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My First Older Man

by Kayfabian


I met Bruce while finally get the nerve to post a personals ad via craigslist. It had been a year or so since I stopped hooking up with my roommate (we were our first gay experiences), and I was really craving some sexual satisfaction from another man. The exact wording of my ad is lost on me, but it probably read something like “Bi curious guy looking for more experienced guy to show me more”. I added a picture of my cock and an ass shot, then waited for email replies. After skimming through a few duds of the usual craigslist variety, I opened an email from Bruce. He was in his 50’s, divorced, lived alone, acted straight, but had only been with men since his divorce. He attached only a face picture, and promised he’d show me a good relaxing fun time. His face looked his age, and I found the gray streaks along his temples to be kind of a turn on. I initially had zero intention of meeting someone as old as Bruce, but his charm came through in our short email correspondence. Being intrigued, I was in. His only request was to shave my ass smooth -I hadn’t experienced the joys of being rimmed, and he promised me that I’d love every second of it. I arrived at Bruce’s place at his requested time of 1:30pm. I think I sat in the car for a few minutes to gather my thoughts and take a few breaths – I remember being both very nervous and very excited, as I’ve never met up with anyone I’ve never met under the pretense of a ‘casual encounter’. Bruce lived in a decent sized 2 story stucco house, which is pretty much the norm here in suburban Las Vegas. Nothing too fancy, but he did keep his yard nice, and his neighborhood seemed like a relatively safe place to live. I remember looking over his yard and shiny nice car as reasons to not chicken out and make my way to his front door. I was stuck between running away scared and ringing his doorbell – I settled on the latter, and thought to myself, there’s no turning back now. As the door opened, I was put at ease as Bruce’s face matched the picture he sent – this man wasn’t a liar, and he looked just as attractive as advertised. He stood about 6’2, and had to weigh around 220-230lbs. Broad football player build with thick, strong legs to hold up his barrel like upper body. He wore a loosely tied robe that showed off his salt and pepper covered chest and some house slippers. The smile on his face told me that he was happy I was honest about my description, and that my pics didn’t lie. He welcomed me in with a warm hug and a nice passionate kiss on the side of my cheek, his body firm and full – much larger than my own 5’9 150lbs boyish frame. We introduced ourselves and shared beers while he gave me the tour of his house. The inside was as well-kept as the outside, decorated with keepsakes and photo’s – nothing weird or off setting. Everything about this man was legit and normal, and any kind of fear from nerves I had before were completely gone. We finished up the tour in his upstairs master bedroom, with gay porn playing on his DVD player, and his king sized bed stripped of blankets. ‘Go ahead and take your shoes and clothes off and make yourself comfortable’ Bruce suggested, as he sat on the edge of the bed, with his robe now opened, showing off his hairy chest, cock and legs. He was definitely all man – burly and thick from head to toe – I remember noticing how large and manly his calves were and being impressed. I slowly stripped down, feeling excited and nervous as his eyes wouldn’t leave me. I stripped down slowly and left my boxer briefs on per his request. He wanted to take me all in before I joined him in bed, so I stood in front of him blushing and nervous while he smiled and became fully aroused. This man, who in his 50’s looked so stoic and confident and sexy, had my 25 year old self blushing and weak at the knees – ready to do for him whatever he wanted. I let him know I was ready, and that he was in complete control. I was now all his. He asked me to lean in and give him a kiss, and as our lips met I sort of just collapsed into his arms. I was so overwhelmed and lightheaded. I remember my heart beating a mile a minute as our kissing became deeper and more intense. Here I was, with the second man I’ve ever kissed, grinding on his erection, leaking pre-cum out of my now rock hard erection feeling hornier than I ever felt in my life. Just the feel of his embrace gave me goosebumps, and I was suddenly moaning after every movement of his hands. He slipped my underwear off and guided my body into the 69 position with me on top, but with his torso being so large, I kind of just straddled his chest and leaned forward towards his cock. What Bruce lacked in length, he more than made up for in girth. He was about 4” long, but at least 8” thick with balls the size of lemons. I enjoyed his smell, and the way I had to stretch my mouth open to suck him. I was also really glad that I didn’t have to put my gag reflex to the test, as his cock at the very base fit in just enough to get me hotter. He advised me to take my time, that this wasn’t a race, and that he’d be really disappointed if he came in my mouth so early, so I eased back a little bit and started sucking on his huge nuts. My ass was probably about 8 inches from his face as he played with my cheeks and slowly worked a wet finger in and out of my tight hole. He asked me to scoot back closer to his face and to spread for him. Never before had anyone’s face been that close to my asshole, I could feel him literally breathe me in – he passionately pulled my ass right on top of his tongue and began eating me out. I couldn’t help but let out really loud moans as shocks of pleasure ran through me. At one point I remember having to hold onto his hips just so I wouldn’t fall forward from the lust that was shooting through me. I felt like I was melting on his tongue. I started rocking my hips across his face as I stared at his thick hard cock. Bruce eventually had me on my back, then into doggy, never taking his attention off of my smooth hole. This might sound cliché, but I felt like putty in his hands. Before I knew it, he had a small dildo up my tight hole, and I was taking it deeper and deeper with every push. (The few times I tried bottoming with my roommate never worked out because he was too big, and too impatient – he’d never take his time, and it was always too painful to last more than a minute or so.) Bruce asked how I felt, and I was straight up and honest, I replied with “I’m so fucking horny, and I want your dick inside of me right now”. He pulled out the toy and replaced it with his tongue, now actually inside my gaping ass. I look behind and meet his lustful eyes with my own and his face is buried in me. He slips on a condom and lubes up my hole – reminding me of his thickness, but letting me know that he’ll go as slow as I want.

Bruce was so gentle and patient. No matter how well I took his dildo, it was nothing compared to the thickness of his cock. I laid flat on my stomach as he gently pushed inside me. His chest firmly pressed into my back and his tongue caressing my ear. He’d whisper every time he’d push in more, telling me to breathe slowly and to let him know if he was hurting me. It was pretty painful at first, but I didn’t want to stop - I was never this horny and his tongue got me off like I’ve never experienced – I wanted his dick inside me more than anything. It took a while to get used to, but I eventually opened myself up enough to start pushing back and having him thrust in harder and deeper. Now, I’m a pretty masculine man, and prior to this meet up, I wasn’t sure what side of the fence I stood on when it came to my role with other men – but, Bruce had riding his cock and moaning like a porno slut. My cock leaked out so much cum, which surprised me because I was barely half hard. The pillows he placed under my midsection were soaked, and his hairy belly felt stuck to my lower back. He lasted a good 20 minutes riding my ass before he came and collapsed on top of me. After a few moments of making out and him coming to his senses, he pulled his condom filled cock out of me and turned me onto my back. I told him I came several times, but my cock was still stiff as ever. He kneeled down with his cock turned towards my face and deep throated me as I sucked his now tender balls. It took about a minute for me to unload down his throat, and it felt like I came a few gallons, but he swallowed every drop of me. We both dozed off in each other arms for at least an hour

Bruce and I hooked up every Sunday for almost a year. We didn’t do much outside of sex, but I really enjoyed being with him. He opened me up to the joys of gay sex with older men. I’d really like to find an older bud like Bruce. I’ve had some fun experiences with other Daddy’s, but no one quite like him…

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1 Gay Erotic Stories from Kayfabian

My First Older Man

I met Bruce while finally get the nerve to post a personals ad via craigslist. It had been a year or so since I stopped hooking up with my roommate (we were our first gay experiences), and I was really craving some sexual satisfaction from another man. The exact wording of my ad is lost on me, but it probably read something like “Bi curious guy looking for more experienced guy to show me more”.

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