Cruising Of A Different Kind

When my wife died, I made a decision to let myself be myself some more; to let myself be a little more gay. At 60 I was certainly old enough not to care what others thought, and it was 2024, if it was a scandal to anyone it wasn't an unusual one at least. My wife had known about my desires, we were open with each other that way - honesty went a long way to a satisfying and enjoyable sex life. I was confident enough to openly wear some things I thought were androgynous but pretty girly to me, even to the office, but no one ever said a word. Some people might guess, but no one knows for sure - yes it might be a dress, but I'm wearing stubble not makeup. I know I'm not fooling anyone with just a miniskirt, but I could wear a crop top too; my body is fine, the face gives it away, and I haven't yet had the courage to get a makeup consultation. From the neck down I could be almost any age.

I am just about 180 cm, 70 kg, quite slim; long legs and a perky little butt, tiny 'almost' breasts with pink nipples. I keep my body smooth all over, usually shaving but I have a laser too. I'm definitely not an alpha top even though I do have a decent size, 7 inches plus; no complaints and more than a few compliments, from my relatively few partners of either sex. I long to be the woman though, to be the mate for a big strong man. I'm not even sure what I really want to be honest with myself, I don't really feel as if I am gay, but I yearned to feel the way a woman feels when a man's penis feels so good inside her that she has an orgasm, to feel that overwhelming giving of myself in return for pleasure that would make me shudder and spasm in ecstasy.

Anyway, after virtually no success virtually, I really wanted (longed?) to make things a little more real, to be somewhere I might have a better chance of meeting someone like minded; or at least not married. I started with getting myself in the waiting line for HRT and therapy, but it was going to be a long while until I got a call. In the meantime, I thought about gay friendly places in Canada where I could be dressed up and no one knew me, like Montreal or Vancouver, and about American places like San Diego and Miami, then I hit upon the idea of a gay-friendly resort kind of thing, and then I found something I hadn't thought about - a gay only cruise. The second I started thinking about being a sexy little bottom stuck on a boat full of ass hungry older men in bathing suits, with nowhere to go, I knew I was in; the idea was immediately appealing and intriguing.

I did some research, and saved some money; made some arrangements like a new passport and someone to feed the cat; and a few months later I was on a plane to Miami, thrilled about all the excitement in store and also about getting past customs in my all plastic chastity cage, so much I had goosebumps and a little dribble problem. I felt so empowered. Maybe I could put down the goosebumps to the air conditioning, but certainly not the dribble, made all the worse by silk stockings and tight pencil dresses and buttoned blouses on the stewardesses; with their perfect hair and nails and manners; so impeccably sexy, my ideal internal representation as a woman. Drop dead sexy. The plane hit the runway and the sudden jolt ended my little reverie of bending over and showing handsome men a bit of bra as I offered refreshments, perhaps feeling their hands accidentally press against my tightly bound thighs, making them helplessly horny as their blissfully unaware wives sat next to them, and spilled another drop of precum to add to the little sticky mess in my soft cotton boyshorts (pink of course) upon the bump of touchdown.

My daydream was replaced with immediate anticipation for the real thing coming up, and I still had girly goosebumps even as I hit the sun and humidity leaving the airport for the ship. My hands with their painted nails may have trembled just a bit as I handed some cash over to the handsome burly shuttlebus driver, and I may have glanced at him glancing at my girlishly crossed legs in the mirror once or twice, and by the time we got to the boat I was just a puddle of girly goo already and thoroughly enjoying my first day in Miami.

Oh dear me, what the hell had I got myself in to, I thought to myself, as I mounted the steps, minding the gap and stepping on board. Suddenly I felt naked, almost fearful, as though all my intentions were exposed, like I was wearing a sign that said 'total newbie beta', and I got goosebumps again, my knees felt wobbly as I wandered anxiously looking for my suite, in fact I had almost forgotten that I was to have a roomie. Since I was a single, I had been bunked with another single for the cruise - I was going to be sharing my room with a complete stranger. All of a sudden I was more anxious, and when I finally found my cabin, I breathed a sigh of relief that it was empty and that I could freshen up and organize my luggage of one entire carry on bag without awkward pleasantries or silences. I knew it would be a top though, because they didn't pair up bottoms with bottoms if you chose that bit on the cruise options, which I boldly did, but 6 long months ago, and now my click was far too late to undo - a top was coming to me. All of a sudden I felt a little pressure in my cage, and knew that my long (so long) fantasized destiny could soon be fulfilled. I was going to learn that it would be, and beyond my wildest imaginings - the next 10 days were going to change me into a completely different person, and persona.

I got my stuff tidied away and changed my shirt and panties, and put on my new skort, which left me showing a lot of leg. I wasn't brave enough to wear the miniskirt yet, or the bikini, but I had them, a few other things, and no real boy clothes at all. That 'oh dear' sensation was replaced with new comfy girl sandals and a deep breath, and I left the room with nothing but my key card and long bare legs. I went down to a bar, found a perch, and waited and watched the crowd mingle and ebb as I sipped my drink. It never even dawned on me there were no women until I heard the PA, it was a robotic female voice announcing departure, and I went out to the rail to wave, with everyone else.

It was fun, and we all re-convened in the lounge as we got underway; I retrieved my stool at the bar and sat with legs politely crossed and watched men laugh and talk with each other, smiling and hugging as groups coalesced. I immediately saw a few 'candidates', but since we were now underway, I was curious enough now to be wondering about my roomie. I wandered back to my room, smiling but feeling a bit awkward still, and as the door clicked shut behind me, I heard the shower. There was a suitcase bear the bunk (I had chosen the top), and a pair of very large sneakers. I got up on the bed and started puttering in an absent minded way, but desperately wondering who was in that shower. Suddenly it was shut off, and my pulse quickened anew, thumping in my chest, my palms clammy. I was suddenly glad I was not standing up because I feared my weak knees would betray me.

The bathroom door opened, and a tall, heavy set man with deep brown skin stepped out, his head almost bald but his chest was covered in tight black curls. He was easily 2 m tall, probably about 3 of me - he was still glistening wet, the muscles shifting in his massive arms as he adjusted the towel at his waist; me trying and failing miserably at not looking at his bulge. I was utterly enthralled, and I became belatedly aware my mouth had dropped open in stunned absorption of what I was looking at. It was like a dream, and then this ebony Adonis smiled widely. At me! His voice was deep but melodic as he spoke, his sparkling white teeth and brown eyes just mesmerized me.

"Well hello! I am so pleased to meet you! I am Paul, from Memphis." I managed to gracelessly climb from the bed, trembling a bit, and stuck out my hand as though to shake his, but of course destiny made it falter a bit and my soft sissy fingers ended up lamely in his palm as he crushed them momentarily, also ending any expectation of my masculinity at the same instant.

"I'm Vivian, Paul, and the pleasure is mine. I'm new to this and I'm a bit nervous", I stammered, suddenly feeling physically vulnerable trapped in this tiny stateroom and this massive man holding my limp little hand still... That startled me from my stiff and awkward pose, but I couldn't stop looking at him, realizing he was a handsome man indeed, his hands were strong but warm, and it was as though in the third person I saw my slender arm and painted nails reach up and touch his thick arm, and asked, "Shall we go and have a drink and get to know each other?"

"Yes", he said in that deep manly voice, and as we left the room, I damn near yelped and fell over as he brushed his hand 'accidentally' against my ass. It was all I could do to stay on my feet until we got to the bar, and found a quiet booth. My pulse was pounding and I was consumed with curiosity and lust. I was trying hard not to show it, but every thing he said; every gesture, every brush against my hand or his knee under the table was like a little shock, I was a hot mess, sitting in the dark with a man I had just met.

That wasn't novel, but the fact that we would be travelling together for the next while was extremely exciting, I was literally shaking with excitement wondering what he would look like naked. And sweating. While he groaned and spewed a huge load of semen inside me. I was scared that he could read me like a book, and his every easy action and effortless maleness said he could. I felt as much vulnerable as I felt a deep desire to be just that, dominated and helpless, a hungry beta bottom for this mighty alpha god. I tried to play the meek coquette, with a bit of real honesty, and maybe it was the second drink, but suddenly I found myself babbling about why I wanted to be a woman, and all about my bra size and how I hated high heels and, and.... his giant hand found and covered mine suddenly; and my voice faltered.

I looked deeper into his eyes suddenly, and saw a gentle amusement there, him tolerating my little girly stories, bemused at my naive ways. Almost as though it was like a crime, he glanced around suddenly, and I felt a massive paw find my thigh as his mouth moved close to my ear.

I was shaking as he whispered "I think you're really hot and I love your stories, you make me laugh with your little jokes too. Let's go back to the room and get a little more comfortable, shall we?" I gulped, took a big gulp of my drink, and he took my hand as I stepped down from the table. We got to the room, and the door clicked shut. My mouth was dry and my heart was pounding out of my chest, I could hear my breath deep and slow, my tongue was tied in knots of anticipation. He sat on the couch and spread his thick legs wide, and then patted the cushions next to him. I slipped off my sandals and sat down next to him, legs curled up and suddenly conscious of his cologne and the heat of his body, the fact that he was so big I was literally falling into him as we sat side by side.

"Oh Paul" I stammered, "I'm so excited, I'm just shaking." His long finger touched my lips, I vaguely noticed his manicured nails as his hot breath touched my neck, his stubble scraping just a bit, my senses were overwhelmed as his mouth found mine and I moaned a bit, feeling all woman and even somehow a bit desirable, or at least desired. I surrendered and my body swooned, and his tongue pushed into my mouth, his first violation of me but it was all I desired. It was everything I wanted, all I could possibly hope for, and all I wanted was more. My deepest desires were being fulfilled, and I was suddenly free of fear and doubt. I wanted this man for real - it was finally, actually happening after so many years of fantasies...