How I became a sissy

I have since "replaced" this with a more thorough and complete version:
My Journey into the Lifestyle

I will leave the original post below as it was from 2010.

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The Making of a sissy

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.
After the difficult end to that relationship I had made a decision to continue on within the BDSM lifestyle.  I spent some time in our local scene and several months later I met a very intriguing Domme at a local event.  We hit it off pretty well and soon after I found myself in regular contact courting her.

She was quite a bit different than other women I had known, including my ex.  Unlike my ex, this woman's dominance ran deep and completely to her core.  She didn't just enjoy the kinky aspects of the lifestyle, she thrived on Femdom and making men suffer in pretty much every way imaginable.  At the same time, she was a very caring and loving person.  While I probably should have approached with caution, I threw caution to the wind and dove in head first.

During our courting period she asked me many questions about my previous experiences and wanted to know all of my deepest, darkest secrets and desires.  When I told her about the punishments I had been receiving late in my previous relationship she could sense the great shame and humiliation it brought me while recounting those experiences and that drove her completely wild.  She also happened to love fur and it turned her on.

I must have made a good impression because within a couple of weeks we began seeing each other regularly.  Our times were split between going out shopping together or staying in for body worship and play.  Although she had been part of the BDSM scene for a long time, forced feminization was new territory for her but she thrived upon it and took great pleasure in shopping with me. 

She also had very few inhibitions about making things obvious in public.  I still have rather vivid memories of an outing to a department store where we found this exact hat during the Christmas season.  She put it on my head and made me model it for her with around a dozen women present within 20 feet of us.  She told the sales clerk that she didn't trust mirrors so it was better to have me wear it for her.

  
I can't remember another time where I was blushing so profusely and I was barely able to speak the rest of the day.

During our private times she was a firm believer in exerting control over my sexual activities.  Masturbation was only permitted with her present and I wasn't allowed to ejaculate during sex.  Continuing on with the later trends of my ex, I was only allowed orgasm while dressed in women's clothing but she took things a step further, adding sweaters, skirts, and stockings in addition to items similar to what my ex had used.  My masturbation outfit became a pink angora turtleneck sweater, a pair of pink satin panties, pink fishnet stockings, a fuschia micro skirt (that was so short it wouldn't cover my butt or genitals), a pink wool hat with a sparkly sequined snow flake on it and a large dangling pom pom from the top, a pair of huge pink fox fur earmuffs, a pink fur scarf, and a pair of pink wool mittens with fur cuffs.

She too would order me to masturbate while looking in a mirror while she watched over my shoulder and would tease my nipples and emasculate me verbally until I was nearly in tears.  This would continue for 45+ minutes until I was granted permission to cum.

What she was accounting for and I had failed to account for was that after 2 years of only being allowed to cum in this fashion, her goal was to condition my sexual response.  This became increasingly apparent when she introduced chastity devices into the mix after the first year and stopped having sex with me.  At first she would wait to remove the device until after I was dressed but after several months she started removing the device before I was dressed.  The first time she did this she noticed that I wasn't instantly hard upon the device's removal but once I started getting dressed I had a raging erection.  When I was completely dressed she ordered me to masturbate and then hissed in my ear that she had "ruined" me and that now I wouldn't be able to get hard unless I was dressed as a sissy.  I began to cry but she insisted I shouldn't worry because we would be together forever.

By this time we had made plans to live together and she began laying down ground rules for this to happen (chastity, dressed fully in women's clothing when home, etc.).  Soon after a few major events happened in each of our lives and we ended up parting ways when she relocated.

It donned on me then that things would be much more difficult for me from there on out.  Normal sex doesn't do it for me.  Normal porn doesn't do it for me.  I would only be able to get hard while dressed as a sissy and being humiliated or fantasizing about that. 

4+ years later I feel I have finally come to terms with who I am now.  I am a sissy... and probably always will be.