success

Well I haven't posted in quite a while, my last effort was a, just for fun fantasy to see if I could write one.

This time I have some real news that I hope will be of interest to some – I have been dabbling with my sissy cross dresser desires for a little while now, with quite a nice selection of lingerie and lately dresses, wigs, heels etc and prancing around the house in private. Very much in the closet and for the most part needed to remain so, however I was very interested in going "out" if I could do so without jeopardising my job etc.

I recently read an article about sugar daddy sites and people making arrangements with woman for liaisons etc – well, I thought, why not put a profile up saying I was looking for a dominate woman to help me experiment with my feminine side and cross dressing desires. To my surprise, I got a lot of response (such a site is actually refreshingly honest as everybody there is quite up front with their expectations from both sides "i'm looking for a dom woman to take me lingerie shopping..." - "yes I'll do that for this arrangement" sort of thing, for the most part non-judgemental, civilised and mature I thought really)

I'm very pleased to say I have found a wonderful Mistress in a city a couple of hours drive away, that knew exactly what was needed and an appointment was made (the distant city should provide the anonymity I required to have some cross dressing fun, without being found out by someone I might know in my smaller town) We discussed what scenarios and roles could be played out, but it was left to my new Mistress to "surprise" me with what activities she had in mind for our first encounter a couple of weeks ago

We initially meet for lunch and I was instantly smitten by the exquisite woman, after getting to know each other for an hour or so, M advised it was time to begin my adventure for the day. We wandered down the
street, still chatting, when M stopped and motioned me into a lingerie store, we were quickly meet by a very friendly sales assistant, greeting us which "hi how can I help you, looking for anything special?" M replied "well it's a little embarrassing..... but I caught my husband wearing my underwear and trying my clothes
on.......if he wants to be a girl, we better get him his own lingerie" playing the somewhat indignant wife to perfection. The assistant was extremely professional "oh yes, don't be embarrassed, we have lots of men in here buying lingerie, it is far more common than you night think" and helped select a number of sets and even suggested trying them on and she would check the fit etc. I spent the next half an hour in the changing room trying on bras for my "wife" and the assistants approval

What an experience, my "wife" made me buy a weeks' worth of bra and pantie sets informing the lovely assistant that would be enough to replace all my old male underwear, the assistant enthusiastically offered her
support saying "it's fantastic its out in the open, your relationship will be even better now that you can have him wearing lingerie every day"

Next, it was down the street a little, to a mall and into another lingerie shop, this time to buy some slips and nighties, again the assistant was very supportive of my "wife's" predicament as I tried on a number
of pretty satin and lace slips.

We then went to the hotel room I had booked and M had me put my lingerie, stocking etc on and then show her the selection of dresses and skirts I had brought with me, along with a couple of wigs. M settled on a black pencil skirt, black and white floral patterned blouse, black peplum jacket, black 3" heels and a brunette wig. "hmmm you look lovely but you need your makeup done, I have made an appointment for you, we need to go" and with that I was being escorted down the hall and out to her car.

Next thing we are back at the mall and walking into a large department store and arrive at one of the Brand counters. M introduces me to the beautician "Hello again, this is my husband, I was telling you about him wanting to dress up as a girl, we need his makeup done as I arranged"

So in the middle of the store I am sitting getting my makeup done, customers wandering past as the application started to transform my look. I started to feel very much that I could walk out of the store as a woman. Which
as it turned out, I was going to have to as M had more planned. After buying some makeup product to maintain my new look we went for a wander around the mall stopping at dress shops and even had to buy a new ladies wallet as I had used my old male wallet when I paid for the make up and beautician had comment that it would be a bit of a give away continuing to use it!! Then M advised we had another stop to make and headed back to the car.

It was early evening by now as we drove a short distance and found a park "here we are, this is a nice bar, shall we have a ***** and a snack" well I had given M total control and it was too late to chicken out now. We entered the bar which was quite full with an after work, business type crowd, and mostly men I must say, M was definitely having fun with her new sissy!! We ordered a ***** at the bar and then found a table, a little later a, waitress approached "hello ladies, would you like some menus?" What a marvellous evening we had, even going to the ladies room together to touch up our lipstick, before leaving and M taking me back to the hotel, a chat about the evening and some strict rules and instructions if our meeting were to continue - put simply M would be in total control and I would obey all instruction from now on - of coarse I was more than happy to say comply.

Since then M has been in text contact with me almost daily, telling me what lingerie to wear under my work clothes each day and sometime teasing me about how well my little dick fits into women's panties or about how much see enjoyed one of her well hung lovers the night before etc .

We have arranged another meeting in a weeks' time and she is threating to introduce me to one of her lovers, she refers to him as her "alpha man" and let me witness what a real man can do with her, but I suspect there may be a bit more to her plan that just watching!

I can only say, it is the best thing I have ever done, so if you have any thoughts about wanting to try something like this, I can assure you its worth the time, effort and expense

Wow, that's a fantastic story. Glad you found what you're looking for. Love to hear more as your experience develops.

I will update after next week end.