Wedding Dress Enlightenment Pt. 01

I had always been straight all my life. Me and my childhood sweetheart, Julia, got married when we were 21 years old and had always had a fantastic sex life. When we were 24, Julia and her best friend Sophia passed away in a car accident. Sophia was due to marry my best friend Stevie in a couple of months, so we were both now going through the grieving process.

Some quick background into our appearances. I have got kind of long-ish naturally curly hair for a guy, with a medium sized built body. Not stick thin, but not fat either. If I was a woman, curvy would be the term that could possibly be used. Stevie had relatively short straight black hair which goes round into a beard, and has a similar build to me although he had much more muscle.

Now we fast forward 4 months from the crash which is where the story picks up...

Stevie had his house up for sale as he couldn't face living there alone after all the memories he had made with Sophia. he gave me a call. " Yo Jay, can you give me a hand in going through some of the things in this house and getting together what is being kept?"

"Sure no worries man ill be over shortly" I replied, and off i went to Stevie's place.

Whilst we were going through the store cupboards we came to a halt when I pulled out a big box which had a zip on it. Stevie just stared at it and sighed. The box had a big label on it which read "The Bridal Outlet". "So that's where she was hiding her dress" Stevie said with an upset look on his face. I unzipped the box and had a quick peek inside. "Oh wow!" I exclaimed. I only saw the contents for a very short time but what I did see was a dress with a big bushed out skirt to it, and some white stilettos that had heels about 2-3 inches in size.

"It is criminal that you haven't had the chance to see this warn yet." As i said that I had a lightbulb moment. "What if just as a one off, I arrange to model this for Stevie. Me and Sophia were similar heights and build so in theory it should fit me okay?" I thought to myself. This was my first ever thought of crossdressing, although it never clicked with me that that was what this was. I just saw it as me doing a nice thing for a friend. I revealed the idea to my best friend which caused him to be silent for a couple of minutes, which felt like a lifetime.

"Erm... Go on then" he said, "it will be nice for me to be able to imagine what she would have looked like in it." I picked up the box and left with it. "Leave it with me mate, you make sure your suit is ready, and I will text you the details. I will organise us a location."

"Hey sister, I need a hand with something but hear me out first" I said to my older sister over the phone. She had her own beauty salon and was skilled in all aspects of it. "Come round to my house at around 7:30 tonight I have something to show you that I need help with."

7:30 soon came around and Kim showed up at my door. I closed the blinds and curtains, and pulled the box into my living room. "Uhh, Jay, Why do you have a wedding dress...?" Kim asked. So I explained the story of my afternoon and my sister's fave kept becoming more shocked. "You're actually going to do this for a friend?! When? Where?."

"I was thinking of booking a hotel room in that boutique hotel outside the city for Saturday night, so then it isn't in one of our houses and it should be a better memory for Stevie. I need you to help me put it on now though so we can see if there is anything that we need to do."

"Hmm okay" Kim seemed to reluctantly agree to helping me out.

Everything was put on. The underneath corset, the suspenders, the white stockings (which were incredibly sexy to me), the wedding dress, and then finally the white gloss high heels. Kim was getting more excited as each layer went on, I could see she was really getting into dressing her little brother up. "You know what Jay, you could actually pull this off! You need your legs waxed, hair done and possibly some extentions in before finally your makeup done. But I could get you looking than a stunning lady I reckon." Kim said excitedly, it seemed like she was well on board with this little project now. I turned and looked at myself in the mirror. I concentrated on the neck down, especially the parts of nylon that I could see and I started to feel my cock grow. I tried to disguise it the best I could so that my sister hopefully would not notice. Part of me felt disgusted with myself, but the biggest part of myself felt exhilarated. This was such a taboo, it was wrong, it was naughty, but I hadn't had such a good feeling this in years. This was a sexy wedding dress, and here I was wearing it.

"Jay? JAY?!" Kim shouted and I snapped out of my trance. "Stop checking yourself out you naughty boy" she said playfully.

"Shut up" I snapped back, "I was just looking at if I actually pull this off and don't just look like a man in a dress."

"I'm being honest you actually don't look bad, once we've had you in the salon I don't think anybody will know that you're a man, maybe even not Stevie! I'll give you a call tomorrow once I've checked the diary at work, and we can get you booked in." And we then removed all of the clothing and put it back into the box.

When i got into bed that night I found myself searching for porn involving wedding dresses. I stroked my cock and climaxed to a video of a bride on her knees on her wedding night sucking the cock of her husband. After I had climaxed I did have a vision that the bride in the video was myself however I quickly shook this thought off and went to sleep.

I woke up and looked at my mobile phone. I had a message from Kim. "Diary for Saturday has been cleared. I have Jaymie booked in all day for a bridal makeover. See you on Saturday! X

"Thanks sis. X" I replied as I went back into a trance of thinking about myself in the wedding dress. I found myself getting more heated and the next thing I realised was I was wanking aggresively. "Oh Jaymie Oh Jaymie" came out of my mouth as I reached my orgasm and sprayed all over my chest. I didn't know what that was or where it came from, but it sure felt great...