Teasing on The BaybyJackFlash1959©
** Dear Reader, this story contains graphic depictions of adults enjoying sexual activities on a sailboat. I hope you enjoy it and it gets you hard or wet :-) Please send me your comments so I can improve my writing. Apologies for any grammar or spelling mistakes! Enjoy!! - Jack
I filled the Explorer with sailing equipment and set off down the street to the local Starbucks. My wife hated me to sail alone but not enough to always come with me. That left me to find sailing partners and if I couldn't, sometimes I sailed alone anyway. She just always felt better if I had someone else on the boat. This Saturday morning, I was a bit late picking up my administrative assistant, Kim, and her husband Josh. Neither had sailed before but both were excited to learn.
I own a 35 foot Morgan Sailboat. She is big and broad and not very fast but she is clean and stable and an easy boat to sail. I enjoy sailing and I enjoy introducing people to the fun of sailing.
I pulled into the parking lot by Starbucks and found Kim waiting for me inside. "Where's Josh?" I asked.
Her big brown eyes rose to meet mine and she shook her head gently. "He's not here. He said he had some work to get done." She looked away and then down at her coffee.
I bought some much needed coffee and we climbed into the Explorer and began our drive to the boat. It was a quiet drive even though I tried to make conversation. Normally, Kim is talkative and engaging but this ride was difficult so I turned up the tunes and drove a little faster.
We had the boat ready pretty quick, the Yanmar diesel hummed nicely and we pulled out from the dock, out of Annapolis and into the Chesapeake Bay. She sat in the cockpit just looking around. Her brown hair, roughly parted in the middle, fell loosely around her shoulders.
It only took me a few minutes to raise the Main sail and unroll the roller furling jib. Turning off the engine, I smiled at her as the gentle breeze took hold of my Morgan and drove her forward.
"Here, take the wheel, will you?" I asked.
"Are you kidding? I get to steer?"
I smiled. "If you don't, who will?"
"I don't know what to do?" Her dark eyes sparkled, a little scared and lot excited.
"Just turn the wheel left and right and feel the boat move left and right and for now, aim for that big bridge over there." I pointed toward the Annapolis Bay Bridge that crossed the Chesapeake Bay. "Oh, and try to miss the other boats!"
I went below to double check the engine fluids and make sure the junk in the cabin was secure and wouldn't bounce around too much if we started hitting waves or gusts of wind. Before climbing up the steps to the cockpit, I looked at Kim and wondered what really transpired between her and her husband.
She had a small attractive face. It was heart-shaped and somewhat plain. With the exception of a small amount of eyeliner and a little eye-shadow, she wore no makeup. Her neck was thin and regal leading to soft round shoulders and almost muscular arms. She was 5 feet 6 inches but a bit stocky around the middle. A young woman of 25 years old. She wore a tan sweater vest that was a size too small for her torso. Underneath her sweater vest were large, long and round breasts. At work, I had over compensated by avoiding looking at her, fearful that I'd grow a woody under the desk. Ironically, my efforts resulted in her wondering if I even liked her! We had resolved that through my assurances to the contrary but I knew that it sometimes lingered in the back of her mind.
Perhaps, that was why she was so hesitant to be on the boat alone with me ... she didn't think I liked her. Ironically, nothing could have been farther from the truth.
Dark brown shorts extended down her legs to mid thigh and were lose about both the waist and her thighs. Though she was slightly overweight, she had thin thighs and legs which were pleasing to my eyes. I felt myself harden when I thought about the two of us alone on this sailboat for the day.
For me, I had my usual orange boxer swim trunks and a T shirt that I took off as I climbed the stairs to the cockpit. I'm no stud. I'm mildly overweight too but she didn't seem to mind as I noticed her checking me out as I put sunblock on.
I handed her the tube of sunblock and took over the wheel. She worked it into her skin and I felt myself harden again. Embarrassed and hoping to not cause controversy at work, I sat down and tried to hide my thickening hard on. I think she noticed anyway. After a few minutes of her working the somewhat chalky sunblock into her smooth thighs, I asked her to take the wheel again.
She was a natural at sailing. I can honestly say that she was the best, first time sailor I had ever encountered. She worked the wheel and suggested adjustments to the main and the jib. The wind cooperated and we were at a small cove by 11:00 am. I dropped anchor and we sat quietly and just let the wind whisper to us for a while.
She brought lunch and I brought the beer. I am always careful about how much beer I drink when I'm captain but that doesn't mean I abstain completely! "What kind of beer do you want? Corona Light or Sammy Light?" I called down as she prepared sandwiches, chips, pickles, cheese, crackers, grapes and a cut up apple.
"Oh, I don't drink often." She replied up from the galley.
"What does that mean?"
"It means I'll have a Corona Light but I shouldn't have more than one."
"Why is that?"
"I get crazy when I drink. I don't think I shouldn't have told you that!! After all, you are my boss!"
I considered what she had said and stared at her as she came up the companionway. She leaned forward as she put the food on the tray in the cockpit. Her cleavage looked larger than I had ever noticed before.
"What?" she asked half kidding.
I thought she had caught me gawking. I thought quickly. "First of all, on the boat, I am not your boss. I am the captain and for safety reasons, you need to do what I say but ... we're not in a safety situation here. Second, what happens on the boat, stays on the boat. Agreed?"
"Oh yes. Of course. That would be good."
"You were nervous about that?"
"Don't worry about it. What is this ...You get 'crazy'? What the heck does that mean?
"I don't know. I guess I get a bit more relaxed when I have a beer than I normally would."
"Lots of people loosen up with a beer."
"Not like me." She said with a slight giggle and smirk.
I thought to pursue it further as I was extremely interested how my usually very proper admin 'get's crazy with a beer'! I thought better of pushing it too far. "hmmm ok, well, don't worry about it as I have some diet soda in the cooler down below."
She took a long drag on the Corona and smiled. "No, this is nice and cold and tastes very good. I'll just make sure I don't have more than 1 today."
We ate and talked. She finished her beer and started a second. She opened up and told me that she and her husband, Josh, were not doing well. They had been fighting over stupid things for weeks and he hadn't kissed her in two weeks. Essentially, they were young couple who hadn't quite figured out how to share, communicate and he was using any leverage he had to manipulate her and bend her to his will.
Despite the bimini over our heads, the sun warmed our skin and I noticed tiny beads of sweat forming on her forehead. "Go for a swim?" I asked.
"No, I didn't bring my bathing suit." She said with genuine sadness.
"Mind if I do?"
"Not at all. Go ahead and get cooled off while I swelter and suffer!"
I laughed. "It's your choice!" I called as I tossed myself over the side forming a dive as I hit the water. It felt great as I swam back and forth and treaded water.
She looked at me with a frown on her forehead. "If I come in ... will you promise to not look when I come in the water and not look when I get out of the water?"
"Sure" and I faced away from the boat.
It took a few minutes but I heard a giggle and a splash behind me.
"Oh my GOD! This is fantastic!" She exclaimed.
"Can I look, now?" I chided.
"Yes, but don't stare!" she kidded back.
I was greeted by the site of her treading water 4 feet from me. She had on her bra. I could not see lower but it was a tan bra and while she treaded water, the tops of her floating breasts bounced rhythmically back and forth. I tried not to stare but that made my slight staring all the more obvious.
"Your staring." She stated flatly with a smirk.
"I can't help myself. I'm only a man!"
"I'm a married woman. You're a married man and I'm your employee."
"I'm a married man and when we are out here, I'm not your boss"
"Oh, I forgot that part again."
We swam around the boat, raced the length and I figured out that she was in her bra and panties. She probably showed less with this outfit than she would with a bikini bathing suit.
I climbed back into the boat several times and dove off the cabin roof. It was a blast. I grabbed a new beer and she asked for one too. I jumped in using a life saving jump where your head is supposed to stay above water. The idea is that you are able to keep your eye on your victim. This is made harder when you do it with two Corona's in your hands so my head went down but I kept the beers above water. I call that success!
I returned to the surface to hear her laughing and clapping. We tossed the beer down as swimming in the brackish water of the bay can make you thirsty. I put the empties at the top of the ladder and we decided it was time to get out.
"Well, princess, how would you like to do this?"
"Hmm" She thought. "You turn around and I'll climb aboard. When I'm all dressed again, I call you and you can come on up. How's that?"
"Works for me" I said but felt that I'd really rather watch her ass climb the ladder! My cock was running down my swim trunks and I wondered how I would be discreet getting back on board the boat.
My desire came true. I faced away but heard her struggling to pull herself up the ladder because the ladder of my old boat doesn't extend into the water.
"Shit! Can you help me?"
I turned around to find her tired and hanging on the bottom of the ladder.
"Give me a boost, ok? And this stays on the boat, too!"
With my left hand, I held the side of the ladder. I wrapped my right arm around her knees and then pulled up lifting her up to the bottom rung. She slipped a little and I was holding her soft thighs. She pulled on the rungs and parted her legs to get her right leg up on the next rung and I was left holding her left leg. She slipped again and slid down through my arm until my hand was holding her crotch and ass. They both felt nice and I felt myself harden further though she was able to quickly grab hold and pull herself away from me. I watched her ass climb the ladder and as she climbed into the cockpit, my mind filed away the shape and form of her ample breasts as they bounced in her bra. Under the water, I absentmindedly grabbed and stroked my cock through my swimsuit.
She gave the "all clear" but I could not come up. I was still hard.
"Come on up!" she called a second time.
"Uhh I can't right now."
"Why on earth, not?"
"Hmmm ... Kim, you're an attractive woman and well, I'm only a man. I think you understand that I need a few minutes to calm down."
She giggled. "Why thank you for that compliment! Josh says I'm too fat to have that effect on men anymore. I guess he was wrong!"
"Go ahead and enjoy my misery!" I laughed. "You'll get yours. What goes around comes around somehow, y'know!"
I faintly heard her say "I'd like to get mine some time!"
I was semi-erect when I came up and dried off in the cockpit. She was back in her sweater-vest and baggy shorts but obviously no underwear. I enjoyed the view of her long nipple poking through the sweater material and I got hard again.
"You better stop looking or just get used to walking around with that pole in your pants!"
She was enjoying this. I sat next to her in the sun to dry off and she leaned into my chest. I put my arm around her with my hand on her bicep. She sighed and rolled slightly so that my hand fell onto her breast.
"This is nice" she said with closed eyes as the sun dried and warmed us.
"Yes, it is" I replied as my hand gently cupped her ample tit. Her nipple poked into my palm and my cock thickened. Her tits were much bigger than I originally thought. My guess was that she would fit nicely into a size 34D or DD bra but as I really looked at her, they were actually bigger. They were big enough to "smother your mother" as friends used to say. She spread her legs to let the warm breeze up her shorts to cool the heat emanating from her crotch.
She slid down a bit and put her head on my thigh as the gentle waves rocked the boat. "What happens on the boat stays on the boat" she softly whispered.
"Yes" I said quietly back.
"Can I do this?" she asked and without looking at me, she slid her hand under my pant leg and found my cock.
It felt good. Actually, it felt great but I thought of my wife. Despite our lack of sexual activity in the last 3 weeks, I did not want to cheat on her. Guilt wracked my bones except one, the one in Kim's hand.
"We shouldn't." I stated calmly as her small hand stroked me. "I'm married, you're married. Probably not a good idea"
She pulled her hand away and I got up, ate a chip and sat in the shady side of the boat opposite her.
"Don't get me wrong" I continued. "Kim, you are a beautiful, sexy and vibrant woman. I just don't think we should do something we might regret later."
She stretched a little like a cat. "Well, thank you ... I think!" she giggled. "I'm happy that you find me attractive. I'm just very ummm excited right now and it has been a while for me. I mean, Josh and I have not been doing too well and I just needed some release." She took another sip of her beer and I took a long sip of mine.
I was delighted that she wasn't offended by my brush off. A gentle breeze kicked up and her hair lifted off her shoulders as it dried. Her dark nipples were visible through her tan top. She caught the direction of my eyes and we both looked away but I realized that she had looked down, down to my crotch where my thick and long cock was clearly visible through my bathing suit.
"Well, I didn't mean we couldn't still have fun. I guess I was saying that we need to be careful how much fun we have."
She smiled. Then she grinned, her white teeth shown and then her tongue licked her lips. "WELL THAT'S CONFUSING!"
We both laughed at that and then were silent for a moment.
"Hmm. Well, can I do this?" Her hand slowly went up to her ample bosom and her fingernail traced a line around her nipple while her eyes never left mine. The nipple continued to harden and poke through her top. My cock throbbed in response.
"If it feels good. Sure, why not?"
"How about this?" She put her bottle down beside her and her hand slid up inside her top and cupped, squeezed and pulled on her other tit while her other hand never stopped teasing her other nipple. "I mean this feels much better."
"I'm sure it does. It certainly looks better." I said as I 'adjusted' my cock as it was getting uncomfortable.
"My, watching you do that looks better too." She smiled and I smiled back. "Why not rub it for me? It's kinda too big to be stuck in those shorts."
"Oh ... I'll show you mine if you show me yours kind of game?" I asked with a chuckle.
"Well, sure but we don't want to have too much fun, now do we!"
I pulled the waistband of my shorts out and the head of my cock shot up in relief.
She slowly lifted her sweater vest up revealing the bottoms of her tits. Indeed as she sat there with her back straight, her tits hung below the bottoms of her elbows. Her nipples were long and thick. They weren't eraser head nipples which are beautiful in their own right, these were bigger and thicker than eraser heads. They were as thick as my pinky and about half as long. They were the longest, thickest nipples I had ever seen. I had to check to make sure that my mouth was closed. With her sweater staying nicely above her breasts, she cupped each tit with a hand and pointed them out at me. They were magnificent, full, thick tits with chocolate colored nipples. I must apologize for going on and on about her tits, but I had never seen anything like them. If you like big breasts and nipples, these were breasts that belonged in the museum of breast beauty!
Her thumb and forefingers squeezed her nipples and pulled them. She moaned and her head rolled back. "That feels so good. I mean to have the sun on them." Then she looked at me and I knew that it was my turn.
I lowered my shorts and my throbbing cock shot up. "Can I do this?" I asked. I made a circle with my thumb and middle finger and tried to stroke my cock ... but it was thick and hard for her and barely fit. I slowly went up and down the length of my cock.
"Yes, that looks like fun. You can do that while I do this." She slid her shorts down and kicked them off. "Oh, the breeze feels nice but it is hot here."
Her pubic hair was neatly trimmed above her pussy lips. She opened her legs and her fingers spread her pussy lips showing me her hole and clit. She used three fingers to rub her clit and then her other hand lifted her tit to her mouth and she sucked a nipple in. "Am I still a beautiful, sexy and vibrant woman?"
"Yes" I dumbly responded and stroked my cock. Precum soaked my mushroom head and I spread it around for lubrication.
She reached beside her and grabbed the Corona bottle. She pointed to the neck. "I can see that you are much thicker than this." And then she pointed to the bottom "and almost as thick as this."
She parted her pussy lips with her fingers and pushed the neck of the bottle slowly into her cunt. I watched in fascination. I stopped stroking as I was almost cumming. She leaned back slightly and slid her butt down on the seat cushion. Her arms formed a V by which her tits squeezed together as she used both hands to slide the bottle neck and in and out of her pussy. "Ohhh this feels really good. I guess I can do this but you look really uncomfortable over there."
I got up and kneeled next to her and she licked the head of my cock. The veins that wrap around my cock were straining and bulging. Her sucking sounds made my head spin and she sucked my cockhead so hard that when it came out it made a pop sound. The breeze brought her pussy juice smell up to me and I knew I had lost all composure. "Yes, ohhh yes, you can do that!" I exclaimed more of my cock entered her mouth.
It was exquisite. The sensation shot electric pulses to my balls and they tightened. With her eyes closed, she drew 4 of my 7+ inches passed her teeth and along her tongue and started down her throat. Warmth, wetness and hard pressure engulfed my thick member as her lips spread wide to hold as much as she could inside her. She bobbed her head and the head of my cock rode in and out of her throat. This was the best blow job I had ever had.
I watched in fascination as the Corona bottle plunged her cunt with one hand and her other hand's fingers played over her protruding clit. She stroked it like a mini cock as her head bounced on my cock.
A sailboat motored by 100 yards away and I barely noticed or cared. I ran my fingers through her hair and she said "Please, stop holding back and cum in my mouth. I want to taste you!"
I was beyond holding back anyway and as she dove onto my cock, she grasped my balls and played with them between her slender fingers. My cum felt like it started in my toes and shot all the way up. It squirted into her waiting mouth and eager tongue as she swallowed every drop.
She milked my cock with her hand while clamping her lips around the head and sucking as hard as she could. After several squirts, I had nothing left but she kept sucking and my cock stayed hard.