Text Messages From a Friend

I'm Nicki and recently I've been chatting a lot with a boy I like. He's really attractive and I've been flirting loads with him. He's clearly quite inexperienced with girls and he seems nervous around me. I'd always hoped it was because he liked me and recently we texted one evening and it was so sexy chatting with him and finding out he did in fact like me. This is how the text message conversation went: Me: Hey, what are you up to tonight? Him: Not much, just staying in, what about you? Me: Yep, same. Really bored, just watching TV. You doing anything exciting? Him: Not really, had an interesting dream last night though. Me: Oh really? Sounds intriguing, tell me more. Him: I'm not sure I should, it's a bit embarrassing. Me: Oh come on, I won't tell anyone. What happened? Him: Well you were in it. This really got my attention. Me: Oh I see. Tell me more... Him: Well it was a bit, you know. Naughty. Me: ha ha, you mean it was a sexy dream? Him: Well, kind of yes. Sorry. Me: Well it's not your fault what you dream about surely? Him: I guess not but it wasn't just the dream. Me: What do you mean? Him: I'm not sure I should say, I'm worried you'll hate me. Me: I'm sure I won't, tell me, what happened? Him: Well I woke up in the night right after the dream and I had, well you know... I knew what he meant but I wanted him to say it as it was really turning me on hearing him talking about this. Me: What do you mean? Him: Well I had a, you know, erection. I feel really guilty. Me: You shouldn't feel guilty for getting an erection, it's a very normal thing to happen. Him: I suppose, but I couldn't stop thinking about the dream and then I started thinking more about it and thinking about you being naked. I'm really sorry, I feel so bad and thought I should own up to you. This was such a turn on, knowing he'd thought about me like that. I wanted to probe and ask him more. Me: Oh I see! Well, I'm flattered you thought about me like that. But surely, that didn't help make your erection go away? Him: No it didn't. Me: So what was I doing in your fantasy? Him: Well I just imagined I was watching you getting undressed and having a shower and you couldn't see me. Me: And then what happened? Him: What do you mean? Me: Well, did you feel turned on by thinking about me? Him: Yes I did. Me: And what did you do about that? Him: I'm not sure I should say. You will hate me. Me: I promise I won't. Just tell me... Him: Well I had this incredible urge to, you know, touch it. Me: Touch your erection you mean? Him: Yes, I couldn't help it. I'd never felt anything like it before. Me: You'd never felt the urge to touch it before nyou mean? Him: No, never. I mean, I'd had erections before but this was the first time I'd felt this urge to touch it like that. Me: How did you touch it? Him: Well, just sort of rubbed it gently at first. It felt so nice. Me: Only at first? What happened then? Him: I can't say. I'm so ashamed. Me: Please don't be ashamed. Like I said, I'm flattered you think of me like that. I'm sure it's nothing bad. Tell me, what happened then? Him: Ok thank you. I'm not sure how to say it... Me: Did you pleasure yourself over me? Him: I just couldn't help it. I'm so sorry. Me: Don't be sorry. Not at all. That's really sexy and I'm flattered you thought about me while doing that. Was it your first time? Him: Yes, I promise I've not done it before. Me: It would be fine if you had. Its perfectly normal to masturbate. Him: It is? Me: Of course! I masturbate all the time. I really enjoy it and it helps me get to sleep as well! Did you have an orgasm when you did it? Him: Yes. Me: And I bet you fell asleep soon afterwards? Him: Actually yes, I did. Me: There you go, see. You shouldn't feel guilty at all, I do it most nights to help me sleep and I have fantasies too you know... Him: Really? Me: Of course! In fact, after what you've just told me, I'm doing it right now and all I'm imagining is your naked and erect body, pleasuring yourself.  Him: Oh wow. Im getting an erection again now! Me: Good, I'm pleased. I think you should go with the urge again and do what feels good. I'm definitely going to come soon.  Him: That's cool. I don't feel as embarrassed or guilty now. Me: Good. And nor should you. I've masturbated over you loads of times since we met and I certainly will do now. Maybe, if you'd like, we can do it together soon and I'll show you how I do it and you can see what I look like naked for real so you won't have to use your imagination. We did get together soon after this and I helped him lose his virginity and open up sexually. I showed him how I masturbate and had some amazing orgasms knowing he was watching me and getting aroused so much by it as well.