My experiences with older

[gumshoe]

When my first bf and I broke up, I was 23 and used this time to take advantage of the fact that I was single and gay for the first time as my bf and I met before I was out. It didn't take long for me to start to want to experiment with a new idea that had started to come to me to fool around with older men.

I wasn't normally attracted to older men but liked the idea that they could be attracted to me. I started to talk to older guys on squirt around 24 or so. These stories I'll post here are some of my times. They're definitely not as juicy as some of the ones I've seen that make me jealous and horny to read about but for my own experiences, they're memorable.



My first experience with a significantly older-than-myself guy was with one that was about 43, I believe. We chatted for a few days online. He only lived a few blocks from myself at the time so the possibility of actually meeting up with him always got me hard. Of course, I always chickened out but he was very understanding and made it clear to me that if I wanted to meet up, the focus would be on me enjoying it.

So one evening I decided to say to myself, what do I have to lose?! And he gave me his address and I headed over.

I was extremely nervous, as I normally was whenever hooking up online, but this was different.

I got to his building and he buzzed me in. I took the stairs to his apartment on the 4th floor, went to his door and tried the knob. As requested, it was unlocked and I walked in. He was standing waiting for me in his small kitchen wearing a plain white t-shirt and a pair of navy blue pajama pants. His apartment was very small, nearly a bachelor with one room served as a living room, one equal-sized room as his bedroom and a small kitchen by the main door. He introduced himself and invited me in to his living room. He sat on his couch and I stood by the doorframe.

His voice was very deep and oozed of sex. I imagine the sound of what his moan would be like might be enough to make any guy hard and leak pre-cum.

We chatted for a few minutes, mostly him seeing how shy and nervous I was and reassuring me that it was my choice whether to go ahead and invited me to simply stay and chat or leave if I was uncomfortable. It was awkward but I was also horny and already here so I said "no, I'll stay. It'll be fun."

We went into his bedroom and sat on his bed. Previously, online, we talked about what it was I was into and I told him that I fantasized about being stripped naked by an older man, being the only one naked and sucked. Like a doctor's office scenario, perhaps. He unbuttoned my shirt and slowly revealed by chest and belly, lightly touching me as he smoothed his hands to my shoulders and removed my shirt. A few times he kissed my chest and nipples gently while releasing light moans in between the slurp of his tongue.

His hand then slowly glided toward my jeans where he touched my thigh and made its way up to my button, grazing over my obvious bulge, and he undid the button and upzipped my pants. I lid on my back and raised my legs as he pulled my jeans out from under me leaving me only in my american eagle briefs.

He told me I looked very nice and I replied with a nervous grin as his hands caressed the bulge underneath my briefs. After a few minutes and after being sure I was still okay with it, he pulled off my briefs leaving me fully naked for his visual pleasure. I stood up. By this time I was so turned on, my dick was standing ready for him to put his eager mouth on it. I wanted him to take a few seconds and look me over. He looked up and down and let out an "mmmm" with his deep, masculine voice.

I quietly asked if I could see his and he said "sure" so I sat on his bed while he stood in front of me and put my hand in the draw-string of his pajama pants and pulled down the front, revealing a nice dark dick. A little smaller than my thick 6 and a half inch cut penis but still very nice. I stroked it a few times and looked up at him and smiled before putting it back in his pajamas.

From here, I laid back and he started to caress me again. Kissing my chest and stomach before making his way to my cock. He started to lick before putting the entire thing in his mouth, stroking with his hand but making it as wet as he could while licking and sucking. I didn't need any lube after this as he increased the speed in which his head went up and down. I let out a very pleasurable moan while he moaned with me. Soon after, I exploded in his mouth. It had been a few days and I'm sure it was a lot but not a drop was left over. Once I was finished, he sat down next to me while I sat for a few minutes still naked. He asked if I had fun and I responded with a positive "yeah! it was great!"

Then I got dressed, said thanks and left.


At this point, I can honestly say that this was the best blowjob I had ever gotten. Thinking back, I felt bad that I didn't reciprocate in any way because he was extremely nice but was also very understanding of what it was I was into so he knew that he would most likely not get anything in return. We chatted a few times after that but he also mentioned that he would be moving at the end of the month so I didn't get to see him again.
But he helped open me up to a whole new world of possibilities!

 

[eryk-v]

that was a pretty hot story. I really like reading about younger/older experiences. I look forward to the rest!

 

[didi122]

I was waiting for you to service him while I read this!
How did he look? Did he have bear characteristic? was he hairy? buff?
Good story

 

[gumshoe]

Thanks guys!

That was the first time I ever wrote something in as much detail so I did leave out important details.

He was pretty in-shape. I wouldn't call him buff or muscular but he wasn't too thin and didn't have a belly. I think from what I saw he was probably average hairy. It was a few years ago so admittedly the only thing about him I remember aside from the awesome blowjob was his voice.

 

[gumshoe]

I'll get to my second time with an older guy, which was about maybe 3 or 4 months after the last post. This one wasn't as fun at all. He was another guy that I chatted with a bit online although I was much more quicker meeting him than the first one. He was late 30s (maybe 36?) and lived in the same neighbourhood as the first guy, since it was a street of just apartment buildings. He lived in a different building though.

So after chatting with him, he invited me over and this time I hesitated less and instead of waiting days, I just went over that evening.

When I got to his building, he buzzed me up as soon as I got there before I put in the buzz code or anything. I went up the stairs to his apartment on the fifth floor and went into his apartment.

This guy lived in a slightly larger L-shaped bachelor apartment where the bedroom was separated by a room-separator. He was waiting in the living room for me.

He was about 5'6 or 5'7, chubby and not very attractive. He had what I call "nerd glasses" and very thin hair, near balding. One of the first things he said was "I saw you come in on the security channel so I buzzed you in." And he had porn on his television already going.

Watching porn with other people isn't really a turn-on with me, and this guy was a bit creepy to me as well but I was horny so I stayed.

I sat next to him on his couch and we watched the tape for a few minutes. It was mostly him doing the talking, mostly about the video, what he liked and disliked about it and how he liked to watch it with the drapes open in hopes of being seen by the neighbours from the next building. An interesting thought, I decided, even though I figured most people might not be interested in watching him, per se, but the idea itself was appealing.

"So you wanted to show me something?", he interjected with a grin.

"Yeah," I said, nervously, and I stood up in front of him and started to unbutton my shirt for him.

"If you want, I can close the blinds if you don't want to be seen." and he got up and closed them though I said "naw, that'll be fine."

I removed my shirt and started to unbutton my pants while he sat there and watched me undress in front of him, the porn still playing on the tv behind me. At this point, I was hard and it was showing through my briefs which was now all I was wearing.

He wanted me to sit on his lap, which I did, as he started to suck on my nipples and play with my hard-on through my briefs. I don't care for nipple play but knowing it was turning on someone else was okay with me.

Then I got up and removed what I had left and let him play with my full, visible dick as he had also taken out his own and was jerking himself off. He soon started to unbutton his own shirt and asked me to suck on his nipples. His chest was quite hairy. Not full but sporadically so. He was probably the definition of a bear though not a well-kept one as he didn't seem to put much effort into his appearance.

I played with his nipples a bit while he kissed my neck and chest and then started to jerk me off. He also wanted me to jerk him and suck him a bit while he breathed heavily and moaned a bit. At this point, my goal was mostly to finish as the porn in the background was still on and was distracting me, not to mention the creepy vibe the guy was giving off.

Finally, I came while standing in front of him on his chest and helped him jerk off onto himself soonafter. I stayed naked for a few minutes while he cleaned himself off and got me a towel to clean up myself and then I quickly got dressed. He offered to walk me as he was headed to the grocery store and we left together, walking to the end of the street where I purposely went to the opposite direction of where I lived because the conversation was so awkward, regarding him noticing how awkward and nervous I was but did little to ease it, probably making it even moreso.

I didn't chat with him again though he was a regular of a younger guy (maybe two years younger than me) that I hooked up with who wanted me to have a 3some with them. I didn't.

 

[gumshoe]

I'll post my next story. The last one kinda sucks and I do realize that it's pretty much the same story one after another but for the sake of completion, I'll finish anyway.

This time happened about a year after the last one after I had moved to another part of the city on my own. I was almost 25 at this point and was online chatting with older guys again. This particular guy I had been talking to on and off for a few weeks and I knew he lived just a few blocks from me in the same neighbourhood. That thought was always there, knowing that I could go pretty much whenever I wanted.

This guy was 58 and was pretty experienced with sexual adventures, having a lot of regulars and into a lot of things. Public sex, voyeurism, exhibitionism with friends, naked car rides, occasional 3 or 4-somes, etc. He also lived with his long-time partner who was early 40s but clearly not as adventurous which might have explained the very open relationship.

So he invited me over one evening after chatting about what I was into. As with before, I decided to finally go ahead with it. He was literally a two minute walk so close enough for comfort. I got dressed and headed over.

He lived in a split-level house where him and his partner lived on the bottom level. He left his door unlocked for me so I got there and walked in. The living room was empty so I took off my shoes and knocked on the door. He came around the corner and was wearing a pair of slacks and a button-up shirt. He was about 6'3, had thinning white hair and big features; hands, face, big frame. He was large but not particularly overweight.

He was to the point when I got there. Knowing full-well that I was nervous and acknowledged it but said that if I wanted to go ahead, it would be something that we would both enjoy so he sat down and told me to go ahead. With that, I took off my sweater and unbuttoned my shirt while his eyes were completely focused on me.
Each time, having the full attention of the daddy is what gets me hard and this guy was by far the oldest I had put on a show for.

We were in his living room which was facing the street and very well lit. The certains were closed but they were white so part of the thrill was knowing that anyone who tried hard enough could have peered through the window to watch.

Next I undid my belt, slowly to built up as much anticipation as I could, and unzipped my jeans. I pulled them down leaving me only in my briefs, which he let out a very slow "niiice".

I walked over to him in my briefs and offered for him to feel my body, which he did. Having those big hands touching my butt through my briefs, around my back, chest, shoulders and belly and then cupping my bulging front sent shivers up and down my spine as I closed my eyes and breathed slowly and heavily, the only sound in the room along with his slow, heavy breathing.

He pulled down my briefs revealing my hard cock which drew in his stare as he put his large hand around it and slowly started to stroke it.

Once again, my fantasy of being the sole naked person in front of a fully clothed daddy was coming true again. He started to suck on me, taking it in deep and making sure it was completely wet for his hand to stroke it without lube.

Then he stands up and unbuttons his own shirt, revealing a slightly hairy chest and belly. He had a slight belly, mostly due to his frame which, despite being large, was thin. Then he unzips his pants, pulls them down and steps out of them, standing only in his boxers and open shirt while I'm still hard and fully naked.

I start to stroke his cock, which was thinner than mine but longer, about 7 and a half inches, and uncut. He starts to moan satisfaction at this while continuing to stroke me but I mention that I want to save mine for later so I keep stroking him until he cums on the floor between us. Not quite a squirter but the amount wasn't minimal.

He pulls his boxers back on and goes to grab a towel while I get dressed, still aroused but able to pack it away. We were both satisfied and since I lived nearby, I shyly assured him I'd be back.

 

[gumshoe]

While I'm here, I'll post the second time with this guy, which was about 2 or 3 months after the first.

Familiarity has usually been an important aspect with me whenever I fooled around with anyone... except when it comes to the old/young, daddy/son idea. But I had fun with the 58-year-old neighbour and he did too, we kept in touch.

The same thing happened the second time as the first time. We chatted online and he invited me over so this time I did. He told me that his partner was home, playing computer games in the bedroom but that he wouldn't likely interrupt (not that that would hinder me at all). He told me that he has walked in on him and another guy before but it's second nature and while he usually goes about his own business, he has joined a few times.
So I went over, the door was unlocked and I went in. This time, I took off my shoes and walked into his house. He was sitting in the room off from the living room on his computer smoking weed.

He was wearing pajama pants and a t-shirt this time and when I got there, stopped what he was doing on the computer and told me to go ahead.

I didn't take my time this time as I did last time though I was still shaking and shivering with anticipation of getting naked. As I stripped, he kept smoking on his joint and watching until I got to my briefs and turned around for him to see the shape of my bubble butt through my underwear before letting him cup it with his big hands and then finally pulling them down.

I moved closer to him and let him suck me for a bit before we moved back into his living room and he lay on his couch and told me to get on top of him. So I put my knees on either side of his torso and my cock in his mouth and pushed in as he pushed his head onto my dick, forcing it all into his mouth, sometimes gagging.

After a few minutes of sucking and licking, we got up and he bent me over and started licking my hole, pushing his tongue in and around while moaning. He placed his hand lightly behind my balls, gently touching and massaging that area, which always gives me shivers and makes me hard as a rock.

For the finale, he turned me around and sucked me until I came in his mouth, each squirt accompanied with a thrust and grunt from me and a moan from him as he swallowed every drop.

As I was getting dressed, I remembered that his partner was just a room away when he briefly made mention of him being home. So I said that it would have been nice for him to come out and "catch" us, even if just to sit down and watch. Unfortunately I wasn't so lucky.

My luck also ended with this guy as he moved the next month. We still chat online occasionally but that's about it. One of my favourite memories!

 

[gumshoe]

I'll post my last experience with an older gentleman which actually turned out to be my favourite one and definitely most fun to tell. This one happened just over a year ago a month or two before I met my current bf (and we've been together for a year).

This guy invited me over to his place which was just a few blocks from me. He was 46, had his own 2-level house and invited me over to just get naked and hang out with him.

I went over and he was waiting for me in his sunroom chatting on his computer. His sunroom jutted out into his backyard which was surrounded with trees. He had offered for me to get naked in the backyard and sunbath if I wanted to but it wasn't quite private for me and I didn't have the guts for that so I declined but told him he could leave the curtains open all the same while I took off all my clothes.

It didn't take me long to get hard as soon as I removed everything I was wearing. For a 46 year old, he was pretty fit. Thin, fit, about 5'9, salt and pepper hair and could have passed for mid-to-late 30s. He worked out for sure though he wasn't muscular.
For awhile, I hung out next to him on his couch chatting with him while fully nude as he surfed the web and chatted on MSN fully clothed. It was a turn-on for me but at this point I wondered...what now?

He gave me a tour of his house in which he lead me around. Walking around his house with an erection that he occasionally looked at was thrilling for me.

When we got back to his sunroom, he told me he was chatting with a friend of his, a guy that he fooled around with occasionally. He told me he mentioned to him that he had a fully naked younger guy hanging out with him and asked me if it was alright if he came over.

My first thought was hesitation but then I wondered... maybe they will let me watch them have sex? I got excited about this idea and said "sure!" He asked me if I had ever gotten a facial, which I had, and told me that him and his friend had been talking about facials for awhile but had never actually done it before.

While we waited, he started to slowly stroked my hard dick and feel my chest and balls a bit. It didn't take long for the friend to show up. By the time the door to the sunroom opened, I was standing over the guy with my dick in his mouth. The friend came in, saw this, pulled up a chair about 5 feet away and started watching.

He was pretty hot! I was thrilled and nervous. He was 30, dark coloured hair, well-built, muscular, very attractive smooth face. Rugged but kept himself shaved and smooth. Dark complexion and eyes but very nice to look at. And he was looking at me.

As the guy continued to suck me off, I moaned. Eventually I looked over at the 30-yo and said "want to join in?" He simply replied, "naw, I'm just here to watch" and continued to intently stare at my crotch which was being licked and sucked by the mouth of the 46 yo, who at this point had pulled out his own uncut, 6.5' dick and was stroking it.

After about ten minutes or so, I was getting close and whispered "I'm cumming". The guy pulled his mouth away and I came all over his face as he kept jerking himself off until about a minute later he came all over his chest.

With this, the friend stood up, hovered over us for a few seconds and said "I came, I saw and I left," which he quickly followed with "well, I didn't come" and he grinned. And he was gone.

We cleaned up, chatted for about ten minutes and then I was gone as well. We chatted a few times since then as well. Hoping to set up a 3some with him and my bf. Hasn't happened yet but hopefully sometime....