Painful orgasm

I woke up horny. Last night's anal training was intensely sexual but it didn't make me cum and I was on day 3 wearing this chastity belt and desperate for someone or something to give my pussy some attention. Still lying on my side in bed, I reached around and lightly grazed my finger around my asshole which was accessible through the ring on the belt. It still felt a little sore after the stretching done by the inflatable butt plug last night, it wasn't painful as such, it was just exhausted after being stretched, like how my pussy would feel the morning after it had been pounded deep and hard for a good hour. My master's cum training was also working, I felt this intense lust for his cum, my mouth had a craving to remind itself of the taste of his thick load.

We spent the morning out and about the ship having some fun, I still had my chastity belt locked on of course but we didn't get up to much funny business. We went to the buffet to get some lunch and sat by the window.

"So today is the day I am going to fuck you in the ass, are you excited?" asked Master, catching me off guard, I loved it when our kinky sex life crossed over into the normality of life.

"Yes master." I replied with a shy smile and a look into his eyes.

"We're going to go back to the room soon and you'll wear a butt plug until this evening just to warm you up."

Back at the room I bent over the bed again like I had done last night, and felt the cold, well lubricated plug push into my asshole. It took a few attempts before I was able to relax properly but when I did, it slid in with ease. I stood up, I could feel it in there, a sense of fullness, I looked in the mirror and just like before there I was looking like a perfectly normal woman, in my full summer dress with my tights on except for the hidden chastity belt and now butt plug that I was wearing. I was praying there was no way it could fall out as I went about the rest of the day on the ship together. As soon as we got outside our cabin I clocked eyes with a neighbour two doors down. I felt like somehow they knew I was such a dirty slut, but they soon dropped their eyes and carried on with their business. Part of me almost wanted him to know I was.

The submissive, naughty feeling I had walking around wearing the chastity belt was heightened with the butt plug in, it wasn't uncomfortable, it was a constant level of pleasure, I was being teased all afternoon occasionally when we were alone Master could put his hand under my dress and wiggle it around to check it was still there. After a few hours it was time to go back.

We got back into the cabin and the moment the door was shut he pushed me against the wall and we started kissing passionately. It was so intense, the whole trip had been leading to this, I was about to get fucked in the ass. I was sort of nervous for some reason but incredibly horny. He took off my dress and kissed my breasts. He then took me by the hand over to the bed.

"I want you to watch." He said to me,

"Watch?" I replied confused. He laughed.

"Yes, I want you to watch me fuck your ass."

"How?" I replied, still confused.

"Give me a moment." He laughed, "Stay there, no peeking." I heard a lot of shuffling around, unzipping suitcases and plugging things in, then he gave me his phone. On it I saw a live view of my fairly close up to my butt, perfectly positioned with the tail end of the butt plug poking out. I reached my hand around and placed it on my ass cheek and sure enough the video showed my hand on my ass.

I watched him spread my ass cheeks apart. "It's easier if you help push it out" He said, I dutifully listened and pushed out the plug and he pulled it. Such sweet relief after it had been in all afternoon. Master kept my ass cheeks open as the plug came out trying to gape my asshole but I watched as it quickly closed back up again. He put a condom over his cock and applied lots of lube, then I watched and felt as he squirted some onto me and massaged it around my opening. It was finally time.

I watched and felt him push the tip of his hard cock against my asshole, it slid in with ease and unlike when the butt plug first went in, this time it was warm. I watched as he pushed his cock in about half-way and then he paused letting my asshole adjust to him. Watching it happen on the video and feeling it at the same time was a surreal sensation, it was like I couldn't experience both together, I could either watch or I could either feel but it was hard to concentrate on both. The butt plug and the training had prepared me well, I felt every inch of it inside me but it did not hurt. He slowly started to thrust, only moving his cock slightly, making sure the lube had time to spread out inside me, his thrusts got a little bit deeper, every other thrust inching his cock slightly deeper inside me, I wondered how much of it I could take. The pleasure of him fucking my ass was much more intense and enjoyable that the stationary plugs, I was one with him again. My hand instinctively moved towards my pussy to play with my clit only to meet the cold metal of my chastity belt, I had to settle for playing with the nipples of my breasts instead. Watching him on the phone his cock in my ass was incredible, I was my own porn star, I had these moments where I was watching his hard cock in my ass and I could not really believe it was me. I felt like the most dirty slut in the world. I loved every second of it.

"Deeper" I moaned involuntarily. I had been horny for days now and it was taking over my whole being. My master slapped my ass cheek in exuberant acknowledgment and he paused his thrusting to intentionally make me feel his cock slide in deeper, I watched on the phone and he pushed it in as deep as he could, his cock has all but disappeared inside my asshole and his pubic hair tickled the sensitive are around my opening. My asshole felt well and truly open and ready now.

"Faster" I moaned as I squeezed on my breast hard, desperate to cum "Please fuck me harder master". Another slap on my ass cheek from my master as he really started to pummelled my asshole. I love being fucked from behind like this the whole force of his body slamming into me and pushing me down into the bed. He was breathing heavily and was nearly ready to cum, which was fortunate as my lust was starting to out-weigh my body's ability to take it and things were starting to ache, he did one final thrust into me and I felt his cock jerk around squirting his load into the condom. He leaned over me, his cock still inside me.

"That was incredible. He panted, did you cum?"

"It was amazing, I can't believe we did it." I panted back. "I was incredibly close no I didn't."

"I see, well you have been such a good girl for a master..." He pulled out his cock and if it could my asshole would sigh of relief as much as it enjoyed it, it was ready for a well earned rest. He rolled me over onto my back, took the key from the bedside drawer and opened the metal plate of my belt to access my pussy. He took off the condom and poured his cum out of it onto my clit, then he slid his dick straight into my wet, gaping pussy, using his cum as extra lube. There was no foreplay required, we both knew it and within about a minute of him fucking my pussy I came hard.

I just lay there on the bed absolutely shattered, my whole body satisfied from head to toe. He lay with me.

"You have an amazing asshole." Master said to me,

"Thank you. It was incredible, I didn't think it could be like that."

"Do you think you could cum from it in the future?"

"Maybe, with practice and time, I felt close, certainly with some clit play I could."

"Good." Master was still panting a bit. "There's so much more I want to do with you."