I was at a business convention and saw my friend Shawn. Shawn is about 40, single, and pretty much a loner. I had asked him to run a few errands for me, and I took him to lunch to show my appreciation. I asked how he was doing and what was going on in his life. His dad recently passed away and he was alone. He told me he was ok, but he feels alone, like there is him, and then everyone else. I told him I know how it feels, because I feel the same way and just make the best of it. When we finished talking, he gave me a hug that lasted longer than a thank you hug, and I told him he was welcome to come along with a few of us to dinner after the lectures. During dinner, there was a lot of joking, and at one point, Shawn lay his head on my chest, jokingly, but it made me wonder.
After dinner, I asked Shawn to help me carry some books up to my room that I bought after the lectures. We went upstairs to my room and he saw I had a king size bed, and asked if I was sharing the room with anyone, and I told him I had it to myself. I asked where he was staying and he said he was sleeping on a couch of some friend who lived in the next town. I told him if he didn't feel awkward about it, he could sleep here with me. He thanked me but said he didn't have anything to change into for the morning. We are both chubby guys and roughly the same size, so I offered some of my things for him to wear in the morning. He said that would be great, but he would also need a pair of underwear, so he probably should get back. I said I had plenty and he was welcome to some of mine if he didnt mind. He looked really surprised when I offered him my underwear, and said he never wore anyone else's underwear before. I said that it all gets washed so its no big deal, and he said its kinda like sharing intimacy. I agreed and said I thought it was OK to share some intimacy with a friend. He smiled and said that was more intimacy than he had ever shared with a friend. I said if you like someone, you share more of yourself with them. He smiled and said he was glad I was his friend. I told him I was glad too. He stared at me and pressed his lips against mine. I parted my lips and let his tongue slide into my mouth. I held him tightly let our tounges duel. He asked if that kind of intimacy was OK, and I said it was most welcome.
As we continued kissing, I slid my hands under his shirt, feeling his slightly hairy chest and his wonderful man tits. We took our shirts off and felt each other with our hands and then our chests against each other and finally I lifted his arms and licked his medium brown armpit hair. He moaned as I explored his body and tried to give him more and more pleasure. He said it was a long time since anyone tried to pleasure him. I undid his pants and pulled them down, revealing his sweaty cum stained briefs. They had a wonderful smell to them, and I felt his thick 6.5 inch cock through them. He hung his head low and said he wasn't that big. I told him he was bigger than I am and it wasn't about size, but who it was attached to. He had me stand up and kissed me as he slid down my pants and briefs. His hand felt wonderful on my cock and balls, and he got on his knees and started sucking me. He was good at it and it felt incredible. I had him get up and I got on my knees and pulled down his briefs and licked his cock head and took his leaking cock in my mouth, enjoying the feel and taste of it. I played with his balls and his pubes as I sucked him, as he moaned loudly. I loved the feel of his veiny shaft in my mouth as I went up and down with my mouth.
We finished getting undressed and lay in the bed, holding and hugging each other. He said its been a long time since anyone showed him any affection. I told him I loved being affectionate and was hoping we could do even more. We kissed as I played with his hairy crotch and he asked what I would like us to be doing. I said I'd love to feel him inside me tonight. His eyes widened and he asked if I was sure. I told him it would mean a lot to me if he did it. He stuttered a bit and said he didn't have a condom. I told him he could do it without one. He was surprised and asked if I was sure. I said there was no one I knew who's cum I'd want inside me more than his.
He started kissing me, moving down my body with kisses, sucked my cock and then lifted my legs and started licking my asshole. I moaned softly as he rimmed me and then fingered me. He pressed my legs against my chest and I held them as he pressed his hard cock head agianst my ass hole. I felt him pushing in and I pushed out to make his entrance easier. I groaned in delight as his hard cock found its place inside me. He tongue kissed me as his hard cock started moving in and out of me. I wrapped my legs around him as he pumped his cock deep inside me. I told him how good it felt to have him in me, and he said he enjoyed our closeness. I told him how much I loved that we could share ourselves like this. He said he never felt this close to anyone before. He started thrusting harder and said he was going to cum. I wrapped my legs around him and told him to fill me with his load. I felt his ejaculations filling me. It was hot and he pulled out and stroke me until I shot my load.
There were a few more days of our conference, so I told him he could get his things and move in with me. In the morning, I gave him some of my clean briefs to wear, as he dressed and went to get his things. I spent the time sniffing his sweaty cum stained briefs. When he got back to the room, he saw me wearing his breifs and sporting a hardon. I told him it made me horny to wear his briefs and have my cock where his cock was. We showered and dressed and got ready for the next day of seminars.
After sitting in seminars all day, we went to dinner with some friends, and left early. We went to our room and got undressed. Shawn got on top of me and gave me a full body sensual massage, using his tongue and fingertips. He massaged my cock and balls using his feet, which felt incredible, and sucked me until I shot my load in his mouth. I massaged him and sucked his balls before going down on his hard cock. I lay on my side and he slid his cock inside me from behind. He held me and played with my nipples as he slid his hard cock in and out of me. He reached around and stroked my cock. We moaned in unison as he shot his load inside me.
The next day the convention was over, and I flew home. I hope to see Shawn at the next convention.