First Punishment

It was two hours passed the time Sir had asked me to arrive at his place. I couldn’t help it though since I was required to do my first enema earlier during that day, which resulted in my having to use the restroom more frequently than normal. Sir had requested a specific outfit for me to wear, which was a school girl plaid skirt, see thru black lace shirt with no bra and black boots. Oh and who can forget the favorite panties part? I really didn’t want to wear this but he insisted. So I changed into it about a block away from his place and at this point I shocked myself by how nervous I was. I began to sweat, which is unusual for me. By the time I got to his door, I was not only sweating, I was also shaking. I really didn’t think I would be that nervous, but after all that I had already done, I was not about to give up now because I knew Sir didn’t want me to and I did not want to disappoint him.

Sir and I had been talking for quite some time prior to this encounter that was about to happen. We had many laughs, frustrations, irritations, general discussions, serious discussions …..and I know that during this time of getting to know each other, Sir had come to the conclusion he wanted or needed to “fix” me. I had been somewhat defiant, mouthy and pushed Sir to his limits, hehe. Due to this sort of stuff, I had accumulated many minutes of punishment. Even though I had never experienced punishment, and I was well aware of some of the things that a punishment may include, little did I know how much it really does serve as a punishment. I was told I would be in pain, and cry. I don’t think I actually realized the truth in this.

So after putting the funny looking goggle blindfold on and Sir opened his door, I could barely walk since I was shaking so much. I think he found much amusement in this, but did what he could to ease my nerves. He took my hands and led me to a spot where he then questioned me a little on who I was and why I was there. He made sure I had told at least someone where I was and given them his address or phone number. I felt safe and gained even more respect for Sir at this point because I knew he was doing this as a safety measure.

Then he reminded me of the punishment I had earned, Sir told me to raise my hands high above my head and keep them there. He took his time removing my clothes which was the first of my sexual arousals. He clamped some things to each nipple….I freaked and yelped, lol as I don’t tolerate nipple pain very well. After a short bit he removed them, thank God!!!! Then he sucked on each one and I thought I was going to fall to the floor melting because his lips were so soft and it turned my on so much to have his mouth on my nipples. Damn.

Then the spankings began, the beginning of my punishments. Throughout, Sir asked how my arms were doing and how long I thought I could hold them up. I was more worried about the pain and burning sensation on my ass than I was my arms! Eventually I asked if I may put my arms down, and he allowed it. He then walked me to another spot which I could tell was against a bed, taped my legs together and bent me over. After he used some more items to spank me, I started begging him to stop and apologizing for what I was receiving the punishment for. I even felt myself begin to cry and felt pathetic for it.

Eventually and thankfully the ass beating ended. I am sort of unsure of the order of the way things took place, but I know Sir used a ten inch dildo inside my pussy (and no the whole thing didn’t fit), he fingered me, ate my pussy….yum. He, grrrr put some anal beads in me which I fought. Haha. He kissed me, which I very much liked but kept wondering if he was liking how I kissed him back because I know he gets super turned on by kissing. We talked, relaxed for a moment and then he announced it was time for another punishment. I was like what?!

So this time Sir chained me face against the wall. He used a flogger on my back, and holy crap I was sorry for what caused that punishment, REAL quick. I have not ever experienced pain like that from a flogger before. I definitely needed to cry on this one. I screamed so loud. The neighbors had to have been woken up by me. I actually kind of thought he was going to get mad at how I was acting about the flogging, because I was saying "Fuck" and screaming "that fucking hurts" and to "stop". Sir says he was even easy on me, so perhaps I’m a wimp? I don’t know, but I do know that my back is bruised and welted now. I really had no energy for a short bit after this. I just stood there in silence against the wall trying to recuperate. During this time is when Sir decided to find some more amusement in calling my sister to let her know I was ok, but not only that, he decided to ask her how to punish me next. He told her that I was a good kisser and that he loved my tits, so that made me happy, ha.

After a short discussion with her, they came to the conclusion of using candle wax on me. I was actually curious about this, and thankful to not be flogged anymore. Sir released me from the chains that held me to the wall and lay me down on a bed. He dripped candle wax all over my back side, which was very interesting. Some spots hurt but mostly it was just fun for a different sensation. Sir likes to get a rise out of me and purposely does things to get a reaction out of me and said it would be very painful to remove the wax. Well, he vacuumed it off of me which kind of made me laugh and was not in fact painful. He is funny, because he put the flippin vacuum hose on my pussy. It kind of felt good on my clit.

Sir then chained me up again while I was on my stomach, using a leg spreader bar, collar, and had my arms behind me. He used a dildo in me again, and started messing with my asshole again, grrr lol. Uh, I should mention that was an interesting moment….

Again, I am not sure of the order of things but I know that Sir licked and fingered my pussy with a butt plug in my ass. This was actually very arousing, and I loved it. Especially when he played with my nipples. Mmmm, yesss.

Sir had me on my stomach at some point with my hands handcuffed behind my back. He ordered me to put my ass in the air. I seriously did not want to, as ass play is new to me. I told him “no” which was a mistake. He started smacking my raw ass and immediately I was sorry and actually immensely aroused. As much as I didn’t want to present my asshole to him…..I liked how he doesn’t take no for an answer. I was mortified and embarrassed, but I did what I was told. So I managed to scoot back up to my face was burried in the bed and my ass and pussy was completely exposed to Sir and he licked my ass which wasn’t so bad, but was embarrassing. He also fingered it and took the dildo out of my pussy and started to put it in my ass, I started screaming lol. Again, I think he was just trying to get a rise out of me……so typical

At some point Sir asked if I was ready for my last punishment. Man, I thought it was done and over with already!! I got another set of anal beads shoved inside me and he said I had to wear them for the rest of the time. I was in disbelief. I tried pleading with him, they were not what I would really call pleasure!! He took me into the bathroom and had me sit my sore ass with beads in it into the shower with my legs up and out of the tub. (heavy sigh) Sir pissed all over me………and got it on my face. I wasn’t really sure what to think, I kept wondering if he was actually pissing on me or pouring it out of a bottle onto me. He later told me it was both. It felt humiliating, and tasted gross lol.

After this, he turned on the cold shower water rinsed me off and took the anal beads out. I had actually somewhat grown accustom to them being inside me, I had forgotten they were there. He let me clean off with soap afterwards. I was freezing, but happy to be cleaned off. Sir dried me off, put a robe on me and allowed me to put on a more comfortable blindfold. Sir spent some time kissing me again which relaxed me and I felt good and clean. I was incorrect in thinking that we were going to relax by laying down at this point, haha instead he handcuffed me in a doorway I think. He kissed me and rubbed me a little before telling me he was going to shower and then nap. I was like thinking, he cant be serious!! He DID take the shower, and I was pretty drained and sleepy at this point waiting for him to get out. I was really hoping he wouldn’t leave me there while he slept. He scared me when he got out of shower and approached me because my sense of direction was so lost and I didn’t hear him come up to me lol.

He took me to the bed and let me get under the covers, but I still had the hand cuffs on. We chatted for a bit. Rubbed each other a little. Kissed. He let me try to take the cuffs off, which I was able to squeeze a hand out, but one was stuck. Eventually he took it off. At this point I was actually feeling kind of awkward because I wanted to please Sir. I wanted to sexually arouse him and I am not one to initiate. I wasn’t sure what to do lol. Did he want anything more from me? I didn’t know how to go about it. So I just went for it and grabbed him. He didn’t object, so then I finally re-positioned myself and tasted him. Sucked him. He fingered me, mmmmm which was awesome and I was getting very turned on feeling Sir hard in my mouth. After he came, I was happy.

I also knew he would be wide awake now for a while lol. He makes me laugh at how wide awake cumming makes him. At one point when he started to touch my pussy, I closed my legs and he told me I'm not allowed to say no, this turned me on A LOT as well.

He played around with me and my pussy, talking to me like he was my Daddy, which he knows is a fantasy thing for me. So this lead to extreme arousal and orgasm. This does not happen easily for me at all. I loved it. I told him thank you, which I thought was the appropriate thing to do, but learned that it is in fact, not. He said that saying thank you would mean that he was obligated to give me an orgasm, or that he had to, or didn’t want to but that he did anyways. Apparently that was not the case.

We went to the kitchen and he teased me that another punishment was coming, but instead it was a refreshing piece of fruitJ He then told me it was like 6am or something hahahaaa. I was like, Gee I’m getting kicked outta here real soon. We went back to the bed and talked, which was really nice because it was how I am used to going to sleep at night anyways, hearing his voice.

I was happy that when Sir woke me up that it was not as early as I had expected. I was happy also that he said he slept. I wanted him to be comfortable enough to sleep. I didn’t want to kiss Sir with my morning breath lol, but I knew he was disappointed I wouldn’t, so I did. I had to use the bathroom so bad, so he took me and watched me go, which was interesting lol because I am so used to watching myself pee and when I wipe I make sure I am clean. So I was unable to do this with the blindfold on. Also because I had to take a crap and refused to do it at Sir’s house lmao so I was trying to pee and hold my ass shut. Ha. I also made the mistake of telling him later in the day after I left how I had to go poop, he'll probably try to force me to do it now. Grrrrrr.

He then handcuffed me to a doorway again, and I think he brushed his teeth. Then he came back to me and dressed me, gave me some mouthwash and gathered my stuff. Led me to the door and said goodbye.

I wanted to dive into the pool LOL haha, maybe one day I’ll get to. I got to my car with the help of my sunglasses. Sir called me to remind me to call my sister and mother to let them know I was still living, lol. I like that he cares enough to look out for me like that.

I thoroughly enjoyed myself and really hope Sir did too.

XoxoX, Jae