The Pretty Pilot   added 3 years ago
  By: greenbird33  Age: 64  Country: United States

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Categories: The Fetishists, Virgins/Young women, Masturbation, Prostitutes
Tags: pleasurable Older clit bukkake bust cock WANT role
Location: Other
Roleplay: Sugar Daddy/Baby
Fulfillment: Act on it
Nature: Romantic
I recently chartered a small airplane to fly me 400 miles to an important meeting when none of the major carriers served the small rural airport I needed to get to. At the little airport I would be picked up by an executive that worked for me, and we would drive a few miles to evaluate an abandoned factory that might work well for the company expansion.

The plane was a four seat single engine prop and the pilot was a young woman about 30 years old, stunning in her beauty, and so easy to look at. She had black hair in a preppy hair style, with some dark purple highlights. Her face was slightly oval shaped and she had absolutely flawless creamy skin and very light makeup, a bit of mascara and faint pink lipstick on her medium sized slightly puffy lips. she looked so young and fine to my middle age eyes.  I imagined how she would look with her preppy lips tightly sucking on my big throbbing manhood in the men’s bathroom at the airport. I continued fantasizing by saying in my mind, “I know you have a wet, feminine, sexy pussy inside that preppy miniskirt, so let me see it!”


Once we were in the air, she told me her name was Dreamy. She added that I could call her by her nickname, which was “100%” When I asked her how she got the nickname, she said, “I won a bet once.” She blushed and giggled a little girl giggle. I said, “I really like your laugh, 100%. It’s so much fun.” She laughed again and shifted her hips up and down twice in the cockpit. I was so glad I'm the only passenger.  I felt so dirty-good.


“What is your laugh like?” she asked.

“I don’t know, make me laugh,” I replied.

“OK, well sir, how about this?” She asked as she pulled her jacket open and arched her thin body forward like a stripper, and pulled on her preppy breast cups inside her white blouse making it look like she was pinching her nipples. She moaned exaggerating the motion saying, “Oh yes, oh yes, pinch my hot knotted up nipples!” she giggled.

I could not help but chuckle. She said “Sexy laughing man, I might have to jump your bones some time,”
My wedge was upright and straining in my suit pants. I wondered if something white and sticky might go flying out inside my Calvin Klein Black sheer boxers.

I responded to her, “Did you ever fly naked?” I asked.


“Not naked, but lots of times I take my top and bra off and fly topless. I used to drive on the highway topless when I was in college, too!” she giggled. “I never  did it flying with a customer,” she laughed. Once I showed my tits to a taxi driver.


“First time for everything, that’s what I say,” I looked right at her chest.

“What about you Mister?” she asked, “Will you go topless too?”

“Better than that, sexy. I am about to pull it out and show it to you, it’s throbbing after your teasing.”
She kept one hand on the flight console and with the other hand she unbuttoned her blouse. She opened her shirt and said, “Help me get this blouse off, I still have to keep this plane steady.

As I worked on gently stripping the shirt, I asked “100%, how did you get that nickname; what bet did you win anyway?”

Her hand started gently caressing my hand and she smiled. Then she started breathing heavy which made me want to kiss her. I leaned over and opened her wet, preppy, lips and slipped my tongue inside her Juicy Fruit orifice, and she sucked the tongue and put her hand between my legs and rubbed my rod through my William Nottingham wool suit pants. She was about to finish me when I pulled away and pushed her hand away.

She pouted, and I said “I was about to shoot, that’s why.”

“I made this bet,” she said, “with a guy who was gay. I told him that I could get all the men (100%) in a Transmission shop to ejaculate watching me. He figured at least one would be disinterested. So they locked all the doors and I stripped totally naked, and performed without touching anyone. Soon they all had fluid flying and dripping on the cement floor. Then I let them kiss me on the cheek and take a photo with me.”

“Why did you do that?” I asked.

“Five thousand dollars and nobody hurt me!” she said, “You see I am an escort of sorts. This was big money for an hour’s work. My gay friend had also gotten off watching the guys do their thing. So it really was 100%.

I had her blouse off and she was wearing a simple preppy bra with no underwire making her breasts seem to rest naturally. She said, “I’m a 36-C is that OK?” I felt the bra cups and felt her hard nipples.

“Yes, great,” I whispered.

This bra had a front clasp. “Thank you, God” I thought.

I unhooked the clasp and pulled the bra cups away from her young, firm, titties. Out popped big nipples, as big as pencil erasers, and rock hard. I fondled them like a litte boy playing with his older sister’s tits in an adolescent learning session

My hand was up inside her miniskirt pulling her panties aside. I felt the sexy girl slit in her panties. I whispered, “I want to stuff your snatch with my big erection, 100%.”

“Finger me hard,” she whispered. Her preppy butt went up and down as I  complied with this request. Her vagina lips were so tight and smooth and yet her hole was medium sized and wet. I gently but rapidly fingered her wet clit faster and faster as she wriggled her ass around like a cheerleader, and she gushed a cup of liquid as I felt her tunnel contractions.

“Fucck me-e-e oh I’m komming bad boy,” she shouted. The plane tilted and for a moment and I knew I we died it might be worth it.

I was pounding my meat so hard. Suddenly my jelly spurted out in a torrent. A glob went on 100%’s face and she wiped it off with her middle finger and proceeded to go in and out of her preppy pilot’s lips.

“M-m-m-m so tasty,” she said as she wiped some off her miniskirt and applied it to her lips like Chap Stick.

I shot again as I cupped her breast and her chest heaved, and I rubbed jism into the big nipples. I said “I want to suck you like a little baby boy. I want to make you pregnant. I want you to have my baby. I want to be your pimp. I want you to remove your panties and show your coin slot to people in the food court, like teenagers. I want you to pound me off in the movies. I want to take pictures of you giving a blow job to an entire college fraternity. I want to skinny dip with you and do it under a waterfall and see how hard your nipples get. I want to force you to take your clothes off and bend over. I want to take you to a Victorian dance and treat you like a Princess. I want to pay you for an all-nighter. I want you to want me so bad it hurts. I want to do it with you on a pool table.”

She replied only, “OK stud, lets see your net worth first.”

I can still smell her.




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