Wedding Dress Enlightenment Pt. 03

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The aftermath…
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I woke up in the morning to find that I was all alone in the king size bed. Stevie's clothes were no longer sprawled across the floor. Whilst I was dead to the world he must've snook out of the room. Anxiety started to set in. Did he now hate me? Was he regretting fucking me whilst I was wearing the wedding dress his partner was meant to wear? My head was scrambled. And I understood that Stevie's probably was too.

I started replaying the events of the previous night in my head. I started remembering how great it felt having a cock in my mouth and seeing the pleasure on Stevie's face. Subconsciously I started stroking myself through the skirt of the wedding dress that I was still wearing. I felt a twinge in the muscles in my bum which directed my mind to the feeling that my arsehole had been stretched. I found myself stroking faster. I loved that feeling. The feeling that my hole had been used for somebody else's pleasure and they had dumped their load inside of me. I was wishing that Stevie was still here this morning so that I could be used again by him. The speed of my stroking increased again. With a "ohh fuck me" out of my mouth I blasted another load of semen all over the inside of the dress.

Soon after my phone started ringing. I found myself hoping that it was Stevie but it instead turned out to be Kim. "Morning Jaymie." She said when I answered"

"Hi Kim" I responded.

"Sooooo... how was your night then?" l

I stayed silent.

"Ahh you had sex didn't you?!" She asked excitedly.

"NO!" I snapped back at her.

"I think you're forgetting that you're acting as a female now. And we tell each other everything."

After a brief pause I responded. "Pick me up, bring me some clean clothes please and you've got yourself a deal."

"I'll be there as soon as I can." And that was the end of the call.

I finally pulled myself up out of the bed. I took one last look at myself in the mirror. I looked like a hot mess if I said so myself. My makeup was smudged, an eyelash was hanging off, parts of my hair had came out of the pin up and my dress was creased in various places due to the way in which I had slept. the reflection in the mirror did make me giggle a little. I pulled out my phone and snapped a picture so that I had a before and after picture. I then fought with myself and managed to undo the dress at the back, allowing me to shake it down to the ground and step out of it.

The first thing that struck me first of all was how amazing the lingerie looked on me again. Then secondly, the fact that my penis was just out and free. Where were my silky knickers? They must've fallen off from around my ankles as we collapsed to fall asleep. I searched around everywhere for them and could not find them. I came to the conclusion that Stevie must've taken them with him as a little souvenir when he left this morning.

There was a knock at the door which I knew would my Kim. I grabbed a towel to wrap around myself so that she didn't see my dick and opened the door. She came walking in, took one look at me and burst out into a fit of laughter. "hahahaha you cannot try and lie to me and say you did not get fucked last night! Look at the state of you" she managed to say through her laughter.

"Okay you're absolutely right. But sis, it was amazing." I responded.

"Here's some clothes, get yourself in the shower and you can tell me all about it on the way home." She threw me a bag of clothes before removing all of the clips and pins from my hair.

I returned from the bathroom wearing a shortsleeve floral dress. This was the first time I had my legs exposed free to the world. I wasn't sure what everybody was going to make of it but I didn't have a choice. This was what I had been provided with. The dress was packed up into the box and left the suite and headed back down to the reception area.

I approached the desk to pay up what was remaining on the room bill. I told them the room number and expected a moderately sized bill to be produced. The receptionist picked up a note he had been left. "Ah yes Ms. Jaymie. Your companion paid the bill before he left."

"What? Really?" I questioned.

"Yes Miss, he told us that you were not to worry about it," I smiled and turned to leave. "Have a nice day Ms Jaymie" he politely said to me as I walked to meet Kim outside the front entrance.

"Can you believe this? Stevie paid the bill on his way out?" I told her.

"You must've gave him a very good time if he's done that for you!" I pretended I didn't hear her as we walked over and got into her car.

We had barely left the car park when Kim slapped me on the knee and said "Come on then, spill. What happened in that hotel suite?" I told her everything like I never thought I would. From how we danced, to Stevie's erection, to kissing, to sucking him off, to getting fucked doggy style by him to finally him being nowhere to be seen this morning. "He's probably in the same position as you. He's never done anything like that and needs to get his head straight." Kim said.

She was most likely right. However on my side of things my head was very clear. Jamie is a straight man. Jaymie however, is a bisexual male to female crossdresser. Still attracted to women, but also attracted to men and the power she has over them whilst dressed in sexy dresses.

Kim dropped me off at my house. "Just have a nice chilled day, and see what comes from it. Don't push him too much otherwise you may lose the friendship completely." She said before driving away. I was exhausted from everything over the last few days so I decided that I would go back to sleep for a little while. When I got into my bedroom I slipped the dress off of my shoulders and let it drop to the floor. I made a beeline for my late partner's drawers that were still full of her clothes. I pulled out a 2-piece silk pyjama set that was black in colour and started to put them on. The vest top was pulled over my head, and the shorts were pulled up so that they fit around my plump cheeks. The silk felt great against my skin as always, as I went over to the mirror to check myself out. I snapped a few selfies in the mirror to add to my Jaymie collection, and made sure I got an over the shoulder one which showed off my arse. I did look and feel hot. With my change of clothing I jumped into bed to go back to sleep.

I woke up around 3 hours later... Damn I must've needed that catch up on sleep. I picked up my phone hoping to have something there from Stevie. Nothing. I knew I was going to have to make the first move, to see where last night's events were now going to lead us. I opened up Whatsapp and began typing my message.

"Thank you for last night. I really enjoyed it and hope you did too. Here's a picture of the dress in case you want it. Let me know if we need to talk." Before clocking send I had a bit of a lightbulb moment. Me and Stevie usually talk on Whatsapp normally, so perhaps I should use a different app for when I am Jaymie? I cut the message I had typed out and opened up iMessage. The message was copied back in before I attached the image that Kim snapped of me in the wedding dress. My heart was beating double time as I hit the send button.

I was now in an even more vulnerable position. Somebody else now had a picture of me crossdressing, and could release it at any moment. This anxiety was exhilarating and I was beginning to get worked up at the thought of it. My cock felt great against the silk pyjamas that I was wearing as I stroked myself through them. It didn't take me long to reach my climax and spray my load all over the silk.

Over the coming hours I received no response from Stevie. My phone eventually pinged, but all it was was a heart react emoji to my message. That was it. No response. I won't lie, I was a bit hurt by this as I was hoping that he would just say anything, but oh well.

To help myself feel better I decided that I would have some online retail therapy and order myself some new outfits. I purchased various new dresses, some short and skimpy going out dresses, and also some daytime outfits, consisting of long dresses and blouse and skirt combos. I found myself reading up on cross dressing forums about what the best way to hide certain aspects were, i.e my penis that would no doubt get hard at some point whilst wearing my new clothes. It seemed that the recommendation was to wear a cock and ball cage, which could if used correctly work like a clit and could be played with. So I made my way to a sex toy website and ordered one of these cages along with some butt plugs and anal toys so that I could play with myself in this new experimental way.

Fast forward a couple of days to the next Saturday, and I decided to go back down to the salon for what was only meant to be a touch up on my nails...

After the last couple of days, I was finally getting used to wearing the cage and being able to use the toilet whilst wearing it. As I walked into the salon everybody wanted to hear the story of how the night with the wedding dress went. I told them all everything, along with how I hadn't heard from Stevie since. Chloe came up with an idea. "Next Saturday (1 week from today) is my hen party and we are all going out for it. Why don't you come with us Jaymie? Everybody finds hen parties sexy so we can all wingwoman you to help find somebody who will appreciate you a bit better!"

"Thanks girls, count me in." I said with a big smile whilst my nails were being touched up. Chloe then went over a few more of the details for me. "So the theme for everyone is to wear a LBD as I will be wearing a white one, and I have organised some sash's for us to wear so that we stand out. We're all going to meet here in the morning to get our makeup and hair done before we have our afternoon and evening out." It all sounded good so I said my goodbyes and left with an excited spring in my step.

When I arrived home I decided that I would treat myself to a takeaway and film night on my own. I washed and conditioned my hair so that it was nice and soft, I then sat down at the makeup table and applied some to my face. I wore one of my new blouses with a short leather skirt. Accompanied by my favourite accessory, stockings. The tops were covered by the skirt which was how I liked them, left to the imagination.

I could see across different pieces of social media that Stevie was out drinking with some friends. Hmmm, okay, whatever I thought to myself. The takeaway I ordered arrived and I saw the young delivery driver look me up and down whilst he handed me the food. Good to know that a week later I still had it and could make a man feel a certain kind of way.

It was getting late and I must have dozed off during my film as I jumped up awake. My phone pinged which is what woke me up. I opened up the message.

"You up? X" It read. It was Stevie. Was I being bootycalled!? Was what went through my head. However it didn't affect me negatively. I was excited to hear from him finally. I sent a message back.

"Well I was just about to get into bed. Why? X"

"Wait for me I'm on my way xx" was the message I got back. This started to make me flustered. I ran up the stairs to check myself out in the mirror to make sure I still looked okay, I touched my makeup up and added another layer of lipstick to my lips.

I didn't live far away from the pubs and clubs so I knew it wouldn't take him long to get to my house. As I put my makeup back down, there was a knock at the door. I pulled myself together and went to open the door. m

"Hi Stevie." I said softly. My nostrils were immediately hit by the smell of alcohol radiating from him.

"Jaymie......." Stevie slurred as he entered the house. "You.... look..... stunni" Was all that came out of his mouth as before he could finish he had me pinned against the wall, with his mouth forced onto mine. His lips were still soft and wet but his breath was warm and tasted like lager. I returned his kiss. We were now making out with my back pinned against the wall. This went on for 5 or so minutes. I managed to push him away and speak to him.

"We need to talk"

"Talk later I need to have you now." Was the response I got. Stevie grabbed my hand and headed for the stairs. I was immediately even more horny. Stevie was fuelled by lust right now. Lust for me.

The door to my bedroom flung open. Stevie span round and picked me up like I was nothing and threw me onto the bed. He lifted his shirt up over his head and threw it onto the floor. Whilst lying on the bed I undid the buttons on my blouse leaving my black lace bra on show. I sat up. I ran my hands down Stevie's chest before undoing his belt and dropping his jeans to the floor. I grabbed his hard cock through hid boxers and looked up at his face. Our eyes met and I could see a burning desire in his. He pushed me back down to the bed with force and removed his underwear. The next thing I knew I was being straddled by his legs with his hard penis right in my face. He directed it into my mouth and started sliding in and out. I was in no control at all as my mouth was being fucked. I was making sure that his dick was lubed up very well as I knew where he was wanting to put it next.

Deeper his cock thrusted into my throat until I was gagging and pretty much choking on Stevie's penis. He pulled himself out and lifted off from straddling me. My skirt was forcibly removed and I was rolled over onto my stomach. His big hands on my hips lifted me onto my knees before the matching thong was moved to the side showing Stevie the goal that he was here for. His cock was squeezed through the muscles of my anus that were resisting him. "Mmm Ohhh.... Ohhhhh" were the noises coming from me as Stevie fully entered me.

"Slutty stockings again you slut" The sentence was ended with a hand slapping my arse hard.

"Owww ahhh" as my muscles contracted onto the cock that I was being fucked by. The fucking got harder and harder and faster. The grunting from Stevie was getting louder and more forceful so I knew he was close to dumping his load into me. I grabbed his hand off of my hip and was moving it around to the cage and my "clit"

"Play with my new clit" I said.

Stevie took one stroke of my "clit" before I felt a hand grab my hair and pull it back, causing my neck to lift up with him. Whilst still giving me the hardest of fuckings he shouted "I'M THE ONE IN CONTROL HERE YOU SLUTTTT!" And with that, ropes and ropes of cum was sprayed up to my prostate. Just like last week, we both collapsed onto the pillows panting and fell asleep.

I woke up in the morning to find that I was alone in the bed again, with all of Stevie's clothes having disappeared.

(Please let me know your thoughts up to this point of the series. I have my own thoughts/fantasy of where i'd like it to go but I am open to suggestions from the many of you who are enjoying the story. Please remember it is also only being wrote for a bit of fun.)

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AnonymousAnonymous2 months ago

That was a great story please keep writing.And see were Steve and his best frieng go from this story. Maybe they relationship together will get strong and Steve and his best women will really want to tie the not.and live as a married couple.

4Leather4Leather7 months ago

Mind blowing story. Steve is a pure dominate male that just wants to be in control get his rocks off now that he has found a slut in Jaymie's for his use. Love to see were this leads. Next chapter please.

AnonymousAnonymous8 months ago

Sounds like Steve has a problem he wants it at night but you don't want to be there in the next mor no he sounds like hes not very well-adjusted to life Maybe you can write another part of him coming and staying for the rest of his life being married to the person that he is married to and not just have an alcohol wanting to have sex how does the same way in a wedding night and the same way when he came later on he had to have liquor to give him courage he is a d*******

AarnCoralAarnCoral10 months ago

Great story so far. Hope you continue.

My expectations for Jaymie's future:

She goes out with the girls, seduces a guy, and they make love (not just sex like with Stieve)

She starts working at the saloon, and becomes 'one of the girls' - all the while dating the guy she met at the hen party

She starts HRT, and corset training. Gets a boobjob, and finally transitions fully to womanhood.

And the story could end with her again in the bridal dress - but this time for her own wedding.

AnonymousAnonymous10 months ago

Skeve is an A hole he wants his cake and eat it too he has no compassion for a good coupling he should be kicked in a groin and put out to pasture until he realizes what he has done wrong

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