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An unusual request (the Story Of Jessica Pt 1)

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"Hello?", "Hi are you busy right now?" asked Lauren. I responded that I wasn't and she was more than welcome over. It didn't take more than 10 minutes before she arrived at the door of my place, so she must have been in the area. She quickly moved in to the living room and sat down on the couch. "Would you like something to drink?" asked I. "Nope, just want you!" was her honest answer. Lauren used to come over when she has had a bad date, or when a lover had disappointed her. She is significantly younger than me, but we both fully enjoyed fucking each other. I sat down next to her, and it didn't take many seconds before her eager lips found mine and we were engaged in a deep kiss. She grabbed my hands and placed them over her breasts. I caressed her breasts and could feel her nipples stiffen under my fingers. Her hands were already rubbing outside my pants. We kept kissing and fondling each other for a little while, and then she moved away, removed her top and pants, only wearing her panties she moved down on the floor between my legs. She began to unzip my pants. "Someone must have had a frustrated date." I stated. "Shhh, don't talk about it." responded Lauren as she pulled my pants and underwear to my ankles. She gently licked the length of my cock and kissed the tip before she slowly slid it between her lips. She held it in her mouth for a little while before she slowly began to move her head up and down my shaft. I have to admit that Lauren really knew how to suck cock, she provides that perfect sucking feeling, and knows how to use her tongue to enhance the pleasure. She used one hand on my pelvis to keep herself stable and the other to gently rub my balls. "OHHHHH feels so good sweetie" moaned I. Lauren slowed down a little held me in her mouth and looked up, then slowly slid my shaft inside her mouth again. Lauren sat up, removed all my clothes and pushed me back in the couch. She pulled down her panties straddling my lap. She gently moved her hips using my cock to rub her clit. Her pussy smooth as a peach and she was already slippery wet. She must have had it waxed very recently. I placed my hands on her breasts and just enjoyed the action. I know this was one of those times when she wanted to be in control, and for me to just enjoy the ride. She rotated her hips slightly and slid my cock inside her soaking pussy. I could feel the muscles inside her squeeze the length of my shaft as she slid the full length inside her. She pushed down against my hips and kept me deep inside me, just working the muscles inside her. "Ohhhhh feels so good to have you inside me!" she moaned. I gently rubbed her erect nipples between my fingers, as Lauren slowly began to rock her hips back and forth. "AWWWW fuck me sweetie, ride me, you feel so good!" I gasped. Lauren opened her eyes, looked at me and under heavy breath asked "You like this don't you?" I nodded. "Good because it is mutual. I love fucking my pussy with your dick!" sighed she. She slowly rode me and I could feel how my orgasm was slowly building. "Ohhhh, I am getting close, if you don't want me to come before you, you will need to stop for a second!" said I with a very strained voice. At that moment did Lauren's body start to shake and I could feel her first orgasm rip through her body. "OHHH FUCK! OHHH FUCK! HOLD IT BACK DON'T COME YET!" yelled she as she was coming. I tried to think about cold showers, ice baths and taxes, in a desperate attempt to prevent myself from filling her wet pussy with a load of my cum. Lauren pushed her hips tight against mine and held still. Her chest was heaving as she caught her breath. Moving in very small motions she kept me right on the edge of coming. "Wow, I really needed that!" said she and looked at me. "I guess you like to come." she whispered with a smirk on her face. "Ohhhh yes, I am so close!" whimpered I. "I will hold you here until you give me a promise." was her response. Her minute movement and the squeezing of the muscles inside her pussy drove me crazy. "AHHHHH, what promise?" I wailed. "Mmmmm, you used to be into BDSM." said she with a questioning voice. "Mmmmm." I moaned in response. "Would you play again if the right opportunity arose?" "I think so, what would you want me to do with you?" Lauren stopped, looked seriously at me and said: "It is not me. You know my friend Jessica?" I had met Jessica a several times, she and Lauren were in the same group of people. She was about the same age as Lauren, a little shorter, blonde, with a cute face, "Yes, I know her, OHHHHH" moaned I as Lauren moved slowly up and down my shaft. "Mmmm, well. She is the one that wants to play, but she doesn't know anyone that she would feel safe with." Lauren kept moving and had me right on the edge. "So, I mentioned that you used to play. She likes you, and she knows I feel safe with you and we often have a great time. So I promised her to ask you. Do you promise to call her?" I smiled at Lauren, and said "AHHHHH you for sure have me at a disadvantage, right at the edge, but OHHHHH it does not hurt to call!" moaned I. Lauren smiled and pushed her hips fully down against mine. She leaned forward and kissed me, "You are the best! I should probably force you to call right now" she slowly lifted her hips and then pushed them all the way down again. “But if you called in this situation I doubt you would be able to keep up a sensible conversation!” I knew better than to place my hands on her hips, I nodded and I knew she would bring me over if I simply let her be in control. "AWWWWW I AM CUMING!" moaned I. Lauren slammed her hips against mine again, and I could feel my load shoot deep inside her. "AHHRG, OHHHH YES FILL ME! FILL MY PUSSY WITH YOUR CUM!" screamed Lauren and her body shook from another orgasm. I could feel my cock jerk as it unloaded streams of hot cum inside her. Lauren fell down over me. We were catching our breath, when Lauren said "You better call!" "What? Right now?" "Yes!" answered Lauren and looked up at me. I saw that she was serious and reached for my phone. Lauren slid down and rested her head on my stomach and gave me Jessica's phone number.

"You have reached Jessica." said the voice on the other end. "Hi this is Chris, Lauren's friend, she has asked me to call you." Jessica's voice became a little softer "Yes, thank you for calling." I guess I would have notice her blushing had I been able to see her. "Yes, she told me that you had a desire to explore BDSM." I boldly claimed. "I do, I really do, but I have so far not felt safe around those that want to try, or I have got the feeling they had a stronger desire than knowledge of what to do." "So, what are you interested in?" "I don't know that much, but I know I like to be spanked. Maybe I feeling that I am not in control. I feel like a newbie" she said in a shy voice. "Well, what have you done?" asked I "I have been spanked, but think my partners have been very inexperienced, because it more felt like it was some toying than anything real. I have dabbled in bondage. I have had rough sex, have had all my major orifices penetrated, and I fully enjoy that." "If you thought about things, what things would you put on a never to-do list?" "Not sure... Well, absolutely nothing illegal... probably no other bodily fluids than cum and saliva. I don’t know, this is hard and slightly embarrassing!" "I know. So what things are at the top of your list? What things would you really like to do at a first session?" "Hmmmm, I really like to be spanked. I want to be roughly fucked, told how to please, without any questions or regards about my own pleasure." "Ok, I have some thoughts, I would really like to talk to you more. Usually the best way for this is that you and I negotiate the session. It is not a script of what we will do, but it will set the boundaries. Is that ok with you?" We decided to meet in afternoon the day after, at a neutral place and do the negotiation. Lauren sat up and looked at me as soon as I had hung up. "Thank you, you are the best!" She stated to get dressed. "Ohhh, so this was the whole purpose for your visit!" said I with a smile and a wink in my eye. "Well, true but the fuck was an added enjoyable bonus" said Lauren with a huge smile. I met with Jessica the day after and explained how negotiations worked. That it is not like a script, but an insurance that nothing happened that both were not ready for. We first talked how the session would be set-up, and we quickly agreed that because Jessica wanted to be spanked, the best solution would probably be some kind of student/teacher roleplay. We decided that she would be a student called to her teacher/advisor to discuss her current situation of poor grade. The next thing we discussed was the spanking, she wanted to be spanked by hand, we talked about implements, and agreed that floggers and whips were not right for the scene, she didn't feel ready for crops and switches. We decided that belt and ruler could be used. She explained that she expected to be bruised, but didn't want to bleed. We talked about language, and she was ok with or without dirty talks, she expected to be talked down to as she was failing classes. We agreed that there would be no hitting with fists, and no slapping in the face. She wanted to have her hair pulled and maybe made to suck cock, and manhandled into the right position for being fucked. She said I could fuck her face, pussy and ass. It was all up to me. We talked about many other things, which helped us set the boundaries. We discussed costumes for the play. Jessica said she wanted to wear something like a school uniform, flat shoes, white knee high socks, pleated skirt, white shirt, crossover bowtie and a hairband. She said I could wear anything that would make me feel like if I was a professor. The last thing we talked about was safe-words, what they meant and how to use them. A couple of days later Jessica arrived at my place. I showed her my office, she looked at the desk and the bookcases around the walls and agreed it would be a good place. We talked about the safe-word, making sure she understood it was no shame in using it, and that words like no, stop etc would be interpret as part of the scene. She assured me she understood, and told me reassured me of her safe-word. We agreed that the scene would begin when she entered the office, and would end when both of us had left it. She told me to go in my office and wait for her to change and set-up her reversed safety-call. She smiled and said this was probably the last demand she would do for a little while. I went in the office and closed the door. I could hear her move around outside, making her phone-call, then a soft knock on my door. "Yes!" I said in a firm voice. "Dr. this is Jes. You called for me to discuss my current situation." "Enter!" Jessica came in and stopped right inside the door, her eyes lowered. She looked astonishing in her outfit. Her hair was held in place by a black hairband, the white blouse was a size or two too small so it stretched over her breasts and sheer enough to give a hint of a white bra under. It was buttoned all the way up and she had a cross-over bowtie around her neck. Her pleated skirt ended mid-thigh, her white cotton socks ended right under her knees and she wore black flat loafers. "Close the door and take a seat" said I after I had inspected her. Jessica did what she told. She sat down on the chair at the opposite side of the desk. The chair was far enough from the desk that I could see her knees. She had her hands in her lap, and her knees together, perfectly playing the part of a shy student. "I have called you here to talk to you about your performance in my class!" said I in s stern voice. "Sir, I know I have I have struggled a little, but it can't be that bad can it?" "Bad? Well we can agree it is not stellar, nor would we call it an acceptable performance!" "Sir, I really need you class to stay on the field hockey team." answered Jessica in a soft voice. "Is there nothing I could do to improve my grade?" asked she. "Well, maybe we can solve this with some supplementary instructions here at my office." answered I. Jessica looked up, "Ohhhh would you allow that?" "Yes, of course. I don't want to fail any of you girls." "Ohhhh that would be so great!" answered Jessica with a smile. She stood up and slowly walked around the desk. "I will be a real good girl, and willing student." said she. She keeled next to me and unbuckled my belt, unbuttoned and unzipped my pants. With soft fingers she released my cock from my underwear and lowered her head and kissed the tip. She kept kissing as she stroked the shaft with soft fingers. She opened her mouth and slowly slid the cock inside her mouth. I grabbed her hair and pulled her head back. "What do you think you are doing girl?" asked I looking stern into her eyes. "Showing my gratitude and appreciation, Sir" whimpered Jessica. "Is this what the girls at team and this school have taught you and told you to do? To behave as a slut, that you can get what you want and need through sex favors?" yelled I at her. "I simply thought that this was what you desired, Sir" whimpered she. "What I desired? Is this what you want? Do get want you using sex, like some simple SLUT!" I spitted out the last word. "I am sorry, Sir." "Go over face the corner and think about your actions and situation!" I pulled up and zipped my pants. Jessica did what she was told. I kept watching her, while I pretended to do some work. "So, I guess this is not the first time you done this! As your advisor I have looked through your grades and it seems you have always picked up your grades in classes with male instructors. As a matter of fact, it seems it is a pattern with most of the girls on the field hockey team!" Jessica started to answer. I interrupted her "QUIET! I think I need to teach you a lesson! Pull down your panties to your knees!" Jessica lifted her skirt and grabbed her white cotton panties. She pulled them down and they fell to her ankles. "WOW, you can't even follow a simple instruction. I said pull them down to your knees! PUT THEM AT YOUR KNEES!" Jessica bent over and pulled her panties up to her knees. "It is a disgrace you believe you can go through life getting what you want or need through sexual services! Lift up your skirt and show me your ass!" Jessica quickly reached behind her and pulled her skirt over her buttocks. I looked at her, pretending to type on my computer and looking for something. "Take off your panties and come over here!" Jessica quickly kicked her panties off and let her skirt fall. "DID I TELL YOU TO LET GO OF YOUR SKIRT!" barked I "No, Sir, sorry, Sir" whispered Jessica as she lifted her skirt over her butt again. "I will teach you a lesson girl, I will after that think about what to do with you!" said I. I then added "Get over here and place yourself over my lap." Jessica came over and moved as to sit down in my lap. "NO, little girl, you need to lie down over my knee!" said I with a smile. Jessica lay down in my lap, her skirt was still pulled up and her butt expose. I softly caressed her buttocks, before I raised my hand and firmly slapped her ass. SMACK, I could feel Jessica grasp for air, and she let out a small whimper. Her ass was quickly turning red where my hand had landed. I raised my hand again and Jessica braised herself for the next impact, SMACK! "eeeyouch" whimpered Jessica. "What? Did you say anything?" "No, Sir, nothing, Sir!" said Jessica through her gritted teeth. I rubbed her butt, and gently in between her legs. She parted them slightly and I could feel how wet she was. I lifted my hand a gain, and I hit her ass I quick succession five times. "YAWP" howled Jessica. I massaged her buttocks and I could feel how the blood had flown to her skin. I am pretty sure she could feel my erect cock poking against her belly. "So is that what you want of your life? To be a cheap slut?" asked I. "No, Sir!" did she managed to press out as she tried to catch her breath. "Ohhh, so your actions were just a simple expression of gratitude?" "Yes, Sir!" said Jessica softly "So if I let you work hard for your grades, you would still like to provide me pleasure?" "Yes, Sir!" "Hmmmm, you still need to be punished and taught a lesson for you poor actions and behavior, but maybe I then take advantage of your gratitude. Stand up and lean over the desk!" Jessica quickly rose and did what she was told. She bent at her waist placed her chest on the desk widened her arms and grabbed the far end. I lifted up her skirt and nudged her feet a little to part her legs slightly more. I reached over her and grabbed a 48 inch steel ruler that was on the table next to her. I gently caressed her buttocks with the cold steel, then pulled it back and let it land with a sharp slap over both her buttocks. Jessica grasped for air. "Count loud slut, show me that you at least have the mathematical skill to count!" I barkd. "ONE!", "Well that does not count, I have not hit yet, and you never said sir!" I gave her another quick slap with the ruler, "One, SIR!", "Ohhhh, we have an attitude I see, that one does not count either!" I raised the ruler once more, Jessica pulled in air to brace herself, I held back the hit until she started to let the air out of her lungs. The ruler landed square over both her buttocks. "One, Sir!" counted Jessica, SLAP, "Two, Sir!" I hit her a few more times, and she kept counting. I stopped to softly rub her ass. She was already red from being spanked by my hand, and I could now see welts on her butt. I can feel how wet she is, she is wet far down the inside of her thighs. I raise the ruler again, this time I hit just her right butt-cheek, "Fifteen, Sir!" then I hit her left, "Sixteen, Sir!" I keep alternating between left and right, "Seventeen, Sir! Eighteen, Sir! Nineteen, Sir! Twenty, Sir!" I stop once more and rub her. I let a finger slide up her slit, she is soaking wet. I softly rub the opening to her pussy, she moans, but she stands absolutely still. I tease her opening for a little while and then I walk around to stand in front of her. She lies perfectly still on the desk, her arms are wide apart holding the edge of the desk. I softly caress her hair, she does not look up nor move her chest is still on the desk. "So, this SLUT thinks she knows how to suck cock?" I say in a sarcastic voice. "Others have said I am rather good at it, Sir!" answer she in a soft voice. "Well, I will be the judge of that!" I unbuckle my belt and place it on the desk beside her. I unzip my pants, pull them and my underwear down and free my cock. I grab her hair and bend her head slightly back, and push my erect cock against her face. She parts her lips and I push myself deep inside her mouth. I can feel her tongue move against my shaft, and how she struggle a little to get air. I slowly pull back a little. "Better not get any teeth in there!" Jessica moans a little and covers her lower teeth with her tongue. I slowly begin to fuck her face. I can hear a gawk or two as she chokes slightly on my cock, but I can get deeper and deep for each stroke, and soon she has my full length inside her. "MMMMM, your mouth does feel good, slut!" Jessica moans in appreciation. I have a good grip of her hair and I am now fucking her face rather roughly. "Not sure if I should finish here, or if I should fill you pussy with my cum!" I moan. Jessica's moans tell me she is enjoying the action. "OHHHHH, YES, you are good, maybe I should provide a load in both openings?" Jessica moans louder. I pull out, and Jessica releases a soft whimper of displeasure. I guess she had expected me to come in her mouth. I pull up my pants and grab the belt. I walk behind her. "I plan to spank you some more! I will then fuck you from behind, so you can feel my pelvis bounce against your sore ass with each stroke! Sitting down the next few days will give you a good reminder of this this lesson!" I grab the buckle of my belt and wrap the belt one time around my right hand. I move to the side and aim to land the leather strap over both her buttocks. SMACK, "YOWT!" yells Jessica. I can see her bite her lips. I lean forward and whisper into her ear, "Do you recall your safe-words?" Jessica nods, "Which one to end the session?" she whispers her chosen word, "and which one to make me slow down?" she has now caught her breath and whisper that one back to me. I move away and once more and lift the belt. I let it slap down again, she groans less loud this time. The welts from the impact are forming on her ass. I hit her again, and again, and over and over, the sound of the leather against her skin is sharp, much sharper than both the hand and the ruler. I move her legs a little further apart, I then let the belt hit the inside of her left thigh from below. Jessica screech a little from the stinging pain. I let the belt hit her once more on the inside of her left thigh. I move some and aim against the inside of her right thigh. After the second slap I softly slap up against her pussy. Jessica moans I can hear it is a mixture of both pleasure and pain. I keep slapping her pussy, and her breathing becomes faster and harder. "OHHHHH, please, Sir" moans Jessica. "What? Does the slut like this?" ask I. "Please Sir, I am about to come, please let me come!" I raise the belt and quickly whack her ass from first left and then right, before I come back and slap her pussy again. Jessica screams out the pain from the two whacks over her ass, before she moans again. "Come you slut, you know you can't hold it back. Come and show me what a slut you are!" "AHHHHHHHHHHHHHHH!" Jessica screams without holding anything back, her whole body is shaking from the orgasm that rips her body. Her knees buckle, but she holds on to the desk, with her knuckles whitening. I let go of the belt, pulls down my pants, and while the orgasm is till rippling through her body, I shove my cock deep inside her soaked pussy. "NNNNNG! ARRRRGH! I AM COMING AGAIN!" screams Jessica her voice is now hoarse. I begin to fuck her, my pelvis bangs against her red and welted ass with every stroke. I grab her buttocks and push them apart. I can see my cock slide inside her pussy. Jessica is still shaking below me. I don't know how many times she has come. The shaft of my cock is all slimy from her juices. I can see her rear entrance. I put some saliva on my thumb and push it inside her ass. There is no resistance at all, her muscles are totally relaxed. I pull out of her soaked pussy, and place the head of my cock against her rear opening and press. I slide all the way inside her. "YES, OHHH, YES SIR! FUCK MY ASS! FUCK IT!" moans Jessica. I furiously pump her ass and I can feel my own orgasm build. "OHHHHH, all your openings are fuck-worthy slut! This is not the last time I will fuck you!" I moan "AHHHHHHHH, NNNNNG, OOOOOOH YES SIR YOU NEED TO FUCK ME MORE, DAILY IF YOU SO PREFER!" she groans. I can't hold it back any longer so I push all the way inside her ass and release my load "I'M CUMING SLUT!", "OHHHHH FILL MY ASS, FILL MY ASS!" moans Jessica as I shot long hot streams of cum deep up her ass. I fall over her back, and I can feel her muscles still massaging my cock as the aftershocks of her orgasms rips through her body. I slowly pull out of her ass. I am tempted to have her lick the cum of my cock, but we never talked about ass to mouth in our negotiations, so I instead wipe against her skirt. I pull up my pants and sit down in my chair. Jessica is still lying over the desk. I look at her and say "Ok, I want to see you in my office every Thursday for supplementary instructions! You can leave now!" "I understand, Sir" Jessica stands up, she corrects her outfit, looks around for her panties, "Sir, I can't find my underwear." "Well, leave without them then, can't you see I am busy?" Jessica turns around and walks out the door.

As soon as she has left, I stand up and leave behind her. She is standing outside the door. I gently grab her and lead her to my couch. I wrap a blanket around her, and we both sit down on the couch. I hug her gently. Jessica knows the scene is over and that all is back to normal. I just sit there and hold her, I don’t know for how long, I don’t care about the time, this is her time. I can feel her breathing slow down, and then how her tears start to roll down her cheeks. I softly stroke her hair, and explain that it is normal to crash afterwards. She turns and hugs me, kisses my face, and says "Ohhh no there are no regrets, I don't feel bad at all, I feel stronger than ever. These are tears of joy and happiness!" I hold her and softly wipe her tears, caressing her chin and cheeks. Jessica looks up at me and kisses me. Her breathing is normal, her body feels all relaxed. "Thank you so much." whispers she. I can see how she is blushing, and I get the feeling that she has something more she wants to say, but I will not push her, not now at least. “I am ready to shower.” says Jessica. I take her hand and lead us over to the shower. I slowly undress her. Her ass is already multi-colored, a mix of red, blue and yellow. There are still welts over her buttocks and on the inside of her thighs. I help her soap up and we wash each other. We let the warm water flow over our bodies as we stand in the shower kissing and hugging. We dry each other. "I AM STARVING" moans Jessica, "Do you have anything to eat?" I guided her to the kitchen. As we sit at the table eating cold cuts, cheese and crackers, Jessica asks, "Can I sleep here?" I look at her said "Of course you can, as long as you don't mind that there is a chance that Lauren calls and want to come over!" Jessica smiles and responds, "I don't mind that at all, she has a great tongue, and she taste great as well!”, “Maybe we can both please you?” Jessica adds with a wink.

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