Life of a sissy cuckold slave

[SissyBridget]

The start of it all:

For the last 14 years of a 30 year marriage I have been a cuckold. When I look back on how I evolved into one I can see all the things that happened along the way that led to me becoming what I am. What I was likely born to have become.

This dates back to when I was a 3 year old boy and my sister who was 3 years older than me, used to dress me up for her tea parties. I was always in some fairy princess outfit of hers from a past Halloween or one of her tutus and leotards from her dance classes. I can remember how good it felt even way back then. My dad eventually made her stop dressing me but a few years later I found my way into her dresser and closet along with my mom's things and started dressing up every chance I got. This escalated into my teenage years when my mom went to work at Macy's in the afternoons and I usually had the house to myself. I would dress up and prance in front of a mirror and once I started masturbating there was never a time when I was not wearing something feminine. Other boys were jacking off to Playboy magazine fantasizing about girls but me? I was in my sister's nightie and usually was thinking about men. I guess this was all in my DNA from the start.

When I was a freshman in high school my sister came home and caught me in her cheerleader uniform and she freaked out. She threatened to tell my parents unless I started doing her chores and washing her car. For a full year before she moved away to college I became her slave doing anything she told me to. When I look back this was really my first experience with being dominated by a woman. She went away to school and when she came home the next summer she tearfully apologized to me saying how mean she had been and asked me if I was still dressing. I told her I was and she helped me get makeup, some outfits and lingerie, and even gave me some of her stuff too. She went from being my worst enemy to my best friend. However I believe that year really changed me internally and I was never quite the same again.

I was always a great athlete in HS and got a scholarship to play college baseball at UCLA. That was the only time I didnt dress because I lived in a frat house filled with jocks. But as soon as I got home it started all over again. I kept denying that I was feminine because I was a good looking young stud and never was there a shortage of girls around me. I started fucking a lot of hot girls thinking it would distract me from wearing things but it didnt. Those feelings came back stronger than ever. This continued for many years and when I met Julie when I was 23 and she had just turned 18 I knew I was in love. HOT strawberry blonde with a killer body, beautiful face, perfect breasts, and a virgin! We started dating, got engaged, and got married two years later. I was her prince and she was my princess. That was 1986.

Flash forward to two years later. Julie was working at an upscale mall in the bay area and was the most beautiful girl working there. She would always wear sexy short skirts and dresses with low cut tops and men would literally fall all over themselves looking at her and flirting with her. I got used to it because it was so common. But there was this one man who worked in a store across from hers named Joe. Joe was a good looking and charming man and did he ever have the hots for Julie. I did not like him for that reason. Julie often went out with some girlfriends of hers from the mall and they would go to a Tony Roma's restaurant near the mall to have some drinks and listen to the band. I was in a grocery store earlier that day when she was going to go out n and ran into one of her girlfriends and I said "big night tonight at Tony's?" to which she replied "no we had to cancel because no one could make it". II called Julie and asked if she was going out and she said yes...I was suspicious and decided to go to the mall at closing time.

I arrived at the mall and parked a hundred yards or so away from her car and watched as she walked out about 9:15. She was strutting as usual and looking hot. When she got to her car another car pulled up alongside and she leaned in and talked for a second, then got in her car and followed the other car out of the lot. I followed both of them. They pulled into the lot and I pulled into an adjacent lot next to the restaurant, got out, and walked to a large row of oleander bushes between the two lots. I got to a place near the back of the lot where I could see but was not easily seen myself and saw Julie go from her car to the other car that just parked 15 years from where I was. I looked when she got in and it was Joe. My heart jumped as I was wondering what the fuck was going on...but really I already knew...she was cheating on me. They immediately started kissing and kissing deeply. Joe''s hands were all over her and my brain was screaming at me to go to the car, pull Joe out, and beat the shit out of him. But I was frozen...why? I didn't know but just kept watching. After a few minutes I see her head go into Joe's lap and I know that my bride is about to suck his cock. I see Joe's head lean back and his mouth open and know he was now feeling the pleasure that my wife is so good at giving. She is amazing at sucking cock.

I still do not move and suddenly realize that my cock is rock hard in my jeans! Like the hardest I have ever been! This has me more confused than anything but I also realize I am rubbing my hard cock while watching! I then see Joe's face twist up and can tell the exact moment my wife tasted his seed. She gets up, fixes her makeup, and they go inside holding hands. I think the hand holding made me more mad than the blowjob. Not knowing what to do I decide to go home. I got in bed but could not sleep and then as I think about what I saw I start stroking my cock before getting mad at myself for doing that. At 2:12, the bedroom door opens and she strips down to her panties and gets in bed thinking I am asleep. I am now wondering what she had been doing all this time but had my suspicions.

I rolled over and started cuddling with her acting like I wanted to fool around but she said she was too tired, however I didnt let that stop me. I started kissing her back and working my way down to her pussy and she was doing her best to fight me off and I could smell Joe's cologne all over her. I got to her pussy and pulled off her panties and she stopped saying no because she knew I was going to go there. I look back and wonder if she suddenly got turned on knowing I was going to eat her after Joe had fucked her. Once I got there I knew Joe had fucked her. I could see even in the dimly lit room that her panties were soaked and the gusset was covered in his cum. I put my face to her soaking wet pussy and dived in. Her pussy smelled of sex and as soon as I started sucking on her clit I felt a glob of Joe's cum fill my mouth. I got so turned on and wanted more. I was like an animal and she was cumming so hard, no doubt thinking that her husband was eating her lover's cum and thinking I did not know. I finally came up for air and put my cock at her pussy and thrusted inside. I pumped in and out and her pussy was so wet. The thought of my cock sliding in and around Joe's cum made me so lustful and then when I looked down at my beautiful wife and realized that this was the view Joe just saw and how naughty she had been I could not last any longer. I literally came in a minute.

This was 14 years before we became a cuckold couple and to this day even though we are a cuckold couple I have never told her that I know she cheated on me with Joe. After that I started masturbating when she went out thinking that she might be fucking him. So in retrospect I guess I was a cuckold before I even knew what a cuckold was.

In my next posting I will detail how me becoming a cuckold and her becoming my Mistress happened.

The next step:

We explored a lot sexually prior to any of this happening. We had a 3sum with a beautiful girl first. I loved it and my wife did not. I think she was being too guarded and did not let herself go when she was with the other woman. It was really hot watching them kiss and eat each other. At least to me it was. Then we had a 3sum with a man and that was pretty good. Not great but she saw me suck his cock and that was a first. He fucked her but he was not that great sexually. In between we played around with a double ended dildo which was hot, and one time she put stockings on me because she wanted to see how my legs looked in them and she was pissed because she thought my legs were better looking in them than hers, lol. She also saw how turned on I was with them on so another time she put them on me again and asked me to put on one of her baby doll nighties. I acted like I didnt want to and then relented and she again saw how hard I got.

So it was lots of baby steps. In fact this all really kicked off when one night on our front porch we were sharing a bottle of wine and she said "tell me your deepest darkest secret and I will tell you mine"...BIG words. So I said ok and told her about my desires to dress fully with a wig and makeup and how I thought about it all the time. This was in 2003. What she didnt know is that I had been dressing for ten years and keeping all my things at a store that catered to crossdressers in San Jose that rented out lockers to store things in. Those lockers had 24/7 access and I had been dressing up a lot. But when we moved to the Sacramento area I sold all my stuff (HUGE mistake). So I had to start over.

Her secret was that she had been keeping in touch with a man named Joe she used to work with who was always flirting with her. I never liked him for that reason and others that I can tell you about later. Anyway she and him had been talking and he was coming into town for a visit and she wanted to see him, meaning fuck him, and so we agreed to help each other live out our fantasies. The only problem was that she saw him once and he went back to where he had moved (Detroit) and I kept dressing so now she had no further fantasy to explore and I still did. And one thing you should know is that while she was supporting me, we also had out moments where she would get a little disgusted at my emerging femininity. This is kind of what led to her cuckolding me. As I stated above she never could look at me the same after seeing me dressed, tried having sex with me dressed which was a failure, and discovered that she needed a masculine man to satisfy her.

That was when we agreed to have another 3sum. She met this man online and they chatted for a few weeks before we ended up meeting him. What I didn't know was that he was a Bull. He was telling her how great she could have it by making me her sissy slave and he would become her lover and she wanted to try it but never told me. So we meet this guy at a bar that was pretty empty and dimly lit and he comes to the table, sits next to her, doesn't even look at me or say hi, and just stares at her and talks to her for like 5 minutes! I was feeling so awkward. Then he finally looks at me and says "so I hear you like dressing up like a girl and that you wear panties every day. Are you a faggot?" I was stunned and looked at my wife Julie and she was smiling ear to ear with this devilish look on her face and said "sorry but I told him". He asked me again and I said I wasn't a faggot but did like wearing things. And then he says "oh so you are a sissy faggot" and then he grabs my wife and starts kissing her and she kisses him back. My head was spinning and then he looks at me and says "I like that you are a sissy because then it will be easier for your wife to always choose me over you." Again stunned on my end.

He asks her back to his place and we all go there. As soon as we get in the door he tells me to get on my knees and kiss his boots! I stunned myself by doing what he said! As I did this they started kissing and then they walked away to his bedroom. I got up to follow him and he said "who told you that you could move?" so I got back on my knees and they disappeared into his room. That very moment I changed. Everything changed. I felt so pathetic but was so turned on. I just was humiliated in front of my wife and I was so turned on! Then I hear him call me and I go to his room. My wife is already mostly naked laying on his bed and he tells me to get undressed but to leave my panties on. Then he gets undressed standing next to me. OMG! He was lean and muscular, tan, and hairy chested. Everything I was not. I looked down at myself in my panties and my snow white soft smooth skin looked so...well...feminine compared to him. Then he takes off his underwear and OMG again! His cock was huge! And sticking straight out in front of him! My cock never did that. Then he says "which one of us do you want" to Julie and she actually laughed and said "oh god Paul, come fuck me now." He told me "get on your knees next to the bed and watch how a real man satisfies a woman".

I did and for the next two hours I watched as he fucked her in every conceivable position and then some. I heard her make noises I had never heard her make before and cum so hard like I never saw her cum before. It made me question every time I thought I was satisfying her. She at times was screaming as she came and he was pounding her so hard. He came 3 times in two hours with almost no time in between! When they finally finished she must have cum 100+ times and was laying there exhausted and he said "how was that for you" and she laughed again through her heavy breathing and said "oh my god that was the best sex I ever had in my life"...there it was...she realized I heard that and looked at me and mouthed "I am sorry...I love you". But I knew she was being honest. She was with Paul for two years before they broke up and within a week of that first time she had bought me a chastity device and my cock was locked away. Both of them literally trained me to be their sub. She bought a book about female led marriages and every day she pushed me to become more feminine and submissive.

Next story I will detail how I was literally trained to become a sissy slave and how I became completely emasculated and never allowed to touch my cock for pleasure again.

 

[stad90]

Thank you for sharing. I can't wait to read more.

 

[SissyBridget]

My Training

This is kind of a difficult subject to share because I know so many people fantasize about being a sub or a cuckold or perhaps a sissy slave but it is all fantasy. For most people becoming a true sissy and submissive is more than they can take. Actually doing it in reality creates such a change in a person's head and personality that only a select few can go through it. I believe those people are able to go through what is required because they want it so bad. It is not just a fantasy. It is what they ache for and love. Otherwise most would simply reject the idea when implemented. I am going to share with you some things I have gone through in the last 14 years and for you wanna be subs and sissies out there, especially married men, you have to ask yourself what you would be willing to do and what you would be willing to give up to become and real sub and sissy.
Really, even after her meeting a Bull and he having the best sex she ever had according to her, this all still felt like role play. I was calling my wife Mistress after she met Paul, who I had to call Master, and it still felt like a game. What I didn’t know was that Paul was really really into cuckolding. He wanted the ultimate version of it and knew he had this willing couple that fit perfectly into his desires. He had a beautiful wife who had been a virgin when she met me and suddenly felt the pleasures of another man with a vastly larger cock, and he had a husband in me who was excited about exploring his feminine side. The perfect scenario for his ultimate version of cuckolding. What really pushed it to go from role playing to our lifestyle was when Mistress realized she could control me. Not just in the bedroom but everywhere. Paul told her that she could make me do the dishes, do the laundry, clean the house, cook her meals, and literally bow to her and worship her and that if done right, not only would I do it but would be turned on by it. He was right. He gave her a book about female led marriages and she read it several times. Especially the chapters about training your husband.

The first thing that happened was that I came home from work about two weeks after she first was with Paul and she gave me a present. She was so excited and I unwrapped it to find a male chastity device inside. She said “I want you to wear this so that you cannot touch your cock like a man, cannot cum like a man, and so I can own you 24 hours a day.” She said if you are really good at serving me I may allow you an orgasm every so often.” I was taken aback but really turned on at the thought of my cock being controlled by her. It felt so right for what we were exploring. So I put it on and after a few days of adjustments it was very comfortable. But it was immediately intense. Like most guys I rub my cock all day off and on. In the car, watching TV, whatever. It just feels good and I have done it all my life but suddenly I was unable to. I would reach down and realize that my cock was in a plastic tube and while it was mostly comfortable, it was a constant reminder of being owned. My cock would squirm around inside it’s cage and remind me it was there but untouchable. The first few nights were tough because getting hard really hurt my balls but after time that went away. I decided to call full time chastity “delicious torture” because it is beyond intense not to feel pleasure there but so erotic knowing that someone else controls my ability to get pleasure and cum. Chastity was the first step in breaking me as a male.

Next came our worshiping sessions. It did not matter how long they were but they had to happen every day according to Mistress. She would wear something sexy. It could be a dress showing off her beautiful body, or it could be some lingerie, or sometimes jeans with riding boots, and sometimes just a bra and panties. But always she would sit in this big chair in our bedroom with a riding crop and I would be at her feet. She always made me wear something embarrassing like granny panties or something like pink satin full cut panties with bows and ribbons on them. The worshiping always started with her asking me questions like “do you like wearing those pretty panties” and I would say “yes Mistress” and she would say “do you think any real man would ever wear things like that”. Of course no real man would. She asked me about my cock and how I thought it compared to Master’s cock. I had to answer honestly. I knew it didn’t. She would ask me what I wanted to be and I would answer “a sissy cuckold slave”. There were many more things she said too. Sometimes she would have me stand in front of the mirror and look at what I had on and for some reason that was really tough. Here was my wife forcing me to expose myself to her and myself looking like a total pussy. The emasculation was taking place and it felt really good.

After the verbal part she would make me beg to worship her feet. I was made to lick them and suck her toes, the bottom of her feet and when it got really intense was like our 3rd or 4th session when she got really aggressive and started sticking her foot into my mouth pretty far gagging me. I saw her face get this look like she could do anything she wanted and realized that she really owned me and she started grinding her foot deeper into my mouth and suddenly she had an orgasm! We were both surprised by this and she said that she could not believe she came like that without even touching herself. I told her it was because she felt that power and she said “I think you are right”. During the sessions she would continue to tell me how pathetic I had become as a man and a lover and how I needed to let go of being a man and embrace being a sissy girl. She said “don’t you want to wear pretty things under your clothes every day and be free to be and act like a girl?” I admitted that I did more than anything. She would whip me with the crop as I ate her pussy telling me to do better and that really made her cum. She was drunk with this new found power over me and yes I started doing all the housework, most of the cooking, could not talk back or argue, and started changing. I was becoming a sissy slave.

Master took this to a whole new level. He was an expert at humiliation and making me think different. Many times he would tie my hands to the foot board of the bed pulled wide and then my legs the same way. I always had to have a butt plug in me when he came over and he ended up buying one that was so big it would take me 15 minutes just to get it inside of me. Once seated I could hardly breathe and then had to do chores or serve them. When he tied me to the bed he would spank me before they had sex because Mistress once admitted how wet she got watching him spank me. Gagged and bound I watched some of the best porn I had ever seen except my wife was the star of the movie and I knew that my cock had become nothing more than an afterthought to her. She was falling in love with Paul and only wanted me to be her sissy slave. I knew this was very real and that there was no going back. That is an intense moment for any cuckold. The moment when you could choose to stop being a cuckold but know that your wife won’t stop. That is when a cuckold feels the most pathetic. I felt pathetic.

Every time Master came over he did something new to me. One night he told me to go into our walk in shower and kneel with just my panties on. I did and both he and Mistress came in and she was saying “I don’t want to watch this” and I knew immediately what he was planning to do and I was freaking out. But then all he said was “I want you to pee in your panties now”. I protested but got a slap across the face telling me to shut up and do as I am told. He said “show your Master how devoted you want to be for me”. So I pushed and pushed and finally I soaked my panties. I looked up and they started laughing! I felt the first real pangs of humiliation and being in front of my wife was so powerful. But then my worst fears were imagined when he pulled out his cock and told Mistress to hold it and that he was going to pee on me. I immediately said “I can’t do that” and was ready to bail out not caring what happened but Mistress then looked at me and said “you need to do this for me to show me how much you want to be my sissy slave. I really want you to do this.” It was like a piece of me melted. I felt so weak and realized that I was about to be peed on. She looked down and said “open your mouth sissy” and I did and then I tasted for the first time of many Master’s pee in my mouth and over my body. I felt broken and pitiful and I was. With that they kissed deeply and left me in the shower with Paul telling me to stay there until he told me I could clean up. I then heard them fucking so hard and so fast. They were both intoxicated by what they had just done to me and they both came so much faster than usual. Paul came back in and told me to clean his cock and like the sissy slut that I am I hungrily cleaned every inch. I was then allowed to shower.
The next big thing that happened was him buying a baby monitor and bringing it to our house. He didn’t tell Mistress but he put the transmitting end on her nightstand and hid it from view. He then took me into the spare bedroom where I was starting to sleep a lot because he spent the night so much, and he ordered me to the floor. He had a new toy! Hog tie straps. He pulled my legs and wrists together and hogtied me and then put a ball gag in my mouth. Talk about a helpless feeling. He leaned down and whispered “tonight is going to change you forever and take you further into being our sub.” With that he put the receiving end of the monitor next to my head and left.

I heard them starting to kiss and they were still talking but soon I could hear what sounded like her sucking his cock and him eating her pussy. Soon they were fucking and his body was pounding into her with a slapping noise. This went on for a long time and she was cumming over and over. This was all pretty exciting hearing them this way all helpless and I actually was hard and turned on. I love when I am tied up and helpless. They eventually finished and laid on the bed talking. Paul purposely stared asking her questions about me. He said “how did you feel when you first saw him dressed and acting like a girl?” She never shared those feelings with me really. Wee talked about it but she always acted supportive. But she said “oh my god, I was almost sick. I felt like I lost my husband and felt like my world had been shattered.” I laid there feeling terrible that she felt that way and how I should never have come out. Then she said “he looks too much like a woman. If he was ugly it would have been easier but he is pretty and he acted like a woman too which made it so hard. But I got used to him wanting that and love him so I tried to make it work” and then added that “ultimately it was why I decided too cuckold him. I need a real man in my bed.”
Paul didn’t stop there. He said “what was the sex like before all of this started” and she said “he was always great at foreplay and eating me but he never made me have an orgasm from intercourse. I faked every orgasm he thought I had.” OMG! I laid there stunned. Every single one??? She went on to tell him how she was a virgin when we met and how she didn’t know how a big cock could make her feel. She said “until I felt a big cock I didn’t know what I was missing” and Paul asked “was my cock the first big one you have had?” and she said no there was one other. What??? I felt broken and humiliated. Without missing a beat Paul says “you know he is listening to everything you are saying” and she freaked out and saw the monitor and actually told him “are you fucking kidding me, what are you trying to do?” He said he wanted me to hear honesty from her so he can let go completely and understand that he has never been man enough to please you.”
She came into the room and there I was looking so pathetic gagged and hogtied and she went from coming in to tell me she was sorry to saying “sorry you had to hear that but look at you. This is what you wanted and now you have it so let’s all be what we are. You are my slave and Paul is the husband now. There it was. It was like the final hurdle of actually being a sissy cuckold and for her the start of really being a Mistress and not seeing me as her husband any more. From that night on I fully embraced being a sissy even flaunting it in front of them. I started buying sissy dresses and outfits. Baby blue, pink, purple, and yellow satin everything covered in ribbons, bows, and lace. Wearing them every day under my clothes and loving how they felt against my skin. Sitting in meetings with business associates locked in chastity and feeling the shite stockings gripping my legs and the tight lace bra wrapped around my chest. It felt better than anything I had ever felt in my life. It is in my DNA to be a sissy.

Next I will start sharing some of the hot hot sexual encounters she has had with men.

 

[stad90]

Wow. I'm in a relationship with my mistress and love being "feminized/sissified" but it's not with my wife. I admire you so much to share all of this. Are you sharing this for you or for your wife? Is your wife on Lit?

I cannot imagine the shame and anxiety. Did you have anyone to talk to as you were dealing with it all?

 

[SissyBridget]

I love sharing all of this. There are very few outlets to be able to tell others what I have been through and continue to go through but there is zero shame or anxiety now for me or her. We chose this lifestyle and love it but in order to get to where each of us wanted to be she needed to learn to be dominant and I needed to learn how to be submissive. I am naturally a sub but never was a practicing one prior to being trained. It really was a true training where I changed a little more every day. And what I found out was that words are more powerful than physical action, although both work together extremely well, and that the words are at their most powerful when you know that your wife means them and isn't just playing a game. For instance at first she would call me sissy a lot but later as she became more of a Domme we would be somewhere like in a store and she would say something like "do you know how pathetic your cock is too me now sissy? It is a worthless reminder of when you pretended to be a man." And I knew she meant it. BIG difference. And no she is not on Lit. She is living Lit, lol.

 

[Experimemt626q]

I love sharing all of this. There are very few outlets to be able to tell others what I have been through and continue to go through but there is zero shame or anxiety now for me or her. We chose this lifestyle and love it but in order to get to where each of us wanted to be she needed to learn to be dominant and I needed to learn how to be submissive. I am naturally a sub but never was a practicing one prior to being trained. It really was a true training where I changed a little more every day. And what I found out was that words are more powerful than physical action, although both work together extremely well, and that the words are at their most powerful when you know that your wife means them and isn't just playing a game. For instance at first she would call me sissy a lot but later as she became more of a Domme we would be somewhere like in a store and she would say something like "do you know how pathetic your cock is too me now sissy? It is a worthless reminder of when you pretended to be a man." And I knew she meant it. BIG difference. And no she is not on Lit. She is living Lit, lol.

The intricate detail is nothing short of fascinating. You're right, many men fantasize about it, but few (myself included) could handle that kind of rejection. Patiently waiting to read more...