Steve's First Adventure

Please ignore this story if gay sex or discipline isn't your thing. Nothing about this story is factual and forgive my writing errors, not a work of art, just a kinky story.

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My name is Steve and I thought it best to tell my story as a warning to others on how things you never expect can happen. I'm 28, 5'8", 140 lbs and in pretty good shape. No hard abs on display but in good shape from visits to the gym at least four times a week. I have always been naturally smooth and rather envious of those men who come across as more of an alpha male. Don't get me wrong, I get my fair shape of affection from the opposite sex. Haven't had many long term relationships but I have had a lot of fun along the way.

My job allows me to work from home and I really like that but it does make it harder to have interactions with fellow coworkers but there are good and bad things about every job. This job also allows me to keep my hair longer which I have always liked. My boss is great and enjoy our one on one meeting we have twice a month. He is older but a cool guy.

This job also means I'm on my computer a lot and like any other true blooded guy that means a lot of time on the internet. Like most of other guys, that means time watching porn. Admit it, you like it too. It became harder and harder for me to stay away from it and I spent a lot of late nights glued to the screen. After a while I found watching the normal stuff was getting boring and I started to start checking out the kinkier videos.

I ended up watching some videos where guys were spanking their wife or girlfriend and was surprised at how much I was attracted to that scene. Some of them got pretty extreme and the spanking were very intense and had to really hurt. I hate to admit it, but the videos where the girls ended up crying and begging the guy to stop, became some of my favorites. I know, probably wrong, but it was how it was. I was never spanked as a kid and could only imagine how it must feel. It had to hurt.

As I searched for more videos I ended up watching some with men spanking another guy. Usually it was an older guy with a younger guy. Some of the guys you would guess were gay but there were also some masculine looking guys having their ass worked over. Some of these spanking seemed to be even harder than the ones with the girl getting spanked.

Thinking back, I should never have started watching those and stuck with the one with girls being spanked but I had trouble staying away from the ones with guys getting spanked. I couldn't imagine how it must make a guy feel to be put over some guys lap and spanked, to have a man pull your shorts down off your ass and then spank you hard. That seemed so strange. My favorite videos usually involved an older man and a younger guy. The ones with two young guys just didn't entice me as much.

The videos usually continued until the young guy ended up sucking off the older guy and sometime being fucked by them. I usually stopped the video when the spankings were over. I'm not gay and the cock sucking and fucking wasn't my thing. Some of the men were definitely dominant and you could tell they enjoyed humiliating the boy while working them over. I enjoyed the videos where the guy was very verbal, calling the boy demeaning names, or making the boy admit that he was a fag or a wimp. I have to admit, the hottest ones ended up with the boy crying just like the girls in the other videos. How must that make a guy feel, to have another man make him cry like a little sissy boy?

I couldn't keep this stuff off my mind and started looking at the ads on craigslist that involved men spanking other men. I was surprised that most of the ads were from guys who wanted to be spanked. There were a few ads from men who were looking for boys to spank and some of them were pretty graphic and left no doubt that they were dominant men. I spent a lot of time reading ads from both the boys and men but never replied to any of them.

That changed one night when I saw this ad. 'Wanted: a boy in his twenties that need direction from a real man. I'm almost fifty and know what you bad little boys need. Prefer boys with no experience. They are always easiest to train. I know you want this boy. Are you man enough to answer this ad? I doubt it. You are probably another one of those pussy boys. Your loss boy. If I'm wrong, then email me boy.'

I couldn't get this off my mind. Did I really want to be spanked by another guy? I know it's not the same as sucking a guy or being fucked but it still seemed kind of gay. I guess if I made sure he knew I wasn't gay and was only interested in seeing what it's like to be spanked, it would be ok. I had to answer his ad just so I could stop thinking about it all the time so I emailed him.

'Hello. I read your ad and I haven't been able to stop thinking about it and you. I'm in my twenties, single, in good shape and want to make it clear that I'm not gay but the idea of being spanked does interest me. I have never been spanked, not even by my parents and have no idea how I might react to a spanking but want to find out. I was hoping maybe we could exchange a few emails and see what happens. Steve.'

The next evening, I received a reply to my email. 'First of all Steve, you will address me as Sir in your emails. I demand respect from my sub boys. Now as far as the rest of your email, I think you might fit the bill for what I'm looking for. I'm sending you a picture and expect one in return. Your picture will show you in nothing but tight white jockey shorts. If you don't have any go buy some, at least one size too small. If you can't obey this simple command, do not bother me further.'

His reply wasn't what I was expecting and made me very nervous, especially the picture part. I remember opening his picture and it showed a guy that looked to be over six foot tall and in good shape. He was wearing black leather pants, black boots, a black leather vest and leather armbands on both biceps. His chest had a light covering on black hair that matched his five o'clock shadow and his black hair. He definitely looked like men I had seen in the videos, dominant men.

My first thought was this guy might be more than I'm looking for. I had never really thought that much about how the guy would expect me to be submissive to him. I had only been thinking about what the spanking would be like and not how the interaction between us would be like. The picture part was especially scary and I knew it wasn't negotiable. What if the spanking hurt too much? Would this man stop if I wanted him too? His picture said no and that worried me. But his picture was hot and he was the kind of man I had fantasized about but could I do it for real or was I one of those he mentioned, a pussy boy?

I couldn't stop myself from going to the dresser and taking out an older pair of jockeys that I had outgrown. I stripped down and put them on and they were definitely tight. My cock was clearly outlined in the tight shorts. I got my phone and took a picture in front of my full length mirror. I held my phone in such a way that it blocked my face and stared at the picture. I could to this. I still wasn't committed and if it didn't go further than emails nothing bad could happen.

'Sir. I was glad to hear back from you and your picture was awesome. You definitely look like an alpha man. I have to admit, I'm very nervous about this but I would like it to happen. I have to ask you. What if it's too much and I want to leave? Will that be ok? I hope you don't mind me blocking my face in the picture but discretion is important. Hope you like my picture as much as I liked yours. Steve.' I sent him the email.

I must have checked my email a hundred times waiting for his response and had finally decided that he hadn't liked what he saw and I have to admit, I was disappointed. After three days, I finally, an email from him.

'I was disappointed in you, boy, but I will give you one more chance. I noticed in your picture that you have pubic hair. That is not acceptable, get rid of it. Only men have pubic hair. And no, blocking your face is not ok. It's pathetic on your part. You are willing to have me spank your ass but you are too much of a wimp to show me your face. Send me another picture and don't fuck this one up. Forget about your concerns on whether it turns out to be too much, I know what is too much, not you. Do not disappoint me again. Lastly, you will refer to yourself as Stevie. Steve sounds too masculine for you.'

Wow! This man didn't pull any punches. This guy didn't leave much doubt about what kind of man he was and how he feels about me. He tells me what he wants and he expects me to do it. I wonder if he is just testing me and doesn't really actually meet with guys but just likes to jerk them around on the internet. I had seen messages about guys doing that kind of thing. I knew I should have just stopped everything right then but I couldn't. The way he came across, while scary, was also very hot. I knew that I was going to do as told.

I stripped and went into the bathroom and checked myself out. My cock wasn't huge, around six inches, cut, but I hadn't had any complaints from girls I had been with. I picked up my electric razor and started trimming my pubes and cut them as short as I could. Then I filled up the tub with nice hot water and after grabbing my Gillette razor hopped into the bath tub. It took a while but I got all my pubes shaved off and I was totally smooth. I got out, dried, and checked it out. It looked so strange and I was surprised how it made me look more like a young boy. I went back into the bedroom and got the tight jockey shorts again and put them on and took another picture.

I remembered how I had kept checking my email for three days, waiting anxiously for a reply from him and that told me I had to do if for no other reason than to get it off my mind. I sent him the picture with this email. 'Sir, I'm sorry to disappoint you but this is all so new for me. I shaved off my pubes as instructed and sent you another picture. I hope this one pleases you. I will try harder to be a boy like you are looking for and not wimp out on you. I really want to trust you not take things too far. I do want to remind you that I'm not gay. Hope to hear back from you Sir. Stevie.'

I heard back from his the following night. 'Boy, you did much better this time. Maybe there is hope for you. You do have a nice body and hopefully the right mindset to go with it. You do seem rather homophobic but that's ok. I understand it would be hard for a boy to admit he's a cock sucking faggot. You will come to my house at 8:00 Saturday night. You will wear tight jeans, no socks, tennis shoes, white tshirt, preferable tight, and of course your tight little shorts. You will ring the door bell, then get on your knees facing the door and wait for me to come for you. If any of this is unacceptable, don't bother me again Stevie boy.'

I remember how I felt so panicky. This was it, would I do it or would I wimp out. The thought of meeting him was very scary but I knew if I didn't do it that I would regret it and have trouble stopping thinking about the whole scene. I needed to do it to just get it out of my system. I couldn't concentrate on work all week and had trouble sleeping thinking about meeting him and being spanked. I realized he had never mentioned anything about spanking me but had just been aggressive with me demanding the pictures and everything.

I will continue this story like what I experienced at the time.

I pulled up in front of his house. It was a nice house in an expensive neighborhood and that helped to relax me. Didn't figure someone too crazy would have a nice place like this. I had found a tight pair of jeans and tshirt and hoped he would be happy with the way I looked. I walked up to the door, almost nervous enough to be shaking, rang the doorbell and went to my knees. Thankfully his entryway set back from front of house and it would have been hard for anyone to see me. I must have waited over five minutes till he came to the door. I had gotten even more nervous, hoping this was his house and he didn't send me some stranger's house just to fuck with me.

'Eyes down boy. Crawl into the house.'

All I could see was the bottom of his black leather pants and boots and I followed him in. The tile floor was hard on my knees and was glad when we finally got to the living room and the carpet. He stood there in front of me legs spread.

'Why are you here boy?'

'I want you to spank me Sir.' It was hard to tell another man this and was glad that I didn't have to look at him.

'Trust me boy, you will be spanked. Now I want you to stand up and look at me.'

I stood up and looked at him. He was in the same outfit he had worn in the picture. He looked even more solid than he had in the picture and his stare was rather intimidating.

'I have to tell you after seeing you in person Stevie, that I'm surprised you aren't gay. I bet a lot of people think you are gay.'

'Well, I'm not Sir and don't appreciate what you said.'

'Don't get your panties in an uproar Stevie boy. You just look like a faggot to me, that's all. I know you claimed not to be gay enough times in your emails it made me wonder who you are trying to convince, me or you.'

'Sir, I'm not gay. I don't want to be gay and I don't think most people think that I am gay so can we drop it, please.'

'You are so sensitive boy. At least you said please boy, that's a start. Now undress. Leave your underwear on.'

I take off my tennis shoes, then my tshirt. I knew this would happen but it was still hard for me to take the tight jeans off. It felt so weird standing there in front of him in just the tight jockeys with him fully dressed. I put my hands down covering my crotch.

'Hands to your sides, boy. Look at you, so smooth, figured you might have a little chest hair. Did you shave it off?'

'No Sir.'

'I see. Lots of boys are like you. My favorites. It must be hard to think of yourself as very masculine when you can't even grow chest hair. I bet you don't have to even shave very often either.'

I found this rather demeaning but what could I say. 'I shave every couple days or so Sir.' He moved closer and reached up and ran his hand through my long hair.

'Nice hair boy, feels as soft as a girls. I wasn't surprised to see your long hair. It kind of confirmed what I thought about you when I saw your picture.'

'It's just the way I like to wear it Sir. It doesn't say anything but what kind of guy I am.'

'Sure boy, keep telling yourself that. I love the way your tight shorts look. Makes you look so young. Are you really 28?'

'Yes Sir.'

'You look much younger Stevie. I would have thought maybe you were twenty. Now take off your cute little panties.'

'They aren't panties Sir and the only reason I'm wearing them this tight is because you told me too,' I answer hoping to make the point that I didn't appreciate some of the things he was saying, especially the gay crap, but immediate thought about how it sounded like I was talking back to him.

'I've had about as much of your attitude as I'm going to take. Be a good little boy and go into the kitchen and bring back one of the wooden straight chairs that are in there Stevie.'

Oh god. I know what that means. I'm shaking as I go in and get one of the chairs and bring it back and set it down near him. He walks over and sits down on it.

'What are you waiting for boy? You know why you are here.'

'I don't know Sir. Maybe I'm not ready for this. I'm sorry but I think I should go.'

'You have ten seconds to be over my lap or I'm getting up and, trust me boy, you don't that to happen. Now get your ass over my lap boy.'

Reluctantly, I go over and lay down over his lap. One of his legs goes over my legs holding me in place and he pulls one arm up behind my back, not enough to hurt but enough to keep me from moving.

'I have known a lot of boys just like you Stevie. Confused about what they want and what they need. What can a man think about a boy that wants his ass spanked like he's nothing but a little girl? Do you see why I have trouble seeing you as anything but a little queer.'

'Please Sir, please let me leave. Please.'

'No boy. You came here wanting your ass spanked and that is what is going to happen. Now beg me to spank you ass.'

'I changed my mind Sir. Please let me go. OWWWWWW' His hand had hit my upper thigh hard. It really hurt.

'It hurts even more on the thighs boy. Now do you want another one there or are you ready to beg me to spank your sweet little ass?'

I can't believe how my thigh stings. I definitely don't want him to do it again so I do what I must. 'Please spank my ass Sir.'

'That wasn't so hard was it boy. Now I know you want it on your bare ass so you need to ask me to pull your panties down.'

It's all so much more intense than I imagined and much more embarrassing. 'Please take them down Sir.' WHACKKKK Right on the same spot on my thigh. 'OWWWW' Oh god, that really hurts.

'I think I told you to ask me to pull your panties down Stevie. Now are you going to do as told or do you need your other thigh worked on?'

'Please don't Sir. Please pull my panties down Sir.'

'Much better sweetie,' he says as he slowly pulls my shorts down to the bottom of my ass cheeks. 'Such a cute little ass. I bet a lot of girls wished they had such a pretty ass. I bet you get a lot of guys checking out your ass don't you Stevie.'

His hand caresses my ass cheeks. Then he hand comes down on one ass cheek. It isn't real hard but still stings. Then he starts spanking me and as he does, the blows become harder and harder till it really starts to hurt.

'I asked you a question boy,' he says as he stops spanking me. 'Tell me that you have a lot of men checking out your sweet ass.'

Oh god, it really hurts much more than I was expecting. I try to move but he holds me in place.

'Tell me boy.'

'I don't know Sir. I don't pay attention to whether men are checking me out or not. I don't care.' He starts spanking me again.

'Your cheeks turn such a pretty red boy. I like that. Now I want you to tell me that you like it when men are checking you out. I know several of my friends wouldn't be able to keep their eyes off a sweet little boy like you. Be a good little boy and tell me you love having men look at your ass.'

'Sir, I told you I'm not gay.' He starts spanking me hard again and doesn't stop till he has hit each cheek at least a dozen times. It's all I can do to keep it together. I know I was begging him to stop but he didn't.

'Tell me Stevie. Tell me how you love have men looking at you.'

'OK, OK, I like it when men check me out.' His hand comes down hard on my other thigh.

'I don't believe you Stevie,' he says as he hits the same spot on my thigh even harder. 'Convince me boy. Tell me how turned on you get when men are checking you out. I bet you even get hard when you see a man looking at you thinking you are a fag.'

I start sobbing making it hard to talk. I know what he is doing. I have seen it in the videos. He wants to humiliate me. 'Sir, I like it when they look at me, when they look at my ass. Sometime my cock even gets hard. I bet some of them think I'm gay.' I know if I don't answer like this, things will only get worse.

'I bet you check them out too. You look at their crotches don't you boy? You wonder how big of a cock they have,' he says as he spanks my ass several more times.

My ass feels like it's on fire. It's so much more than I was expecting and didn't know he would try and make me feel like he is doing. Sobbing louder now and I feel tears running down my cheeks. 'Yes Sir, I look at them and wonder about their cocks and what they are thinking about me.'

'What do you think they are thinking Stevie?'