Obey - 2. Chapter 2 -- Obey

From Obey: Good morning, Sir. This is my 4th day of chastity. I’ve attached the 4 pics you requested. The 3 of my dick I took this morning in the john at the office because I lock my chastity device in a box in my desk. The pic in my Sunday suit is a couple years old and it also shows my partner. I said I wouldn’t do that but the pic’s already on Facebook so I could say you found it there. Except you don’t know my name. You can see my partner’s pretty great looking except for his ears and he has a good sense of humor about them. He also has great hair – thick and dark. Mine’s always been lighter and it started thinning in my 20s. So for 10 years now I’ve been keeping it shaved. People say I look good this way especially since I keep my beard short too. The big difference is my partner’s 4 inches taller. That’s less obvious when we’re dressed up ‘cause of my good shoes. I told you about that. Also I really don’t know the answer to your question about why we stopped having sex all the time. There’s nothing that would stop me from having it every night and I told you I love looking at his body. Sometimes I start trimming my beard when he’s in the shower just so I can be there when he comes out. But we’ve been living together for 9 years and we knew each other for 2 before that – since I was 27 and he was 29. And we didn’t start out this way but we’re both pretty much bottoms now. When we have sex, I suck his dick and he sucks mine. I’d like him to fuck me ‘cause that’s what we used to do, but he says he doesn’t enjoy it much now. I think it has something to do with cumming. It takes me a while with a dick up my ass and I think he worries about getting soft. He grabs my dick and tries to jerk me off but I don’t want to cum that way. I love his body moving against mine, whether it’s on top or behind. And I’ve never really thought about fucking him because I don’t get off that way. Also he won’t initiate sex and almost never has and I can only get put off so many times before I quit. So sex is pretty spontaneous and always comes as a surprise. Other guys say I’m lucky that it doesn’t seem routine so maybe I’m being greedy. And my partner’s a great guy! I can’t tell you how lucky I am to have found him and I’m grateful everyday. And maybe ‘cause we’re not having sex all the time, I’ve started to need kink. You can pretty well pick any kind and I’m good to go. At first, I thought I was exposing myself just to prove I still had a dick. But the truth is I’ve always liked being naked, indoors and out. I hope that’s enough, Sir. I know I’m not stupid but you really made me think about things.

From Alan: You’re definitely not stupid, and that’s a great explanation. Thanks. I’m embarrassed to have asked you for photos since you’re even more naked when you write. But the photos are good, and you deserve a reward. Since I can’t magically make your partner have sex with you tonight, I’ll ease up on your assignments tomorrow.
Also, try sending me at least one photo a day with your message. And because there are some nights I don’t get online, you may have to decide what to send and what to write about. But most of the time, you’ll have instructions. For tomorrow, for example, dig through your scrapbooks and send me:
A picture of you before you were 10.
A picture of you in high school.
One in your 20s.
One just before you started to shave your head.
And explain each photo. If you can’t get these photos, then come up with 4 other pictures of yourself. You can take them tomorrow, or they can be things you have around.

From Obey: This is my 5th day of chastity, Sir, and I don’t want you to go easy on me because I can do what you want. The point is to push me hard. Here are the 4 photos. I scanned 3 of them from my Mom’s scrapbooks when she and Dad were at work and the last one I had in my computer. Also, it’s only been 6 years that I’ve been shaving my head. I thought it was longer. But I kept my hair very short for years until the day I went in and told them to cut it all off. As for explaining the photos:
1. 3rd grade, cropped out of a classroom shot. That’s why I’m sitting at a desk.
2. Senior graduation pic. Obviously retouched and probably better than I ever looked. But definitely cute.
3. College graduation party. Still full head of hair but you notice I’m the shortest one in my group. Even the girls were taller.
4. This pic was hard to find. I wanted one that showed how thin my hair got before I cut it short and I wanted to show how tubby I started to get after college. That’s ‘cause there are always snacks in the office. The women bake cakes and cookies and pies and bring them to work to share. I was never really fat, just round, which made me look cuter. I think that’s when I started growing my beard. But it just made my face look rounder, especially since I was wearing it full. Then I started dating a guy in Atlanta. It’s an hour’s drive and I did it every Friday night and came back late on Sundays. But it was worth it ‘cause he showed me a lot. I worked out with him on weekends and he took me to a place that trimmed my beard really well. They were the ones that convinced me to cut my hair short too. If I was 6 foot tall, I would have been really hot. Still, I kept the pic with the bad beard and the thin hair and too much weight to remind me I never wanted to look like that again. I hope my partner’s never seen it because he’s mostly known me how I look today. And I didn’t let too many people take pics of me when my hair was going.

From Alan: Again, thanks for your honesty and for the photos. And, yeah, you look much better today than you did with the full beard and the thin hair. I didn’t notice the weight so much because that’s a head shot, and with your beard, I can’t tell how round your face had gotten. Also, you never look short in your photos with no other people around. But the one from college puts that in perspective. As for the kink: I’ll work toward that soon. First, let me get to know you better. And the more you tell me about your dislikes, the more I’ll be able to play into them. So your messages are really useful. Tomorrow’s assignment is a free shot. Send me any photo you’d like. I don’t care if it’s of the president. Though making me laugh is always good.

From Obey: This is my 6th day of chastity, Sir, and what you say is interesting because it always makes me think. The problem is that I don’t know what I dislike because I don’t have that much experience. When I gave you that list and you said WHOA!, I’d never done most of those things. But I see guys put them online all the time and I see pics of guys doing that stuff. It doesn’t matter if the guys are hot – it’s more that they’re letting themselves be used. And they can’t object because they’re tied up or blindfolded or gagged. And the fact that they’re letting other guys post their pics gets me really hard. It’s why I don’t look at porn sites too much when I’m out of chastity – I cum too easily. So I really need to think about things I hate. One reason the guy in Atlanta stopped seeing me was ‘cause he said I was too vanilla. And I probably was though I was already 26. The other reason – and this was something I could never do anything about – is he said he liked tall men. He said it let guys know he wasn’t just interested in cute boys. I thanked him for the compliment and told him that I never thought of myself as less of a man because I was short. But it didn’t change anything. Still, he was great for me in the 2 years we were together and we’re still friends. And here’s today’s pic. I saw it online and it made me laugh so I hope it makes you laugh too. Weekends are usually hard for me to get self pics because I spend a lot of time with my partner and friends. My brother and sister live nearby too so we all get together with their families. But I’ll do the best I can.

From Alan: Again, what you tell me is far more interesting than any photos I request, but, yeah, the one of the naked guy painted to blend in with the brick wall made me laugh. Especially with his unpainted little pink dick standing out. And would a Monday through Friday schedule work better for photos? Weekends, you can just send messages. So no photo tomorrow, but answer this question. How often do you come in your sleep?

From Obey: Sunday, one full week of chastity, Sir. And yes that schedule works better for pics. And I keep meaning to tell you that not cumming really fucks with my head. Right now, after not cumming for 7 days I’m so horny I’d do almost anything. It also messes up my sleep. Sometimes, I have to go downstairs in the middle of the night and strip in the backyard because it’s like taking a cold shower. I’d take a real one but I’d never run water at night and risk waking my partner. As for cumming in my sleep, it’s not something I ever remember doing. I grew up sharing a room with my brother who’s 2 years older. So I never had the privacy to jerk off in bed. It was always in the john or the basement. Sometimes, I’d ride to the forest and do it there. The national forest is near my folks’ house and it’s 20 minutes by bike. That was also the first place I was naked outside – I mean for more than changing clothes or drying after a swim. Usually it was for an hour or 2 when no one was around. But I once managed to stay naked all day. That was amazing and I must have cum a half dozen times, I was so horned up. It was also hot because I had to hide when I heard people coming so I wouldn’t get caught. I didn’t have much privacy in college either though I wasn’t having sex with guys yet – I was too afraid of disease. But I don’t remember jerking off in the dorm. That’s dumb when you consider how horny I was. I’d sometimes go home on weekends just to get to the forest. And I hope I’ve told you enough for today, Sir, to make up for not sending a pic.

From Alan: You’ve told me more than enough, and you keep surprising me. But I’m curious about something: I’ve told you almost nothing about myself, so is there anything you want to know? What did Johnny tell you? Is there something you’re missing? And send me a new photo of yourself tomorrow, just to stay in practice. But I don’t care what the photo is or how old it might be.

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