I’m going to be honest. I was terrified for Tuesday, our first play-date.
We had been texting regularly since our beach day on Thursday, and I was still very interested in Master, and curious about the role as a sub. But still very hesitant. In fact, at once point Master e-mailed me an agenda:
Presenting for Master
Bondage & breast bondage
Anal play in bondage
Forced orgasms in bondage
Orgasm denial in bondage
Humiliation and degradation
Past punishments due
Forced orgasms under duress
Breeding Whore’s ass
Needless to say, I was insanely intimidated. As somebody who had only had normal sex in the past, I panicked. I responded asking to slow things down. I felt sick in the pit of my stomach, thinking that this attractive, funny, interesting man would lose all interest in me. To his credit he responded with:
“We don’t have to. I just wanted to touch on a broad stroke of things to see how you react to them so I could get an idea of where to focus in on things. However you want to proceed with play is completely COMPLETELY up to you. If you want to continue much like we did with the wax, we can certainly do that.”
It was as I read this that I knew he was going to be the perfect master for me. I had been doing some research on my own, much of which said early on the sub can set limits, and that the master should never intentionally want to cause harm to them. So I was very happy that master fit that description, and pleased that he didn’t want to rush at a pace I wasn’t prepared for. I went to sleep, once again confident that this was going to be a fun journey.
Tuesday morning. I woke up early and had a nice long bath. As requested by Master I wear a dress with no underwear. I put out 2 towels, and the various toys and tools that I have available. A candle, a collar, a riding crop, a whip, butt plugs and nipple clamps. I had no intention of using all of these things, but wanted them available if things went that way.
Master arrived in the morning, and greeted me with a kiss. I led him to my bedroom and shut the door. He had a backpack with him, out of which he took out 2 kinds of rope, a pocket knife, and proper restraint cuffs, lube, and condoms. Between the two of us we were really ready for anything.
Now bear with me, as I’ve never had to summarize experiences like this before. I’ll try to be detailed. First we just kissed and talked and took things slow. As the kissing heated up he told me to get naked. I obliged master and took off my dress and bra. Master then told me to turn around and assume doggy position on the bed. Again, I listened. He took my arms behind my back and restrained them with the cuffs. I realized now how just having one restraint incorporated I could be so helpless. There I was bent over, face against the bed to the side with my ass exposed in the air. Master rubbed and slapped my ass as he started to play with my pussy. This felt amazing. As a general rule i’ve always loved finger play, and this was no exception. He then started to play with my ass as well, pouring lube all over it. Let it be known that I have next to no experirence with anal sex, and was very nervous.
Over the next few hours master played with my clit using my vibrator as well as playing with my ass. He was able to get up to the medium sized butt plug while doing so. Now I lost count of how many times I got off during this period at 15. Once I cum my clit gets very sensitive, and I typically cease all touching there, but master would not allow that, and would not stop when asked. I learned that this is called forced orgasms. He just kept going. It felt awful but so amazing. Then he would keep playing but demand I not get off. So I would have to try to restrain myself and psychologically overcome the feeling until master allowed me to come. At times I would be begging to be allowed, and he would make me wait.
Master then allowed me a small break. He removed the cuffs so I could stretch, but I was required to keep the butt plug in this entire time. After the small break I was commanded to resume position, and he once again restrained my hands behind my back. Next, Master moved on to introducing me to pain. He started by lashing me lightly with my new whip. He would get harder and harder each time. After a while he checked in to ask if it hurt, I said “yes”. “Good hurt, or bad hurt?” The response of course was good hurt. I was hooked. He then also whipped me with the riding crop. After a while he went back to play with my ass and my clit at the same time, occasionally fingering my pussy. Then he uncuffed me, and had me flip over, and restrained my hands in front. He went on to lash and whip the top of my body, from my breasts down to my thighs. Then he lit a candle, and poured hot wax all down my body, focusing on my nipples. Once the wax cooled he whipped it off with the riding crop. By this point my nipples were very tender.
Once he was rid of the wax he had me turn back into doggy, with my arms restrained behind me, and once again went on to butt play. This time he took out the medium butt plug (which had been there all this time) and eased his cock into my ass. This hurt a little. He reminded me to breathe, and slowly I was able to take much of his cock. He allowed me to push back on it at my own pace. After a bit he then took his cock out and started to try and work in the largest of the three butt plugs. This is the only time in our entire adventure I asked him to stop as it was very painful. He obliged instantly, and instructed me to slowly pull forward off of the larger butt plug. He undid my restraints and I collapsed.
He crawled into bed with me and held me. I’m not sure how long we were like this, frankly all I remember was my body feeling like jelly, feeling almost drunk, and not being able to put together words, as he tried to discuss what I did and didn’t like about what we had done so far. I think this is what they call subspace. It was like I was in another world.
Once I got myself together he had me stand up. Next he pulled out the rope. He cut off a fairly lengthy piece and started to wrap it around my breasts. Occasionally going through the middle, and a couple of times around my neck, almost like a halter top. He kept getting tighter and tighter until my boobs felt like they would explode. He tied the rope and left them this way for a while. During which he licked and bit my nipples. He also whipped them, then attached the nipple clamps to my already very tender nipples. After a bit of kissing and teasing, he slowly unraveled the rope, my breasts hurting more each time they loosened up, and then once they were loose he pulled the clamps off. I don’t think it would be over-exaggerating to say that this was the most painful experience of my life. This all only happened yesterday, but my nipples are still incredibly sore.
Once my breasts were free we played around with a little more touching and whipping, until it was decided that it was Master’s turn. I mean, he had only gotten me off a couple dozen times, surely he should cum as well. I easily spent the next hour playing with Master’s cock. I’m not just saying this for entertainment value, but he has a really great thick cock. I loved hearing his reactions to the different ways I would move my tongue, and the little sound he makes when I would play with his balls just right. After sucking his cock for a while I asked “Master, can I ride your cock?” “You may whore”. I smiled and climbed on top of him, sliding his cock inside me. Another thing that should be noted is that I get very wet. Definitely above average dripping (especially since we had been playing for what has now been several hours). Once I got off again on his cock I moved back down to sucking. He grabbed the back of my head and forced his cock up my throat. He said “You’re going to have to learn to deep throat this cock if you’re going to be my Whore”.
Shortly after I was able to get Master off, happily swallowing all of his cum. And as I was taught I said “Thank you for letting me please you Master” and he responded with “You’re welcome Whore”. I then once again collapsed beside him, and we held each other for a while.
Now any further details are probably not at all interesting after what I’ve done my best to summarize. We talked, discussed the roles a bit further, talked about what we liked, where I need to improve, that kind of thing. It was decided he would go home for a bit, and then we’d spend the evening at the beach.
I really must say, that if this is what being a submissive is, I can certainly get used to it.
Now it’s 1:30 am Thursday morning, and I have to be up early as I’ll be seeing master again during the day, and I haven’t yet done my homework. I’m a bit worried for what the punishment for that will be, but I really feel it’s important to keep this blog up to date, and to get as much detail down before time passes and it’s less clear in my mind.
I expect today to be much less vigorous, as I’m still recovering from Tuesday. Let us hope master will be kind. I’ll leave you with this picture of my ass, after my first flogging ever.