First Time Fling

For a fifty year old he aged well and soon enough after months of flirting over social media, and skyping, he'd invited me on a date to meet up with each other. I was only twenty one but at his age, Hank had managed to talk his way in to many meets ups with me online that transformed in to meets ups face to face. He was a sly and very charming man who made me realize how much I loved muscle daddies. Him being a biker didn't hurt either. Hank was a smooth talker who knew how to get me riled up, and he'd made me feel good about being in a vulnerable position. It was a relationship I knew was going to end up in bed, over and over again.

We agreed to meet at a public place first, only for caution's sake, but we were very comfortable around one another. We met at a cafe from where I lived and dressed in casual wear just to look like I knew what I was doing. When I arrived at the cafe I was looking for him. There he was, with a square jaw, bald head and great physique. My mind told me to turn back, but I just went for it. I walked over and he smiled noticing me. He asked me to sit-down and after a while I felt comfortable around him. Quickly the tension wore off and we chattered like old friends for hours.

He was divorced and ultimately preferred men to women; he also knew I was experimenting and open to new experiences, but didn't seem anxious to try anything other than the casual flirting. That day was filled with fun experiences including pool, lunch and driving around on his bike with me on the back of it. I knew things were taking a turn for the better when I began hanging on like one of his lovers, holding on for dear life. The bike would take a pause prompting to subtly grab his crotch which he seemed to enjoy. Eventually I just set my hands down on his crotch, leaned against his back, and let the bike take us away.

At twenty I didn't feel right letting myself become vulnerable to a fifty year old I'd just met, but he felt right, and that day after a lot of driving we'd settled at a diner on the coast. I couldn't explain it but he had a way of making me do things by talking his way through to me. Maybe it was because I was young or inexperienced but my hesitation always met no match for his will.

That day during dinner, we'd spent most of the time talking and he'd jokingly suggested that he jerk me off under the table. I'd denied it adamantly, but after twenty minutes of talk, he'd convinced me that it was a daring idea. He leaned over and began caressing my cock under the table. I was uncomfortable at first but then he unzipped my pants and started jerking me off in public. I became so aroused and tilted my head back.

He smiled at the sight of me in pleasure then grabbed my hand and led me to his bike cutting dinner in half and almost storming out of the diner with our cocks hanging out of our pants. We drove to his apartment where he made me feel comfortable around him. We talked and then he leaned forward and kissed me gently on the lips. I was terrified but aroused. Then before I knew it we were making out passionately on his couch, I was swimming in heaven. His tight shirt, goatee, and bald head made me aroused which had never happened to me before.

He kissed my neck and I sighed with pleasure, he undid my shirt and slowly gently kissed my nipples. I stopped him. He looked concerned and asked me what was wrong.

"I never done anything like this before," I said.

"I know. I guessed it by the way you shivered," he said.

"But I wanna keep on," I said. He smiled and kissed me passionately.

I shook in pleasure and grabbed his head. He took off my shirt and took off his revealing his large build. He then undid his clothes getting completely naked. My how he was hung. My jaw dropped to the floor, I was surprised at how turned on I was. My body shook in nervousness, as I looked at his big head. He reached over and undid my pants slowly, my bulge was revealed as he unzipped me. He threw my pants away and started massaging my bulge. I gasped in ecstasy.

"Don't worry," he said, "you'll love this."

I leaned my head back and let him get to work.

Before long I could feel his warm silky mouth wrapped around my decently sized cock. I gasped and jerked my body wildly, as I felt my cum build up. He began caressing my nipples as he went to work and soon I blasted his mouth with loads of cum hard and long. I couldn't believe it. I grunted and screamed as I shot load after load in his mouth. He swallowed it all without hesitation and began waving his huge cock in my face.

He smiled and caressed my face. "Try it. Suck it like a lollipop," he said. I leaned over and slowly explored the cock sliding in and out in my mouth, I clenched my eyes close at first but soon got to like the taste, I started speeding up the pace, He pulled my hair in pleasure as he grunted feeling my tongue circling his head. It was heaven. I started going faster and faster until finally he shot a huge load into my mouth. I swallowed most of it but some of it was spit out. He panted as his dick became soft.

He lay on top of me and we began making out passionately on his couch, we talked a bit, and kissed. I asked him if he's done this with a younger man before and he told me about how he made love to young men in the past, but none quite like me. It made me even more aroused. He suggested we finish this in his room and he led me onto his bed. At first I was reluctant to enter his room, but felt comfortable. I was so turned on. I was his toy. We fell on the bed kissing and he laid me gently on his pillow. I was ready and willing. He became hard again and turned me over gently massaging my body with his soft kisses. I moaned in ecstasy. This was the greatest experience I've ever had.

He started probing my ass softly making my virgin ass ready. I was moaning in pleasure. He then raised my ass gently and started fingering me again. It stung at first but felt really tingly after a while. He took some lube from his drawer, obviously kept there for his usual experiences with men and lubed my asshole. He then mounted me and told me it would hurt at first but go pass the pain. I felt his huge rod enter my virgin hole as he pumped me slowly, it stung like hell but soon felt tingly and hot.

Soon as he gained rhythm pumping me as my asshole adapted to his huge cock, he began pumping me faster and faster. I screamed in pleasure as he grabbed my shoulders and pumped me harder. The bed shook as there was a brief silence where there was only the sound of his balls slapping my ass and his headboard banging against the wall, this made him enraged and he pumped harder and harder making me moan in ecstasy. I lay my head on a pillow and let him fuck me wildly. I grunted in pleasure as he fucked me and jerked me off.

I gasped as I shot all over his sheets; finally he stopped as I could feel him shoot into me wildly. He grunted and fell down with me. We lay there panting and chuckling. This was a great experience, later that night I fell asleep in his arms and stood over night.

The next morning I felt weird, we ate breakfast at his table and talked, but not much. I felt sore and admittedly swimming in a haze of exhaustion and new feelings. That changed though as his skill for talking me in to everything prompted a quick fuck on his table before he went off to work. That night when I got home I fell asleep instantly thinking about my new experiences I'd shared and how much I'd indulged in for a first outing. That weekend my roommate went off on a trip Jeff talked me in to seeing one another again and came over; we made love all day. Towards the night he left and we parted ways.

After that night Jeff and I saw each other again every summer; the experience I had made me realize what I really wanted as my passion for men increased my passion for women as well. Regardless of where my loyalties lay, Hanks always found his way in to my pants, even after I'd married. And he would always be there lying beside me, dominating me as his own every single time.