Amateur Dramatics Night Ch. 01

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My rectum seemed to be squeezing as if trying to suck anything inside; to refill the hole and to continue where Paula's penis had left off and it wasn't to be unfulfilled for long!

Sam was up and round behind me in a flash, his penis already drooling precum as he moved and it took but a short time before he was kneeling behind me where Paula had been, his penis already pressing against my body.

"Won't need any lube," he said, "Loads of lovely sexy cream to slide on."

"Dirty bugger - get on with it!" said Paula, chuckling, as she came and sat beside me.

"Just getting ready," said Sam who seemed to be hesitating somewhat.

Ah - his first fuck - no wonder he was perhaps a bit scared - and Paula understood too. She was up off the settee in moments and was soon behind me too.

"Ooooh God, that's nice," I heard Sam moan.

"I'm just guiding you," said Paula, "Concentrate on his hole."

She'd obviously got a good hold on his cock and I soon felt the end sliding into my welcoming hole; my already stretched, lubed and ready hole.

"Ok, now just push steadily," Paula said and I felt Sam's penis sliding into my anus.

"Ohhhhhh," groaned Sam as he felt my hole accept and absorb his cock.

"Yesssss," I groaned as I enjoyed the pleasure of a second cock inside my arse.

"Ooooohh, that looks gooooood, makes me feel all hot," said Paula, "Keep pushing, all the way!"

I felt Sam's penis slither deeper into me, lubricated by Paula's cummy deposits, then he began to move his cock around, in and out.

"That's it, take it easy to start," said Paula, "Let the feelings come to you; his hole will start to squeeze your cock and you'll soon find things start to get exciting."

I knew what she meant; and after I'd become used to the invasion of this second column of penile flesh I began to work my hole; squeezing and sucking at his cock with my muscles as my body strove to extract his stock of spunk.

My hips began to squirm and thrust back at him, all without conscious thoughts impeding my body's reactions; my hole wanted his offering, his spunk, and was doing all it could to encourage his penis to unload.

Sam was now starting to get worked up; his hips were thrusting faster and harder now; his first ever male fuck was hardly likely to last all that long but so long as he enjoyed it to the full then so what.

Let him cum!!

"Yeah, yeah, yeahhhhh," moaned Sam as his thighs slammed into my buttocks, "Feels good, getting better, getting nearer...oh fuck, yeahhhh!

He was panting hard now as he neared his climax and even I was getting well into it. My own cock was hard and throbbing and I was in two minds whether or not to take him in hand but I resisted - perhaps there would be a more interesting way to cum before too long!

"Oh God - its cumming!" cried Sam, "Its cummmming - I'm there! Ooooohhhhhh yeahhhh! Uuuuugghhh!"

I felt his penis swell and thrust one more time before bursting loose with a powerful jet of hot cum that seemed to penetrate way up inside me. A second and quickly a third jet sprayed deeply into me again; a fourth and a fifth squirt adding to his deposits inside me before he slumped heavily onto my back.

"Bloody hell - that was intense!" he said, "You made me cum so hard!"

"Felt you - way up there," I said, having thoroughly enjoyed the power of his penis, "That was a good one."

Paula was already there with the towel as Sam dismounted and had it clamped over my hole as soon as his cock slithered from my hole; Paula cleaning it for him as he moved away. I got up and was soon seated on the settee once more, but this time it was my turn to be sitting on the towel!

"So, Sam, you're getting there!" I said, putting my hand on his knee as he sat beside me, "You said you hoped I'd be the man to help you, so how am I doing?"

"Pretty well so far," replied Sam, his hand moving gently over his recently emptied penis, "But you haven't stuck your cock in my arse yet, have you?"

"Didn't know if you were up for that yet," I said, feeling my own penis quivering with excitement, "I bet Paula would like to have a go too, if you're willing."

"Hmmmm - might be a bit of a stretch, taking that one," Sam said as he looked at Paula's already reviving cock, "You take me first; anyway, that way you'll be my first in all three holes!"

'An unusual hat-trick of penetrations,' I thought, 'But then this whole evening has been completely unusual.'

I stood up and turned to face Sam, who immediately grasped my twitching, excited, dripping penis and lovingly kissed the end, licking the little bubble of precum from the tip as he did so. He peeled back my foreskin and explored my knob, his tongue exquisite on the ridge of my crown, sending waves of pleasure all through me.

Then I almost growled as he let my cock penetrate deep into his mouth before letting it slide out with a small plop.

"He's ready," said Sam, his eyes glittering with anticipation, ""Come on, come and put him up me!"

Paula already had the tube of KY at the ready and I blew her a kiss as I took it from her before getting myself into position. Sam had got off the settee and now was bending over it; his cute arse at the ready, the towel stuffed in his mouth. I spotted that and tried to take it from him to replace it with something nicer but he stopped me.

"No - I like it; it smells and tastes so sexy; there's loads of tastes from all of us here and every time I suck it a bit more or even just breathe in, it gets more exciting," he said, "And its all sticky and smelly and lovely!"

He groaned as he rubbed his face over the towel while I lubed up his arse and my cock, before shuffling up close behind him.

I reached around him and found that his penis, despite having recently discharged its load up inside me, was hard again, so I gently caressed his knob as I started to try to penetrate his virgin arsehole.

He was tight; that was for sure and I had to try different angles of approach before I managed to make even a small impression in his tightly puckered hole even though I'd lubricated both him and my penis thoroughly.

I could have used my fingers to open him up but I felt that because mine was going to be the first penis to enter him, then fingers shouldn't play a part.

And I could have just driven my cock hard up him in one go too, but that wasn't my style either, so I continued the more gentle approach...and slowly but surely my knob began to slide inside.

"Careful, careful," moaned Sam, "Feels so big!"

"Relax," I said, rubbing his penis more vigorously to distract his mind, "Push outwards if you can; the lube will do the rest."

I kept up the pressure and there was a sudden release of pressure as Sam must have pushed as I told him and my knob disappeared out of view.

"Aaaaahhhhh!" groaned Sam, wincing, "You're stretching me - hold still for a minute."

I didn't mind taking my time, even if my cock had other ideas - he was all for getting the best he could but I held back, trying to remember my own first time.

Oh yeah - out on a fishing trip when a pal and I camped overnight. We didn't do a whole lot of fishing but we certainly got to know each other a lot more intimately! He'd taken me doggy-style, and all we'd had to hand was a small pot of Vaseline for lubing our reels but that didn't stop him from thhrusting his seven inch cock deep into me in one thrust!

At almost two in the morning and out in a tent on a still, quiet night beside a lake where the sound would carry, there was no way I could scream; we'd have been surrounded by rescuers in minutes!

Instead I'd just bitten my arm as his cock took my virginity but thereafter I'd been able to relax and let him slide in and out until he shook and emptied his hot cum inside me.

With that memory still clear in my mind, I allowed Sam's hole to get used to being stretched, until finally it was Sam who instigated the next move.

"Ok, doesn't hurt now - just feels full," he said, his voice somewhat muffled by the towel, "Come on then, bit more...but go easy."

I leaned in a bit closer and simply by tilting my pelvis a bit, I allowed my cock to penetrate inch by inch into his newly broached rectum.

"More then, I can take it now," said Sam from the towel but I patted his hips.

"I'm all the way in," I said, "Perhaps half an inch more but you've got me right up there - well done!"

Sam lifted his head and looked back over his shoulder, a big smile on his face.

"Wow - done it!" he said, "Feels weird but wonderful; I've got a man's penis inside my body - it's fantastic!"

"How about the next bit though," I said as I began to wobble my cock around inside him, "How about when I start fucking you?"

"Well, you're going to fill me with your cum somehow so you'd better start fucking me!" he said, chuckling "Unless you know any other way to get your cum up there!"

"Can't think of one," I said as I began to slide in and out of his hole and that concentrated his thoughts.

"Aaaahhhhh yessss," he moaned, "Still feels weird and stretchy but its better that it was."

"It'll feel even better soon," I said, "Once you get used to it, it'll start turning you on."

There was silence from the towel end so I continued to smoothly saw in and out, only changing the depth of my thrusts but not the intensity.

I kept that up for a while and then grasped his forgotten penis once again, now rubbing it more actively.

"Going to start fucking you harder now - won't be violent," I said, "But I can't cum without fucking you a fair bit harder."

"Yeah, do it," moaned Sam, lifting his head, "Its ok now - feels fine; push deeper; go quicker!"

Now using both my pelvis and my hips I increased the speed of my thrusts, now varying the angle and depth of my thrusts and making Sam moan and pant, but he wasn't stopping me.

Harder and harder I fucked; it was my turn to pant now and sweat was bathing us both as we screwed; Sam's own body now responding and thrusting back at me at last.

I noticed movement beside me and there was Paula, stropping her big hard-on; really getting into it as she watched us rutting.

And it was pure and simple rutting now; no nicety, just lots of power and effort and noise!

There were grunts and groans rising from us along with a haze of hot sexual odours and slapping sounds filled the air too as I slammed my cock home, time after time.

"Come soon," moaned Sam, "Don't make me sore - hurry up and cum!"

"Won't be long; squeeze me harder if you can," I asked and I felt Sam comply; his sphincter muscles contracting around my shaft and quickly raising my level of orgasmic pleasure.

"Ooooh yesss, yessss," I groaned as I continued to fuck hard, "Nearly there now; I can feel it coming!"

"Come on then Chris," said Paula from beside me, her hand a blur on her penis, "I'm almost there too!"

And with a last deep thrust I froze as fire shot through me; tongues of flame turning me liquid; spasms of lust sending jet after energetic jet of spunk from my thrusting penis, deep into Sam's rectal passage.

"Fuuuuuck!" I cried as I unloaded, "Oh fuuuuuuuuck!"

Paula just grunted loudly and suddenly hot splashes of cum sprayed over my cheek and into my hair. She grunted again and more cum squirted over Sam's back; then another load splattered against my turned face. I licked it from my lips, loving the warm slippery texture and taste of fresh cum, before returning to my own partner.

Because I realised that of the three of us, Sam hadn't cum and since I had hold of his cock, I could at least remedy that situation.

Briskly I restarted my actions on his shaft; feeling the slipperiness of his precum that the pressure of my cock on his prostate had produced; slipperiness that now helped me to toss him off that much quicker and easier.

Sam moved the towel to his groin, holding it nearby as he approached his own climax, both of us panting again as we worked hard together.

"Yeah, yeah, cumming, cumming..." said Sam suddenly, "Here it cums, here it cums!"

I felt the towel cover my hand and his penis as he jerked hard beneath me; then a spurting sound as gout after gout of spunk squirted energetically into the towel.

"Ohhhhhhhh," he moaned, "God - that was good..."

He straightened up somewhat, my cock still embedded inside his anus as he brought the towel into view and opened it out. There was a big puddle of white sticky cum in the middle and he held it up to us.

"See what you made me do Chris," he said, "Do you want it?"

I shook my head, not so much because I didn't fancy the idea but because I was too knackered to even be interested, and moments later Sam raised the towel to his own lips and simply sucked the puddle into his own mouth. A quick open-mouth display to us and down it went, Sam licking his lips with obvious relish afterwards.

"Do you want to take him out now?" he asked as he lowered the towel beneath my balls and I hummed my intent; I needed to rest.

"Yeah, let me out," I said, "Try to squeeze your arsehole once I go or you'll flood the place!"

Slowly I pulled away, sufficiently slowly to allow Sam to tighten his hole, even if a little trickle of whitish cum did slide out first, but the towel was there for that.

I stood up feeling totally sated. There was Paula's cum streaked in my hair and sticking to my arm, my face and my back; my cock was slippery with lube and cum and even my mouth still held the taste of Paula's offering...and all I wanted to do was to sit down!

Paula was still up and about however and was now hovering at my elbow with another chilly can - just what I wanted!

"Whoooo," I breathed, "That's about enough for now, all I need now is to cool down and then have a nice shower. Any chance?"

"I was going to suggest just that," said Paula, now coming to sit beside me on the settee, her warm firm breasts squashing against my side, "A nice intimate shower and then..."

She wriggled around beside me, her nipples rubbing hard over my skin and even though I'd just had a damn good fuck, I felt my penis jerking with eager anticipation.

I'd just begun wondering what we'd do with Sam, the obvious wallflower in our group, when a mobile phone chimed somewhere.

"Mine! That's a message!" called out Sam as he groped in his pile of clothes and soon he was scanning the message with a huge smile on his face.

"Hey," he said happily, "Tony's asked if I'd like to keep him company and I know what that means!"

"What?" Paula and I echoed.

"Well, he's been after me for ages and I don't half fancy him, but I've been scared," he said, "But now, thanks to you two, I can't wait! I bet I can get him in bed before the nights out!"

"Who's Tony," I asked, not knowing Adam from Eve really.

"He's only the director!" said Sam brightly, "Hope he's got his casting couch ready!"

We laughed happily as Sam replied to the message and began to get dressed although he now looked strange as he pulled his girl's clothes back on.

"You can laugh," he said, "But when Tony sees me like this he won't be able to keep his hands to himself, I hope!"

Moments later and Sam kissed us both before disappearing through the door, leaving the two of us to breathe more easily.

"So what do we do?" I asked and Paula had all the answers as she enveloped me in her arms and we kissed again, but this time with passion and feeling.

"First we shower; then we can eat if you're hungry; then we can go to bed and then we can fuck and fuck!" she said, "You're staying the night, in case you didn't know!"

Was I complaining - no way!

I'd found a companion, a beautiful one at that, all complete with everything I loved. A willing hole, a nice big cock and wonderful breasts - not to mention a shower and a bed!

I could just feel my life changing as we walked hand in hand up the stairs - my penis just wouldn't calm down - life had improved so much!

There was a big company not far from this town, that had been head-hunting me for ages; perhaps it was now time for a change of employment.

Perhaps I'd be able settle down and move in with Paula; perhaps I'd found exactly what I'd been looking for; my proud, magnificent shemale!

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5 Comments
AnonymousAnonymousover 9 years ago
brilliant!

Can only agree with everyone else. Chapter 2 please!!

Chris7swChris7swover 9 years agoAuthor
Love your support! Thanks!

Many thanks fellas; nice to hear from you - glad you found it fun.

It was always planned to be 'entertaining' as well as erotic, as many of my stories are; they're not everyone's cup of tea but I prefer being cheerful and amusing rather than blunt and 'straight in there' so to speak.

I am toying with Chapter 2 but this one was enough to confuse me as well, at least for a while!

Sorry if there are some minor errors....diligent re-reading, spellchecking and proofreading still didn't help, I'm afraid.

HeisenhugHeisenhugover 9 years ago

I'm with Joscelyn on this one; Fucking brilliant, literally as well as figuratively.

How's the song go? Boys who like girls that were boys but like boys who'll be girls that like boys... No, don't think that's exactly the lyric but oh well.

AnonymousAnonymousover 9 years ago
Neat

I LIKE SEX

AND PUTTIN' ON SKIRTS

AS LONG AS UP MY ASSHOLE

CUM DOES SQUIRT!

Joscelyn2tgJoscelyn2tgover 9 years ago
Fun, Sexy, Well Written, And Just Plain Wacky...

...At times, and you almost needed a character list (with gender 1 and gender 2, lol). I've never read anything that manages to stretch the transgender rainbow into such a psychedelic 'whirlpool' before. I really liked it, it was a fun read. The writing had a couple hiccups but hardly anything to really complain about. A second set of eyes would have found them. Thanks for sharing such a delightful piece of work, and it seems there could be a chapter 2? Cheers! --- Josie

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