It should be the one he slightly fears.Over time the big one will become the medium one. This is especially true, if you train his ass with butt plugs... You can humiliate and tease him by talking about how he will soon be able to take much larger strap-ons with no trouble in the near future. The regular and consistent physical training will prepare his fuckhole for your use.But it's more than just getting used to things physically. In many ways, the mental and psychological changes in him are. "After this the conversation turned to more normal matters and Isa informed us that since we were going to be on our own over Christmas day, she and Joe had booked us in for Christmas dinner at a lovely little restaurant not far from their office. She said that we would be there for one pm. and should take the opportunity to dress smartly but not too formally. She also suggested that we might want to contact some of our friends and see if they wanted to join us between Christmas and New. What would he do next, she contemplated. Sherry meanwhile was getting increasingly aroused and wiggling her butt in between spanks. Harvey caressed her butt and stroked her pussy between her legs and said, ‘Sherry you can’t come tonight unless I give you permission. If you do, then your punishment period will be doubled.’ Sherry winced at the prospect but decided to defy Harvey and asked innocently, ‘And what if I don’t mind that?’ The room laughed at her audacity and poor Harvey managed to. I was still a little nervious about him taking the lead with her so I told him my preference was; massage starts with towel and panties on, once the panties were off, gentle fingers on her pussy while kissing her breasts (no kissing her mouth), then tongue her pussy until she has an orgasm, then he would strip for her. If she 's interested, he would let her touch his cock. Then if she wants intercourse from front or behind (her choice - gentle at first but then let her tell him how hard and.