Unexpected Adventure

It was just after the Fourth of July weekend, very warm, very sunny, and extremely quiet. I have been lucky enough to have the use of my brother's boat, which is kept on the southern coast of Cape Cod during the summer months, for the next three weeks. Normally, my brother and his wife stay on the Cape over the summer but this year plans changed, and they opted for something different allowing me to take advantage of his 48' fly-bridge cruiser which was sitting idle, as long as I promised to pay for fuel and not damage it. We had grown up around the water, so I was comfortable with the boat and while spending time with him during past summers, I also became comfortable with the ocean in the area around the Cape and Islands. It is not as nice as the Mediterranean Sea, but beggars can't be too selective. At least the price was right and I could relax, plus it was only a short walk from the marina to the beach or into town and some nice restaurants and bars.

During the day I would alternate between the upper seating area which had a large cushion for lounging in the sun, and the covered space in the aft section that was comfortable for snacking and reading. There was another cushioned area toward the bow and a nice salon with seating, a TV, and a small galley for whatever meals I felt like preparing. It had all the comforts of a small NYC apartment and rocked gently with the waves. Clothing was always very casual as might be expected and, in my case, 'optional', with a loose-fitting tee shirt and bikini bottoms with string ties on the sides suiting me perfectly if I wore anything at all. While living in Europe for quite a few years, I developed a preference for female bikini bottoms because they fit my slender figure, accentuated my butt, and went low in the front, something that I thought was sexy. They did attract attention but in general, I did not mind the looks and the occasional whistles were inspirational.

On the third day, I decided to try the beach for a couple of hours in the late morning so I walked from the boat in my usual attire, plus a hat and sandals, carrying a towel, book, sunscreen, and a cool drink in a backpack and a small beach blanket in a canvas bag. It was a pleasant walk and although the beach was a bit crowded, it was still easy enough to find a comfortable spot to set up camp. People were friendly and the kids kept themselves occupied with the water and summer games with friends. Stretching out on the blanket over the soft sand and using the towel as a pillow was marvelous and coupled with the smell of the ocean and the sound of the sea birds and children playing, brought back wonderful memories.

After about an hour of flipping from back to front on the blanket, I sat up to look around and noticed a solitary man sitting on a towel not far from me looking out to the water deep in thought but occasionally turning in my direction when his concentration lapsed. At one point, when our eyes met, he smiled and gave a small wave and I returned the gesture. As I said, people here were friendly so having someone smile at me was not unexpected, and since he was a handsome gent, not unwelcome either.

As the temperature rose and the intensity of the sun reached the limit of my sunblock, I walked to the water to cool off while considering a return to the boat for a late breakfast. The water was cool bordering on cold and the speed of my immersion decreased as the water level rose to my abdomen, shrinking my testicles and making my nipples hard and pointy. This slow torture was too much for me so I dove head-first into the small waves and swam around for a few minutes to warm up before walking slowly into the shallow water and back to the beach.

Upon reaching the sand I was met by the fellow who had been sitting on the towel and he greeted me warmly, almost like an old friend, "Hi, I couldn't help but notice you when you went into the water and I admire your bravery for dealing with the change of temperature as you did. The kids are oblivious to it but as you advance from childhood into adulthood it is more difficult to overlook. You might be surprised to see how many people get to their waist and retreat."

I laughed and smiled as I replied, "The thought had crossed my mind but I was sure that people were watching who would enjoy the spectacle of someone giving up against some chilly water. I was afraid that they would make fun of me and that was more embarrassing than letting out a scream underwater during the plunge."

He laughed at my take on the situation and proceeded to introduce himself as Glenn, a teacher from northern New Jersey who had rented a small place for the month of July with a friend. Unfortunately, his friend was called away on business so he was now staying there alone. Glenn said he considered giving up his deposit and scrapping the holiday entirely when he could not find anyone else to share with, but when his friend said that he would still pay his half and try to come later in the month for a week or so, Glenn decided to enjoy some quiet time and took it anyway.

I shared my story and we chatted amicably at the water's edge for about 15 minutes before I mentioned that I wanted to get my tee shirt to protect myself from the sun and started to excuse myself to walk to my blanket. Glenn apologized for keeping me talking so long and said that perhaps he would see me another time. I agreed that it would be nice to meet up again and extended an offer for him to stop by the boat for a drink if he found himself in the marina. He said that he would like that and promised to visit soon before we went our separate ways.

Looking back as I walked away, I noticed that he was watching me intently, seemingly focused on my hips as they gently swayed in the bikini bottoms, so I waved goodbye to let him know that I noticed. He smiled and returned the wave but still did not look away. I smiled to myself as I slowed my pace and accentuated the motion of my hips ever so slightly as I walked on the loose sand.

I gathered up my stuff and had a leisurely walk back to the marina and the comfortable surroundings of the boat. After taking off my tee shirt and putting away the contents of my backpack and beach bag, I prepared a salad for lunch and brought it to the upper deck along with a glass of cold white wine. Relaxing under the Bimini top and looking out over the marina as I ate was soothing and about as good a pastime as I could have imagined. A nice breeze, the smell of the ocean, and the sound of the gulls were a perfect tonic for a city dweller on holiday.

Late in the afternoon, as the day cooled slightly and the poolside bar became livelier, I prepared a Cuba Libre and moved to the aft seating area to do some people-watching and socialize with other owners and guests strolling along the main walkways facing the slips heading to or visiting the various boats. Mixed in this herd of humanity was Glenn, the fellow that I met at the beach earlier who waved as he came to recognize me and the name on the boat. I welcomed him onboard and offered a drink which he gladly accepted.

The groups of wandering people thinned out over time and the music from the poolside bar mixed with the sounds of conversation and sound systems from several of the boats near me. The atmosphere was lively and the people seemed happy as they mixed and mingled along the dock and on the boats. Glenn and I had a friendly conversation that was lubricated by two Cuba Libres and soon became a bit more intimate. He asked about my preference for bikini bottoms and I laughingly answered by mentioning that they are very comfortable and tend to attract some pleasant attention which he acknowledged in the affirmative and added a big grin. "And the attention doesn't bother you?" he asked.

"No, not really," I replied. "If it ever begins to make me uncomfortable, I will remove myself from the situation but so far it has never come to that. Most people tend to be sophisticated enough to live and let live if you know what I mean."

"Yes, I understand," he responded, "and that is one of the reasons why I like the Cape. Everyone has a mellow attitude, and no one takes notice of two men or two women kissing or holding hands. It is a pleasure to be here and far from New Jersey." With this last comment, Glenn got up and walked to the large glass sliding doors that led to the interior space. "I have never been on someone's private yacht before so would you mind showing me around?" he said.

"Not at all," I replied, "but please overlook the messy spaces."

We went into the main salon and dining area before heading down to the staterooms and the spaces below deck. The areas are a little tight and we found ourselves pressed together on several occasions, in one instance Glenn managed to hold the end of one of the cords on my bikini bottom that allowed the knot to come undone exposing one cheek of my butt as it slipped. "Oops, sorry," he said with a smile.

"No problem," I responded and slowly retied the knot while smiling back. "I don't usually wear much of anything on the boat anyway so the sudden freedom felt good."

"Please don't stand on ceremony on my account. You probably know that I enjoy looking at you and the more I see, the better I like it," he quipped.

"Thank you, you flatter me," I replied. "I knew that you were watching as I walked away from you on the beach, and I assumed that you liked what you saw. I try not to be so obvious most of the time but there are instances when the mood strikes me and I become a bit risqué."

"You must tell me when you feel the mood getting ready to strike again so I can be prepared," he said with a laugh.

"Well, one more Cuba Libre and I will probably turn into a slut so watch out," I replied with a smile as I walked up the steps to the salon.

When we got to the salon, Glenn sat on the sofa and gave me what I can only describe as a naughty look. His eyes twinkled a bit and he flashed a sly grin while gently rubbing the front of his shorts. "I wouldn't mind another drink if you feel up to making them," he said mischievously.

"Of course, but you've been warned," I replied as I went to the bar.

When I had the drinks ready I walked slowly back to the sofa in a sexy fashion and dropped to my knees in front of him as I handed him his glass and placed mine on the coffee table. I reached my hand to the front of his shorts and rubbed the bulge softly while I looked into his eyes and smiled. I took a drink from my glass and whispered, "Dark rum always heats my blood. How about you? Does it make you warm?"

"Dark rum gets me hot," he said, "and then I need something to cool me off. Do you think that you could help cool me off?"

I took a long sip of the cold liquid and held it in my mouth while I unzipped his shorts. Glenn helped by pulling them down to expose his stiff penis which I then took in my hands. Leaning over I guided his dick into my mouth to be surrounded by the cool rum/cola combination and then I started moving my head up and down on his hard cock. Glenn moaned quietly while I gently caressed the head of his dick with my lips and ran my tongue up and down the shaft. Slowly at first and then increasing the tempo I worked his cock with my mouth and sucked in the precum that oozed out in his excitement. His hands grasped the back of my head and he helped move it to the increasing rhythm of his thrusts. His moans became louder and the thrusts deeper into my mouth and down my throat until he cried out and held my head still as the pulsing of his penis began to fill my mouth with hot semen. Shot after shot hit the back of my throat and I swallowed as quickly as I could to keep pace with what seemed like a never-ending stream of cum.

Finally, as he released his grip on my head and the pulsing streams of semen eased up, Glenn leaned back into the sofa cushions seemingly exhausted. I licked my lips and wiped my mouth on the back of my hand then took a long drink from my glass to wash the remnants of his cum into my stomach. "You might have warned me that you were a big cummer so I could have been prepared," I said with a smile.

"I thought that you might like the surprise," he responded laughing.

I stood up, picked up my glass, and sat on the sofa by Glenn. "I hope that cooled you off a bit," I said.

"Yes, it felt very nice, just the thing for a warm afternoon," he replied.

We relaxed for a while, exchanged phone numbers and then Glenn left to head home. He said that he hoped that we could meet up again, maybe for dinner or lunch on the beach, and I agreed. I thought that he might propose something definitive but since he did not, I decided that he might just be someone who was looking for a blowjob and nothing more. I didn't mind so much since I enjoyed some company and had someone to share a few drinks with on a warm afternoon, but I was a bit disappointed.

The next day was very cloudy, so I decided to skip the beach and lounging on the boat in favor of traveling around and visiting various antique shops in the area. It was a wonderful afternoon and I met quite a few nice people in the process. I drove along Route 6A toward Provincetown and even managed to see some local sights and the beach facing the North Atlantic before turning around to head back to my home in the marina.

Since I was not in a hurry and had no pressing engagements, I opted to stop for dinner at a place I knew in Dennis, a bistro-type restaurant favored by the younger crowd and locals in the off-season, with a lively atmosphere and good food. So as not to take up a table to sit by myself, and to be more sociable, I decided to sit at the bar, which turned out to be a wise decision.

Looking over the menu while sipping a glass of wine held my attention but the sound of the door made me turn out of curiosity. In walked a lovely person who prevented me from looking away and who also reduced the noise level as others in the area stopped to gaze as well. This person, androgynous in nature but effeminate and appearing to be more female leaning, looked to be in her mid-thirties like me and was neatly dressed in cream-colored linen slacks and a shirt that showed off her small breasts, elegant sandals, and a black choker. Her hair was blonde and cut in a curly pageboy and she carried a brown leather clutch bag. She stopped momentarily as she entered and our eyes locked when she saw me, not like the acknowledgment of a friend but more like the acknowledgment of a kindred spirit. I smiled and the smile was returned before she walked over to ask if the seat next to me was taken in a voice that betrayed slight masculinity. Intrigued, I said she was welcome to it as I was dining alone and promised not to be too annoying which brought a laugh. She said that she would do the same and introduced herself as Adrian.

"I'm Nicholas, friends call me Nicki," I said. "Are you here alone or killing time waiting for someone to join you?"

"I am flying solo right now," she replied. "I arrived from Connecticut yesterday afternoon and with the weather today, I decided to take a ride around to see the neighborhood. And you?"

"I came from New York a few days ago and I'm staying on my brother's boat for a few weeks while he is away with his family. I took a weather day as well and wandered around the antique shops before coming here for dinner," I said.

"Hmm, a boat must be nice I'll bet. So different from a cottage, adds to the adventure," she responded with a smile. "Have you had any adventures yet?"

"I met a fellow from New Jersey yesterday and I am having dinner with you so, yes the adventures have begun," I joked. "How about you? What are your plans for the coming weeks while you are escaping from Connecticut?"

"I'm meeting a couple of friends and we're going to Provincetown for a little R&R. Connecticut is a bit stuffy so we come here every summer to let loose and enjoy the nightlife. It's refreshing to simply be yourself without the hassle," she said in a serious tone.

"I agree with you," I said and raised my glass in a toast, "Here's to a nice break for both of us."

Adrian raised her glass to clink mine and added, "To a nice adventure."

We chatted like old friends and after the second glass of wine, we shared some of the more intimate details of our lives. Adrian confessed that she was originally known as Andrew and adopted the name Adrian when she began taking hormones and living openly as a female. It had been difficult at times but she has a supportive family and many good friends so she is happy with her decision. I told her about my preference for men and being effeminate during college and afterward, allowing me to grow into someone comfortable with my femininity while outwardly being male. Eventually, Adrian said, "We're not so different you know. I may have small breasts and while you don't, inside we are alike."

I thought about what she said for a minute and responded, "I agree with you," adding, "I'm glad that we met. You have made this a memorable evening, not quite an adventure but a pleasant interlude in the mundane." We had a great dinner and quite a few laughs in the process. As the crowd thinned out it was decided that we would go back to the marina for a nightcap, neither of us wanting the evening to end.

Adrain followed me to the marina in her car and we walked arm-in-arm to the boat enjoying the night air. Once inside, I gave her a quick tour of the premises and then proceeded to make a couple of drinks while she got comfortable, settling on the sofa. She asked that I turn the lights down and put some music on so she could pretend to be a rich lady in some exotic port far from home. I readily complied and within a few minutes she leaned over to kiss me and the night became extremely warm as our bodies got closer and the air more heated.

"Nicki, I suddenly feel really weak and would love to get out of these clothes and stretch out for a few minutes. Would that be okay with you?" she said while giving a fake flutter of her eyelashes.

"How could I say no to such a charming lady in obvious distress?" I replied softly.

"Such a gentleman," she whispered while shifting to get up from the sofa. "Please lead the way so I don't get lost."

I took her to the master cabin where she asked for help removing her clothes. It was erotic undoing the buttons on her shirt exposing her small breasts and erect nipples while she kept her eyes closed. I took her shirt and placed it on the chair and then unsnapped her pants, slid the zipper down, and let them fall to the deck before she stepped out of them for me to fold and place on the chair as well. She stood there topless, wearing white lace panties that did little to conceal the bulge of her penis, and her black choker. As she eased onto the bed she said, "You are quite overdressed my sweet."

Quickly, I removed my polo shirt and shorts and stood looking at her for a moment before getting on the bed as well. "Now, I feel overdressed," she said. "Please slip these from my hips and let me feel you next to me."

The panties came off and I gazed at her nakedness lying on the soft bed before l laid next to her feeling her soft skin against mine. Her penis was not very large but clearly aroused and my erection rubbed against her leg as we hugged and kissed. I slowly worked down from her lips to her neck and then onto her breasts, taking each nipple gently into my mouth before nibbling and sucking, and then on to her abdomen and eventually taking her penis and testicles into my mouth. Adrian was moaning with excitement and wriggling on the bed as I licked and sucked on her dick while gently squeezing her nipples between my thumb and forefinger. I was eager in my desire to please her and it did not take long for her to grab my head and hold it firm as she cried out in ecstasy as she reached her orgasm and her abdomen started to spasm. There wasn't much semen, but she shook from the spasms and was panting heavily.