Emmys Iron Maiden Glory Hole

It has been a few weeks since Emmy had her way with me at her house. We have a peculiar relationship. We are like the best of friends when out having a drink, as we are now, and then when it comes to sex it is like she turns into a whole other woman and just becomes this wild volcano, erupting lava flow after lava flow of controlling sexual domination. There is no stopping it when you are caught in its path and yet I can't help but to stand at the bottom of that mountain and gaze up adoringly at the heaving summit smoking away passionately, aware that at any moment it may bubble over into another scorching hot landslide that will burn my ass.

We are talking about the last meeting at her house. We don't normally stray into talking about Emmy's alternative sexual life but since she started to include me in this brave new world we can't help but to wander off the beaten track. She asks me about my sexual preferences and why I can't see the contradictions in what I like. I have been wearing stockings and lace panties for a while now to satisfy my sexual desires and have fantasised for years about being fucked in the ass by a strapon wielding lady. Not finding anyone to take up the challenge I bought my own toys and started experimenting with my own anal liberation. The internet and its wonderful infinite possibilities lead on to a further and more intense fantasy to be fucked by a transsexual. Once again I had been unlucky in love with that search. However, I had been lucky enough to get fucked by Emmy and her strapon at her 'surprise party' she organised for me a few weeks back which she had even encouraged me to suck my cum off of.

It was this part in particular we were hung up in conversation about. You see, I had been infatuated about sucking my own cum off of a ladies strapon. I had dreams about sucking the cocks of beautiful transsexuals too. Even convincing crossdressers entered my mind. But that was what Emmy couldn't understand. I wanted to suck cock so badly but it had to be attached to a feminine figure. Emmy argued that it didn't matter what the cock was attached to and that I just couldn't get over the stigma of being labelled 'gay' for having such a fantasy.

"Emmy, look, I get it and I am not concerned with being given any sort of label. I really don't care what other people think my sexual orientation is, I have a strong desire for the feminine look but it's just that I want it to come with a cock," I say finishing my drink and gesturing to Emmy for another.

"Yes please, Humph," she says pointing at her glass. She gives me a look of deep thought through squinted eyes. A look I have seen a few times before and it usually means hugely kinky and dirty thoughts are whirring away in that beautiful mind of hers.

I get the drinks and return to the table. Emmy has a smug grin on her face and she says,

"Humph, I have an idea."

I look back at her with a knowing smile and ask her to "go on."

"I have a friend building me something for a party we have planned next month. I think you would be the perfect person to give it a dry run for me. It should be ready in a couple of weeks. If you are game for it I think you'll love it," she says enticingly.

"Building you something!" I proclaim, "Emmy, you have let me know a bit more than that."

"Humph, have I ever let you down? Come on, I think I can get you to fulfill at least one more of those fantasies of yours, if I can get hold of everyone," she says suggestively.

I nearly spill my drink down my chin, "Everyone! Emmy, I, I don't know," I stammer.

"Oh stop pretending to be shy. You were pressed against my patio window licking your own cum whilst I fucked your ass with a strapon in front of a crowd of people only a few weeks ago. You seemed to enjoy that," Emmy replies wryly.

"I'm not being shy, it's just that you're being aloof," I say, "Give me more details."

"Come on, I know you better than that. You love surprises. This will be one to remember," Emmy says knowingly.

"All right, all right. Sounds fun," I say blankly. I thought the last encounter was 'one to remember' goodness knows what games she has planned this time. I trust her wholeheartedly though and know she won't have me doing anything I wouldn't enjoy. It is for that reason I put my trust in this woman.

"Good!" Emmy says, raising her glass to mine, "I will get in touch when I have it all arranged," she continues as she leans forward and kisses me long and hard on the lips. She always gets close like this when she has something naughty planned for me. It is like I am her sexual play-toy for her to experiment with. Like a teddy bear she can abuse in the garden, role playing games in the dirty mud one minute only to go and wash it all off in a bath and cuddle up to it at night innocently the next.

Ten days go by and I have only briefly spoken with Emmy on the phone twice and had a few text message exchanges but never once have I brought up her 'games night'. But today, Saturday morning, I get a text,

"Humph, get yourself clean inside and out. Put your best stockings on and those lace panties you love and get your sexy ass around to my house for 7pm."

I get an almost immediate twitch in my groin and butterflies in my stomach. So, it is on, whatever on is and it is happening tonight. I text her back,

"Sure! See you at 7pm. I look forward to it."

I get myself showered and shave every part of my body three times over. I clean myself up and douche myself once before leaving the shower and again before I leave for Emmy's. It has been a long anxious wait all day wondering what Emmy has in store for me. My mind wanders back to our conversation prior to the invite and I can't help but focus on the attention she was giving to my claim that I would only suck a cock if it was attached to a woman. I have visions of her tying me up and leading a naked guy over to my strapped down head and getting him to fuck my face. It makes me very anxious as I not only loathe the idea but I have a terrible gag reflex and can imagine him forcing his cock past the point it makes me wretch.

I have second thoughts about the whole idea and I nearly turn the car around at the next junction but I change my mind as I think back to all the other occasions Emmy has taken control and liberated me sexually and I have not been disappointed. I just think of my lace panties and stockings hugging my crotch and thighs beneath my jeans and keep on driving hoping it be something else she has in mind.

I pull up into the drive of Emmy's huge house. I am not sure if I should knock on the front door or go around the back like last time and while I stand there in the driveway deliberating I hear the front door open. It is Emmy, wearing an emerald green corset and fishnet stockings that go all the way up those long, long legs. She looks delectable.

"Hi Emmy, I brought wine, I didn't know what else to bring," I say as I greet her at the door.

"Just your good self Humph, and your sexy little underwear, oh I do hope you are wearing that as I think it will just be so hot." she says looking at my jeans curiously.

"Underneath, yes," I say nervously.

"Right, well lets get them jeans off huh," Emmy says as she starts to unbutton my jeans almost before I have stepped into her house.

Emmy undresses me down to just my shirt and jacket with my stockings and lace panties. She takes my hand and leads me through her kitchen where she hands me a glass of champagne, which is a welcome steady to my nerves. We make small talk as I down the large glass and she leads me once more through the house and into the garden room where everyone was before the last time I was here. I glance over at the patio doors and imagine what that view would have been like of me pressed up against them. We proceed on toward a doorway with circular steps down toward a lower level. My heart is beating like a drum and does so about three times per step as we descend down into a darkened room. I can see a few glowing lights in the distance and a warmer glow coming from around the edge of what appears to be a bar. It is like a nightclub. I can hear music and voices of many people as I am lead around the corner.

"Everyone, this is Humphry. Humphry this is, well everyone, you will get to know them by name soon," Emmy says to a group of scantily clad people all sat around chatting at tables all lit up in neon.

Everyone in the group mouths a polite hello and a gesture in my direction and I wave at everyone back with a nod, my own scantily clad body on show for everyone to see. Emmy leads me over to a table where I recognise a face, it is Suzie from the store where I picked up these stockings. She enthusiastically greets me and kisses me on the cheek. She steps back and takes a moment to admire my attire.

"Humpry, you look fucking hot!" she says exaggeratedly.

Everyone else in the group stops to take more note of my attire and I sheepishly grin and nod as in thanks at all the admiring glances. Emmy comes back and hands me another welcome glass of champagne and proceeds to point at each table and explain who everyone is to me. None of it is going in as she points from person to person, seemingly each girl here with their partner who does something something in finance or something something for a large corporate until Emmy says something that catches my attention and brings my focus back into the room and away from my self consciousness.

"Wait, what did you just say?" I lean over and whisper to her.

"What? Victoria. Yes she is a transsexual. In fact there are a few here tonight, Humphry," Emmy says matter-of-factly.

My cock twinges at the mere thought and my heart is racing once more. Emmy notices my blushing and with a cheeky grin she leans in and whispers to me,

"Humph, I didn't bring you here for you to have your first transsexual experience I brought you here to be a guinea pig for my new device, remember?"

I look at her and try to explain that I know that but without letting her know that I don't know what the hell she means by device. She knows anyway, she can read me like a book and she offers me reassurance it will be fun. She tells me to relax some more and to just get into the swing of things. She takes me over to another table and introduces me to a few people and we exchange pleasantries and after a while I relax and the music and drinks start flowing. I am having a fun time mingling and getting off on all the comments about my stockings and lace panties. Everyone else is dressed amazingly, it is like I am backstage at a burlesque show. And speaking of show it appears mine is about to start as Emmy whispers into my ear that,

"It is time."

I gulp the last of my drink and nod wryly as she takes my hand and leads me toward what appears to be a darkened stage across a small wooden dance floor. Emmy switches on some lights and a huge cylindrical box becomes apparent before me. It looks carpeted on the outside and has five thigh height boxes around its base with spaces between them.

"Ladies and gentleman," Emmy shouts as she lowers the music on the wall panel. "You all know why you are here and now it is time for me to tell our guest, Humphry."

Emmy proceeds to tell me that the cylindrical box is in fact an 'Iron Maiden Glory Hole'. A contraption of her own invention and that I should not be alarmed by it. Something I find hard to believe at this stage with the mention of 'Iron Maiden'. She gesticulates for a couple of men to come forward and asks them to open up the box and they do so splitting it down the middle on one side. Inside it is also made of a plush material and I can see multiple holes now dotted around in two lines. One around waist height and one about head height.

"Humphry, I have a little game for you. You said to me in the pub that you had an overwhelming desire to suck cock and that you could only do it if it was attached to a beautiful transsexual. You even said you could tell by looking at them whether or not they belonged to a transexual or a man. Well, we have five beautiful transexuals here tonight and five smoking hot men and I bet you that you cannot tell the difference between their cocks. I am going to ask you to stand in my 'Iron Maiden Glory Hole' and we are going to close it around you. You will have ten cocks randomly placed through the glory holes and I want you to work at least five of them to completion, the five you think are the transsexuals. Go wild, do what you have always desired with them. When you have finished we will see how well you did and see if you guessed correctly. Are you up for it?" Emmy says loudly to the whole room.

I didn't have anytime to think, I was already being lead toward the contraption and I say to Emmy,

"Of course, how could I say no to you!"

As I stand inside the 'Iron Maiden Glory Hole' Emmy presses a switch on the roof of it which turns on a black light which sets aglow the bright colours of the inside decor. Emmy kisses me on the lips as she helps close the device on me and whispers, giggling,

"Have fun."

The device closes and it feels more claustrophobic than I imagined. The glowing walls help illuminate my body just enough to not be in complete darkness though and I can see all ten of the holes on the walls around me. Five above my head and five at waist height. By my reckoning the diameter of the box is about three feet and I can just about comfortably move about and expand my elbows. I take a moment and a deep breath to contemplate where I am. Just as I get cosy I hear noises on the walls and within a few seconds I can see cocks appear like whack-a-mole at a carnival. Only this time they aren't trying to hide again.

I look around at them all in awe but I have barely enough room to turn now they are all poking in at me. I think to myself that they all look normal, whatever that means. I wasn't expecting to see anything horrific but I am quite surprised that I can barely tell which ones are the men's and which ones are the transsexuals. The challenge Emmy set is at the forefront of my mind though and the thought of half of these cocks being transsexual cocks has me almost salivating. I start to scrutinise each one and think I see one that is for sure a transsexual's and I hesitantly reach up towards it. I slowly and nervously clamp my hand around my first ever cock and as I do I hear a feminine whimper come from outside. I immediately hear Emmy shouting,

"No noises!" as the background music gets louder.

I am convinced I have a transsexuals cock in my hand and I start to relish in this thought and start slowly jerking it back and forth. I move my head and eyes closer toward it and gaze upon its wonder. I start to caress its soft skin with my lips. I begin at the head and then lick the shaft down it's full length savoring the taste and the smells. I am starting to get hot already and can feel myself beading up around my neck. I use my left hand to unbutton my shirt as I continue wanking this beautiful cock with my right just in front of my eyes. I throw my shirt and jacket to the floor and all I am wearing now are my stockings and panties. My cock is now proudly pointing out of the top of my lace underwear and I can't help but to give it a little squeeze as I carry on licking the entirety of this cock in my hand.

I start to quicken the pace some more as I start to feel it twingeing and pulling up against my hand. I open my mouth and hold the head of the shaft against my tongue as I furiously jerk it towards me rubbing it around the entirety of my outstretched tongue. I pull my head back a little to get a closer look at this writhing cock between my hands and I see it start to spurt it's hot glowing white cum all over my face. It initially takes me by surprise but I move in closer for the second, third and fourth spurts to ensure they land on my face. I take a moment to hold on to the cock as it starts to fade and rub its head and the last of it's glorious cream all around my lips. I give it a kiss as I step back. I look down at my right hand as I wipe the spunk from it onto the side of my stockings leaving a glowing streak across them.

I smile uncontrollably for a moment, take a breath and then look around at all the other cocks I see before me. I notice one that looks like mine right in front of me at waist height and I reach out eagerly for it. I start to work the shaft back and forth but with it being in front of me and at waist height it is hard for me to get my hand around into the right and usual position so I turn my wrist so that I am thumb first as I go back and forth down the shaft which feels strange to me. I have an instinctive urge to move my own cock up to my hand in that position and I pull the front of my panties to the side to release my own engorged cock. I take it in my left hand and I place it beside the one before me. They look like twins. I grasp both of my hands around the both of our shafts, pressing them together and start jerking my hands back and forth across their full length.

The sense of having an extra cock in my hands is surreal. It feels like a numb appendage of my own. I keep jerking them, working up a sweat. Uncontrollable moaning noises come from within as I start feeling close to the edge myself. Just as was drifting off into the moment of it all I feel the front of my panties wetten and I look down to see the cock spurting it's hot wet mess over the base of my shaft and balls. I take a second or two to keep pulling at the cock, siphoning off the last few dribbles of cum onto my lace covered crotch.

I start to feel a bit more bold now and I look up to see two cocks, one over each of my shoulders looking inviting and I lean back against the wall at an angle to grab them both at the same time. As I start to motion the cocks in unison I'm surprised to find my ass rubs up against a third cock behind me. This has my cock twitching instantly and I look down at it, the tip of it glowing with pre-cum. I slowly motion my ass toward the shaft behind me and tiptoe my cheeks over it so that the shaft brushes under me, past my balls and between my thighs until my own cock, engorged but drooping from the near ejaculation is touching it head to head. I motion my legs cheeks and thighs back and forth over this third cock, all the while my own cock swinging beneath me occasionally hitting the head of the other as I frantically wank the dual shafts over my shoulders.

I keep going, banging back and forth against the wall. Each bounce I can feel them both twitching in my hands getting closer and closer to ejaculation. I angle them down towards my body in anticipation of their hot loads. As if on cue the one on my right starts to erupt and spurts hot load after load all over my shoulder. I can't concentrate on it to finish it off as I awkwardly try my best to work my left hand on the cock over my left shoulder. I take my right hand, covered in cum from the cock to my right and smear it all down the length of the shaft of the left hand cock and keep sliding my wet and slippery hands up and down it until it spurts ribbon after ribbon of thick and creamy loads all over my chest.

I am now breathing rather heavily from all the hot work and feel rather pleased with myself so I start looking around for my next cock. The one to the left at waist height is bouncing like a springboard and throbbing away. All the others have drooped. I reach out for the eager one and get working its long length with ambition. I raise my left leg up to meet it, rubbing it against my stocking covered thigh as I jerk it briskly. It's long wet load seeps into my stockings leaving a glowing stain as it dribbles down my patterned leg. My raised knee causes my ass to rub up against the cock behind me I had between my legs a few moments ago.

I am in a euphoric high and the beads of sweat are running down all over my back and stomach. I breathe a heavy breath and start to go into autopilot collecting all the cum from my moist skin into the palm of my hands. I reach back and start smothering that cock with the combined loads of all the other cocks. I start rubbing its now sopping wet head up and down my ass crack and can't help myself as I pull my panties aside to place my puckered asshole on to the head of the cum lubed shaft between my hands. I start to push my ass back onto the slippery cock and find myself naturally reach out to the side to steady myself. My hands find two more cocks just to the side behind me and I grab hold of them both with a firm grip using them as leverage to let this third cock between my cheeks slip up into my asshole. As I force my ass back I feel the cock pressing hard against my hole spreading me apart and then slide up into my ass all the way to the wall. I start immediately bouncing off it to work that cock to and fro, in and out of my ass while wanking the two cocks in my hands in unison.