There were two guys that lived in my building that I would often see at the mailboxes. Small built, some might say twinks, they were cute. One day they introduced themselves. The dark-haired one said his name was Don, and the blonde guy was Gordie. "You should come over tonight! We have this bottle of wine we've been wanting to try! Come over at 7?" I accepted.
I showered and dressed. They lived two floors up. I knocked on their door. Don answered. "Great! You're here! Follow me!" I followed his swaying ass. "Gordie, open that bottle!" Gordie poured out three glasses of a merlot. We sat on the sofa, sipping wine, and chatting. They were on either side of me. The talk started getting flirtatious, and my cock stirred in my pants. I felt Gordie's hand on my bulge, and Don started kissing me. They fumbled with my buttons, opening my shirt. I felt Gordie's tongue on my nipple. Don opened my belt, and within minutes the two had me naked. They were out of their own clothes quickly. They both dived down, alternately sucking my cock, giggling as they would nudge each other aside. Don won the playful contest, and blew me. Gordie moved up, kissing me and pinching my nipples. "Guys, I'm gonna...." and then I came in Don's mouth. We cuddled for a while, until Don wandered off to bed. Gordie and I made out. He teased my cock back to hardness. "Do you want to fuck me?" he asked. I nodded. He led me to his room. He got some lube out the dresser and meared it over his asshole, and all over my dick. He lay on his side on the bed. I spooned up behind him and entered him. We fucked for long time. Since I had already cum not long ago, I lasted quite a while. Honestly i was getting tired, and would have been happy to quit, but his moans kept me going. I clutched at his dick and jacked him while I thrust. He shot his cum onto the sheets. I continued pounding him until I came in his rectum. We lay there, catching our breath. I got out of bed, dressed and went home.
A few days later, someone from work invited me to a party they were throwing that weekend. I went, but didn't know anyone besides a few people from work. I had been there a while and was thinking about leaving. I wasn't paying attention and backed into someone. I turned and a saw a woman bending to pick up the chips I had knocked out of her hand. "Oh, I'm so sorry!" I bent down to help her. She looked at me over the top of her glasses. "You know, you could have just said hi," she smiled. She was slender, dark hair cut short, and probably early 40s. I learned her name was Celeste. We chatted a while, definitely hitting it off. She said, "Listen, can I ask for a lift home? I rode here with a friend, but she's, ummm, occupied." She nodded over to where a woman was making out with a guy. Celeste tapped the woman on the shoulder and said, "Have fun, Trish. I found a way home."
We got in my car and I followed her instructions to get to her place. I kept glancing over at her, wondering if anything was going to happen with her. I pulled into a drive and parked. "Thanks for the ride!" she said, opening the door. "Here, let me walk you to the door. It's dark out here," I said, getting out and walking around. I walked her to the door and inside the screened-in porch. She unlocked the the door, and turned and hugged me. "You're very sweet, but I'm much older." She kissed me and started to turn away. I held on and kissed her back, a lingering kiss. This time she didn't move away. Our tongues twirled. I cupped a breast. She rubbed my groin. "Oh my, you're hard, and big down there!" She opened my jeans and stroked me. Then Celeste dropped to her knees and started to suck my dick. I gasped and leaned against the wall. She was good, damned good. My fingers were in her short hair. She stopped, looked up at me, and said, "Let's try this..." She popped her middle finger into her mouth and sucked it a few seconds. She resumed sucking my cock, and I felt that hand on my ass, parting my butt cheeks, and then the wet finger was wiggling up into my ass. Her finger probed my prostate as she blew me. I came n her mouth, before I was even aware that it was happening. I heard her gulp. She rose, smiling, a glob of semen on her lips. She kissed me. "I really do need to turn in, but call me tomorrow, OK?" She wrote a phone number on my hand and went inside, locking the door.