It was time to leave, everything was ready. For the next four to eight weeks it was just me and the wind. Crossing the Atlantic ocean. From the Canary islands to the Caribbean. From there to the United States, and eventually back from Newfoundland to the Azores, back to Ireland. Yes, I started there a month ago. Let's say a warmup going south, before the jump across.

Doing everything solo is a risk of course. Can't get sick. Trust my life to a machine for at least half of the trip. On a small boat, not even thirty-five feet, with the potential of waves higher than my mast. Heck, I could lose my life, but about to turn thirty I've already had a great life filled with adventures like this double cross trip. If my time comes while doing something I love, then so be it.

My dad had flown over to wave me off. Sure, he's given me a ton of advice, but nothing to discourage me. He's mighty proud. And with my water tanks full, a nice breeze pushing me out of the harbor, and I'm on my way. I make a few pictures of my dad waving, texting them to him while I still can. And then it's face forward, towards my destination.

My boat, named Solo, can sail itself. And I let it, especially in the beginning, to make sure it's all working as it should, while I'm still fresh. I have all the equipment. Radar. Computer. GPS. Satellite phone. Transponder. Autopilot. Solar power. And plenty of tools to fix anything.

Everything was in perfect order and I enjoyed my first day back at sea. When night started falling I left the autopilot by itself and in the cabin I started working on dinner. I'm not much of a cook but I will survive. That's when I heard a sound that shouldn't be there.

There was a hidden area in the front of the boat and I wondered if an animal had gotten in. With a sharp knife in one hand and a flashlight in the other I opened the small entry to the front area and there was indeed something moving. But not an animal. A young woman looked me defiantly in the face.

My first reaction was to curse. I'd have to sail back and kick her off my boat. I knew I couldn't kick her off in the middle of the ocean. It was as if she could read my mind, as she said, “Please let me sail with you. I won't be a bother.”

So much for solo sailing, I guess. On the other hand she was pretty and looked vaguely familiar. I motioned for her to come out. And as she climbed through the hole she said, “I brought extra food, we won't go hungry”. And when she was out I pointed my flashlight in the space she just left and saw stacks of canned food and dry-packs.

When she stood up in the light and fixed her messy hair, I recognized her. Carmen. One of the girls who worked in the gym where I had worked out in the past two weeks, since I arrived on the island. We had exchanged pleasantries and even flirted a bit. She was very tanned and in excellent shape. It could be fun having her on board.

Before we could talk things over she had to go to the bathroom, which is very tiny on my boat, but still private. She showed me a bottle in which she had peed during the day, but a number two was urgent now. I went outside and emptied the bottle for her, then sat down to think things over.

It took perhaps twenty minutes before she came out of the cabin finally, but she carried two plates with food. She had finished making the meal I had started, and it tasted much better than I had anticipated my own creation would have been. “You let me stay, I cook”, she said in her lovely accent, Spanish being her first language.

I guess it forced an easy decision. Probably not the smartest to base it on good food and good looks, but it saved me from having to sail back, and maybe we had a few fun couple of weeks. Except..

“I only have one bed”, I told her, “we'll have to sleep in shifts.” At night I could turn part of the cabin into a bed, which was big enough to sleep two, but that could be a problem. “I can handle sleeping together, if you can”, she replied, “as long as you don't get me pregnant.”

From everything I packed, I didn't bring condoms, so this could become an issue over time, but it was again too easy to agree with her proposal. “Okay, I can do that. But you will have to learn to operate all the equipment, in case we end up in rough weather and we can't leave the boat by herself.”

Turns out, she had sailed before, and she knew a lot of the important stuff already, and it was a matter of showing how my specific gear was working. More and more I started realizing this could be a fun trip that would not all be on my shoulders.

When I learned that my own father had helped her to bring all her stuff on board, I had to chuckle. She had told him she was my girlfriend and she wanted to surprise me. Both my parents had been telling me for a few years already that they wanted grandchildren, so my dad concluded that putting Carmen on my boat for the next so many months could very well lead to fulfill that desire.

After doing the dishes we decided to make the bed and see how that would turn out. The weather was stable and soft, a slow breeze, and a perfect night for the autopilot. Any ship within five miles would cause an alarm to go off, that was impossible to sleep through. When the bed was made and I was going to put my sleeping tee on, I realized we had a major problem.

All my clothes that were stored in the cabinet on the left, which was more of a vertical drawer, were gone and replaced by her clothes. My dad had told her that the right side had my regular clothes and the left side was just spares, and he had emptied that side out and taken it with him to the shore.

The day before however I had done the same thing, as I had bought a diving suit, and stored it on the right side after moving all my regular clothes to the left. So, all the clothes I had right now were the things I was wearing and the diving suit.

Carmen wasn't too worried, as she told me I could wear anything that belonged to her. It was just the two of us and no one would ever know. As we tried things out, all her shorts were too small for me, and only a few skirts made from stretchy material, like her workout gear, would fit me. So would two of her leggings and a few tops, and all of her underwear. Of course the stretchy clothes were the sexiest things she had brought on board. I guess I'd be washing my own shorts, my t-shirt and my one piece of underwear many times, until we reached the Caribbean.

At least we managed to sleep fairly quickly, but I had vivid dreams about her, and woke up with my hand on her breast, and my underwear wet from cum that apparently I had leaked in my dreams. Carmen didn't mind my hand on her breasts, but she didn't like the cum stuff.

As I washed my shirt and underwear, I had one of her panties under my shorts, which took some getting used to, and I actually liked the workout top she had for me. It was smooth and tight on my body, the only problem was the built-in bra that had some padding. But, she didn't mind, and soon I didn't mind either.

The day was beautiful and I let her sail, explaining everything, and with the bit of experience she had already, she proved to be a good student. I actually had a chance this way to enjoy the view.

When my clothes had dried I put them back on, and I realized the material of her top was actually nicer. Oh well, I'd wear it now and then, as I was sure I had to wash often.

The day went fine but one of the batteries went low. I would have to check the solar panels, but for now I simply started the engine in stationary mode. That should charge the battery in just half an hour. There was a lot of oil though in the engine compartment.

I had to lower myself on my butt in the compartment where I could see the culprit, a leaking valve, pretty quickly. When I put the wrench on it, a huge squirt of oil came out before it stopped, and I was drenched in oil, top to bottom.

The only three pieces of male clothing I had left were beyond cleaning and I could cut some pieces of fabric from it still, to use as cleaning cloth. Ten minutes later, the engine fixed, and after I had cleaned my skin as good as possible, I was back in the panties and top from this morning, now combined with a workout skirt.

Thank God that Carmen was a good sport about it. She didn't tease or laugh, she just acted normal like I wasn't wearing her clothes. Instead she made dinner and we ate under a setting sun which was unexpectedly romantic.

I don't know why I was so aroused by the situation, but in the elastic fabric of the skirt it was suddenly very visible. And Carmen asked if I would like her to take care of it. And I told her “Yes please”.

She took the plates inside and when she came out she was wearing a much sexier top, her breasts on display, her nipples clearly hard. And she sat on her knees on the floor, between my legs, and simply lifted up my skirt and pulled my panties down, and my manhood popped out in her face. And with her mouth she started making love with it.

I had no clue a blow job could be this good, by a sexy woman with her tits almost popping out from her top, and I noticed her nipples were pierced. With her hands around the base and her mouth taking me deep, I could feel her tongue tease the most sensitive part of my dick. And when one of her hands started massaging my scrotum, I reached the point of no return.

I tried to warn her, but she kept going until I blew my load. Not one drop escaped from her mouth as she sucked me completely dry and finally pulled away. I was in bliss, my eyes closed, the waters calm, as I fantasized how my nights were going to be from now on.

I could feel her putting my deflated dick back in my panties until I suddenly heard a click. And when I opened my eyes I saw a tiny metal cage around what was left of my manhood, and she had a tiny key in her hand. And as she said, “Hope you enjoyed that, but I have to protect myself”, she threw the key overboard in the ocean. And when she saw my stunned face, she added “No worries, I have the spare key back home”.

There was not even the smallest bump visible under my skirt anymore, and that's how it would be for months to come. This night turned real quickly from bliss to horror. Although Carmen was pretty easy about it, telling me that I would thank her later, as I would no longer have to fight any desires I may have to fuck her pussy at some point.

In a way the night was more intimate. She allowed me to touch her anywhere but her pussy, and I found that I liked sucking her pierced nipples. She didn't want me to catch a cold and she had me try on one of her nighties. The smooth nylon material felt really nice on my skin, although she suggested we'd shave my body hair the following day. I would enjoy wearing her clothes much more, she promised.

During the night I ended up spooning her, and we both were pretty happy in that position. And in the morning my panties were free of cum. She was serious about shaving though, and while I shaved my face with an electric razor, she took care of the rest of my body and that included my crotch area. Nothing she hadn't seen before, she smiled.

Boy, was she right about feeling better. The top she gave me, similar to the one from the day before, with maybe just a bit more padding, felt like a second skin on me, and with the matching skirt it looked like I had a cute dress on. Just for fun she styled my fairly long hair into a ponytail rather than my customary man bun. And when she plucked my eyebrows a bit and showed my face in a hand mirror, I could only think I looked like a girl.

After about a week we had made good progress, and I didn't even realize anymore that I was wearing female clothing day and night. We had become more intimate though, as she really seemed to like the new me. But everything changed after our first French kiss.

This was not a kiss here or there, a quick peck on the cheek, or a hinky on a nipple in the night. This was mouth to mouth, tongue deep in the other's. Neither of us had started it, the situation asked for it, and we both moved at the same time. A situation where Carmen tripped over a rope and could have well launched her overboard. Had I not reacted on instinct, and caught her in mid-air in my arms.

The realization that one of us could have died changed something in the pleasant relationship we had thus far. Her hands behind my head pulled my lips towards hers, while my arms around her hips pulled her body closer into mine. And the kiss was wonderful!

I could still taste her toothpaste, and feel the smoothness of her perfect teeth. And the tip of her tongue went from one cheek to my other, as if she was measuring the way to my throat. After minutes we finally pulled away, both with a huge smile on our lips. And the realization that I was falling in love made an instant hard-on come up.

Oh, I had felt the discomfort of the cage before. But knowing that I was locked somehow had kept my emotions at bay. Until now. The instant hard-on was replaced by an instant shot of pain, and I cried out. She knew right away what was happening, and I could tell she was sorry now for putting that thing on me.

But, after that first kiss of love, that pressure on my manhood was more consistent, and frustration started kicking in. That night in bed Carmen offered a solution. “Do you trust me?” she asked, and I wanted nothing more.

She blindfolded me and I could hear she was pulling something from her drawer. I was flat on my back as she forced my legs apart, and suddenly something cool and wet was pushed against the entrance of my anus. I gasped, trying to stop her, but again she said, “Trust me”.

It was some smooth plastic or maybe rubbery rod, that slowly pushed past the entrance, the wet lube making it easier. After that first obstacle it became easier, as she pushed it in a bit deeper, then pulled back again, each time going in a little farther. The feeling was one of fullness, like I had to go, but it changed into acceptance, acceptance that it started feeling better and better.

When it seemed like it couldn't go any deeper, she moved it back and forth around a spot that triggered a feeling of pleasure. And as I concentrated on that, the whole thing inside me suddenly started vibrating. The pleasure just tenfolded, maybe more, as a familiar feeling started coming on.

It was an orgasm, and I couldn't stop it, not that I wanted to. I cried out as my body rocked up and down, every nerve on fire. This was not concentrated in my dick, like I had experienced plenty. This was mind-blowing, all over, unstoppable and over loading. I simply kept cumming, higher and higher, until thankfully the vibration stopped.

Exhausted but satisfied I fell back on the bed and I was vaguely aware that the intruder was pulled out from me, my muscles instinctively trying to hold it in. But eventually there was a plop, and the release and relief was final.

Maybe a bit of cum had dripped from my deflated dick, but Carmen said I had cum like a girl. And we both knew this was a breakthrough.