I took your website's advice and bought some nice panties for James to wear. I got some full nylon briefs so he would have room to expand as it were. To cut a long story short, I managed to get him into a pair last night and proceeded to massage and pleasure him through the silky nylon. I told him that I found it really sexy to see him in them and complimented him on his erection in response to my touch.
He certainly enjoyed the experience and lay there moaning with pleasure as I teased and rubbed his penis to completion inside the panties. I kissed him tenderly and told him that I had always wanted to do that and that wearing them for me didn't mean he was gay or anything. He said that he enjoyed it too so I took the opportunity to remove his soiled panties and give him the clean pair to put on as I wanted him to sleep in them. He told me not to be silly but I faked annoyance and he relented, putting them on for me after a few minutes. I held his penis as we settled down to sleep and felt it erect in my hand once more. I told him it felt lovely through the nylon and he gave what I thought was a nervous laugh.
I think he enjoyed it but didn't want to admit it! When we woke, I pleasured him again in his panties before he got up and showered for work. I've washed both pairs now and am going to leave them in his underwear drawer ready for the next step. I'm going to try and do what was suggested and insist in some way that if he wants sex, he has to be pantied. I haven't decided exactly how to best achieve this but am sure I will think of something.
Thanks again for your help, it does seem to be going well so far.
Thank you for your letter Jennifer. Well, what wonderful news, off to a great start, take your time, enjoy the journey. If you continue to tease him with the panties, make them your focus for the time being, get him addicted to them and of course, no sex without him wearing them as your goal. You can use your own panties as well to tease him, maybe you should get some full nylon briefs yourself to replenish the stock.
Sitting on his face wearing a pair while using another to masturbate him could be fun. You'll figure something out but in the meantime before giving him the ultimatum tease and play, make it fun for you both, the best sex ever, oral sex through the panties could be good for him, make them an important aspect, then spring the trap.