A Night to Remember
It had been a long day, well week actually. Boring meetings and conference speakers, I could barely stay awake in the taxi on the way back to the hotel. I work in insurance and hate every minute of it but have not got around to making a career change yet. Besides, the money and perks at my particular firm are phenomenal. Just for example I am staying in a spacious 3 bedroom suite by myself while interstate for the week. Not to mention the indirect perks such as the social life and the opportunity to meet people and party as hard as I want
I entered the room and ran the spa and started tearing my clothes off and climbed in with a bottle of champagne and within 15 minutes was asleep in the spa at around 6 pm. Not the best idea in the world but I needed the rest as I planned on a late night out at a nightclub or two. I awoke to the phone ringing next to the tub and looked up at the TV screen to see a muscle bound Latino male being dominated by a gorgeous Asian Shemale, she was straddled over his face force feeding 8 inches of pork sword down his throat.
I answered the phone and it was Steve from work. “Hey dude, I think I am coming down with something so I’m going to give the clubs a miss hey”
“Wow bummer” I responded half heartedly because to be honest Steve was a bit of a drag sometimes. “Hope you feel better mate and I’ll see you in the a.m.” I said and hung up.
Well that settled it I was already leaning towards Tranny hunting and without Steve there to muck it up I was sure I was in for a good night.
Feeling somewhat refreshed from my snooze and the spa I dressed and looked at the clock. Holy crap, my little power nap had taken me through to 8:30. I decided to skip dinner and grab some munchies at this nice little bar I knew around the corner from the hotel. At that time of the evening there was only a handful of people there but I was set up at the bar making small talk with the girl that was serving and in a position that allowed me to scan the room perfectly.
Sexually I don’t know what label put on me but I guess I enjoy women and transwomen equally but tonight I was hot for the latter and I was considering and hoping I guess for a little shemale domination to take place. I had never tried it and it rarely appealed to me actually but tonight felt right and I was set to sail in unchartered waters.
I had been chatting to Skye for around half an hour and had a really enjoyable conversation about her work and life in general when a drop dead gorgeous Auburn haired (with dark roots) Asian girl came up and bought me a drink and sat next to me. “Well thank you darling I am Chris and you are?”
“Horny as hell” she replied leaning in and piercing right through me with the biggest, sexiest, most hypnotic brown eyes. “Haha I am Lulu but you can call me baby if u like” I have to tell you my dick stuck out like a telephone pole and I was busting for a piss. I had to sit there sipping her drink and talking to her in sheer agony. I wanted to bend her over the bar right then and there she was so hot but I had to use the bathroom first. Finally Lulu saw some friends arrive and went to greet them so I told Skye to let her know I would be back and made a run for the toilet.
There was a full set at the urinals so I ducked into a cubicle and aaaaahhh bliss. I savoured the relief for a couple of moments then suddenly...
I felt someone hard up against my back and a strong hand pushed my hand of my cock and grabbed hold of me. I heard the door shut and lock and then heard Lulu’s sweet voice “Bend over hunny” Holy hell I was about to get assfucked in public and I hadn’t exactly given consent. I stood stunned for a moment and then Lulu began stroking my cock and nibbling my ear and breathing on my neck. I melted into position leaning on the back of the toilet. Lulu grabbed some spray lube from her bag and prepped my ass and her shaft. This was not my first time with a transwoman but it would be only my third time at being topped and I still felt like a complete amateur.
Her head pushed up against my entrance then she paused and said “Who is the boss tonight baby?”
“You are. Please make me your slave, all night long”
“Music to my ears baby” she whispered sweetly.
WHAM! She slammed what I imagined to be 12 inches deep into my body (I later found it to be merely 9 but it was thick as a deodorant spray and hard as a rock).
“Aaaaaargh” I yelled.
“Oh hush baby we’ll get in trouble” she pleaded
“Oh god it hurts, it hurts” I grunted through clenched teeth.
“You want to break our deal?”
“No No just... I’m ok. It’s just that you’re the biggest I’ve had is all, it was a shock”
“Good boy, gooooood booooy” She whispered trailing her finger nails gently down my back and sides as she began to rock in and out of my throbbing ass. The movement immediately began soothing the aching and her thrusts became pleasant.
“Oh you are so tight baby I think I will cum soon” She whined. Immediately she began panting “Yes yes yes” and blasted my insides with her jizz. She stayed inside me and began to go limp for a while and then I felt her slide and flop out. I turned over gingerly so I was now sitting on the toilet with her cum trickling out of my ass. I looked up at her as she wiped tears from her eye. I was completely puzzled.
“Are you ok baby?”
“Fine Hun now let me fix you up” she said flopping to her knees and swallowing my cock in one complete action. I thought my eyes would pop out of my head or my knob would come off in her vacuum like mouth as she nearly sucked me inside out. She massaged my balls as she sucked long and slow up and down my shaft. Then I felt her finger gently giving me a soft soothing rim massage as if to apologise for the brutal attack she had just administered. She slid her finger gently up inside my ass hole taking me over the top. I grabbed and held onto the toilet seat as my hips bucked forward again and again blasting cum down Lulu’s throat. She hoovered the lot without blinking and winked at me when my orgasm was complete.
“Good, good boy” she said again. She pulled down her skirt as I got up and got myself together then said “Come, I want you to meet some friends”
“Oh okay” I said without really hearing what she had said.
We arrived back at the bar where I was originally sitting and on either side of mine and Lulu’s seats were two of her friends she introduced as Minny and Adrianna who preferred Anna. Minny (short or derived from Domenic) a curvaceous, long legged Italian girl with dark mahogany curls down past her shoulder blades had beautiful but soft facial features and the thickest set of lips I have ever seen on a woman. Anna was a stunning yet somewhat shorter Argentinean girl. Very thin but with curves where it counts. An absolutely luscious ass and cute handful size tits. Needless to say amongst these three I felt way out of my league.
After chatting and getting to know the girls better I started to get the idea that I may be in for a chance with each of them. I was picking up vibes from them all but I could not figure how I was going to achieve a tick in each box so to speak. I only had one night left and flew out at size the next evening. I guess it was achievable but it could turn out to be a lot of running around.
Just then Minny said “So do you mind if Anna and I crash at your hotel tonight with you and Lu. You said you have three rooms right?”
“Oh hell yeah that would be great” I blurted out sounding like an absolute juvenile.
“I mean, that is fine” At this stage I had not even invited Lulu to come back to my room but had fully intended to.
“Hold on girls. Chris and I have an arrangement. He is my slave and my slave only. That means if you require his assistance with anything at all it must be approved by me first”
“Of of course my dear” Anna beamed
What the hell was happening? They were scaring the living shit out of me but making my cock uncomfortably hard at the same time. I got up the nerve to but in “girls, deal or no deal I am only human”
“Oh that’s ok baby the Viagra will kick in soon” Minny said before laughing a sinister laugh.
The cab ride back to the hotel was a blur of tongues and tits and I wondered once or twice what I had gotten myself into. When we got into the room Lulu ordered me to get undressed. “Now girls line up” she said. The three of them got on all fours on the bed and Lulu ordered me to start with Anna in the middle. I looked at the ceiling with thanks as hers was the most magnificent ass I had seen. “Lick her ass slave” Lulu ordered but I was on it. I loaded her ass with saliva and slid in quite easily.
Anna moaned with satisfaction and I slowly increased the pace and depth. “Prep Minny dear” Lulu ordered. I was glad she was not one of those girls that dominate with abusive language and down putting remarks. I reached in and began stroking Minny. “Oh holy shit, Minny by name but not by cock size I said out loud”
The three of them laughed. Minny is huge, probably a little thicker than Lulu but a lot longer. Here I was pumping in and out of the most incredible ass I had ever seen, stroking the most incredible cock I had ever touched and being ordered around by the most beautiful lady I had ever met. And I was supposed to be a slave.
“Change” Came the order. Lulu guided me in behind Minny and I slid in immediately drawing a gasp of pleasure. Lulu lay beneath Anna tugging and sucking her cock as I began to pound Minny. Lulu paused just long enough to order me to play with her balls and cock. I felt like an ass for having to be told but at least it gave Lulu the opportunity to act out her role. As her cock slid up and down in my fist I remembered how it felt in my ass. First it felt so alien and so brutal then so beautiful and so exciting. I had had to think of something else so I would not cum early. I was just wondering how Viagra works and whether I would get hard again immediately when Lulu ordered another change.
This time Lulu flipped over so I would be entering her missionary style and Anna and Minny arranged themselves into a 69. “Fuck me hard boy” Lulu ordered and kept ordering MY balls were making a very audible slapping rhythm against her ass cheeks and here gorgeous tits were bouncing up and down. I grabbed her shaft and began pumping as I looked over at the mutual blowjob occurring beside Lulu and I. The sight nearly made me cum. I think Lulu was watching the through the same eyes as she started panting “I’m Cumming, I’m Cumming” I released and emptied into her ass as she sprayed her own tits and stomach with her own sweet, sticky jizz. I guess the sounds of our combined orgasm was enough to help Minny and Anna across the line as I watched them slurping and sucking each other’s seed diligently trying not to spill a single drop.
We lay exhausted, hugging and kissing for at least half an hour before Lulu ordered me to get up and run a fresh bath for them. We chatted and played in the bath for a long time. These girls were sweethearts. They were obviously close friends and I adored them all. They talked about family and friends and although I tried not to pry they answered a few questions about the whole Male to Female conversion and were refreshingly honest. There were one or two moments when I had to fight back the tears when Anna spoke about being cut off from family eternally and Minny and Lulu talked about being beaten senseless by people because of their sexuality.
Lulu was the first to realise we were losing party mode and ordered me to call up room service for some munchies and alcohol.
By the time the munchies arrived we had forgotten we had ordered them. We were having such a great time in the spa. Minny and Anna had individually ploughed my ass to completion and were satisfied that they had delivered a load of jizz each into my body. I had sucked everyone’s cock excluding my own and was satisfied with the overall success of the evening. But I had no idea what was Cumming next...
“Room service” rang out from the hallway outside and Lulu went to answer the door.
“Shouldn’t you put some clothes on” I said without thinking?
“Are you questioning me slave” she barked back at me. “That will cost you” she warned.
The girl entered with the trolley and immediately went bright red with embarrassment.
“What’s wrong sweetie? Surely you have seen a Tgirl naked before”
“Well no, I mean yes but”
She was so shy and embarrassed and just stared at all of us with a cute but bashful smile on her face. “Well do you like what you see princess?” Minny asked a little harshly and defensively.
“Oh yes, you are all beautiful. It’s just...I mean I have...”
“Never seen a shemale in real life sweetie? Lulu completed her sentence for her.
“No” The poor girl mumbled as she looked at the floor.
“Well we are not nasty, we will not bite, harder than you can stand anyway” Anna said as she put out the do not disturb sign and locked the door.
Before the poor girl could say no Anna and Mindy were sucking her face and neck and undressing her. Lulu came over and fastened my legs and wrists with cuffs and then secured me in a chair where I sat and watched as they fed on and fucked this young girl senseless. Trudy (the room service girl) cried the whole way through the relentless attack on her body but mysteriously never put up a physical fight came over and over again and then stopped crying. The girls had all fucked her silly but she looked across the room, at me and said “What’s the matter boy, don’t you like pussy?”
I felt Lulu’s hand grab the hair on the back of my head and push my face into the beautiful shaven cunt and started sucking and eating her out. Having already cum for each of the girls I knew my work was cut out for me and after 20 minutes soled of eating pussy and giving it all I begged for my hands to be released.
Lulu agreed and freed my hands. Within no time I located her precious and sensitive G-spot inside her beautiful pussy and began rubbing it while I sucked her clit in and out of my mouth. I flicked and sucked her lips and cherry until finally she came for a fourth time. The whole time tears streamed from her face but no resistance came.
“Are you ok Hun?” I asked
“Silence slave” Lulu ordered.
“Speak girl, why are you crying?” Lulu barked
“It was beautiful. I have never even dreamt of such an amazing experience yet. Thank you, thank you. I do not know what else to say but thankyou”
Lulu did not respond verbally but just kissed her on the forehead and whispered in her ear. I am not sure what she said but it brought a smile to her face and made her blush so I guessed we were safe from rape allegations for now. She dressed and left the room quickly and we never saw her again.
“Slave, lie in the middle of the bed on your back please”
Of course I followed my orders. My mind was a mess of orders and outcomes and it seemed that whatever these girls wanted they got. The fact that I enjoyed every one of their outcomes helped me to lean toward obeying Lulu’s orders and then in the end going through with them.
Once sprawled down the centre of the bed Lulu cuffed my ankles and wrists to the foot and head of the bed. My hands were cuffed together but my feet apart. I assumed that was to give the girl’s access to my ass, I was right.
Minny climbed in between my legs and slapped her Humungous cock up against mine making it look simply pathetic. She covered her glorious shaft with liberal amounts of lube and then entered my tender ass and began thrusting ever so slowly. I bit my lower lip and eventually got used to her gigantic cock in my ass. When the pain subsided and I was used to her massive cock Lulu straddled my face and thrust her cock down my throat and slowly pumped in and out of my mouth.
I had never experienced a gang bang before but was rapidly coming to appreciate the idea. My ass was full of gorgeous shemale cock and so was my mouth. All that was left was my cock flopping around in the breeze. Anna quickly provided the solution to this problem by gobbling up my throbbing cock. So now I had a gorgeous woman hammering my ass to oblivion, sucking my cock like there was no tomorrow and sliding in and out of my mouth like we were the only people left on earth and it did not matter. In my mind it could not get more perfect than this. We rocked and rolled, bobbed and swayed and moved in perfect unison like a well oiled machine for a long time.
Anna tired of sucking my cock and decided to mount my still rigid shaft. Now picture this, 3 near perfect Transwoman and 1 man. The male being fucked by 1 shemale with an insanely large cock while another shemale with a tighter ass than a 5 year old bouncing up and down on his cock while a third gorgeous shemale is force feeding him pork sword a plenty. My body had never known so much ecstasy.
We moved in perfect unison, rocking up and down. Round and round. Side to side and in and out. Despite the occasional rotation of the T-girls we moved like a well oiled machine for a long time. Eventually we collapsed, tired and exhausted from sexual over exertion and lay together trying to overcome the experience of a lifetime.
When I awoke in the morning the girls were nowhere to be found. Actually there was not a trace of their existence other than a note that read “Next time you’re the boss, love Lu, Anne and Minny”