Planning my first venture out as Sam

Hi girls.

Here's my story.

I've enjoyed crossdressing since I was about 7. My sister is about 5 years older and I can remember borrowing her school leotard and gym skirt when I could. It felt so good to have the material brushing my thighs. Our house was big with three floors and her bedroom was next to mine which made it easier. I ventured on to her minidresses and I'd make a pair of boobs from a couple of t-shirts. This went on all through my teens.

Fast forward to my first house when I lived alone. No internet then, just catalogues to order from. A few purchases later and I have my own, still hidden, wardrobe. I couldn't let any girlfriend find out for fear of losing them. I took every opportunity to get dressed and would stay dressed for entire weekends without leaving the house.

Fast forward again to about 5 years ago. I'd been married for about 15 years by now and had purged all of my clothes. My wife knew nothing apart from that I was not averse to attending a fancy dress as a woman.

The advent of online ordering and the ability to choose a pick up location made my choices so much broader and easier. It was now that I discovered my desire for 50s swing dresses and petticoats. I bought about 5 different style and length dresses with varying petticoats. These only got aired when I was in a hotel somewhere around the country (UK) with work. I became more and more desperate to take my alter ego out and show her to the world...I didn't pluck up the courage.

In a few weeks I am turning 50. We are having a day out with friends. It was on a night out a few days ago with my wife that she suggested I wear a skirt for the day. I'm not sure where it came from but I was quite taken aback. We tentatively discussed outfits and my history then spent the evening picking out my dress. She even said we could get a professional makeup girl to get me ready. WOW.

Now, I must say, It's difficult to find dresses for a 6'5" man that would look good so I have ordered one, with a fluffy petticoat, breast forms and sports bra for the outfit. This morning I visited a dressmaker who is going to lengthen the bodice section and fit a better zip for me. It was awesome standing in the shop donning my dress and chatting about styles and best ways to make it look great.

I CANNOT WAIT to pick it up on Tuesday next week and show my outfit to my wife. I hope she approves.

I'll put some pictures up on here after the day out. I'm going to see if my wife fancies a girly weekend somewhere after so I can get another outfit or two.

Sam gets to go public 🙂