Wife's Cuck Boyfriend

Not sure how to start this or even how to tell this story. I’m a 39m that has been married to a 36f for 12 years. She is the love of my life and I’d do just about anything to make her happy. Last year she had a few drinks one evening and confessed to me that she had been reading cuckold stories for some time and they had made her so horny. She had been fantasying about having a cuck to turn into a sissy but also knew that I wasn’t going to be into that as I was a true alpha male. This is true as I am an alpha through and through. She then admitted that she had been seeing this small weak beta from work and had been dominating and preparing him to be her cuck. I wasn’t sure where she was heading with this but sat there and listened to her none the less. To make a long story short she wanted me to be the so called Bull to cuck this boyfriend of her’s.

I couldn’t believe my ears, but like I said she was the love of my life and I wanted to make her happy. I have to give her credit she had put a lot of thought into this plan and I was going to help her out or I at least wanted to try. It started out pretty mild as she brought this small framed guy home one Friday evening. She made him get naked and I almost laughed at the sight of him. He was about half my size all except his little dick that might have been better described as a big clit. As I said it was kind of mild as she had him sit on the floor and watch as we had sex. Not sure if it was because we were being watched or what but the sex was really good and I ended up pumping a huge load in her pussy. This is when it got a little weird for me, she had him crawl over and start cleaning her pussy with his mouth. He was eating our combined juices and pulling on his little dick. You could easily see that he was loving every minute of this. My wife came twice as he cleaned her and once he was finished there wasn’t a trace of my cum anywhere.

This all progressed over the course of a few months. She really started to turn this little guy into a full blown sissy. It started with a cock cage that she locked in place on him and kept the key. Then she started to make him wear panties for our meetings. Then one evening when I got home I thought she had invited one of her friends over as there as this pretty good looking woman sitting at the bar chatting with her. It actually took me a few minutes to realize that it wasn’t a woman but her beta boyfriend all dressed up. Well that was an evening I’ll never forget as long as I live. My wife first fixed me a drink then had me move over to the couch to relax. She then went over to the sissy and whispered something to him/her/it and I watches as she got down and started to crawl in my direction. Once kneeling in front of me she released my cock from my pants and stated to suck me off. I looked at my wife who I could tell was really worked up. She had this sexy/horny look on her face one had was holding up her skirt as the other was inside her panties and working on her pussy.

I will say that this sissy knew how to use his mouth as this was maybe the best blowjob I’ve ever received. He had brought me to the edge of cumming 3 times and somehow backed off before I could cum. At some point my wifes said “assume the position sissy” and he quickly set my cock free and moved to the middle of the floor on all fours. My wife pulled up his short skirt pulled down his panties just below his ass cheeks so his caged cock didn’t show and started to lube up his ass. She then motioned me over applied some lube to my cock and said “fuck her”. I did as told positioning myself behind her and slipped my cock into a very tight warm hole. Took a little work to get balls deep but I did as the sissy would make all kind of yelping and moaning sounds. My wife had removed her panties hiked up her skirt and positions herself in front of the sissy. She took a hand full of hair and pulled the sissy’s mouth down to her pussy. At this point I was full on fucking this sissy’s ass and loving every minute of her tight hole. This went on for about 5 minutes when my wife started to shake and hump the sissy’s face before howling she was cumming. The sight of this set me off and I started to dump a huge load deep in the sissy’s ass. I collapsed and laid on the floor next to the sissy and saw there was a big wet spot forming in her panties. I could only assume that she had cum as well from getting her ass fucked.

Today we are still actively playing with the sissy. We don’t have kids so the sissy has moved in with us and has taken the spare room. She is almost always dressed as a woman with the exception of when she goes to work. I’m still not sure exactly how I feel about all of this. I have gained an extra couple holes to fuck and even if my wife isn’t in the mood the sissy is always more than happy to give me a stress relief. I still consider myself a true alpha male, but now there as some doubt because I really do enjoy using that sissy’s mouth and ass.

By Buttboy

Strange CONFESSION

Report