I had been having sex with Samantha a woman who worked with me as a cleaning lady for a couple of years now, this as encouraged by her older cuckold husband Pete. He was 20 years her senior and couldn’t keep up with her, she was a sexy mynx and always wore sexy underwear and stockings for our sex sessions. I had fucked Sam in front of her hubby Pete, and he did cleanup on both of us, him cleaning her pussy and sucking me off after I had fucked his wife whether I fucked her in her pushy or ass. Things were good between us my wife left me and I just continued a relationship with Sam, everyone knew we were fucking we didn’t care and Pete loved it. I am their bull. The more and more we had sex though, the more and more he was becoming a sissy boy. We got to the stage now where he wore makeup while we fucked and sometimes used a butt plug in his arse while I did the same to his wife only with my cock. I had been given a few blow jobs by Pete either to get me hard for his wife Sam or after we had sex to clean my cock. I hadn’t cum in his mouth I kept my cum for all of his spouses holes, I had often thought about giving him my seed. I had also thought as their bull of one day taking his arse and fucking the shit out of him in front of Sam. One evening Sam and I were in their bed alone, Pete was at the Golf club, I mentioned to Sam what she thought of his mannerisms when we are having sex. She confirmed to me and also said he wanted to be a sissy boy. “Does he now, we’ll have to to something about that”. Sam and I devised a plan to sissify her cuckold husband. I asked her if she had heard of pegging? “No” she said. I then showed her some pegging videos where the wife wears a strapon and fucks her cuckold husband. She said it was kinky and would be right up Pete’s street or ass. I also told Sam we would get him in stockings and lingerie we both laughed, then ordered on love honey the strapon. We told Pete that we were going to have a cuckold sexing tonight and to dress in the underwear and stockings, Sam said he was nervous and excited at the same time. I arrived at their house from work and had a stressful day and could do with taking it out on my couple sexually to relieve the stress. Tonight I wouldn’t have cared who’s ass I would fuck as I’d had a shitty day. We drank some wine and fair play for Sam she did a good job helping her hubby dress as a sissy even painted his toenails bright pink I could see them through the stockings he was wearing. Sam was wearing stockings as usual and looked her sexy self, just then she brought out the strapon with the belt, Pete looked shocked, “What’s happening?” He said. “I think you know Pete” I said. “Bend over, Sam lube his ass, Pete Sam and I will flip a coin the winner gets to fuck you in the ass” I said. As he was bent over his greasy ass hole on show, I had the coin in my hand, “Heads or tails Sam?” I said. “Tails” She said. “Hope it’s heads” Said Pete. He was ready to be bummed by his bull, me who had been fucking his wife the last couple of years. “Dirty sissy bastard wanting my cock up your ass” I said. I flipped the coin.......... “Tails it is” Said Sam. She put the black 6 inch strapon to Pete’s ass and slid it in and began to fuck his ass. He whimpered and moaned she was hurting him but after a couple of minutes his pain subsided and he moaned with pleasure. Sam ass looked sexy as she pegged her husband her ass going back an forth, I fancied some ass too so I lubed my cock and shoved it into Sam’s asshole, it didn’t hurt her, she was used to my cock. As she pegged him she did give him a reach around and wanked his cock, it didn’t take long and he came all over her hand. A minute later I came in his wife’s ass. Then Pete did a clean up on my cock and Sam’s ass.