Her Sissy Again 03

Clyde is a successful construction project manager with a house about 40 minutes from ours. He was married once, briefly, but has stated that he has zero interest in ever doing that again. He isn't all that different from me, just in better shape. His cock is only slighter bigger than mine. But unlike me, he doesn't have a submissive part about him. He has had no issue stepping into his role over the last 3 months, taking care of my wife, helping set rules and boundaries for me, with much encouragement from my wife. He has told me that dominating a male has never interested him, but he views me as more of a girl anyway, and when the prize is unlimited free access to my wife, hell gladly step in where she asks.

The first time I met him was a few weeks after the night my wife started this journey again. I was to be dressed in a very feminine, pink dress, with ruffled sleeves. White stockings with pink mary janes. I was tied to a chair in the center of the living room, complete with a blindfold and gag, and a plug in my ass which my wife almost always requires when I am home now. She left me home like this while she went to dinner with Clyde. This was a scenario I had always begged for in the past. Now it was finally happening.

They had entered the house calmly, quietly that night. She had told him to take a seat while she changed. When she returned, she simply stated, "Well this is my little sissy husband."

After a few minutes of back and forth banter, he asked to have the blindfold and gag removed so the three of us could speak for a bit. For the next hour, introductions and small talk occurred. Then he told me that my wife has told him everything there is to know about our kinky sex life, and all the depraved things I've asked for in the past, or have done in the past. And he let me know that she has asked him to assist in making sure that I remain obedient and not interrupt or disturb them while they enjoy each others company. She had given him my keys at dinner as he had asked for him exclusively to have access to her sexually, which he said he had no intention of needing to use.

So now he was in control of my chastity, and, at my wifes request, only he could grant me permission to see, touch or taste her pussy. My wife chimed in that I was expected to be in sissy attire anytime I am home from now, and especially feminine whenever Clyde is around, with him nodding to affirm. He told me that he should be the only man in the house when he's around so there's no confusion. He then told me that my wife mentioned that getting to watch her get fucked wasn't something I routinely got to experience in the past, and he thinks it only fair that I get to witness them together that night.

With that, my wife rose from his side and reapplied my gag, while whispering "So you can't complain or beg while you watch".

She dropped to her knees in front of him and started kissing and licking his hard cock. She sucked on his dick for a few minutes before sitting on his lap so she was facing me. She didnt break eye contact with me as she took his whole 8" cock into her pussy. As she slowly started riding him, I could tell that her focus on me was slipping away. He was playing with her gorgeous tits, and kissing her neck. Then, like a predator in the wild, he lifted her up and dropped her on her back, with her legs on his shoulders and started fucking her. With every long, deep stroke, he methodically brought her closer and closer to her first orgasm. She didn't even know I existed by now.

My mind was very conflicted. with the way our lives had gone the last year, I never thought I would be in this position again. The last time I was her cuckold, we were headed to divorce. Were we again, I wondered. But at the same time, this was a situation I have always wanted to be in, a way of life I used to beg to be our normal all the time. And I was very horny in that moment.

My thoughts were interrupted by the sounds of her first orgasm, and it sounded like a good one. He remained still inside her, giving her a minute to recover, before starting on her again. He sounded as if he was starting to build close to his orgasm, and he started to slow his pace down a bit. "Don't you think it would be nice to give your sissy a close up?" All she could do was moan.

He led her over to me and told her to put her hands on my knees and look her pathetic sissy in the eyes next time she orgasms. With her now bent over right in front of me, feeling her breath on my face, he entered her from behind. He fucked her slowly in this position for a few minutes while i was in awe of what was happening. My sexy wife, bent over in front of me, panting, sweating, moaning, while another mans dick slid in and out of her pussy was a sight to see. I could tell they were both getting close from their rhythm and their sounds. Clyde grabbed my wifes hair and held her head so she was looking at me. A sudden smirk came across her face and she moaned out, "I'm going to make sure you never get to do this to me again!" At that moment, he started grunting as his orgasm released, filling her pussy with his load of cum. She begged him to fill her up. The whole moment pushed her to another orgasm herself, and she finished, moaning in a high pitched screech, staring me down the entire time.

I've been allowed to watch one other time in the last three months, with much less inclusion of me. I was just a forgotten about cuckold in the corner while they enjoyed each others bodies. After they were finished, she called out to me from the bed. "Hey sissy, I hope you enjoyed that. I told Clyde tonight that while I am glad he doesn't mind including you, I prefer to have privacy with him. Of course he told me if I prefer that, then that's how it will be. So you won't be getting another show like that again. When we remove the gag, make you sure thank us for allowing you to see what we did."

They stayed cuddled up and talked for a few minutes before he came over and released me. I thanked them as instructed. She then told me to get ready for bed in the spare bedroom as they had no use for me the rest of the night.

I resigned myself to the spare bedroom. Changed into a pair of silky pajamas that were left on the pillow for me. They were purple with ruffled edges, and said Daddy's girl across the chest. I laid on the bed and locked my ankles into the straps at the foot of the bed. and then cuffed my one hand into place at one corner of the bed and awaited her to come in and finish securing me for the night.

Much to my surprise, Clyde entered the room. "Your wife asked me to come in and tuck you in. And from the look of your pajamas, I see why. Except I'm not your daddy you silly sissy. But we can find you one if that's what you want."

Before I could say anything, my gag was strapped tight onto my face, then my blindfold. And my other hand cuffed into place. While he got me set up for my night, he told me that we needed to have a one on one conversation soon and he'd let me know when that will be. Earbuds were put in my ears next, and I was told my wife made it clear she doesn't like me listening without permission so these were necessary. He told me that getting to listen to them have sex would be a reward for good behavior going forward. He said she had something queued up on my phone for the night, and just then the noise started in my ears.

Sissy Hypno? I had mentioned this only once to her before and she seemed to not have the slightest interest in doing that. But here I am tied down for sleep with hypno playing in my ears, drowning out the worked around me.

Ouch!!! Nipple clamps were applied. Something I've always loved in theory. But after a while, they just plain hurt. And with my nipples being so sensitive, I didnt really want them in pain. I think I groaned through my gag to object, but if any noise came out, it didnt make a difference.

A rough night of sleep ahead was in store that for me. It wouldn't be the last...