0 comments/ 58996 views/ 2 favorites Clare's First By: mcdonng Joanne was stunning; small, blonde and had an amazing figure. She was wearing a short denim skirt and a stripy top, through which her nipples were clearly visible. She often didn't wear a bra, as her ample breasts were pert enough without one. Our lovemaking was always passionate, and we tried to make it as varied as possible, in as many places as possible. Her parents were very strict and didn't believe in sex before marriage, so making love at her house was always difficult, but it didn't stop us. Joanne had a younger sister, Clare, who was every bit as gorgeous as Joanne, if not better. I had fantasised about making love to her many times, but knew that she was off limits. She was very sexually aware, and we flirted often; much to Joanne's annoyance. Joanne and I walked back to find that it was empty. Within seconds I had removed her top and was kissing her pert breasts and rock hard nipples. I felt my trousers loosing and Joanne pulled out my already hardening cock. We moved to her bedroom, and whilst kissing her my hand moved between her thighs. Her legs opened involuntarily giving me better access to her sex. By now I was in no mood to take things slowly, so I lifted her skirt, removed her wet knickers and rubbed my cock along the length of her glistening slit. As I pushed downwards the tip of my cock entered her, she met my stroke and my cock filled her right up to the hilt. I lifted her legs to gain better entry as I pushed in and out of her. Joanne's breathing became heavier and I knew she was about to come. I felt my balls rising, and as she screamed in pleasure I pumped what seemed like litres of spunk into her wet pussy. We lay there for a few seconds, exhausted. I pulled out of her and started to get dressed, and whilst I was pulling on my shirt I heard a noise outside the bedroom door. I quickly went out to check but saw nothing. I met Joanne the next day as usual, and she told me that Clare had been watching our lovemaking and that she was threatening to tell her parents. I panicked knowing that this would be the end of the relationship if they found out. However, it transpired that Clare was still a virgin, and wanted someone experienced as a first lover, and if I made love to her like I had Joanne, then everything would be ok. I had wanted to make love to Clare for a long time, and now I was finally going to get my chance. The following weekend was chosen as her parents were out all day Saturday. Joanne led me to the living room, and she began to stroke my cock through my trousers. Joanne called to Clare. She looked stunning as she entered the room. She was wearing a low cut black dress that hugged her figure and just about covered her shapely bum. Joanne beckoned to her, she walked over and sat down beside her sister. Joanne pulled out my cock and started to slowly wank me. She placed it in Clare's hand. Instinct took over, and Clare got the hang of it very quickly, and soon she was wanking me like an expert. Joanne removed my trousers and fondled my balls. I kissed Clare's neck and pushed the strap of her dress off her shoulders. Like her sister she had excellent breasts and I fondled them through the material. I pulled her dress down further and placed my mouth on her right nipple. She gasped as I licked and caressed her nipple and played with the other with my hand. My cock pulsed at her touch, and I pulled away, knowing that I would come if she continued. I kissed her neck, and whilst doing so allowed one of my hands to move lower until it was just below her belly button. She knew what was coming, and again she gasped, but then relaxed and my hand moved lower. She involuntarily breathed in and opened her legs allowing me better access to her sex. As I expected there were no knickers. Soon my finger was resting on her clit. Her breathing increased and I could tell that she was having the beginnings of her first orgasm. Clare lay on the couch and removed her dress, she lay there completely naked ready to be taken. My cock was rock hard now, and I positioned myself between her thighs. Her eyes were closed as I moved my cock slowly over her wet slit. I pushed gently and my knob entered without a problem, but came to a stop as I reached her hymen. I pushed harder and broke through. She cried out in pain, but it soon passed as I pulled out. I pushed in a little further each time until I was fully inside her. Slowly I started to get in to a rhythm, she was inexperienced, but instinct told her to meet my strokes. She cried out again, but this time in ecstasy as she climaxed. I too was close but carried on. I increased my speed and she wrapped her legs around my back screaming at me to fuck her harder. My balls started to rise and then I could feel my cum pulsing into her wet pussy. I pulled out, and Joanne came over, lay between Clare's legs and began to expertly lick her out. Clare was in heaven. Within seconds my cock was hard again as I saw this amazing sight before me. I lifted Joanne's skirt, pulled her knickers to one side and slid into my girlfriend. Joanne and I broke up soon after that, so we never repeated that night, but Clare still smiles at me as we pass in the street. I wonder if she still remembers her first time. Clare's First Time at the Club The box arrived via courier. I pulled the card from the attached envelope, but didn't need to open it to know that it was from Gabriel. The heavy, ivory vellum had been custom made for him. Correction, technically it had been made for me. I ran a finger across the elegant, embossed letter "M" that graced the front of the card. I had been a little confused the first time Gabriel showed the card to me since none of his initials begin with the letter m. He quickly pointed out to me, however, that the initial represented a very important identity; Master. My fingertips also detected the slightly raised pattern that covered the rest of the card. You had to look closely to see that the pattern was made up of tiny butterflies – put there to remind me of my submission. The butterfly is the symbol I chose to represent my metamorphosis from a boring, vanilla existence to the vibrant D/s adventure that I now shared with Gabriel. He usually managed to incorporate butterflies into a lot of the gifts he gave me. Gabriel is very thorough in that regard. The smile that resulted from my musings evaporated once I opened and read the card. This was it, then. He'd told me that it was going to happen, but I foolishly believed that we'd discuss the whole thing before any decisions were made. I sometimes forgot that the authority and control I maintained in my day-to-day life was not recognized behind our metaphorical bedroom door. Luckily, I usually remembered that fact before it got me into trouble. Unless, of course, I was looking for trouble. Today, though, was not the day for trouble, so I took a deep breath to help calm my nerves, and reread the note. Dear Clare, I've decided that we're going to the club tonight, and the evening won't be spent in observation. Your participation will be required. I won't go into details here. The anticipation will only add to your experience. Your outfit for the evening is in the box. Wear only what's included – no jewelry, no bra, no panties. I've already planned for a meal to be waiting for us when we return home, so eat something light this afternoon, and be sure to drink plenty of water. I'll pick you up at 6 pm. Until tonight, Master I put down the notes and looked at the box sitting on the table in front of me. What kind of outfit did Gabriel send? My mind was in a jumble. I had visions of chains and strategically placed strips of leather. There was only one way to find out what was inside, so I lifted the lid. The shoes caught my attention first. They were gladiator –style sandals with a three inch heel and made from black leather. At least they were cute, and had a manageable heel for walking. I set the shoes aside, and pulled out the bundle of black fabric; the only other thing that was in the box. I stood and shook it out. It was a black dress. The top, with its crew neckline and long sleeves, both trimmed in thin bands of black leather, was made from a thin, opaque sort of fabric, which was embroidered with a delicate paisley pattern. I put my hand under the fabric through the neck and could make out its shape and lighter tone easily. I assumed that there was an attached camisole somewhere inside dress and had the random thought that the pattern would not really stand out unless the camisole was a contrasting color. The skirt was also made from black leather and had a flared shape. It was short and would probably only hit me mid-thigh. I just hoped that it was going to be long enough to cover my ass. Otherwise, I would end up self-consciously tugging on the damn thing all night. The overall effect of the dress was naughty and nice at the same time. I took the dress and shoes into the bedroom, and then headed to the kitchen to eat. I was glad that we weren't going to have a big meal before going to the club. My nerves would have made eating a chore. Our plans for the evening seemed distant at this point in the afternoon, though, so eating wasn't a problem. An hour later I had showered, applied my makeup and had styled my hair. All that was left to do was to get dressed. I pulled off my robe, picked up the dress and flipped it upside down to shake the inside layer into place. It wouldn't be a bra, but it was better than nothing at all. My breasts are a bit more than a handful, so I hated going without a bra – a fact that I knew Gabriel knew and always chose to ignore. He liked to push me out of my comfort zone. I looked down at the dress. Where the hell was the camisole? An understanding of the situation began to form as I gave one last shake, then with trembling hands, turned the dress inside out. No attached camisole. No bra. Just my bare breasts covered by that thin fabric. The chime from the clock downstairs reminded me that Gabriel would soon arrive. I straightened the dress and pulled it over my head and into place. My mouth dropped open when I saw my reflection in the mirror. The lighter skin of my bare breasts could plainly be seen through the top. The black fabric was stretchy, yet form fitted enough to kind of hold my breasts in place. It was also tight enough that the texture of the paisley pattern lightly rubbed against my nipples, causing them to harden and stay hard. I turned and saw that if I bent over the skirt would just barely cover my naked ass cheeks. Between the see-through top and the barely there skirt, I was exposed enough that I wouldn't be able to be seen in a normal place of business. I was halfway to my closet to look for a different outfit when I heard a voice say, "Don't even think about it." I was startled enough to jump. I had been so caught up in how I looked, that I hadn't even heard Gabriel come into the house. I wrapped my arms across my chest and turned. "Put your arms down so I can see you." "The camisole is missing. You can see my breasts right through the fabric," I answered; my arms still in place. Gabriel paused briefly, and his tone changed. "The camisole isn't missing. I purposely had it removed. Now put your arms down so I can see you, Clare. I won't ask you a third time." That change in timbre always seemed to flip an invisible switch inside me. It was the signal that my obedience was required, and I was so attuned to respond to his authority that my pussy would moisten whenever I heard "the tone". This time was no different. I quickly answered "yes, Sir", and lowered my arms and my head. Gabriel walked over and circled me, then gave a low whistle. "From afar you look sweet and demure and completely covered. It's only when I get closer and see those luscious breasts with their hard nipples that I realize you are totally made for sin. All of the boys at the club are going to want to play with you. He put a finger under my chin and lifted it until I was looking at him. "Don't ever hide from me. You are beautiful and sexy and I know that I'll be a very proud Dom tonight. Is that clear?" I nodded. "Good." He bent and gave me a quick kiss. "Put on your shoes then come over to the bed and bend over at the waist, resting your arms on the mattress." "Yes, Sir." I walked over to my dressing table, sat down and buckled the shoes into place, before walking over to the bed to get into position. The heels caused my ass to be canted to the perfect angle for Gabriel to take me from behind. My pussy was already aching, and I couldn't wait to feel his big cock working its way inside. It wouldn't take me long to cum, and an orgasm would go a long way toward calming my fear of tonight's unknown activities. Gabriel moved behind me and ran his hands along the back of my thighs, up to my buttocks, pushing the skirt up and out of the way. "Good girl. No panties." I felt a finger probe the wetness below, and then push inside. I spread my legs to give him better access. He pumped his finger in and out a couple times, and then withdrew. I groaned, and got a sharp slap on the ass. "Have patience, little girl. Your cunt will have its turn later. Right now we're going to prepare your ass for the club. I brought you a present." He walked to the head of the bed and picked up a small gift bag that I had failed to notice. He sat on the bed and leaned on one arm, so that his head was near mine. Then, he tipped the bag so the contents fell out with a soft thump. My gift was a black anal plug, but not any ordinary plug. The bulb of the plug was about two inches in diameter. There was a decorative leaf pattern printed in silver along the slim neck, and sitting at the end was a bloomed, black rose. Gabriel tapped the plug with a fingernail. It was glass. "I had planned to cool this in the freezer before I put it in, but the sight of your breasts in this dress distracted me, and now we don't have the time." He jumped up, grabbed the plug from the bed and the bottle of lube from the night stand, and walked back around behind me. I tensed a little when I felt his finger rub across my anus. "Relax, Clare. I'm just getting ready to use the lube. We've done this before, so there's no need to be so tense." "I know. I'm just a little nervous about tonight, and that's making me a little jumpy. I'll be okay." "Good girl." I felt the first wet touch of the lube and then Gabriel's finger was pushing it into my ass. He wiggled the finger and pulled it out. It was only seconds before I felt two fingers pushing back inside me. Just as quickly, he spread his fingers, stretching me. I moaned and dropped my head to the bed as his fingers pumped and stretched. He splayed his fingers once more, and I heard him say something about the lube. I felt his other hand press against my right cheek, then felt the cool lube filling my open hole. "Time for the plug." Gabriel removed his fingers. I could hear him moving behind me, lubing the plug, I assumed, and then I felt the tip of the plug put into place, and the pressure began as it was pushed forward. The first sensation was cold until the glass warmed from contact with my body. Then, there was the prick of pain, as the ring of muscle stretched wider and wider to accommodate the plug. There was no easy push and pull tonight to get me used to it. Gabriel pushed the plug with slow, steady pressure. "Push out against the plug," he said. I whimpered when the largest part of the plug pushed its way inside me. I wanted to move away from the pain, and was tempted to say so, when the plug popped into place. Gabriel pushed the plug deeper until the rose at the end was nestled snugly against my ass hole. I let out the breath that I was unconsciously holding as he wiped up the excess lube. "Don't move. I'm going to clean up a bit, and then we'll go." "You can stand up now." He said a few minutes later. "We need to get going." He stood behind me, with his hands on my hips, as I righted myself. I was a little light headed for a moment and leaned back against him. His hands moved up to cup my breasts and I felt his teeth tugging my earlobe. "I love seeing you displayed for my pleasure. Your obedience excites me." He pressed his cock against my ass, and the combined feeling of his firm cock and the pressure against the plug made me moan. I felt him smile against my ear. He gave my breasts one last squeeze before leading me out of the house and to his car. Twenty minutes later we turned and drove up a long, tree-lined lane before pulling up in front of the club and handing the car off to the valet. As he was helping me from the car Gabriel asked, "Do I need to remind you to keep your arms away from your chest?" "No, Sir," I replied. The club was housed in what was once the mansion of a 19th century lumber baron. Though the mansion, known as Fairborn, retained the original classical revival style exterior, the inside had been remodeled by the owners. Once inside, I forgot to be self-conscious. The beauty of the rich marble and hand-carved wood still managed to amaze me even though this wasn't my first visit. My eyes were immediately drawn to the wide, central staircase. Several people were on it as they traveled to and from the second floor. To my left were the rooms that had originally been the lumber baron's library and connected office. During the remodel, the center wall had been removed, so that it was now one, large room, which was officially named "The Masters Lounge", but was usually just shortened to "Masters". The dark wood and some of the library shelves had been kept. Adding to the masculine feel were groupings of dark brown, leather chairs and sofas; interspaced with small tables and soft lighting. A shiny, wooden bar ran the length of the one side wall. There were also two smaller lounges in the foyer. The room to my immediate right has been partitioned, and now housed a reception area and Fairborn's offices. The room next to the offices had been converted into a women only lounge, called The Mistress. It was set up just like the larger lounge, but with a lighter color scheme. The third lounge, Bound, was located next to The Mistress, in one of the two rooms that were situated behind the staircase. It was similar to The Mistress in size and that it also had a bar area, but differed in décor. Bound was all about comfort; plump, cushioned furniture, with pillows and soft comforters and throws. It was a retreat for those of us who might need a break from play, and was also the only room in the house not open to the dominant set. The final room just off the foyer was a dining room. It was decorated in rich jewel tones, but was otherwise set up like any other restaurant. The slight pressure from Gabriel's hand on my back recaptured my attention as we headed over to the reception area. Members were required to sign in themselves and their guests. Once we were signed in, we were escorted to an office. A guest services manager went through the rules and protocols since this would be my first time as something other than just a visitor. We quickly completed the orientation, and then moved on to my bracelet fitting. All subs wore color-coded bracelets. The color of the bracelet let everyone else instantly know your level of participation. There were four colors: 1. Green / Permission Granted (the sub is available to any Master/Mistress at any time). 2. Blue / Permission Required (the sub is available by request only). 3. Yellow / Limitations (interested parties must speak to the sub's Master/Mistress for details). 4. Red / Not Available (the sub is only available to his or her own Master/Mistress). The manager turned and pulled a wooden box from the cabinet behind his desk, and then directed his question to Gabriel. "What color will the young lady be wearing tonight?" "She will wear yellow." "Very good, Sir." The manager measured my wrist, pulled out some sort of tool, and then sifted through the box before finally pulling out what looked like a yellow ball. He carefully unrolled the ball to reveal a flat ribbon with thin cords hanging from each end. I figured that he would just tie the ribbon around my wrist. Instead, he draped the ribbon over the top of my wrist, turned my arm over and lined up the two ties across the underside of my wrist. Pinching the ties together with his fingers, he asked, "How does this feel? Too tight? Too loose?" I kind of twisted my wrist. "No, it feels okay." Gabriel leaned over and fiddled with it for a minute and agreed that it was a good fit. The manager nodded, picked up the tool and flipped a switch. He gingerly held the ties and placed the jaws of the tool where they intersected. He tightened his grip for a few seconds, and then released the jaws. The ties had been perfectly crimped, with the excess falling to the desktop. It was a perfect fit. The manager began putting things back into order. "The receptionist will remove the bracelet when you leave for the evening." Gabriel nodded, and soon after, we were led back to the foyer. Gabriel looked down at me. "Are you ready?" My nerves came back full blast. "Yes, Sir," I replied and tried to smile. I must not have pulled it off, though, because he chuckled and grabbed my hand. "Come along. Let's get started." We walked to the top of the stairs. Most of the rooms on the second floor were set up as exhibits of sort. The door and the front wall were clear, allowing everyone in the hallway to see what was happening in the room. Each room also had a small seating area to one side for those who wanted to watch for more than a few minutes. The majority of the space, however, was filled with toys and furniture. Most rooms had a spanking bench, St. Andrews Cross and restraints attached to the ceiling and walls. A few had a cage or a swing. All of the rooms were currently being utilized. "Why don't we go down to this end?" He gestured to the right. "Then we can get a look at each room as we make our way to the stairs for the third floor." Knowing that my agreement was not needed, we turned and started walking down the hallway. We passed several people as we walked. There were some men and women who were alone and others who had subs with them. It felt as if all their eyes were glued to my chest. "Gabriel, it's good to see you!" We paused as a woman in a leather cat suit walked toward us. She was followed by another woman who wore nothing except a pink collar and a green bracelet. She immediately dropped to her knees once she reached her Mistress' side. "Jessica. It's nice to see you as well. You remember Clare?" Jessica turned to look at me. "Yes. I recall that you both were just visiting the last time I saw you, but", she glanced at my wrist; "I see that this time you've come to play." She looked back to Gabriel and quirked an eyebrow. "Limitations?" "Yes, it's her first time here for play. I have something specific in mind." "Well, I hope breast play is involved. These are lovely." She gestured to my breasts. "May I?" Gabriel nodded, and before I could grasp what was happening, Jessica palmed both of my breasts. I stiffened for a moment, but a pinch on my ass from Gabriel reminded me to behave. She bounced and squeezed my breasts before pinching and pulling on my nipples. "They have a nice heaviness, and these plump nipples just call out for clamps." She directed her next comment to me. "You and I will have some fun once that bracelet is green, my dear." I knew what was expected of me, so I replied, "Yes, Ma'am." Jessica gave one last, hard pinch to each nipple, and then stepped back to look at her handiwork. "Gabriel, if you insist upon hiding her tits under that fabric, then you should at least highlight them. Rouge would have made them stand out better." "I'll admit that I didn't think of that." "Will you allow me to give them some color? It'll only take a couple minutes." Gabriel's slight nod was all the permission she needed. Jessica snapped her fingers and her sub jumped to her feet. "Leta, Give her some blush. No bruises. I only want to see rosy nipples when you're done, or you'll be severely punished. You have two minutes." "Yes, Mistress." Leta moved in front of me, and put her hands on my hips. Because she was barefoot, the top of her head only reached my nose, so she only had to bend a little to be able to reach my nipples. Within seconds of her Mistress' command, her mouth had latched on to a nipple. She would alternate between sucking and biting, before switching to the other side to repeat the process. I was frozen in place. I had never had my nipples (or anything else) sucked by a woman. I couldn't decide if I really liked it or not. Her lips were as strong and as firm as a man's lips would be, but they were also somehow soft at the same time. It was a confusing feeling for me. I could hear Gabriel and Jessica speaking, but my entire focus was on my nipples. Then Gabriel started playing with the rose in my ass, and my arousal started to accelerate. Clare's First Time at the Club "Time's up!" Jessica's voice made me jump. Leta's lips popped off my nipple and she gracefully dropped back to her knees. Gabriel and Jessica stood in front of me and stared at my chest for a couple seconds. Finally, Jessica patted Leta's head, and praised her for a job well done. The two friends said their goodbyes and the four of us split up and went our own way. We had walked a few feet when Gabriel said, "Your nipples are bright red and your face is flushed. You look like you've just been fucked." I groaned and he continued. "You know don't you, that Jessica will won't be happy until she's had her way with you?" "Great, just what I need." "What was that, Clare?" The coolness of the tone told me that he wasn't amused. "I'm sorry, Sir. I said, yes, Sir." "That's what I thought you said. Now, how do you feel about Jessica?" "I honestly don't know, Sir." "Fair enough. We'll discuss that later. How did you like having your nipples sucked by a woman?" "I'm not sure about that, either, Sir." We had stopped in front of a room to watch as a sub was hogtied and placed face down on a large, flat swing. The swing was then rocked back and forth as her pussy as fucked by a woman wearing a strap-on dildo, and her mouth was being fucked by a man with a large cock. The fucking couple would increase the speed of the swing every three or four rotations. Gabriel leaned close to me. "Don't lie to me, Clare. You know that your cunt is soaking wet right now. You enjoyed having your nipples sucked." I turned to look up at him. "I wasn't lying, Sir. Did it feel good to have my nipples sucked? Yes. Did I enjoy having a woman suck my nipples as much as I would have enjoyed a man sucking them? I don't know. You know that I'm not attracted to women, so I'm inclined to say no is the answer to that question. Did my pussy get wet purely as a response to having my nipples sucked, or did having a woman suck them contribute to the arousal? It's a confusing issue for me, so as I said, I'm not really sure." He looked into my eyes for a couple minutes. "I think that this is a conversation for another time, so we'll drop it for now, and just enjoy ourselves." Gabriel spun me back around in time to see the guy shoot his load all over the tied up sub's face. There was nothing more to see here, so we continued down the hall, peeking in on a few of the "exhibits" along the way. We paused at a room near the end of the hallway to watch a Dom manipulate hot wax on the cock of a male sub. Gabriel's hand was under my skirt, and he would give my cheek a pinch every time a drop of wax hit the sub's cock. Needless to say, my ass was getting pinched a lot. "I can think of a better way to make that ass pink." We both turned to look at the man who spoke. He was of an average height and an average build. He wore his wavy, blond hair a little long. He was tan and wore gray pants with a dark blue shirt, but actually looked a little sloppy compare to Gabriel's clean cut look and all black suit, shirt and tie. "I think a good paddling is just what your sub needs." He pointed to my bracelet. "What are the limitations?" Gabriel stepped away from the window and walked over to the stairway that led to the third floor. The Dom and I followed. "I will allow her to be strapped to a bench and paddled. You may use whatever assorted paddles are available, but no whips or canes. You are not allowed to hit hard enough to cause bruising or draw blood. I will also remain in the room for the entire session, and will tell you when it's time to stop." I was surprised that there were so many stipulations. Grateful, but still surprised. I was sure that the Dom would decline and leave. I was wrong. "I accept your conditions." "Very well. Let's go up. I have a room reserved." Gabriel led the way up to the next level. The third floor contained a variety of smaller, closed rooms that had to be reserved in advance. A couple of the rooms were set up for specialized play; like water or medical play. Most of them, though, were set up like the rooms downstairs, with a variety of toys and furniture, but without a viewing area inside the room. These rooms also had attached bath and dressing rooms. Participants on the second floor had to use one of the two large locker rooms that were situated at either end of that hallway. We stopped at the fourth room, Gabriel scanned his key card, and we were quickly inside. The lights came up, and I couldn't help but stare at the large assortment of toys and devices that were displayed on the far wall. The Dom was already perusing the selection of paddles by the time the pneumatic closer made the door shut with a loud click. The sound was harsh in the quiet room. The Dom headed toward the dressing room. "I need to get ready. I'll be right back." Gabriel put his hands on my shoulders. "Still doing okay?" he asked. "Yes, Sir." "Good girl. Remember, I will be right here in the room with you the entire time, but he will be in charge of the paddling. Don't speak to me unless I first speak to you. I won't give him any directions or intervene unless I see a need. Do you understand?" "Yes, Sir", I replied. Before we could say more, the side door opened and the Dom strode out of the room. His street clothes were gone. In their place he wore black leather. The top consisted of a few, thin, leather strips draped across his torso. In place of the slacks he wore a pair of tight, leather shorts. They weren't ordinary shorts, though. The groin area was completely cut out leaving his hard cock fully exposed. Gabriel looked him over, but didn't comment on the new outfit. "We're almost ready to begin. We just need to agree on a safe word." "There's not really any need for one," the Dom began. "There is always a need for one." My Master's tone came through loud and clear. He turned to me. "Clare, your safe word is buffalo." "Yes, Sir. Buffalo." Gabriel turned back to the Dom. "Do you agree?" "Yes, buffalo it is." "Wonderful. Clare, get into position on the bench, and we'll strap you in place." "Yes, Sir." I took a steadying breath and climbed on to the bench. I knelt on the padded leg rests while Gabriel adjusted the height of the bench, and then bent forward into position. I felt the two men buckling the straps across my calves and thighs. There was one strap that buckled around my waist, and finally, my wrists were buckled in on the arm rests. My skirt was lifted and tucked under the waist strap, and then I saw Gabriel sit in a chair that was placed in front of me, but off to the side. He lifted his hand and did a sort of "get down" sort of motion. I took that to mean for me to lower my head, so I let it rest against the padded bench. I could hear the Dom touching things on the wall. Then it was quiet. "Oh! What's this?" I felt the plug being slowly pulled from my ass. "Clare's ass is in training. I would appreciate if you don't hit the plug with the paddle. It's glass." "Of course. May I play with it?" "Yes, but it's not to be removed." The Dom began fucking my ass with the plug, using shallow, but firm strokes. He would pull it out just enough for the widest part of the bulb to stretch my hole, before thrusting it back inside. "She's so tight. Her lovely little anus clenches so hard around the plug. It must feel wonderful around your dick." On that final word, the plug was seated deeply, with a firm push SMACK! The paddle landed hard on my right cheek. I jumped as much as I was able to given that I was strapped in, and gave a startled scream. SMACK! Now it landed on the left cheek. These were not light, teasing slaps. My ass was already starting to burn. One, two, three, four; the paddle landed back and forth from one cheek to the other. I lost track of the number at ten as the burn and heat became continuous. I was straining to move away from the paddle but was buckled in too securely. SMACK! SMACK! SMACK! SMACK! I cried out each time the paddle hit my flesh. Then, there was a short pause as he moved to the exposed area of my upper thighs. He continued his paddling until they too, were on fire. Suddenly, he stopped. I was panting and aware of only the pain and the heat. The Dom walked around to the front of the bench. "Look at me." I lifted my head, and he used the end of the paddle to lift my chin higher. "No tears. Does that mean that the paddle is only tickling you?" He started rubbing his cock with his free hand. "No, Sir. It's not tickling." The paddle pushed my chin higher. "The correct response is, 'No, Master Richard'." I silently groaned. During the drive to the club Gabriel specifically told me that I was only allowed to address the other dominants as "Sir" or "Ma'am". He stressed that I did not have a Mistress and that he was my only Master. I wondered if this Dom was going to have a problem with that. I waited a moment to see if he would say something. When he remained silent, I repeated, "No, Sir. The paddle is not tickling." His hand was now wrapped around his cock. "Are you purposely disobeying me? My name is Master Richard." "No, Sir, I'm not purposely disobeying you. My Master is the only person allowed that title." His breathing sped up, and his hand squeezed his cock. He turned his head toward Gabriel. "Your rule?" "Yes." I saw his hand give his cock one more squeeze before he let the paddle fall to the floor, and then walked away from me. I dropped my head back down to the bench. I thought we might be finished, but I should have known better. I heard Richard grab something from the wall. I tried to turn my head to see what he had, but the angle was all wrong. THWACK! THWACK! Fire burned its way across my ass from one cheek to the other. This paddle was thinner than the first, and the sting greater. Blows rained down on my ass and thighs. My body was tense and I was jerking against the restraints; trying to find some way to shield my ass. This time it didn't take very long for the tears to begin leaking from my eyes. Internally, I was telling myself to yell the safe word and be done with the pain, but I wasn't quite ready to say it out loud. My Master felt that I was ready for this, so I wasn't going to disappoint him. The blows stopped as quickly as they had started, and Richard once more fucked my ass with the plug. I moaned involuntarily, and realized that it felt good; that mixture of pleasure and pain. It helped me understand why Master thought I was ready for this experience. Richard left the plug, walked in front of me and lifted my chin with the paddle. His free hand was now actively pumping his cock. It was a dusky, purple color, and pre cum was leaking down the back of his knuckles. He looked at me and smiled. "I fucking love a tear-stained face." He let go of his cock, and ran his fingertips through the tears on my face. Out of the corner of my eye, I saw Gabriel get up and walk toward us. Richard closed his eyes and rubbed his wet fingertips along his cock. Then, he fisted it, and started to jack off in earnest while mumbling something about wanting to make me cry all over his dick. "That's enough." Gabriel pushed the paddle away from my face. "We're done here." Richard sneered at Gabriel before turning sideways and ejaculating with a yell all over the paddle. His chest was heaving as he finished. He gave one last pull on his cock and turned to face me. "You would lick all the cum off this paddle, then suck my dick clean if you were my slave." "Then it's a good thing that she is mine. It's time for you to leave." "Fuck you!" With that parting sally, Richard threw down the paddle, and stomped to the dressing room. He came back out a couple minutes later, wearing his slacks and shoes. He was pulling on his shirt as he slammed out of the room. Gabriel had all of the straps undone by the time Richard was gone. I started to push myself up, but a hand on my back stopped me. "Stay there. I need to take care of a couple things." He walked over to a mini fridge, pulled out a small bottle of water and handed it to me. "Drink the entire bottle. I'll be right back." "Yes, Sir," I said between sips, and felt Gabriel place a kiss on the top of my head before he disappeared into the bathroom. I had almost finished the drink when I heard him come back into the room. He was carrying a bowl in one hand, a jar in the other and a cloth was draped over his arm. He set everything down on a table near the bench, dipped the cloth into the water and wiped the tear stains from my face. Then, he went behind me and carefully removed the plug. I felt better already. Once the plug was out, he bathed my sore cheeks and thighs. The water was cool and the cloth was silky smooth, but it was still painful. Once he was through, he kissed each cheek, and then rubbed cream into my skin. "This will help with the soreness, but I'm afraid that you're not going to be able to sit too comfortably for the next few days." He flipped my skirt back into place, and carried everything back into the bathroom. I heard water running for a while. When he returned, he was drying the plug. He tossed the towel on the floor near the deserted paddles and slipped the plug into his pocket. "Okay. It's time to get you off this thing. You're probably going to be a little stiff, so let me help you." I pushed myself back onto my knees as Gabriel wrapped an arm around my waist and lifted me off the bench. I tried to straighten my legs to stand, but my knees immediately buckled due to numbness. Gabriel scooped me up and sat in the chair he'd been using earlier. I winced as he settled me in his lap, but the feeling was starting to come back into my legs, and the "pins and needles" almost hurt more than the pain in my ass. My stomach picked that moment to rumble, and Gabriel chuckled. "I had planned to end our time here with a drink, but perhaps we should just head home to our meal." We gave my legs a few more minutes of recovery time, and then made our exit from the club. There was not as much traffic at this time of night, so we made it home in good time. A delicious smell hit me when we walked through the door. "Mmmm. That smells like lentil soup." I plopped down on the couch. Gabriel turned on a couple small lamps as he walked over to the dining room table and picked up a plate. "It is lentil soup; with a salad and warm bread. I knew we'd get home late, so I didn't want to have anything heavy, but I also knew that you'd need more than just a snack." He set a small plate of grapes and bits of cheese, and a glass of wine down on the coffee table. "I need to warm up a couple things. Take off your shoes and relax while you nibble." He snagged a grape. "I'll be back shortly." It didn't take long for me to make myself cozy and dig into the snacks. I was sipping wine when he walked back into the room, barefoot and wearing just his slacks. "I wondered if you were going to slip into something more comfortable. " I said with a laugh. "Oh, I plan to slip into something, but I need a snack first." Gabriel prowled to the couch and knelt in front of me, lifting my legs up over his shoulders. He pulled my ass to the edge of the couch, and dove in to eat. He went right to my clit and started sucking. I moaned deep in my throat as pleasure zinged through my body. My pussy had been ignored all evening, and his mouth and tongue felt so damn good. He usually teased me and took his time when he was sucking my pussy, but tonight he went right to the prize. He nibbled and sucked and lapped at my clit. I was squirming and moaning; begging him to let me cum. He must have thought he went too quickly because his tactic changed, and he firmed up his tongue so he could fuck me with it. That made me ramp up even more, which made my pussy even wetter. I could feel the combination of my wetness and his saliva dripping down my ass. His fingers suddenly plunged into my pussy; fucking me hard and deep the way his tongue wasn't able. I was thrusting my hips against his fingers; barely noticing the roughness of the couch cushion on my sore bottom. He lifted his head and blew cool air on my pussy. "Someone is certainly eager for her Master's cock." I was still pumping my hips. "Yes, Sir. Please!" He dipped his head and started lapping at my clit, but pulled his fingers from my pussy, slid them down to my puckered hole to spread the wetness, and then thrust two fingers in deep. There was a slight twinge of soreness after having the plug in all night, but I still cried out in pleasure, and grabbed his head to try to keep him focused on my clit. "Oh please, Sir! I need to cum!" "So do I." "Nooo," I moaned, as he pulled back. My disappointment didn't last long. He worked and wiggled and managed to get his pants off while keeping my legs draped over his shoulders. Then, I heard the pop of a lid. Lube! "You're not going to fuck my ass?" I asked. His fingers were one thing, but I wasn't sure that I could handle his cock tonight. "I' don't think you're in any position to tell me what I'm going to fuck, are you Clare?" His slippery fingers began penetrating my anus. "No, Sir." "Your ass belongs to me and I will fuck it whenever, wherever and however I want. Won't I, Clare?" His fingers continued to move in and out as he added more lube. "Yes, Sir." He paused and looked directly into my eyes. "I loved watching you while your ass was paddled; your face was so expressive. Seeing you restrained and hearing your sweet cries had me hard and heavy from the start. I wanted to fuck you then and there, but made myself wait. I can't wait to feel the grip of your tight little hole on my cock, and feel the heat from your poor, red ass on my balls as I push my cock in deep. I'm going to start fucking you, and my hips and balls are going to smack against your sore ass over and over." He shifted our bodies so that we were lying lengthwise on the couch. I moaned and closed my eyes; thinking about everything he said. "Open your eyes and look at me." I looked up into his blue eyes. "You're going to enjoy the pain from my balls smacking your ass, aren't you Clare?" "Yes, Sir," I croaked. "You enjoy feeling that little bite of pain. It amps up your pleasure, doesn't it?" I nodded. "In fact, I bet that you'll beg me to fuck your hard, won't you?" I nodded a second time. "Answer me, Clare. Tell me what you want." The intensity in his eyes and in the tone of his voice excited me and caused my stomach to do somersaults. I licked my lips. "I want you to fuck my ass hard, Sir." "Good girl," he said as he seated his cock all the way in my ass in one, swift stroke. I cried out and tensed from the invasion. There was pain, but it was relatively minor after being opened up by the plug all night. He wiggled his hips and the friction caused a stinging sensation on my ass. He was right about me. I liked having my asshole stretched, and I loved feeling it filled with his cock. I even loved the way the soreness felt. The combination of those things with the pain from the paddling was making me ready to explode. Gabriel's left hand gripped my hair and held my head in place. "Are you ready to cum, Clare?" I nodded. "Then tell me." I pulled his head close to mine and looked deep into his eyes. "Sir, please fuck me hard and fast and make me cum. I want to feel you fill my ass when you cum." He growled and began to piston his hips; giving me exactly what I wanted. I was moaning and crying out for him to fuck me harder and faster. A drop of sweat dripped from his face on to my lips, and I licked it off while he was watching me. He adjusted his angle and somehow managed to increase the friction and throbbing of my ass. Clare's First Time at the Club "Sir, please!" I yelled. "Play with your clit and get ready to cum." I reached down and rubbed and pinched my clit; feeling those soft beginning waves of an orgasm start to ripple. I was so close to coming. My hand was moving quickly over my clit. "Are you ready?" "Yes, Sir," I gasped. "Then cum right now!" The last word was shouted as he thrust hard once, twice. I exploded into a million pieces! Waves of pleasure radiated from my pussy up to my head and down to my toes. He thrust a third time, a fourth, and then gave a hoarse yell and froze above me. I continued to throb as his cock jetted warm pulses of semen and filled my ass. We were both gasping for breath, but my body was beginning to rebel from being in this position for so long, so I started to move my legs. Gabriel managed to free my legs and tried to roll so we were side by side – and promptly fell to the floor with a soft "oomph". I rolled to the edge of the couch and looked down at him; laughing, then gave a startled shriek when he pulled me over the edge and on top of him It was his turn to laugh. "I'll always have the last laugh, little girl. Come on." He helped me up as we stood, and then pulled me into a hug. "I was very proud of you tonight. You handled yourself well." "Thank you, Sir." He lifted me higher and gave me a deep kiss that tasted like "us". "Mmmm. Very nice. We'll discuss everything tomorrow. Let's get cleaned up and eat."