Jill Steps Out; A Cuck is Conceived - Part 4 - Sex Stories

Jill Steps Out; A Cuck is Conceived - Part 4

... they?” “Yes Dear, I think this suits you perfectly. I love the way your cock is just barely hidden. Colby is also going to love the new you. Come here and give me a big kiss!” During the next week she prepared him for his next step, anal sex. She explained how wonderful it was, after all he had seen her take a cock in her ass many times and have numerous orgasms from it. He was a bit reluctant at first but again he knew it was the role he had willingly chosen. After he accepted the idea, she had him get on his hands and knees on the bed and, after lifting his skirt and pulling down his panties, gently inserted an anal plug. She explained they would start with a short time and then extend it until he was fully used to it before she would actually use the strap-on silicone cock she had purchased to fuck him. Greg readily took to his new situation. He loved the soft colored panties and camis. Wearing the skirt and blouse at home also pleased him. He was surprised at how quickly he was becoming accustomed to the clothes and anal plug. He began to look forward to his first fucking by Jill. While all this was evolving, Jill spent time having sex at Colby’s house, not yet wanting to bring him to the house until she was sure of Greg’s acceptance and complete transformation. She reveled in Colby’s attention to her; the countless screaming orgasms he gave her and the cum with which he filled her. Life was good. He had immediately noticed the new anklet she was wearing when she ...

... arrived on Monday night and recognized its significance. He told her it looked really good on her and that it was a good way to subtly show people, who recognized it’s meaning, what her status was; it could result in more fun for both of them. Greg had also noticed it but was clueless about its meaning. He did tell her he thought it complemented her beautiful legs very well. She did tell Colby everything that was going on between her and Greg so that he would understand the new situation when she invited him back to the house. She also asked him to consider letting Greg have some sexual contact with him. He told her that he was reluctant about that but he would consider it. They had discussed her goals with Greg so he understood it was not a gay thing but that it would be a recognition and affirmation by Greg of his new role. On a Thursday night, which would have been the sixth night of having the anal plug, Greg told Jill that he was ready for her to fuck him. He had shaved everything he was supposed to and really needed sexual release. He had not had any climax in over two weeks. Meanwhile he had been licking Jill clean almost every night after she arrived home from Colby’s. Jill was happy he had asked for it. It meant he was almost fully adapted. It would be almost complete after tonight. They had talked about how it would work and Greg had read about male sexual response from anal fucking. He fully expected to have an orgasm and ejaculate a large load which he would catch in a ...