Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereOn my first visit to Throbwood at the height of their amateur dramatics season, I'd walked in on the thespians closing performance street party and I'd met some wonderful people.
In particular there was Paula the lovely shemale, who'd played the part of James and Sam, the youth who was becoming a woman, who'd been one of his love interests.
Between us we'd had a thoroughly debauched time that evening and Paula and I had almost become lovers but circumstances hadn't worked out, so I was still merely a visitor, despite deeply longing to return.
And so this is the story of that next well-timed return......
Time had marched on and although I'd been back to the scene of the crime on several occasions on business, I'd yet to be there at the right time to join in with the debaucheries of their 'end of season' party again.
That's not to say that nothing had happened in the interim – far from it – but the activities had been, more often than not, far from the little town of Throbwood.
My delightful shemale playmate Paula had been down to visit me on a number of occasions and I'd been able to enjoy her delightful company as well as her exciting body and I need hardly add, she'd enjoyed my body too.
But we lived too far apart for a proper relationship and once the optimistic plan of changing jobs fell through (the offer from the company I fondly hoped would employ me was simply not good enough) I had to admit defeat.
So Paula and I agreed completely sociably that we'd have an open relationship and that we'd, at least for now, just make the best of what we could.
So while underneath I still felt a hell of a lot for Paula, with circumstances playing against us and since we couldn't be together to satisfy my sexual appetite, I went hunting.
I'd actually rejoined my own local amateur theatre club, my interest in acting having been reinvigorated, so to speak, by my meeting with the Throbwood group and I soon found myself cast into the latest production of a period whodunit set in the 1940s; me being the proprietor of a hotel through whose doors all the actors came and went and whose front entrance lounge was the main scene of the action.
As it happened, I'd arrived on the scene after the rest of the cast had been chosen – hopefully my timing would be better in the play – and I'd been lucky to get the part; the original actor having had to back out through illness, so I was able to step in quickly. My part was comparatively easy as my character didn't have a huge amount to say so I had no massive script to learn.
I seemed to slide into place perfectly well enough and gradually I became aware of others around me, including one of the other actresses who was a most interesting looking young creature; dressed to the nines, dripping with jewels and silks and looking the proverbial million dollars.
I had no idea of her name; all I knew was that I was attracted to her immediately and one glance from her flashing eyes and dancing lashes sent shockwaves right down to my groin. A second longer glance that swept me from head to toe caused things to stiffen immediately – I just couldn't help it.
My eyes followed her lithe swaying body across the stage with enthusiasm; this was one fine lady and I knew immediately that I'd have to get to know her better, a lot better, with a bit of luck! Thank heavens we were going to do a four week run – I'd have enough time to find out a lot more about this particularly lovely lady.
It was at our first full rehearsal that I heard her speak for the first time; a gloriously husky sultry voice that thrilled me as it would no doubt thrill the audience, but now I knew a bit more. She was called Nancy in the play, so at least I had some kind of handle by which I could address her when finally I had a chance to socialise with her.
It took a week of performances before I found myself even in the same room as her and fortunately it was at the theatre bar afterwards when we were both still in full costume that I found her and managed to have a chat.
"Hello Nancy," I said, sort-of chatting her up as we came face to face in the small bar, "You looked incredible tonight and you sounded even better!"
"And hello to you too," her sultry voice replied, "I'm pleased to meet the manager of this fine establishment! So who are you then?"
"I'm playing the part of Oliver Lord, the manager, as you said, of our wonderful hotel, but I'm Chris in real life," I said, my voice quivering as I anticipated her response, "And I'm delighted to meet you too."
Nancy checked me over once again, her vivid eyes sweeping over me once more, making me glad I was wearing comparatively baggy trousers rather than tight jeans since things immediately began to get excited.
"Obviously I'm not Nancy, I'm Andrea actually," she said in that warm husky tone, "So what's a nice man like you doing in a place like this?"
We both laughed at the corniness of the question but we needed something to open our chatter with and that would do well enough.
"Always loved acting," I said chuckling, "I'm a salesman and I love talking so this kind of thing gives me a chance to let myself go a bit."
"Oh and me," she replied, "And I just love to be able to dress up, as you may notice."
Oh I could notice all right – she looked exotically erotic and terribly tasty, from her flowing glowing hair complete with embedded pearls right down to her diamante encrusted shoes, not forgetting her silky stockings and her beautiful shimmering midnight blue dress that swooped excitingly from one shoulder.
"You do it really well," I said, praise slipping easily from my lips "You really look the part, absolutely perfect for the period, beautifully done."
"Thank you kind sir," she simpered, "That's why I love the theatre; where else could I dress like this?"
"Do you have time for a bit of a chinwag?" I asked politely and hopefully, "Let me get you a drink and we can go and sit down if you care to."
"What a nice idea," she hummed, resting her hand on my arm, "Gin and tonic for me then."
With our drinks in my hands we headed to a corner of the bar where we made ourselves comfortable, side by side on a large settee – hardly a pub accoutrement, but this was the theatre bar!
Her perfume enveloped me, a lush fruity oriental aroma that set everything fluttering and I knew she'd captured me; I was hooked!
And so we chattered aimlessly for a while, each discovering minutiae of the other's life while appearing not to be prying and time just rolled on and on and suddenly we were being told that the bar was about to shut.
"I do like your company," said Andrea, her hand resting on my arm once again, "Shame we've got to stop. Perhaps you'd care to continue this conversation back at my place?"
"Love to," I said eagerly and delighted to have made it to first base already, "Or my place if you'd prefer..... I live just out of town – we could always adjourn there....."
"No – try my pad; it's just down over the bridge, an easy walk," she said as she stood up and smoothed her dress with her slim hands.
Then she held out her hand and we linked arms as we left the theatre and walked away.
And somehow now there was a degree of intimacy; we were closer already and our hips kept rubbing against each other as we walked, until we reached the bridge where we stopped.
The late evening was warm and a soft breeze coming up the river was gently cooling on our faces as we stood side by side, until I moved behind her and allowed her to lean back against me.
"Soothing, isn't it?" I said softly as I smoothly put my arm around Andrea's waist, "Relaxing too."
She rested more firmly against me, her soft posterior squirming slowly against my thigh and groin.
"Mmmmmm," she husked, "I could get to like this!"
My growing erection was now under threat as Andrea centred her bum over my front; her hips now working her buttocks firmly against my developing hard-on while her hands covered mine as both of my hands now rested on her flat stomach.
"Feeling naughty?" she asked, looking over her shoulder and it was my turn to hum a reply.
"Mmmmmm, definitely," I replied, "Feels as if I know you already."
"Feels as if you want to know me a lot better!" she said, her buttocks now pushing hard against my very stiff penis, "Come on then lover boy, we're wasting valuable time!"
With a final push against her rear end we turned to face each other and seconds later we were glued together, our lips and tongues working wildly as we began to express our feelings more clearly.
"Oooh, come on," said Andrea, her breast heaving, "Let's get home."
Not five minutes later and we were at her door; her home a studio flat inside what had once been a huge warehouse by the river. The walls were old worn bricks and the ceiling of the entrance hall had huge black beams that gave the place loads of character.
Up the wide staircase we arrived on an open walkway that lead to the flat doors themselves and soon we were inside number 18, a stylish retreat, as somehow suited a thespian.
"Number 18," she said, "Bought this place when I was 18 – my first go at the lottery and I won enough to buy it – I couldn't believe it. That's why I chose this number."
"Suits you," I said roguishly, "So young and pretty...."
"But not 18 any more," she replied, "I've lived here five years now...."
I looked around, noting the profusion of artistically placed garments used as decorative accoutrements – props from years gone by I guessed, although where a pair of silk knickers came into it I couldn't decide.
"You're well into this theatrical stuff," I said as I turned, "You obviously love clothes."
"Ohhh, definitely," she said, "Where would I be without them?"
"In bed perhaps?" I asked and we both laughed cheerfully; the ice had been broken already; the night was about to become even more interesting!
"Cheeky!" she replied as she bent to take off her shoes, her cute arse aimed at me, "What makes you think I don't wear anything in bed?"
"Just hoping!" I said, "Be lovely to see you laid out naked on the bed."
With her shoes off she was those few inches shorter than me and now she sidled up and backed towards me.
"Undo me please," she sighed, "I need to get out of this."
I reached up and undid the clasp behind her neck and took hold of the zip.
"All the way!" she breathed, "Right down."
I let my fingers slide the zip down and down, exposing her smooth back; her thin black bra strap and finally the top of her silky black knickers, where I let my fingers rest for a moment or two.
"And my bra," she said and reluctantly I lifted my hands and unclipped the strap which fell loosely to her sides.
Her hands came up and covered her breasts, also holding her dress in place as she blew me a kiss and walked away, presumably to her bedroom.
I stood there, suddenly realising that my penis was about as hard as stone and was causing a huge tent in my trousers, not to mention a large damp patch.....it was too late now to do much about either although I did run my hand over my cock to position him more comfortably.
I didn't have long to wait before Andrea reappeared, now wearing a fluffy blue shortie bed jacket over what appeared to be a matching soft blue set of bra and knickers and all complete with sleek blue-black self-supporting stockings. Her face was still made-up although I did notice that she'd put on a slightly darker lipstick now.
I almost growled with excitement; she looked incredible; entirely edible and I felt my whole body respond; this was one fine lady and she was definitely going to be introduced to my cock, all of it!
But Andrea merely stood in the doorway to the lounge, one arm raised and resting against the door frame, her hips cocked but rotating slowly.
"Nice enough for you?" she said, simply oozing sex appeal, "If you like it, you'd better come and get it!"
And with that she turned and walked away from me, her hips swaying as she moved while I quickly discarded my shoes and jacket and followed her.
The first door I came to was to the bedroom and there she was, stretched out on the big bed, a pile of cushions and pillows behind her, the lights soft and beguiling as she waved her hand to me.
"Come on Chris, come here; make yourself comfy," she said, patting the bed beside her.
I've seldom removed my clothes so quickly and I was naked in seconds and laying on the bed just seconds later, my body within easy arm's reach of Andrea.
"Gosh, you look good; good size too," said Andrea as I settled down, her eyes immediately locking onto my erection before sliding up my torso.
My penis was rigid, pointing up my body and already glistening with precum as Andrea's hand reached out and touched my chest, her touch sending shivers of excitement right through me once more. Slowly and gently her hand moved around my chest, feeling my nipples and my muscles; not that I was all that muscular; then sliding downwards towards my navel.
But I wanted to touch her too and I reached out, my hand coming to rest on her waist before starting to travel downwards towards her knickers – but Andrea stopped me, her own hand holding mine firmly.
"Wait," she said, "Let me tell you something – I hope you won't mind......"
I shook my head to express that whatever it was, I didn't mind.
"Whatever....come on, won't worry me," I said, "Let it all hang out!"
Andrea laughed loudly at that.
"Ah – that's the problem actually," she said, "If you take my knickers off then it will all hang out – I'm a man actually!"
For a moment I was simply gobsmacked; unable to respond although my penis simply shook with excitement.
"Wow!" I exclaimed, "You....a man – you look so damn good as a woman! Fucking hell; and I thought I'd always be able to see through all that make-up and stuff but you've shocked me."
"But does it put you off?" asked Andrea softly, "You haven't leapt up and run off, so you're not scared Chris, are you....please."
No I wasn't scared and now that my mind had absorbed the reality I was far from scared; just the opposite in fact.
"You'd better get undressed," I said, almost growling, "Completely! I want to see what you've got!"
He began stripping down, wriggling around on the bed until he was naked. He ran his hands over his smooth chest, then down to his groin to pull his penis out from its hiding place between his legs.
"Sorry I haven't got breasts," he said, "I'm not a tranny or anything like that, I just like cross-dressing – that's why the theatre's so good."
"But you are gay though, aren't you?" I asked and Andrea let a naughty smile shimmy across his face.
"Oooh yes, definitely," he said, "I guess I'd like to be a woman but then I also like being a man when I want to."
"What, as in being able to fuck?" I asked and Andrea nodded, his cock bobbing in time with his head as it slowly became more erect.
He looked down at it and spoke again.
"Oh, I guess you'd better call me by my proper name now I'm undressed," he said, "I'm actually Danny – Andrea is my dressed-up name."
As I've said, he wasn't as tall as me, being perhaps about five foot nine and he was somewhat slimmer too but he made up for his 'deficiencies' by having a magnificent penis – nine solid inches of trimmed manhood that was going to need constant attention!
His cock had now risen from its crumpled position and now stood eagerly tumescent and obviously delighted to be part of the proceedings.
"Do you still want to touch me Chris?" he asked, his lips quivering.
I answered by pulling him to me until our bodies were meshed and entwined; our legs interwoven, our cocks excitedly squashed together; our chests hotly against each other and our mouths locked in a slippery embrace.
For long minutes we smooched and made out and it was only Danny's urgently thrusting penis that made us stop – he needed relief as much as I did and all our intimacy was simply making us both more and more horny.
"Sixty-nine?" I suggested and Danny was up and turning around immediately and I'd hardly made myself comfortable before I found Danny's penis almost forcing an entry into my mouth!
It was lovely to have another nice cock to enjoy; I still missed Paula a lot.
I managed to distract him long enough for us to settle side by side, then I pulled his penis back to my mouth and allowed it to slide inside.
Danny hissed his pleasure as his throbbing cock moved in and out of my firm lips and as my tongue swiped around his knob, enjoying the slippery feel of small floods of precum that were now oozing from his penis.
"I won't last long," he moaned, "I've been waiting so long....."
The sooner I could get a nice mouthful of warm cum the better and I began using my hand on him as well as my lips and tongue until Danny was groaning and jerking uncontrollably.
"Oh Chris, Chris, coming, coming," he moaned, "Very soon.......ahhhh, ahhhh, cumming, yessss! Here it cums!"
I clamped my lips tightly around his cock; partially to stop it pushing too deeply into my mouth and partially so that I wouldn't lose even a drip of spunk as his penis spat gloriously warm, slippery and tasty cum into my mouth. I swallowed once before he filled me again; his sticky emissions coating my teeth and roof of my mouth.
Then I let him slide out so I could get the feeling of his cum on my lips as well, just loving the scent and the salty taste and the slipperiness of his spunk.
Danny was panting as if he'd just run a marathon but he was ecstatically happy, simply bubbling over with pleasure.
"Oh Chris, where the hell have you been all my life?" he said as he lifted his mouth from my cock, "That was fantastic, you're so good at that!"
"Had some excellent teachers," I said, thinking of Paula and Sam, "But are you going to do me now?"
Danny looked at my cock that he now held in his hand and then looked down at me.
"Stay there," he said as he got up off the bed, "No, actually roll over onto your back – won't be a moment."
And by the time I'd settled on my back he was climbing back onto the bed and soon was astride my thighs, his cock already rising once more.
I shut my eyes to better allow the feelings to take over as Danny's hands caressed my penis and I felt him moving around as he prepared to bring me off.....and then I felt something different; not his hand or his mouth on my cock but a warm and slippery place that now seemed to try to engulf my cock.
I opened my eyes to see Danny screwing up his eyes and mouth as he lowered his arse down over my penis!
"Wow!" I said, "Didn't expect that already!"
"I needed you," moaned Danny, "I so want you inside me."
And I just slid inside him, smoothly filling him on a coating of gel that lubricated my passage.
Danny breathed in quickly as I penetrated him but thereafter he merely sighed with pleasure as he sank down onto me and my penis filled his rectum.
"That's lovely," he sighed, "I can feel you jerking right up inside me; I'll squeeze you and ride you and you can fill me, can't you?"
"Yeah, yeah," I groaned as I began to thrust my cock up at his descending arse, "Nice and tight and warm and smooth....."
We entered that phase of fucking that doesn't need words, just actions. Together we thrust and parried, squeezed and caressed; pushed and penetrated, groaned and grunted; a wave of steaming sweat rising from us, carrying with it the strong scent of two horny males rutting hard.
"Oooooh fuck," I moaned, "Won't last long now, you're gonna make me cum!"
"Oh yesss," hissed Danny his hand now working away on his own erection, "I want to cum when you do, wait for me please."
"Don't be too long," I said, knowing that once my orgasm started there was no way to stop it, "I'm getting close."
"Yeah, yeah, yeah, so am I now," Danny said between pants, "Oh fuck, here it cums!"