Dear Mistress Dede,
I’m from the Netherlands and living in Amsterdam. I used to live in the area of Rotterdam with my ex wife, from who I’m divorcing coming January 2020. I’m 57 years (12th October 1962) old and met my ex wife 49 years ago. And although I told her that I’ve had the feeling of wanting to crossdress since I was 13y ears old and probably found out or discovered my fetish for soft fabrics like silk, satin and lace when I was 6 years old, she never really encouraged me to have it my way. She sure tried and later in life she even went with me to swinger clubs, but always told me afterwards she did it all for me but it didn’t spice her up much. Funny thing was that I let her flirt and go swing around but me myself wasn’t into flirting with other women at all. Sure I liked what my eyes saw. I love to watch women and the female look of lingerie and high heels etcetera had my attention all the time. I also saw the well endowed men with better shaped bodies and bigger cocks. Then in 2007 I was on the internet surfing around and suddenly I found a site about cuckolding. I read it and I thought ‘that’s about me, I didn’t know it had a name’ .. I new my repressed feelings about crossdressing and now I understood my behavior at these swinger clubs … I loved watching my wife (now ex-wife) having sexual activities with these alpha males. And I saw she loved it too. So after a few weeks I told my then wife about this cuckold site and my fetish with this all. To make the story a bit shorter, she didn’t get it al first but 7 years later she made me from a wannabe cuckold into a real cuckold by meeting with a guy from the internet she knew because they chatted almost 3 month without me knowing this. I knew she chatted but that was random with all kind of people. After a while they found out they both lived in the same town and wanted to get to know and see each other and they agreed to meet at a cafe in a garden center. But three days before they had planned to meet, my youngest son (I’ve three kids the oldest a female and the next two kids males. Unfortunate the second child, died after three years of cancer on the spine, this was in the year 2012 he died at age 22 years old, so sad, we were in shock and probably it is partly one off the reasons for getting to the point of better stay good friend but separate and divorce). Back to the story … my youngest son ask me to go together to the sauna for a day, a father-and-son together day. I agreed and we went to the sauna at 11:00 am in the morning and planned to get back 11:00 pm in the evening. My wife was planning to get that afternoon late to meet her girlfriend who had her birthday anyway and treat her for a diner at a nice restaurant. When I my son was a the front door to go I kissed my wife goodbye and after I left she was chatting again and while also chat to this guy she had planned to meet later that week she suggested her being home alone during the day if he would like to come over and drink a coffee ☕️ before she had to go to meet her girlfriend. This guy said okay to this proposal and around noon he stands at front door of our house. She lets him in and was nervous because he was really good looking and he right away complimented my wife about her appearance. My ex wife is a real foxy lady you must know. Still looking very youthful (10 years less than her age) and on her black high heels, in the leather pencil dress and a off-white satin blouse (I remember these details very clear because she told me the same evening all of what had happened that day, the day I was made a IRL cuckold). After one coffee this guy stands up and walks across the living room and asks my wife who automatically stands up too, if he could kiss her and in a blink of a second she thinks about the last 7 years me telling her to act accordingly to her feeling if the would come in a situation of having an affair or sexual encounter outside our marriage. She says yes to this guy and they kiss and lightning strikes them both in a good way. Minutes later they lay on the soft carpet in front off the fireplace and they make love twice in the next hour. After that they both went upstairs to the big spacious shower were they make love for the third time. After that my wife gets some wine 🍷 and they enter our bedroom and lay down on our bed and talk about what just happened. After the next hour my wife and this man do it a fourth time and about 4:00 pm he left the house and my wife gets ready to wait for her girlfriend who came around 5 pm … after telling her girlfriend, who already knew about my cuckold and crossdressing fetish (we knew about them and they about us too going to swingers clubs). Off course her girlfriend told her to tell me the same day all about this first encounter because I’d agreed to it and now would be the test to the reality if the wannabe fantasy would also stand in reality.
So when I came home and her girlfriend left we went to bed … my wife came really close to me and caresses me and started to talk with me about her day, meanwhile checking with her hand on my private parts how I was reacting. She told everything and I listened carefully … after she paused she asked me how I was doing but my always a bit tiny penis was hard and bigger than normal, so she knew my answer before I spoke a word. I only had two questions, the first was ‘did you enjoy it and was it a good feeling to do’ and the second was ‘would you like this again or was is okay for just one time’ … her answer wasn’t a big surprise … ‘Yes it was lovely, I really loved to get fucked by a hard and real big penis, sorry you were right yours is to tiny and although I love you, now I understand what I’ve mist all these years’ … on my second question she answered; ‘Yes, I would love that, are you really okay with that’
My answer was ‘then today you made me officially your cuckold and you are now my cuckoldress, the hardness of my tiny one says it all my love, please go on, I feel very happy for you and at the same time it makes me horny, I wanna get to orgasm right now. My wife gave me a blowjob I hadn’t had in years, probably more than over 15 years ago.
Afterwards we slept both very deep and I held her in my arms. Next morning we both were very happy and joyful … a new season had started. The guy and her fucked three times a week with several orgasms, mostly I wasn’t home and after two weeks she told him about my knowledge them having an affair and having sex. He first thought I would knock him down but at the lunch we had asked him to meet me in real … he saw that I was okay with them having sex together. Sometimes I stayed downstairs and prepared diner for us three or she told me he had been over to get laid by him earlier that day when I was away. The fun in the beginning was that my wife’s appetite had went up so high that we too had more often sex together often the same day she had sex already to her lover.
After a few months this guy moved to another town and their sex affair became less and less. My wife started to miss these frequent sex appointments … and after three month I suggested to make an account for my wife at a polyamory dating site and find her a new lover … she got three candidates and after meeting them all the next couple of weeks another two had responded. She would meet at a restaurant and with two she had sex afterwards. One of them two lives to far away but one suited the need and she had her second lover for another 5 month … I also met him but he had a busy job at our government, so they only would have appointments on Thursdays and sometimes in the weekend on a Sunday. This was a good sexual extra for my wife but less intense that the first guy. Sadly this guy did get a promotion abroad in Portugal on the embassy there … so it stopped again … four month later she found a guy again by chatting online and he’s married but still my ex wife’s lover since spring 2016 … in 2017 and 2018 my wife told me that she wanted to life alone with sometimes her lover, but she felt no more warm feelings for me in a sexual way. She still loved me but more as a brother not as a hubby. This with my need of crossdressing, although I suppressed it hard made her wish us to break up and get happy without each other. I wasn’t on the same page because I didn’t understand it at all … why would she … I gave her freedom to have affairs, I didn’t have any affairs. But okay our sex-life became dried up … she didn’t gave me details about her fucking around and it became obvious that we were drifting out off each other.
After two years of trying to repair our relationship I agreed with tears in my eyes that I wanted her to be completely free … I went to my mothers home for half a year to see it this really was what she wanted and after that I came home she still felt this way and we decided to sell our house and since 5 month we are almost divorced (a new law starting at January 2020 about support is better for both, so in two month our request for divorce is a reality. But we are living both after the selling of our home not longer together.
Since four month I found a real nice lady in Amsterdam and we first visited and dated together and I told her my life and she hers to me … although we didn’t mention it on our account on the dating site we are a match like if Heaven has something to do with it. Sexually we are a perfect match … me being dominant in real life but submissive in the bedroom or better at home. And her being dominant all her life but never understood to use this power in her relationships …
On my birthday this year I did live with her permanently and the weeks before we agreed to a FLR lifestyle relationship. So she is my Domina or Mistress for the coming year (24/6/365) … we agreed on that … we also agreed her to be free and cuckold me if she wanted, to me getting in chastity often … and to the feminization or more to sissify me … dear Mrs Dede, I’m so happy that I can be who I am … that’s a men but also a sissy, I feel also the need to be feminine. Where this stops or where to it leads we both don’t know or have planned at all. On my birthday my new women and mistress gave me a chastity device the BON4 silicone. Since 13/10/2019 I’ve been 4 times in this chastity … first time was just 2 days but the second time it was doubled for 4 days. Than the third time I was free 4 days because we started a game with three garbles every Sunday a had to pull out one garble out off a dark velvet bag from the BON4, so the last three days before the next Sunday I had to put my tiny one into chastity again. The game works as following: One garble is red, one black and one is pink. There is also one dice 🎲 in the bag … I’ve to pick one garble every Sunday. When pick the black garble from the sack, I’ve to get the same evening before I go to sleep 😴 i have to put my cock into my chastity device. The amount of days is 1 plus the eyes of the dice my mistress throws. So minimum 2 days and maximum 7 days … the pink garble is how long I’m free without chastity but also the eyes of the dice decide minimum 2 days maximum 7 days … the rest of the week I have to put my tiny one again in chaste … with the red garble, we decided that there could be a wish … when mistress throws the 1-3-5 eyes on the dice it’s her wish and if she is throwing 2-4-6 it’s my turn, I can do a wish within this one week frame. Next Sunday it starts all over again. So the third week I was lucky I was only 2 days in my chastity, 1 plus 1 eye of the dice. But it became 3 days, 1 day extra as a punishment. The next time it was 3 days but on the second day I got 4 days extra punishment and that made it 7 days in chastity … last Sunday I pulled the red one and she throws a 5, so she made a wish … that was me to get every evening teased by her and master-bate myself and ask on the last moment if I was allowed to cum … two days she says … Yes, I may … and I shot my cum all over my belly on my chest and belly. It was really nice. But last night I asked her at almost the point of no return if I was allowed to cum and she said … No, I wasn’t allowed 😳. I had to stop immediately. I was so horny, dear Mrs Dede, I just stroke twice times more on my almost fully hard penis and then when she commanded me STOP NOW. I let my penis go … ☺️ but after 15 seconds my penis has a ruined orgasm and gave my sperm anyway. My Mistress (her nickname is Femme PrimaDonna Cheetha) was quit at first … I looked her in the eyes and began to laugh nervously. She stared at me without a smile back and said I had to eat my cum … she ordered me to eat all of it and said while I did eat my own cum … that I had to go shower this morning and get into chastity again till next Friday the day we will go for a short trip to Belgium to visit a girlfriend of hers. 😒 that’s 10 days in a row.
In your question about Sissy alert you asked to photograph the things I had bought to get more sissified … I will make a photo of my BON4 (this morning I got in it again till 29th of October 😏), I can photograph my new high heels 👠 and I bought with consent of my mistress 7 women panties … I wear them during the days I’m not in chastity because I’ve to use a Tena Men (kind of cotton to catch drops of my urine when using the BON4 … otherwise I have a wet spot on the outside of my trousers. The Tena Men with the BON4 is to full in a women’s Panty … so Mistress Cheetha decides that I’ve to wear panties when I’m not in chastity. The last item is a nice black satin French nightwear for in bed … this I’ve to use with or without the chastity because my Mistress Cheetha wants to feel my butt and private parts in this lovely soft satin when she touches me right there.
Sissy ToyBoy Lievie (my nickname)