I have always had bisexual fantasies, 50 year old male. My wife knows of this and knows I’ve sucked a few c****. She has never judged me but also expressed zero interest in seeing it.
Last year in September she started talking about our annual Halloween party at her best friends house. She said she Wanted to Step up our game in the costume department. When asked what she had in mind, she said she was thinking of gender reversal. Now she has no idea of my desire to dress as a girl for fun. So I reluctantly agreed , then the packages started showing up at the door. She wouldn’t let me see anything and was going crazy with curiosity. While giving me oral one night she started playing with my back door which really surprised me and made me explode instantly, then she gave me a c** filled kiss which she has never done. And then will h a wicked grin she told me how much it turned her on. Over the next several weeks this was repeated eventually moving to a small d**** in my ass. I was loving every second of this. I spent two weeks walking around the house in giant high heels for practice. Then came the morning of the party. She made me shave my beard and mustache, then I got in the shower and a cream that made my skin burn a bit and then I watched all my body hair rinse off my body, I looked ridiculous but felt incredible. After rubbing some pretty smelling lotion all over my body I was getting dizzy with excitement.
I was then given the cutest little panties to put on and relax. After some time she came out and looked unbelievably masculine with facial hair, boots, etc. she saw that I was very hard and sticking out the top of my panties. She said that will not do and grabbed my hand and led me to the bathroom and handed me two enemas and told me to throughly clean my self so I don’t have to use the bathroom and get my panties dirty. I agreed and proceeded to use both enemas. I loved it and was leaking from my member. She had me lay on the bed and was putting what seemed like way too much lotion on my butt. Then she kneels between my legs and without losing eye contact she lowers her zipper and whips out the most perfect c*** I have ever seen. I was speechless and then she grabbed my d*** like a handle and slowly penetrated me. It hurt a little but she was so loving that she was soon driving that strap on in me like a pro. I had lost quite a bit of firmness in my c*** but she used more lube and was stroking me as she f***** me hard it took no time and I was shooting all up my chest. She surprised me yet again and started slurping up my mess then, with her c*** still in my ass, she leaned forward and and fed it to me it was gross and incredible. After I was cleaned up she got me dressed in a little girl style poofy pink dress with a pink bra with almost no cups thigh high white stockings an a different pair of pink ruffled panties. A wig with piggy tails and bows and pink lipstick and a little bit of makeup. Then came the next surprise was what looked like little girl flat shoes ( maryjanes maybe?). I saw myself in the mirror and started belly laughing, I looked utterly silly. But it was all for fun, right?
We drove to the party and after idle chit chat and good natured ribbing we were well on our way to a great drunk. My wife’s BFFs hubby grabbed me and started dancing with me. I thought I would discourage any groping by doing it first, bad idea he was rubbing what felt like a huge hard d*** against my ass, as I realized I was getting hard I saw my wife doing the same thing with her BFF. Other people were cheering us on. Thank god the song ended and we all laughed and enjoyed many more drinks. The party was winding down and suggested we leave but there was no way we could drive and decided to stay the night. A few more drinks and very horney my wife said she wanted to watch me face with the husband again so I replied I want to watch you dance with her again. Immediately they were dirty dancing and I felt him behind me as I leaned against the bar and his hard d*** was once again rubbing up on me. I couldn’t take it any more and stared pushing back on him, he grabbed me and started grinding hard against my ass which felt amazing. Then I noticed my wife had her hand under her bffs skirt. And I almost came right there so I decided f*** it let’s see where this goes and reached behind me and started rubbing him through his pants, it was HUGE!! Then his wife dropped to her knees and unzipped my wife’s pants and fished her perfect c*** out and started sucking. My wife looked at me and looked down at my hand on his d*** and looked at what her friend was doing and nodded her head as if to say do it baby. So I turned around and pulled his pants and underwear if in one motion. I saw his d*** and completely forgot I was a straight married man and sucked that monster for all I was worth. Then my wife told him to bend me over the couch at the same time she was bending her over. He helped me to my feet, bent me over and I watched as my wife started f****** her pretty friend and hand him a small bottle of lube. After lubing is both up he gently eased his c*** in my now practiced hole. It was amazing I came well before he did. His with came together with my wife and they watched and were telling me how hot it was watching me dressed as a little girl getting f***** hard by that beautiful c***. He finally came deep inside me, it felt unbelievable. We all climbed into their bed my wife asked if I minded if she tried his c*** out. So I got up, c** dripping down my legs and got a washcloth and cleans him up and then started sucking him hard. Then I guided him inside my wife. It wasn’t until then I realized she didn’t have her girl d*** on and at that exact moment I felt the head of a d**** going in my ass. The BFF was f****** me. This lasted for 15 minutes or so until he came in my wife at the same time the woman behind me was spasming which caused my d*** to just start flowing c** out with no o*****. Still was fantastic. When he pulled out of my wife he turned and put his c*** in my mouth to clean then I could not get to her sloppy p**** fast enough. I ate her to another o*****. The next thing I remember was waking up with his d*** in my ass again f****** me slow a long, it was heaven. I the got to f*** the friend with c** squishing around in my butt and me wife got another cream pie and I gladly ate it. I wanted to take a shower and clean up but wife was having none of that. She said we are going home just like you are, the walk off shame. We spent the rest of the weekend in role reversal. Now he f**** me whenever we are together with our wives watching.