Weekend boat trip with Rick and Alan
It all started the week before. Rick and I were cuddling on his big sectional after a long, slow session when he got that playful, mischievous look in his eyes.
“Baby… I’ve been thinking about something,” he said softly, his big hand sliding up my thigh. “You remember me telling you about my friend Alan? We’ve known each other for years and we have very similar tastes. He’s seen a few pictures of you… and he thinks you’re absolutely stunning.” Rick paused, studying my face. “Would you ever consider letting both of us play with you? No pressure at all. Just something I think could be really special and hot if you were into it.”
My heart started hammering in my chest. The idea scared me — being with a man I barely knew — but it also made my cock twitch hard. I hid my burning face against Rick’s hairy chest for a moment, then whispered shyly, “I… I think I might want to try that. As long as you’re there with me. I want to be good for you… and maybe for him too.”
Rick kissed the top of my head and held me tighter. “That’s my good boy. We’ll take it nice and slow. I promise you’ll feel safe.”
I met Alan briefly a few days later for drinks at a bar. He was tall (about 6’0”), fit at around 185 pounds, with a nice dark tan and a calm, confident energy. He was really sweet and flirty without being overwhelming. By the end of the night I was blushing every time he smiled at me. Rick could tell I was interested.
Friday – Spa Day & Night with Rick
Rick told me he had a big surprise for the weekend and that I should come over Friday night and be ready early Saturday morning. On Friday he revealed part of it: a full day pass at a luxury spa. Five incredible hours of pampering — deep tissue massages that left me melting, a long scented bath, and then the most thorough full-body waxing I’ve ever had. Those Brazilian women were professional but very thorough. They waxed me from my nipples all the way down, everywhere. When they asked if my “girlfriend” liked smooth boys, I just blushed bright red and said yes. If only they knew I was getting prepped for two men.
I arrived at Rick’s house that evening still glowing and super sensitive. He had the soft blue baby doll gown waiting. The moment the silky fabric slid over my freshly waxed skin I let out a little shiver of pleasure.
We were supposed to just cuddle that night so I’d be fresh for whatever he had planned. That plan lasted maybe twenty minutes.
I ended up on my knees between his legs, looking up at him with big nervous eyes.
“Can I… give you a girlfriend blowjob?” I asked shyly.
Rick groaned. “Fuck yes, baby. Show Daddy how much you want it.”
I took my time, keeping my lips sealed nice and tight around him the whole time, swirling my tongue and looking up at him. When he finally came I swallowed every drop without spilling any, feeling proud and submissive.
“Mmm, such a good girl,” Rick praised, stroking my hair. “You make Daddy so happy.”
Later, around 2 a.m., he couldn’t hold back anymore. He pulled me into spoon position, kissed the back of my neck, and slowly pushed inside me.
“Oh god, Rick…” I gasped, feeling that familiar stretch and fullness. “You feel so good… I love when you’re inside me like this.”
He held me close, thrusting slow and deep. “You feel perfect, baby. So warm and tight. I could stay here forever.”
I pushed back against him, whimpering softly. “Please cum inside me, Daddy. I want to feel it.”
When he finally unloaded deep inside me we fell asleep like that — his strong arms wrapped around my small body, his cock still buried in me. I felt so safe, so owned, so loved.
Saturday – The Boat Surprise
Saturday morning Rick told me to pack a small overnight bag. When we got in the car he grinned and said, “Part of your surprise is a boat trip with Alan.” My stomach did a nervous little flip. I knew we were seeing Alan this weekend, but I had no idea it would be on the water.
Alan’s boat was stunning — a sleek 45-foot cabin cruiser with a large open party deck, multiple comfortable benches, and a big round swivel ottoman toward the back that looked perfect for… other things. Down below was a nice cabin with a bedroom and bathroom. It felt luxurious cruising through the calm Florida bay.
As soon as we were out on the water, Rick and Alan sat me down between them on the deck.
“We got you something special, princess,” Rick said, pulling out a small velvet pouch. He showed me the cutest clear butt plug with a sparkling red heart jewel on the base.
“This is the Ruby Cork,” Alan added with a warm smile. “It’s going to keep you ready and keep everything inside you all day. No condoms today, baby. Every single load stays right where it belongs.”
I blushed furiously. “You… you both want that?”
Rick kissed my temple. “Only if you want it too, baby. We’ll take care of you.”
I nodded shyly. “I want it. I want to be full for you both.”
I changed into a blue lingerie set, one of the many clothing sets that Rick brought with him — blue thigh-high stockings, garter belt, the tight corset top that gave me nice hips, and the choker. When I stepped out onto the sunny deck, both men went quiet.
“Fuck… look at him,” Alan said softly, eyes wide.
Rick’s voice was thick with lust. “Our perfect little princess. Come here, baby.”
Alan took me into the cabin first. I was nervous being with a different man, but I wanted it so badly.
“You nervous, sweetheart?” Alan asked gently as he used plenty of gun oil to finger me open.
“A little…” I admitted, voice shaky. “But I want you to have me. Please fuck me, Alan. I want to be good for you too.”
He groaned and pushed inside me slowly. “God, you feel incredible. So tight and smooth. That’s it… just relax for me, princess. You’re doing so well.”
I moaned loudly, gripping the sheets. “It feels so good… you’re so deep. Please don’t stop. I want you to cum inside me.”
Alan fucked me steadily, whispering praises. “Such a good boy letting me inside you. You’re gonna make me cum so hard, baby.”
When he finally unloaded deep inside me, he immediately pushed the Ruby Cork in. “Good boy. Keep Daddy Alan’s load right where it belongs.”
I walked back out onto the deck plugged and full, wearing nothing but the lingerie. Rick was waiting, rock hard.
“Come here, princess,” he growled, pulling me in for a deep kiss. Within minutes I was on my knees sucking him in the bright sunlight.
“Mmm, that’s my good boy,” Rick moaned. “Suck Daddy’s cock nice and pretty for me.”
Then he bent me over the bench, pulled out the plug, and slid inside me.
“Oh god, Rick…” I gasped, feeling that familiar stretch. “You feel so good… I love having you inside me after Alan.”
“Take it, baby,” he growled, thrusting harder. “This tight little pussy belongs to both of us today.”
The whole day became a dreamy, filthy blur. They took turns on the open deck in bright sunlight. When another boat anchored nearby and started watching with binoculars, we all got a thrill from it. They spit-roasted me right there — Rick fucking me hard from behind while I sucked Alan.
“Fuck, look at our good boy,” Alan groaned, feeding me his cock. “You still a little nervous with both of us, princess?”
I I blushed as my mouth was full of his dick, eyes watering before I pulled my lips off of it to talk. “A little… but I want it. Please use me. I want to make both of you feel good.”
Rick thrust deep. “Our little show-off. You like being watched while we fuck you, don’t you baby?”
“Yes…” I moaned. “I want to be good for both of you.”
I got so lost in the moment that I didn’t even think about it when they started going ass-to-mouth. Every time I sucked either Rick or Alan, it mostly just tasted like cum. I was so deep in that eager, submissive headspace that I just kept going, wanting to please them completely.
Later I changed into black thigh-highs, tiny pleated plaid skirt, but kept on the blue lingerie top, and choker. They filmed the sunset scene on the swivel ottoman.
They had me on my back, legs held wide open.
“Look at that pretty hole,” Alan said as he pushed inside me. “Still a little nervous, baby?”
I giggle a little before breaking into a whimper as Alan pushed inside me, I scanned my eyes back-and-forth to look at them both “ I’m not nervous at all anymore .. I wanna be good for both of you daddies” I whimpered, blushing. “ I love it. Please fuck me harder, Alan. I want you to cum inside me again.”. before I stopped talking as Rick’s thick dick slipped between my lips.
Rick held the camera. “Smile for the video, princess. Show us how much you love cock.”, later when I watch the video you could tell that I was smiling, even with a mouthful of cock.
Alan groaned, “I’m gonna cum.”
The camera zoomed in tight as he slammed deep and unloaded. When he pulled out, a flood of cum leaked from my red, gaping hole. He pushed it back in with his fingers before sealing me again with the Ruby Cork.
Rick moved the camera to my face. “How do you like it, baby?”
“Oh… god…” I mumbled, completely dazed and lost.
“Did you cum baby?”
“Twice…” I whispered, voice hoarse. “i’ve never felt anything like that.. I feel like I’ve been quivering for five minutes”
Late that night, after the sunset video and hours of being used on deck, we finally went down into the cabin. I was exhausted but still buzzing, my body humming from everything that had happened. Rick and Alan guided me gently onto the bed. I was still wearing the tiny pleated skirt and black thigh-highs, the blue lingerie top pushed up, the Ruby Cork still snug inside me.
“You’ve been such a good princess all day,” Rick murmured, kissing my neck. “But we’re not quite done with you yet, baby.”
Alan smiled softly, running his hands over my smooth thighs, and commenting, how red and puffy my hole was. “ How are you feeling, baby? Are you ready to be fucked to bed”
I giggled a little like I was admitting a secret, “ To be honest, I’m a little sore.. You guys fucked the hell out of me” I admitted shyly, my voice small, “but I want both of you to have me before we sleep… Please daddies.”
They took turns at first, then together. Rick slid into me slowly while I sucked Alan, then they switched. I felt so small between their bigger bodies, completely surrounded. Every thrust made me whimper and moan.
“Oh god… you both feel so good,” I gasped, my voice shaky. “I love being full of you… please cum inside me daddy.. i want it again. I want to fall asleep full.”
Alan groaned as he fucked me harder. “You’re such a sweet boy. You really want both our loads one more time?”
“Yes… please,” I begged, blushing but eager. “I want to be your good cum princess tonight.”
Rick kissed me deeply while Alan came inside me first, then Rick took his place, thrusting slow and possessive until he added his final load. They kept the Ruby Cork out for a few minutes so they could watch their cum leak from my red, puffy hole, then gently pushed it back in, sealing everything inside me.
“That’s where it belongs,” Rick whispered, pulling me between them in the bed. Alan spooned me from behind, his hand resting on my plugged ass, while Rick held me from the front. I fell asleep sandwiched between them, feeling so full, so used, and so incredibly wanted.
Sunday morning I woke up still plugged and full. Rick and I had one more intimate round in the cabinas Alan drove the boat in. face-to-face missionary, making out. and again, taking his cum deep inside me.
it was wild getting off the boat at the marina, it was pretty crowded and I was only imagining how none of these people knew anything we did.
I got home wrecked but glowing. I went from a nervous, closeted boy to letting two men turn me into their dressed-up, cum-filled, plugged little princess on a boat in broad daylight — filmed, watched, and used over and over. And I loved every single second of it.
Rick and Alan made me feel like the most desired boy in the world. I can’t wait to do it again.
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