I will start this off by saying that I wasn't always a sissy. I have always been submissive when it comes to women but the thought of dressing in women's clothing wasn't something that turned me on.
It all started off innocently... a relationship with a kinky woman and her wanting us to take our relationship to new sexual heights. While it took some convincing, eventually she was able to get me to admit that I got extremely turned on by a woman wearing furs and boots and that I had a great affinity for the touch of fur and cashmere, the smell of leather and perfume, and I fantasized about a woman making me pleasure her repeatedly.
This lead to some great sex and to this day I still love to bury my face in a woman's fur collar and kiss her neck while I'm intoxicated by her perfume while she gently caresses my face with a gloved hand. However, nothing could have prepared me for what was to follow. After several weeks and shortly following our conversation about clothing (see the comfort and pleasure post) she asked me why I didn't own or wear any fur since she knew I enjoyed its touch. My response was that almost all the fur out there was only available in women's clothing and that a men's fur coat didn't fit my style or budget nor was it really an acceptable fashion in most cases.
She told me that was stupid and could tell that I was a bit embarrassed. She then asked me if I would be willing to wear fur in private while around her in the house or in the car and I could take it off before we got out of the car if we were going someplace. I reluctantly agreed, she was immediately happy, and we went out shopping the next day. We visited a couple of department stores and she picked out a variety of items that we purchased including a long fur scarf, a fur tie on collar, a pair of leather gloves lined with fur and with fur cuffs, a fur headband, a pair of fur earmuffs, a knit hat with a fur trim, a pair of fur cuffs meant to embellish a sweater or coat, and fur muff. She tried on every item and modeled it for me, every so often teasing me by gently rubbing my face with the fur. She was giggling the whole time and it was obviously turning her on to tease me. I was pretty much silent, blushing, and also very turned on.
I was a bit uneasy at all of the things we were picking out, many of which were way too feminine to be considered unisex (even though they were all black). I could tell she had planned to pick up a large variety of things from the start and when she made up her mind, that's how it would happen. If I questioned something she said that it was for her and for me not to get worried about it.
Upon returning home she had me undress and put on the long scarf, gloves, and hat. She put on a few other items (as well as some she already had) and we had some amazing sex. Life didn't change too much but she wanted me to wear the scarf whenever we were at home (including while I slept) and when we were in the car together. It started to feel a bit normal.
Around this time our relationship had grown very serious and she dropped a bit of information on me that changed my life forever. She had spent several years active in the BDSM scene and didn't want to live a life without kink. She had mostly been a submissive but had done some dominating and that too had "done it" for her. She spent a lot of time describing to me that I was a natural submissive and overall, it turned me on a lot to think of her tying me up and having kinky sex. By the end of the conversation, it was decided: I was going to be her submissive lover and we were going to practice BDSM as a lifestyle.
The whole experience was very exhilarating. I loved her more than ever and the sex was unmatched. I felt safe knowing she loved me and wouldn't leave me as long as things stayed on course. She was getting her fix and we were reaching a level of closeness I had never experienced before with a woman. Her personality grew very dominant and she developed a very strict set of rules for our daily life that I was to follow to a T or be punished. In all honesty, that turned me on a lot and made me love her more and I realized that I really was a very submissive person.
Things didn't stay great forever. She developed some health issues and I ran into some troubles with finances, work, and school, all of which raised the stress level of our relationship. We began to argue and fight for the first time in our relationship.
She would get angry with me and instead of talking through our problems she began to default to her Femdom state whenever any problem would arise. Her punishments were three-pronged: emotional, sexual, and physical. Usually it followed a process of time out followed by forced masturbation with orgasm denial (often leading to painful blue balls for an extended period) and then some corporal punishment.
It was during this time that fur and women's clothing became part of the punishment. She began buying extremely girly panties (usually "ruffle butt" style) and very feminine fur items. A regular time out might have me kneeling in the corner for a few hours wearing a pair of pink panties, pink mittens with pink fur cuffs, a pink fur scarf, a pink hat, and a pair of pink fur earmuffs (although she would change up the clothing each time). When the time was up she would enter the room, face me towards a mirror, force me to look at myself, and order me to masturbate without cumming for an extended period of time. While that was happening she would call me a sissy and tease me about masturbating while dressed in women's clothes and fur. After several days of blue balls and I was finally permitted relief, my orgasms were performed while dressed up in a punishment outfit and masturbating in front of a mirror while she would harass me verbally.
The outside factors causing stress in our relationship steadily grew worse and our relationship grew more and more toxic and with each argument her punishments grew more and more severe. During the final months of our relationship my only orgasms occurred while she had me dressed up in girly clothes and furs while looking in the mirror and her words humiliating and embarrassing me. Girly is a better adjective than feminine since everything was colored in pinks, lavenders, fuschias, etc. and consisted of items that many women won't wear (ear muffs, hats with huge pom poms, fuzzy mittens, etc.).
Our relationship ended in a rather bad way that was quite painful.
Later I would find that this was only the beginning.
To be continued.