From Ruiz: Gee I don’t know why you’re feeling cruddy about yourself when you’ve given yourself permission to be the happiest man on earth.
From Alan: Rub it in, asshole.
From Ruiz: Now you’re calling me an asshole.
From Alan: I mean it affectionately, and you know it.
From Ruiz: But you still feel crummy.
From Alan: I feel like a shit with an erection.
From Ruiz: Ha.
From Alan: Yeah, I’m a funny guy.
From Ruiz: But you’ll still meet me.
From Alan: “A person’s a person no matter how...”
From Ruiz: What.
From Alan: Dr. Seuss.
From Ruiz: I’m not that young and I’ve always hated his books. I thought they were stupid.
From Alan: Wait till you have kids.
From Ruiz: No way.
From Alan: You never know. These days, you could find a nice guy, marry him, and adopt – even in Iowa.
From Ruiz: Not gonna happen.
From Alan: You’re twenty-six. You never know what’s gonna happen. That’s one of the great things about being twenty-six. Along with your dick being hard all the time.
From Ruiz: Ha. Though the most important thing you’ve said is that you’re gonna meet me.
From Alan: Cutting right through my bullshit.
From Ruiz: You used to be a gentleman. It’s one of the things I liked.
From Alan: Heavy on the “used to be.” But not so heavy I’ll get pissed off.
From Ruiz: Ha.
From Alan: You’re just having a ball here, aren’t you?
From Ruiz: Ok - I’ll try to be serious.
I can do Saturday morning.
From Alan: What time?
From Ruiz: I like the idea of staying overnight. Like the idea of drugging myself a little and sleeping in my t-shirt and torn briefs and tying my ankle to the leg of the bed. And I like waking up in the dark.
From Alan: I don’t like the drugs. You never know how much you’ll take.
From Ruiz: It’ll just be over the counter stuff - a baby sleeping pill or something. I’ll be careful.
From Alan: I still might not be able to wake you in the morning – not as much as you’d like.
From Ruiz: Then it’ll seem even more like a dream - which’d be great.
From Alan: I don’t like drugs.
From Ruiz: Ok, no drugs dad, I got it. I’ll have a couple of beers before I go to sleep. Is that alright.
From Alan: Now you’ve got me laughing at myself. And I know you’re not one of my students, and I don’t mean to treat you that way.
From Ruiz: You’d lose your job.
From Alan: Don’t. Go. There.
From Ruiz: Ha.
From Alan: How high are you?
From Ruiz: Not high at all. I had a few beers when I came home to let me celebrate.
From Alan: For trapping a moron?
From Ruiz: An imaginative moron. Want to jerk me off.
From Alan: Are you gonna expect that every night?
From Ruiz: Well you set the bar.
From Alan: Which you quickly obliterated.
From Ruiz: And your change of plans was a nice surprise.
From Alan: I didn’t expect it. Didn’t expect last night, either. You kind of showed me for the rat I am.
From Ruiz: Stop beating yourself up. It’s nothing I meant to do - nothing planned and plotted. The whole Iowa City thing occurred to me when I woke up this morning and I more or less wrote it as I thought it forward.
From Alan: What brought it on?
From Ruiz: Oh come on. Everything that happened last night. The way I felt afterward. The way I felt this morning.
From Alan: You’re still sure of that? After a day of rational thinking?
From Ruiz: Well it was just this morning. I’ll re-read what I wrote at some point. But yeah I’m sure. I want to see you.
From Alan: It’s just something of a reversal – almost completely dropping your fantasies. As big a change as my own.
From Ruiz: Yours is more interesting.
From Alan: I’m assuming I’ll stay dressed.
From Ruiz: Most likely.
From Alan: No overt sex. No cheap hook-up. Just you following instructions.
From Ruiz: Correct.
From Alan: We shouldn’t need to text or talk once I’m in the room. You seem to like silence.
From Ruiz: Whatever’s more erotic.
From Alan: I can’t remember if the hotel room doors can stay unlocked. Or if you’ll have to open it when I knock.
From Ruiz: I want to be in bed when you come in. If I need to I’ll figure out a workaround so you can push the door open. But definitely silence and no electronics.
From Alan: I’ll need a little light.
From Ruiz: It won’t be black. Your eyes’ll adjust.
From Alan: Possibly.
From Ruiz: Would you maintain distance then and not remove articles with your hands.
From Alan: No distance needed. I’ll very slowly strip you. Or point.
From Ruiz: What do you mean.
From Alan: If I need you to move. Or touch yourself in a certain place.
From Ruiz: I see.
From Alan: I’ll want to get in contact with your body first and have you used to my doing that. I may slip behind you against that headboard and have your back against my chest. Explore you with my hands.
Are you OK with that? An alternative would be me motioning you to lie flat, then sitting beside you on the bed. But from behind and against you seems more erotic.
From Ruiz: I hadn’t considered that. I’ll have to think.
From Alan: How long do you want your glasses on?
From Ruiz: If we’re not texting, they won’t be on.
From Alan: I’d like to see you in them though. I’ve never thought of you that way, and I like guys in glasses – sometimes naked guys. They could be the last thing that goes – before your shorts.
From Ruiz: I just use them for computers. And reading. They’re drug store.
From Alan: The other thing is it’s virtually impossible to rip a T-shirt. In movies, they’re rigged. And Henleys would be worse. They’re usually thicker.
From Ruiz: If you end up behind me you can lift it off.
From Alan: Then I can’t use it to tie you. If you still want that. In your imagination, how are your wrists restrained?
From Ruiz: Over my head. Like you told me to when I was fucking the mattress.
From Alan: OK.
Also, I thought you were pretty protective about your chest. Will the light be dim enough, or should your Henley come off just before your shorts?
From Ruiz: Any of it sounds great. Though I think the order of clothes should be Shoe Shoe Sock Sock Outer shirt Partially unsnapping sweats Undershirt Sweats Glasses Briefs
From Alan: When do you get tied? After your briefs are off?
From Ruiz: I’m answering your questions as you ask them but don’t feel too rigid. As my clothes come off they can be used against me.
From Alan: Good, because there’s going to be a lot of exploring. If you hate something, simply shake your head.
From Ruiz: The briefs are hopefully the last to go. After a long time.
From Alan: Unless something happens spontaneously.
From Ruiz: Agreed.
From Alan: And I won’t let you masturbate till the end. And bring your lube. And go back and read what you sent me this morning and tell me if you have changes.
From Ruiz: Alright.
From Alan: A couple more questions: You’ve mentioned being interested in dark fantasy – is that where the restraints come in? And does masturbating in front of me seem like pleasure or following instructions? And have you ever done anything similar to this, and were there parts you’d want to improve? Or liked best?
From Ruiz: I’ve never done anything like this before.
Anything you think of is fine.
It’s impossible to predict everything.
And I understand my fantasies don’t exactly correspond.
As to the masturbation question - note that I never use that word. I just spoke of “without restriction.” So I think the answer to that depends on what you find more arousing.
From Alan: Your masturbating in front of me came from an earlier fantasy. I wondered if you were still interested.
From Ruiz: Oh, I forgot - thanks.
The restraints came from the idea of a possibly torn shirt.
Or a shirt going up my arms and accidently/purposely restraining my wrists.
And keeping my hands confined while yours are all over me.
From Alan: Got it. Thanks. Though even after a couple of hours, I might not know your body well enough to get you off – not the way you’d like. And I won’t ruin your orgasm by insisting on doing it for you.
From Ruiz: That makes sense. But you have the run of my body and the ability to command anything I do. And if you decide to wreck my orgasm that’s your choice.
From Alan: That’s nasty.
From Ruiz: Maybe I’d like it.
From Alan: Like fucking the air?
From Ruiz: Yeah - in frustration.
From Alan: It might be more fun to watch how you masturbate and then try it on you myself. Better for both of us.
From Ruiz: Your call.
From Alan: Is the idea of writing all this already giving you pleasure?
From Ruiz: It was intense this morning. Lower now.
From Alan: Do you think that might change again? That’d be fine. You just need to tell me.
From Ruiz: No, it’s lower now cause I’m in bed and relaxed after a long day of work conversations.
From Alan: You’ve just suddenly opened a lot of possibilities – things I didn’t think you’d be ready for. Not for some time.
From Ruiz: Like.
From Alan: Like allowing in some light. And actually having your clothes off – especially your shirt – not just in some fantasy. And the direct contact.
From Ruiz: The light will probably be a cracked bathroom door - so not that bright.
And I’m getting more used to being naked. You’ve made that ok.
And I really need your hands on me. I want them in all my secret places.
From Alan: You’ve mentioned your mouth being an erogenous zone. With fingers? Kissing? Is that still too intimate?
From Ruiz: Fingers are fine. We’ll see about kissing.
From Alan: You also mentioned a sensitive place on your butt. Between your cheeks? You only mentioned it once.
From Ruiz: Yes - at the very top. I can only reach it when I’m on my stomach and I’m usually on my back.
From Alan: In our joint fantasy, when I had one hand on your mouth and the other on your butt, you mentioned hitting both your erogenous zones
From Ruiz: Under my arms and the crease on my leg are still the strongest. You’ll have to see.
From Alan: OK. Are the torn shorts loose enough for me to touch your balls?
From Ruiz: Absolutely.
From Alan: I’m not sure you’ve mentioned your nipples. In some guys, they’re sensitive and others not. And does tickling arouse or annoy you?
From Ruiz: Somewhat arouse. Chest - it depends.
From Alan: Do these questions arouse or annoy you? I don’t mean to be giving you a physical. Just trying to avoid guessing in the dark.
From Ruiz: They neither arouse nor annoy. How do I compare to other guys you see.
From Alan: I told you, I don’t see many anymore. A very occasional old friend.
From Ruiz: Then other guys you’ve seen. How old and how fit are they - if you don’t mind me asking.
From Alan: Most have been much closer to my age, and they all have very similar bodies. That’s less my preference than how we all take care of ourselves now. I’ll know more about yours on Saturday morning.
From Ruiz: Ok.
From Alan: Does the thought of me with other guys arouse you?
From Ruiz: Yeah, some, or I wouldn’t ask.
From Alan: Are you planning to masturbate before Saturday?
From Ruiz: You know I don’t really plan.
From Alan: Double checking.
From Ruiz: What’s near the top of your anticipation list.
From Alan: Mainly being in the room with you. Knowing we have time and the freedom to play. That alone could sail me through tomorrow.
From Ruiz: Your hands gradually unsnapping my tear-aways. The sound of each snap reluctantly giving in.
From Alan: I never would’ve thought of that. I’ll have to remember not to shortcut your fun.
From Ruiz: Appreciated. Drawing out my strip is extremely preferred. And your hand staying on the front of my briefs for a very long time.
From Alan: Everything will be properly slow. I’ll be in no hurry to leave. Your body and my time limit will probably give out before our imaginations. And you can place my hands as well as my placing yours. No words needed.
From Ruiz: Understood.
From Alan: I’ll explore other places, too. But the front of your shorts will be home base.
From Ruiz: Good.
From Alan: Now go to sleep, kid, and I’ll try to do the same. You have the advantage of being able to touch yourself – freely. Don’t underestimate that.