- Gay Male
- First Time Hookup
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I have been curious for some time now, and even came close a few times to hooking up with a guy but always chickened out. I've played with dildo's before and gotten off on video chats with other guys but never the real thing. This is the story of my first sexual encounter with another man.
For starters I'm a 30 year old man working in marketing. I am 6' tall and a muscular 195 pounds with just a tough of extra padding around the middle from sitting at a desk too much and eating well that while I have a flat stomach you can't see any abs. I have short brown hair and a neatly kept beard as well as a hairy chest and and neatly trimmed pubes. I have a girlfriend who I enjoy being with, and while the sex is very good, easily the best I've ever had, it is still very basic and unadventurous. She loves it when I go down on her and lick her pussy while sliding two fingers in and curling them up to make her start cumming before I slide my 7" cock into her pussy extending her orgasm until I reach my own. My biggest turn on is getting others off. For a long time I've been bi-curious, but I'd never acted on it in person, just in my fantasies, and I knew even if I do act on it, I'm not going to stop dating women.
I was in NYC on a business trip, staying in a business hotel in Chelsea. After my first day of meetings, I didn't have much to do that evening so I started off at the hotel bar with a few drinks and started getting turned on by the bartender. I stepped out, had some dinner, and then had a couple more drinks at the hotel bar. I continued to flirt with the bartender some, but didn't pursue it. At this point it was starting to get late and I had a pretty good buzz, so I called it a night and when up to my room to likely jerk off alone.
When I got to the room, I showered and cleaned myself up really well before I got into bed. I was going to play with my cock and ass before going to sleep to relieve the tension that had been building all evening. At this point I had a thought, out of curiosity, I turned on my phone and loaded up my account on Adam4Adam that I occasionally use to flirt with other guys. I loaded up the page and looked to see if there was anyone nearby. I found that likely staying in the same hotel as me was Michael. The picture showed a older bald gentleman! This is perfect I thought, I found older men more attractive. Reading more in the profile it listed him at 5'7" and 200 lbs with a 6" cock. At 65, and these proportions I was expecting very much that he had a dad-bod or even a granddad-bod. This got me excited.
I sent Michael a message and he responded quickly with interest. We exchanged pleasantries and interests and I learned that he really enjoys younger guys, while I have a thing for older men. It seemed like a compatible fit, I just had to commit to actually going through with it. Finally I suggested he come down to my room, I'd be waiting for him naked.
I was so nervous waiting, butterflies going crazy in the pit of my stomach. It felt like forever for the two minutes to pass before there was a knock on my door. I went to the door and looked out the peep hole. No backing out now as I opened the door, exposing my naked body to Michael and the rest of the hall as he entered my room.
He looked me up and down and just smiled like it was his lucky day. Michael said "Wow! You are sexy!" And he shut the door behind him. Being NYC, the room was rather small and a few steps in we were at the foot of the queen size bed. He pulled me into him and kissed me right on the mouth. Soft at first, but not like a woman would but more masculine and carnal. Soon my arms were around his neck as we explored each other's mouths with our tongues. My inhibitions were lost and I needed him and needed him now. I dropped my hand to his crotch as we were kissing and started rubbing his dick through his pants. Finally breaking our kiss I put my hands on his chest and slid them down over his sexy pot belly to the bottom of his shirt and fumbled around first removing his shirt and trying to get his pants off. He stopped me like a good daddy and had me sit down while he removed his clothes.
He slide his shoes and socks off, and then unbuckled his pants revealing a pair of black boxer briefs. I reached over to caress his dick again and was rebuffed. He removed them himself and climbed up into a comfortable reclined position on the bed and indicated he was ready for more.
Finally, I could see all of his body. He was fully bald and not too hairy all over but just some light natural hair. He had somewhat thin arms and legs that indicated he did not regularly work out if his large belly did not already give that away. Between his legs though was a still not yet hard dick and a smooth set of balls. It seemed small, potentially smaller than advertised, but I gave him the benefit of the doubt that he'd be a grower and not a shower. Besides I was very horny and determined to give him an enjoyable experience. I crawled between his legs and as I was going to go down and give him a blowjob be pulls me up and we kiss more. Finally I break away and say "please let me suck your cock?"
He relents, and I slide my body down his and position my face in front of his not yet hard 3 inch penis. I wrap my thumb and forefinger around the base of the cock and open my mouth and lick the length of the warm soft fleshy shaft and spongy head. Being nervous and excited my mouth is a little dry so after a few licks I open my mouth and wrap my lips around the cock coxing it into a fully erect state alternately sucking and licking the flesh in my mouth while being careful to keep my teeth away from it. From the the moans and squirming above me I can tell he's enjoying it. I'm pulled up and off what is now a rock hard 4.5" cock and kissed some more. Deep, tongue probing kisses of desire.
From here Michael says that he'd like to play with me for a while. I offer that maybe we could 69 some so I can continue to enjoy his cock. While I'm not happy that it was so small, I was still having fun with it and yearned to make him cum for me. So I climbed over him and placed my knees on either side of his shoulders. Wrapping my hand around the base of his cock I put it all in my mouth and started fucking him with my mouth. He started teasing my cock and sucking it some before shifting me down a little bit and putting his warm tongue right on my ass hole. It felt heavenly feeling his tongue swirl around my ass and encouraged me further. I buried my nose in his balls and created even more suction as I was face fucking him. After just a couple of minutes I felt his whole body tense up and spasm until he couldn't take any more, but his load was so small I barely noticed.
Not having cum yet myself Michael laid me down on my back and started running his hands on my body. He grabbed some lube and began rubbing his forefinger in my crack. I adjusted and pulled my legs up to give better access. At first he just massaged the outside of the hole. It felt so good, but I couldn't take the teasing anymore. I begged him to finger fuck me as I jerked my cock. With that he slide in a finger and began stimulating my ass as I jerked off with my legs in the air like the slut that I am. In no time I could feel that familiar tingle in my balls. They tightened and I blew a huge load all over my stomach and chest.
Michael was nice, he got up and grabbed me a towel to clean up as he cleaned himself off in the bathroom. We exchanged a few pleasantries while he got dressed, though being my first time I was a bit embarrassed. I thanked him for the fun time and he returned to his hotel room.
After a couple of months, I'm thinking about finding another guy for a second play session. This time though I will be hoping for a bigger cock, and I think I might try to fuck him since I love cumming with my ass being stimulated. What do you think?
- COMMENTS
Anonymousover 7 years ago...a neighborhood kid sucked me off twice. Both times I was asleep, waking only a minute or so before the 'consummation' of the act. And both times after I ejaculated in his mouth, he whispered, almost to himself, "that tasted good!"
Fast forward 40 years into the future. I'm married with two children and five grandchildren. My wife has no sex drive anymore, something that has made her cry more than once. For the first 35 years of our marriage, she was almost insatiable.
As my sex life with her dried up, I began remembering my buddy who sucked me off twice. Especially since my wife had never sucked me to completion in all our years together. I began to jack off thinking about it, the feeling of his hot wet mouth on my cock and the way he was hunched over me for one reason, to make me cum in his mouth. Then I learned about the personals on craigslist.
I read them for a few years, fantasizing about some of them. Of course, we all know most listers are weirdos and I just couldn't get past that. Until I happened to see THE ad.
"65 year old happily married man, located in (20 miles from my home), wanting to discuss playing. Wife went through menopause and I can't stop thinking about another man."
My heart was pounding when I hit 'send', contacting him, giving him a brief description of myself and asking questions. His answers were better than I could have imagined. He had played with two or three other kids about 53 years before, they jacked and sucked one another, except none of them could produce sperm. They would just have a dry orgasm in the other's mouth. Steve couldn't forget that and like me, longed to live it again.
I was honest in my reply. What I was looking for was someone to come to my house each morning, as often as possible, and suck my cock to completion once or twice, after my wife left for work. We live in a VERY rural area and I'm retired at 55 with no neighbors. After reading my reply, he wanted to meet and talk, get to know one another.
We met for coffee. It made me feel much better that he was just as nervous as me. He wanted to find a cock to play with, to jack and suck on, as he had so many years before. Something very regular and he couldn't take his eyes off my crotch, embarrassing himself badly, which he admitted. Thankfully we didn't know one another which he didn't want to change. He just wanted to play. If we met in public, he would ignore me.
I was upfront with Steve in person too, explaining about my youthful friend and what it was like for me. He could hardly meet my eyes when I told him, in person, I wanted someone to jack and suck my cock as long as they wanted or as quickly, then I wanted to cum in his mouth, not missing a drop. I thought it would run the poor guy off, but instead he quietly answered, "OK."
He couldn't understand his 'need', because he loved his wife and wasn't attracted to me, exactly as me. We went our separate ways after agreeing to give it more thought. After about three weeks I figured he lost his nerve until I got another email from him. Apparently I'd missed an earlier one and he wanted to make sure I was 'flaking out' on him before placing another ad. I apologized for missing it and we set up a 'date' for him to come to my house.
My guts were in turmoil at the idea. For the next few days I just about shit myself to death with diarrhea. My biggest fear, one I shared with him, was that I would have stage fright and not be able to get it up, even with the Viagra I had. He didn't care, he just wanted to play with my cock, even if I were soft the whole time.
Steve showed up that first time about 5 minutes early. He admitted to being 20 minutes early and kept driving past my driveway, trying to talk himself out of it. Yet somehow he pulled up to my house and knocked on the door. I'd not heard him and answered it wearing my pajamas as we had discussed.
Christ, that first time was beyond awkward, beyond losing my cherry to my more experienced wife so many decades earlier. Two men, one about to suck the cock of the other. Whoa. Yet it went much better than I could have imagined.
Steve wanted to be on his knees. I had recorded a couple soft core porn movies from television and started one. I needed to see tits and cunt because that's what turned me on. Once he was in place and we were both comfortable, he reached in to my pajama bottoms and drew out my cock, exactly as he had fantasized.
I need to explain about my cock and the problems I thought it might provide. When I was younger, my cock was always thick and a little less than 8", uncut. Yet as I aged, it seems to have shortened and I usually run around 7" but am much thicker. MUCH thicker. At the largest point, it is a little over 6 1/2" in circumference. Steve isn't a large man and neither is his mouth.
But he slipped it into the wettest, warmest thing I had felt since my wife's pussy when we were young. His mustache tickle me and kind of weirded me out for a few minutes until I got into the blowjob. Rather than have stage fright, my cock, filled with Viagra, rose to the occasion!
I'd guess that BJ lasted 20 minutes. Yes, a long time. Steve could have made me cum sooner but when I'd get close, he would back off. Finally the time 'came' and he went for the kill, wrapping his lips around the head of my cock and jacked it off with his fist. As we had agreed on earlier, I warned him I was about to cum. Rather than pull off, as I had feared, he never missed a beat, or stroke.
My orgasm was like nothing I could remember in the past. It was all-encompassing, a thing of pleasure I hadn't either known, or had forgotten. I squirted the first three pulses onto his tongue before I felt him swallow. Oh, and to feel him swallow made it even better! My cock continued to cum and I felt as least four more pulses jettison sperm onto his tongue. I finally looked down and found he was stroking his own cock, but not cumming.
Now came my fantasy. He knew I wanted him to leave my cock in his mouth after I was done. He kept it in, being careful to not overdo it on my sensitive cock-head He milked the shaft, squeezing the last few drops out into his mouth. As I had hoped, and had happen with my first time so many decades before with my wife when I lost my cherry, I stayed hard and after a few minutes could continue. That time, with his mouth getting very tired, he mostly jacked me and held the head of my cock in his mouth until I shot another load. He swallowed every drop and milked me as I wanted.
Although his cock was hard, Steve was wanting to leave. But I wanted to talk and have him describe his end of the fantasy. My first question, did he like it? Yes he answered, he loved the entire thing. My second question, did he enjoy feeling me cum in his mouth and did he like the taste? Yes, to both, except it was a bit more bitter than he anticipated, but loved it anyway, probably because of what it was he was doing.
While we talked he left his cock out for me to look at and I asked for. As we talked, his cock would quiver, sticking straight up. He was/is cut with a much more slender shaft about 6" long. I asked him if he wanted to jack off when he did, I asked him to stand in front of me and jerk to orgasm.
My gosh, he was excited. It took less than 30 seconds and he squirted his sperm into the palm of his hand, eating it before he was completely done. Embarrassed, he was ready to leave, promising to contact me later after giving it some thought.
That was the beginning 5 years ago. Steve comes to my house, sometimes once or twice per week, but more likely 3 or 4 times, sometimes all 5, and sucks me off. Usually he sucks me for about 20 minutes if he plans to make me cum twice or 30 minutes if there is going to be only one mouthful before leaving. He wants me to cum in his mouth and nothing else.
We have frank discussions about it still. Although he doesn't like it, I sometimes ask him to cum before sucking me off, just to watch him struggle to suck me. I'm not sure why I enjoy that too much, but I also ask him to jerk off and cum before I do while he sucks me and make sure I cum just as he's coming down from his orgasmic high.
Life is perfect. I am a 'feeder', he is a sucker. We occasionally see one another while out but like we formally planned, neither of us acknowledge the other. Except for one thing. I mentioned if I noticed him and thought about what we did together, I would look at him and tug on my right earlobe. Each time I've done it he turns red and never makes eye contact again. After the first time this happened, he admitting to hurrying into the closest bathroom and jerking off while his wife waited, not knowing anything.
Over the years, I would guess he's sucked me and swallowed every drop at least 750 times, maybe more. He's never missed a drop of my sperm and will occasionally sit around and talk after not swallowing it all, just to keep tasting it. It embarrasses him to admit it, but he enjoys keeping the flavor in his mouth. When we can't meet at my house, he will drive to another location down the road where we can park behind locked gates that I have a key to and he'll suck me off in my truck or even outside in the woods.
Can life get any better?!!!!!!
Anonymousalmost 8 years agoYour first experience was a good one. I think you should go for it and you will eventually find what you really like. I do like a bigger and longer cock and one that is cut. I like taking a lot of time to please each other.
Anonymousalmost 8 years agoYou will find in your further exploits, that different cock for different things. I prefer big fat cocks for sucking. I like thinner short cocks for getting fucked. I like to feel full, but do not want the pain that big thick cocks bring to anal sex. Just a personal preference, but I prefer cut cocks. Keep exploring!!!
Curiousbottom83almost 8 years agoAuthorThanks for the comment. I'm glad you enjoyed the story .
