1. Becoming Melissa's Cuckold Pt. 01

    Date: 7/11/2019, Categories: Cuckold Author: GreyMatter, Source: LushStories

    ... her out. It was the first time that I'd ever asked a girl out on a date and I was incredibly nervous. There was a band coming to town that I knew Victoria liked. I got a pair of tickets and casually mentioned to her that my 'friend' backed out and I needed to find someone else to go with. "I'll go!" she said with excitement, maybe more for the band than me but it was a yes and that's all I wanted to hear! In the days leading up to our date, Melissa was drilling me with advice - what to do, what not to do, how to act, how not to act, where to go before the show, where to take her afterwards. It was like a crash course in dating. While I was absorbing everything that she was saying, it was also a bit of a reminder of how little I knew about dating. As the day of our date approached, Melissa brought up the subject of orgasm control again. "Your chart says that you can jerk it for 45 minutes without cumming now" - which was a lie - "that's a huge improvement from when you first started" "I've been focusing on getting better" - a semi lie, I'd been trying but was nowhere near that successful. "Before I let you go out with Victoria, I need to know. I can't let you embarrass me - or yourself for that matter." "Know? Know what?" "How long you can last." "You do know - look at the chart, 45 minutes" "No, I need to see it for myself" "Are you saying that you want me to jerk off for you?" "Yes, it's for your own good. Even if you can wank it for 45 minutes - and we'll see about that - you've never seen a naked woman before, never touched a girl, never shown anyone your dick before. All of your training is going to go out the window if you're all nervous. Pull it out for me, show me what you can do with a woman in the room." "Melissa, I'm not going to do this." I was trying hard to cover up the fact that her frank talk was giving me an erection. "If you're not going to do this, you're not going out with Victoria. It's as simple as that Grey. Don't think I can't call the whole thing off." I knew that she could. "We're going on a first date Melissa, we're not going to have sex." "Yeah, but with everything that I've taught you this one date will lead to two, then three. It will happen faster than you think. I'm not going to let this get off the ground unless I'm sure that you won't make a fool of me by cumming in your pants as soon as she touches you." I stood there confused, trying to think my way out of the situation. "I can see your boner through your pants. I know that you want to jerk, just do it. Do it if you want to go on that date with Victoria. I'm going to count to 10. When I get to 10 I'm either going to see you with your dick in your hand, or I'm calling Victoria and telling her the date is off. 1...2...3...4..." And in that moment, I made a decision that changed things forever for me. I quickly undid my pants, pulled them down and slid my hand into my boxer-shorts. I grabbed my cock and started stroking. "Underwear too, I want to see it all." I was ...