I went to law school at a decent school in a nice city in the midwest. When I got to law school I was 24, 6'4" and 240 pounds. I was pretty built but not super muscular, and was not super lean either. I was definitely in good shape but on the beefy side of muscular.
I definitely present as a masculine "broish" type of guy due to my size and looks, even though that is not necessarily a good reflection of my actual personality. I'd always been mostly into girls but would occasionally find myself online cruising for guys--a habit that started when I was just a teenager.
Before coming to law school, other than a few less than fully executed experimental encounters with my friends growing up, I had never had an "organic" gay experience. Meaning that I had only found dick on the internet and my preference, when the mood struck, was always for anonymous no strings attached encounters.
I'd always been interested in sucking dick when I would seek out gay hookups. I had only had one experience with receiving anal before law school (met a middle aged guy while on vacation in Miami and he fucked me in his hotel room). I guess that isn't entirely accurate, when I was a teenager, a 40 something guy took me to his house and I sucked him off and he talked me into letting him try to fuck me. I was a scared teenager and I couldn't get through the initial pain of insertion of his oversized dong.
During undergrad I had somehow been convinced by a few guys to let them suck me off and massage me etc in exchange for some cash (they would mostly solicit me through dating apps). I'm not saying that I was anything special, but I think there was something about being a big masc younger guy with a professed interest in older guys that got me a lot of attention back then. Fun times.
Anyway, during my first year of law school I did this housing clinic where we would help locals with landlord tenant stuff, and other similar issues. Although I had hooked up with one guy when I first got into town for school, I was getting enough pussy to keep me distracted, and had not been online looking for several months. It comes in waves for me.
One fall day our clinic was doing a "self-help clinic" at a local library where we would let people come with their legal issues related to housing and we would try to point them in the right direction. A lot of people late on their rent and other such issues would come and try to get the basics on defending themselves. On this day, as the hours wound down, this older gentleman came and sat in my makeshift office in the back of the library area. His name was Dominic. He had some questions about something that the city was trying to do with his land and he wanted some help understanding exactly what was going on.
Dom was a nice italian looking bald man. I'm a tall guy so everyone seems average size or below to me, but Dom was about average, maybe 5'10" slender but not quite frail. His paperwork indicated that he was 70 years old. He looked healthy for his age, but he also had a slight hunch and a slightly labored way of moving.
He explained what was happening and asked me some questions. I mostly didn't know the answers, as his questions were a little outside the realm of the typical housing clinic questions. I told him that what he was asking was a little bit outside of my forte and I couldn't tell him more without doing a little bit of research. There also appeared to me some paperwork missing from what he had. I told him that he could come back to the clinic the next week and I would see if someone could help him.
He asked me if he could hire me to help him with his issues. I told him that since I was a law student I would not be able to actually practice law, and that it would be pretty clearly frowned upon by the clinic people. I told him if he wanted to follow up with me I would see what I could find out. We chatted for a few minutes and I told him a little about myself and what I wanted to do after school. It seemed to be all benign chatter you would expect from a potentially lonely somewhat older gentleman. Feeling friendly and helpful, I gave Dom my cellphone number and told him he could call me to tell me about the papers we discussed once he found them.
Two days later, after class on a Thursday afternoon I noticed that I had a missed call and voicemail from a local number. I listened to the voicemail "Hi Michael its Dom, we met at the library the other day, I found some of those papers and was calling to give you an update. Hopefully you can take a look at them and tell me what you think."
I was slightly annoyed now that I had moved on from the polite conversation. I contemplated not returning the call and waiting to see him at the next self help clinic hours. However, I wasn't sure if I would be the one to see him at the next hours, and I didn't particularly want him to speak ill of me if I flaked on him.
I called him back. Dom was friendly, polite and grateful that I called back. He mentioned that he lived in a neighborhood that was on my walk back from school to my apartment. I told him that he could meet me at the clinic the following week and bring the papers. He asked me if there was any chance I could come to his home to take a look. He asked very politely. I did not feel pressured. It seemed like a nice guy asking for a favor without expectation. I explained to him that I was sort of walking through his neighborhood on my way home from class. "Well, if you're willing, you could stop by now." Overwhelmed by polite older guy friendliness, I agreed to come to his home.
About 10 minutes later I arrived at Dom's house. One of those nice bigger homes that you find in the nicer neighborhoods in cities. He greeted me at the door in a button up shirt tucked into some slacks. We shook hands and he let me into his living room area. It was fairly cluttered and the only open space was on the couch. We sat near eachother, and I could see the papers were on his coffee table.
We went through the papers. I gave him an educated guess about his situation with the caveat that I did not really know what I was talking about. He told me how grateful he was that I came and said some complimentary things about my future career success. I stayed to chat because it was nice to be out of the law school annoying rat race and to be around a "normal person."
After several minutes of very basic and friendly chatting he looked at me with an odd look and stated "Michael, would you like to come upstairs." Given my past experience, I could get a sense when a horny guy was into me, but again, I had never experienced it "organically" before.It threw me into a real tailspin. My first reaction was to second guess myself that he would know to even ask me that. I also started to feel like he may have been asking something else and I was just being a weirdo. His question was so polite yet so bold it took me completely off guard. I stammered "what do you mean?" Dom scooted slightly closer to me and touched my leg and said "I think you know what I mean Michael." He stared at me calmly yet firmly.
Even though I have sex with guys, I don't usually sit and think about fucking the guys I'm with. when I hook up online I usually find myself in a horny state and choose my hookup through a process of elimination (and sometimes sacrifice, depending on the situation). So, I hadn't thought about fucking Dom. I hadn't checked him out. I had always gravitated towards hooking up with "older" guys, but it had always been in the 40s and 50s. However, as soon as the thought entered my mind that Dom was looking to hook up, I immediately knew that I was interested.
"Well, I'm not sure what you are looking for, I'm only into certain things." I said, selfishly (I think). However, I am usually quite particular about hooking up with guys and always look to make sure I am going to get what I want out of the situation as far as compatibility.
"Would you like to go to the bedroom and talk about it?" Dom said, stroking my leg now. "I think we can work this out."
"Sure."
"That's great." He stood up and pointed towards the stairway behind the living room area, and looked at me to make sure I was really comfortable with what was about to happen. I nodded. Getting nervous and excited now. He walked to the stairs and I followed him. He turned back with a slight smile at one point to make sure I was coming.
He entered the bedroom and sat on the bed and lightly tapped the bed next to him. I sat down. He turned to me and began lightly stroking my chest and shoulders. "I am so happy that you agreed to come up here."
Still focusing on my own insecurities, I asked him "What made you think I would be interested?"
"I just figure at my age you can get away with asking for what you want." We both laughed. "So Michael, you are a very hot guy, it looks like you have a very nice body. Can I ask you to show it to me?"
"Sure."
I stood up. I had already kicked off my shoes in the living room after he invited me upstairs, sort of as a habit, I guess. I pulled off my shirt, and he made a noise of approval as he looked me over. After the polo I was wearing was off, I unbuckled my jeans and pulled them off rather quickly. I took off my socks before pulling down my boxers. Dom smiled widely as he looked me over. One of the hottest moments for me hooking up with older guys is that moment when I get completely naked before them before we start what we are about to do. I feel like in that moment the daddy I am about to service knows that I am there for his pleasure, and he can do what he wants with me. After a brief moment soaking in that feeling, I sat back next to him on the bed.
"You really are a hot boy. Now, tell me what you like." Dom said as he stroked my chest and stomach, getting close but not touching my cock.
"Well, honestly, I'm really into servicing guys." I said, as I rested my hand on his leg. "But I mostly like whatever daddy likes." I said, dropping into full submissive mode.
"Oh, that's really nice. I think we can have some real fun." Dom said as he stood up and began to untuck his shirt before starting to button it down. He moved slowly and deliberately, which added to the excitement "Have you found a lot of nice dick since you've been out here?" He asked me this in a casual manner that was extremely exciting.
"Not as much as I would have liked, I guess." I told him. After unbuttoning his last button he pulled off the shirt and then proceeded to pull his white undershirt over his head, revealing an elderly but fit body beneath. Moderately hairy and tan, with some sagging skin indicative of having lost some weight over the past few years. It struck me how this was by far the oldest guy I'd ever been with, and I could feel to my core that this was going to be a hell of an encounter. I was incredibly turned on.
Dom paused for a moment after his shirt was off, and I stood up and stood in front of him, looking down at him as I reached out for his pants and started unbuttoning and unzipping. I could see a pair of white briefs below. I helped him pull down his pants and dropped to my knees in a single motion. As he stepped out of his pants, I pulled down his briefs to reveal an impressively thick cock, about 7" long. Dom was extremely hard.
"Still got it." dom said in reference to his age and virility.
I looked up at Dom with his cock in my hand, a few inches from my mouth "damn."
As I opened my mouth and moved towards his cock, I felt Dom's hand grasp the back of my head firmly but caringly, and move my head purposefully towards his cock as he thrust it towards my mouth. I got the sense that he wanted to really fuck my mouth, but that he was also concerned about not pushing things too far too quickly. I moaned in approval as he pushed my head and his cock entered my mouth, but perhaps it was unclear to him that I was giving him the green light. I wanted to tell him he could do whatever he wanted with me, I was so turned on, but instead I just got to the task at hand: pleasing daddy Dom.
"Oh baby, I can't believe I got a hot boy like you sucking me right now."
"mmmm"
"Fucking nice boy." He placed his hands on his hips and ass, and arched his back. He was impressively hard for a 70 year old. His cock tasted clean. I could feel my own cock getting incredibly hard between my knees, pressed against the floor.
I started by taking his cock about halfway in with deliberate bobs. I knew I could take his nice cock all the way in my throat without a problem, but I like to work my way towards that when I am pleasuring a daddy. I went relatively slow, occassionally pulling his entire dick out and kissing it or licking it. I started looking up at Dom as I sucked him, and he looked down at me. He kept placing his hand firmly on the back of my head and rubbing my hair as if he wanted to pull my head forcefully onto his cock but he was afraid of unleashing something that would scare me off. Shame.
I tried to encourage him by moaning more onto his cock as he held my head and by starting to work his cock down to the shaft as I looked up at him. His cock was seriously fat and long enough to punch the back of my throat when I pushed myself down all the way on his cock. Dom had this incredibly hot way of talking to me in this calm, firm, and excited voice about how hot I was and what I good job that I was doing that really turned me on.
To show my enthusiasm and to disabuse him of the notion that he needed to be gentle feeding me his daddy cock, I started to force my mouth and throat down to the absolute base of his cock. This made me gag a little in response, but I was able to take it.
Dom felt emboldened by this. He grabbed the sides of my head more tightly and began to thrust his hips forcefully, never letting his cock all the way out of my throat. This made my eyes water.
He pulled his cock out of my mouth momentarily. Spit covered his veiny elderly specimen. There was spit dribbling on my face. He put his hands on chest to move me off my knees and onto my butt. He kept guiding me so my back was against the bed.
He looked down at me adoringly as he grabbed my ears with each hand and put his cock back in my mouth. "Daddy likes this" he whispered just before started jackhammering his cock in and out of my throat as he pumped his hips and also pressed my head back against the side of the bed.
I was so incredibly turned on. I started to see stars a bit as he pumped long and deep enough to actually cut off air. The playful gags of before turned into real involuntary responses to the assault on my esophogus.
Dom started to talk some sort of shit to me, telling me to give him my fucking throat and that he knew i was a faggot. I was sitting with my arms at my sides and my legs stretched, and I reached for my cock and it was rock hard.
My eyes were watering and I was starting to drool and spit. After about 2 minutes of nonstop high capacity pounding Dom pulled his cock out and started to shoot. The first rope hit my nose and splattered down towards my mouth. I was so turned on. Unexpectedly Dom gave my face a hard slap, maybe 7 out of 10'intensity. My ears started ringing and Dom unloaded what seemed like 15 bursts of cum on my face.
As he got done cumming he had his hands on his hips and his eyes closed, face turned up. He grabbed his 90% hard hog with one hand and grabbed the back of my head with the bother. He took a significant scoop of the cum covering my face up with his cock and shoved it in my mouth and groaned.
"Good bitch" he said and he walked off to the walk in bathroom across the room and closed the door. I heard him start the shower. I contemplated jerking and busting a nut as i sat there mindlessly scooping his cum off my cheeks and nose and into my mouth.
I got up after a minute and left...