The Time I Had Sex With An Older Man

The Time I Had Sex With An Older Man

I became more curious about sex with men as I got older and decided I wanted to try it out fully

Image for postPhoto by Nick Karvounis on Unsplash

I?ve always predominantly considered myself straight.

When I was a teenager, I never experimented with boys or men, I was always attracted to women and specifically, older women.

In my 20?s I?d been involved with a few male-female-male threesomes that included some touching and activity between myself and the other guys, but nothing over the top.

By the time I was in my late 20?s, through happenstance, I ended up having a fantastic night of incredible sex with a transwoman.

Not Everything Was As It Seemed

Life presents interesting opportunities sometimes and the excitement comes from taking the leap and stretching your?

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But as I entered my mid-30?s, I started becoming more curious about having sex with a man and what that would be like.

It was weird, I wasn?t physically or even sexually attracted to men specifically, but I was interested in trying it out.

Being Open To Possibilities

In my line of work, I travel internationally a lot and I come into contact with people from all over the world across a wide age range.

When I thought about the possibility of having sex with a man, it was always the same picture in my imagination ? an older, refined gentleman who was fit and well presented.

Again, it wasn?t like I was physically attracted to that type in the same way that I find a mid-40?s blonde, size 16 women with ample breasts attractive, but if I could find someone who fit the description in my mind?s eye, then I would be open to the possibility.

On an extended two week trip overseas to one of our international branches, I was attending a client function where I met Jack.

Jack was in his late-60?s and was a very senior executive at a banking customer of ours. In talking to him over the course of the evening, it was clear that he was probably gay and that intrigued me because he matched very closely to what I?d always envisioned as the type of man I?d like to bed if I were to ever go down that road.

During the evening, we hit it off on a personal level. We spent most of the evening sharing anecdotes about travelling to far-flung places and laughing at the various situations we?d found ourselves in during those trips.

When I got back to my hotel room that evening, I connected with Jack on LinkedIn because, despite everything else, he was a good person to know professionally.

I woke up the next morning a bit later than usual and I had a notification on my phone from LinkedIn that Jack had accepted my connection request. I immediately sent him a note thanking him for accepting my connection request and telling him how nice it was to meet him.

Within the hour, Jack had replied to me on LinkedIn saying that he enjoyed our conversation the night before and as he knew I was in town for another week or so, he invited me to a function that evening that he was putting on for a few friends and some business associates.

I, of course, accepted and told him I was looking forward to it.

Later that evening, we spoke briefly as I arrived and Jack told me to stick around so we could catch up, but as he was the host he needed to mingle.

I spent the evening talking to a few people, but really, I?m not entirely comfortable in large social gatherings making meaningless small talk with strangers.

I was considering taking my leave when Jack made his way over to me and apologized for stranding me for much of the evening.

We talked about work, politics and several other topics as people drifted in and out of our conversation.

As the night was winding down, Jack asked me if I had plans for the weekend and if not, would I like to have lunch on Saturday on his boat.

I hastily accepted his invitation and he smiled saying, ?It?s a date!?

Just Riding The Waves

Jack sent me the name of his marina and some simple instructions to find where his boat was moored.

The boat was not at all what I expected.

I had been anticipating a 30′ cabin cruiser or something like that, but Jack?s boat was a full 60′ motor yacht.

In my line of work, I was familiar with boat sizes and types because many of the people I associated with professionally bought them as status symbols ? personally, I?m not a huge fan of boats, but a basic knowledge has helped me in casual conversation with the right people over the years.

I knew that Jack?s boat, brand new, was probably in the US$1.5m range depending on how well it was appointed internally.

?Wow, Jack! When you said we were having lunch on your boat, I wasn?t expecting this. Permission to come aboard, Captain!?

He laughed as he knew I was having fun with him, but I could sense that he also knew that I was impressed.

As soon as I was on board, we went to bridge and Jack offered me a seat in the co-pilot?s chair as we pulled out of the marina and made our way out of the harbor into some open sea.

After about twenty minutes heading south, we found a nice spot to drop anchor and have lunch that still had visibility to land as I wasn?t totally comfortable being out in the deeper water.

Jack showed me around the boat and it was massive ? it had three bedrooms, two bathrooms, a full kitchen, a formal dining area and three different outdoor decks.

He suggested we take lunch on the forward deck?s dinette area where he?d set up a covered area for us.

I sat down and he brought out from the kitchen a massive spread of cold cuts and catered finger foods for lunch.

We sat for talking, eating and bobbing slightly with the gentle waves ? this was how the better half lived.

Lunch Was Just The Appetizer

Jack was very open about his life as I asked him questions.

He had been married for 32 years, had three grown children and he had five grandchildren. His wife had passed away from cancer about five years ago and he?d been single since with very few relationships.

While he?d been married happily, he said that about 20 years into his marriage, he realized that he was gay.

A couple of years after coming to that realization, he told his wife and they decided to stay together, but that if he wanted to have discreet relationships that she was fine with it.

He said during the time he maybe had two or three lovers, but with work and his devotion to his wife, he really didn?t feel the urge to go further.

After her passing, he said he explored his sexuality a bit more, but he found the ?gay scene? not to his liking so while he?d had the occasional short term relationship, he didn?t feel that he needed another partner.

It was interesting listening to this classy, warm man share his life story and the struggle he had in dealing with his sexuality.

Jack popped up to get himself another glass of wine and to refill my sparkling water and I stared over the edge of the boat at the sandy beach a few hundred yards away.

As Jack sat back down and passed me my water, his hand landed midway up my thigh.

I noticed it, but it was so casual that I wasn?t sure if it was an advance or just a friendly gesture.

Our conversation continued as he asked me more about my background and how I?d ended up escaping relative poverty as a child to become as successful as I was at a young age.

As we talked, I noticed his hand, ever so slightly, making its way up my thigh ? he would take it off to get a drink and return it slightly higher up, or he?d tell me something and squeeze my thigh, inching upward all the time.

Finally, his hand was on my upper inner thigh and it was unavoidable for us to ignore the fact that his fingers were brushing against the slightly growing bulge in my shorts.

He leaned in to kiss me and I returned the kiss.

Going Below into the Aft Decks

I?d never kissed a man passionately before, it felt unusual and exciting.

After kissing softly for a while on the forward deck, Jack led me downstairs to the main cabin below where we got undressed and slid into the softest cotton sheets I?d ever encountered.

We went back to kissing and I had a raging hard-on by this stage. As we continued our embrace, I could feel his hard cock pressing into me as well.

Slowly, Jack broke away from our kiss and began making his way down my neck and chest, feathering me with light sucking and kisses as he slid down my body.

My back arched slightly as Jack took my cock into his mouth.

It felt amazing as he slowly sucked me and took the full length of my cock into his mouth ? I could feel the tip touching the back of his throat as he deep throated me.

Jack broke away from my cock to lick and suck my balls. He switched between tonguing my perineum and taking each of my balls into his mouth softly in turn.

I was in ecstasy with Jack sucking my cock and balls.

As I laid there enjoying his mouth work, I realized that I needed to figure out how far I wanted to take this. I was now at the extent of my gay sex experience and needed to make up my mind about what my limits were.

With Jack sucking and licking the full length of my cock, I decided that I needed to just take this opportunity and go for it.

I moved slightly onto my side so as to pull my cock away from his mouth and he made his way back up the bed, obviously surprised that I stopped him before I finished.

As Jack moved up towards the head of the bed, I took the plunge and started making my way down, kissing his chest and his stomach before taking the plunge and wrapping my mouth around his cock.

Breaking New Ground

I wasn?t sure what to expect with sucking a cock, but I figured I would just go for it with gusto and enthusiasm.

I sucked Jack?s cock for several minutes allowing copious amounts of my spit to run down over his balls and into his ass crack.

My tongue began sweeping over his balls and his taint.

I turned him onto his side and dove in to start licking out his asshole.

As my tongue probed and circled Jack?s anus he groaned and sighed deeply ? I could hear him moaning, ?Oh fuck!? as I licked his ass.

I made sure the area was covered in my saliva, turned him back onto his back and slid my middle finger gently into his ass.

Jack cried out in a mix of pleasure and discomfort as my middle finger probed deeper into his ass.

I went back to sucking his cock while I fingered his asshole, rubbing firmly against his walnut-sized prostate.

It took less than two minutes before I felt the inside of Jack?s ass start to tremor and then his cock pulsed as he filled my mouth with his cum.

Groans of delight were coming out of Jack as his ass squeezed my finger and I sucked every drop of semen out of his cock.

The salty, slightly bitter taste of his cum was almost tangy and I was surprised at how I had reflexively just started to swallow it as it entered my mouth.

As his orgasm subsided, I released his now softening cock from my mouth and slid my finger gently out of his ass.

Jack looked down the bed at me, still between his legs and said, ?Fuck me.?

Finding New Ways To Deliver Pleasure

I stood up from the end of the bed, Jack reached into the nightstand beside the bed pulling out a bottle of lube and made his way to the edge of the bed, laying on his back.

I took the lube, covered my cock in it and slid my lubed up fingers inside his ass to get him ready.

And then I stood between his legs, slid him down towards me and gently guided my cock slowly and deeply into his ass.

I had stayed rock hard while sucking his cock, so I was primed to fuck him.

My rhythm started off very slowly at first while Jack?s ass grew accustomed to the fullness of my cock inside of him.

But I was so horny that as soon as I could see Jack was comfortable, I began to go harder and faster.

I needed to unload inside of him. I?d been desperate to fill his ass with my cum from the moment his hand touched my thigh up on deck.

In very short order, I felt the waves of orgasm overcome me and I thrust my cock deep as I came inside Jack?s ass.

I pumped his ass with short, sharp thrusts to give him all of my seed.

As my orgasm passed, my head was swimming and I felt a bit dizzy, so I fell back onto the bed after pulling out of him and we just laid there quietly for a few minutes catching our breath.

When I?d composed myself we had some of that post-sex, meaningless pillow talk where we complimented each other on how great we?d been.

Jack rolled over into me and began biting at my ear and kissing my neck which felt incredibly nice. I noticed that his cock was rubbing against my leg as he kissed me and that it was semi-hard again.

Without thinking, I moved down and took his semi-erect cock into my mouth again.

Almost immediately, Jack became fully erect.

I was fixated on sucking his cock vigorously and trying to make him cum in my mouth again ? I wanted to feel his salty cum hitting the back of my throat.

To me surprise, Jack stopped me, repositioned me to lay on my stomach and went down to lick my asshole.

I love being rimmed and Jack was expertly flicking my anus and probing it slightly with his tongue to the point where I lost all sense of where I was.

The next thing I realized, I felt the coldness of lube running between my ass cheeks and then Jack slid his finger into my ass.

I sighed deeply with pleasure.

I had many women over the years penetrate my ass with their fingers and I?d regularly seen a particular erotic masseuse for over a decade that would give me multiple prostate orgasms, so this was something I was accustomed to.

But I?d never had a man finger my ass before.

Within seconds Jack was rubbing against my prostate which initially feels like a slightly uncomfortable pressure, but before long turns to a pleasurable sensation.

I?d moved to a doggy style position to give him better access to finger my ass and Jack was also gently caressing my balls with his other hand.

I was in ecstasy.

Then I felt his finger slide out and pressure against the opening to my ass.

Jack was trying to fuck me.

Going All The Way

I?d never bottomed before and my eyes opened wide as I realized what was happening.

I could feel the tip of his cock pressing slightly into my anus and I knew I had the choice ? stop now or go for it.

With my eyes closed, I pushed out with my diaphragm, took a deep breath, and pressed my ass back against his cock to help him enter me.

There was an immediate uncomfortable pressure inside my ass as it stretched to take his cock.

I let out a loud groan involuntarily and Jack told me to just relax.

Within a few seconds, the discomfort passed and I pressed back more against Jack to bring more of his cock inside me.

He said, ?Oh, that?s nice.?

I turned my head back slightly and told him that I?d never done this before.

He said he?d go slow.

Between him pressing forward and me moving back, I could feel the base of Jack?s pubic area pressing against my ass?

Jack?s entire cock was all the way inside me.

Slowly and gently, Jack began to fuck me.

His control was exceptional. Every time he would pull out a bit and slide back in, the head of his cock would rub against my prostate.

There was some discomfort, but the pleasure of having my prostate rubbed overtook that in a minute or two and I began to increase Jack?s pace.

He just slowly and methodically fucked my ass.

After about ten minutes, I began having an intense prostate orgasm.

I reached down and could feel my cock leaking, but I wasn?t ejaculating ? it was a dry, prostate orgasm.

Wave after wave of ecstasy that comes from having a prostate orgasm overcame me. I was now drooling and groaning with pleasure.

Jack didn?t stop fucking me ? slowly and deeply.

My prostate orgasm subsided and a few minutes later it returned, deeper and more intense.

I was gasping for air from the intensity of the orgasm when I heard Jack say he was going to cum.

Then I felt him plunge harder into me and his cock twitching inside my ass.

My head leaned back at the sensation of his hot cum spreading inside my ass, it was an odd and pleasurable feeling, but it was the idea of him cumming inside me that was the best part.

I collapsed on the bed and Jack laid beside me.

Constant State of Arousal

I rolled over onto my back and took some deep breaths as I relaxed.

Jack said to me, ?I didn?t realize that you?d never been fucked before. Had I known, I would have asked you if it was ok before I started trying to enter you, but it seemed like this wasn?t your first rodeo.?

We laughed and I assured him that it was great. I told him that I?d never experienced anything like feeling him cum inside my ass before.

As I was telling him how I felt, I noticed that I was rubbing my now semi-erect cock without even thinking about it? it was slick from the precum that continued to dribble out.

Jack noticed, so took over stroking my cock and began sucking my nipples.

Almost immediately, I was fully erect. Jack squirted some lube onto my cock, climbed on top of me and slid my cock into his ass.

It felt incredible. He rode my cock hard and fast as I laid there soaking it all in.

I had no sense of time by this point and eventually, I could feel my orgasm building.

My hands grabbed Jack?s hips and pulled him down hard onto my cock as I thrust upwards.

I unleashed a massive load of cum inside Jack?s ass.

The orgasm I had was incredibly deep and guttural in nature. This was nothing but raw sex ? fucking to get that intense sexual release.

After having a prostate orgasm your ejaculate is extra voluminous and Jack?s ass was taking every drop of it because I wasn?t letting go until I was done.

He would sigh as I pumped more semen into him and my orgasm rolled onwards.

Finally, I was spent and let go of his hips.

He sat on top of me for thirty seconds, my cock still inside of him but neither of us spoke, we were both exhausted.

Waking Up to a New Reality of Who I Now Was

We laid there in the dimly lit cabin surrounded by the calm sound of the ocean and I fell off to sleep.

I woke up to Jack rubbing my chest. He was dressed and had a glass of water for me along with a small fruit plate on the nightstand next to the bed.

He told me that I?d been asleep for over an hour, that he?d had time to have a shower and bring me some snacks.

My body was simultaneously relaxed in that way you get after you?ve had tremendous sex, but also sore from the vigorous activity. In my case, my ass was a bit sorer than I was used to, but that only stood to reason.

?Do you want to have a quick shower? I saved you some hot water, but it?s going to be dark in an hour and it?s probably safer if we head back to the marina.?

I stood in the small, but luxurious shower in the ensuite of the main cabin and just allowed the warm water to run over me.

I?d wanted this and I knew that when Jack invited me onto his boat and I had agreed to spend the day with him that this outcome was a very likely possibility. That said, I was still somewhat in disbelief about what had happened.

I had full gay sex with a man and enjoyed every second of it.

Later that night when I got back to my hotel and laid alone in bed, staring at the ceiling, I continued to think about what had happened and what that meant for me.

Was I gay? Was I bisexual? What did this mean?

I came to the realization that it didn?t matter. I didn?t need to label myself or be a part of any group.

I was me. I had tried something new, I?d enjoyed it, and I learned something about myself in the process.

As I drifted off to sleep, I felt content that this experience had made me a more well rounded and emotionally complete person.

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