How I (30) finally had my first time with a man (57) [MM]

For some background info I’ve always been submissive and interested in BDSM since I was about 18, I’d have considered myself to be totally straight up until maybe a year ago. I’m part of a popular hookup site in the UK and frequently get unwanted messages from men regarding my submissive tendencies that are clearly displayed on my profile – I’m interested in being pegged and teased. One of those messages came through three or four years ago…
A much older man than myself, wanting to know if I was interested in being ‘milked’. Of course I was interested in being milked but not by a man. I looked at his profile out of curiosity. 30 pictures on his profile and they were ALL the same, a man on all fours on a black leather sofa or seat (cliche!) – a toy in his ass and a puddle of cum underneath a very veiny lubed up cock that was bound with a black cockring and ball stretcher. This man was prolific. Each photo had the persons age and sexuality underneath with most of them defining themselves as straight or curious. The toys inside them ranged from dildos of varying sizes to butt plugs and massagers. Yes, I was interested, and I was kind of envious of all these men but… men don’t do anything for me.
Flash forward 3 years and I’ve somewhat got a curiosity about men over the last few years. I’m absentmindedly scrolling through this website and come across his profile. It’s almost exactly the same in regards to pictures, but obviously more of them this time. Videos now too. I watch a couple of them and they make me so aroused, I get off to them and log off. About a week later when logging back in I have a message in my inbox. It’s him… he’s seen the notification that I’ve viewed his profile. He wants to know if I’m interested, basically the exact same message he sent previously. ‘Maybe’ I reply. He comes back telling me what he likes, how he can accommodate my kinks. His USP is that I don’t have to know it’s a man doing this to me, I can be blindfolded if I like. We chat some more, and I’m somewhat resistant to the idea but reply to every message. I go back to look at the videos again and now I’m horny.
He says he gets a lot of men that are nervous and it’s alright. I guess I am nervous, very hesitant but very horny and I STILL can’t stop looking at the videos. He asks if I’d like to come round to his house for a chat. My hands are shaking as I agree… what am I doing? I tell myself it’s just a chat, see how I feel about it all and about him. I can always just leave if I’m uncomfortable. I feel like my dick has made this decision for me, or maybe my ass, who knows which one of them is in charge here.
On the day of the meet I am an absolute bag of nerves. I strongly consider cancelling with a polite message, or just block and ghost. But every time I go to his profile I’m watching the videos again… ugh. I tell myself it’s just a chat to calm myself, no commitments only a chat. I notice that all the boys have very little pubic hair, so I give myself a trim and a little veet action (be careful). I’m admiring my newfound smoothness in the mirror and wondering to myself if he’ll like it. Fuck. Just a chat just a chat just a chat.
I drive to his house, my mouth is dry from nerves and I take a wrong turn twice because I can’t think straight. I pull up, get out and walk to the door without my knees giving way. As I knock I realise that at no point have I asked what he looks likes… shit what if he’s really ugly? He answers the door and he’s a lot taller than I expected. He’s very stocky, kind of average looking. He introduces me and I walk inside. I notice that I’m shaking a little as I sit down. Just a chat, just a chat, just a chat.
He’s good at small talk and makes me feel comfortable, after a little while I relax and he offers me a drink of water, which I absolutely gulp down like an idiot. He laughs and asks if I want another but I politely decline.
He sits forward in his chair. ‘So…?’ he turns his palms over as if to ask the most obvious question. He begins to talk about the pictures on my profile, he’s complimentary about my body. I thank him very awkwardly. He asks me what I like about anal. Very straight and to the point. I tell him it feels good. Duh, he knows that but I can’t think of a better answer due to nerves. Just a chat. I try and relax and elaborate on my answer. He asks what I like about being a submissive, all of my interests. I try and give the best answers since it’s in both of our interests. He tells me he likes good boys, ones that are so good they will even go with a man when they’re not necessarily interested in them. Good boys that are placid and will let him play with their bodies, he likes to tease them, make them desperate before he lets them cum.
I can feel my heart rate increase again, I like what he’s saying but I try and play it cool. He’s being more direct now and I’m sure he can sense that I’m a little aroused. ‘Do you like being a good boy?’ Fuck. ‘Yes’ I reply instantly, accidentally a little too eager. He tells me that eventually I can call him Sir if I ever feel like it. ‘Yes, sir’ I reply immediately and he laughs a little. ‘I didn’t necessarily mean now.’ I apologise, a little flustered and he tells me that it’s very much okay.
He asks me if I’d like to see his toys and I agree. He drags out a large brown box from underneath the sofa. Only then I realise it’s the black leather sofa from the videos and pictures, I’d been so nervous before that I hadn’t seen. I think about the videos again and I can feel my cock starting to get hard. I think I want this.
He opens the box and reveals a mass of toys. All different colours and sizes, tonnes of them! I have never seen so many toys. I put my hand in and have a root around, he’s telling me about his favourites. I must look like a kid in a candy shop, pretty sure my eyes have lit up at the sight of this box. ‘How are you feeling?’ he asks, with a look in his eye. ‘Good’ I reply quietly.
‘You mean ‘good, sir?” he asks firmly. I quickly correct myself and he laughs a little again.
‘How would you feel about coming back one day to try some of these out?’
I nod. ‘Yes please’
‘sir’ he adds.
‘Sorry, sir’ I quickly reply. I tell him that it’s a little overwhelming
He asks me to choose my favourite three. I get down on my knees to look properly at all of the toys. I pick out three. One smallish plug with a gem on the end (you know the type), one medium sized realistic looking dildo and a prostate massager. I place them in his hand and he puts them to one side. I’m extremely excited by this point and can’t stop thinking how they might feel inside me.
He tells me he has some demands for playing. He pulls out the cock ring and ball stretcher from the photos and asks me if I’d be okay wearing it. ‘Yes, sir’. He wants to know if I’m okay for him to film/take pictures without my face in. ‘Yes, sir’. He would like me to trim my pubic hair as much as possible, he enjoys smooth boys. ‘Yes, sir, I did that this morning for you’
‘This morning?’ he asks very interested. I blush a little and nod. ‘I thought you just wanted a chat?’ he asks again. I’m a little flustered ‘Well.. yes but, just incase, I mean, you never kn-‘
‘Would you like to show me?’ he asks firmly. ‘You can say no, remember’ I nod a little nervously. My cock is now pushing against my jeans. ‘How far would you like to go?’ I can feel my face turn crimson, I want this but I’m still scared. ‘All the way?’ he asks. I nod again. He runs me through safe words and asks me the finer details, what I’m okay with and not okay with. I agreed to anal play, spanking, dirty talk, humiliation. I didn’t say no to anything. This was really happening.
‘Take off your clothes’ he said. I begin to pull off my t-shirt and he leaves the room, by the time he comes back I’m completely naked. Exposed, vulnerable, horny. He has come back in the room with a large bottle of lube and a towel. He compliments me and asks me to turn around to face away from him. ‘Now get on the sofa, bend over for me.’ This is it, no foreplay, just straight to the point. I like that. My heart is beating so fast, I can feel the cool air from the window brushing over my now exposed body. ‘Blindfold?’ He asks. I shake my head. I can hear the bottle of lube being opened and then the mild shock of cold lubricant on my now exposed hole, running down my cheeks and down to my balls. This doesn’t feel intimate, it almost feels like a medical procedure. The feeling of the ice cold lube is taken away by the warmth of his hands. He’s oiling up my whole ass, my thighs, my balls and my cock. Feeling his large hands on me drives me crazy, my cock is twitching and my mind is racing. His fingers work their way inside me with little warning and I gasp, my ass clenches around his finger and he moans. ‘Tight little hole’ he remarks. I don’t say a word, just stay still ready for whatever is coming next.
His finger slides in and out, slowly at first. He spanks me and I arch my back instinctively. He hits me again, harder this time, and then a further three times. My cheek stings and he’s still sliding his finger in and out of me. Completely using my body. He works his way up to three fingers and then takes them out. I feel him grab my balls tightly. This is like nothing I’ve ever experienced, I’m just staying completely still, I’ve fully submit to him and he’s using me. The cock ring slides over my cock, and then my balls. It’s tight, but it feels good. I can feel my cock throbbing and bouncing in time with my heart beat.
I feel him slide in the dildo I’d previously picked out. I let out a moan, this feels incredible. He slides it in and out of me with increasing pace, the only noise in the room is the sloppy sound of this dildo going in and out of my lubed up hole. I can feel warm lube dripping down me.
He takes my cock and begins to stroke. Slow, firm strokes while he fucks me with the dildo. I am a moaning mess, my brain is nearly overwhelmed with the feeling. He hasn’t said a word to me in ten minutes. He’s just systematically toyed with my body. He pushes the dildo deep inside me and I hear him get up. ‘Stay’ he says.
He comes back and I hear the sound of the bottle of lube open again. The feeling of cold lube slowly slides down my throbbing cock and I feel a new sensation. Something surrounds my cock. It feels incredible. I look underneath me and see that he’s grabbed a blue cock sleeve of some kind. It feels ribbed. I’m immediately on the edge of cumming. I’m moaning and writhing a little while he holds the dildo inside me and milks my cock. I tell him I’m about to cum and I expect him to stop. Instead he speeds up his stroking and applies even more pressure to the dildo. I lose it. I cum so hard that my body is shaking, my knees slip a little and he holds me up. I can feel my ass squeezing out the dildo with each pulsing orgasm.
I collapse on to the couch exhausted, I can feel the puddle of my own cum underneath me but I don’t care. ‘Thank you’ I gasp. He pulls the dildo out a little, and then back in me. I moan. It feels so good despite cumming just moments before. I can feel him scoop up some of my cum and then stroke my cock. I’m so sensitive and jump a little. He pushes down on my ass and strokes me again, I whimper. He repeats this for a few minutes, the cock ring refusing to let my hard cock turn flaccid. Eventually I’m not as sensitive and he senses this and begins stroking again, this time with just his hand. My cum covered cock barely lasts two minutes before it erupts again. He spanks me and then removes the dildo. I get up slowly, legs like jelly. I look at the sofa and it’s a complete mess. My cock is covered in lube and cum, still semi-hard because of the cock ring. He passes me the towel and then leaves the room. I clean up as best I can, put on my clothes and he comes back in. I thank him and he thanks me. I left to go home and haven’t stopped thinking about it since.

Source: reddit.com/r/gonewildstories/comments/u7tc0a/how_i_30_finally_had_my_first_time_with_a_man_57