Maybe he wasn’t asleep. Maybe he just didn’t know what to do. I certainly didn’t. I knew what I wanted to do, but I respected him so much and had already risked it once. I decided not to try anything brash but gently prod. I had been massaging his feet for quite a while and decided to offer other services.
“Robert, your feet are nice and loose. I don’t want to overdo them.” I don’t think that’s actually a thing - massaging too long - but I knew he wouldn’t know either. “Can I help anywhere else?”
He opened his eyes and sat up just a little. In his eyes, I could tell he knew what I was hinting at. I knew he wouldn’t dare ask. He was straight and probably didn’t want it and I thought of a different angle.
“Robert, can I ask you something?”
He said “of course” and sat up even more.
“Sorry, this is probably way too personal. Have you been with anyone since your divorce?”
He didn’t answer right away so I tried to make the approach even gentler. “It’s just, I know you’re not the type of man who would have a one-night stand. And you told me previously that you hadn’t been in a relationship in a long time. So I’m connecting the dots. Robert, it’s not healthy to be pent up like that. I know the conversation we had at lunch and I’m not trying to make any advance or anything. I know you’re not gay. But, people do this all the time. There are discrete parlors where people can go and get relieved a bit in a plutonic situation.” I started rubbing his feet gently again. “I think you need that. I think your body probably needs that.”
I rubbed his feet for a few seconds and he seemed to mull it over. I decided to act. I gently let his feet down and knelt beneath him. “Stop me anytime, Rob.” It was the first time I called him that like he had always asked. I undid his zipper and pulled down his pants but it was a little difficult because he was already hard. I wanted to get started before he stopped me. I managed to get his pants down to his ankles and then pulled his underwear gently over his bulge and down his legs. His cock sprung up and I started gently tugging. I didn’t have lotion so I had to go slow and gentle. His body relaxed and he leaned back in his chair and closed his eyes again. His dick was thick like his frame and I was in disbelief that I managed to get here. I kept rubbing him gently up and down and knew that I’d have to apply saliva somehow or this wouldn’t be that pleasurable. I debated which would be least uncomfortable for him, covering my hand in spit or just taking him in my mouth. After a minute or two of a gentle handjob, I decided to take the plunge.
I opened my mouth wide and took in his massive, pink-purple mushroom head. We were past the point of no return and even though this might be uncomfortable for him, I knew that he would at least physically enjoy it. I bobbed slowly up and down, not taking him all the way yet. I swirled my tongue a bit and he exhaled slowly out his nose. I could tell he was starved for pleasure and knew this was my chance. Maybe I could make him feel so good that he wouldn’t be able to forget it. It was a long shot, but I never thought I’d get this far. I dove deeper and forced my throat open. He was so big that I couldn’t take him all the way in. I wanted to push my nose all the way to his pubes but I couldn’t. My efforts made my saliva drip everywhere. I wanted to rub his balls to increase the pleasure, but I was worried how he’d respond. Instead, I kept bobbing up and down his shaft and sucking and licking in every assortment of ways. I tried to go all the way down again and got his pubes tickling my nose and face but still couldn’t reach the base. I gagged and coughed in my effort to take him all the way and came up for air a little embarrassed. His eyes were still closed and I caught my breath by focusing on just his cock head for a minute. I licked it while taking just the mushroom in my mouth. I licked the edges and sucked like I was trying to get his cum through a straw.
I twirled and twirled and decided to try one more time to reach the base. I relaxed my throat and lowered myself slowly, fighting my gag reflex as I reached the bottom. I felt the tickle of the stray hairs telling me I was close and pushed down all the way. Finally reaching the base, I held myself there as long as I could before coming up for air. I tried not to gasp and caught my breath quietly for a moment. Again, I focused on his head while I caught my breath. He was starting to shift and I knew he wouldn’t last as long as I wished. He was an older man but he was also pent up. I looked up at his beautiful, serene face while I worked the edges of his mushroom. His chubby cheeks and light stubble were amazing. His grey hair was neat and distinguished. His legs were powerful and hairy, but the hair was light and soft. His body was heavy and strong. I wish I could see what was beneath his sweater and admire his hairy torso and belly. I wanted to play with his nipples and rub the hair from his navel to his cock. I took in more of his shaft and sucked hard. Like I had massaged his feet, I tried to apply more and more pressure. It was working. He bucked a little and shifted his hips forward. I held his legs steady with my hands and dove all the way down. This time I sucked hard with all of him inside me and he squirmed. He grabbed my head with his hand and luckily just rested his hand there and didn’t hold me down. I needed to come up for air because I knew he was about to shoot and I wanted to take him.
I took a big breath and dove down really trying to push him over the top. I bobbed up and down and then all the way down again. I felt his belly rise above my head and his breath became strained. He started to moan softly and I held my position, just above the base of his cock. Again, he placed his hand on my head and grunted hard as he came in my mouth. Unsurprisingly, his cum kept flowing. He shot out over and over again while I tried to keep it all in. He really started to quake beneath me and he couldn’t suppress his grunts. I was so close to orgasm just feeling him and hearing him in such pleasure. I held my mouth in place and savored the experience as much as I could. When he finally stopped cumming, his grunting stopped as well and I could hear him catching his breath as my face and arms moved up and down with his heaving body. I swallowed with his cock still in my mouth causing him to buck one last time and I released his dick from my mouth with a pop. I gently tugged his wet dick a couple more times and then wiped the slit quickly with my thumb. His eyes were still closed so I put it in my mouth and got my last taste and admired his spent body slumped in his chair.