Boating Ch. 3

Chapter 03: Paul's Story

This is a true story submitted to me by Paul. He sent it to me after reading Boating 2. He declined to name his country of origin. These are mostly Paul’s words, but English is not his first language. I have edited as necessary, but tried to keep as much original prose as possible.

Everything started when I was 12 years old. A 16-year-old guy convinced me to let him put his prick in my anus. He said that it was a common practice among boys. Innocently I agreed. It was a very painful experience. He used no lubrication and he was very rough and brutal inserting his large penis into my tight virgin asshole. For several days afterward I could barely sit. Defecating was like putting a blazing iron up my ass. I felt I had been raped.

When I was seventeen I had my first sexual experience with a woman. She was middle-aged and worked in a grocery store in my neighborhood. She was ugly and stinking and was furious when she asked me to lick her pussy and I refused. I can still remember her dirty skirt pulled above her waist in the backroom of the store. She had a huge triangle of black hair covering her protruding belly, and her cunt stank. It was disgusting.

After that I decided to give my sexual life a break. It was funny because during a period in life when boys are thinking of pussy twenty-five hours a day, I had locked my sexuality in the darkest slot of my brain.

After graduating from school, I decided to move to a larger city, and look for better opportunities. By the age of 23 I was living in a small apartment and working for a pharmaceutical company as assistant product manager.

My area director was a retired Navy officer in his early fifties. He was tall and had a good appearance. Once I was in his office waiting for him and I saw a boating magazine on his coffee table. I was browsing the magazine when he showed up. He asked me if I liked boats. I explained that I used to sail Snipes in my hometown. From that day on whenever we met, boats became part of our conversation. He told me he was remodeling an old 35-foot wooden hull sailboat. On another occasion he invited me to visit a boat store with him during the lunch break. He was looking for a new compass and a radio.

One day he invited me to visit his boat in the shipyard the following Saturday. He picked me up at my place and his wife accompanied him. I had seen her in some photos he had on his desk. She was much younger than he, in her late thirties, tall, black hair in a very short cut. I found later she was his second wife. She was wearing jeans and an old loose male style shirt. Without being beautiful she was very attractive. She was the kind of woman who is not a first time eye-catcher but whom you slowly learn to value. Her name was Rosy.

The shipyard was almost two hours drive, south of where we lived. It was a very enjoyable day. The boat was beautiful. It was restored to perfection. The plank deck gleamed with varnish. The white hull glowed in the morning sun. All the brass fittings had been polished.

A hatch and ladder located by the helm lead below. The interior was nice. There was a main cabin with two fair size bunks, a galley area, and a small but very practical head with a commode, shower and foldable sink. There was also a master cabin in the bow, separated from the main cabin by a wooden bulkhead and door. The master cabin was mostly one large bed fitted to the V-shape of the bow.

After the lunch we returned home and they invited me to sail with them on another day, after they had the boat fully ready. That time came during an extended holiday weekend.

They picked me up very early in the morning. The area we were going to sail was a 250-mile long inlet, averaging about 30 miles wide, with more than 200 islands. Some of the islands were just a few feet square. Some were large enough to have a city of 25,000 people. A poet once called this tropical paradise ‘precious stones set in a silver sea.

The boat was moored in a marina and after filling it with food, beverage and fuel we set sail. It was one of those perfect mid-fall days. The sun was shinning and a light breeze blowing. As an experienced sea wolf my friend was testing the changes he had made in the boat and the sail gear.

As soon as we left the marina his wife emerged from the cabin wearing a small bikini and stretched out on a towel near the stem. She was a lovely woman with shapely legs and a nice ass. I tried not to think about her. Besides she was the wife of my director. I was sitting with him on the helm deck. He and I talked about boats for a long time.

At one point he changed the subject and began to ask questions about me. He asked about my family, if I had a girlfriend, my plans for the future etc. Then he asked me to get him a beer. When I stood up I looked toward the stern. His wife had removed her bikini top and was lying on her back bare breasted, showing firm tits and erect pink nipples. I turned quickly and stepped below to get the beers.

The rest of the day we spent maneuvering the boat. We sailed close reaches, tacking upwind, and we ran down wind with full sails to see how she handled. It was work raising and lowering the sails so when we sailed back to the marina we all were pretty tired.

After a quick dinner at a restaurant nearby, we returned to the boat. I took one of the bunks outside the master-cabin. I was so tired that I was asleep within minutes of lying down.

I don’t know how long I slept but I woke up and in the darkness. Over the sound of the water mildly slapping the hull, I heard a woman’s voice panting. It came from the master cabin. In the beginning it was like she was trying to restrain herself, choking the sighs. But the panting grew quickly in intensity.

“Yes, yes, more…” she said.

They were having a lot of fun. For the first time in many years, I had an erection. Suddenly, the sounds ceased. I fell asleep again in an aroused state, somewhat frustrated.

I woke up with her tapping my shoulder. I rose and helped her fix breakfast. I could not help thinking about her being fucked by her husband. I could visualize his dick sliding in and out of her pussy. She looked and smelled good. Although I tried to hide my movements, I think she noticed that I kept glancing at her body -- ass, tits, and crotch. I was afraid to look her in the face, although I wanted to study her lips and imagine. At one point, she caught me looking at her, and looked into my eyes. As I looked away, I could see from the corner of my eye that she stared at my crotch for a moment and curled a smile as she noted the slight bulge of my semi-hard cock.

We set sail again and headed to a small island. It had a lovely small beach, no more than one hundred yards long. Golden sand framed luxurious green vegetation. The place was deserted. We dropped anchor a safe distance off shore and I loaded towels into a small inflatable boat. I was preparing to jump in the water to swim and tow the inflatable to the beach when he called to me.

“Do you mind if we talk a while before we land?” He asked with a serious tone in his voice.

I was astonished and couldn’t figure out what I might have done wrong. I hoped his wife had not told him that I had been looking at her. I mumbled that I did not mind. He tapped a spot on the bench beside him indicating I should sit down. I sat. His wife emerged from the cabin and sat on the bench in front of us.

“My wife and I want to know if we can fully trust you,” he said.

I was relieved that they were not upset with me. At the same time, however, I was curious about the direction the conversation had turned.

”You are my boss,” I said,” and I think of you both as good friends. You have all my respect, friendship and loyalty.”

”Thank you Paul, we appreciate your comments. We have been observing you and we know that you are a good guy. The reason for my question is simple. My wife likes to sunbathe nude and well, I don’t believe it would be good for my career if it became common knowledge at the company.”

“We are happy to know we can trust you,” my boss said as he gave me a friendly pat on the back.

His wife looked at me with a pleasant smile and went down into the cabin. We were just finishing with our preparations to go ashore when she emerged from the cabin fully naked.

I felt my heart beat increase. I turned my face away and jumped into the water. As I surfaced, she dove in close to me. We swam toward the beach together. Because I was towing the inflatable she reached the beach before me and gave me a unique spectacle as her nude body emerged from the water. Her breasts bounced erotically as she pranced in the surf. Water dripped down her back to her nicely rounded ass cheeks, and emerged as a rivulet flowing down the inside of her thighs. I had another erection, which seemed to add drag to my swimming and towing.

My boss followed us ashore, and in few minutes the three of us were on the deserted beach.

She spread a beach towel and laid on her back while her husband and I unloaded the inflatable. We had folding chairs, a small cooler, food and an umbrella.

”Hey guys, why should I be the only naked person on this beach? C’mon…” she called.

”Better we get naked as well buddy!” Said my boss.

At the same time, he turned his back and stripped off his trunks. I was a little embarrassed but there was nothing to do but get naked as well. I felt somewhat uncomfortable for the first few minutes but after that I started feeling OK. I set up lunch.

I called them to eat. She stood up and walked to her husband. As they stood together, facing me, I noticed they both had their genitals fully shaved. They smiled. His cock was curved and swollen like a good sausage, not erect, but not flaccid either. One ball hung slightly lower than the other. Her pussy lips were gently folded and slightly wrinkled. Her nipples seemed to poke up directly toward my eyes. She giggled as my faced reddened and I looked at the food instead of them.

After a light lunch they decided to rest and read while I did the housekeeping (or more accurately, beach keeping).

Soon he was a napping under the umbrella. She invited me to go for a walk.

”Paul, are you homosexual?” She asked after we were some distance away from her husband.

I tried to recover from the surprise. All I could mumble was a feeble “No.”

We had reached the end of the small beach. Some large boulders were partially covered by tropical vegetation. She leaned her body on one bolder and said, “Please, you don’t need to be ashamed. There’s nothing wrong. You are a sweet person.”

”But why do you think I’m a homosexual?” I asked. At that moment I was interested in knowing her opinion. Was I different?

”It’s just a feeling. You don’t seem to have any interest in my naked body. It would be normal for a guy your age to be struggling against a hard-on right now.”

I explained my position of respect for her and her husband, and that I felt an obligation because they had confided in me.

”Tell me, what do you think about my body?”

I told her that she was the first woman I had ever seen fully naked. She was very surprised.

I decided then to tell her of my two sexual experiences. It was the first time I had told anyone. I told her of my anal rape and of the frightening experience with the smelly woman at the grocery store.

I noticed that her husband had swum back to the boat. We walked back to our beach site. She patted a place beside her on the towel, a mute invitation to sit down. She took one of my hands and placed on her breast.

“Don’t you think that it’s time to try it again?”

I mumbled something about her husband.

She gave me a sly smile and said, “You don’t need to worry about that. Guess why he went back to the boat?”

(Later on I found out he was watching us from the boat with binoculars.)

Her body was lean. Her tits sagged just a little. Her belly was flat and muscular.

“Kiss my nipples, I love to have my tits caressed.” She said.

At the same time she grabbed my still flaccid dick. It didn’t take much for me to develop a full erection. I bent down and began to lick one of her nipples while I massaged the tender semi-softness of her breast. It was completely different from my previous experience. I had in my arms a wonderful woman. Her whole body exhaled a mix of salt and mild scent from her sun blocker.

She noticed my lack of experience. In fact, I believe she was delighted by it. She leaned back, pulling me on top of her. She was still stroking my hard cock while I kissed and licked her nipples. I was getting quite excited.

She bent her knees and guided the head of my cock to her wet cunt and rubbed it up and down. It was exquisite. The head of my dick penetrated her slightly. It felt like it was at the silky entrance to paradise.

“Put it in me.” She whispered.

My dick had no problem in plunging deeply into her pussy. She held my head with both hands and locked her mouth on mine, inserting her lustful but tender tongue into my mouth. I could feel my chest mashing her tits while she pressed and swayed her belly against mine.

I pumped countless times in her love tunnel. I could feel her muscles inside flex around my shaft. I felt my whole body shaking in a sequence of ripples. She was panting heavily kissing and biting my lips. She raised her buttocks from the towel in a desperate effort to have every millimeter of my cock inserted deep into her body.

My cock swelled and my balls seemed to tighten. The head of my dick became ultra sensitive and I could feel her heat. A gush seemed to start at the root of my shaft and from my balls at the same time. I felt a warm stream flowing from my body, spurting deep within her. We stayed engaged for a long time exchanging kisses and caresses until my dick softened and slipped from her body.

”I hope this time you have enjoyed it.” She said.

There was no need for an answer. I responded to her question with small kisses planted on her lips, cheek and neck.

We sat side by side for a while. I looked at her beautiful body without any concerns. Her shaved-bare pussy was drooling globs of cum. She led me to the surf and we washed each other’s genitals in the emerald green warm water.

We sat back on the towels. A few moments later I saw her husband jump from the boat into the water. He excused himself for his absence. He said he had been talking with some friends over the radio. The rest of the afternoon we spent together like nothing had happened.

After a warm shower at the marina we prepared for dinner. He took us to a nice restaurant at the marina complex. She was lovely. Her magnificently tanned body was clad only in white shorts and a tank top. The seafood was excellent. The wine was also good, but I was not used to it. The long day, the sun, the sex, and the wine made me feel a little dizzy.

I was in a good mood. Better than I had felt in a long time.

We went back to the boat and sat on the aft deck sipping more wine and chatting. The only light was from the distant restaurant and a few of the stores in the marina complex up the street. Our boat was moored at the farthest end of one of the docks.

While we talked he started caressing her bare thighs reaching her crotch. He inserted a finger under the hem of her shorts. She feebly asked him to stop and tapped on his hand but it was clear she didn’t want him take her warning seriously because she opened her legs to accommodate his hand more easily.

Following up on his advance he unbuttoned her shorts with his other hand and began to pull them down. She raised her butt from the seat to assist him. She wasn’t wearing panties. Her hairless pussy was fully exposed.

It was funny to see us pretending to talk normally while she was dressed only with a top and he had a finger working in and out of in her pussy!

”We better go to the cabin, it would be more comfortable,” she said.

They stood up and when they passed by me she whispered:

”You too. Come join us.”

I was astonished with the invitation and was still trying to understand what was going on when she took me by the wrist and added:

“Let’s go. I’m sure you will enjoy it”

After we were all below, She locked the doorway to avoid any surprises, opened all the ventilation hatches and turned on a small fan. In a fraction they were both naked. I was still reluctant in front of my boss, but with encouragement from both of them I undressed as well.

The rest of the night was crazy. We both of enjoyed her mature body. We had sex in many different ways. More than I knew existed up to that time. For me it was a real sex education.

I had the opportunity to kiss her entire body including a sweet smelling and tasting pussy. I licked like I had been starved, which in a way, I had. She reciprocated by giving me a tremendous blowjob while she was sitting in her husband’s lap with his big sausage prick shoved fully into her anus.

Later, while we rested she expressed her desire to be sodomized by me. My dart was only semi-erect after all of the activity. My boss solved that problem. He took my prick in his mouth and sucked it and worked it with his tongue until it was rock hard again. That was another first for me that night; having a man suck my dick. He was good and the sensation was different from when she did it.

After that preparation, it was easy and delicious to shove my tool in her well-lubricated bowels. The mixture of Vaseline and her husband’s jism made perfect fuck cream.

Exhausted from sex and under the effects of the wine we fell asleep. But another surprise was still waiting for me on that memorable weekend. I woke up in the early morning. It was still dark outside. I lay between them facing toward Rosy. I could barely see the outline of her head. She was sleeping quietly.

Suddenly I felt a hand sliding over my bum. I kept still, pretending to be asleep. I was curious to see what was going to happen. One finger slithered inside my ass crack and touched my anus. I noticed my boss was silently moving down the mattress.

I felt his warm breath over my buttock followed by his hands splitting my ass cheeks. A second later, I felt something moist, warm, and stiff pressing against my puckered hole. He was tongue fucking my ass! In the beginning it felt strange. But quickly shock waves radiated from my anus throughout my whole body in an exquisite sensation. Something I never felt before.

To my disappointment I felt him stop his caresses. He was doing something silently that I could not make out. Then I felt one hand splitting my cheeks again and a fingertip covered with by a cold layer sneaked inside my anus. He came close to me and followed with a combination of thrusts and circular movements of his finger inside my rectum. He withdrew the finger and immediately I felt something thicker touching my rosebud.

At the same time he whispered in my ear: “Just relax, it won’t hurt you. Relax and open your anus. You will like it”

I began to panic, remembering the boy many years before tearing my sphincter. He increased the pressure and gently but firmly shoved his knob into my anus. There was no pain, only a stretching sensation. He stopped penetrating from time to time, waiting for my anal ring to get used to the intruder. Then slowly, little by little, he would shove another couple of inches into my rectum.

There was no pain. The stretching feeling was replaced by the sensation of needing to urgently expel something from my bowels. He took one of my hands and placed it on his cock. I touched his rod half-inserted in my butt, and I circled my dilated anus with a fingertip. His cock was throbbing and his balls were trembling. He was excited. My hand feeling his cock pushed half way in my ass excited me too.

He grabbed me by my hips shoved his dick in all the way. After another pause, he began to pump in and out in my rectum. He increased the speed of his pistoning.