My First Feminization Pt. 01

Today is the day. The day I finally find out what my gift is, what I've been earning for the last 3 months. She assures me I will thank Her. That would be more comforting if She hadn't tacked "At least, by the end" to the end of Her thought. She has never been wrong before, however much I have feared or longed for a new activity, She has always chosen wisely. Always made the experience unforgettable. My cock hardens as my mind plays through some of our previous sessions, pressing almost uncomfortably against my jeans.

I am taken, unable to see, into a room. A hood covering my eyes, but leaving the rest of my face exposed, and my ears free. I feel hands, pulling my clothes off me, I'm not sure how many, it feels like hundreds, until I am left standing naked, cock hard and throbbing, not knowing what, or who, comes next. I am told to spread my legs apart where I stand, and I feel cold against the skin of my legs, my balls, down my arms, again, all those hands, but this time, I realise, shaving. All body hair below the neck is gone. I'm left standing, shivering just slightly, naked, hairless, and a little unsure. I make the mistake of opening my mouth to ask who is there; less than half way through the sentence I am grabbed and a ball gag forced between my lips and secured tightly behind my head.

More hands. Dressing me this time, I'm guided into silk panties which would have been a nice fit, if my cock wasn't so hard. Then a mini dress, tight, binding my aching cock to my body; it was slippery so I'm guessing latex, lubed for wearing. Abruptly seated they push my feet into boots that slide up my legs, and up over my knees. Thigh-high boots, nice, my favourite, though I'm not usually the one wearing them. Then brushes, lip balm, powder on my cheeks, my eyelids.

Heh, lip balm, that was lipstick, my makeup is being applied. Sudden pain in each earlobe as earrings are clipped on. Did I really agree to all this?

Pulled to my feet again I discover the boots have heels, which makes me unsteady, but still standing. Something encircles my waist, then my wrists, clipped to my waist I realise I can no longer move them. Something is pulled onto my head. The sound of the chair being dragged away fills my ears and I am left standing, somewhere, in high heel boots, silk knickers, a dress which I hope is a sleek red one, then pause to wonder when I decided looked good in red, nevermind a dress? The straps of the dress leave my shoulders exposed, but there's something brushing against them as I move my head. A few more movements and it clicks, it's a wig. I take a deep breath. She said it would be the most exciting thing we'd done, but hadn't mentioned this...

I remain standing for what feels like an eternity. I can hear people moving around the room, whispered talking. Feels like I'm on show, though to how many I don't know, maybe no one is watching me at all.

There's a hand on my right thigh, then another on my left, pulling me forward. I shuffle awkwardly, these heels leave me unsteady. Then warmth against my aching cock, fingers slipping under the dress, pushing it up, reaching my cock and freeing it between panties and dress. The previous warmth is quickly revealed to be a hot wet eager mouth that engulfs the tip of my cock. Their tongue plays across the head before my full length is sucked in and a frustratingly slow pace starts, my cock sliding in and out of that talented mouth. I attempt to lift my hands to pull their head, wanting to increase the pace, force my hard cock down their throat. A whimper falls from my lips as I rediscover the cuffs holding my hands at my sides, and realise the heels prevent me from controlling any pace with my hips - falling over would end it real quick! My last hope is to beg for more, for faster, to stop teasing my poor cock and let me cum. The gag puts a quick stop to that, leaving me a whimpering moaning wreck as the teasing continues, feeling so damn good, but not quite good enough to take me over the edge.

In the back of my mind I wonder who it is. The control shown is exquisite torture that says it is Her mouth, She knows me so well, but the technique...it's new, no hands, just mouth, tongue, lips. Perhaps it's one of the audience. Am I to be passed around the crowd? Is there a sea of women wanting to suck and fuck my sissy self? My legs start to tremble slightly, the blowjob is keeping me right on the edge, thoughts of being used to service several women thrilling and terrifying all at once. For FUCKS SAKE I WANT TO CUM!

Abruptly the blowjob stops and I hear a voice in front of me, below me, saying "I did good, right? You'll let me cum now?" it occurs to me it sounded low because they were on their knees. The voice continues "Please? I did good! He didn't cum, just like you said!" moving as if the person stood up. I can feel my cock still throbbing, still dripping, still aching.

I suddenly realise that voice, that blowjob, that mouth, the delicious, talented, frustrating mouth belonged to a guy. As he walks past me, still begging someone for an orgasm, I hear earrings jingle, just like the sound in my ears when my head shakes. The truth hits me in the chest, robbing me of breath - he was me. A guy whose Mistress has sent him here to be feminized and used - for the entertainment of the crowd, presumably.

I've been a sissy before, She has pegged me into next week while I wear Her stockings, had one of Her girlfriends suck me while She watches, but this ... this is new. Never before a guy, never a *crowd*, never *alone*, but the biggest shock? That it was another sissy; that I so nearly came in the mouth of a guy who lovingly sucked my cock, knowing that has made it so much hotter, so much more appealing, so much *better*... I've had 'ruined' orgasms before. She loves to tease me to the edge and let go, just to see how close she can get. Sometimes we go a little too far and the cum dribbles from my poor deprived cock.

Today, however, as I realise just who had my cock, just what I might yet have to do... the cum starts to dribble from the tip of my cock. A fully ruined orgasm of delight as my mind plays through what the evening may yet bring. I'm barely aware of some laughing in the crowd. Some of them have noticed the guy teetering on his heels, otherwise standing alone, cock out, moaning into his gag at the almost pleasure of a ruined orgasm and dripping onto the floor, or his boots, or whatever is close. Then panting for breath, flushing red with a touch of embarrassment as he realises just how turned on the idea of servicing a bunch of sissy's makes him. As he realises She was right, this is going to be the best ever, as a once believed hard limit melts away.