Becoming a Friend of Dorothy

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A journey from straight to full-blown gay, on a cruise ship.
3.1k words
4.6
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Part 1 of the 3 part series

Updated 06/11/2023
Created 04/24/2022
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It makes sense to start at the beginning but the beginning is hard to pin down. Maybe it's best to go back to when I was 35 and, to the outside world, happily married to Anna.

We had now been married 15 years and she had been my first love. We had decided not to have kids and that was what was making things easier, now we did not get on so well.

Now, I'm no oil-painting, short black hair, green eyes and sticky-out ears but even I was annoyed at how Anna had let herself go. Originally a size 14, she was now up to 22. She had been a pretty girl, natural blonde, with blue eyes and a cute button nose but now the first I noticed was her double chin. Call me vain but I no longer fancied her.

Things came to a head one Sunday when she started complaining about me not being affectionate any more. My response was the beginning of the end for us.

"Do you blame me? The way you're piling on the weight I can't even get my arms around you."

She was shocked but hit back. "So you're saying I'm fat?"

"No shit Sherlock. Collect your prize of another chicolate bar on the way out." It was nasty and I regretted saying it as soon as the words came out.

"You utter bastard!" she spat and she threw a nearby cup at me.

Her aim was off and it smashed against the wall. It was enough to stop us both talking. We stood in shock for a couple of minutes and then I advanced, opening my arms.

"Fuck off, you can't get your arms round me, remember?"

"I'll get some stuff together, it's best I go."

"Yes, it is. Congratulations, you've just ended our marriage." Anna added, almost triumphantly.

I spent the next 3 weeks at a cheap hotel, until I was surprised to find she had moved in with a friend, a male friend and left the flat for me to pay for.

I was only just back when a letter came in advising of our 'cruise itinerary'. I had totally forgotten about our booking a ten night Mediterranean cruise. It had been booked in my name and so I wanted to take advantage of it and get away.

I decided to phone the company we booked with and see if I could get a refund for her booking. A slim chance but nothing ventured, nothing gained.

"I'm sorry, sir but their is no refund available. You will still have the cabin." The girl on the other end of the line sounded truly sorry.

"Are there any options open?" I asked in a desperate tone.

"Well, and stop me if this sounds silly, you could transfer your wife's name to another....but it needs to be done quick. You only have six days left to change, then it's locked in."

"Really? Well thank you, I'll see what I can do."

I hung up the phone and sat puzzled. My best solution was to advertise on Social media but I was not naive enough to think a lady would volunteer herself, for the obvious reasons. I decided to open my search to include men or women.

After much thought, I came up with the following.

'Due to personal circumstances, one of the intended passengers on a cruise booked for two, has pulled out. Now looking for male or female who wish to take the opportunity of a half price holiday. Absolutely no strings attached. Regards Sam. '

There wasn't exactly a flood of interest but on the third day, an email arrived from a guy called Darren. He was really keen and even offered two thirds of the price. I arranged to meet him later that evening, to see if we could work it out.

We met for a coffee and the first thing that struck me was his appearance. He showed me his passport, which stated he was 25 but he looked like he could have been the son I never had. He was quite small, only 5"4, but had clean white skin and blonde hair that reminded me of Anna.

We chatted and got on really well. On a couple of occasions, when I caught his eyes, a strange feeling went through me and I definitely stiffened.

"There is one thing I should tell you, it's only fair." He added hesitantly.

"Go ahead, what's the worst it can be?" I joked with him.

He looked me straight in the eyes and said "I'm gay."

I raised my eyebrows but didn't respond.

He continued "Don't worry, I'm not going to chase you round the cabin."

That made me laugh "Not much room to chase in those things, you'd probably catch me." I realised what I'd said and knew it sounded flirty.

He returned the flirt "I'd rather you chased me."

The smile he gave me, made me so horny and despite being straight all my life, I wanted to fuck his pretty little ass so bad.

"So, the place is yours if you want it."

"Really?" He sounded so surprised.

"Sure, just get me your passport details and I'll get you signed up as the replacement for my wife."

He giggled, "I'll be better than her."

At that moment I had no doubt.

It would be another three weeks until we left and I surprised myself as I could not keep Darren out of my thoughts. Whenever I masturbated, it was him I thought of. I imagined his small body sitting on top of me as I pumped his lovely smooth ass. Where had these thoughts come from? I was straight, wasn't I? Then I remembered my high school days and a friend I had, named David. He was a small lad too, with the same milky white skin. I had tried to suppress the memory but it all came flooding back. That summer day when we swam naked in the lake and started to toy-fight in the nude. I was so much bigger than him and soon his ass was in the air, my hands pinning his legs over his own shoulders. At that point I had felt myself harden and I so wanted to fuck him. The tip of my cock was rubbing his hole and David just smiled and encouraged me on. I no longer had to pin him down, he had already submitted but not in a wrestling way. My cock pushed forward, bringing a gasp from David's lips.

After that was now a blur, all I could recall was David, on his feet, putting on his shorts whilst crying. We never spoke again and I had tried to bury this episode, successfully until now.

The cruise was to start in Malta and so a flight from Manchester, England, was required first. There was an older lady at the window seat in our row of three. Darren put himself in the middle and started to chat to the old lady. I heard him tell her that I was his father.

"Am I too old to be going on holiday with you, daddy?" He had turned to ask, his eyes betraying the flirty nature of his question.

"Nonsense!" The old lady piped up "There's so much you can do together." She added innocently.

My mind was working overtime and i put my magazine over my crotch, to disguise my raging boner.

"Oh, I've got plans." answered Darren and he squeezed my thigh.

I wanted to fuck him so much and he knew it.

Our cabin was as small as I expected but at least we had a balcony. There was a daily newsletter lying on one of the single beds. I lazily flicked through it.

"I see there's a launch party at 5pm, free wine on offer."

"We must go, daddy." Darren laughed as he spoke.

"Enough of the daddy stuff, I don't have a son." I reacted a little over the top, I knew that, but my emotions were everywhere. I continued scanning the newsletter. I spotted that there was a singles club at 10pm and one I didn't recognise at 11pm.

"What the hell are 'Friends of Dorothy'? Is she a special passenger on board?

"Oh very special. In fact I plan on going." Darren answered deadpan.

"Is that the lady you met on the flight?" I queried.

Darren laughed again. "You really don't know, do you? It's a gay thing. Maybe I'll meet someone special." Darren said excitedly.

My heart sank. I had assumed we would be getting closer and now here was Darren looking for a hook-up.

We just went for a buffet evening meal after the launch party and then returned to the cabin to change for later. The drink had made me so horny and I watched as Darren stripped to have a shower. He had a shaved cock, which was bigger than I expected and lovely tight balls. I was lying on my bed, in my shorts and made no attempt to hide my hard-on this time. In fact, I pulled them down to free my shackled cock. Darren took a few steps towards me and said

"I'll do you a deal. I'll suck your cock now, if you come to the Friends of Dorothy club tonight."

How could I refuse. I nodded my head vigorously and opened my legs. His touch was so gentle, yet firm, as his right hand held my cock. He kneeled over me on the bed and lowered his head, encircling my cockhead with his lips. I groaned with pleasure and encouraged, he went all the way down my shaft. I was in ecstasy and knew I wouldn't last long. He sensed that and sucked harder. Seconds later I filled his mouth, jets of spunk flew down his throat. Darren was most attentive, licking my cock clean.

As he did so, I pleaded, "let's stay in and fuck the night away." I tried to kiss him but he shied away.

"You've still to complete that deal we agreed on. Nothing more until then."

Out of curiosity, I went near to where the singles club was meeting. I wasn't encouraged. There was not one woman under 60 and I was determined that Darren would be my next conquest.

Just shy of 11pm we headed down to where the Friends of Dorothy would be. The age range was a lot wider and some of the lesbian chicks were hot but of course, untouchable. Next thing I knew, Darren was at my side.

"I have another deal for you. I'll let you fuck me, if and only if, you suck a guy of my choosing."

I was taken aback. It was only Darren I really wanted but could I suck a stranger if it meant I could fuck Darren's smooth white butt. Hell, yes I could.

"Okay, yes, yes, I can but who?

Darren looked over at a booth, where one guy sat alone. He looked about 60, a trifle overweight and balding. He saw me look over and lifted a glass, gesturing for me and Darren to come over to him.

"Howdy guys, my name is Reuben, I'm from Arizona. I believe you two guys will entertain me tonight." He gave a dirty chuckle.

Darren quickly introduced me, "this is Sam and Reuben, you are in for a treat, as Sam has never sucked cock before."

Reuben whooped with delight and added

"Now I won't know where to cum. Your ass Darren or his mouth."

"Let's make a night of it and you can do both." suggested Darren.

Reuben whooped again, he was an obnoxiously loud character but I had no choice if I wanted to take Darren.

They decided to leave straight away and I suggested I follow on ten minutes later. Let them get going. I sat trying to get myself together in readiness for something I did not want to do but it was a means to an end.

"Good evening sir."

I looked up, expecting a waiter. Instead, it was a coloured gentleman, immaculately dressed and about my age.

"My name is Abedi, may I sit down?

"I'm sorry Abedi but you could say I'm taken, at least for tonight."

"That is a shame sir, maybe another night?" He asked, more in hope than expectation.

Again, I could not understand my feelings but I answered him.

"Yes, I would like that and call me Sam." I smiled at him, taking in his chiselled good looks and wondered if what they said about black men was true. I had a feeling I would soon find out.

I then made my way to Reuben's room and opened the unlocked door. Darren was on the bed, face-down, ass-up and the American was pumping his ass hard.

"Hi Sam, I was just getting into the swing of things. Don't worry, there is plenty for you."

At that he pulled his cock from Darren's ass and I saw it for the first time. It was at least eight inches long, cut, with heavy veins on the shaft. I must say, the thought of it frightened me but I did what I had to do.

I quickly stripped and dropped to my knees.

"Right, you worthless cocksucker,

tell me you want it, need it."

"Reuben, I want and need your cock."

"Put some spirit in it, cocksucker."

"Reuben, I desperately need to suck your huge cock and want you to fill my mouth with your cum, please."

"That's better, cocksucker. Now get to it!"

I hated the man but as soon as my lips were around his cock, nothing else mattered. It was still wet from being inside Darren, so I could taste his ass too.

At that moment, it was like a big switch was turned on in my life. I now knew that all these years with Anna I had been in denial. Now I knew that I was destined to suck cock and fuck ass for the rest of my days. It made me forget it was Reuben I was sucking, as my tongue explored his piss-slit.

"You are one dirty, slutty cocksucker!" Roared Reuben, as his cock slammed my throat. I could feel him tense up and suddenly my mouth was awash with his cum. I tried to swalow it all but little drops escaped. Darren was quickly on to me, licking up the escaped drops, until he finally kissed me.

Reuben needed some time to regain his strength and so happly watched as I sucked off Darren. I loved his big tight balls and he loved them being licked and sucked.

"That's enough fun for you two." Reuben bellowed. "My turn to taste his young cock, then I'm going to fill his ass."

I decided to head back to my cabin, my head spinning with the events of the night. My mind harkened back to Abedi and now I wished he was fucking me. I wanked and came over my hand and licked it up, dreaming it was Abedi's cum.

I must have fallen asleep, naked, with my cock in hand, when Darren returned. He woke me by gently licking my cock, which sprang to attention. He then sat astride me, lowering himself onto my hard-again cock. I just lay back and let him do the moving. I looked up at him and his beautiful body and realised, yes, I was gay and I loved it. Waves swept through me, as I was fucking his tight ass and I came like an express-train. Darren's ass milked my cock dry, before he snuggled up beside me.

"I'm enjoying this holiday so far." He whispered.

"Me too but no more Reuben, okay!"

"With you there, he was an arrogant prick but you seemed to enjoy yourself, Sam."

"It's because I now know who I am, a slutty little cocksucker who loves fucking you."

We fell back together and kissed deeply, tenderly, lovingly and my cock grew again. What was I now becoming?

We decided to skip the club the next two nights, mainly to avoid Reuben. The third night, it was quiet, maybe most had hooked-up. Even Reuben was missing. Just as I was thinking of leaving, I heard a familiar voice.

"Sam, is that you?" It queried.

"Abedi! It's great to see you." I genuinely exclaimed.

"Darren meet Abedi, we spoke briefly that night before I went with Reuben."

Darren announced, "It was the day Sam realised he was gay"

"Surely you could have found out easier than that." Abedi chided me.

"Well maybe if you'd turned up earlier, it would have been you." I hoped he believed me.

He laughed. "Well that cherry's been popped now." and he playfully punched my arm.

"No it's not. I only sucked him. I'm still waiting for a man to fuck me."

Abedi looked at me and stated "You want my cock, don't you?"

My heart skipped a beat. "Yes, I want you to take me, make me your bitch."

"Then willingly Sam, I will do it but what about young Darren here?"

Fuck me too, I'm sure you've got enough to go round."

We hurriedly finished our drinks and followed him to his cabin, where he quickly took command.

"Get undressed, I want to see my naked bitches before me."

We quickly did as he ordered and stood with our two cocks to attention.

"Now you will see a real man. Sam, unbutton my shirt."

My hands were shaky but I managed it. His smooth chest was well-maintained and I sucked at his left nipple.

"Undo my belt and pants."

I could see the huge bulge and as I unzipped him, a monster fell out! It had to be at least ten inches long. I was transfixed and so Darren took over. He pulled Abedi's pants fully down, for him to step out of.

"Sam, I know you want him to fuck you but you're not ready yet, at least not for this." Darren licked the length of the ebony shaft and kissed the pink head. He grinned at us both as he said "Guess I'll just have to volunteer then.

"Make him wet Sam, prepare the ground"

I wasn't sure what I was doing but Igot behind Darren and started to lick his ass. He groaned in pleasure and my tongue went further. It felt like his puckering ass was trying to grab my tongue and I loved it. All too soon, Abedi intervened.

"Move over Sam and see what you're missing."

Abedi started to push at the entrance to Darren's hole and Darren moaned as the rod slid into him. I could see there was a mixture of pleasure and pain in his face, as Abedi pumped him relentlessly. Eventually he unleahed his seed into Darren's ass and Darren virtyally collapsed.

"Clean me, bitch." Abedi ordered.

I coaxed the remaining cum from him and savoured it, then licked his cock and balls.

Abedi looked at me and challenged me.

"Maybe next time, eh?"

I kissed his cock again and answered.

"Oh, I do hope so."

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5 Comments
AnonymousAnonymousalmost 2 years ago

Such a Turn Om

AnonymousAnonymousalmost 2 years ago

Great story. I am so hard now, ready to stroke and shoot a big big load and then eat it. Love hot cum in my mouth.

Can't wait for more from you.

AnonymousAnonymousalmost 2 years ago

Thanks for your wonderful story so far! I am closeted, but knew what Friends of Dorothy was, but couldn't

attend as I was cruising with my wife. I am excited to hear of Sam loosing his virginity to the BBC!!! Please don't make us wait!!

ShortyMacShortyMacalmost 2 years ago

Wow that sure made me hard. Thank You for a good story. Mmmmmmm

jonkingbrothersjonkingbrothersalmost 2 years ago

Loved the speed and the intensity of this. It's like a freight train slamming into a tight just-opened hole. This one really made me stroke hard. Thanks for taking us on his journey into sluthood.

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