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Once inside the apartment, he immediately took me into his bedroom and asked me if I ever jerked off before. I told him I did not even know what he was talking about so he said he would show me. He dropped his pants and out popped his huge boner. He had a big cock to begin with and compared to mine he was HUGE. He started jerking it and within 5 or so minutes he came inside some tissues on a desk as I watched. That was so cool to me and I was so grateful that he showed me what masturbation was all about. Can't say that it made me horny that first time but I will never forget it. We did the same thing maybe a dozen more times that year except he eventually got me to participate. He had me touch his cock at one session, than the next time he had me stroke him. I really enjoyed all of it and the excitement of doing something "i*****l or nasty" was a rush. Eventually, he asked me if I would jerk off with him. I said I would try and lowered my pants. I was not getting hard playing with it. If you can go 10 minutes without cumming, I'll have sex with you as many times as you want this weekend. But if I get you to cum in under 10 minutes, you won't be getting laid at all, and you have to do whatever I say until Sunday night. Do you accept my challenge, sissy boy?" I plead for us to just have normal sex instead. She shook her head with an amused grin. She asked me if I'd rather just stay locked up all weekend instead. I shook my head in despair. "Good" she purred.She slid my panties down my hips slowly. Not all the way, just far enough to access the chastity device. The produced the little key from inside her bra and carefully opened the little padlock. My dick was straining against the hard plastic already. I was electrified. She unsheathed my tortured little penis, and it instantly sprang to life like some inflatable toy. She found this delightful and giggled at how desperate I was. Keeping in line with the rules of her game, She pulled out her phone and set a timer for.
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