Private Investigators Chance Encounter with a Beautiful Young College Girl

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The Desk Clerk

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 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 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. 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, 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.

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 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. It’s hard to turn off the investigator’s curiosity in me. “If I were your age, you’d have to beat me off with a stick. There’s a boy some where who is missing out on a sweet young gal.” I told her.

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. “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, 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 replied. 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?”

“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, 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 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.

“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.”

“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.”

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. Reaching around her torso, I 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.

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.

I spent fifteen to twenty minutes tending 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 until they landed on her firm 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 I moved my hands up again, raising the back of her skirt as I went. I again squeezed her pantyhose covered ass.

Without pulling away, 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.

As I lowered her pantyhose, she stroked the hair on my head. My head was still lying between her tits. I pushed her pantyhose off her butt and rolled them down her legs. She raised one leg at a time and allowed me to push them off her feet. Mandy was left standing before me in nothing but her 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 a little 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, I followed her panties’ waistband with kisses as I lowered them down and off. I kissed my way down her abdomen until I was in a position to kiss the top of her vaginal slit. I then quickly pushed her panties to her knees. Her pubic mound was covered with a bush of auburn 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. She stepped out of them, and I tossed them onto the pile with the rest 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 straight out to the 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 I’m really happy you’re here with me now.”

Mandy slowly raised her head. She was smiling broadly. She then leaped at me. We both fell back onto the couch. I fell to a sitting position, and she straddled my legs as we landed.

I massaged her bare 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 when 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. Please let me 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. Please, come to bed with me. I’m a little scared, but I’ll be OK.” Mandy was almost pleading as she held out a shaking hand.

How could I, or any red blooded guy, refuse such a plea from the beautiful creature lying before me. 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 slowly 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 body to her crotch.

Mandy tentatively spread her legs offering me access to her snugly closed outer pussy lips.

Gently, I began petting Mandy’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 widely spread her legs giving me room to lie between them.

I kissed her pussy, and Mandy gasped loudly. She hissed. “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 down 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. Mandy quickly began to lubricate. She was soon soaking wet with her pussy’s 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 when I flicked my tongue over her clit. She thrust her hips up to my mouth, shuddered, and cried out. “Oh God! Yeeesssss!” She continued to shudder for nearly a minute as an orgasm washed over her in waves.

As she lowered her hips, inhaled deeply, and relaxed with my head still between her legs. I said to her. “Aaah Mandy! There’s nothing like the taste and aroma of fresh young virgin pussy.”

Mandy giggled, held her arms open to me, and replied. “Please, come up here.”

I crawled up her body until I lay over her. Mandy passionately kissed me then licked my lips. She commented. “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 from me.

As Mandy licked and kissed my face, I placed the head of my cock at the entrance of her pussy. As we passionately kissed, 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 go ahead. Please, take me.”

Hugging her tightly, I pulled back an inch or so, paused, then drove fully into Mandy’s depths.

“Oowwwwwww!” Mandy yelled and held me tightly to her body. Her tears started flowing.

I held still. My cock remained buried deeply in Mandy’s newly spread flesh. I kissed her ear and neck. I could feel her pussy’s walls relax a little. Her body was adjusting to the 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 answered. “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 into Mandy’s core. I pumped my load of cum deep into tender depths as she moaned in pleasure.

“Oooooo. I can feel it.” She cried as she thrust up to meet my cock. “You’re squirting in me, aren’t you?” Mandy asked.

Holding her tightly, I replied. “Yeah, Baby. Damn you feel good to me.”

“Ummmmm. You feel good to me too. Your juice is so warm. It feels wonderful.” She cooed. Mandy held me tight and quivered as her own orgasm washed over her.

We laid lock together until my cock softened. I carefully pulled out of Mandy. I was done for the night. Oh, to be twenty-two again.

We cuddled and talked for an hour or so before she got up to get dressed. 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 beautiful 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?