Debbie Takes a Midnight Cruise

DEBBIE TAKES A MIDNIGHT CRUISE

Pretty 16 year old Debbie Waterman was mad at herself. She knew the ruined summer was all her fault. It was not because of the location because she was in a fantastically romantic spot. It was filled with young males with lots of money and lots of time. She shook her head and watched her pigtails swinging back and forth in the mirror. She thought to herself, “They really make me look like a little kid and kind of silly!”

But her real problem was the fact she had put all her chips on the handsome Harvard Sophomore Randall Scott to solve her virginity problem and he never even made the effort.

In fact, she had caught him bending that little slut Heather Murphy over the kitchen sink in “Antonio’s Pizza by the Slice” snack shop this very morning. Her little prick of a boyfriend had played with her ass and fingered her pussy all summer and never once pulled her panties down that far a single time. The sight of her Randall’s thick cock buried inside Heather’s juicy pussy caused her to dump a whole sack of flour on the both of them while they were still hooked up.

Fifteen minutes later she was no longer employed as a waitress in the tiny restaurant.

Angelo the owner even had the nerve to tell her, “I’m going to deduct the cost of that flour from your final check too!”

Since it was almost the last week of the season, she didn’t see it as a major problem. Her rent was paid and she still had most of last week’s tip money unspent. She was really mad because she had wanted Randall’s beautiful cock in her vagina before the end of the season and now her plans were all destroyed.

She took her hair out of the silly pigtails and tied it up in an upsweep pony tail that made her look five years older. She rolled up the ankle length slack and selected a pink pair of hot looking short shorts from her room-mate Jessica’s pile of boy-hunting apparel. Instead of her usual flip-flops, she donned a pair of four inch heels with open toes. When she looked at her ass in the mirror, she could see her ass cheeks were well defined and wobbled seductively when she strolled with a slow motion roll to her nicely rounded hips.

“I bet there are a lot of guys who would like a piece of this!”

But there was no one else in the room to answer her comment.

Bored with her lack of company, she wandered down to the dock area and perched her pretty ass on one of the many mooring stands used for tying up the small boats that used the dock for bringing in fish and transporting tourists to the mainland. She could hear the cries of the birds circling aimlessly over the harbor and the shouts of the fishermen eager to get ashore for the evening’s activities. Her eyes filled with moisture as she allowed herself a moment of self-pity for her pathetic virgin status.

A light tap on her shoulder brought her back to reality. She looked up and saw that it was Captain Ron. Angelo had made a point of telling everyone in the Pizza Parlor that his name wasn’t Ron and that he wasn’t a Captain. Still he seemed like a “Captain Ron” with his ginger hair and his neatly trimmed moustache over sparkling white teeth. Both of his thick muscular arms were decorated with several tattoos related to nautical themes. Debbie estimated him to be in his early 30s and much older than the boys she was accustomed to dating.

“I heard you got fired, Debbie! I hope you plastered that Randall and that silly Heather real good.”

She had seen and talked to Captain Ron all summer but they had never had a real conversation because she was too busy wasting her time on that jerk Randall and she figured he was too old to be interested in a silly virgin like her. Debbie didn’t wear a virgin sign around her neck but she knew her naïve attitude was pretty easy to figure out for an experienced guy like Ron.

“I was ready to quit anyway, Captain Ron. I want to have some fun this last week of summer. I have been so busy working in that little pizza place that I missed out on a lot of fun this summer. But having a job was the only way I could afford to stay here all summer.”

Debbie hoped the handsome older man didn’t see the overflowing liquid in her eyes. She didn’t want to be thought of as a “crybaby”.

“Come with me to a party on the other side of the island. That big shot from Boston is throwing an “all you can eat and drink” shindig before closing up his house.”

He handed her a slice of pizza from the box under his arm.

“You need a little nourishment, girl. You lost a lot of weight this summer, Debbie. You trimmed down real good. I don’t know how you do it working in a pizza place. I have no resistance to Angelo’s pizza.”

She laughed and gobbled down the small slice of pizza. It was her favorite, the plain cheese one.

“You don’t think the “big shot” would be upset at an uninvited guest?”

“Honey, you would be invited to any party just by blinking those big beautiful eyes!”

She laughed and followed him to his cabin cruiser with the twin inboard motors. She liked the sailing boats best of all but the cruisers were a lot more effective in the erratic wind patterns of the shelf.

When Captain Ron encircled her waist with his huge hands and lifted her easily onto the watercraft, she felt a tingle that surprised her because she didn’t think she would be attracted to a guy almost double her age.

They moved out of the bay and followed the coastline keeping clear of the shoals and well-marked hazards. Captain Ron invited her to steer the small craft and told her to keep both hands on the wheel. He stood behind her and placed his big hands over hers making her feel protected and defenseless at the same time.

When she had to turn to the left, she moved her hip back and felt the huge rod suddenly rubbing on her soft ass cheek. For a second, she was flustered and she hoped he did not see her reddened face. After that, she didn’t hesitate to explore the length and girth of his full erection with her naughty cheeks.

She knew Ron was aware of her arousal and when she looked over her shoulder, he took the opportunity to press his lips to hers in a way she had never been kissed by her stupid ex-boyfriend. The combination of the handsome man’s searching lips and his eager cock in her crack brought Debbie to a quick and satisfying orgasm that led the small boat to a series of disorganized headings.

Ron chuckled and straightened the cruiser on the correct heading again and tied the wheel down heading to clear waters. He led her to the downstairs bunk and tugged her hot pants down off of her legs without removing his lips from her mouth.

Suddenly, she was flat on her back and her long legs were wrapped around the Captain with her ankles locked together guiding his inquisitive cock into her still locked vagina.

When he felt the obstruction of her hymen, he looked down into her eyes questioningly but she just nodded her head and pushed up to help him get past the last barrier to her full-fledged womanhood. She expected pain but it never occurred and his long cock buried itself right down to his balls slapping noisily on her soft ass cheeks.

When the ultimate flood of creamy cum began to fill her quivering love channel, she breathed a sigh of relief because she had been taking the stupid pill all summer even though there was nothing to protect against.

The weight of the exhausted man on top of her was not in the least bit annoying. She was glad he was leaving his thing inside her. It was acting like a plug to keep the sticky juice deep inside her vagina. She even didn’t mind when he toyed with her clenched pucker hole. Captain Ron was a lot more aggressive than any of the boys she dated when it came to pushing inside her brown eye. She started to breathe a little erratically as his naughty finger explored her rectal channel.

“Oh my God! I think he is going to make me take it back there as well. Not only am I losing my silly pussy cherry, but now I am going to lose my anal cherry at the same time.”

The depraved thought brought Debbie’s legs up high on Captain Ron’s back almost to his neck and her brown eye was up high and fully exposed for his explorations and possible use.

The experienced mature man slid his cock out gently from Debbie’s pulsating pussy and replaced it firmly right on her quivering pucker hole. She gasped at the touch and willed herself to relax and let it happen right on the vibrating boat with her pussy already filled with satisfying creamy cum.

She felt her sphincter give way and before she could tell Captain Ron to “go easy”; he had stuffed the entire length of his nine inch cock deep inside her pretty bottom. Debbie hooked her ankles behind her head to allow the muscular man deep penetration of her squishy bottom. She felt stretched to the limit but it was a nice feeling and one that was totally unexpected. Her mom had told her it was a pretty good alternate route to keep from getting pregnant but that was because she never told her mom she was planning to take the pill all summer.

When she looked down below her belly button, she could see the long, hard cock being withdrawn and buried deep with a rhythm that matched her panting needs.

Debbie reached down with one hand and started to stroke her clitoris the way that always made her have the strongest of orgasms.

Captain Ron watched her with an amused smile on his face.

“Get it good, girl! Daddy has a nice load to put on deposit in your pretty little backside. Do you want it now?”

“Yes, please, Daddy, give it to me. Give it all to me. I can take it, Daddy. Stick it to me hard, nice and hard. Oh, yes, spank me with those juicy balls. I love that meaty sound.”

The confidant self-assured man grabbed Debbie’s shoulders and pushed her down harder around his thrusting cock and shot his huge load in long spurts deep up into her clutching gut. She screeched like an impaled alley cat cornered in the dark. Her orgasm subsided slowly with a series of uncontrollable grunts out of character for her inexperienced years.

When he pushed her head down to clean up his battered cock, she was hesitant because of where it had just been poking, but she submissively opened her mouth and was surprised how nice it tasted with her own familiar scent.

Captain Ron patted her on top of her head and told her,

“You are a good girl, Debbie. I didn’t know you were a virgin, but I guess we both have something to remember now. You have just been “around the world” with Captain Ron. I have to tell you that you are the tightest pussy I have had for a very long time.”

Debbie kissed his tattoos and his lightly bearded chin, and then she pushed her tongue inside his mouth and explored his wet and willing lips. It was not one of those silly boy-girl kisses that never meant anything. It was a deep soul-baring kiss that told him she was his to use in any way he desired from that moment forward.