This is a true story. Names and some details have been changed.
I was in Washington D.C. for a work meeting. There were numerous meetings, a few work dinners, and ample time at night to catch up with friends at my favorite gay bars and restaurants. Although I live in San Diego, I spent a considerable amount of time in D.C. for work and had begun to consider it a second home.
Twenty years ago we lacked apps like Grindr or other hookup tools. Instead, we relied on gay chat rooms on AOL and other platforms that are now considered relics of the past.
In late twenties, I was in decent shape and perpetually horny. I came out when I was 18. My name is Seth.
One night, I was in one of the chat rooms and received a message from someone with the username "gayHawaiian." Intrigued, we started chatting. He was one year younger than me, the same height, and had recently come out to his friends and family.
He was visiting from Dallas and staying in Leesburg, Virginia, at the Lansdowne Resort. He told me his name was Kai. I learned that he was born in Hawaii. He worked for a large international corporation and was based out of their Dallas office. After chatting for a bit, we shared pictures (nothing explicit), and I liked what I saw. Kai was really attractive—dark, curly black hair and gorgeous brown eyes. "Very nice," he said, when I sent him my picture.
We chatted online for two hours before I suggested we talk on the phone. I gave Kai my phone number, and it rang within sixty seconds. His voice was deep and soft. We talked for close to two hours about various topics. The call never turned sexual. It felt like a conversation between two old friends reconnecting after a long absence.
During our conversation, I mentioned that I had a partner; we had been together for six years and were in an open relationship. Our love for each other wasn't diminished by sexual exploration. Kai admitted that this was all new for him. He had only recently come out of the closet.
I told Kai I enjoyed chatting and talking to him and asked if he wanted to keep in touch. Then, I took a chance and invited him to dinner the next night. He said he’d love to, but he was staying in Leesburg and didn’t have a rental car. I offered to pick him up. "Really?" he asked. "It’s a forty-five-minute drive from D.C." I assured him that it was no trouble. He quickly agreed. We decided I would pick him up at 5:30 PM, and we’d find somewhere near his hotel for an early dinner and drinks. He said he'd wait at the entrance to his hotel, and I told him what kind of car I’d be driving. He was excited to meet me and get away from his coworkers for a night. We agreed on a casual dinner, where we could both wear shorts and sandals. It was the middle of an oppressive D.C. heat wave, and neither of us wanted to dress up.
The next afternoon, I finished my meeting at 3:00, giving me time to prepare. As I showered, I got hard but didn't masturbate. While it was likely just dinner, there was a chance it could lead to something more. After all, when you put two gay men in their late twenties together, add a generous amount of testosterone, the possibilities become endless.
I drove to Leesburg, fortunately avoiding D.C.'s rush hour traffic. I pulled up five minutes early, and there he was. Smooth, light brown skin, perfect pecs under his white polo shirt, and shorts that fit his ass just right. I wore a light blue polo and shorts as well.
He waved and got in the car. Instead of a handshake, he leaned over and gave me a hug.
Dinner was great. We both enjoyed a couple of glasses of wine. We talked, laughed, and shared information about our pasts, families, and pets (we are both dog lovers). Afterward, we walked to the car and sat for a bit, continuing our conversation. Neither the chat or the phone call from the night before and now the dinner conversation had turned sexual. That was fine with me; I was happy to have met Kai whether or not anything sexual ever happened.
Clearly, I was pleasantly surprised when Kai reached over and held my face. Looking me in the eyes, he asked if he could kiss me. I said, "I thought you’d never ask."
His kiss was intense. Our tongues explored each other’s mouths. While we kissed, I put my hand on his crotch. He was hard, straining against his shorts. So was I.
He asked if I wanted to go back to his room. He was nervous about his coworkers seeing him bring someone to his room, so we came up with a plan. He’d go in first, and I’d follow a few minutes later. He gave me his room number—1221. I waited a bit, went to the elevator, and headed to the twelfth floor.
I knocked softly, and he opened the door with a big smile. He closed the door, pushed me against the wall, and we picked up where we left off in the car.
After a few minutes, we broke apart. He led me to the bed and pulled back the covers. We stood there, looking at each other as we stripped. Sandals off; shirts off; shorts dispensed with. (We had both gone commando, so no underwear.)
Kai’s cock was incredible. A deep mahogany color, probably from his Hawaiian heritage. Around six inches long and really thick. Mine is seven inches and also thick, with big balls. Kai had manscaped his solid black pubic hair, a perfect complement to his cock.
Kai stopped abruptly, his expression a mix of desire and anxiety. "I'm nervous," he confessed. "I haven't been with many guys. I pushed my sexuality aside for so long, trying to fit into what my family expected—straight, get married, have kids, you know. It’s still new to me."
I understood where he was coming from. Everyone has their journey, and I respected that. I gently placed my hand on his shoulder. "Hey, there's no rush. We'll take things slow. Whatever you're comfortable with, okay?"
Relief flashed across his face. "Thanks, Seth. I really appreciate it."
We settled back onto the bed, continuing to explore each other gently. He ran his hands over my chest, feeling the contours of my muscles. I did the same for him, marveling at the smoothness of his skin.
We were holding each other's cocks and balls. The weight of his thick, dark cock in my hand contrasted perfectly with the lighter shade of mine. Kai's veins stood out prominently, and the large, swollen head of his cock was leaking precum.
Kai moved down the bed, and his lips wrapped around the head of my cock. I felt a jolt of pleasure as his tongue flicked over the precum that had gathered there. His mouth was warm. He took me deeper as he worked his way down my shaft. At one point, he went a little too far and gagged. He stopped for a minute and looked at me, saying, “Remember, I’m new to this.”
The veins in my cock pulsed with each stroke of his tongue, and I could feel his nose brushing against my pubic hair.
As he sucked, Kai’s hands came into play. He wrapped one hand around the base of my cock, moving it in a steady, rhythmic motion that complemented his sucking. The combination of his lips and hand was electrifying, and I couldn't help but moan louder. Meanwhile, his other hand found my balls, gently pulling and massaging them.
Feeling the pleasure building, I knew I was getting close. I warned him, "I’m about to cum. You can pull off and let me cum on my stomach if you want."
Kai paused for a moment, taking my cock out of his mouth momentarily. He looked up at me and said, “No way...I’m going to swallow your cum.”
He returned to sucking me. The urgency in his movements intensified, his lips and tongue working feverishly as he drove me toward climax. I could feel the orgasm approaching. Each stroke of his tongue and squeeze of his hand pushed me closer to the edge. Unable to hold back any longer, I exploded, my cum shooting into his mouth. Kai swallowed it all.
As the waves of ecstasy subsided, I collapsed back onto the bed, panting heavily. Kai lifted his head and came up the bed to give me a kiss, sharing the taste of my cum.
After a few moments, I regained my composure and pushed Kai onto his back. I was eager to reciprocate. I needed to suck his cock. The urge was primal. I climbed between his legs and took his cock into my mouth. After sucking for a few minutes, I put his balls into my mouth, using both hands and my tongue to massage and stimulate them thoroughly. I gently rubbed his perineum, focusing on the area where his prostate resides, causing him to moan and squirm.
I returned to sucking Kai’s cock, and after a few minutes, it was clear that he was close. I took him to the edge, only to pull back, bringing him down just as he was about to climax. This teasing continued for a while. Finally, it was time. I sucked on his cock while pulling on his balls, feeling them tighten—a sure sign he was close. He told me he was going to cum, and I increased the intensity of my sucking, feeling his cock spasm in my mouth.
I was surprised by the intensity of Kai’s orgasm. It was explosive, and he squirted more cum than I knew was possible, his body convulsing with the force of his release. I swallowed it all, savoring the taste and the satisfaction of having brought him to such an intense climax. As the last waves of his orgasm subsided, I continued sucking on his softening cock.
Kai's orgasm was the most intense I had ever witnessed. He apologized for it, his voice tinged with embarrassment, saying that he was sorry that he was so out of control when he came. I looked up at him, confused. "What are you apologizing for?" I asked gently. "The intensity of your orgasm was amazing to witness. It shows how much you enjoyed it, and that makes me happy."
His face softened, a mix of relief and gratitude replacing the embarrassment. "Really?" he asked. "You didn't mind?"
"Not at all," I reassured him. "It was incredible. I loved every second of it." I told him that I had never been with someone whose climax was so dramatic. It was a sight to behold.
We crawled under the covers, and I took Kai into my arms. He put his head on my chest, and we talked about what had just happened. Kai then asked me if he could tell me something: "I have never fucked another man and I’ve never been fucked." He then told me that the totality of his experiences with other men had been mutual masturbation and a few blowjobs. He was clearly a quick learner.
It was getting late, and I needed to leave. Kai asked if I wanted to spend the night. While I would have loved to, I had an early morning meeting and didn’t want to risk getting stuck in rush hour traffic. I got dressed, and Kai put on a robe.
We kissed and then sat on the edge of the bed. "When can I see you again?" he asked. He told me that he would be leaving for Dallas the following evening after his day of meetings. I was scheduled to leave two days later.
We then hatched a plan. I had a nonstop flight to San Diego. Maybe I could change it; leave on an early morning flight that had a layover in Dallas. One of the perks of my constant travel was the ability to change flights at the last minute. I called the airline, and yes, flights were available. I would leave D.C. at 6:00 a.m. (5:00 a.m. Dallas time) and be in Dallas by 9:30. Kai would pick me up at the airport, and we would spend the day together. The last flight out of Dallas to San Diego was 10:45 p.m. We would have more than twelve hours to spend together.
And so it began.
There's a wealth of material I could delve into about this remarkable chapter in my life—where a blossoming relationship evolved into a deep and meaningful friendship.
I was in Washington D.C. for a work meeting. There were numerous meetings, a few work dinners, and ample time at night to catch up with friends at my favorite gay bars and restaurants. Although I live in San Diego, I spent a considerable amount of time in D.C. for work and had begun to consider it a second home.
Twenty years ago we lacked apps like Grindr or other hookup tools. Instead, we relied on gay chat rooms on AOL and other platforms that are now considered relics of the past.
In late twenties, I was in decent shape and perpetually horny. I came out when I was 18. My name is Seth.
One night, I was in one of the chat rooms and received a message from someone with the username "gayHawaiian." Intrigued, we started chatting. He was one year younger than me, the same height, and had recently come out to his friends and family.
He was visiting from Dallas and staying in Leesburg, Virginia, at the Lansdowne Resort. He told me his name was Kai. I learned that he was born in Hawaii. He worked for a large international corporation and was based out of their Dallas office. After chatting for a bit, we shared pictures (nothing explicit), and I liked what I saw. Kai was really attractive—dark, curly black hair and gorgeous brown eyes. "Very nice," he said, when I sent him my picture.
We chatted online for two hours before I suggested we talk on the phone. I gave Kai my phone number, and it rang within sixty seconds. His voice was deep and soft. We talked for close to two hours about various topics. The call never turned sexual. It felt like a conversation between two old friends reconnecting after a long absence.
During our conversation, I mentioned that I had a partner; we had been together for six years and were in an open relationship. Our love for each other wasn't diminished by sexual exploration. Kai admitted that this was all new for him. He had only recently come out of the closet.
I told Kai I enjoyed chatting and talking to him and asked if he wanted to keep in touch. Then, I took a chance and invited him to dinner the next night. He said he’d love to, but he was staying in Leesburg and didn’t have a rental car. I offered to pick him up. "Really?" he asked. "It’s a forty-five-minute drive from D.C." I assured him that it was no trouble. He quickly agreed. We decided I would pick him up at 5:30 PM, and we’d find somewhere near his hotel for an early dinner and drinks. He said he'd wait at the entrance to his hotel, and I told him what kind of car I’d be driving. He was excited to meet me and get away from his coworkers for a night. We agreed on a casual dinner, where we could both wear shorts and sandals. It was the middle of an oppressive D.C. heat wave, and neither of us wanted to dress up.
The next afternoon, I finished my meeting at 3:00, giving me time to prepare. As I showered, I got hard but didn't masturbate. While it was likely just dinner, there was a chance it could lead to something more. After all, when you put two gay men in their late twenties together, add a generous amount of testosterone, the possibilities become endless.
I drove to Leesburg, fortunately avoiding D.C.'s rush hour traffic. I pulled up five minutes early, and there he was. Smooth, light brown skin, perfect pecs under his white polo shirt, and shorts that fit his ass just right. I wore a light blue polo and shorts as well.
He waved and got in the car. Instead of a handshake, he leaned over and gave me a hug.
Dinner was great. We both enjoyed a couple of glasses of wine. We talked, laughed, and shared information about our pasts, families, and pets (we are both dog lovers). Afterward, we walked to the car and sat for a bit, continuing our conversation. Neither the chat or the phone call from the night before and now the dinner conversation had turned sexual. That was fine with me; I was happy to have met Kai whether or not anything sexual ever happened.
Clearly, I was pleasantly surprised when Kai reached over and held my face. Looking me in the eyes, he asked if he could kiss me. I said, "I thought you’d never ask."
His kiss was intense. Our tongues explored each other’s mouths. While we kissed, I put my hand on his crotch. He was hard, straining against his shorts. So was I.
He asked if I wanted to go back to his room. He was nervous about his coworkers seeing him bring someone to his room, so we came up with a plan. He’d go in first, and I’d follow a few minutes later. He gave me his room number—1221. I waited a bit, went to the elevator, and headed to the twelfth floor.
I knocked softly, and he opened the door with a big smile. He closed the door, pushed me against the wall, and we picked up where we left off in the car.
After a few minutes, we broke apart. He led me to the bed and pulled back the covers. We stood there, looking at each other as we stripped. Sandals off; shirts off; shorts dispensed with. (We had both gone commando, so no underwear.)
Kai’s cock was incredible. A deep mahogany color, probably from his Hawaiian heritage. Around six inches long and really thick. Mine is seven inches and also thick, with big balls. Kai had manscaped his solid black pubic hair, a perfect complement to his cock.
Kai stopped abruptly, his expression a mix of desire and anxiety. "I'm nervous," he confessed. "I haven't been with many guys. I pushed my sexuality aside for so long, trying to fit into what my family expected—straight, get married, have kids, you know. It’s still new to me."
I understood where he was coming from. Everyone has their journey, and I respected that. I gently placed my hand on his shoulder. "Hey, there's no rush. We'll take things slow. Whatever you're comfortable with, okay?"
Relief flashed across his face. "Thanks, Seth. I really appreciate it."
We settled back onto the bed, continuing to explore each other gently. He ran his hands over my chest, feeling the contours of my muscles. I did the same for him, marveling at the smoothness of his skin.
We were holding each other's cocks and balls. The weight of his thick, dark cock in my hand contrasted perfectly with the lighter shade of mine. Kai's veins stood out prominently, and the large, swollen head of his cock was leaking precum.
Kai moved down the bed, and his lips wrapped around the head of my cock. I felt a jolt of pleasure as his tongue flicked over the precum that had gathered there. His mouth was warm. He took me deeper as he worked his way down my shaft. At one point, he went a little too far and gagged. He stopped for a minute and looked at me, saying, “Remember, I’m new to this.”
The veins in my cock pulsed with each stroke of his tongue, and I could feel his nose brushing against my pubic hair.
As he sucked, Kai’s hands came into play. He wrapped one hand around the base of my cock, moving it in a steady, rhythmic motion that complemented his sucking. The combination of his lips and hand was electrifying, and I couldn't help but moan louder. Meanwhile, his other hand found my balls, gently pulling and massaging them.
Feeling the pleasure building, I knew I was getting close. I warned him, "I’m about to cum. You can pull off and let me cum on my stomach if you want."
Kai paused for a moment, taking my cock out of his mouth momentarily. He looked up at me and said, “No way...I’m going to swallow your cum.”
He returned to sucking me. The urgency in his movements intensified, his lips and tongue working feverishly as he drove me toward climax. I could feel the orgasm approaching. Each stroke of his tongue and squeeze of his hand pushed me closer to the edge. Unable to hold back any longer, I exploded, my cum shooting into his mouth. Kai swallowed it all.
As the waves of ecstasy subsided, I collapsed back onto the bed, panting heavily. Kai lifted his head and came up the bed to give me a kiss, sharing the taste of my cum.
After a few moments, I regained my composure and pushed Kai onto his back. I was eager to reciprocate. I needed to suck his cock. The urge was primal. I climbed between his legs and took his cock into my mouth. After sucking for a few minutes, I put his balls into my mouth, using both hands and my tongue to massage and stimulate them thoroughly. I gently rubbed his perineum, focusing on the area where his prostate resides, causing him to moan and squirm.
I returned to sucking Kai’s cock, and after a few minutes, it was clear that he was close. I took him to the edge, only to pull back, bringing him down just as he was about to climax. This teasing continued for a while. Finally, it was time. I sucked on his cock while pulling on his balls, feeling them tighten—a sure sign he was close. He told me he was going to cum, and I increased the intensity of my sucking, feeling his cock spasm in my mouth.
I was surprised by the intensity of Kai’s orgasm. It was explosive, and he squirted more cum than I knew was possible, his body convulsing with the force of his release. I swallowed it all, savoring the taste and the satisfaction of having brought him to such an intense climax. As the last waves of his orgasm subsided, I continued sucking on his softening cock.
Kai's orgasm was the most intense I had ever witnessed. He apologized for it, his voice tinged with embarrassment, saying that he was sorry that he was so out of control when he came. I looked up at him, confused. "What are you apologizing for?" I asked gently. "The intensity of your orgasm was amazing to witness. It shows how much you enjoyed it, and that makes me happy."
His face softened, a mix of relief and gratitude replacing the embarrassment. "Really?" he asked. "You didn't mind?"
"Not at all," I reassured him. "It was incredible. I loved every second of it." I told him that I had never been with someone whose climax was so dramatic. It was a sight to behold.
We crawled under the covers, and I took Kai into my arms. He put his head on my chest, and we talked about what had just happened. Kai then asked me if he could tell me something: "I have never fucked another man and I’ve never been fucked." He then told me that the totality of his experiences with other men had been mutual masturbation and a few blowjobs. He was clearly a quick learner.
It was getting late, and I needed to leave. Kai asked if I wanted to spend the night. While I would have loved to, I had an early morning meeting and didn’t want to risk getting stuck in rush hour traffic. I got dressed, and Kai put on a robe.
We kissed and then sat on the edge of the bed. "When can I see you again?" he asked. He told me that he would be leaving for Dallas the following evening after his day of meetings. I was scheduled to leave two days later.
We then hatched a plan. I had a nonstop flight to San Diego. Maybe I could change it; leave on an early morning flight that had a layover in Dallas. One of the perks of my constant travel was the ability to change flights at the last minute. I called the airline, and yes, flights were available. I would leave D.C. at 6:00 a.m. (5:00 a.m. Dallas time) and be in Dallas by 9:30. Kai would pick me up at the airport, and we would spend the day together. The last flight out of Dallas to San Diego was 10:45 p.m. We would have more than twelve hours to spend together.
And so it began.
There's a wealth of material I could delve into about this remarkable chapter in my life—where a blossoming relationship evolved into a deep and meaningful friendship.
