My real first time was on a cruise ship. In between semesters I managed to snag a summer gig as a waiter on a cruise ship.
“Anything else you need ma’m,” was my standard response after serving the latest meal. Auto-pilot. All day long because eating is all you do there.
Sometimes there’d be a piano player and in the evening he’d give a concert every other day.. He was in his 50s and since we bumped into each other all the time we did the proverbial “hi” and “are the guests drivings you nuts” kinda thing
So anyway, one evening after dinner clean up, he finished his gig and we got to talking with others at the bar. Then they left and it was just me and him. We chatted a bit and then he asked if I wanted to come to his room for a drink. I thought it was odd since we were already drinking here but I thought what the heck, let’s see what kind of privileges he gets compared to me stuck in a bunkbed with others. I told him to give me a few minutes to change and I’d be over.
But then back at my room I wondered what this was. Was this a date? Or what? I had fooled around with a few guys before, making out, oral, mutual jacking off but nothing more. But I did have my fantasies. I mean even though he was older he was good looking enough. It felt enticing to have an older man guide me. I’ve fantasized about it before. So I changed and made my way to his room where he opened the door and let me in. Sure enough he had his own place, even with a view of the ocean.
He had a bottle of wine ready and so we sat on his couch and chatting the way we were earlier. We talked about our life paths, his extensive one and my hardly anything yet. It was pretty friendly and I felt comfortable with him and noticed a growing attraction.
“How do you do these cruises,” I asked. “No family anywhere?”
He smiled. “You mean wife and kids at home. No I wasn’t selected for that team this time.”
It was obvious what it implied. So he was gay I thought. That made this more interesting.
“What about you,” he asked. “Girlfriend back home?”
“Well no. I’m not selected for that team either. I have met a few guys but it never went far, a few dates, some fooling around, nothing more.”
“It is hit or miss,” he said.
We looked at each other. It was kind of obvious we were feeling closer to each other and then he reached for my hand. We played with our fingers.
“You know I’ve noticed you awhile.”
“Really?”
“Mmhm.”
“Gaydar kinda of thing?”
He laughed. “I guess you could say that.”
“So you top, bottom, vers?”
“‘I’ve always liked to top my lover. What about you?”
“Well when I think about it, I think I’m bottom though it’s never gone that far before. It’s what I fantasize about.”
We looked at each other and felt our growing closeness. Then he put his arm around my shoulders and came to me. Our lips touched and we started kissing softly, our tongues slowly tasting each other. I immediately got aroused and soon we settled into making out on his couch. He kissed with passion, like an expert lover with lots of experience that he undoubtedly had. And then he reached for my crotch and squeezed me lightly. I moaned softly and reached for his crotch and felt his erection through his pants.
“You’re so excited,” he said.
“I guess,” I said.
Then he kissed me and said, “Come baby, let’s take a shower.” We went to his bathroom and got nude together and got into the shower with our erections. We lathered up and all that and rinsed and then he took me in his arms and we kissed again. It was so sensuous and hot. He turned me around and held me from behind and reached around to fondle my balls as he kissed my shoulders and neck. His throbbing 7” inch cock slid along my slit. Then he cupped my small tits.
“You have nice tits Sandy.”
“You like it baby?”
“O yes, I can feel you’re so sensuous.
“I am.”
And then I slowly bent over to give him more access.
“O yes baby,” he said and slid his cock along my slit, up and down. It was such a tease. Was he going to put it into me right now? I would have welcomed it. Maybe he would lube himself with soap and take my virginity. Finally I could feel a man drive into me. But then he stopped and stepped out and grabbed a towel for me. We dried off and then he took my hand and led me to his bed.
We got up and kneeled before each other. He held me again and I put my arms around his neck and we resumed making out. Now it was even more sensuous, us naked together, starting our love night. We kissed and kissed before laying down and I immediately went down and licked his balls. I love balls and suckling them while looking up at his pleasure filled face. It makes me even hotter to see him like my beginning skills. I made love to his shaft with my lips and tongue. Kissed it over and over and licked my way to his cockhead. He was already dripping precum. I smiled up at him and eagerly licked his cockhead clean before taking him into my mouth. My head went up and down his large cock, hoping to take more of him in. I had seen videos of guys taking a large cock completely into their mouths and wanted to be like them. I tried but gagged but I was getting better at it.
He sighed “O Sandy that feels so good.” I was getting him harder and more aroused before he took charge and we got into the 69. It was heaven and we stayed there awhile. His finger slid between my asscheeks and pushed at my hole. I moaned with his cock in my mouth.
Then turned around and laid on top of me, spreading my legs. We made slow love. Moaning together. Kissing. Cooing. “I kept moaning o my darling.” More kissing. We loved kissing each other.
And then he moaned “O Sandy. I want to be at one with you.”
“Please baby,” I said into his ear. “Take my virgnity. “
I raised my legs and pulled them back and exposed my hole to him. I was in heat. He got some lube from his drawer and lubed himself up. Then he came to my hole. I looked up at him as he started pushing. I welcomed him. It was pushing me into more heat. He pushed and pushed and it started to sting as he stretched me. I loved it. I wanted more. He pushed more and I relaxed more. Then his cockhead pushed through, streching me and slowly entering.
“OOOOOOOO”
He moaned softly, adjusting his thrust to what I could take. He slid in more and I was going into ecstasy.
“OOOOO baby,” I moaned. “OOOOO baby.”
Slowly he slid in even more, a third of his thickness pushing deeper. I moaned and moaned and then he laid down on me and cradled me. He held me firm, pushing his cock deeper into me.
“OOOOO darling,” I moaned. “Do me. Make me yours.”
“OOOO Sandy this is amazing. You’re so tight. I’m almost there.”
I lifted my legs a tiny bit more and he pushed all the way in, all 7” deep in me. We laid still a bit adjusting to our union. Then we started kissing again, just laying still and kissing. It was amazing to feel him inside me, in complete abandon to his cock. I just moaned and moaned.
“I love you inside me,” I said and looked up at him. We kissed more but we could sense our passion growing. We wanted more. And then his first slow pump.
“MMM” I moaned. “Yes”
And then he slowly slid back and then returned back in letting me know he’s taking me. He knew how to break me in. Slow, very slow, then faster deep, pushing all the way in.
“Please baby,” I moaned. “Do me. I want to be your bottom.”
“O yes Sandy I hope you’ll be my bottom for the rest of the trip.”
“Yes baby. I’m yours. I think I need this everyday.”
“Oh yes Sandy,” he moaned. And then he started pumping me faster. And faster.
“O yes” I whispered. “Pump me.”
And he did. Slowly, strongly, then faster, then slow again. But then I could feel his passion rising. He moaned more and it felt like his cockhead grew an inch inside me. Faster and faster he started
“O yes honey. O please. Cum in me. Pump your cum. Please.”
And then he moaned and jerked and pulsed 8-10 streams of his sperm into me. It was absolutely amazing to feel him throbbing and emitting into me. When he finished emptying into me we kissed for a bit. Slowly his seed ooozed out of me. I reached down and scooped some of his oozing cum on my finger. I brought it to my face and looked up at him and opened my mouth. My tongue licked my finger and took his cum into my mouth. Then he took my cock in his mouth. O my I moaned. I tasted his cum and swallowed it and felt myselt going over the edge and spurted me semen into his mouth. He swallowed it too and then we got closer and kissed again, sharing our cum.
The next day I could still feel him inside. Someone had obviously penetrated me. And I wanted more. We bumped into each other in the middle of the day and hid around the corner where no one could see us. He actually apologized to me for going so fast.
"I just go so excited being with you. I just wanted to be inside you."
"You didn't see me complain? Right?"
"I really like taking my time, exploring each other."
"I'd like that I said." I kissed him. "We'll make slow love all night long."
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