Away from Home Fun

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A crossdresser gets more than they bargain for in a hotel.
1.7k words
4.48
17.7k
18
3

Part 1 of the 3 part series

Updated 07/26/2023
Created 01/28/2023
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I love working away from home. It gives me a chance to crossdress all girly in a way that I hardly ever get to do normally at home. Each time I try and step it up, and this time it's by locking myself in chastity and leaving the key at home, hundreds of miles away. Even just pulling off the drive was a turn on knowing that my clit couldn't get hard if I wanted to for a few days. Just leaving knowing I'd be all locked up for three days turned me on so much that as soon as I got around the corner, I slipped into my shiny girly bomber jacket. I knew I didn't really look like I was wearing female clothes, but I knew, and that was enough.

I eventually got to the hotel with plenty of time to unpack before going down to the bar for some food. I actually quite like unpacking in a hotel, or at least I do for my girly clothes. I just love laying them on the bed as outfits, knowing I get to wear them all. I'd even arranged them into sections of clothes I can get away with in male mode, sissy clothes and of course lingerie. Obviously, I had my satin nightwear too but that was already tucked under the pillow and my toys were ready too.

Once I was settled, I decided to listen to some hypno porn as I never normally got a chance to concentrate on it properly. Although I had no idea want would come to pass this evening, I thought it would at least make my solo session later more interesting. I always found that hypnotic erotica really brought the girly submissive out in me, especially when in chastity. Just lying there for an hour being told what a good girl I am and how I want a real man in my life did wonders.

Once my locked-up cock had leaked enough I decided to get dressed for some food, starting with my black PVC panties, matching bra, suspender belt and fishnet stockings. Over the top went my shiny cargo trousers and the bomber jacket. Although none of my outer clothing was massively girly, I knew it was and it really wouldn't take much to tell as you could clearly see my fishnets on my ankles. All of this made me strain against my cage even more.

It was fairly busy but thankfully I still managed to get a quiet table to myself, even as the bar got busier. After a while a man politely asked if he could share the table and I agreed, mostly so I could just carry on reading and we ignored each other for quite a while.

"Can I get you a pint?" He asked out of the blue and of course I accepted, by this time I was happy for a little bit of company. He had a big belly and was bolding as he was a fair bit older than me but he seemed like a friendly bloke.

"Here you go mate, I'm Gary" he said as he sat down and we shook hands, his being quite firm.

"I'm Ant, nice to meet you. Down here for work?"

"Yeah, for the week, what about you?"

"Same but only a few nights for me this time."

After this we got talking about the usual things, work, sports and tv programmes and bought we other a few drinks. On his next round though, Gary sat next to me rather than across the table although I didn't mind at all as we were getting on ok.

"I did notice something, which in fact is the main reason I came over" Gary said after a while.

"What's that then?" I asked, not entirely sure what he meant.

"It was your lovely fishnets" he said which both terrified me and instantly set my chastity device quivering. Although I was dressed like I wanted to get attention, now I actually had it I was terrified. I could barely think, should I just get up and leave?

"Oh... err... thanks" I shakily replied.

Before I had time to make a decision on what I was going to do next he put his big hand on my knee. As he rubbed my shiny, girly trousers I became weak and my heart started pounding in my chest. Even though I'd often dreamt something like this might happen, I wasn't used to having this kind of attention.

"I've always had a thing for people who dress like you do," he told me as his hand moved towards my inner thigh, squeezing just tight enough for me to notice. "and I was wondering if you wanted to come up to my room where we could get to know each other a little more privately."

My mind was an absolute blur, I really didn't know that to think, let alone say.

"I'd love to hun" I amazingly found myself saying, I never call anyone 'hun', but I just couldn't resist. The feeling of being wanted and desired made it too much for me to fight and I found myself slipping into my girly submissive self.

As we walked towards the lift, he put his hand on my lower back I almost melted completely and that was before his hand drifted downwards in the lift. He didn't just have his hand on my ass cheek, but he was actually rubbing up and down the crack.

Once we were in his room, I was an absolute bag of nerves. I found myself just staring at his room, still not knowing what to do. Before I could think too much, I could feel his towering form behind me. I'd never noticed how tall he was in the bar, but it was quite the difference.

He put his hands on my hips and slowly turned me around, so I was looking up at him. As he leant down to me, I completely melted, I knew there was nowhere else in the world I was meant to be. With one hand on my hip and one lifting my chin up his lips touched mine and I knew there was no going back and I really did love kissing big fat men.

As he pulled me even closer, I couldn't help but start to rub his big belly and I found I could only just reach round to feel his big ass. As I started to breath heavier my lips parted, and I knew I was his, I could taste his beer but that only made me want him more. I was so caught up in kissing this big strong man that I didn't notice his manly hands moving up my thigh.

"Now what do we have here?" he said with a grin on his face as he reached my crotch. I had almost forgotten about being locked in chastity until this point, my face must have been bright red. "Now why don't you undress a bit, and we can see what we've got?".

I had gone way beyond nervous to pure, unadulterated arousal so as Gary undressed and sat on the edge of the bed I slowly took off by bomber jacket and trousers leaving me just in my underwear. I pulled my panties to the side just enough to allow him to see my small pink chastity device that I was straining in.

"There's something else you should know," I said gingerly. "I've never... err... gone all the way with a real man before and I'm not sure I'm able to yet."

"Not to worry baby girl, we don't have to do everything on the first night.

"You can just come over here, get on your knees and suck me."

I could barely walk with nerves, every step felt like it was sapping all my energy but there was no way I could resist, he was drawing me to him. I knelt down in front of him and even though I was fairly upright, he was still just taller than me.

As he bent down to kiss me once more, I knew that this was where I needed to be and I started to kiss my way down his gorgeous, big, hairy body. It was then that I saw his still flaccid cock for the first time, the first time I'd seen any other mans.

Tentatively, my hand slowly reached out to it and started to stroke, feeling the warmth as I began to rub it. As I could feel it growing in my fingers, I found my lips getting closer and closer and I couldn't resist but to kiss the tip. From the second my lips touched his cock I was in love with it and my tongue licked every part of it until it grew to its full 6 inches.

When his gorgeous cock was fully hard, I open my mouth and my mind raced as I parted my lips and started to suck it. Moving my head back and forth, it went deeper with each push until I felt his belly on my forehead and I cupped his big hairy balls in my hands.

With each groan I sucked harder and harder, feeling the cock pulse on my tongue as my own was straining in its cage. It didn't take long for Gary to grab my hair and push himself deeper down my throat so all I could do was kneel there, being used, smelling his sweaty scent.

I never wanted it to end but as he held my head tight against his body he came straight down my throat. I had tasted my own cum a few times, but this was so much better and so warm as it slipped down my throat. As he let go of my head, I made sure that I licked every part of his cock clean.

"Why aren't you a good little cock sucker" he told me as he got his breath back and he pulled me onto the bed so I could lie in his arms, feeling safe and satisfied.

"Tomorrow," he continued "I'll meet you at the same time and we can even more fun can't we baby?"

"Yes Sir"

"No off you go, and I'll see you tomorrow."

"Of course, Sir" I said as I started to get dressed "Thank you."

And with that I left the room, feeling like the people in the lift could smell his cum on me as I made my way back to the room.

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  • COMMENTS
3 Comments
trikertony97vtrikertony97vabout 1 year ago

Love it I can't tell if it's fact or fiction or a mix of both but well written

sr_gawainsr_gawainabout 1 year ago

Great one. Keep it going!

PinkPanties4mePinkPanties4meabout 1 year ago

Good start! Please continue!

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