9 comments/ 19610 views/ 2 favorites Earning My "A" By: NotHisLady Earning My "A" "You know I love you. I want to thrill you, but if you truly mean stop then I stop." That had to be said too, even though he knew it. "Do your worst then, I trust you." That made me smile. The little timer was on the night table, already set. I showed him the numbers as I started it and he laughed out loud. I had set it for 4 hours. "I think I'll do my best instead." I leaned down and kissed him. "Now tell me how I look." It was part of the game but he meant it when he said I was beautiful. It should have made me go all gooey inside but instead it only made me bolder. "No, the ribbon is too much." I touched the velvet at my throat. "You should untie it for me." Bending low, I put him within a breath of my throat while my hair brushed his skin. I offered him the tail of the bow. I felt him take it in his teeth and pulled back, letting it unravel and release. "Well now I suppose I have to find some other use for it, don't I?" I did the binding slowly, partly so I wouldn't make a mistake and partly so that he would have a chance to appreciate what I was up to (or let me know if it were too tight.) Over and under, around and up, cinching and dividing and finally a long row of knots likes rings. All of it ending in two long tails. I made a careful knot in the end of one. Pull on that one and it would all be undone, pull on the other and it all got tighter. Mixing them up wouldn't do. Now he was growing more fully erect and the binding was pulling snug. "Yes, you could say that someone has been planning," I whispered in his ear, and then gave it a lick for good measure. Sitting back, I opened my black velvet box. "I even have a little treasure chest." I wish I could describe the expression on his face. He trusted me, knew that causing him pain was one thing I would not do. Suddenly he seemed to be wondering about the things I would do. This I'd considered for a while even tried it on myself to be sure. A little should be enough and I knew just how I wanted to use it. The little jar of lip balm came out. This one was peppermint—not just flavored but with real peppermint oil in the base. I put a good amount on my lips then carefully kissed his nipple, letting the balm rub in all around but not in the most sensitive place. The result wasn't immediate. It took a moment for the tingle to start, having me blow gently on his skin brought the intensity even higher. I anointed my lips again and repeated my actions on the other side. Now he was shifting beneath me again, wiggling around even though I held him tight with my knees. I let the cold slick material of my boots rest against his thighs. I settled back just enough to let the tip of him touch the wetness and heat he wanted, lingered then moved away. I glanced into my velvet box and then back at him. "Calling a halt so soon?" He had to bite his lip to tell me "no." "Oh surely you have more to say than that," I knew speaking wouldn't come easily so of course I asked him to do it. "If you want me to continue then just ask me to go on." Somehow getting the words "please continue, darling" out of him every few steps was the most fun of all. I would stop the most delightful things, just so he could tell me to go on. He was right about one thing—I did enjoy it even if I'll never tell him that. I took him to the edge but never over it until he was slick with slowly dripping fluid. Up and down the scale we went as my finger found that spot inside and my tongue kept working. Always stopping too soon. Once I backed away for almost a full minute, waiting for my invitation to continue, making him watch me use my fingers to please myself. I even told him that I was doing it because he wouldn't, let him say, "Please may I." I knelt at the head of the bed and told him if he could roll over and get to his knees then he could. He could. I'd never gotten much joy from a man's mouth but this was different. This made me dizzy, shattered me until I almost lost control, but in the end I pushed him back. He moved to roll back over but I told him no. I even gave him a little swat on the ass, lightly but it startled him. It startled me too, I'd never thought of doing such a thing. I stood behind him, reaching into that black velvet box and I could see him remembering all the times he's teased me about strap-ons. It was a thought I let him ponder for a while. I watched him getting ready to tell me no, struggling with himself over whether to say it, I know I was smiling. Of course I didn't have any such thing. I did have something but not that. The little thing was barely as big as my finger. The difference being that it vibrated at the tip. I stopped with my hand in the box and waited—he knows me too well. He couldn't have truly believed what he was thinking. In the end I had another "please continue, darling." It made me want to kiss him. I reached for the knotted end of the ribbon and gave it a tug, pulling it all away as it went slack. What I wanted next wasn't in that pretty black box. I stepped back a little and slipped out of the beaded thong. The metal was warm and slick and I wrapped it loosely around his cock, using my hand to slide it slowly up and down. Finally my little toy came out of the box and began to hum. Touching him with it, watching him pull the littlest bit away from the tip I was tempted to show it to him. I didn't. Instead I kept teasing with the tip, just enough that he couldn't know what was there. I kept stroking slowly with that string of silver beads. Before it could go on long enough to satisfy, my hand stopped moving and merely gripped him tight. That's when my little toy slipped in, probing slowly as I held my grip on him firm. For a second I thought I'd taken him past the edge, but no. I held him tight, my hand not moving even as I could see him trembling. When my hand moved again it was to slide down and away. My little toy was withdrawn and he was left with only my presence behind him until I had him on his back again. Until I was kneeling over him again, letting him brush against me. He was so hard, so hot and hungry. I gripped him, lowered my body so close and moved that full throbbing cock over my wetness. Rubbing it against my swollen clit and quickly in and out, I used him the way I would a toy until my orgasm rocked us both. "Do you want me now?" I tried to sound as calm as possible but I was done. I wanted to finish it together. I wanted him. "Tell me, do you?" "Oh yes." Those same words had begun it. Holding him in my hand, guiding him and holding him back, I let just the tip in and held him there. Then I impaled my body on his. I didn't start to move right away, just held still and felt it, being full of him. When I did move I did it slowly—intentionally slowly enough to frustrate him. My last act as "mistress" was to reach up and untie the scarf on the bed. "Well if you want me, then have me." I breathed it into his ear while he was slipping the loops off his wrists. He grabbed me hard, pushed me up and around until I was on my knees before him and thrust hard. I was still in my corset so my breath came in short gasps. He held nothing back. I braced myself, pushed up against him and took everything he had. He came so hard I felt the throb of it, cried out with him. We almost made 4 hours, but not quite. Much later, cradled in his arms, I kissed him and asked, "So, what do you want to do today?" What didn't we do? We went for ice cream we held hands and talked. We retreated to our bed to make love—he tormented me as mercilessly as I had him and I loved it. We slept in each other's arms and he woke me with kisses. He helped me pack my things. He kept the black velvet ribbon. Then he took me back to that Delta terminal and we said good-bye the same way we'd said hello—with a long sweet kiss. I tried not to let him see my tears; he tried not to let me see his own pain. There was no reason for it we assured one another. There was no reason for sorrow because we had each other. Only time would separate us and we would not let that be for too long. Now I have memories and I have hope. I wish I had more of both but I can nurture what I have. Glancing at the slender gold band on my finger, I thought of being home again. At least I've stopped crying. Earning My Collar My mistress and I have been through a lot together, but now we I feel we are closer than ever before. Tonight, I have earned my collar: a symbol of our relationship with one another. It is secured around my neck and only she holds the key. I am hers now, I have willingly given myself to her and she has accepted me as her own. The collar sat on the dresser for weeks as I trained for this day. Open and empty, I would see it every day when I woke up. We picked it out together, it was perfect for me. I wanted something discrete, but still something that would still symbolize our relationship and my submission to her. I knew what I had to overcome to earn her locking that lovely device around my neck, and although the procedure of earning it was a bit intimidating, I knew that I must accomplish it. I knew I had to be hers. On a day that she had work, I got up earlier than usual to complete all my tasks for the day. I did my lessons, exercised, groomed myself, did my chores around the house, prepared dinner for us, and awaited her arrival eagerly. When she got home we had a relatively normal night; we enjoyed one another's company as she winded down from a stressful day at work. She was unsuspecting of my plans to receive my collar on this night. When I finished washing the dishes she was laying on the couch reading a book. We made eye contact and shared a smile; we were both pleased with each other. But little did she know of the gift I was about to give to her. She continued to read her book as I walked off to receive the implements necessary for me to earn my collar: a belt, a paddle, and a cane. When I returned, I placed them on the couch next to her and stood before her silently. She saw me in the corner of her eye and placed the book down, looking me in the eye. "What is this, Alex? You want to receive more training?" She asked calmly, directing her attention towards me. "N-no, mistress. Tonight I wish to earn my collar Miss Magen," I said as I began to undress myself, "Please make me yours. I want to be owned by you mistress." After I was completely undressed, I kneeled down by her, resting my stomach on the seat of the couch with my ass exposed to her. I knew she was about to put me through hell to earn that collar, but I accepted it as what I needed more than anything. "Mistress, I am ready. I will not disappoint you. Tonight I will prove to you that I am willing to go through a tremendous amount of pain to show you how much I love and appreciate you." With that, she smiled at me at my willingness to try. Honestly I feel she probably doubted my ability to last through the whole ceremony without asking to stop. She stood up, grabbed onto the belt, and begin to rub my ass with her hand. "Don't be afraid," I thought to myself as I closed my eyes in preparation, "My mistress loves me, this will be intense but it will not kill me. I want this. I need this." I focused on holding myself together, to surrender to her completely. She began to warm my ass up with the belt, lashing me with mild velocity. She didn't want to break me, but she wanted this to be a very intense experience. After about 10 lashes she began to pick up speed, whipping my ass and upper thighs with the leather belt. It stung a lot, but it was tolerable. I felt the blood rushing to my ass as it began to blush in response to her licks. She didn't back down, my ass got no breaks as she continued to smack the strap against my vulnerable back side. I was almost in tears from the pain, but I was not about to give up. She then stopped momentarily, and I felt the smooth, cold paddle against my ass. She rubbed it softly against me in preparation for the next step. Then, SMACK! The paddle hit my ass with almost full force. I grabbed onto the back of the couch as I felt the first tear escape my eye. I closed my eyes tightly and began to think of my mistress and my love for her. I had to hold on. The next few blows were damn near crippling. The intensity was high, and I couldn't stop the tears. I stayed focused on her. I couldn't give up. I must get through this. Everytime the paddle struck me I felt myself wanting to ask her to stop, but I did not. I let my guard down at that point, my heart was racing and I was breathing heavily to cope with the pain she was inflicting on me. I had to give up control completely. I had to let her finish and not interject. I had to prove to the both of us that I am her property now, I couldn't allow myself to ask her to stop. By the time she was done with the paddle I had lost track of time, I was lost in my submission. I hope she was counting each blow because I certainly lost count. The pain was so great in measure. And yet I wasn't even half way through. I felt her hands on my poor, swollen, welted ass. She comforted me briefly before going back to the belt. "Alex, you can do this. You're such a good boy. You're doing such a good job." She reassured me that I could earn my collar. Those words echoed in my head for at least five minutes. She began using the belt on me once again, making sure every inch of my ass was thoroughly worked into submission. I bit down on the seat of the couch, tears rolling down my cheeks. This was very, very hard for me. I had to redirect my thoughts to how much I needed her, and how much she has helped me. I looked back to when we first started talking, I thought about everything we had been through together and the progress that has been made. "Have you been keeping count, Alex?" My mistress asked me. At that point I was scared to answer, I had lost count. "N-no mistress, I lost count awhile ago. D-does this mean we must start over again?" I sobbed. "One fifty Alex. You are almost there." She said as she tapped her cane against my ass. CRACK! It stung so much, I tensed up and went back to focusing on not giving up. I was shaking uncontrollably at this point. I didn't know what to do, but I knew I was almost there. The collar was within my grasp. I had to hold on, I had to give up control over my body entirely. I scrambled to disconnect all the thoughts involved in making me want to resist her blows. I laid there, taking them willingly. CRACK! CRACK! Almost there... I can do this. It will end soon and I will receive my reward. I will earn her love. I will serve... I can't leave. I can't let myself. I must let her finish. CRACK! Tears continued to roll down my face. Something was different though, I was more accepting of the pain. And then, it stopped... I felt her lubing up my ass as she prepared to fuck me and reward me for getting through it. My ass burned so much, but I felt amazing. Had I done it? After worrying about this for months, had I really just earned my collar? "Alex, I can't explain how happy I am with you right now. You did it. You have given yourself to me, you have given me the greatest gift possible of giving." She said as she reached down and placed the collar around my neck. She locked it into place and kissed me on the back. "You are mine now Alex." She pushed the strapon inside of me and began to fuck me. I felt so happy to have completed this task. I didn't have any words for her at this moment, but she could tell how happy I was to have accomplished this. I let out a small laugh, still breathing heavily and my heart pounding in my chest. She continued to fuck me and reached her hand down below my waist and wrapped it around my cock. We continued to fuck for awhile before she finally let me cum. She then dragged me off to bed with her and held me closely all night. The pain I continued to feel was a mere reminder of what I was willing to put myself through for her. I placed my hand on the lock of the collar and drifted off into the best sleep of my life... Earning My Keep As I kneeled on the thick lush carpet, naked and aroused, I could not believe that here I was again, with the cock of another man firmly making its way down my throat. This was my second afternoon to spend with Rob, my benefactor and new friend. I looked up at him as I engulfed his eight inch cock with my warm and wet mouth. Rob just smiled a very cocky and smirky smile as he threw his head back and enjoyed the blowjob. With his hand firmly holding the back of my head, he began to mouthfuck me and pump his cock into my stretched mouth and throat. As he violated my wet mouth, I thought back to how this had all began so recently. It had been six months since I had moved into my own apartment in the city. Prior to that, I had always lived with my parents. After attempting to live on my own, I realized that I just couldn't afford it. But moving home was not an option. I was enjoying the college I was attending and just could not bring myself to drop out. After looking around for work, I began to think about finding easier ways to earn my keep other than waiting tables and working in department stores. I checked out an online site for wealthy sugar daddies. After several dry runs, I came across Rob. Rob lived just across town in an affluent neighborhood and was newly divorced and looking for a sugarbaby to spoil. I was barely 19, baby smooth, hung and athletic. I figured I was as attractive to someone like Rob as anyone else would be. After several back and forth e-mails, we met for a date and had dinner at an upscale restaurant downtown. After much discussion and a great deal of wine, we decided to head back to his place and get naked and just see the other's reaction. We wanted to make sure there was some chemistry. Rob was approximately 40 at the time and was in great shape. He was not a hairy guy but was very muscular and built sturdily. He was about 6'1" and 185 pounds with a better than average cock that hung down about eight inches when fully erect. When we got to his very stylish house, we stripped and sat on the couch and began watching a porn movie to see what kind of reaction each would get. The movie was appropriate for the moment. It was about a young man getting fucked by his older neighbor. The age difference was about the same and mine and Rob's and the tone was set. I began to get hard and noticed that Rob was stroking himself very slowly and very deliberately. He watched me and smiled. After a few minutes, he reached over and took my cock in his hand. After stroknig it for a little while, he bend over at the waist and began to lick my fully erect cock. In just a few minutes, Rob was kneeling between my legs and sucking my cock wildly and feverishly licking and sucking my balls. I moaned and groaned and talked dirty to him which only drove him on. After a little while, I felt him to pull off and opened my eyes and saw him standing before me. He was holding his cock and pushing it into my face. I can only say my first blowjob was an experience. Now I was giving my second in as many days. I licked up and down Rob's shaft and slurped on his head with a hungry and wet mouth. I massaged Rob's prostate while I sucked. He gagged me several times and I could tell he liked his blowjobs wet, sloppy and noisy. I did my best to please. Between groans and moans, Rob talked to me. "Eat that meat, baby!" "Suck that cock for Daddy, my little cumslut." It was turning him on to hear me moan and groan and whimper between his legs. After about thirty minutes of the sloppy blowjob, I felt Rob's grip tighten. He held my mouth on his cock until he shot a warm thick stream of cum into my throat. I couldn't contain it all and let a great deal of it spill out of my mouth and onto my chest. After a little play, I had Rob as hard as ever. I led him into the bedroom and I drew him onto the king sized bed. I stroked his wet slippery cock to keep it hard. I had been preparing myself for this moment with the help of a tube of KY and a nice comparable dlido. I lay on my back and pulled Rob and his hard slippery cock into my boi pussy. I gasped at the enormity of his meat as it first pushed its way past my sphincter. Once Rob was fully inside me, the experience of pain was replaced with pleasure. I wrapped my legs around Rob's rock hard torso and kept pulling him deeper and deeper. He plunged into and out of me for a good half hour. Then he turned me onto my belly and pushed me facedown into the sheets and pillows. Again, he plowed my ass but the feeling was one of exhileration. After a little doggie style and several minutes of me riding him "cowgirl," he again mounted me and rode me missionary. Finally, he rolled his eyes and began to curse and I knew he was close. He pulled out in time to shoot his load across my stomach and chest. I joined him in the shower for what I thought would be a quick shower, but it seemed my new partner was easily aroused and could fuck several times in an afternoon. Soon I found myself between his legs again, this time kneeling on the wet shower stall, sucking his wet soapy cock. Afterwards, Rob turned his head away from the shower head and lay on the floor of the stall and I road his cock until he shot his cum into my ass. We dried each other off and Rob decided it was time suck my cock. He should have known it wouldn't take long and it didn't. I shot it directly into his mouth which he seemed to enjoy as he swallowed every drop and sucked me until I began to go down. We lounged around that afternoon and took a dip in his backyard in-ground swimming pool, but I didn't leave until my lover has fucked my ass another two times. Rob took care of and my needs and I think I did the same for him. I never knew why his wife divorced him. Surely it wasn't the quality of the sex. He was as much man as any woman, or little male sugar baby, could ask for. Despite his ex-wife's reasons, I just knew I wanted to please him. Although I never told him, the sex alone would have kept me around after a while. The money was nice, but the cock and the cum were much sweeter.