Sissy cuckold

I was always been a crossdresser from a young age obviously it began at a very young age wearing my sisters clothes. I started our wearing ** but progressed overtime to bras stockings suspenders which were more common than tights at that time.

This probably accounts for my preference for stockings and suspenders over tights all though I do wear tights if required by wearing very short skirts etc. That said I do like my stocking tops ad suspenders being exposed in all honesty.

Over the years I continued to dress at every opportunity experimenting with make up wigs more and more feminine clothes skirts blouses dresses etc. I was very drawn to tight fitting dresses skirts tops anything that showed off the outline of my bra or the straps of my suspenders so it was very obvious I was wearing stockings and suspenders. I loved that look as it made me feel very feminine.

I started to perfect my make up added false fingernails and of course varnish eventually painting my toenails as well when I had time and the opportunity. I wanted to be totally feminine in appearance and mannerisms.
I became absolutely comfortable in heels with no problem walking in 4/5 inch heels this does once you have mastered it give you a far more feminine walk and by watching other women I learned how to walk smaller steps accentuating your feminine walk. It’s important to watch women and learn how to act like them when you’re dressed.

All this time thru the years I was a normal heterosexual male and my transvestism remained my secret but I couldn’t stop the desire to dress at every opportunity. The lure of female clothes underwear heels make up etc was as great as ever and I knew it was with me for life.

So I eventually married as convention expected and this brought a completely new set of problems as I still was dressing unbeknownst to my wife obviously so hiding clothes and the opportunity to dress were less frequent especially being able to wear make up paint nails etc which was a lot of effort therefore I wanted to spend as much time as possible in my female alter ego.

Years went by and I managed the situation which was difficult but you learn how to manage your need to to dress and accept your situation.

Our marriage was good we had a solid relationship and it was on an equal basis to start with and we were becoming financially stable with our joint efforts. I had always had a domestic nature so I shared domestic responsibilities with my wife so in many respects our marriage was perfect apart from my secret which I was still engaging in at every opportunity.

My wife was very career minded and over the years she was promoted regularly and was driven to reach higher positions in her company of course with that came salary increases on a regular basis. This helped our financial position even more so and we moved house into a bigger house in a much better area and our lifestyle adjusted accordingly.

A few years later my wife was headhunted by another company and offered a position with them effectively doubling her salary which was now in excess of six figures along with share options private health care company car etc.

It was now at a point where she was earning three times that I was and I for the first time began to feel inadequate which caused me to dress more and more and taking bigger risks. Then the moment came that was about to change my life completely happened.

My wife was supposed to attend a business meeting and be away overnight returning later the following day. This of course was a great opportunity for me and no sooner had she left I phoned work to say I was unwell and began the process of turning myself into my alter ego Michelle.

A few hours later my hair done make up on finger nails on painted along with my toes perfumed I slipped into a beautiful set of underwear. Black lacy bra matching suspender belt ** black seamed stockings which I really like because of the seams running up the back of your legs. I wore a really tight fitting A line black dress I had brought in a charity shop fairly recently it fitted me well once I had padded my bra to a fairly good size as i always liked to look fairy ** when dressed femme. I coupled the dress with a pair of four inch open toed black heels which showed off my painted toes even through my stockings.

Eventually transformed I looked at myself in the mirror completely happy at how I looked and felt. The feeling of my underwear against my skin under my dress was exquisite my bra fitting tightly against my dress suspender straps holding my stockings tightly my seams perfectly straight all things which add to my sense of calm and excitement. Touching up my make up freshening lipstick adding more perfume anything that completed my transformation into a totally feminine picture.

For some hours I did housework wearing a pinny obviously just dusting vacuuming sorting washing putting it on all household tasks I had always carried out as a male but when dressed I found it so much more satisfying as it just added to my personification as carrying out what is considered by most the responsibility of a female entirely I’ve since become to understand that only applies in a certain situation.

After a few hours totally immersed in my female role I made myself some lunch and sat down to watch The Real Housewives of Beverly Hills my favorite TV show. Watching and eating lunch I was totally at ease feeling my stockings on my legs rub against each other and my suspender straps tightening as I crossed my legs I was in total heaven and then 😲😲😲!!!!!

I suddenly heard our front door open and my wife call out “I saw you car in the driveway didn’t you go into work today ? “
I froze in complete fear unable to move thoughts of this is the end of my world unable to exit somewhere that I could escape her attention I braced myself she entered the room and immediately saw me in all my glory.

“Oh my god” she exclaimed upon seeing me”What on earth are you doing dressed like this and why” question after question followed. “Your wearing make up and nail varnish for gods sake how long has this been going on and why are you doing this”

“ I can explain” I said apologetically. “Explain you had better do more than that” my wife said. “ How long has this been happening “ I replied “all my life I’m so sorry” . “Sorry we’ve been married for 11 years and all this time you’ve been doing this” I had a tear running down my cheek as I said “yes I have there’s no point lying to you now I’m so sorry this was never meant to happen”.

“I’m ** sure it wasn’t” she replied. “So all these years I thought I was married to a man it turns out I’m really married to a homosexual that likes wearing women’s clothes make up nail varnish don’t you think that would come as a shock and anger me”

“I’m not homosexual I said I never have been I just enjoy dressing and looking like a women I love the feeling of the clothes and every aspect of being a women” “My good god you certainly don’t do things by half’s do you I hope you not wearing my clothes” “No nothing everything is mine I brought it I promise you I will go and get out of everything ok” my wife looked me up and down and said

“Why do you think that’s going to change this situation you can stay as you are and start explaining everything to me. I want to know everything about this and see if there is any future for us as a married couple” “Are you wearing stockings or are they seamed tights you have on” she asked. “They are stockings I replied I prefer them to tights” She laughed and said “Oh forgive me I should have know my husband prefers stockings as opposed to tights that’s makes all the difference”.

It seemed we sat and talked for hours I explained my life history to my wife from the beginning to this point now and begged her to try to understand and not judge me.

She said I had to understand how shocked. she was and it’s difficult understand that the man you married has a secret like this never mind actually catch him dressed like so. I said I never wanted you to know I thought I could keep it a secret from you. “Well your secret is out now isn’t it “ she replied. “Tell me could you stop doing this”

I told my wife I could tell you yes but it’s been with me most of my life since I was nine years old I know I will always do this at some time or other I understand how bad you feel and I will understand if you don’t see a future for us. “ That’s as maybe I need time to think about everything this situation has a huge impact on our relationship as husband and wife and I need to assess the whole situation and decide what the future holds for us both. “Tell me do you get a sexual feeling from dressing like this way does it excite you sexually”. I told my wife yes yes it’s pointless lying I loved the feeling of it the clothes every aspect of femininity etc.

“That explains why you’re not that good in bed don’t you think” I mean all the times I wear ** lingerie for you your wanting to wear it rather than ** me in it I suppose yes ?”

Mostly yes I replied. “Well at least your honest and it explains why your useless in bed I know your small and can’t control yourself but now I know why it’s because you can’t get passed my underwear isn’t it ? “

I admitted to my wife that was so yes. She said she needed a few days to think about everything and we would discuss it once she had decided how she felt about everything. I won’t cause a problem if you want a divorce I told her. I know you won’t she told me right now you’d not in a position to tell me anything are you really. I suggest you just carry on until I decide the next step do

To be continued

Dec 12
Next Confession

Related Posts

See today's best, hand picked, Amazon deals - Updated daily

No Comments Yet

Account Login
Is this post inapropriate?
Reason for reporting this post
Report this comment
Reason for reporting this comment
Delete this post?