Megan and Mallory s Birthday Spankings
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Growing up in a small town you know everyone and everyone knows you. I started a summer job at the local diner as a waitress to earn a little extra money between school terms. The local Sheriff, John Stone and my good friend Judge Bob Mahoney eat breakfast every morning at the diner and were pleased to see me serving them. Mrs. Martins that owns the restaurant supplies us girls with a simple uniform dress. The dress fits me real tight around my hips since my measurements are 35-22-37, a fact that does not go unnoticed by the patrons. Mrs. Martin watches as the men are always looking at my ample bottom flexing under the tight dress and I get quite aroused knowing they are. She tells me that Judge Mahoney takes particular interest in my bottom when I walk around the restaurant. We just laugh it off because as she puts it he must be old enough to be my grandfather but even that does not stop me imagining him ravishing me.
My trouble started when one evening my friends called me from the local bar and wanted me to drive them home in their car. I don’t have a drivers licence but I figured it would only be a short trip and no one would be the wiser. Well everything was fine until I was heading back to my apartment and Sheriff John stopped me. I did not realize that I had turned off my head lights so he figured I was up to no good. He stopped the car and pulled out his gun then told me to get out with my hands in the air. When he saw it was me he shouted at me saying, Jennifer what the heck are you doing, I could have shot you. I apologized and told him why I was out, which was fine until he said he needed to see my license so he could fill out a report. When I told him I did not own a license he just shook and rubbed his forehead. He said do you know how much trouble you are in then added that the fines alone will be $3000. I broke down crying telling him there was no way I would ever be able to pay off any fines like that. He put the report book away and said he would talk to the Judge in the morning and see what he can do first. After he escorted me safely home he told me to drop into see the Judge at the end of the next day. I slept poorly that night wondering what trouble I was in.
The next morning Mrs. Martin could see right away that I was distracted and wanted to know what was troubling me. After explaining the predicament I was in she just smiled and said don’t worry dear, the Judge is a fair understanding man, it will all work out. Mrs. Martin did not let on that she knew a lot more about Judge Bob Mahoney than most people in town did and definitely more than I knew. In the meantime Sheriff John Stone was in Judge Mahoney’s chambers explaining what transpired last night with me. The Sheriff pointed out that this could be the opportunity the Judge had been waiting for, a pretty young girl with no way out except what he had to offer. The Judge shook his head and said, there is no way Jennifer would be interested in him and besides he continued I am too old for her; it just would not be fair to her. Sheriff John said to the Judge, don’t you think that is up to Jennifer to decide if she is too young, after all she is the only one who knows what she wants. Back at the Diner, my shift was over and I was nervously getting ready to leave. Mrs. Martin suggested that I wear my waitress uniform when I go over to the court house. Judge Mahoney likes looking at you in that tight dress so maybe it will help your case, you never know. She smiled to herself as she watched me cross the street, my bottom swaying back and forth under my dress. Her mind drifted back to when she was younger and remembered her own encounters with the Judge and knew precisely what was in store for me.
Walking into the Court House the security guard was waiting for me and sent me straight up to the Judge’s chambers where his clerk announces that I had arrived. As I entered his office I saw that Sheriff John was there, both rise to welcome me in and the Sheriff says he will leave to let The Judge and I discuss my options. Well that word “options” sounded like good news since I figured I would be in debt for some time trying to pay off the fine. I was going to sit in the chair in front of his desk but he led me over to the big comfortable couch instead. As I turned I did see his gaze drop down to look at my bottom in my tight dress so I thought Mrs. Martin was right about wearing it. He sat down next to me and handed me the report from Sheriff John Stone, asking me to read it over and verify if it is correct or not. The statement was fairly short and to the point plus it was 100% correct. The Judge asked me to sign it as a formality; he wanted to get the paper work out of the way so we could decide on my punishment. Oh now I didn’t like the sound of that, we went from options to punishment pretty quickly. I stammered a little as I asked him what he meant by punishment. Well Jennifer he started as I see it you have three options. Number one is you pay the hefty fines and you are on your way, but I know you probably can’t afford that. I nodded in agreement with him saying it would take a couple of years to pay it off. Yes he agreed as he mentioned my second option was jail time and was pretty sure that was out of the question. So he continued we arrive at option three, now before I tell you what it is I want you to read the law for yourself so there is no misunderstanding. He handed me the book detailing the law to handle things that have no other recourse. My heart skipped a beat when I read the title of the regulation; in bold letters it said Corporal Punishment for Girls. My lips quivered as I read and saw very descriptive information and pictures of how the punishment would be carried out plus a chart as to the number of strokes and sessions to meet compliance. My eyes began to water as I finished reading it and then looking pleadingly at Judge Mahoney asked if there was any other way. He replied that unfortunately for me there was no other way then added that if I agreed we would begin the next evening after the Court House was closed for the night. He said that would give us the privacy we needed to so no one would interrupt us ensuring my modesty. I could see no other way out so we drafted up the agreement and the schedule for punishment. It would entail twenty five strokes with the punishment strap every night for twenty nights. My hands were shaking as I tried to sign the document and then when done he offered to show me the punishment room. I figured I might as well be prepared but what I saw was a bit of a shock. It was a sound proof room with a large heavy built adjustable whipping bench anchored firmly to the floor and the padded bench had restraining straps at multiple locations. Hanging on the wall were various punishment implements that nearly made me faint when I saw them. The Bench was designed to tip the person forward and raise their bottom up higher than rest of their body plus the legs were position so that when the victim was secured their legs would be spread wide apart. Judge Mahoney took down the strap that he would be using on me; it was a full three feet long and made of a thick heavy composite material, much stiffer and heavier than leather. I told him that I wanted to go home and he agreed knowing that I was overwhelmed with everything. The Judge followed me up the stairs and out to the street, the whole time I knew his eyes were focused on my firm young bottom in my tight dress.
Morning arrived far too soon, all night I kept having dreams of the Judge whipping me and then fucking me, how could I be dreaming of that. As I entered the Diner Mrs. Martin came up to me and asked how it went at the Court House. I immediately burst into tears, I was beside myself as I told her what was going to happen to me but instead of surprise she just hugged me saying I would survive it. She held me tight while she rubbed my back and stroked my hair, I could feel her heart pounding and her breathe quicken and when we parted her face was all flushed. I thought to myself if I didn’t know any better I would bet that she was aroused by my dilemma. Fortunately it was a busy day in the diner because it went by quickly and did not give me time to dwell on this evening. The same could not be said for Judge Mahoney as he sat tormented in his office envisioning the pretty naked young Jennifer tied to his whipping bench while he beats her unmercifully then penetrates her virgin pussy with his one eyed python. It had been a long time since the opportunity surfaced to have a beautiful girl at his mercy. I was cleaning the last table in the Diner when Mrs. Martin came up behind and placing a gentle hand on my bottom whispered seductively into my ear that it was time. Believe it or not it had actually skipped my mind and suddenly the realization came flooding back in. This time I changed into my regular dress that I wear to work since I would not be coming back here tonight. Again Mrs. Martin watched me crossing the street with the setting evening sun shining through my thin dress and her hand impulsively roams under her skirt as she masturbated thinking about my bottom getting thrashed.
My mind is a bit foggy as I enter the Court House but it clears up when I see the Judge waiting for me inside. He takes me by the hand and leads me into his office where he tells me to strip off all my clothes and place them on the desk. He seems agitated and impatient so I think it best to just do as I am told and keep my mouth shut. Once naked he leads me down the back stairs and into the basement, the only sounds are his footsteps on the marble stairs. Nothing is said as we enter the punishment room as he sets about helping me up onto the bench and fastening the restraints. I blush with embarrassment as the cool air and padded bench on my skin makes my nipples harden plus the absolute vulnerable helpless feeling I get as he fastens my legs wide apart. He continues with the restraints until I cannot move at all, then selecting the heavy spanking strap he simply says, are you ready Jennifer. I speak for the first time since arriving and just say, yes Sir. He taps the strap lightly on my defenseless bottom before pulling it back to slash my soft flesh. WHACK, good lord the vibrations go right through me but before I can react, WHACK. The sting now penetrates my flesh and I gasp just as number 3 strikes hard, WHACK. Ooooooh I wail but he pays no attention and applies 3 more hard fast strokes before I can react again. Oh shit I yell out as the burning pain sinks into my flesh. Each stroke just sets fire to my bottom as he whacks me quickly and with purpose, WHACK, WHACK, WHACK. It does not take long for me to loose count but I swear that he gave me more than 25. I am sobbing and crying when he finishes but he takes a minute to survey his art work, enjoying the site of my crimson swollen young bottom and smooth peach of a pussy before releasing me. Upstairs as I finish dressing I turn to him and with a little smile say see you tomorrow? Judge Mahoney finally gives me a big smile and a hug.
I take my time walking back to my apartment, enjoying the cool evening air wafting under my skirt and cooling my steaming hot bottom, I giggle to myself wondering what someone would see if they were looking at me with an infrared scope. In my room I am overcome with intense feelings of arousal. As I get ready for bed I strip naked then inserting my vibrating dildo into my sopping wet pussy I stretch out on the bed. I spread my legs and insert my feet into the foot rail like they are restrained then I use the sash from bath robe to wrap my hands tight to the headboard like they are tied up too. I close my eyes and imagine that my vibrating dildo is Judge Mahoney’s big cock pumping my virgin pussy and he has me tied down so I cannot resist his advances. Only moments pass before intense orgasms flow through my body as I convulse and spasm from the strongest orgasms I have ever had.
Next day at the Diner finds me in a particular cheerful mood and Mrs. Martin points out that I seem to have a glow about me and a sparkle in my eyes. The Judge and Sheriff John come in as usual and both give me a big smile and joyful greeting. The Judge asks me quietly how I am doing this morning and I reply that I am just fine even though as I turn away the Judge notices that my dress fits a little tighter around my bottom, indicating it is still swollen. I do not understand my own feelings but for some inexplicable reason I actually am looking forward to this evening.
That evening the Judge greets me again at the entrance to the Court House, this time I give him a big hug and chat with him as we head to his office. After only one session I already know the routine and immediately remove and fold all my clothing. Judge Mahoney just watches with reserved fascination as I disrobe nonchalantly in front of him and as soon as I am done he directs me downstairs. Judge Bob sees that I am in a cheerful mood so he realizes that he needs to punish me harder. Once Bob has me completely secured he tips the whipping bench forward a little more so he can strike straight down for the maximum effect. He does not ask if I am ready this time but just sets to the task of beating my bare bottom. I didn’t occur to me that my bottom would be extra sensitive tonight but I soon find out after the very first hard stroke. There is a loud SMACK and I squeal out in extreme pain as my extra sensitive bottom takes in the full extent of the stroke. The second SMACK causes me to burst out crying as my mind tries desperately to understand why it hurts so much more tonight. Bob is pleased with Jennifer’s immediate reaction, tipping her farther forward has given him a better angle to beat her harder. He smiles as she wails and cries out from the heavy blows that descend upon her sensitive voluptuous bottom. I am now pleading for him to stop and beg him to let me up but no pleading or begging will deter Bob from giving me the whipping of my young life. The awful meaty sound that the heavy strap makes as it impacts my flesh is gut wrenching. I am unaware when he actually finishes beating me and can’t stop sobbing as he lifts me off the punishment bench and holds me close to him. We stand like this while I sob and weep into his chest and he strokes my hair and caresses my bottom.
Upstairs in his chambers he asked me if I would like him to put some cooling lotion on my bottom. This sounded like a lovely idea so I agreed and he sat down on the big couch and had me lay across his lap. It felt kind of funny as I lay completely naked over his lap as if I was going to get another spanking. However I quickly felt comfortable and secure in this position and relaxed as I felt him begin massaging in the cooling lotion. He was very gentle and caring as his big strong hands kneaded my swollen welted flesh and as I relaxed to his touch I didn’t notice that my legs had parted a little. Judge Bob was very aware that I was presenting a very erotic image to him and his cock hardened under my tummy. I tried not to notice because I didn’t want to embarrass him but the thought made my pussy start to run with my juices. After a while he was rubbing my back with one hand and stroking my bottom and backs of my thighs with the other, it felt so good and comforting that I started purring. Judge Bob was pleased that I was so compliant and even more pleased when he noticed my aroused pussy was leaving a nice wet area on his trousers. After an hour of this luxurious treatment Judge Bob whispered into my ear that I should head for home. He helped me get dressed because I was a little unsteady on my feet then offered to walk me home. As we walked slowly down the road he offered his arm to me which I took and he pulled me in close to him. In my apartment I turned to face him and put my arms around his neck giving him a big hug and a kiss on the cheek then thanked him for seeing me home safely. After he leaves I strip off my clothes and get into bed with my vibrating dildo where again I pretend Judge Mahoney has me tied down helpless and having his way with me.
When I got up on the third day I notice that my bottom was still pretty red as if I had just been spanked. Looking in the mirror makes me wonder if I will be able to do all twenty sessions considering that after only two spankings I was very sore. The work day flies by and before I know it I am in the Judges office again. I express my nervousness to him while I undress and show him how red and sore my bottom already is. He is very understanding as we head downstairs but he explains that there is nothing he can do and must follow the law. After he constrains me to the punishment bench he offers me something to bite on because my bottom will be a lot more sensitive today and it will help me endure it. I agree to it as he places a ball gag into my mouth and fastens it around the back of my head. I am completely vulnerable and defenseless and at his mercy because I cannot even speak to him or beg him to stop. This is exactly how Judge Bob wants Jennifer, she will not be able to protest or protect herself from the onslaught of the punishment strap. He looks down at Jennifer’s bottom that looks like it has just been spanked. Still red and swollen from the previous day means today will be the real test. Bob adjusts his fully erect cock in his trousers as he struggles to control his need to ravish this young beauty and prepares to whip young Jennifer. Bob delights in the sound of the strap beating Jennifer’s bottom plus the muffled cries from her gagged mouth. Bob strikes her as hard as he dares until her bottom is purple then moves down to the backs of her thighs until they match her bottom. Bob is amazed that no matter how much pain he inflicts on this young girl her pussy betrays her as thick slippery nectar leaks from between her pussy lips. He strikes her well past the required 25 lashes and only quits thrashing her when it appears she has collapsed from the pain.
The whipping that Bob just gave me was a blur, I only remember the first couple of burning strokes and then I got faint. I tried to yell but couldn’t, I struggled against my bonds but couldn’t move, I wanted it to stop so bad but just had to lay there and take it. The whipping seemed to go on forever and when it was over and I was untied, Judge Bob had to carry me up the stairs to his chamber. He put me on my side on the couch and covered me with a blanket while I sobbed and wept. He asked if I wanted some lotion again to cool my bottom and with pleading eyes he knew I did, so he lifted me up and set me down over his lap again. Bob got a good look at the whipping he had just administered and wondered if he had gone too far. Such a beautiful fair girl to endure a whipping intended for only hardened criminals seemed harsh but he needed to know if she was the one. I lay over Bob’s lap again feeling that same comfort I felt the day before plus his erection was there again. Over the next few minutes I gradually began to spread my legs wider and wider, hoping he would take that as an invitation. He applied the lotion all over my bottom and thighs and as he touched my inflamed swollen flesh his fingers slipped in between my thighs. He did not quite touch my pussy lips but I pushed my hips back as if I was adjusting my position and his fingers slipped in to touch my clit. He immediately apologized but I sheepishly looked over my shoulder and smiling said he could touch me all he wanted. Bob took a minute then asked if I meant what I said but instead of answering I just spread my legs as wide as I could and reached under me to hold his cock. His fingers teased my clit and my lips before plunging them into my pussy and working me up to my first orgasm of the night. Bob lifted me up so I was standing then he quickly dropped his trousers to release his large cock, he threw me onto the couch on my back and quickly kicking my legs apart plunged his big stiff organ deep into my pussy. He took my tiny hands in one of his big hands and pinned them over my head to hold me down. His thick long stiff member easily slid into me as he began to trust into my dripping wet pussy driving Bob and me to an intense quick orgasm. His cum quickly filled and overflowed my little pussy as it pooled on his leather couch but his cock stayed hard as he kept bringing me to ever stronger orgasms. When I was finally spent he let me up and facing him sat me down on his lap with my legs straddling his hips. We sat like that for some time; I had my face buried in his neck and he held me tight while stroking my bottom waiting until I had recovered from the exertion. Looking up at Bob I pleaded with him that I would not be able to endure any more punishment to which he agreed. He added that he still needed to fulfill my sentence so we decided that I would come to his office every Friday night until all my sessions were complete. Sheepishly I asked about the rest of the weeknights and as I felt his cock hardening under me that answered my question.
My trouble started when one evening my friends called me from the local bar and wanted me to drive them home in their car. I don’t have a drivers licence but I figured it would only be a short trip and no one would be the wiser. Well everything was fine until I was heading back to my apartment and Sheriff John stopped me. I did not realize that I had turned off my head lights so he figured I was up to no good. He stopped the car and pulled out his gun then told me to get out with my hands in the air. When he saw it was me he shouted at me saying, Jennifer what the heck are you doing, I could have shot you. I apologized and told him why I was out, which was fine until he said he needed to see my license so he could fill out a report. When I told him I did not own a license he just shook and rubbed his forehead. He said do you know how much trouble you are in then added that the fines alone will be $3000. I broke down crying telling him there was no way I would ever be able to pay off any fines like that. He put the report book away and said he would talk to the Judge in the morning and see what he can do first. After he escorted me safely home he told me to drop into see the Judge at the end of the next day. I slept poorly that night wondering what trouble I was in.
The next morning Mrs. Martin could see right away that I was distracted and wanted to know what was troubling me. After explaining the predicament I was in she just smiled and said don’t worry dear, the Judge is a fair understanding man, it will all work out. Mrs. Martin did not let on that she knew a lot more about Judge Bob Mahoney than most people in town did and definitely more than I knew. In the meantime Sheriff John Stone was in Judge Mahoney’s chambers explaining what transpired last night with me. The Sheriff pointed out that this could be the opportunity the Judge had been waiting for, a pretty young girl with no way out except what he had to offer. The Judge shook his head and said, there is no way Jennifer would be interested in him and besides he continued I am too old for her; it just would not be fair to her. Sheriff John said to the Judge, don’t you think that is up to Jennifer to decide if she is too young, after all she is the only one who knows what she wants. Back at the Diner, my shift was over and I was nervously getting ready to leave. Mrs. Martin suggested that I wear my waitress uniform when I go over to the court house. Judge Mahoney likes looking at you in that tight dress so maybe it will help your case, you never know. She smiled to herself as she watched me cross the street, my bottom swaying back and forth under my dress. Her mind drifted back to when she was younger and remembered her own encounters with the Judge and knew precisely what was in store for me.
Walking into the Court House the security guard was waiting for me and sent me straight up to the Judge’s chambers where his clerk announces that I had arrived. As I entered his office I saw that Sheriff John was there, both rise to welcome me in and the Sheriff says he will leave to let The Judge and I discuss my options. Well that word “options” sounded like good news since I figured I would be in debt for some time trying to pay off the fine. I was going to sit in the chair in front of his desk but he led me over to the big comfortable couch instead. As I turned I did see his gaze drop down to look at my bottom in my tight dress so I thought Mrs. Martin was right about wearing it. He sat down next to me and handed me the report from Sheriff John Stone, asking me to read it over and verify if it is correct or not. The statement was fairly short and to the point plus it was 100% correct. The Judge asked me to sign it as a formality; he wanted to get the paper work out of the way so we could decide on my punishment. Oh now I didn’t like the sound of that, we went from options to punishment pretty quickly. I stammered a little as I asked him what he meant by punishment. Well Jennifer he started as I see it you have three options. Number one is you pay the hefty fines and you are on your way, but I know you probably can’t afford that. I nodded in agreement with him saying it would take a couple of years to pay it off. Yes he agreed as he mentioned my second option was jail time and was pretty sure that was out of the question. So he continued we arrive at option three, now before I tell you what it is I want you to read the law for yourself so there is no misunderstanding. He handed me the book detailing the law to handle things that have no other recourse. My heart skipped a beat when I read the title of the regulation; in bold letters it said Corporal Punishment for Girls. My lips quivered as I read and saw very descriptive information and pictures of how the punishment would be carried out plus a chart as to the number of strokes and sessions to meet compliance. My eyes began to water as I finished reading it and then looking pleadingly at Judge Mahoney asked if there was any other way. He replied that unfortunately for me there was no other way then added that if I agreed we would begin the next evening after the Court House was closed for the night. He said that would give us the privacy we needed to so no one would interrupt us ensuring my modesty. I could see no other way out so we drafted up the agreement and the schedule for punishment. It would entail twenty five strokes with the punishment strap every night for twenty nights. My hands were shaking as I tried to sign the document and then when done he offered to show me the punishment room. I figured I might as well be prepared but what I saw was a bit of a shock. It was a sound proof room with a large heavy built adjustable whipping bench anchored firmly to the floor and the padded bench had restraining straps at multiple locations. Hanging on the wall were various punishment implements that nearly made me faint when I saw them. The Bench was designed to tip the person forward and raise their bottom up higher than rest of their body plus the legs were position so that when the victim was secured their legs would be spread wide apart. Judge Mahoney took down the strap that he would be using on me; it was a full three feet long and made of a thick heavy composite material, much stiffer and heavier than leather. I told him that I wanted to go home and he agreed knowing that I was overwhelmed with everything. The Judge followed me up the stairs and out to the street, the whole time I knew his eyes were focused on my firm young bottom in my tight dress.
Morning arrived far too soon, all night I kept having dreams of the Judge whipping me and then fucking me, how could I be dreaming of that. As I entered the Diner Mrs. Martin came up to me and asked how it went at the Court House. I immediately burst into tears, I was beside myself as I told her what was going to happen to me but instead of surprise she just hugged me saying I would survive it. She held me tight while she rubbed my back and stroked my hair, I could feel her heart pounding and her breathe quicken and when we parted her face was all flushed. I thought to myself if I didn’t know any better I would bet that she was aroused by my dilemma. Fortunately it was a busy day in the diner because it went by quickly and did not give me time to dwell on this evening. The same could not be said for Judge Mahoney as he sat tormented in his office envisioning the pretty naked young Jennifer tied to his whipping bench while he beats her unmercifully then penetrates her virgin pussy with his one eyed python. It had been a long time since the opportunity surfaced to have a beautiful girl at his mercy. I was cleaning the last table in the Diner when Mrs. Martin came up behind and placing a gentle hand on my bottom whispered seductively into my ear that it was time. Believe it or not it had actually skipped my mind and suddenly the realization came flooding back in. This time I changed into my regular dress that I wear to work since I would not be coming back here tonight. Again Mrs. Martin watched me crossing the street with the setting evening sun shining through my thin dress and her hand impulsively roams under her skirt as she masturbated thinking about my bottom getting thrashed.
My mind is a bit foggy as I enter the Court House but it clears up when I see the Judge waiting for me inside. He takes me by the hand and leads me into his office where he tells me to strip off all my clothes and place them on the desk. He seems agitated and impatient so I think it best to just do as I am told and keep my mouth shut. Once naked he leads me down the back stairs and into the basement, the only sounds are his footsteps on the marble stairs. Nothing is said as we enter the punishment room as he sets about helping me up onto the bench and fastening the restraints. I blush with embarrassment as the cool air and padded bench on my skin makes my nipples harden plus the absolute vulnerable helpless feeling I get as he fastens my legs wide apart. He continues with the restraints until I cannot move at all, then selecting the heavy spanking strap he simply says, are you ready Jennifer. I speak for the first time since arriving and just say, yes Sir. He taps the strap lightly on my defenseless bottom before pulling it back to slash my soft flesh. WHACK, good lord the vibrations go right through me but before I can react, WHACK. The sting now penetrates my flesh and I gasp just as number 3 strikes hard, WHACK. Ooooooh I wail but he pays no attention and applies 3 more hard fast strokes before I can react again. Oh shit I yell out as the burning pain sinks into my flesh. Each stroke just sets fire to my bottom as he whacks me quickly and with purpose, WHACK, WHACK, WHACK. It does not take long for me to loose count but I swear that he gave me more than 25. I am sobbing and crying when he finishes but he takes a minute to survey his art work, enjoying the site of my crimson swollen young bottom and smooth peach of a pussy before releasing me. Upstairs as I finish dressing I turn to him and with a little smile say see you tomorrow? Judge Mahoney finally gives me a big smile and a hug.
I take my time walking back to my apartment, enjoying the cool evening air wafting under my skirt and cooling my steaming hot bottom, I giggle to myself wondering what someone would see if they were looking at me with an infrared scope. In my room I am overcome with intense feelings of arousal. As I get ready for bed I strip naked then inserting my vibrating dildo into my sopping wet pussy I stretch out on the bed. I spread my legs and insert my feet into the foot rail like they are restrained then I use the sash from bath robe to wrap my hands tight to the headboard like they are tied up too. I close my eyes and imagine that my vibrating dildo is Judge Mahoney’s big cock pumping my virgin pussy and he has me tied down so I cannot resist his advances. Only moments pass before intense orgasms flow through my body as I convulse and spasm from the strongest orgasms I have ever had.
Next day at the Diner finds me in a particular cheerful mood and Mrs. Martin points out that I seem to have a glow about me and a sparkle in my eyes. The Judge and Sheriff John come in as usual and both give me a big smile and joyful greeting. The Judge asks me quietly how I am doing this morning and I reply that I am just fine even though as I turn away the Judge notices that my dress fits a little tighter around my bottom, indicating it is still swollen. I do not understand my own feelings but for some inexplicable reason I actually am looking forward to this evening.
That evening the Judge greets me again at the entrance to the Court House, this time I give him a big hug and chat with him as we head to his office. After only one session I already know the routine and immediately remove and fold all my clothing. Judge Mahoney just watches with reserved fascination as I disrobe nonchalantly in front of him and as soon as I am done he directs me downstairs. Judge Bob sees that I am in a cheerful mood so he realizes that he needs to punish me harder. Once Bob has me completely secured he tips the whipping bench forward a little more so he can strike straight down for the maximum effect. He does not ask if I am ready this time but just sets to the task of beating my bare bottom. I didn’t occur to me that my bottom would be extra sensitive tonight but I soon find out after the very first hard stroke. There is a loud SMACK and I squeal out in extreme pain as my extra sensitive bottom takes in the full extent of the stroke. The second SMACK causes me to burst out crying as my mind tries desperately to understand why it hurts so much more tonight. Bob is pleased with Jennifer’s immediate reaction, tipping her farther forward has given him a better angle to beat her harder. He smiles as she wails and cries out from the heavy blows that descend upon her sensitive voluptuous bottom. I am now pleading for him to stop and beg him to let me up but no pleading or begging will deter Bob from giving me the whipping of my young life. The awful meaty sound that the heavy strap makes as it impacts my flesh is gut wrenching. I am unaware when he actually finishes beating me and can’t stop sobbing as he lifts me off the punishment bench and holds me close to him. We stand like this while I sob and weep into his chest and he strokes my hair and caresses my bottom.
Upstairs in his chambers he asked me if I would like him to put some cooling lotion on my bottom. This sounded like a lovely idea so I agreed and he sat down on the big couch and had me lay across his lap. It felt kind of funny as I lay completely naked over his lap as if I was going to get another spanking. However I quickly felt comfortable and secure in this position and relaxed as I felt him begin massaging in the cooling lotion. He was very gentle and caring as his big strong hands kneaded my swollen welted flesh and as I relaxed to his touch I didn’t notice that my legs had parted a little. Judge Bob was very aware that I was presenting a very erotic image to him and his cock hardened under my tummy. I tried not to notice because I didn’t want to embarrass him but the thought made my pussy start to run with my juices. After a while he was rubbing my back with one hand and stroking my bottom and backs of my thighs with the other, it felt so good and comforting that I started purring. Judge Bob was pleased that I was so compliant and even more pleased when he noticed my aroused pussy was leaving a nice wet area on his trousers. After an hour of this luxurious treatment Judge Bob whispered into my ear that I should head for home. He helped me get dressed because I was a little unsteady on my feet then offered to walk me home. As we walked slowly down the road he offered his arm to me which I took and he pulled me in close to him. In my apartment I turned to face him and put my arms around his neck giving him a big hug and a kiss on the cheek then thanked him for seeing me home safely. After he leaves I strip off my clothes and get into bed with my vibrating dildo where again I pretend Judge Mahoney has me tied down helpless and having his way with me.
When I got up on the third day I notice that my bottom was still pretty red as if I had just been spanked. Looking in the mirror makes me wonder if I will be able to do all twenty sessions considering that after only two spankings I was very sore. The work day flies by and before I know it I am in the Judges office again. I express my nervousness to him while I undress and show him how red and sore my bottom already is. He is very understanding as we head downstairs but he explains that there is nothing he can do and must follow the law. After he constrains me to the punishment bench he offers me something to bite on because my bottom will be a lot more sensitive today and it will help me endure it. I agree to it as he places a ball gag into my mouth and fastens it around the back of my head. I am completely vulnerable and defenseless and at his mercy because I cannot even speak to him or beg him to stop. This is exactly how Judge Bob wants Jennifer, she will not be able to protest or protect herself from the onslaught of the punishment strap. He looks down at Jennifer’s bottom that looks like it has just been spanked. Still red and swollen from the previous day means today will be the real test. Bob adjusts his fully erect cock in his trousers as he struggles to control his need to ravish this young beauty and prepares to whip young Jennifer. Bob delights in the sound of the strap beating Jennifer’s bottom plus the muffled cries from her gagged mouth. Bob strikes her as hard as he dares until her bottom is purple then moves down to the backs of her thighs until they match her bottom. Bob is amazed that no matter how much pain he inflicts on this young girl her pussy betrays her as thick slippery nectar leaks from between her pussy lips. He strikes her well past the required 25 lashes and only quits thrashing her when it appears she has collapsed from the pain.
The whipping that Bob just gave me was a blur, I only remember the first couple of burning strokes and then I got faint. I tried to yell but couldn’t, I struggled against my bonds but couldn’t move, I wanted it to stop so bad but just had to lay there and take it. The whipping seemed to go on forever and when it was over and I was untied, Judge Bob had to carry me up the stairs to his chamber. He put me on my side on the couch and covered me with a blanket while I sobbed and wept. He asked if I wanted some lotion again to cool my bottom and with pleading eyes he knew I did, so he lifted me up and set me down over his lap again. Bob got a good look at the whipping he had just administered and wondered if he had gone too far. Such a beautiful fair girl to endure a whipping intended for only hardened criminals seemed harsh but he needed to know if she was the one. I lay over Bob’s lap again feeling that same comfort I felt the day before plus his erection was there again. Over the next few minutes I gradually began to spread my legs wider and wider, hoping he would take that as an invitation. He applied the lotion all over my bottom and thighs and as he touched my inflamed swollen flesh his fingers slipped in between my thighs. He did not quite touch my pussy lips but I pushed my hips back as if I was adjusting my position and his fingers slipped in to touch my clit. He immediately apologized but I sheepishly looked over my shoulder and smiling said he could touch me all he wanted. Bob took a minute then asked if I meant what I said but instead of answering I just spread my legs as wide as I could and reached under me to hold his cock. His fingers teased my clit and my lips before plunging them into my pussy and working me up to my first orgasm of the night. Bob lifted me up so I was standing then he quickly dropped his trousers to release his large cock, he threw me onto the couch on my back and quickly kicking my legs apart plunged his big stiff organ deep into my pussy. He took my tiny hands in one of his big hands and pinned them over my head to hold me down. His thick long stiff member easily slid into me as he began to trust into my dripping wet pussy driving Bob and me to an intense quick orgasm. His cum quickly filled and overflowed my little pussy as it pooled on his leather couch but his cock stayed hard as he kept bringing me to ever stronger orgasms. When I was finally spent he let me up and facing him sat me down on his lap with my legs straddling his hips. We sat like that for some time; I had my face buried in his neck and he held me tight while stroking my bottom waiting until I had recovered from the exertion. Looking up at Bob I pleaded with him that I would not be able to endure any more punishment to which he agreed. He added that he still needed to fulfill my sentence so we decided that I would come to his office every Friday night until all my sessions were complete. Sheepishly I asked about the rest of the weeknights and as I felt his cock hardening under me that answered my question.
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