Away from Home Fun Pt. 03

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A crossdresser spends their final night with new lover.
3.9k words
4.78
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Part 3 of the 3 part series

Updated 07/26/2023
Created 01/28/2023
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I had never felt so self-conscious, than walking back to my room with another man's cum on my ass for all to see. There was no way to hide it either as my bomber jacket didn't go low enough, I just had to hope that nobody noticed.

I think I did fairly well, most people in the corridors were quite a way behind so hopefully they didn't see but all of this changed when I got into the lift. I was so eager for the lift to arrive as I was standing there, conscious everyone could see my cum covered ass, that was until the lift doors opened and my heart sunk when I saw how full it was.

Sadly, it wasn't so full that I couldn't get in but there were four or five people in there already, and I knew that it was going to be a very long trip down. I knew that my shiny trousers could just about pass as men's clothing but having them covered in Gary's cum made it obvious I'd had fun with a man.

My heart was racing as we slowly dropped down floor after floor and I knew anyone in the lift could see the cum on me. A couple of floors down even more people got in which meant I was really close to the others behind me. Whilst I was standing there, trying not to attract any more attention, I felt the unmistakable feeling of a hand caressing my ass and it almost made me instantly cum in my chastity cage.

I had no idea who it was, it could have been one of the men or women, but they were definitely playing with the cum on my ass and tracing the lines of my ass. Despite how unbelievably horny it made me; I just had to try and stand there looking normal. This continued for a few floors until quite a few people had to leave from behind me and the mystery person grabbed a strong handful, really digging their fingers in which really made me feel weak at the knees. Even looking at those who had got out of the lift I couldn't tell who it was or even if they were male or female as none of them looked back.

Thankfully, the rest of the trip back to my room was much less eventful and once I was back in my room, I was able to see what my ass actually looked like. My whole ass seemed covered; it must have been so obvious to everyone but what else could I do?

After taking off my trousers and cleaning them in the bathroom so they'd be dry for Gary again the next night, I ran myself another girly bath full of bubbles to come to terms with another evening sucking a man's cock.

So that I was as prepared as possible for the next day, I also lay in just my satin chemise and played with my butt plug. Much like earlier with Gary, it was quite uncomfortable at first, but it slowly got better and much more pleasurable until I eventually fell asleep with exhaustion.

I had another restless night's sleep thanks to my arousal but waking up with an ass filled with butt plug was amazing and looking at the inside of my chemise I could see how much my locked-up cock had leaked in the night.

Although I felt like I couldn't wear my plug for work the next day, I could at least play with it for an hour or so before I left.

I worked so hard during the day to finish the project so that I could spend plenty of time with Gary before I headed home in the morning. Although I managed this, I once again wanted to serve and pleasure everyone I interacted with.

Once I got back to my room, I wanted to get my outfit ready and choose what it would be, but it didn't actually take long as there was only one outfit that I'd brought which he hadn't seen. Thankfully, it was also what I considered to be my sluttiest.

I laid the outfit nicely on the bed while I went for my last bath before I let Gary fuck my ass. The whole bath was spent playing with the plug again and straining against my cage. When I left the bedroom in my satin robe and saw the clothes on the bed, I knew that it was my destiny to be used by my man.

I took my time putting on the black fishnet stockings first, making sure they fitted perfectly as I ran them up both of my legs. Even though normally I wear quite a few pieces of lingerie at the same time, knowing what was going to happen I didn't want to so I put on the only other item of lingerie I would wear for my man, my night dress. It was much more like an actual dress than a chemise as it was very tight fitting and only just covered my chastity device and you could see the bottom of my ass when I was stood straight. I slowly slipped it over my head and pulled it tight down my body, looking in the mirror I loved how the satin leopard print panels running down the middle of the front hid just enough but the mesh panels everywhere else really showed my ass off.

After fitting my stockings to the suspender straps, I looked in the mirror and actually got turned on by myself which made me strain against my cage. I also bent over and confirmed my suspicions that there was great access to my ass, perfect to allow Gary to fuck me later.

Before I could get too excited, I made sure that my butt plug was nice a snug in my ass pussy and put on my male clothes to head to the bar.

Sadly, I wasn't groped in the lift again, but I still loved standing there with other people, knowing I was dressed like a slut under my normal clothes.

When Gary came over to the table holding a bag it almost felt like a normal relationship and we just chatted with my hands on his thigh like we normally did.

"I have got a surprise for you that I hope you'll agree to" Gary eventually said with a cheeky smile on his face.

"What's that?" I replied curiously.

"Well in my bag I've got a slightly bigger plug that I'd like you to go put in."

"What? Now?"

"Of course, take the bag and go to the toilet to change. There's some lube in there too."

"Err, ok I suppose" I replied nervously as it seemed a little too public, but I was also the horniest I had ever been so how could I resist.

Thankfully the cubicles were empty, which meant that I at least had some privacy as the plug seemed a little bigger again that the last one, I had been playing with. I was also glad that I could easily get to my ass as my lingerie was so short. I was purposely careful as I didn't want to cause any damage before my big night, so I very gently removed the first plug. Although the first time I did this it felt a little weird by now it was almost second nature and just left me wanting to be filled once more.

I looked at the new silicone plug and it suddenly looked massive, so I made extra sure that both it, and my ass pussy, was fully lubricated. I bent over as much as I could in the cubical and started to press the tip against my hole and slowly started to insert it deeper and deeper. Just as it was at its widest, I heard the door to the toilets open as someone entered. I froze and waited for what seemed like an age until they left as my ass pussy was stretched as much as it ever had been.

When the person had eventually left, I could finally relax, the last of the plug was sucked inside me and I let out an audible gasp of pleasure. My ass had never felt this full, and I felt like such a slut, ready to be fucked.

Once I had recovered, I left the toilets and made my way across the bar where I could see Gary sitting there with a grin on his face as he was looking at me with his phone in his hand.

Suddenly I had to stop in my tracks, my plug, all by itself, started to vibrate. At least I thought it did as it stopped suddenly too but as soon as I started to move it happened again before stopping.

That's when I heard Gary laughing to himself.

Although it was tricky with various vibrating pulses from the plug, I eventually made it over to Gary and sat down next to him an immediately put my hand so high up his thigh that I could almost feel his enticing bulge.

"So did you enjoy my little surprise?" he asked with a chuckle.

"I really did, it was just a shock".

"So, you didn't enjoy this?" he said as he pressed an app on his phone which once again sent vibrating pulses through my filled ass.

"I... errr... just..." is all I could manage to say with the waves of arousal that were coming over me and I squeezed his thigh tightly.

As Gary stopped the vibrations again, it allowed me to catch my breath, and I suddenly became very aware of how full the bar seemed to be and how I didn't want to raise suspicions.

"Why don't you get us both one last drink," he said before leaning right in and whispering, "so that after we can go upstairs, and I can replace that plug up your ass with my cock".

I smiled as we looked into each other's eyes, and I couldn't resist it any longer and I kissed him, in public. This was the first time I had shown such obvious affection for a man in public, but it just felt right. It was only a short kiss but we both knew how much it meant to each other and how much I was his.

Gary had great fun on my walk to the bar again playing about with the vibrating butt plug in my ass, I think he just loved watching me squirm. The whole time I was stood at the bar waiting the plug was vibrating away. It felt wonderfully emasculating to be stood amongst loads of men and beautiful women knowing that I was wearing lingerie, had a butt plug vibrating up my ass, and my cock was locked away so that I couldn't even get hard if I wanted to.

Thankfully, Gary stopped the plug vibrating as I started to order our drink but then, just a second or so later, he made it vibrate even more strongly than before. I could barely get my order out it felt so good, and I could feel pre-cum dripping in my cage.

During our last drink Gary made the plug vibrate on and off lots of times which drove me wild and he loved watching me squirm as I tried to control myself.

"Come on babe, let's go fuck" Gary eventually said. I'd never felt like such a slut before but how could I resist when I had been denied an erection for so long and he turned the plug on for our walk.

This time Gary didn't just have his hand on my ass the actually put his hand down my trousers, resting his big chunky hands on my ass cheek was he walked me through the bar. Everyone in the bar who saw this knew that I was his property that he was going to use, and I loved it.

Sadly, the lift was full so he couldn't hold my ass anymore but that didn't stop him from having some fun. The second the doors closed he turned up the butt plug to what must have been the maximum and I felt like my whole body was shaking. The feeling was so intense that I actually let out an audible moan which made me feel so embarrassed, everyone in the lift must have heard it.

Gary didn't even turn it down on the walk to his room, so I really struggled to walk down the corridor.

The second I was in his room, even before the door was fully closed, I was stripping of my clothes off as I just wanted to be used.

"You look perfect," Gary said as he looked me up and down in my lingerie "now get me naked".

"Of course, Sir, I'd love to".

I helped to take his t-shirt off and my instincts took over and I just held him close, the feeling of his fat hairy body in my arms as my ass was still vibrating full pelt. Once I got his trousers off, I immediately almost ripped his boxers off and put his whole cock in my mouth in one. All of the chastity and butt plugs had worked, and I just wanted him inside me. I sucked as hard and as quick as I could as Gary seemed to grow bigger than ever before in my mouth.

"Please will you fuck me?" I begged as I looked into his eyes as I kissed his gorgeous sweaty shaft.

"If you think you've done enough you've got another thing coming babe" he told me surprisingly sternly.

With that he went and lay on the bed with his big belly looking gorgeous and so inviting.

"No why don't you come over here and carry on putting that tongue to good use".

I moved over to the bottom of the bed and all I could see as I looked up from the bottom of the bed was my lover relaxing with his legs open, his gorgeous big belly and his hard juicy cock, begging to be licked.

I moved up the bed between his bent legs and started by kissing his big hairy balls, they felt so good against my lips that I couldn't help but suck them. I was obviously something that he liked too as I felt them tighten and him moan as I did so.

Next, I started to kiss the base of his cock, not just a few small pecks but full on open mouth kissing it, trying to fit as much of it in my mouth as I could. I slowly worked my way to the tip, making sure I kissed every inch.

When I got the tip of the cock I couldn't resist and just took the whole thing straight down my throat. I loved sucking his veiny cock so much I kept on going from base to tip over and over as he groaned.

After a while I went back to licking as I wanted him to last as long as possible, especially when he came to fuck me. As I was licking the base of his cock, Gary grabbed my head and I thought that it was to push me harder onto his cock, but it wasn't, he was pushing my head towards his asshole as he opened his legs even more.

It took me a second to realise what he wanted me to do but then it hit me that he wanted me to lick it. It was quite intimidating at first, he had such a big ass, and my head was being pushed towards it but I thought I might as wall at least try.

As Gary spread his big ass cheeks I could clearly see his asshole but rather than go straight in I decided to start my licking the whole length of his crack. Although I knew it was only the start, as soon as my tongue tasted his sweaty crack I knew I was in love with licking men's asses. I dove in and started to tongue his hole and buried my face in his ass, the feeling of being surrounded by his massive ass cheeks was so good I could have stayed there for hours as my chastity cage felt like it was going to explode with how much I was straining in it.

Soon, Gary lifted my head and said the words I had waited days to hear.

"Why don't you get on all fours and I can give you what you've been waiting for".

He didn't have to tell me twice and I immediately did what I was told, knowing that my ass was clearly on display in my very short lingerie. In that moment I suddenly got nervous and had to control myself from shaking as I knew it was what I really wanted.

Gary must have been able to sense my trepidation as he promised me, he'd be gentle. I felt so vulnerable, on all fours with a real man behind me, looking at my exposed ass ready to be fucked gently, he removed my butt plug taking his time so that I felt truly empty without it. I almost jumped as the cool lube got squirted on my ass but any fears I had evaporated as I felt his finger start to rub and penetrate my hole as his finger went deeper and deeper.

Now was the moment I'd been waiting days for, I could feel the tip of his rock hard cock against my virgin asshole. I couldn't help but moan as it slowly started to stretch me, it felt so good that I even tried to stick my ass out. When his cock popped in my ass I couldn't tell if I was feeling pleasure or pain but as his cock got deeper, I couldn't even hold my upper body up and my head dropped into the pillows which only made my ass stick out more. As he put his whole cock in my ass, we both let out a moan, it felt to have his big belly rest on my ass as every inch of his cock stretched in my ass.

If I'd have known how good it was to be fucked by a man, I'd have done it years ago but while I was being fucked, I decided to make the most of it and started to push my ass back towards Gary, trying to make him go even deeper. Gary's first move was to pull almost the whole way out and I thought he was going to until he went balls deep again, grabbing my hips as he did.

I couldn't believe how feminine I felt in that moment, I could barely think of anything other than how amazing it all felt.

As Gary picked up his pace, I could feel my caged cock constantly dripping pre-cum and this is when Gary asked me to flip on my back. When he pulled out, I felt so empty, I was just dying for him to start pounding me again.

As I lay on my back with my legs apart, Gary loomed over me and he rested his cock on the edge of my ass pussy. With barely any friction he slid the whole length in, making my eye roll back with pleasure. Gary started to speed up again and as he did, he leant forward onto me pushing all of his weight onto me, pinning me down as he fucked my hole, I never wanted it to end.

The he started to speed up, pounding me faster than he had all evening. I just loved looking up at his big sweaty body as he started moaning and pushing all his weight onto me.

"That's it baby," I moaned "cum in my ass, I need your cum in me".

With that, his cock seemed to grow in my ass even more and he pushed every part of it deeper as all of his cum exploded inside me. Both of us screamed with pleasure and my eyes rolled back as pulse after pulse of cum filled me up.

It amazingly seemed to go on forever until he let out one last grunt and he collapsed on top of me, holding me close. There was no way I could move from under him, but I didn't want to, I just wanted to lie under my lover forever as my body shook with pleasure.

As his cock started to shrink in my ass he eventually pulled out and I lay in his arms, both trying to catch our breath.

Lying in his arms, next to his hairy, sweaty belly, I felt so secure as his cum slowly started to drip out of my ass and we both fell asleep, him with empty balls and me dripping in my chastity cage.

I woke up the next morning with a sore ass just as Gary was getting out the shower. He must have said something, but I didn't hear anything, all I could do was stare at his dripping wet belly, hoping to see what was under his towel once more.

Without saying anything I got to my knees, still in my cum stained lingerie, ripped if towel off his waist and plunged his cock into my mouth. It somehow tasted better than ever before as it took no time to grow and grow.

In no time at all it was as big as possible, and I once again took every inch and buried my face into his gorgeous belly. As he was getting close he grabbed my hair and pushed his cock in as far as it would go and exploded once more down my willing throat. I have no idea how he still had cum inside him after last night but I'm so glad he did as it meant I got to taste him once more.

"Thank you, baby," he told me as I looked up at him from my knees "you did amazing".

"It was absolutely my pleasure gorgeous".

"I wish I could fuck you again, but I've got to go".

I could almost cry but I always knew it was always going to be the case so I slowly put my male clothes back on and we exchanged number so that we could hopefully meet again.

Just before I left, he stood towering over me and moved my chin up so we could kiss one last time and I let out a small moan as precum dripped once more from my caged cock.

Making my way back to my room I felt like everyone I saw knew what a slut I'd been and could smell the cum on my lips even though I knew they couldn't.

I found it hard packing up my girly clothes to leave, partly because I never wanted to wear male clothes again but also because every time I touched something silky, I almost orgasmed in my cage.

I really found it hard driving home, my mind was swimming with thoughts of being fucked and getting home to finally release myself from my cage. As I pulled onto the drive, I knew that after last night I would never be the same again.

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