A Sub's Journey Ch. 05: Anal Virgin

If it's your first time dropping by, thank you for being here! This is another chapter in my series but each chapter is written so it can be enjoyed in isolation as well. So if this is your first one, please continue and if you like what you read, check out the other entries too. Enjoy!

We had been in a relationship for the past few months but only ever spent weekends together as we lived about an hour apart and had busy lives. My master did occasional work on a cruise ship and had invited me to accompany him for a week. This would be the longest amount of time we had spent together and I hadn't had a holiday in years. I was over at his house helping him pack, we were going to leave early next morning to go down to the docks to board the ship.

"So I have a very special plan for our week long holiday. This is definitely a big jump forward in pushing our boundaries but I hope you will be excited as I am. I think this is the perfect week to perform your anal training." He said. My eyes widened at the thought of a whole week, I didn't even know if anal was right for me yet. "But there's more. I think it should be an anal only week." He paused to open his drawer and he pulled out what looked like a g-string except different. It had thin black rounded straps, but unlike a g-string they were more rigid and instead of the fabric piece that covers the pussy, there was some sort of metal grill which was attached to the cord with a padlock. Around the back was a metal ring which I presumed sat around your asshole. "I want you to wear this. It's a chastity belt. Your pussy belongs to me and for the duration of our holiday you can't touch it. It will be locked off, we will be doing anal only." He was right, this was a huge step up in terms of boundaries, he wanted me to wear this all week. I had so many questions.

"Wow..." I said shocked. I had never seen this before, not even in the porn I had watched. "All week? How will I go to the bathroom? What happens if you lose the key!" I said jokingly. I knew he would have thought it through, he always had.

"Well it has these holes for you to pee through and I'll take it off for an hour at night to clean you and obviously if something gets real messy we can take it off." He laughed. "I have 2 keys, one I will keep with me and one I will put in the safe and I bought a cheap lock that can be broken with some tools which I have too as an emergency." It pleased me that he had thought of everything and my safety was still top of his priorities.

"OK then master, I trust you." I said in a sultry voice. I did trust him and I liked giving him even more responsibility of my body.

"Let me show you the toys." He pulled out more items from the drawer. "First I have this small training butt plug." It was one of those small, rounded stainless steel ones with a handle at the end, looking at that one, I felt quite excited to have it inside me to see what it would feel like. "Next I have this inflatable butt plug." He continued, it was a small black ball connected to a tube with a hand pump. "And finally I have these anal beads." I looked at them, there was no way something of that length could fit all the way inside me I thought. "And of course I have a metric ton of lube and our usual other toys I'll bring too." He smiled, he was in his element. I think he was excited to satisfy his kinky desires but also genuinely excited to push my boundaries and make me feel new pleasures. "So as tonight is the last time you will get to touch your pussy for a week I think we should have some fun..."

The next morning

As much as he wanted me to, we couldn't walk onto the ship with me wearing my chastity belt, they had metal detectors at the entrance and we didn't really fancy having to explain that one to security. But as soon as our luggage arrived at our room, it was time. I took off my panties and gave the area a good clean, I was started to wish I was clean shaven down there. I had we trimmed bush but I didn't want to get any hairs caught in the metal, too late now though. He helped me into the harness and we made some adjustments. The ring between my ass cheeks was tight and I could feel the general weight of the whole thing. It was going to take some serious getting used to but wearing it was a constant reminder of Him and our relationship which I loved. I couldn't believe I'd be walking around the ship, getting food and chatting to people and they would have no idea I was wearing this underneath. I put on a long, thicker dress and checked myself out in the mirror, you couldn't really tell I was wearing it for the most part, unless I pulled the dress very tightly to the contours of my body.

We had a fun first day exploring the ship, not getting up to anything too naughty. Occasionally if we got the elevator to ourselves he would feel the outside of my dress and tap on the front of the metal plate, teasing my pussy which was already desperate for the touch of his fingers. Using the toilet for the first time with it locked around me was a strange experience, it worked well enough. After a full first day we got back to our cabin ready for an evening of anal training. We kissed and he took off all of my clothes and we both starred into the tall mirror, looking at my dressed master behind me, and seeing myself completely naked apart from my belt was a visual reflection of our roles. I loved to submit to him. He lay me down face first on the bed and began to give me a massage.

"The key thing about anal, is being relaxed." He said as he began to massage my back. "We need to take it nice and slow, you need to try and relax and let your body adjust." His massaging hands slowing moving from my shoulders to just above my ass.

After that he moved me around and got me to lie off the side of the bed, so my breasts were laying on the mattress, my ass over the edge and we found something for me to rest my knees on. He was finding a position that I could be comfortable laying in for a while that also made my ass relaxed, open and the central feature of tonight's entertainment. I heard the cap on the bottle of lube open and squirt into masters' hand, then I felt the cold lube being spread around my tight, sensitive asshole.

He circled the lube around it a few time and then I felt a warm finger sliding into my tight asshole. The massage had done a good job of relaxing me as it slid in with relative ease. He started to finger my ass slowly and gently, his finger getting slightly deeper with every other thrust. It felt totally different to my pussy. In my pussy I could feel almost every touch, its sensitive in an accurate way. In my asshole I could feel a fullness, It was sensitive in a stimulating way but I couldn't pin point it. Above all though, the sheer naughtiness was what was doing it the most for me. He fingered me for some time pulling out to re-lube and then inserting again, so far there had been no pain.

"You're being a good anal slut aren't you? How does it feel?" He asked me in his master voice.

"It's good master." I replied slowly, my face and body comfortable lying on the bed. I could feel my pussy behind the grill was gaping and wet, I was finding it intensely sexy, but so far I didn't think I was going to be able to cum from anal play, but I loved letting him explore.

"Next I'm going to slowly stretch out your ass." I could see he had picked up the inflatable butt plug. "But this one might make you moan or squeal a little bit, and I think the walls of these cabins are rather thin." He pulled out a ball gag from his suitcase of toys, I let him put it on me and he pulled the straps right around my head. My heart rate started to increase, I knew I could shout out our safe word if it got to much, but the anticipation of quite how this would feel was hitting me. The deflated ball was still larger than his finger. I exhaled quite loudly through the gag as he inserted it into me, it may have hurt for a nanosecond but it was more the shock of it. He started inflating it slowly. It didn't take long before I could really start to feel it pushing against the walls inside my ass. It felt good. I started to moan a little. "Just hold out your hand when you need a break." He said. Which I appreciated but also made me wonder what he knew that I didn't. He kept squeezing and the plug kept expanding. My ass felt so full, so much pressure, I let out a large moan and squeak as now it felt like my ass was full and could not accommodate any more. I held out my hand. Suddenly there was a knock at the cabin door.

I could not be in a more compromising position. "Stay here, I'll be right back, don't worry they won't see you." He said. I trusted him that they wouldn't be able to see me, but there was also part of me wondering what if someone did. Maybe that would be kind of hot too. I felt like my ass was starting to adjust, still feeling stretched though. "It was just the cabin steward." Master returned. "Are you ready for more?" I was gagged but still able to just about communicate.

"Let's try one more." I muffled, my heart was pounding, I wanted to push myself, I heard the squeeze of the inflatable, the pressure inside my asshole multiplied as the plug pushed against the walls. I was definitely at the limit. I moan and squirmed a bit, I was enjoying this but definitely no further, I held up my hand. He gave me a little spank on the ass cheek and I felt it right inside my asshole. He gripped the end of the butt plug and started tilting it a little in different directions. My pussy was so wet I thought it must be been dripping through the front of the grill. I was just laying on the bed, unable to satisfy my pussy's desire but letting the intensity flow through my body. I don't think I'd ever been hornier.

"You're such a good girl, you have done amazing." He said. I felt his hand on my ass stroking my cheeks. He let the air out of the plug and it contracted. My body contracted back down and my heart was pumping. It hadn't made me cum yet, I didn't know if that was going to be possible for me, but it was intensely naughty and I enjoyed the experience. "Let's get you cleaned up. I think tomorrow night you will be ready for my cock."