Laugh Cum Cry

I should be used to going out with Garrett in whatever outfit he has chosen to display me in by now, however some days are a little extra. Usually he would also tell me a little about where we are going or who we are visiting. Today was nothing except "I left your clothes for today on the bed."

I went to the bedroom to put on what he had chosen for me and I saw the hanger with a beautiful skirt made up of strips of jewel toned organza fabric which were so sheer I knew it would hardly be a decent covering as it swirled around my legs. The top was a lacy purple bustier that matched one of the colors in the skirt. It felt like the air tickling my legs from the skirt, but it wasn't until I put the bustier on that I realized it was a half cup bra and there was nothing to put over it. As I looked into the mirror at my reflection I saw him walk in behind me. Twirling as I turned to show him the full effect of the skirt and I saw the desire in his eyes that always sent a tingle through me. His gaze went up and down as he walked to me and he smiled.

"Perfect, exactly as I imagined it would look." He told me. "Just a few minor adjustments and we will be ready to go." With that he reached into the top of the bustier and lifted my breast by the nipples to arrange them on top of the half cup. From his pocket he pulled out a clamp like none I had seen before. It looked like two clamps joined end to end but with one turned in and one aiming down. As Garrett attached the first clamp to my nipple it started to make sense because that held tight to me as the lower portion attached to the top of the half-top. It was to hold my nipples out on display over the top of the bustier. He repeated this with the other side and turned me again to face the mirror. The look was stunning. The silver of the clamps stood out against the rich purple and went nicely with the silver collar I was wearing today. To complete the look he handed me a silver anklet that had about a dozen of the tiniest bells I'd ever seen and they sounded delightful as I attached it around my ankle.

As we headed to the door I slipped into my silver high heeled sandals to complete the look. Even with the added three inches from the heels my head only came to Garrett's shoulder which allowed me to fit in perfectly under his arm in the elevator. That also meant his arm reached far enough over to easily reach down to toy with my exposed nipple, which he did all the way to the lobby. Poor Henry, our doorman, I'm not sure if his eyes will pop back in his head after opening the door for us. He did his best to stay focused as he hailed a cab but I could see the bulge in his pants as I slid in the cab ahead of Garrett.

We traveled just a few blocks uptown to 93rd and over to 3rd Ave to a building with a beautiful entrance. The doorman quickly opened the cab for us as it pulled to the curb. He held his hand out to help me as I stepped out as Garrett paid the driver, then turned to see if Garrett had any bags he needed help with. Turning to Garret without so much a second glance at me was a little strange given what I was wearing. "Welcome Sir, Would you be visiting Lady Nessa today?" His voice had the barest hint of Ireland as he spoke.

"Yes, Sean, we are. Would you ring her and let her know we are on the way up?" and with that Garrett guided me in through the open door to the elevators. I had never heard him speak of Lady Nessa and I was curious how often he'd been here to be on a first name basis with the doorman.

The elevator opened as we reached it and as I turned around after entering I could see Sean on the house phone already. There were no numbers on the panel. There were words saying lobby, kitchen and dining, living room, bedrooms, playroom and rooftop. Did this Lady Nessa own the whole building and have one room on each floor? I didn't have to wonder long as he selected the living room button as the doors slid closed silently, the car began to rise.

"On your knees before we enter." I was told and dropped immediately. As I went to put my hands behind my neck, as this position requires, the nipple clamps tightened from the motion causing me to let out a quiet "Oh!". With the briefest look down at me I heard Garrett chuckle but didn't say not to complete the correct position. The door opened to an amazing room. The floors were white marble and polished to a high gloss but the rich dark wood of the furniture kept the room from looking cold and sterile.

Stepping out to greet us was a woman wearing a short black robe open over an emerald green satin teddy that fit her like a glove. She had hair just a few shades darker red than mine, eyes not quite as green and her skin was flawless. "Welcome Lover," she said in greeting to Garrett and I felt a pang of jealousy in that term of endearment.

"A pleasure as always Nessa," he said as they exchanged kisses. "I thought you'd like to meet my own Irish Beauty. This is Kelly and she has just recently taken my collar." I felt him step back as she stepped forward.

"My she is lovely for sure," her hand slid under my chin to raise my face up, but I was sure to keep my eyes down as I had been taught. "Look at me, Lovely" she said in a voice that, like Sean's, had just the musical lilt of Ireland in it. Looking up to her I saw her lips curl into a smile as she asked "And have you brought her for me to play with today?" Again I heard Garrett chuckle as he said "I figured it was time to share. She's been to the Club a few times but only on my arm."

Share? What did he mean, share? Certainly he wasn't going to let this lady play with me. I wasn't sure I was ready for this yet. Garrett could sense the panic rising in me and ran his hand over my head to my shoulder for reassurance. "Well then we can swap if you like,or better yet, play together" She said as she turned to pick up the receiver of the phone next to the elevator. "Send for the new boy to come to the playroom and bring us all up some drinks." Hanging up she pushed the elevator call button to open the doors again. "Shall we?" She stepped in and I was guided back in and we went up two floors to the playroom.

This floor was a softer rubber-like floor that was kinder to my knees then the marble had been. I took in the room as we got out of the elevator. I could see just what she meant in 'Playroom'. The room reminded me of a smaller version of the Club and yet was brighter without being crowded with equipment. There were large floor to ceiling mirrors placed behind each piece, and between each station there were long boards mounted to the wall parallel to the floor with hooks holding every imaginable paddle, strap, flogger and whip. A small sideboard table under each held bottles of lube and lotions, dildos, butt plugs and clamps of every shape, size and color.

Directly across from the elevator was a St. Andrew's cross with loop hooks all around to secure cuffs at different levels. About three yards down, the next station was a board hanging from the ceiling. I couldn't make out what it was, it looked like an old fashioned wooden swing but it was too high up for that. As we got closer I could see there were three holes in the 'seat' of the swing and understood it to be a standing stockade. Further down was padded spanking bench like I'd seen at the Club, it was a wide sawhorse but had wings on the side that could be raised to position you lengthwise verse over. That left open a lot of possibilities and just the thought had my pussy getting wet.

I almost jumped when the doors opened again and from the reflection in the mirror behind the cross I saw the doorman, Sean enter with you on your knees beside him. He carried a silver tray with short glasses, a bottle of Tullamore Irish whiskey and a few bottles of water. Your back was so straight as you struggled to stay upright and go as quickly on your knees as Sean was walking. I noticed your collar was white with silver studs. Your chest was smooth, broad and looked freshly waxed and although your cock wasn't as fully erect as it could be, I saw potential there. Sean walked you to Lady Nessa, turned to set the drink try on a coffee table in front of a seating area behind us and knelt next to it.

"Ahhh, Nessa, This is your new trainee?" Garrett asked, looking at you.

"Yes," she confirmed,"He was sent to me for training but I am having so much fun with him I just might keep him." Her hands ran across your shoulders, over your chest to pinch the nipples that were standing out. The flinch had her frowning down at you and pinching again until you stayed still for her. "He has a will that is proving a challenge to break," she explained. "although I will say his stamina is a delight and his control is getting better. We are still working on his pain levels. Perhaps you could help there too." Lady Nessa had led you towards me as she was talking so we faced each other, both on our knees, both willingly under the command of another.

"Shall we show him how to hold still my love?" Garrett asked me as he reached for the nipple clamps holding me to my top. I knew from his tone what he was asking me to do and I prayed for every ounce of will I had. They had been on almost a half hour so the time limit for safety was closing in. This was going to hurt. I drew in a deep breath and slowly let it out as I had been taught when bracing for something harsh. On the next deep breath I felt him release the left clamp. The pain was incredible and delicious all at the same time as it shot through me as blood rushed back into my nipple. Though I didn't move I couldn't stop the low moan that sounded almost like a sigh as I slowly released the breath I held. Taking another deep breath he removed the other one and again the pain washed over me except not a sound was made, just a single tear rolled down my face.

Lady Nessa all but clapped her hands as she danced up beside you exclaiming "She truly lives up to the meaning of her name." Turning to me she asked "did you know the name Kelly means Warrior in Ireland?"

"Yes Ma'am. My grandparents are from Ireland so I was raised knowing the history and language which means I know Nessa means 'not gentle'. My papa used to call me Nessa on the ball field because I didn't always play nice." I had to smile at that memory as well as the look of shock on her face from my knowledge.

"Oh Garrett, she is delightful, let me play with her, won't you?" The pleading in her voice startled me a bit.

"You may test her if you like. I think you will find her very interesting to work on. Where would you like to start?" Garrett asked as he helped me out of my clothes and led me to the spanking bench she had indicated. Lady Nessa came over to help secure me to the bench. Cuffs on my wrist and ankles were clipped to the sides as I was laid over it.

"Let's bring that one too. Have him watch and learn" she said, snapping her fingers for you to come to her. "Kneel back here in front of her and watch how she does" I wasn't sure if it was having your face inches from me, my Master handing me off to another or not knowing what her testing may be, but I was so stirred up a single touch could surly topple me over the edge. Felling the smooth cool leather on my sore nipples didn't help either, I am sure.

Her hands traced over me from my hair that she moved off my neck all the way to the tips of my toes. It felt so intimate to have another woman's hands on me like this. Others at the club had given my tits or ass a pat or squeeze but this felt like a lover's hands and I wasn't sure how I felt about that yet. Garrett selected a small leather covered paddle, and told her to try me. The force of the blow was not what I was expecting though from her name I should have. The sting radiated and was followed so quickly by the next that they melded together. She was alternating left to right and upper and lower so it was hard to get my bearings. As tears started down my face I saw the look of concern from you but also caught a glimmer of amusement for my discomfort. You were getting harder with every slap of the paddle and Garrett saw that.

Tapping your leg with a crop he had you stand which put your cock right at my mouth. Glancing towards him for permission I took just the tip in my mouth and swirled my tongue around, scraping my teeth over and felt you tense until I drew you all the way in and began another assault with my tongue starting at the base and back out. Your fingers twined through my hair trying to guide my mouth over your cock but you were told to put them back behind your neck. I caught the movement behind you a moment before Garrett struck your ass with the crop. You seemed genuinely confused with the pain and pleasure at the same time. I sucked you in tighter, closing my lips around your shaft and tracing the veins with my tongue. As Lady Nessa continues to paddle me and Garrett applied the crop to you, we both seem to join in being lost. I could feel you relaxing into it so for a few minutes I concentrated solely on the head sticking my tongue into its opening and taking the whole head into my mouth building up momentum with my suction until I took your whole cock as far as I could down into my throat. At the moment you ached for release though hands pulled you away from me and left us both panting.

They directed you back to your knees out in front of the bench where I could not see you. I felt her presence beside me again, and the tips of her fingers trailed across my abused buttocks. "So pretty," she murmured, and there was an edge in her voice, a tremble that was definitely sexual in nature. Her touch provoked fresh waves of pain as she trailed them less than gently across the damage she had done. "Such beautiful marks. Release her." she ordered you. "Now lovely, turn on there and kneel so that I may test your pussy." Lady Nessa ordered. I turn scarlet, and glance over at Garrett who just nodded at me to do as she instructed.

She reached out with her left hand, spreading the lips of my pussy apart and stroked me softly with the edge of a crop tip. I let out a soft moan, the stiff leather material is stroking me right over my clit. I clutch the side of the bench as she continues to stroke me knowing that if she continues as she is doing she will make me cum. He knows me well, watching my face as I near my orgasm. "Kelly," Garrett said. "Yes my Master?" I gasp

"You may not cum yet." I groan aloud, I am so very close to cumming. I struggle to hold back as order but Lady Nessa is continuing to stroke my clit. God!! I don't think I can hold back! Thankfully she moved away from me but left my clit twitching for more.

She snapped her fingers at you and pointed to the sideboard. "Hand me the oil there and come lay on your back next to me" Garrett raised me from my knees and off the bench and had me lay on top of you face up. Lady Nessa made the final adjustments by pulling your cock down and letting it snap back up to nessle between my legs pressed against my dripping pussy. Oil was trickling over my body in a line from my neck, between my breasts, over my stomach and down my pussy. Garrett snapped your hip with the crop again and told you to reach around and work the oil in. I felt your hands slip under my arms and then spread the oil out over my breast. Your big hands were working in circles growing smaller and smaller inward towards my nipples. They were hard little nubs and still sore from the clamps as you flick and pull on them.

Unable to help myself, I let out a soft moan of pleasure. My hips grinding a bit into you I can feel your cock throb and bounce across my pussy as you writhed back. As I did so, your fingers begin to work in circles again, this time growing larger, until again they are going around the fullness of my breasts. your hands cup them, hold them up. Suddenly I feel lips! Her lips close around the hardened nipple of my right breast. Her tongue begins to tease my nipple, coaxing it even harder as you hold them for her to feast on. Leaving my right breast, she begins to do the same to my left, coaxing that nipple into a fuller hardness. My hands grope for anything to hold on to which turned out to be your hips under me. She let go of my breast, and moves down my body, spreading the oil as she goes. I realize that she is heading towards my pussy. I moan softly, and try to move away from her hands. "Kelly" Garrett commanded "You will allow Nessa to continue."

I whimper. I do not think I want this, do not want to be aroused by another woman. But I want to please my beloved Master. My body stills, but no longer attempts to evade her questing fingers. With the crop again, Garrett instructed you to open your legs wider which took mine with them as she knelt between us. Your hands are still teasing and pulling on my nipples. Her fingers spread some of the oil from my mound, down into my slit, over my outer pussy lips, then over the inner lips sliding upward. OH GOD!!! Over and around my clit. I am fiercely aroused now, my clit hard and full. She dips one finger inside my hot pussy, then returns to my clit, teasing it going in circles around it, then back and forth across it. I am moaning, my orgasm approaching swiftly. His voice once again says, "You may not cum yet."

I cry out gasping "Please my Master please, allow me to cum for you. I beg of you!"

"I said No! You may not cum yet! Do you understand me?" I struggle to obey him. The effort is almost too much until I feel her move back again only to have something else slide into me and from your movement and moan I know it is you. She had been stroking you the same time she was playing with me and was now guiding you into me. Your hips rocked up and I feel you going in little by little, going deeper. Your thighs tense as you raise your hips to push deeper still, I suddenly realize she is no longer between our legs but beside us and I hear a sound I know well. Lady Nessa has a vibrator, a vibrator she must be going to use on me!! I feel her fingers spreading the lips of my pussy wide and runs it teasingly around my clit. At first going in circles around it, but then she holds it on my clit directly. I can't help myself, I push my hips upward as you pull me back down on your raging cock where you can feel the vibrations too.

The sound of your cry echoes through me as you take handfuls of my breasts and squeeze. Oh God I want to cum, desperately wanting to cum! I cry out, "Master please please may I cum for you?" "Yes my slave you may cum now, cum for ME!" I feel you empty into me just as my body explodes, convulses, wave upon wave of orgasm rushing over me. Finally, I lay there spent, unable to move, to speak, to even think. I am in a daze, unaware of anything but your body under me still shaking as mine does.

Your voice somehow makes it through the ringing in my ears "You'll need to retract those claws from my legs at some point." I tried not to laugh as I said "As soon as you let go of my tits" Suddenly we were all laughing and trying to untangle as Sean came over with a bottle of water for each of us.

"Aye M'Lady." he said with his musical accent "That was a good one. We shall enjoy watching it many times." as he nodded over to the camera in the corner. Looking around I saw three other cameras I had not noticed when we entered. "Once we get them edited up we should all have a viewing party" Lady Nessa said with a laugh as she noticed the horror struck look on my face.

Garrett reached down to help me to stand as Sean helped Lady Nessa up and then you. We stumbled to the elevator and rode up to the rooftop. There as we walked out was a crystal clear swimming pool and hot tub surrounded by planters full of flowers and trees, lounge chairs with thick blue towels laying over them, a table with an umbrella that had lunch all set out. "Swim, eat or more sex?" She asked.

"All three!" We all replied in unison and laughed again.