First time with the antiques guy
This is a long story so I may have to tell it in multiple parts.
By the time I was about 19, in my second year of university, I knew I was, at least, bisexual. I had a girlfriend and was straight acting, but ever since I had stumbled on some gay erotica in my teens I had been secretly fantasising about men. I can still remember the rush I got the first time I read a gay story, about a cross-dresser who gets caught by his neighbour. He ends up getting fucked by the neighbour up against the clothesline while he's hanging out the washing wearing a lacy camisole. While I may have been straight during the day, at night under the covers I was jerking off to fantasies about men almost every night. It was like being two different people. At the time I used to drive past an antique shop on my way to and from campus. I was into vintage clothes and that sort've thing, and was desperate to seem cultured and cool, so one afternoon after classes I pulled in on my way home. I can't remember a lot about the store, but I remember it was a large, typically rambling antique store with lots of nooks and crannies. I also remember it was empty when I went in. As I was browsing, the guy who owned the shop started chatting to me from his desk. He was an older guy, probably in his mid 50s, taller than me, with a thick moustache and a bit of a paunch but in pretty good shape. Today we'd call it a dad-bod. Eventually he walked over to where I was looking at some old paintings and started talking to me about them. He started asking me questions about myself; just about what I was studying, things like that. We talked like this for a few minutes. He was obviously gay. His voice and mannerisms screamed camp, and the way he talked about the art we were looking at made it obvious he was cultured. I liked him. As we chatted, he mentioned what I was wearing - a pair of shortish denim shorts which hugged my thighs - and said something like "I have to tell you, I love your legs". I just sort've laughed it off and said thanks, but was too taken aback to say anything else. He kept going though, and said: "you must get a lot of attention with those legs, from girls... and guys." That last part was added almost as a question. I was totally flustered. I could obviously feel that he was hitting on me, and although I had fantasised about it a lot, I had never been flirted with by a man before. Picking up on my nervousness, he asked me, in a fairly light way: "I suppose you're straight?". I remember hesitating. Part of me wanted to say "NO, I'm actually desperate for cock, I jerk myself stupid every night thinking about it", but my nerves got the better of me. I think I muttered yes, said something about having a girlfriend, and made a hasty retreat. I was in a daze after it happened. For days, I couldn't stop thinking about the feeling of being openly pursued by this older man who clearly wanted me. In my late-night fantasies, I was always the bottom, the one on my knees or bending over, and having this man, old enough to be my father, objectify me like that sent me into a spiral of horniness that I couldn't shake. After about a week, I made up my mind that I would go back. I wasn't even sure what I thought would happen, but I made sure to wear the same pair of shorts. I was a pretty slim guy, something I was usually self-conscious about, but I also decided to wear a fairly tight, short white t-shirt which only barely covered my midriff. I was disappointed when I got there, though. This time the store was busy, and the owner was busy helping customers. I waited around for a bit, trying to act like I was looking at the stuff in the shop but really just hoping he'd notice me. After a few minutes, he did. I felt him notice my presence, and looked at him. He gave me the briefest smile, which I shyly returned. He looked over at me a couple more times before finally excusing himself and walking over. In a voice loud enough that the customers he was helping he could hear, he told me in a polite voice that he was tied up but if I came back a bit closer to closing time, he could help me with the purchases I was hoping to make. I can't remember exactly what it was - some furniture, maybe - but it was definitely a totally made up pretense. He was inviting me into a secret rendezvous. If I said I didn't know what he was talking about, he could say he had mistaken me for someone else. If I agreed, I was accepting his invite. I can still remember my heart beating in my chest as I said, my voice a little raised, that that sounded perfect. My cock was as hard as a rock as I left the store and got back into my car. I can't remember exactly how I killed the time. I think I drove somewhere and just sat in my car waiting. I kept telling myself I should forget the whole thing and just go home, but my horniness kept me there. Finally, about 15 minutes before closing time, I pulled up back at the store, took a few deep breaths and walked in. He was still serving a final customer when I arrived, and again I loitered around trying to pretend I was browsing. I remember watching as he walked out with the customer, locking the door behind him as he turned to me after they were gone. "You came back!" he said cheerily. Even though it was clear why I was there, he was keeping it light, which I appreciated. He told me his name, Rick, and I told him mine. We chatted again, this time about music because I had been inspecting some old LPs. I started to relax. "I'm sorry if I offended you the other day," he said eventually. I told him no, I just hadn't known what to say. He said something about remembering how difficult it was being my age. Eventually, he told me he had some more records from his private collection upstairs in his office if I wanted to look? I said yes, and he told me to follow him. He let me start climbing the narrow staircase first, and I still remember him making an audible grunt of approval as he walked up behind me, his face level with my ass. When we got into his cramped office I was somewhat disappointed to see he hadn't been lying. There was a big collection of LPs, some stacked, some displayed on a shelf. For a while we stood there looking at them. I felt frozen. My nerves, which had dissipated, were returning, but this time because I didn't know how or whether to make the first move. I need not have worried. All of a sudden, I felt his hand rubbing my ass. "You look so good in those shorts," he said, his eyes on me. Still looking straight ahead, I let out a little moan as I felt his fingers caressing my crack. "I got that impression, that's why I wore them again," I offered. And that was it, suddenly he was on me, pulling me to him, pushing his tongue into my mouth, and I was making out with a man. I remember thinking how surreal it was, but also how normal it was. Gay kissing was a lot like straight kissing! His hands were on my body and underneath my shirt, playing with my nipples, and I was doing the same, feeling his bigness and heft and swooning at the feeling of being taken by this big man. I felt like a girl and loved it. I could feel his hard cock against me as we pressed our bodies together and I started to grab at it, squeezing and pulling on it, he started guiding me down and I happily fell to my knees, undoing his pants and pulling them down to reveal his cock. It was fairly average sized, but bigger than mine and much thicker. I started to suck him off, not really knowing what I was doing but just basically copying what I'd seen in all the gay and straight porn I'd been watching. He was groaning, holding onto my head and pushing it down on him, subetly at first, before eventually he was fucking my mouth. I remember feeling turned on beyond belief that my mouth was being used by this old man. After maybe 10 minutes of this, he pulled his cock out of my mouth and pulled me to my feet. He'd stripped off his shirt and started kissing me as he pulled off mine, then undid the shorts that started all of this and let them fall to the ground. In just my briefs, he told me to turn around and lean against the desk. I did what he said, sticking my ass out, but in truth I was suddenly terrified. I had experimented a bit by myself, using fingers and a toy I'd bought in secret, but I wasn't sure if I was ready to get fucked in this cramped, cluttered office. Instead, he did something I had not been expecting at all, yanking down my briefs, falling to his knees behind me, and burying his tongue in my ass. Having my ass eaten for the first time was a feeling I can't really describe. I'm honestly not sure anything as hot has ever happened to me since. I remember letting out a big, high pitched moan as waves of pleasure washed over me. The sensations, where no one had ever touched me, were intense. It felt so hot and naughty. Until that point my own cock had been going hard and then soft, my erection tempered by the nerves I was still feeling. But as I pushed my ass back onto his moustachioed face, moaning and whimpering, i was suddenly hard as a rock again, and couldn't stop from jerking myself. All too soon though he stopped and stood, leaning forward and kissing my neck and asking breathily if I wanted to fuck. I was weak limbed and glowing from the rimming I'd recieved and just said "yes please". He walked into a small bathroom, leaving me leaning against the desk catching my breath, and after a minute came back out, this time with a condom and a tube of lubricant. "Always be prepared," he said laughing as he showed me the lube. I exhaled nervously and he said "I assume this is your first time?" I just nodded. He told me not to worry, that he'd guide me through it. I won't go over the whole thing, but it took some time. At one point, when it felt too painful, I told him maybe I wasn't ready, but he kept telling me to relax, that I needed to breathe. To be honest, looking back, he was quite insistent. Now that I'm older, and know more about consent, I would not condone the same behaviour. But to be honest, I loved it, and still love the memory of it. This pervy older man had unlocked something submissive in me. Finally, after what felt like an eternity, the head of his thick cock was inside me, stretching me out. It hurt, but in a good way. After leaving it like that for a moment to get used to it he slowly pushed further and further inside me, until he was about half way in. Slowly at first he started to fuck me, pushing further and further in each time until I could feel him bottoming out inside me. I was crying out in pain and ecstasy, letting him have his way with me. My own cock had shrunk, a little nub sticking out as he took my cherry. As he sped up he started talking dirty to me, telling me he knew a guy with a face as pretty as mine couldn't be straight, telling me he could tell I wanted it when he first cracked onto me. All I could do was moan as he had his way with me, shouting "yes, yes, yes". After maybe 15 minutes, just when the pain was starting to overwhelm the pleasure, he started to get wilder, pushing into me hard as he spanked my ass. All of a sudden he let out a guttural yell and I felt him pulsing as he emptied his balls into the condom. He collapsed on top of me, both of us sweaty messes lying on his desk. Me face down, him with his body pressed against me. After a while he got up and kissed me again. I sat on his desk and wrapped my legs around his body while we made out. He offered to go down on me, but I was too frazzled by everything, I knew there was no way I could get it up. We both got dressed and walked downstairs together. Outside the sun had set, and as he opened the door for me we exchanged one last furtive kiss and I was out the door and back into my car, my head spinning and my ass stinging. That was the first time, but it wasn't the last.