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First Time

12

"So, that's you booked in for tomorrow evening at 6pm. You have my address and phone number already. I would suggest that between now and then you refrain from touching yourself at all. Just so that we can make the most of it tomorrow. Any other questions?"

"No", I replied "I'm looking forward to seeing you, if a smidgen nervous as well."

"Don't you worry about that" she said, "within 5 minutes of you getting here all nervous will have long since been forgotten. Goodbye until tomorrow"

And with that final remark, Miranda put the phone down. I sat there for a few minutes not quite sure what I had gotten myself into. My first time with a transsexual, and it felt rather like going in at the deep end. I pulled myself together and started planning out the various things I needed to do between now and then. It was all rather dull logistical bits; making sure I was suitable shaved, getting cash out, and trying to find if I had an envelope of some description in my normally paper free apartment. I figured keeping busy was the best way of keeping my mind off things. My biggest worry was how I was going to get to sleep tonight without a nice pacifying wank to calm my nerves and aid my drifting off into blissful slumber. I'd been putting off making this appointment for far too long. In turn it had built up in my head to such a huge event that I'd had to redial the phone number twice to make the booking, due to my hands shaking so much and my brain struggling to concentrate on the task in hand. The couple of fingers' worth of Johnnie Walker I'd had for some Dutch courage had probably contributed too.

As expected that night I seriously struggled. The combination of nerves, anticipation and the scorching heat of summer made sleep seem almost impossible. Having gone to bed relatively early to try and make sure I was well rested, it was gone 3am before I finally drifted off to sleep. In between I tossed and turned, perspiring freely even though the duvet had long since been cast aside, leaving me in nothing but boxers. As a looked at myself in the half light, I couldn't help be critical and wonder why I'd not put a bit more effort into keeping myself a bit trimmer. I wasn't obese or anything, but it wouldn't have taken superhuman efforts to get a bit of muscle definition going.

Thankfully I slept in late. It was a Saturday, so there was no pressing need to be up early, and the few jobs that needed doing were not going to take long. After a cold shower to cool down, and a trim of the hair round my cock, balls and ass crack, I dried myself on a towel and got dressed. After that I drove into town, and withdrew enough cash for the evening. Given the amount, I'd had to go into the branch and withdraw the money over the counter. When the teller asked what it was for my brain went into a flat spin. Eventually I managed to blurt out "Birthday present", which I'm not sure the teller entirely believed. Money retrieved, I beat a hasty retreat and headed off to a stationers to buy an envelope. It seemed excessive to be buying a whole pack of envelopes given that I managed to avoid them in all other areas of live. But Miranda had made it clear that was how she was to be paid. I spent a while wandering around town just trying to kill time. I tried eating some food but just wasn't hungry, quite an unusual state of affairs for me. After what seemed like far too long, the time to head over to Miranda's came round. I pulled the piece of paper with her details on it out of my pocket, and put the address into the sat nav in the car. 20 minutes drive away, which timed things about perfectly.

Miranda lived a little way out of town, on a very quiet country lane. The house had clearly been around for a while, but had been well restored in recent years. Pulling up the driveway, I quickly chewed on a breath mint, took a deep breath and got out of the car. I knocked on the door and Miranda opened it. I almost immediately breathed a sigh of relief as I took in the sight of her. I'd read far too may horror stories of bait and switch. Miranda looked lovely, with long fiery-red hair flowing down to below her shoulders and alabaster skin adorned with freckles round her face. She wore a long fitted dress that was a riot of rainbow colors, and from where I was standing, it looked like not a lot else.

"Would you be Paul?" she asked.

"Yes I am" I replied, managing to keep any trace of stammer out of my voice.

"Well then please do come in. Given the rather incredible weather we are having, would you care to take a shower to cool off?"

"I was just about to suggest the same thing myself" I laughed.

I stepped through the doorway and Miranda leaned in and kissed me full on the lips. I was slightly taken aback as the kiss caught me by surprise, and it took a moment for it to register before I could respond and kiss her back on those soft lips.

"Ooh, nice and minty fresh" she commented, "I do approve of that. Now, follow me and I'll show you to the bathroom. Once you're finished in here, I want you to go to the next room down this hallway and I'll be waiting for you."

As she turned to show me the way, I surreptitiously dropped the envelope onto the small table in the hallway as had been requested. We went up the stairs and she ushered me into the bathroom.

"Feel free to use any of the soaps and lotions etc that are here, and towels are in that cupboard. You can also leave your clothes in here when you come through to my room."

Miranda winked at me and then closed the door as she let herself out. I quickly removed my clothes and got myself into the shower. The head on the shower was huge and let down a glorious cascade of water onto my skin. Quickly enough I was scrubbed and refreshed. The towel was huge and soft, and I wrapped it round my waist as I padded down the hallway to her room. I've no idea why I felt the need to cover myself given what was about to happen, it just seemed the somehow right thing to do to my overloaded brain. Miranda was sat on the bed, still wearing her figure hugging dress. There was no sign of what lay hidden inside it. She looked me up and down, her piercing green eyes appraising what was in front of her. Whatever her thoughts were, she gave nothing away.

"So" she said, "You gave me some fairly developed ideas in that email you sent as the first point of contact. Are you still keen for all that to happen?"

"Yes" I replied, "I've spent far too many years simply watching that kind of thing on the Internet. I just have to know what it is like to experience it for myself".

"Very well." She stood up and crossed her arms in front of her, pushing her fulsome breasts up. "I want you to get rid of that towel first and let me get a proper look at you."

I slowly undid the towel and let it drop to the floor at my feet. My cock hung somewhat limp.

"Please bear in mind I've just had a really cold shower" I said.

"Oh good" she replied, "I was starting to get rather worried for you for a second there."

She ever so slowly circled round me, her eyes roving up and down my naked body. Around the rear, she gave my arse a gentle swat, which made me jump.

"Now then my dear, no need to be so nervous, you're going to have a marvellous time, I promise you. Now, hop onto the bed and lie in the middle on your back. Well start off getting you properly restrained as requested."

She'd already removed the duvet from it. There was just one set of pillows in the middle by the head board, the only items on the pristine white sheets. I lay down on my back, and rested my head on the pillow. Miranda walked over, took my left leg and moved it so that it pointed towards the corner of the bed. Her hands were cool and dry on my skin, and just that brief touch made my cock start to fill up. She pulled out a leather cuff out that attached to a chain, and wrapped it round my ankle, securing it tight with the buckle. She then repeated this with my right leg, and my cock started to show visible signs of arousal now.

Finally she came round to the head of the bed and attached a set of smaller cuffs to each of my wrists. I had a little movement at this point, but it was no more than about 2 inches on any one limb. As she walked back to the foot of the bed, she dragged her nails down my side and on down my leg. She skirted round my cock, which still flexed in anticipation. She chuckled when she saw it.

"Well someone seems quite excited about what's going to happen, hmm?"

"Oh yes Miranda, I've never felt so excited in my life. You were right about all the nervousness vanishing."

"Excellent, let us begin then"

Still fully clothed, she knelt on the bed between my legs and slowly leaned forward, stretching out until her face was mere inches from my own. She stayed motionless for what seemed like ages as she looked straight into my eyes. Ever so slowly, she leaned forward, and closing her eyes, kissed me once more on the lips. I closed my eyes too and just enjoyed the feeling of her lips on mine. Her tongue parted my lips and she slid it into my mouth, searching for my own tongue to play with. Still lying on top of me, we kissed like this for several minutes, my cock straining under her stomach. She reached down a hand under herself and gently stroked up and down a few times on my cock.

"My, he really is a handsome chap, isn't he" she cooed. "I can see i'm going to have quite a lot of fun with him."

She knelt back up on the bed, leaving my cock standing bolt upright. She pulled each of the straps of her dress over her arms, and gradually exposed both of her breasts to my greedy eyes. They were large and beautifully pale, and hung there pertly without a hint of sag. The top of the dress continued down until it gathered around her waist. Her stomach was taught and flat, but not overly defined. Just perfect for me.

"Close your eyes" she told me, and I did.

I felt her shift her weight slightly on the bed. I then felt her breath across my cock as she blew on it genuinely. Again, it twitched and bounced in response, and once again I heard her giggle at it. There was a pause for a moment, and then I felt a warm, moist sensation as she gently licked the top of the head. This time my whole body shivered in anticipation. A nail was dragged up it from the base all the way up the underside of my cock, then round and round in circles once it reached the head. I was tensing all over by this point, desperate for a more solid connection. I kept my eyes clamped tight shut, as anything less would have been too tempting to peak through.

Finally, I felt her mouth wrap around the head, and her tongue start to flick over it again. Gradually she lowered her mouth down until I reached the back of her throat, and then she withdrew again. She bobbed her head up and down a few times, each time getting to just before her gag reflex and then withdrawing again. I started trying to hump upwards with what little movement I had, but she just withdrew entirely and knelt back on her heels again.

"All right, open those eyes again" she instructed.

I opened my eyes and gazed at her as she knelt there. "How are you doing now then?" she asked.

"Jesus Christ I'm horny" I blurted, "I don't think I've ever felt this horny or desperate in my entire life".

She grinned at me, a huge smile of delight spreading right across her face. She stood up on the mattress, and turned away from. Teasing, she bent forwards and started moving the dress down from her waist. Gradually, more and more of her beautiful buttocks came into view, each cheek looking shapely and inviting. She kept her legs pressed tightly together as the dress reached her feet. Straightening up again, she took one foot out and placing it on the bed behind, used the other to flick the dress off the bed. I had been right; she had been wearing literally nothing underneath. I let out a whimper.

"Oh my, whatever’s that matter to produce such a sound?" she inquired.

"I just want to see all of you, and you are driving me completely to distraction".

"Oh really, which bit of me are you so keen to see?" she cooed

"Your cock, I'm absolutely desperate to see your cock and what I've let myself in for" I replied.

Once again employing infuriating slowness of movement, she turned herself round until she was facing me. It was large. Comfortably larger than mind in both length and girth. The end had been circumcised, and her head of it jutted forward, as if pointing directly at me.

"You know what comes next, don't you?" she said.

I nodded weakly. Placing a foot either side of my chest, she slowly knelt down again, this time pinning the tops of my arms under her legs. Now I could see her cock in minute detail, inches away from my face. Every vein and ripple on the surface as clear as daylight.

"I want you to open your mouth and stick out your tongue for me" she ordered.

I complied, opening wide and sticking my tongue out as far as it would go. She brought the head of her cock down until it it was just touching the tip of my tongue, then started to slide it around my tongue in a circular motion. Then she paused.

"Your turn" she said, "I want you to lick my cock in a manner befitting the most wonderful thing you've ever had in your mouth. Oh, and by the time we're done here, you'll have taken the whole thing in your mouth, so you'd better learn how to deep throat real quickly."

I brought my head up and my lips enveloped her cock. I swirled my tongue around to get used to such a novel sensation. The merest hint of pre-cum had oozed out of her tip, giving a slightly salty tang to it. As best I could from my restrained position, I tried to lift my head up more to get her cock further into my mouth. I could feel her head right at the back of my tongue, but there was still about 3 inches to go. I simply could not get my head to go any higher with my arms tied to the bed posts. After a few minutes of my bobbing my head up and down, desperately trying to get her cock deeper, she pulled back and pushed my head back onto the pillow, freeing herself.

"Looks like you're having a bit of difficulty with my little deep throat challenge, aren't you?" she said.

"Yes, I cannot get my head any further forwards to take the last few inches."

"Would you like me to help with that?"

"Oh yes please, your cock is wonderful and I so desperately want to be able to take it all the way in."

"Very well, I will assist with your deep throating of my cock, but be warned, I'm going to fuck your throat like there's no tomorrow." Before I could reply, she grabbed my head with both hands, leaned forward and pushed her cock hard into my mouth. It went right past my gag reflex and I nearly wretched. I looked up to see her eyes looking straight at me. Without breaking eye contact, she firmly and surely kept on pushing her cock down my throat, until I felt my nose touch the base of her stomach. She held it there for a moment.

"Can you breathe at all?" she asked.

With extreme care, I shook my head back and forward, just enough movement to confirm that I could not breathe at all. She pulled back until her cock had left my throat, but still left a couple of inches in my mouth.

"I'm going to properly fuck your throat now, not just hold it there. You'll want to take a deep breath before I start."

I inhaled as much air in as possible, and then she proceeded to push her cock back down my throat. Back and forth, her hips pushed up against my face with each oncoming thrust. My eyes starting to water as I did my best to open my throat and allow her cock free passage into me. After what seemed like an age to someone holding their breath, but probably no longer than 45 seconds, she pulled back out of my mouth completely, and I gasped in lungfulls of air.

"How did you like that then my little slut?" Miranda asked.

"I've never experienced anything like it. Frankly I expected it to take the edge off my erection, but my cock is still absolutely rock solid. It makes me feel so dirty and used, I love it."

"Well in that case, we're going to do it again. Open wide."

With that, she inserted the head of her cock back between my lips, and then pushed all the way down the back of my throat, holding my head in place with her hands so that I couldn't withdraw.

"I want to to stick your tongue out and lick my balls like this" she said.

Straining as best I could, I got a bit of my tongue past my lips, and licked at whatever of her flesh I could get access to.

"Oh yes" she murmured "lick my balls, lick them, lick them, lick them".

Eventually, she withdrew her cock from my mouth, and sat back on my chest.

"Now, I'm going to deviate a little from your written instructions, to something you didn't ask for, but that I really enjoy. I'm going to turn around, and sit on your face, and you are going to put that tongue to good use by burying it right in my ass."

She stood up, and from the angle I had she seemed to tower over me, her cock and breasts thrust forward defiantly. She turned, and placed a foot either side of my head, before lowering herself down to a crouch. I could see her rosebud just an inch from my mouth.

"Kiss it" she ordered, and I lifted me head and kissed each of her cheeks in turn. There was a resounding slap on my cock in response.

"Kiss my arsehole, not my cheeks. That was not what I told you to do."

My cock stinging as a result of the slap, I buried my face between her cheeks and kissed her right on target.

"Now your tongue, I want you to start pushing it in there".

I made my tongue as rigid as possible and slowly started trying to work my way in, pushing and wiggling it around to get a bit further in. Without any warning, Miranda shifted her position and sat down firmly on my face, my tongue lodged inside. I kept on pushing and licking as best I could, whilst she reached forward and started playing with my cock, jerking her hands up and down on it. I could barely contain myself and started thrashing my hips trying to gain some more traction on her hands. She immediately withdrew all contact.

"Boys that cannot restrain themselves need punishing" she announced.

I felt her weight shift on my face as she leaned over towards the bedside cabinet. I wasn't paying much attention to what I could here, as I finally got a few breaths of much needed air into my lungs. She settled herself back down on my face so that I could resume my ministrations to her frankly glorious behind. Suddenly I felt a sharp pain in my right nipple, and I strained at my bonds. She laughed and told me to quit moving around so that she could finish what she was doing. Moments later, a similarly sharp pain in my left nipple occurred to balance things out. She leaned forwards to go back to her ministrations on my cock, and for once I could breathe again between bouts of licking and burrowing. The pain in my nipples was quite intense, but I couldn't see what was causing it. After a while of her attention to my cock, I was getting seriously close to completion. I couldn't help but buck against her hands again. Once more she withdrew her hands, leaving my cock humping against the thin air.

"You really don't learn, do you" she said, and reached down towards my nipples again. All at once the pain in my right nipple ratcheted up and I let out an audible moan. The same happened with the left one, the pain making me near delirious with pleasure. I knew I'd said in my email that I liked having my nipples pinched, but this was a whole new level of pain for me.

"Oh there's going to be plenty more pain for you my dear" said Miranda, and she stood up again and climbed off the bed. She stood there a moment surveying her handiwork; my cock that felt full to burst and my extremely sore nipples. I could now see that she'd attached some clamps to them, with teeth on that were biting into my soft flesh. No wonder it hurt as much as it did.

12
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