Away from Home Fun Pt. 02

Story Info
Another night of fun in a hotel for a crossdresser.
2.4k words
4.58
7k
6
2

Part 2 of the 3 part series

Updated 07/26/2023
Created 01/28/2023
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

I still don't know how I even got back to my room; my mind was such a blur. How had I gone from occasionally crossdressing to sucking off a stranger in a hotel?

All I could do when I got back to my room was to take a shower to try and recover, desperately tugging at my chastity device in the hope of cumming but to no avail. I even tried listening to one of my sissy hypno that almost made me cum hands-free once but again, nothing.

The combination of my satin camisole set, extreme horniness and the taste of Gary's cum still on my tongue meant I had a very restless night.

Another tugging session in the shower in the morning didn't allow me any release, so I figured I'd just go to work, in my panties, as horny as hell. Although I did more than enough work to not get in trouble, I was so horny I just wanted to serve everyone I met, and my chastity device was straining the whole time.

I eventually finished for the day and rushed back to my room so that I could get ready to meet Gary again in the hope that I get to make him cum again. Although my routine was fairly similar to the day before, all of my senses were heightened because of my arousal.

My outerwear was the same as the day before for my trip to the bar, but I decided to go a little different for my underwear, this time much sissier. I first slipped on my pink stockings, loving the sight of them matching my pink chastity device. Next came the pink satin halter neck bra and finally my favourite panties in the whole world, they were high waist pink shiny satin briefs with a white PVC lining which always drove me crazy with excitement, something I hoped that Gary would share.

I got down to the bar extra early this evening as I just wanted to be with Gary again and please him. I felt even more inconspicuous than the previous night as the pink stockings were very visible on my ankles and if you looked closely, you could see the strap of my halter neck bra.

Sitting there, waiting for him I could feel myself leaking in my chastity cage until he finally entered, and my heart skipped a beat. He was dressed in jeans and a t-shirt, but I didn't see them, all I could see in my head was his lovely big, naked belly and juicy cock that I just wanted to suck again.

"Hi gorgeous," I found myself saying "I'm so pleased to see you again".

"Thanks" he replied as he sat down next to me, I'd almost forgotten how manly his voice was and how it made my head spin. "I can see you've got something different on for me tonight."

"Errr... yes" I replied blushing as I did, thinking who else might have noticed, even if that's what I actually wanted.

We chatted and ate like the night before but this time we sat much closer to each other, almost looking like a real couple to anyone looking on. My hand barely left his thigh the whole time, and it slowly inched towards his crotch as time went on, making it clear want I wanted.

Finally, he said the words I had been dying to hear since I had set eyes on him again.

"Fancy coming up to my room again?"

As we walked to the lift his hand was straight on my ass, showing the whole bar that I was his to own and use.

Thankfully we were alone in the lift so he could pin me to the wall. The feeling of his big belly against my back made me so horny that I curved my back so his bulging crotch was rubbing my ass.

"God, I want your cock so bad," I told him.

"Well, that's good babe, because you're getting every inch tonight," he said as he leant in and kissed my neck from behind. I felt so weak in that moment, I knew I couldn't resist him.

The second we entered his room our tongues were entwined. He walked me backwards onto the bed, kissing me the whole way until I was once more under his big body weight. Our hands explored each other's bodies and I found myself thrusting my crotch towards him before I realised that my cock was locked and it was no use. I wrapped my legs around him as much as I could and pulled his body close so I could feel his ever-bulging groin against me.

"Why don't you show me what you've got on under there night?" he asked.

As he sat on the edge of the bed I stripped off my clothes to show my sissy underwear which, judging by the smile on his face, he approved of. Once he had stripped most of his clothes too I could see that he was wearing some wetlook hotpants which I could only just see under his gorgeous belly, not being able to see his juicy cock just dove me even wilder.

I instantly sat on his lap and kissed him once more with my arms around his neck. I'd never kissed someone so passionately or felt as feminine as I had at that moment.

Gary obviously loved my underwear too as he couldn't keep his hands off my ass, tracing my crack in the panties. After a while, his hands slipped inside them, and he must have felt the PVC lining for the first time.

"Now who's got some naughty underwear on tonight?" he asked with a grin on his face.

"I hoped you'd like them".

"Why don't we see what they look like when you are on all fours on the bed?"

"Hmmmm" I replied as I got off him and crawled my way up the bed. I tried to move as seductively as I could, shaking my hips as I went. I could feel his gaze behind me, staring at my satin ass he moved up the bed behind me.

My breath got heavier as I felt him come up behind me, I curved my back to show off my behind more as his sexy belly rested on me and he caressed my ass. Suddenly, there was a massive smack on my ass that took my breath away as he spanked me.

"Too much hun?" he asked caringly.

"Only a little," I replied once I got my breath back "It was more the surprise".

"Good, because there's more where that came from," he said as his hand slapped my ass again. This time though it actually felt good and sent a pulse of electricity through my body.

This continued for a little while until my ass felt like it was glowing, and he started to peel my panties off me. I felt so vulnerable, on all fours with just a sissy bra and chastity device on and my naked ass presented to him.

I felt his manly hands grab my hips and pull me towards him as his crotch rested in my ass crack. It made me strain in my cage so much that I said something I never thought I would to another man.

"Please fuck me, I need your cock in my ass."

"Not tonight hun," he said to my great disappointment "Your pussy isn't quite ready, and I don't want to hurt you."

I felt the pain of disappointment and almost cried. I'd struggled to admit these feelings to myself, and it was a huge step to say it out loud, but I had been shot down.

"But" he added quickly "If we have a little fun tonight, and if you do a few things between now and tomorrow, I'm sure we can have a lot more fun on our last night together."

"Oh yes please!" I begged.

"Pleased to hear it, now pass me the lube from the bedside table" he instructed.

Once I had, I could feel his hands rubbing my ass crack once more before I could feel the cold sensation of the lube being squirted next to my ass pussy. His fingers slowly circled against the outside of my asshole, and I could feel my caged clitty leak. Ever so slowly and gently he slid his finger inside me, and I couldn't think of anything, I was just ecstatic to be on all fours, being fingers by a sexy hunk of a man.

As his finger got deeper and deeper, I felt his next finger slip in and I let an involuntary moan out, especially as his fingers were quite chunky. Once both fingers were all the way in he started to slide them back and forth and I just wanted to be fucked by him and it almost felt like I was.

Next, with his fingers still deep in my ass pussy, he reached over and got a metal butt plug which was only a little bigger than the girth of his fingers.

When he removed his fingers, I felt empty but almost immediately he was rubbing the cool metal of the plug against the hole. Slowly but steadily, he inserted the butt plug into my ass and I groaned as the widest part stretched me more than I had been stretched before. As the plug popped its way in, I almost came, the feeling of my hole closing around the metal felt divine.

Although he asked if it felt good, I couldn't even get my words out my mind was such a blur and I collapsed on the bed. Gary lay next to me and put his arms around me, making me feel secure with an ass full of the butt plug.

"I could really do with a shower," he eventually said as he gently stroked my chastity device "so why don't you join me and you can help me get clean".

"Oh, I'd love to hun" I replied, even though my answer was obviously only ever going to be yes.

With that, he took my hand and I followed him into the bathroom where he turned on the shower. As the room steamed up, we started kissing once more and he started stripping me off so all that was left to cover my vulnerable body was my chastity device. I love being in his strong arms, especially with my ass feeling full of the weight of the butt plug.

"Now it's your turn to get me undressed," he said as he gently pushed my shoulders down. I immediately knew what I needed to do and got on my knees.

I'd almost forgotten that he wasn't naked which might sound strange, but his belly sometimes made his cock hard to see, something that actually turned me on more.

Once on my knees, I could once again see the outline of his cock in his hotpants, and I couldn't help but to rub and kiss it through the material. I could see it growing as the tip got more pronounced and I slowly started to slip them down, revealing his gorgeous cock.

I couldn't help but start kissing his thick shaft savouring the taste of his cock on my lips.

"Come on babe, time to get me clean" he demanded as he led me into the shower.

The sight of the water dripping down his hairy man boobs and belly was almost too much for me to handle and we instantly started kissing once more. Our hands explored each other and I could feel my ass tighten around the plug.

He passed me his shower gel and I was so happy, any excuse to rub his whole body. It felt so sensual to be put to use in this way while at the same time getting to rub him all over, watching the bubbles cover his body. Our tongues twisted together as I rubbed the shower gel into his chest and arms, my chastity device dripping as I do so.

He turned around and I start to rub his back, trying to keep my body as close to his as I could, especially when I came to his big ass. I made sure I cleaned his big ass crack well, not because it was dirty but because gave me a chance to have my hands next to his ass hole.

As I knelt down to wash his legs, his erect cock was right in front of my face, and I can't resist and put the whole length in my mouth. Gary gasped as I instantly took the whole cock straight down my throat to the point where I could barely breathe.

Gary starts to push back and fuck my mouth, the feeling of it deep inside me while I'm plugged and caged is almost too much and I start moaning and moaning. I can feel him tense as he is almost ready to explode and I make sure his whole cock is deep inside me.

Gary held his breath as I put every ounce of energy I can into sucking him deeper into me as his cock exploded. I could feel stream after stream going straight down my throat as a sense of satisfaction came over me.

I made sure that I had sucked every drop of cum out of his cock before standing up so we could kiss in the water once more.

"Right babe," he told me after a while. "I think it's time you got dry and left, we've got a big night tomorrow. Just make sure you take that lube with you and play with that plug plenty so we can have some real fun".

"Yes, of course," I replied with a grin on my face.

Just as I was finishing up getting dressed in the bedroom Gary came up behind me, using my hips to pull me next to his belly and kissed my neck making me weak at the knees.

"One more little treat for you hun," he said.

"Hmmm what's that then?"

He then pushed my back so that I was bent over at the waist and wiped the last of his cum on my ass. Even though I thought I had swallowed it all, my clothes were still covered in his tasty cum.

With that, he pushed me out the door, meaning everyone could see my ass covered in his cum.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
2 Comments
Glossy_CDGlossy_CD7 months ago

Good girl. Im glad he plugged your sweet ass. If only I could get myself into a similar situation.

Keep posting,

Love Glossy.

trikertony97vtrikertony97vabout 1 year ago

Hurry up and write part 3 please

Share this Story

READ MORE OF THIS SERIES

Similar Stories

How Did He Know? Pt. 01 Closet sissy can't fool black man at the bar.in Transgender & Crossdressers
But I'm a Boy, Not a Cheerleader! Accidentally a cheerleader at the basketball party!in Transgender & Crossdressers
A Surprise and an Impulse Johnny came home early and fell asleep on the couch.in Transgender & Crossdressers
A Key for a Discount What a girl will do for a cute outfit!in Transgender & Crossdressers
Fishnets / French Maid He wears his ex-girlfriend's lingerie - accidentally fucked.in Transgender & Crossdressers
More Stories