Hello! My name is Bridget and this is my second time on Flickr. I wandered away the first time after many years and now I am back! I am a crossdresser, am bisexual, am married to an amazing woman who has supported Bridget and loves me this way but she also made me a cuckold and put me in chastity as part of the deal. I love my life and am blessed in so many ways.

I started dressing around age 7. My sister was 4 years older than me and I would try on her things constantly as well as my mom's stuff too. I have no idea why but I loved it. I usually had the house to myself in the afternoons after school growing up. Dad was working and my mom had a part time job in the afternoons at a local department store. My two older brothers moved out when I was still young and my sister was always at her friend's house so I would come home after school and dress, prance, and look at myself in the full length closet door mirrors in my parent's room.

I only stopped when I was away at college at UCLA. The first summer I was home from school my parents went on a long vacation and invited me to join them but I just wanted to stay at home and dress and be a girl. I ended up meeting an older man one night and went to his house dressed and lost my back door virginity to him at age 19. It was an amazing experience and I loved being in the female role sexually. Despite that great time when I saw that man 4 times, I met the hottest young thing I had ever seen after I graduated. Her name was Julie. Petite, incredible body, strawberry blonde hair, killer green eyes, and the prettiest face I had ever seen. We dated and married two years later. She knew nothing about this side of me.

Our marriage was great and the sex was amazing. We explored a lot with toys and role play, and ended up having 3sums with men and my wife saw me being sexual with men for the first time and it actually turned her on! And I got to see my wife enjoying men who were far more blessed than I was down there if you get my drift and wow, did she ever love the extra size. It made me feel kind of inadequate though. Nature simply did not give me the equipment that these other men had and my wife loved, no LOVED it! That foreshadowed what was to come.

One night over two bottles of wine on our front porch my wife said "tell me your deepest darkest secret and I will tell you mine. No judgement". So I told her I wanted to try crossdressing with a wig and makeup. What my wife did not know then was that when we had lived in San Jose, I had found this store that catered to CD's which had lockers for rent with 24 hour access. It was heaven for me and for many years I was dressing and going out all the time so my makeup skills were good by the time I came out to her.

Her secret was that she had been keeping in touch with an ex co-worker of hers who had moved out of the area and was coming into town for a visit and she wanted to see him. I said "you mean you want to f*ck him?" and she said yes. So we agreed to help each other with our mutual desires. She spent a weekend with him and I was pretty jealous but she came home and we had great sex and she brought something home for me to eat, if you get that drift too. I went wild and ate every drop and she loved me doing that. I have done it so many times since and every time is so incredible.

Then we went shopping together and bought a wig, makeup, and some lingerie for me to wear the next weekend. She was shocked when she saw me looking so much like a female and I acted very feminine too which shocked her even more. She actually pegged me that night and the next day she told me it was like I was a different person and then she admitted days later that she could not unsee me as a female and said she had lost some if her sexual desires for me as a man.

I told her I would quit and I cried begging her not to leave me but she hugged me, told me she loved me, and said we would figure something out. That was when she started reading about female led marriages and cuckolding. She asked me if I would consider becoming submissive to her and being her "sissy slave" at home, telling me I would wear panties every day and dress often but that it would not be role play. She would be in charge and I would do as I was told. I agreed but had no idea about the cuckolding at that time. She trained me for 3 months, every day in some form or another. emasculating me and when I talked back or argued she punished me and it was very intense. 3 months in and I had become a true sissy servant for her and was very emasculated.

Then one day she asked me if I knew what a cuckold was and I said no so she told me to go look it up because if all went well that night I was about to become one. We met a very intense and masculine man for a drink and ended up in his bedroom that night where I watched on the floor on my knees next to the bed and saw my beautiful wife going wild with this hot hung man who did things to her and for her that I could not. I knew things would never be the same. That was on February 7th, 2003. Two weeks later she gave me the first of many chastity cages to follow and I became a sissy cuckold kept in full time chastity ever since.

There have been so many men along the way and today she is in love and committed to an amazing man for the last 4 years. I am their dutiful sissy and the best part? In 2014 she let me start seeing and dating men on my own! That has been equally incredible! That's my life story!