First Time Hookup

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?