Wedding Dress Enlightenment Pt. 02

Within a flash, Saturday had came around and I had woke up with some of the hardest morning wood I had ever experienced. I tried to refrain from touching myself as I got ready to walk to my sister's salon. I put on some denim shorts, a loose t-shirt and set off on my walk.

I got down to the salon to find that Kim had closed it for the day so that it was a private appointment dedicated to my makeover. All 4 members of her staff were there waiting for me. "Don't look so scared Jay, I've told them all the details and not only are they keeping this secret, they are also more than happy to help out as this is a first for them all." Kim said excitedly before grabbing my arm and pulling me into the middle of the shop.

"Okay first off all, we need you to strip down to just your underwear so we can all see what we're dealing with. Don't worry, there is a robe in the changing rooms for you to put on also." Off I walked into the changing rooms to begin getting undressed.

When I emerged I was led into one of the private back rooms which is where the waxing usually takes place. One of my sister's colleagues, Chloe, talked through the process of how she was going to make me hairless. The next 45 minutes were painful but I think I took it like a champ, until it came to the sack and crack. "Is this really necessary?" I asked.

"What? Do you really want to see hair sticking out of your wedding lingerie? Or do you want to look sexy, and also feel sexy when you feel that silk material across your cheeks?" I didn't say anything but my cock twitched a little. "Exactly" Chloe said "It will also look better for him when he's fucking this cute firm arse of yours." She said with a giggle as she ripped off the wax strip. " AHHHH go away!! That will not be happening." I exclaimed. To which Chloe just laughed.

Next I was sat in the hairdressing chair and the silk gown was put over me by my sister. "First of all we're going to wash and condition this hair to make it silky smooth, then it will be brushed out and straightened so we can see what length we're playing with, then a quick hair dye to match these extensions, then we can give you the bridal pin up. Does that sound alright girlie?" Kim smiled whilst passing me a glass of prosecco.

"Work your magic sister." And so she got to work.

Whilst the hair dye was on I was moved to the next area to get some acrylic nails on. Dark red/Maroon was going to be the colour scheme for the wedding so that is the colour nails that we went with. My nails were filed down by the resident nail technician before the acrylics were put on. I couldn't stop scratching myself with them as they felt amazing.

Next up, the hair was washed out and the bridal pin-up was complete, with a strand of curl on each side of my face. Lots of hair spray was applied to hold it in place. I sat and looked at myself on the mirror. I was beginning to not recognise myself. "Wow" I said. I was starting to feel like a pretty girl.

"You're not done yet, here comes the best part. The makeup." Kim said.

Finally I was sat on a high stool and various brushes and pencils were being used on my face. I had my eyes closed for all of it whilst the girls did what they needed to. "Open your eyes please Jaymie." I heard. I opened my eyes and I was left speechless.

I had defined lips with light pink lipstick, long eyelashes and just all round beautiful makeup. "I look hot as fuck holy shit guys, thank you so much!!"

I let the girls take the photos they needed so they could show off their work on social media and in their portfolios, before then going to get my clothes back on. "What are you doing Jaymie?" Kim asked. "They aren't the clothes you're going to wear, you're now wearing these" as I was handed a bag of clothes to put on in the changing room.

I put the clothes on before spinning to look at myself in the mirror. I was now wearing an orange blouse, with a short black pencil skirt and some tights, finished off with some wedge heels to help me learn to walk like a lady. I could feel the blood rushing to my penis. Was I now discovering a fetish for crossdressing that I didn't know I had? Or was I just an admirer of women's clothes?

"Come on Jay.....Mie" Kim shouted and out I came walking, struggling to get used to walking in the heels. "You'll get used to it, now come on we've got to get you up to the hotel and into your dress." We jumped in the car and off we went up to the hotel together.

During the drive Kim drew my attention to the glove compartment on her car. "Go on, open it" I followed her instructions and pulled out a tiara. "A present from me to you, everybody deserves to feel like a princess on their wedding day"

"But I'm not actually getting married Kim, I'm doing a favour for a grieving friend, that's it" I bounced back.

"Yeah sure you are, but you're going to be his princess tonight" she said whilst winking at me. We then pulled up at the hotel and I dragged the big box out of the boot.

"I'll take that bag for you madam." One of the porters said to me as he stared into my eyes. Did he know I was secretly a man? or had I fooled him?

"That's very kind of you young man thank you very much" I found myself flirting back. We checked in at the reception. The receptionist shouted "Room 701 please Damien."

"Right this way ladies" the porter said as we followed him into the lift and went up to the 7th floor. "Here you are, Room 701, the Ivory Suite."

As Damien opened the door the first thing I realised was the huge ceiling to floor windows which allowed you to see out across the city. "This suite is my favourite as you have a fantastic view. It also has a spa bathroom, a living area set with 65" TV, and a master bedroom through that door with a King size bed. A very romantic setting I might add. Now do not hesitate to call room service and ask for Damien should you need anything during your stay" he said whilst turning to leave.

"If I find I need a strong young man to help me with anything I know exactly who I will turn to" I gave him a wink. Damien blushed as he stood in the doorway. "I'll get the door for you" I said. "Bye for now Damien" he was covering his crotch with his hand. Was I really having this effect on guys?

" Well well well, look who it is, Jaymie the flirt. Don't act like you weren't loving that there." Kim said to me with a big grin on.

"Oh shut up, I'm just keeping up the disguise" I hit back.

"Here stop lying, and go to the bathroom over there and get your bridal lingerie on" she said as she threw the underwear to me.

I stripped off quickly and was soon naked. I fastened the garter around my lower stomach and made sure the suspenders were hanging down. I sat on the toilet seat and bent down to pull the first white stocking over my foot and up my leg. Fuck it felt good. The silk feeling sliding up my leg immediately had me hard as a rock. I'm glad the skirt of the dress was big and bushed out all the way around, at least it would hide my solid erection if this is how horny the outfit is going to make me, was what I was thinking to myself.

I managed to refrain from touching myself as I pulled the other stocking up and fastened up the suspender straps. I pulled the white silk knickers on and managed to tuck my cock in a bit so it was slightly disguised. Only slightly though! I left the bathroom so Kim could help pull the dress and fasten me up at the back.

"Wow you look like you really are enjoying this Jay" she giggled when she saw me.

"Don't be so disgusting, you're my sister!" I hit back with. but deep down, I knew she was right. And I knew my new fetish for crossdressing was becoming known about.

We lifted the dress up over my head and pulled it down so the middle corset area of the dress fit very nicely around my chest. Kim did up the lace at the back of it for me so it was tight in place before I put my tiara on. I sat down and put my feet into the stilettos, all whilst admiring the dress flowing down myself. I stood up and gave myself a quick twirl so that the skirt floated into the air. This felt amazing, and I could feel my smile beaming across my face. "Here you've smudged your lipstick a little so it's a good thing I brought it with me. Kim said as she pulled the little jar of lipstick out of her pocket. "This is how you top it up for yourself, ready for Stevie coming in and seeing you."

Next Kim did a mini photoshoot using my phone so that I had pictures of myself in this moment to always remember. Most likely nobody would ever see these pictures, but I would always have them. Finally my sister was now leaving me, but before she did, she pulled me into an embrace. "I've never seen you this happy Jay, I'm so happy for

you and hope you have a fantastic night. Whatever that entails!"

"Love you Kim, thank you for everything today." I told her as she left out of the suite door leaving me waiting for Stevie.

I picked my phone back up and fired a message across to Stevie. "Jaymie is ready for you in room 701, the door is on the latch so just come in. Hope you've got your suit on." I hit send and took the champagne out of the mini bar fridge and poured two glasses for us. My phone buzzed. "Be there in 5 minutes" it read. I necked my glass of champagne to try and give myself some courage. I was beginning to get really nervous. What if Stevie thought I was a freak? What if he goes and tells people about this? What if this is to be the end of our friendship?

I snapped out of my worry and poured myself another glass of bubbly. I took it with me to the bathroom whilst I had a final check of my makeup. I was topping up my lipstick when I heard the door shut. "Jay?" I heard Stevie shout. I didn't move. After shouting again he switched it up and shouted "Jaymie are you here?" I left the bathroom and walked around the corner to the entrance to the suite.

"Hi Stevie, don't you scrub up well in your suit." I told him. He was stood there in his dark blue 3-piece suit. Meanwhile Stevie was stood there staring at me, mouth gaping. I handed his glass of champagne over to him.

"U....h...." he stuttered. "You look amazing Jay" Stevie managed to say as I was walking away from him.

"Jaymie" I said whilst shooting a look over my shoulder.

"Sorry. Jaymie." he replied, then also downing his glass of chanpagne.

"Come on, let's have a dance" I said as I reached the open space living area. I hit play on my phone and put it on the side. Thinking out loud by Ed Sheeran began to play. I knew this was meant to be their first dance song. I had to grab Stevie's hand and drag him over as he was stood rooted to the spot just staring at me. It was like my makeover had put him in a trance, which did turn me on more than I already was. I had to take the lead so I grabbed his hands and put them on my waist before putting mine around his neck. I then started swaying to the music.

We were staring into each other's eyes as we danced. It was like he had so much to say but couldn't say it. "You smell amazing" I said to Stevie, having took the lead on this also.

"You.....Your...... hair is beautiful" he managed to stutter out.

"Thank you" I whispered back.

I felt his hands roam a little lower and become more firm. He was definitely lost in the moment which was good for him. As the song finished we didn't move. I looked up into his eyes. I don't know where it came from but I pulled his head towards mine and planted a kiss on Stevie's lips. He pulled away saying "We can't." I put my finger on his lips and said "Shh just go with it, if it feels right." And I went back in for another kiss to which Stevie seemed a lot more into.

By now I was rock hard, and I could feel Stevie's cock starting to press against me as we were close passionately kissing each other. Stevie was the first to introduce his tongue into it but it was welcomed by mine. I could taste whiskey on his breath, so I knew for definite he had had some drinks as some dutch courage before seeing me in his wife's wedding dress. It felt like time had stopped still. I didn't know how long we had been kissing for but it felt like ages.

My hands started to roam. It was like I wasn't in control of them. My head was telling me no, and to stop, but my hands kept moving down his chest. Did they stop here? No. they continued and started to trace the outline of Stevie's erection. I had never felt another man's penis before. Never mind a one that was throbbing because of me! He let out a slight moan into my mouth which seemed to egg me on. So I began to fumble around with his belt trying to undo it, before pulling his zipper down, and pulling his pants to the floor. My hand went into his boxer shirts and could feel his penis in all of it's glory now. I started giving it some gentle strokes to which I could tell that Stevie liked as his kissing became much more forceful with more moans into my mouth.

The next thing I knew, we were no longer kissing and I was on my knees pulling his underwear off. Still with a hand around his cock, I was looking straight at it. It was a decent size, 5-6 inches I would say. My head moved forward and I wrapped my lips around the head of Stevie's cock, I'd never given a blowjob before obviously, so I was leading blind. Pretty much going off what I felt when I was getting blowjobs and trying to give that feeling now. I slowly began to bob my head back and forward around the head of Stevie's penis. His grunting had become much more excessive now. His hands had moved to the back of my head and were pushing my mouth farther down his cock. The force stopped when I was around half way down as I picked up the pace of my sucking.

It didn't taste or feel at all as bad as I thought it would at this point. I thought I was going to be repulsed, but instead I felt exhilarated and was enjoying what I was making Stevie feel.

The force was applied to the back of my head again as Stevie clearly wanted all of his penis deep in my mouth. I didn't refrain, and gave him exactly what he wanted. I was deepthroating him. The tip of his head was at the back of my throat and I was concentrating on trying not to gag as my mouth was slurping around his hard cock. The moaning coming from Stevie's mouth was becoming more and more as I heard him try to speak the words "I'm..... going...... to cum." In my head, I thought this would stop me, but it didn't. I dug my acrylic nails into his arse cheeks and had him as far into my mouth as he could go. His penis exploded into my mouth. Ropes and ropes of his cum were firing down my throat whilst Stevie gave out the biggest grunt I've ever heard. I found myself thinking that his sperm didn't taste too bad either, it was just a bit salty.

With the pair of us both panting, trying to catch our breath, I got back up off of my knees. This was the awkward part. What do I say? Is there where it all ends?

Whilst a million thoughts were heading through my head, Stevie grabbed my hand and made a beeline for the bedroom. I no longer felt in control, and I loved it. He flung the door open, turned me around so my back was to the bed, gave me a big kiss before uttering his next words. "Bend over."

I did as he asked. I knelt up onto the bed and was position on my hands and knees with my arse pointing towards him. The skirt of my wedding dress was lifted up my back so that my stockings and underwear were on show. It was like he was controlled by lust with the way in which my knickers were dragged down my legs to my ankles. I felt the tip of his head at my anus.

I had well and truly slobbered all over his cock so I could only hope that this had it lubed enough so that it could go into my arse easy, with as least pain as possible. I felt Stevie's warm firm hands on my hips as he started to ease forward into my arse. My cheeks were clenched as his throbbing cock entered further into me. "Ahhh....Oww...Ahhh" were the only noises I could make as he moved in and out of my arsehole for the first time. "Don't stop." This gave Stevie the green light that I think he was looking far as he pulled my hips back down, fully submerging his cock in my hole. "Mmm ohhhh" was the high pitched moan that left my mouth.

This was the most vulnerable position that I had ever been in. I was being anally fucked. I had no control, and I was in heaven. My penis was as hard as a rock, whilst Stevie's was sliding in and out of me. He was getting more and more aggressive with it causing me to moan louder and louder. "Ahhh Fuck me, Fuck your princess" were words that left my mouth. It felt like it wasn't me that was saying them as I don't know where they came from.

Stevie was now pounding me harder and harder causing me to be closer and closer to my climax. "Uhhhhhh I'm going to cum" I screamed. With one final slam of his cock, I had the most euphoric orgasm. "AHHHHH" Streams of my semen flew out of my penis, landing on both the inside of my dress and onto the bed underneath me. As my orgasm hit, my anus clamped down onto Stevie's cock. With this squeeze of his penis, Stevie finished for the second time inside of me. This time he had dumped his load in my arse with a hugh grunt. He slid out of my arse with a "fuck."

I collapsed onto the bed panting for breath. I managed to drag myself up the bed and plant my head onto the pillow. I almost immediately was drifting off into a deep sleep as I felt Stevie slide up behind me and put his arm around me, pulling me close into a tight spoon.

Very quickly we were both asleep. With me tucked into him like his new lover.