Turning a Dream into Reality

Story Info
A recurring dream leads a man to live it out for real.
2.9k words
4.21
42.7k
13
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This story is based on a dream that I have had continually for the last few weeks. I don't know why I've been dreaming about this and maybe writing it will make it stop. Everything in this story actually happens in the dream.

************************************************

I had been planning this night for weeks, ever since I had first dreamt about it. The planning though had been easy, compared to actually arranging it. Numerous phone calls had to be made and it had cost me two thousand pounds just for the room and another thousand for each of the girls, but I knew that at the end of the night it would have been worth every penny.

I had two hours before I had to be at the hotel so I went and ran a bath for myself, stripped off, and climbed in. I lay back and washed myself all over before picking up my razor and, looking into my mirror, carefully began to shave my face. Once my face was finished I lay back and started to imagine what the night was going to be like, my cock starting to harden at the thoughts I was having, and I reached down and started to stroke myself slowly.

I had to control myself though, knowing what was in store in only a couple of hours, so I stopped and climbed out of the bath before I made myself cum. As I dried off I kept glancing at my body in the mirror. I wasn't that bad looking, had long dark hair, was fairly well toned and my cock was somewhere between seven and eight inches when fully hard. I finished drying quickly and then headed in to my bedroom.

I had already laid the clothes I was going to be wearing for the night out on the bed, and I stood and looked at them. There was a black two piece suit, red shirt, new socks, new boxer shorts and a brand new pair of shoes. Slowly I got myself dressed looked in the mirror to check that I looked smart enough and then sat in front of the mirror while I tied my hair back in a ponytail, which I had to do because once it had been washed it was that fine it blew about wildly.

Finally I was ready and, after making sure everywhere was tidy, I walked outside and locked up. There was still forty-five minutes until I had to be at the hotel and, as it was only fifteen minutes away, I stopped at a bar along the way and had a couple of double Brandy's. I drained the second glass and continued on my way to the hotel, finally arriving a few minutes early. I walked over to the reception, gave my name, asked if everything was ready, took the key and then caught the lift up to the top floor and the penthouse suite.

Once the lift stopped I stepped out and, using the key, opened the door directly in front of me and walked through it. The four of them were already there, just like reception said, and in just their lingerie as instructed when they had been hired. I greeted them all and walked straight through to the bedroom, checking everything was exactly how I had specified it should be, before going back to the room where the girls were.

Over by the window, in an ice bucket, were two bottles of champagne and five glasses and I walked over to where they were. I took the glasses out and lined them up before taking one of the bottles, opening it and filling each glass and calling the girls over to me.

I watched them closely as they made their way across the room, each one looking absolutely perfect, and handed them a glass when they reached me.

"I am so glad the four of you could make it." I said as each one took their glass. "As you are all aware my name is Kyle but unfortunately I don't know any of yours."

One by one each girl gave me their name and, once I knew them all, we went and sat back down with our drinks. We talked as we drank, with me explaining exactly how I wanted things to happen, and soon Steph, Claire, Natalie, Amy and I were laughing and joking like old friends who had known each other for years, instead of minutes. Eventually the first bottle was completely empty and I was about to open the second when I was stopped by Natalie.

"Why don't we save that until afterwards?" She said, and came and sat down next to me.

"Good idea Natalie." Claire said, sitting the side.

Steph and Amy also came over and sat on the floor at my feet and then the girls started to undress me slowly. Natalie undid my shirt and slipped it off, Claire unfastened my belt and trousers and, once Steph and Amy had removed my shoes and socks, helped them take my trousers and boxers down. In less than five minutes I was sitting there naked, my erect cock pointing straight up, and Claire took my hand and pulled me up from the sofa.

"I think it's about time girls." She said. "Are you sure you really want this Kyle?"

"More than I have ever wanted anything else." I answered.

"In that case come on then." Claire continued and led me to the bedroom, the other three girls following behind us.

Once inside I climbed onto the king sized bed and, as arranged when I set everything up, there was a girl at each side of the bed, one at the head and the last one at the foot and I laid back. I took my cock in my hand and began to slowly wank myself and, as if that was a signal, the girls stripped off their lingerie and, for the first time since entering the penthouse, I saw their cocks.

I moved my head to look at each of them and noticed that, although they were all pretty much the same length, Steph's was definitely the thickest and noticing the way they had arranged themselves around the bed it was going to be hers that I took last. Natalie climbed onto to the bed and, making sure my head was just over the end of the bed, she lifted my legs and placed them onto her shoulders, while the Steph and Claire climbed onto the bed also and Amy moved as close to the head of the bed as she could.

I let my cock go and reached both arms out, until I had Steph and Claire's cocks in my hands. Amy gripped her cock and, as I opened my mouth, she guided herself past my lips. Once I was comfortable with how I was Natalie covered her cock, and my tight ass, with lubrication and started to push against my ass. After a trying to penetrate me a couple of times she gripped her thick shaft and guided it against me once more, finally the shiny purple end penetrated me, and I gasped as loud as I could with Amy's cock in my mouth.

As Natalie started to pump her cock slowly in my ass, I began to suck on Amy's cock and wank Steph and Claire at the same time. I felt in absolute heaven as my ass and mouth were being filled with juice fat transsexual cock, while I had two more gorgeous cocks in my hands and it wasn't long before Natalie's thrusting became faster and more urgent. She began to pant rapidly and I felt her cock twitch before she started to cum inside my ass.

Natalie continued to fuck me until she was completely drained of cum and, as soon as she had finished, she pulled her cock out and the girls moved in a clockwise direction around the bed with Claire's cock replacing Natalie's in my ass.

Claire slid in my ass easily, using Natalie's cum as lube, and she started to fuck me harder and faster than Natalie had. Steph's large cock was going as far into my mouth as I could get it and I wondered what it would be like to swallow her cum, if she didn't last until Claire had finished but she did, and I didn't get to find out, not yet anyway.

Claire whipped her cock out only for it to be replaced by Amy's and soon my ass was being hammered again, I was in total ecstasy and couldn't believe all the planning I had done had actually come off. As she fucked me Amy reached forward and began to wank my cock slowly, which was a relief as I thought I was about to explode, and carried on slowly doing so until she to finally shot her thick white cum deep into my ass.

Once her cock had been slowly removed I braced myself for Steph's thick hard cock. Instead of lifting my legs onto her shoulders though, Steph turned me onto my stomach and lifted my ass into the air. I could still wank Amy and Natalie's cocks, although it was a little harder and Claire's cock actually entered my mouth a lot easier.

As soon as I was ready I felt Steph's thick lubed cock head pushing hard against my loose ass and felt it slide in easily. Although it was thicker than the others it didn't hurt as much as it would have if it had been the first to enter me, and she gripped my ass tightly before beginning to pound into me harder and faster than even Natalie did, yet she lasted longer than the other three, eventually cumming after about fifteen minutes.

Once she had finished I rolled onto my back and stared at all the girls and their gorgeous cocks, in varying degrees of hardness. Looking at them I wished that I had sucked them all dry and tasted every single one of them, instead of them filling my ass, even though the feel of all their cum inside me, and that which was leaking out, felt so good.

While I lay there, my cock still rock hard and yet to cum, the four girls moved away from the bed and began to talk among themselves. As they talked I reached down to my cock and slowly began to stroke myself, the need to cum was driving me crazy, when they turned back to the bed and saw me.

"Kyle we know it's not part of the deal and we have already been paid for the whole night." Claire said. "But the four of us wondered whether you would like to fuck each of us before shooting your cum all over our asses."

"I would love to but how can I be sure that I won't cum in one of you letting the others miss out." I answered.

"That's easy to solve." Amy said. "You fuck each of our asses for no more than a couple of minutes and if you feel yourself about to cum just stop."

"Yeah and once you have fucked every one of us you will then wank your cock until you cum on us." Steph added.

Quick as a flash I agreed with their idea and, once they were all lined up on the bed, positioned myself behind Steph. I decided to fuck Steph first as she was the last one to get to fuck me and thought that was the only fair way to so it. I slowly pushed my cock against her ass and it slid in easily. Slowly I began to build up a gentle thrusting rhythm, while Steph played with her own cock, and as soon as I had fucked her for the two minutes, removed my cock and moved across to Amy.

Ten minutes later, and once I had fucked each girl's ass, I was kneeling behind them wanking furiously. It didn't take long and as soon as I felt my balls tightening I got behind Amy and squirted a thick stream of white milky cum over her ass, then gripped my cock tightly so I didn't cum anymore, and moved across. Eventually I had covered each of them with one thick stream of cum but I was still cumming, and I managed to shoot another stream over each of the perfectly round asses in front of me then finally collapsed on the bed.

"That was fucking great thanks." I gasped to the girls.

"Why don't we have that other bottle of champagne now?" Claire said and jumped off the bed.

While she was gone fetching the bottle the other three girls sat stroking their own cocks, getting them fully hard again. By the time Claire returned with just the bottle their cocks were all standing fully erect and glistening in the light.

"I didn't bother with the glasses we can just pass the bottle around between us." She said handing me the bottle. "If you would do the honours Kyle please."

I quickly had the bottle open and passed it back to Claire, who took a large gulp, then gave it Steph. As the bottle went round I couldn't take my eyes off their cocks, something which Natalie noticed, and before I knew it the girls had put the bottle on the floor and were all sat around me.

"I've noticed that you can't stop staring at our cocks." Natalie said.

"I'm sorry they are just so beautiful." I said.

"Well why don't you get a closer look then and suck us all off." Amy said.

I didn't need telling twice and, as Amy was the last to speak, I bent my head and took her cock deep into my mouth. Although I had always loved the taste of my own cum, and sucked more than a few cocks, I had never actually tasted anyone else's but within five minutes that all changed as Amy's cock twitched violently and a thick stream of cum hit the back of my throat.

She gripped my head and continued to fuck my face until she was fully spent and removed her cock. I quickly grabbed Steph's, as she was closest, and began to suck vigorously on that until she too came in my mouth. Natalie and Claire had also soon cum in my mouth and as I lifted my head the four of them all looked at me.

"You suck cock really well Kyle." Amy said.

"How often do you do it?" Claire asked.

"I have sucked but never swallowed before." I answered.

"Well you should definitely do it a lot more." Steph said.

"We all know a lot of girls like us that would love to meet someone who sucks cock as well as you do." Natalie added.

We continued to talk until the bottle was empty and then I came up with something else I would love to do.

"Instead of starting with the fucking again I was just wondering." I started.

"Wondering what Kyle?" Amy asked.

"Well I saw something the other day I would really like to try."

"Tell us then come on don't be shy." Steph said.

"Okay I would love to lie down while the four of you wanked, and came, all over me." I said.

"You mean bukkake?" Amy said. "That sounds like it could be fun."

"Come on then Kyle lie down and we will." Natalie said.

As soon as I was flat on my back the four of them got into position and began to stroke their hard cocks furiously.

"Why don't you wank as well Kyle?" Steph said. "Five loads of cum will look better than four."

The other three girls all agreed and, after they started to chant my name, I took hold of my cock as well. The five of us wanked as fast as we could and I soon felt the first stream of cum land on my chest, from Natalie, quickly followed by Amy and Steph. My chest was covered as I finally shot a thick stream, with such force, that it landed on my neck and chin. Claire continued to wank until, she to, finally couldn't hold back any longer and covered my face with her thick milky liquid.

I must have looked a right mess lying there, five loads of cum covering my body, but the girls soon had me cleaned up with towels from the suite's bathroom. Once I was all clean I phoned down to room service and asked them to bring two more bottles of champagne up to the room, which they duly did.

During the rest of the night each of the girls fucked me twice more, and I sucked their cocks again, until we all eventually passed out from the champagne and sex. The next thing we all knew it was just after lunchtime the next day and the maid was banging on the door shouting about needing to clean the room.

We hurriedly got dressed and, before we parted ways, I asked them all if they would like to make this a once a month meeting and was so pleased when they all agreed.

"Maybe we will bring a couple more girls with us next time." Amy said winking at me as she walked out of the door.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
wants2tryit1xwants2tryit1xover 10 years ago
Fucking nasty hot

Your story made me wish I was Kyle :)

FRSWRITERFRSWRITERover 13 years ago
outstanding

very very hot as usual hope to see more of this one also

AnonymousAnonymousover 13 years ago
And in my "dream"

I dream that I have aids and there is a cure for it!

nomoretears00nomoretears00over 13 years ago
Wow

Now *that* is a dream!

Share this Story

Similar Stories

My Ex Girlfriends Mom Randomly seeing an ex girlfriends mom can be a good thing!in Transgender & Crossdressers
Your Best Damn Girlfriend Ever College shemale encounter.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Finding My Dream Wo(man) Never knew I wanted a tranny till I found one.in Transgender & Crossdressers
Her Bulge The woman at the gym has a bulge in her spandex.in Transgender & Crossdressers
More Stories