The continuation of John's introduction to cuckoldry and sissifiction.

Comments always welcome!

The Weekend

John got to work as soon as the couple left the kitchen. There wouldn't be all that much to do. The left overs would be put in the fridge and, after a good rinsing, the dishes would be cleaned by the disn washer., Besides wiping down the counter and table, and sweeping and mopping the floor, there was nothing else to do.

With the christmas bells jingling happily with his every move, John got to work. The dildo in his ass was vibrating just wnough to keep him hard, but not enough to allow him relief. Considering he'd already shot his load once, John thought it odd he would think about doing it again. But, there had been a lot of things odd about the evening, and John was sure there would be more to come.

The thinkless tasks John had to do in the kitchen gave him time to consider everything that had occurred so far. He was totally surprised by his reactions to it all. Having a dildo shoved up your ass wasn't exactly something he had fantasized about. But, he had to admit it felt a lot better than he would ever have imagined. John noticed the pressure he had felt on his balls, as they worked their way inside, had gone. He supposed they had found a 'hapy place,' and had quit burrowing into his body.

He couldn't believe how Dianne and Bill seemed to get on the same page almost immediately. If he didn't know better, he'd swear they'd talked about the night beforehand. But, neither had shown any indication they had contact in the past, so he was sure it was just his imigination. Maybe their thought processes just clicked - kindred souls, so to speak.

And, his reactions to everything. John just couldn't believe he'd fallen into the submissive sissy role so quickly. Wearing Dianne's old, tight short set with little argument, letting her put the vibrating dildo up his sissy pussy - thinking like a true sissy ther, he thought - waiting on her and the man that, for all John knew, was fucking his beautiful wife at this very moment. Was he turly a submissive, a sissy? Or had he simply got caught up in the moment. Play acting? John didn't know yet, but was sure there would be more challenges to test just what his thought process was.

Having finished cleaning the kitchen John gave it a final look over, just to make sure he'd not missed something. Satisfied with his work, he made his way to the living room. He was surprised to discover the living room empty. There was a small tube and a note on one of the end tables by the sofa. Picking up the tube John realized it was one of Dianne's tubes of lipstick. He read the note:

Sissy-Boy,

That name sounds so appropriate, doesn't it?

Your bells were distracting us, so we decided to move to the bedroom.

I'm sure you noticed the lipstick. Put it on your lips liberally. You've watched me enough times, so a sissy like you should know how to apply it with no errors. Make sure your lips are well outlined and covered, but don't have any 'overflow,' lipstick on the skin around your lips. And yes, you may go to the common bathroom to put it on.

After you've got the lipstick on properly, get another bottle of wine and two fresh glasses. Join us in the bedroom. There's no need to knock as I'm sure we'll hear the bells as you get near the bedroom.

Your Mistress,
Dianne

Yes, John had watched Dianne put on lipstick before. But, he'd never watched her with the thought he might be putting it on his own lips. So, he had little idea of just how to put it on without getting it all over his lower face. Still, he had to try. The first two attempts were total disasters. He had to use soap and a wash cloth to get it all off. That bothered him. John was sure he'd be punished for getting lipstick on one of Dianne's wash cloths. To make it worse, he didn't know if he should tell her when he got to the bedroom, or wait for her to discover it on her own.

"Honesty's the best policy," John said quietly to himself. He'd volunteer the information as soon as he could.

Finally happy with the lipstick, John went to the kitchen and got the wine and glasses she'd requested. As he made his way to the bedroom he realized he had no idea how high the heels he was wearing were. They seemed enormously high to him, but he simply wasn't used to judging those sort of things. He wondered if Dianne would tell him, if he asked.

John slowly opened the bedroom door. Dianne and Bill were on the bed, under the covers. Dianne was nude, at least on the top. Her C-cup breasts proudly exposed. The tit closest to Bill was damp. From Bill sucking and nibbling it, John supposed. Dianne's right arm was under the covers. John didn't want to think of what it might be doing.

Bill was nude at least on the top as well. His obviously tight upper body was totally visible. Even his tuned abs were visible. John felt a small stab of jealousy towards Bill. John's body would never look so manly. But, a sissy-boy wasn't supposed to have that sort of body. Bill's left arm was under the covers as well.

The faces of both were redish. They'd obviously been into some heave petting before John came in.

"Finally made it, I see," Dianne commented. "Put the wine and glasses on the end table next to Bill. We'll serve ourselves."

"Yes Mistress," John replied in his most feminine voice. John was proud he hadn't forgotten to use a female voice.

Smiling, Dianne continued, "Come over to my side of the bed, close to me so I can see you more closely."

John complied, moving his ass to make sure the bells jingled loudly.

"I see you have the lipstick on. Not a bad job for your first time. If it IS your first time, that is."

"I've never put on lipstick before, Mistress," John replied. "I'm afraid it actually took me three times to get it on even this good. And, I'm terribly sorry to have to tell you there's lipstick stains on one of your wash cloths." John lowered his eyes as he told Dianne about the wash cloth.

As John finished his admission of guilt, Dianne reached up and turned off the vibrating dildo in his ass. John's ass felt almost empty without the continual vibrations.

"I commend you on telling me about the wash cloth," Dianne said with a hint of anger in her voice. "But, there's a number of things wrong with your reply. First, did it sound like I asked you a question?"

"Well, no Mistress. Now that I think about it, it didn't." John was really nervous now.

"That's right. It was an observation, NOT a question. You'll NEVER talk to either of us - short of a 'Yes Mistress,' or 'Yes Master' - unless we directly ask you a question. Is that clear?"

"Yes Mistress," John said meekly. 'Yes Master?' Now Bill was his master?

"And, you broke eye contact! You will NEVER break eye contact first." Dianne took a breath. "The eyes are the gateway to the soul. I want to make sure all I see in your soul is adoration, servitude, and maybe a little bit of fear."

"Yes Mistress."

Dianne once again reached for the dildo controller. She returned it to the low vibrations he'd become used to. John let out a satisfied sigh as the familiar movement returned. The bells sounded out a small tingle as he inadvertantly wiggled his ass. John blushed. Dianne just smiled.

"Very good," Dianne continued in a more pleasant voice. "Tomorrow we're going to get you a nice note pad - pink would be a nice color - to note your infactions. For now, I'll keep track of them mentally - lipstick on a washcloth, answering without being asked anything, and breaking eye contact first. I'm sure Bill and I can come up with some appropriate pentalties for those errors.

"Changing subjects. Can you tell me why we're all here in the bedroom, Sissy-Boy?"

"Er, well, so you and Bill can have sex." John didn't know why Dianne was asking the obvious.

"Well, that's basically correct," Dianne replied. "But, just why are we having sex?"

"So I have a better chance of keeping my job," John answered.

"Yes, and just who suggested this to me?"

Now John understood. Dianne wanted to make sure he remembered he was the one that brought this idea up to her. It didn't seem to matter to her that Bill had impied it first - it never had.

"I did, Mistress," John replied meekly.

"Very good, Sissy-Boy. You're getting pretty good at this! Now, follow my logic. I don't expect your feeble mind to totall grasp it, but at least try.

"You suggested I get fucked by your boss to, supposedly, keep your job. I would surmise that you actually always wanted me to get fucked by him, or you'd have never thought about telling me about it. It may have been subconscious, but you always wanted me to get fucked by him, or some other REAL man.

"Now, that said, it also follows that you do not consider yourself a real man. I mean, why would a real man suggest his wife get fucked by someone else? Plus, no real man would let his wife dress him in her tight short set. And, he especially wouldn't let her put a cock shaped dildo up his ass. Only a sissy would let his wife do all that. And, especially get hard when she does. So, that means you're a sissy! Do you follow so far, Sissy-Boy?"

"Yes Mistess." John couldn't think of any thing else to say. Plus, she didn't ask for his opinion.

"OK. To continue. Since we've established that you're a sissy and you really want me to get soundly fucked by a real man, I personally think you should watch. Not only should you watch, you should participate!

"Not in the classical sense - no fucking for you. You should ask this man who's fingers are, even now, going deeper than your scrawny dick, to fuck me like I deserve to be fucked. Not just ask, but beg him to fuck me like you can't."

Dianne seemed to be on a roll. And, even though it was one of the hardest things he'd ever done, John managed to maintain eye contact with her. He knew his eyes showed her he was confused, humiliated, and, unfortunately for him, excited.

"You will follow my instructions with absolutely NO hesitation, is that clear?"

"Yes Mistress."

"Very good. Now get over to Bill's side of the bed." Without question John did as he was told.

"Now beg him to fuck me!" Dianne almost yelled the command. Not so much because she was pissed, but more because she was more than ready to have that big cock she'd been playing with in her cunt. Well, as soon as some things she and Bill had agreed to happened, that is.

"Please, please Bill, Sir. I beg you to fuck my darling wife with that enormous cock of yours. My little dickette isn't big enough to give her any satisfaction. I implore you to give her the fucking she so much deserves."

"Now, how can you say he has an enormous cock when you're not looking at it, Sissy-Boy?" Dianne asked. "Pull the covers back and look at what will be inside me shortly."

John was terrified. He'd never seen another man's penis hard, and wasn't sure how he would react. But, as instructed, he pulled the bed covers back to bring Bill's cock into view.

It was enormous! At least to John it was. Easily 8 inches long and bigger around than he could ever have imagined. As he stared at the first hard cock he'd seen besides his own, his little thing jumped. He was totally embarrassed that his body responded so positively to seeing another man's cock! No matter what his brain said, it was obvious to everyone he was excited.

"You've asked Bill, now beg his fuck stick to do it's job!"

"Please give my dear wife the satisfaction she so justly deserves," John said. "She's put up with my little thingy for so many years, she is entitled to have a real fuck. One I know you can give her. Please ravage my princess' cunt as I know you can."

"Not bad," Bill finally commented. "But, first of all, you haven't showed the proper respect for a real man's dick. A sissy like you shouldn't just stare at it. No! You should respect and honor it. You should fondle and kiss this tool - prove that you truly are in awe of it."

"May I, Sir?" John was totally shocked that comment actually came out of his mouth. He'd said it before thinking. He honestly couldn't believe he'd just asked for permission to fondle another man's cock!

Both Dianne and Bill chuckled at John's honest comment.

"I tell you what," Bill said. "Your exceptional wife here has got me so excited, I'm afraid I'll cum just putting my cock in her pussy. I'd really hate making that sort of mess. Plus, it shows a lack of discipline I'd rather not have her see."

John was trying to figure out just where Bill was going with this. Of course, he knew he'd find out shortly, and that he'd probably not like it.

"Now, I can fuck for hours," Bill bragged. "Cumming 2, 3, even 4 times without going soft. But, starting a fuck session by cumming on the woman's cunt just isn't my style.

"In the past when I've had this problem I've solved it by beating off. But, with a Sissy-Boy standing just a few inches from me, I think there's a much better solution.

"Not only do I want you to fondle and kiss my cock, I want you to suck it off! Give me a good blow job! Show me and my tool just how much you adore a REAL cock!"

John stood there totally shocked! The very first real man's hard ock he's ever seen and he's also expected to give it his first ever blow job? He's NOT gay! But, his body once again gave his true feelings away. His little dickette almost shot a load!

"Here's the rules, Sissy-Boy," Diane said. "Since Bill's so excited, it shouldn't take long for you to get him to cum. I'll give you 2 ½ minutes. And, when he cums I don't want a mess. So, you'd best take it all in your mouth - and swallow!

"I want to see all sorts of lipstick rings on Bill's cock when you're done!"

Now the lipstick made sense to John. They'd planned for him to give Bill a blow job all along. They'd planned on totally humiliating him.

"Oh, and put that dildo in you ass on high vibrate," Dianne added.

With his body saying he wanted this, but his mind saying otherwise, John simply didn't see any solution short of doing as he'd been told. He cranked the vibrator up to max - a shiver flowed through his body, causing the bells to ring once more. Then John rubbed his hands together to warm them. He had no idea why the thought of touching Bills rod with cold hands seemed wrong, but somehow it did.

Satisfied his hands were warm enough John put one hand on Bill's hard cock, the other cupped his balls. John leaned over and placed a kiss on the head of Bill's member, leaving a bright red lip print. As he slowly stroked the rod and gently massaged the balls, John opened his mouth and took Bill's enormous head into his mouth. He ran his tongue all around the head, And, when he reched the underside of the head, he was rewarded with a jump from the solid stud.

John slowly removed the head from his mouth and began kissing the hard rod on the back side moving slowly towards Bill's ball sacks. John gently took first one then the other into his mouth, massaging each with his talented tongue. As John spat each out, he noticed they too had lipstick rings on them.

Again John kissed the hard member, this time up towards the head. Again he took the head into his mouth. This time pushing his head further down, taking more of Bill's cock into his mouth. John's lips were stretched more than they'd ever been stretched, but he persisted in getting more of the man's cock into his mouth.