentatively spread her legs offering me access to her snugly closed outer pussy lips.
Gently, I began petting Many’s virgin pussy. When she spread her legs a bit wider, her never opened lips parted ever so slightly. I continued to gently pet her pussy as I would a beloved pet. When I kissed my way down her body, she spread her legs giving me room to lay between them.
When I kissed her pussy, Mandy gasped loudly. “Oh my God!” I burrowed my tongue into her snug lips near her asshole. One long pussy lip parting lick from her asshole to her clit caused Mandy to gasp loudly again, spread her legs as wide as possible, and arch her back.
She reached between her legs and pulled my face tightly to her pussy. Breathlessly, she cried, “OH! Yes! Please do that again.”
I was more than happy to oblige. I love eating a nice pussy. Over and over, I licked her pussy. Mandy quickly began to lubricate. She was soon soaking wet with her own juices. I repeatedly drove my tongue into her tight virgin hole.
Mandy instantly tensed when I sucked her clit into my mouth. Her legs shot straight out. She thrust her hips up to my mouth. She shuddered and cried out. “Oh God! Yeeesssss!”
She continued to shudder for nearly a minute as her orgasm washed over her.
As she lowered her hips, inhaled deeply, and relaxed, I said to her, “Aaah! There’s nothing like the taste and aroma of fresh young pussy.”
Mandy giggled, held her hands open to me, and replied. “Please, come up here.”
I crawled up her body until I lay over her. Mandy passionately kissed me, before saying, “So, that’s what I taste like. Did you like me? That’s what being eaten is isn’t it? God, that was wonderful.” She then licked all over my face cleaning her pussy’s juices off me.
As Mandy licked and kissed my face, I put the head of my cock to the entrance of her pussy. With a passionate kiss, I slid my cock into her virgin hole. When I bumped into her resistance, she gasped. I stopped. “You want me to stop, Mandy?” I asked.
“No!” She stated emphatically. “I want you to take me. Please, go ahead.”
Hugging her tightly, I pulled back an inch or so, paused, then drove fully into Mandy’s depths.
“Oowwwwwww!” Mandy yelled as her tears started flowing.
I held still with my cock deep in Mandy’s speared flesh. I kissed her ear and neck. I could feel her pussy slightly loosen. Her pussy was adjusting to the new invader in its depths. After several minutes, her tears subsided and she hugged my neck.
I asked, “Mandy, honey, are you OK?”
With a quivering voice, she said, “Uh huh. I’ll be fine. Please, don’t stop.”
“OK, Baby.” I kissed her lips again and slowly began stroking in and out of Mandy’s tight hole. In a short while, she began timidly returning my thrusts. Given the tightness of Mandy’s freshly deflowered pussy, it didn’t take long for me to be close to climaxing. I tried to hold off the inevitable as long as possible, but it was no use. With one final thrust, I buried my cock in Mandy’s core. I pumped my load of cum deep in Mandy’s tender depths.
“Oooooo. I can feel you. You’re getting off in me, aren’t you?” Mandy asked.
Holding her tightly, I said, “Yeah, Baby. Damn you feel good to me.”
“Ummmmm. You feel good to me too.” She cooed.
We laid lock together until my cock softened and I carefully pulled out of Mandy. I was done for the night. Oh, to be twenty-two again.
We cuddle and talked for an hour before she got up to dress. I got up and started to dress as well. “Do you have to go? If you do, I’ll take you home, honey.”
She giggled and said, “Stay in bed. I didn’t tell you before because I didn’t know you, but I live only three houses down the street across from the motel.” She jotted down her number on the note pad beside the bed. “I hope you call me the next time you’re in town.”
I got up, hugged her, and said, “You can bet on it, Honey. I’m in Chicago at least once a month, and I’ve found a young jewel in this big city jungle.”
We kissed long and passionately, and she walked out the door.
I used to dread jobs in Chicago. From that night on, I looked forward to and volunteered for any assignments there. Mandy made the long, lonely, nights a pleasure. I just need to see my doctor for a little help. The little blue pills should help me keep up with Mandy’s young wants and needs. I wonder if she likes to travel by car?