Tagged: First time out
- This topic has 8 replies, 8 voices, and was last updated 4 years ago by Brittney Andrews.
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- September 25, 2018 at 10:57 am #118162
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 🙂
- September 25, 2018 at 11:32 am #118166
You are very lucky to have such a accepting wife.
- September 25, 2018 at 12:13 pm #118172
Sam what a wonderful story , thank you for sharing. “oh yes” the experience of venturing out can’t wait myself. And all the prepping what fun and having your wife there mixing in on the moment. Please tell how it goes I would love to hear. Looking forward to seeing your photos. go get them..
- September 25, 2018 at 12:18 pm #118173
[quote quote=118166]You are very lucky to have such a accepting wife.
[/quote]
Hi Terri,It’s very early days yet so I’m going to take it very slowly. I’ll keep you informed.
Sam x
- September 25, 2018 at 4:05 pm #118205
It would appear that your wife knows you better than you thought, that makes you a very lucky girl.
Definitely approach things slowly, even to the point of letting your wife take the lead.
Best wishes for a fantastic birthday outing.
- September 29, 2018 at 5:43 am #118752Anonymous
Hi Sam I’m “out” tonight literally well and truly all dressed in pink and I hope you as well as me become the girly we want to be. Enjoy Tuesday I’ll try and get back to you to see how you got on. Deborah x
- September 29, 2018 at 7:47 am #118767
Hope it went well for you!
- October 2, 2018 at 6:38 pm #119378
Oh Sam I agree with Sheryl methinks she knows. And yes do go slowly because I made the mistake of trying to move too fast but now she has embraced who I am. I am very lucky and I am thinking so are you! Please do post some pics of your outing. Love ❤️ and hugs 🤗
Danielle💋👠
- September 16, 2019 at 5:57 pm #223584
Sam, Thank you for sharing your dressing history. All I can say is WOW, what a surprise birthday present. You’re extremely lucky that your wife became so supportive out of no where. I hope your relationship has stayed strong. If you haven’t updated about your birthday outing or your wishful girly weekend, it would be great to hear more.
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