I have a regular appointment for therapeutic massage with a therapist who comes to my home. He's a hot, well built guy with a great smile and excellent hands. He's been giving me massage for about two years, and I don't know entirely what was different tonight, but he kept brushing his crotch up against my hand "accidentally." Well, I can certainly take a hint & started playing with his cock through his shorts. Before I knew it, his shorts were off, his 7.5x6 cock was in my hands, all oiled up, and his hands were stroking my lower back, ass cheeks, and thighs, with the strokes getting closer and closer to midline until he was running his fingers up and down my ass crack and over my balls. We'd never talked about sex before, and he always ignored my erections when I'd rolled over in the past. I was so turned on my the attention to my ass that it didn't occur to me to tell him I was a total top and hadn't been fucked up the ass since 1984. It was heaven when he started rimming me, and my heart was pounding a mile a minute when I felt him climb up on the table and rub his body and his hard cock up and down my backside. I was incredibly turned on feeling his hot cock sliding along my ass crack, and the searing pain of his cock head entering me reminded me why I hadn't been fucked in over 25 years, but I was so horny I didn't dare ask him to stop no matter how much it hurt. And it was totally hot to be on the other side of a raw fuck, taking his bare cock inside me without knowing anything about his sexual history. He took his time with me, and although the pain never went away entirely, it did abate somewhat with his slow, deliberate, deep strokes. He finally spoke, whispering in my ear that he'd wanted to fuck me every time he'd worked on me, and he loved that he finally had his raw cock inside me. I responded that I had wanted to fuck him, too, but was thrilled to have his cock inside him and wanted him to shoot his load deep inside me. "Don't worry", he said, "I hate it when guys fuck me raw, only to pull out before shooting. I love taking loads up my ass, and I'm going to shoot a huge load deep in your ass any minute now." He picked up the pace, shoved my legs further apart, and really started pumping his cock deep inside me. He moaned and thrust so hard I had that proverbial feeling of being split in two. He stayed inside me and stroked my neck and arms and face for a while, and when he pulled out, he just kept right on with the massage.
When I rolled over, I was rock hard. He worked over my cock & balls with his mouth and tongue and slid a finger up my ass. He pulled me down so my ass was hanging off the end of the table, put my legs over his shoulders, and slid his once-again hard cock inside my very sore ass. I had to ask him to slow down because I was so sore, explaining how long it had been, and he confessed that it was not his usual thing, either. He told me he was 90% bottom, adding that the bareback part, though, was his norm. He told me he usually gets fucked up the ass, raw, through a glory hole at the ABS in town and loves letting anonymous guys use him as a cum dump. To prove his point, he pulled out and told me to switch places with him. I reached for the squirt bottle with his massage oil for lube, but he grabbed my hand and told me he had enough cum in his ass already that it wouldn't be necessary. My rubbed the head of my cock against his hole, and he instantly opened up to me, and he must have had half a dozen loads inside him. I fucked him hard and fast and deep but didn't cum because I was afraid I wouldn't be able to take his cock again if I shot my load, so we switched back. As he started building up a good speed, he told me he loved how tight my hole was, and I told him I loved being fucked hard and used by a cum slut who was going to shoot a second load inside me. He rammed his cock deep to pump his second load inside me, and I shot my own load, seeing my cum flying over my head to land on the head piece of his massage table.
I have another appointment booked in two weeks; I had tried for next week, but he'll be out of town at a workshop next week. He did promise to tell me all about the bath house he's going to hit while traveling and all the loads he gives there.