Vegas Twelve to One, Daunting Odds

A group of the masters, led by their host, I didn’t see Sir Michael with them, entered the dungeon and came directly to me. “Oh, do we have a surprise for you. Let’s get you on the cross so we can get started on making another of your fantasies real, Bitch,” says Master.

I am uncuffed. My feet are put up onto the step pads which are about ten inches off the floor. I am set back till my back contacts the center of the cross. My arms are pulled up to the top cuffs that are attached to a ratchet mechanism, and they secure the cuffs to my wrists. Next my ankles are buckled into the ankle cuffs located above the step pads. Two of the masters then crank the ratchets which pull my wrists upward, effectively stretching my body taut as my ankles are held fast. Working together they then buckle all the remaining leather straps that adorn the cross down my arms, up my legs, and across my body, making me one with the cross, unmovable. I strain against my bonds but go nowhere. The hold pins on the pads my feet are resting on are pulled releasing the steps, dropping them away and I am effectively suspended and held to the cross off the floor only by the straps and cuffs.

This is the second time I have been bound to a cross like this. Sir Michael had borrowed one from a local friend for my visit to San Diego. There I was thoroughly abused, primarily by stripping. I survived; I wonder what I will be served here. There was just a short wait to find out.

Sir Michael enters the dungeon, and he has a young lady on his arm. He walks her right up to me. I brought you a present. She is wearing six-inch stiletto thigh high patent leather boots that lace all the way up the front. There is about four inches of sexy bare skin between the boot tops and the lower edge of her pleated mini skirt with a silver studded waistband the barely covers her privates. An under bust corset, topped with halter shoulder straps squeezes her waist and causes her cute little exposed breasts to thrust forward. Over the elbow gloves adorn each hand and arm. A newsboy flat cap also with silver studs accents her darling bangs and shoulder length dark brown hair. She completes her ensemble by sporting a matching riding crop in her hand. All of these garments and accessories are made of sensual black leather. She is hot. Oh wow, is she hot. As presented, she is also the spitting image of the character Tiffany Chester, a dominatrix on the cable TV series ‘Bonding’, played by Zoe Levin, who is a 5’5” slender, champagne glass busted, very attractive actress. They could be twins.

I am very unsure about this. My contact is explicitly clear, I’m not to have relations, force or not with women. That crosses my morality line. I know it’s a weird line, but that’s where I have decided is as far as I will go. Sir Michael is well aware of this, he is good friends with my wife, I don’t get this, he brought her in. OK, I’m slow on the uptake. New to the contract was a clause about transgender women. No, this couldn’t be. To me, this person is genuinely sexually attractive, desirable, gorgeous. Someone if I was unencumbered, I would want to meet, well more than just meet. And wow, how she is dressed is a super turn on. This couldn’t be a man, could it? I look hard down at her skirt. All is still covered for the moment. I’m confused.

She makes sure I get a good look at her. In a very feminine voice she says, “Hi sweety, you sure look good up there. I love that cock of yours. I’ve been looking forward to playing with you, it is why I came. You’re going to make me a happy girl tonight, aren’t you? Don’t let me down. I read in your journal that you like to be striped when you are on the cross. Well, I’m good at that so I guess you’re going to get just what you enjoy. But first let’s check out your tool, he likes to experience pain too, doesn’t he?” And I am introduced to her riding crop. She hits my cock three or four times. It has gotten a little swollen, thrilled about the outfit that she is wearing. It is as much of a turn on as is this attractive woman. “Oh, isn’t that nice, I think he’s starting to get excited that I’m here. Look, I’m glad to see him too,” and she lifts her skirt and show me and the rest the boys her erect penis.

And I am so relieved she has a dick, even so I still have an unsure conscience. None of the other men made my cock rise like this.   

She is not done yet with her crop and makes it dance on and around my nipples. I’ve been whipped by many this weekend, but no one did it with such a sexy sway, almost dancing on her stiletto heels and toes. She switches back to my balls and cock. After a few hits, she raises one of her thin leather clad legs and rests her point heel against my bag. She is gentle. “Don’t worry sweetheart I won’t hurt your precious balls and cock; I want to play with them later, so I don’t want anything broken. I just want you to admire my boots, I wore them just for you, princess.” She removes her heel and adds, “Now let’s see how good you look in candy strips. Who has the single tail?” she says to no one in particular.

My concern and thoughts about my excitement from this person is lost as stinging shoots across my chest. Owww. Then another. Owww. And again, and again. Owwww. “Quiet, my darling, or I’ll have the boys gag you.” I hold my breath in anticipation of each next hit and when it comes, I gasp, then suck in air again and hold. The stinging is not severe, it’s however just within the upper end of pain/pleasure. Certainly bearable. This stinging, not nice, but different from the other whipping I’ve endured. I notice as she travels up and down my chest, stomach, and thighs, she makes sure strips clearly include my nipples, but my balls and cock are spared. The body acclimates to the assault after a while, and I no longer seem to wince as the strikes land. Well, other than when she hits my nipples, and she never seems to miss them as she travels up and down my body. When she is finally satisfied that I am well colored in long red streaks she puts down her weapon. She then soothingly applies Witch Hazel over everywhere she has laid down strips. This burns initially, especially where the stripping was heavy, but soon turns to a soothing feel. One would say it was applied lovingly, not what I would expect from a dominatrix. But then, she has not been belligerent or harsh in her approach to me. She’s more of a deviant tease.

“I want to see how big my sweetheart’s dick can get, that OK with you?” she asks Sir Michael who is passing by. And with his nod to the affirmative, she starts with a gentle fondling with her leather gloved hand. The leather on my privates provides a blissful, wonderful stimulation, much different from an uncovered hand. This is quite enjoyable but doesn’t come close to what she begins to do with her tongue. The first lick sends a vibration down my spine. She works both in combination, using her glove to concentrate on my sack as she consumes my now grown shaft with her mouth. She provides the perfect combination of pressure, warmth, and wetness. Between her varying tempo, ball play, sucking and deep throating, she is making me go wild.

Visually I am going nuts too, I gaze down from my bound stretched cross at what from my vantage point is a beautiful leather clad women worshiping my raging cock. There is a warm, pleasurable sensation running through my entire body. This mouth is amazing. She is making me squirm, I am straining against my bonds, the feeling, there is nothing else like it. I’m even tingling in my head. Her mouth is doing so much more than a vagina could do. She is pulling the life forces out of me and I am getting close to a climax. I don’t have and won’t be given permission, I try to pull back, but my body is mostly immobile. She senses the nearing discharge, and slows it down quickly, and then retracts. “Good boy, you hold that cum for later, we have lots more playing to do.”

Oh, did I want to cum. That was fantastic, certainly I didn’t feel submissive. But my mind is not happy with me. Yes, I am bound and couldn’t resist, and yes, I know she has a cock, but on the other hand, I was thoroughly aroused and shouldn’t be. “You tasted good, sweety, you may not have ejaculated, but I did love your pre-cum. And you’re my perfect size, not too long, not too short, not too thick, not too thin, just right. Yeah, that’s right, I’m Goldilocks, and I have a bed that’s just the right size for us too.” I know I didn’t contribute anything to this other than being there, providing her a defenseless rigid cock, but I still liked the praise, especially in reference to my equipment size.

“Hey, you done with him on the cross? I want to do him on the bed,” asked Mistress. “Well, we wanted to make him sparkle in the dark before taking him down. Is that OK with you? said one of the masters. “Sure,” she replied. Sparkle? What the hell is that? I was about to find out.

The lights in the are turned off. It is very dark. I am still strapped tight to the cross. I see two neon tubes light up, one each held by two of the masters. I had never been subject to electro play with a violet wand and I feel my body tense up in anxious anticipation. One device looks like a glowing rake, the other like a neon round spiral. The first one used is the spiral, where it is moved in small circles around my right nipple, held close to but not touching my skin. It gives me a buzzing sensation, like gentle effervescent bubbles tingling as the wand glides across my skin. I didn’t know what to expect, this is unique, different that the other electro play, both the pleasurable and not so pleasurable play I had previously experienced. You can hear a quiet buzzing sound also. This is quite intriguing. There is a beautiful violet electrical glow playing over my skin. The deep purple neon light sparkles in the darkness. I’m experiencing teasing pain in color. It now feels almost like prickly tickling. He expands his exploration with the wand to my other breast, then most of my chest. As he moves to my privates the tingling feels more intense there, getting more like a static shock you receive when you touch a metal doorknob. There are oohs and aahs like you hear at firework shows, it is captivating my gathered audience as he glides over me. I’m putting on a well-rounded show for them as my body begins to buck at the unpleasant irritation of my sack.  

The second wand is now brought into play. This one is even more intense, more painful in the pleasure/pain scheme of things. The current stays near my skin surface and doesn’t penetrate deeply into my body as regular electro play does. The rake is adjusted and now the intensity is getting close to the feel of a sharp knife combing across my skin. Despite the pain it is causing me, the purple neon color dancing across my body in the darkness has such an artistic play in my mind I am able to endure this and even enjoy it. So are the watchers, they are still enjoying the show. The raker adjusts the tone down a bit and it moves closer towards the pleasure range, an acceptable pain/pleasure level. He explores my entire body, while the spiral wand holder is now concentrating on my balls and cock. The audience has seemed to grow as I hear even more oohs and aahs from the gallery. I’m a miniature lightshow, real entertainment as advertised. The show isn’t overly long, but the players want the ending to be memorable to me and the crowd, so the spiral is turned up and placed very close to my erect nipples, providing bright colorful sparks between the wand tip and my nipples. I screech out and buck at my bounds at the unexpected and sudden concentrated pain, receiving approving applause from the gathering. This is a group who likes to see strict bondage coupled with abuse and suffering, this time with a little color and artistry. They got what they came to see.

As the lights were brought back on, they released me from the cross, a welcome relief to my shoulders and arms which had begun to ache and cramp from their stretched upward positions. I am moved over to the bed as previously requested by the Mistress. Here, I am bound on my back in the center of the mattress with my arms spread to the mattress sides, wrists cuffed in leather and secured to the bed sides. My legs kept together, ankles cuffed also in leather and then stretched to the bed’s tailboard and secured. A collar with D-rings is added to my neck, and it is tied off to the headboard. All bonds are snug but not so taut that I still have just a bit of movement of my limbs and neck, I can even spread my legs a little. 

My leather clad Dominatrix parades in front of me. She makes sure I get a good look at her again, and then she bends over and gives me a gentle kiss on my cheek. She climbs up on the bed and straddles my chest with her leather boot clad knees pressed up tight against my armpits. She leans forward so her dick presses against my lips. “Now it’s your turn to do me,” she says. I open my mouth, and she leans into me further, so her erect dick slides into my mouth. I go to work, this time without a ring gag inhibiting me. Much to my shame, I preform more enthusiastically than I have with anyone else who has had their cock in my mouth this weekend. As I begin to service her, I close my eyes and think about the long shiny black high heel boots laced all the way up her slender legs that are now pressing against my faced while her short, flared leather skirt drapes over my head. I use what neck movement I have to help glide up and down her member, with my lips tight against the shaft and tongue licking her shaft, slit and head. She starts gentle thrusts as she moans and gives praise. I open my eyes to look up and watch her little titties that are jutting out from her corset sway as she works her hips over my mouth. My mind is making me perform as if this is a pussy I am licking and sucking. Dangerous and wrong. I think I may have an erection or at least one is stirring. Risky, shameful. She has good control of her own excitement and makes me blow her for a long time, with her constantly indicating pleasure and satisfaction without climaxing.

She finally decides I have serviced her dick enough and withdrawals it from my mouth, then spins around and says, “OK, sweetheart, please lick my crack and I’ll get you properly hard.” With that she pushes her petite butt against my face as she bends down and takes my cock into her mouth. I somewhat reluctantly go to work with my tongue up and down her crack, ultimately finding her hole as she gives my penis the quality attention she had delivered before. I am rock-hard within a minute. She has accomplished what she wanted. “OK, he’s wet and ready. Now Princess, you stay hard as I want you to fuck me good. Don’t fail me, I have friends here that will make you very unhappy if you don’t treat me right.”

She swings around, and now facing me as she staddles my waist and drops herself down on me. She wiggles around a bit, reaches her hand under her legs, finds my dick and guides it to her hole. Being an expert at this she is able slide down onto my shaft, swallowing it up with her ass without effort. She goes slow as my dick is lubed only with her saliva and she has a tight butthole, but she does now have all of me in her. She pulls back up, then slides back down again. My man-on-man ass fucking virginity has now been lost. While I have experience dick in my butt, this is the first time my dick has been in another man. Yes, I have been in my wife’s butt a few times over the years, but this is different, a new category. Initially, Mistress is doing the work as I am almost in a state of shock at what is happening and of course I am tied to the bed. Her tight clenching ass is keeping me hard. She begins coaching, giving instructions and I obey, doing what I can, bound as I am, to thrust my waist upward and rotate slightly side to side. She bounces up and down, sometimes fast, mostly slow. It is marvelous, she is so tight, the grip of each rise and fall creating fireworks of ecstasy. She seems to be able to clench and release it as she moves. She slows every few minutes to let my excitement calm down, but my mind’s vision of her outfit, her beauty, and my bounds keeps me wrongly over-stimulated. I try to think of things to distract me, it should be easy, but it’s not working. Even thinking about the moral dilemma doesn’t help because she is that good at what she is doing and that hot. I remain rock hard within her tight hole. She at times rest on my groin and just wiggles side to side, then leans forward and back, almost gyrating on my cock, then it’s back to rising up and down. She brings her chest down to mind creating a new angle that stimulates me even more. Her tits are tantalizing my chest as she rubs them against me. Her ass playing havoc with my cock. Her moans are so feminine sounding. She arches her body further up, moving her breasts to my face and she says, “Suck my titties.” I have years of practice at this, and I lick, suck and kiss her nipples doing all the tantalizing tongue and lip actions that I know will excite her. She moves her right breast from my mouth to her left and back again numerous times providing praise words that indicate I’m talented at nipple stimulation. Then it’s back up right again with her rubbing circles with her fingers around her now rigid teats as she continues to fuck me. And she is fucking me, even though I’m contributing some, she is making this happen. I was able to hold on for maybe seven to ten minutes, but when she starts a new round of deep penetrations she reaches down and starts twisting my nipples, and I can’t stop it, I ejaculate with great force into her butt. She knows immediately, and gleefully squeals while wiggling her butt after squatting down tight against me and says, “You were fantastic, I loved that, but you’ve been naughty, so very naughty. And I think you know it. I hope it was worth it because you know you’re going to suffer for that pleasure.” Oh crap, she’s right.