My Online Kink Date Part 5

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My Online Kink Match Part 5

This is an excerpt of a book soon to be published in the Dear Jay D Series by Jay D Strapper (my pen name) Please feel free to critique and comment.

I woke up, with the sun streaming into the windows, in somewhat of a dream state. I felt totally refreshed as I started to wake up. I could feel my ass was terribly sore where I had been punished with the dressage whip but dreamily felt that I had take the punishment well as commented on my him. I felt my bottom gingerly and felt the deep welts on my ass and winced as I touched them. At the same time I felt a little tingle in stomach as I thought of myself being bent over and keeping m hands firmly on the bed as he beat on my ass and thighs. I rubbed my hand across the bottom and wondered at the uneven and rough ridges that the cuts of the whip had made. I thought about the events of the night before going through them one by one. I remembered how humiliating it had been to stand naked in front of my own phone recording my nakedness and then punishment. I had not yet uploaded the pictures and videos to my private gallery on the site and made a mental note to do so as soon as I got out of bed. I reached over and grabbed my phone off my bed table and turned the alarm off marveling that I was actually wakening at least an hour prior to what I usually did on a Sunday morning and enjoyed for a moment the sound of the birds just waking up outside the house. Then I opened up the photo area of my phone and watched the first few minutes of the first video that was taken lying on my back and looking upwards. Since the kids were not up yet, I turned the volume up a bit so I could hear as well as see the video. I watched as I stood there naked at attention and then bending forward over the bed and watching my reaction as the first slice of the whip bit into my ass and then into my thighs. Almost unwillingly my hand crept down between my legs as I watched in fascination my expression of surprise and alarm when the first lows hit me and then heard be count and tell him I was ready for the strike. I was wet, really wet. I turned the video off but my hand remained where it was and I sought some relief as I remembered. I flipped through the still picture as well and saw myself as he had first spread my legs wider and saw that after the whipping I was dripping with wetness to the point you could see a string of wetness dripping down from from slit almost like some spittle. The whipping had turned me on despite me not remembering it that way. He had obviously taken those photos between my legs purposely since he focused in on the wetness. My and stroked a little faster as I looked at it. I saw myself bound up in various stages with my legs spread wide with the bar, my tits bound by the rubber bands and the nipples erect with the bands on them. The next set of photos showed e with my legs bound to my wrists with me ***king out between them as he took the pictures. I could see the bright purple stripes on my thighs and my ass that stood out and my tits that were purple from the enclosing rubber bands. He had taken some close ups of the stars he had placed on the side of each tit and the breasts themselves covered with the horizontal stripes from the switch he had used. Again my hand continued to move me toward orgasm this morning as I looked through the pictures. Finally I saw me wearing the butt plug clearly in my ass and remembered when he had turned it on with a remote control switch the surprise it gave me when it started to vibrate. In that picture I was also wearing the dildo and clitoris stimulator and it looked like it did indeed provide me with some protection as he had switched very near to the sex and asshole. I could clearly see the ecstasy written on my face with al three vibrators on and working against and with each as I remembered he switched between s***ds and intervals for each of them being on and my hand between my legs moved faster and I thrust a finger and then two deep inside of me seeking some relief this morning. I remembered him say that he had personal toys for each of the women he was involved with and the jealousy sprang back in my mind as I remembered how I did not want him to share what we had with others. Of course I realized both then and last night that I had no control of that part of his life and cut off my thinking of it right then. Instead I should feel happy that he thought that much of me that each of those implements were bought especially for me and I wondered how many other subs out there had their own devices label especially for them and kept clean by him personally. My hand moved faster and more intensely. I shook the covers of my top and looked down at my breasts to see how roughly they had been used by him and could see the stars on the sides of the and it intensified my excitement even more. I knew then and made the decision I wanted more of this and more frequently. I resolved to send him an e-mail today because I did not want to wait another 6 days to have another session. I knew that having one sooner meant I would be beaten on a bottom that would not be quite ready for it but that did not stop my resolve. My hand moved even more intently and I brought myself off, not with the explosive intensity of last night's orgasm but satisfying none the less. I was breathing roughly when I was done and spent my time wisely uploading the videos and photos to my private gallery on the site and then checking to see if he had requested access to them. I saw he did and completed the process so he had access. When I returned to a normal state, I rolled out of bed and sat on the side of it, wincing a little where the switches, cane and whip had struck me. I felt the slight discomfort under my breasts where he had so purposely switched me so that when my breasts jiggled at all I would remember him striking me there. As I uploaded the pictures I had noted that he had taken some pictures of me with his cock down my throat and finally the final clean up as well. It should have felt humiliating, and it did, but it also felt very exciting to me that I had been photographed in that way. The last sots I didn't even remember at all and they were direct shots of my face with my eyes rolled back in the sockets and a look of fabulous enjoyment on my face as the waves of my orgasm poured over me. The final shots were of me lying flat on my back with my legs down and spread wide open, looking like I was asleep. My hair was messed up beyond belief and my face looked like I was a clown with makeup smeared by tears running down my face. I looked exhausted but very still and entirely satisfied from what had just happened. I wondered how long I had been out by that time. I still had misgivings about other women being administered to by him though. It just didn't sit well with me. Face it I was jealous of them.

I groaned as I made the attempt to stand up knowing that I would hobble to the bathroom and that the best thing for would be to get into a hot shower. Obviously the best I could do in getting to bed last night was to just drop my clothes on the floor and sleep naked. When I got into the bathroom I could not help but examine myself all over. I have double mirrors on each side of the bathroom so it was easy to look at the damage to my body on the backside. I lifted each breast and saw the thin stripes on each one both over and under the nipples and saw that he had done a good job in getting into the crevice of where boob meets the rest of my body. Those stripes would hurt for a long time I figured. The stars were filled with the dark purple from the snapping of the rubber bands to fill them in and very accurately done. Obviously he had learned to color between the lines and the stars would last several days. I looked between my legs and saw that while the stripes from the switch between my legs and around my sex were hurting they were thin and would not last too long. On my ass you could still see the yellowish green tint from the previous beating covered with the welts from the whip, cane and switch over it. The whip marks were a hideous very dark purple by this time and cut deep into my ass. I made a note to avoid all punishment in the future from the dressage whip. I vowed that I would never be late or talk back again. That was a lesson best learned. The three star rating he gave me with the rubber bands stood out above my ass and I found myself wishing I had somehow earned another to add to the line of them. All in all though, it had been a lighter night than the previous session and I reveled in that and it strengthened my desire to have a session sooner rather than later. I was smiling after the examination...... and wet between the legs again when I stepped into the shower. I used the shower as an excuse to give myself another somewhat substandard orgasm when compared to the ones I had experienced the night before. As I did I wondered if he realized that I had cheated the night before and had cum a couple of times prior to his permission but had hid it. I felt like I had a secret. I smiled again as I toweled off and got ready to meet a new Sunday.

I was up early enough that I decided to make a big breakfast for the kids and as they came in they were astounded that I had made both pancakes and eggs for them that morning. One even commented that I looked particularly happy. I agreed that I was. I sent them off to get dressed for Church as I cleaned up, started the laundry, drank my coffee and steeled myself for my Sunday ordeal. I did not forget to write the e-mail to hi requesting a new session after I checked the schedule. Again I had three options. Tuesday at 6PM, Thursday at 6PM or Saturday at 5PM. I told him I wanted to see him more than just once a week. While I was dressing for church, he came back and said that would be fine although he thought it might be better to wait but if that is what I wanted he was free for the Tuesday night meeting. Accordingly, to take it easier on me, he said the price would be role play for that night and he would reserve the rougher session for Saturday if that was ok. I went directly back to him while I was still dressing saying I agreed.

I wriggled around on the hard pews of the church where he had hit me with the whip in particular but it was a good suffering as it brought back memories. We left directly from Church to my Mother's house for the family afternoon dinner. Thank goodness we did not have any games that afternoon which is a direct bonus of living in a small religious midwestern town. This week, as last, I found myself better prepared to deal with family drama which was a weekly item. I felt somehow superior to the others ad refused to rise to the bait when remarks were made that I usually would have taken umbrage from. For some reason all seemed right with the world and I enjoyed the day relaxing and watching the game on TV and playing board games with the family. I felt so good that I stopped on the way home to get ice cream for everyone and then allowed video games and computer time as well when we got home. I checked my e-mail and found that he had sent me instructions. The email gave me the name of a new hotel some few miles further that the one we had used which was doable for me and informed that I should expect a package from Amazon. I was to wear the contents of the package to the session. He would send me the room number an hour before the session and reminded me not to be late again as if I needed any more reminders than what I had gotten last night. I spent my remaining time happily doing the household chores including laundry where I day dreamed about what the next session might entail while I folded clothes. Sunday night I relaxed for what seemed like the first time in a very long time. I watched TV which I rarely have time for and went to bed a little early after examining myself one more time and determining that I had made the right decision.

Monday dawned early for me. Even before I had downed my first cup of coffee I heard a delivery being made at the front door. I did not have time to examine the package so I put it into the bedroom so the kids would not even think about opening it, hiding it in my closet. Then it was out the door as the kids raced for the bus and the oldest off in his car. I drove carefully to work and was content. The day passed slowly but I was for once not in a mood about the small amounts of gossip around the office, the interruptions and shallow back biting. I felt above it all. I had lunch with Barb that day and she made me tell her all about the night before. Again I had to show he my war wounds and she was more than intrigued. I could tell she was living somewhat through my experiences. While we chatted she casually asked if it would be possible for her to me him. That took me back. I had never considered that previously and shook my head vigorously no. She got a little whiney when I told her that I did not want to get into that but she insisted I bring it up with him if I got the chance. In my own mind I decided that would never happen but told he if the chance occurred then I would bring it up. Those comments really disturbed me for some reason and then I began to think my jealousy might be the cause. Perhaps but I decided it was simply because I did not want her to screw up my thing. She had always been vivacious and, I thought, prettier. She was a wild one and I knew I given a chance she would try to steal hi away from me in a heartbeat. I put it off the table but did not tell her that. Instead I concentrated on telling he that he was a very private man and quite contented with me but I would bring it up. That at least satisfied her for the time being.

When the day was done, I had lots do but the first thing I did when I got home was open that package from Amazon in the privacy of my room. The kids knew enough not to bother me there. The package had been marked as a gift and had a note in it from him which you can do on Amazon. The note simply said: “I hope you enjoy dress up. Send me an email when you get this and I will give you instructions on our roles.” Inside the box was a costume which consisted of a plaid skirt that looked to be knee length on me, a pair of knee high socks, a white blouse, and a necktie of the same plaid as the skirt. The collar on the blouse was frilly but the rest was sheer cotton. Also in the box was a white bra in my size, a three pack of white “Granny” panties and a pair of saddle shoes in my size. I quickly sent him an e-mail saying I had received the box. Within a few minutes he sent me back and email I wondered how come he always seemed to be able to respond so quickly to my notes, chats and questions. I also wondered about him being able to afford all of the implements, and stuff he was using as well as paying for hotel rooms for us to play in. My wealth consisted of a bank account that had to be managed very carefully with not a lot of room for error.

The e-mail read: “Your role is a 24 year old woman who is reliant of her godfather as his ward. He spends lavishly on you and is the trustee of large inheritance your parent left you when they were tragically killed in an automobile accident when you were young. He sent you to expensive boarding schools until you were of age and is now paying for your college degree at an expensive, very traditional and strict private college. It is your senior year in college and you have allowed your ***rs to influence you in bad ways resulting your grades to drop to the point you are being faced with expulsion. He had just been informed by the chancellor that you must bring your grades up to standards and though he loves you, he will do as he must. I am your godfather. You have always lived somewhat apart and he has never done anything inappropriate towards you. Now you must face him with your behavior and your subsequent grades. The trust will not pass to you until you are thirty five and has a codicil you are aware of that if you do not graduate you will not inherit but rather the *** will be donated to a foundation set up I your parents names. You can expect your godfather to be very angry and disappointed with you and will do anything to ensure you graduate from college. Your job is to what you can to assure him of your very true intent to graduate. Wear your school outfit to your meeting with him. Do not bother to bring any other clothes since you will not need them. You will not adhere to our other rules when you get there except to move directly to your spot and wait for your godfather to start the role play. Bring your phone so it can be recorded and uploaded. Be sure you are on time and in the right mood for playing the game. I will provide you the room number on hour before you are to arrive. Make sure your uniform fits. Remember you have been and are a bad girl and easily influenced by your friends.”

Good Lord. At least this seemed to be an easy assignment. I did go to community college so I have some experience from that aspect. I was not a good scholar in high school but I worked hard. I have had lots of fantasies however and am a good actor I believe. How hard could it be.

I put the uniform on in the bathroom and it fit like a glove. His getting my measurements must have helped a lot. I am pretty chesty and dressing emphasized that. I must admit I looked very cute in that school uniform. I was ready to go. Now the question was how would I get in and out of the house in that uniform. I decided I would park the car in the garage, lock the garage door from the house, change into and out of it in the garage leaving clothes to get into when I got back. I would take some doing but there is was. I had a plan. I decided pizza for dinner and give it to the kids just before I left for the session. Who knew I would have to do this kind of planing.

Barb and I hd lunch again together the next day and I told her about the role play and she was really excited. She asked me if I had asked him about her after she pumped me for all the information she could. I replied the topic never came up and best done in person just to put her off. Barb is pretty pushy as well as being wild so it was not easy to get he off that subject. Instead I described the uniform for her in detail She wondered if he had a fetish for “Granny” panties. I just shook my head if disbelief and told I had to run to get back to work. I also promised her to dish at the next lunch date on Thursday. Wednesday I had a lunch meeting so she would just have to wait an extra day.

I scurried home picking up pizza on the way. I I put it in the oven and changed into my jeans and t-shirt and prepped my costume in the garage. When I called the kids for pizza I reminded them I would be gone until about 10 o'clock and locked the door to the garage behind me as I left. I hurried to make the change, unlocked the garage door to the house and left with my jeans and t-shirt left behind. Only then did I realize that I would have to wear the costume through a lobbyI had never been in to get to the room. I wondered if I could get in a back door or not. I headed straight for the hotel with no time to spare according to Google maps and pulled into the parking lot with just a few minutes to spare. I didn't see any other way to get in and I had to go to the fourth floor of the hotel to room 432. I wondered as I entered the lobby if he had done this on purpose just o humiliate me a little. I guess it wasn't that bad. There was nothing all that naughty about the clothes, just a little embarrassing for grown woman in her forties wearing them. The desk clerk eyed me suspiciously as I walked by her as confidently as I could. I passed two other customers, the hotel bar and restaurant in order to get to the elevator, pressed the button and hoped the lift would be fast. When I got to the fourth floor I saw I had less than a minute to go and ran down the long hallway hoping I would not run into any others as I did to reach the door. Again I tentatively knocked on the door.