My First T-Girl Date with Lauren

Story Info
My first date experience with t-girl Mistress Lauren.
2.5k words
4.11
48.7k
17
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

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 here

I was sitting in my car outside of Lauren's house fixing my makeup and making certain that my dress and thigh highs were just right so that I would make a sexy impression on Mistress Lauren at our first meeting as she had instructed me in our internet correspondence. I was playing with my wet pussy and glanced down at my watch and realized that I was now nearly fifteen minutes late for our date -- I only hoped that I would not displease her for being late.

Getting out of my car I made certain that my dress was very short and sexy and I hoped it would impress my dear Lauren. I walked up the sidewalk and stood at the front door ringing the doorbell to her house.

Mistress Lauren opened the door and I had a hard time believing the vision of loveliness standing in front of me. Towering above me in her 6-inch CFM black patent leather high heels was "Mistress Lauren" in a black leather bustier with red garters and very sheer black stockings.

"Bitch why are you late for our date!" were the first words out of Mistress Lauren's beautiful mouth as I stepped inside the door. She slammed it behind me and locked it so I could not escape!

I saw that Mistress Lauren's shecock was beginning to get hard and erect so I made the first move and reached out and took it in my hand and started to stroke it while at the same time I gently kissed her bright red lipstick covered lips in a hope to appease her anger at me for being late so late.

The next thing I felt was a hard backhand slap across my face that sent my head spinning!

"What the fuck are you trying to do to me Victoria, you blonde haired slut bitch!"

"I am so sorry if I offended you Mistress Lauren but I was only trying to please you and get your shecock hard so you could use it on me" I replied to her demanding question.

Grabbing my long blonde hair she drug me across the room to a black patent leather covered chair and bent me over the back of it. She spread my black nylon covered legs apart and attached each one with a handcuff to the legs at the bottom of the chair.

Walking around to the front of the chair she grabbed my hands and pulled me down so that she could next attach my hands with handcuffs to each leg of the front of chair. She now had me ready for my lesson on being late for our first date. Tears began to run down my cheeks because I realized that I was going to be punished for my tardiness.

I felt so helpless in this position. I was standing on my tip toes and completely available to Mistress Lauren's whims at this point. She pulled my little black dress over my head so that I could not see what was going to happen to me next. She ripped my black bra off and my "DD" boobs were hanging down over the seat of the chair.

My next embarrassment was seeing Mistress Lauren pick up a pair of her used black silk panties from the arm of the chair and stuffed them in my mouth forcing me to taste her dried juices and other matter.

Suddenly my nipples were on fire as my angry Mistress Lauren clipped nipple clamps on them and then the pain began to get intense as she attached 12 oz. lead weights to them to stretch my tits down. I had never felt pain like this before.

"Well my little blonde-haired slut bitch it seems that you have gotten my shecock hard before I told you to do so."

"Now you are going to suffer the pain it brings to your tight asshole as it stretches you out so you can receive a special enema to warm up your insides before you drink something special of mine down."

Mistress Lauren began to finger fuck my tight asshole and next lubed my tight little asshole up with some KY and before I knew it I felt her erect shecock slide slowly inside my ass and fill me up with her rock hard meat.

Mistress Lauren began to pound her rock hard shecock in my ass and I felt the pain as my asshole was stretched wide open for her. After what seemed like an eternity suddenly the pain stopped as she pulled her shecock out of my ass. My asshole felt like it was twice as big as usual.

After a couple of minutes I felt something hard and plastic being inserted in my asshole.

"Well my blonde bitch I am going to fill you up with some red wine so that you can warm it up for me and drink it down later when I am done with you."

"You better not let any of it spill out of your ass and on my carpet either."

I felt my bladder being filled up and then as suddenly as it began the hose was pulled out of my ass. I squeezed my ass muscles as tight as I could so that none of the warm red wine would escape. Suddenly I felt my asshole being stretched wide open again as Mistress Lauren inserted a black inflatable rubber butt plug in my asshole.

Mistress Lauren next attached a tube to it and began to pump it full of air so that it sealed my asshole nice and tight so the wine warming inside of me would not escape.

Mistress Lauren next turned her attention to my dripping wet pussy.

"Well bitch I bet you thought that I was going to fuck your cunt next with my rock hard shecock didn't you?"

The next thing I knew Mistress Lauren was pounding my cunt with a huge black dildo that she had picked up from the table by its attached handle. In and out and in and out she pounded away inside of my cunt until I began to beg her to stop. Tears flowed freely from my eyes even though I could not see what she was really doing to me. Mistress Lauren shoved the twelve inch dildo as far inside my cunt as it would possibly go and then using some duct tape she sealed it inside of me. I was glad that I had shaved my pussy this morning for Mistress Lauren.

Coming around to the front of the chair Mistress Lauren once again pulled my little black dress over my head and down my arms. She stood close to my face and began to slap my cheeks with her rock hard shecock.

"I bet that you like that don't you cunt."

I weakly replied "Yes Mistress Lauren".

The next thing I knew Mistress Lauren began to cover my face with a stream of her hot yellow elixir. She made certain that I tasted her yellow elixir too.

"I bet you thought that you were going to get a cream pie facial didn't you my little blonde cunt bitch."

Mistress Lauren then pulled my little black dress up again and cut it to pieces with a knife and wiped my face dry with the remains of it. She also made me lick her shecock clean too as the humiliation continued.

Next, in order to show me that she was truly in charge of me Mistress Lauren began to slap my face with a backhand slap first to one cheek and then to the other cheek. She varied the strength of each slap and continued this for at least fifteen minutes as my mind began to go in and out of it. Suddenly I received one very hard slap and the next thing I knew my mouth was filled with a red ball gag and it was tightened tight.

"Let's see how you handle having your back whipped my little cunt bitch."

"Will you beg for me to stop or not?"

Mistress Lauren laid a cat-o-nine-tails across my ass and came around so that I see her again. Stroking her shecock again since it had begun to soften and go limp she put a leather cockring on it as it once again swelled and stood at attention ready to fuck me again.

"Are you ready for this to go inside you again bitch?"

"It will be nice and hard and ready for you when I am ready to fuck you again."

Picking up the whip Mistress Lauren began to slide it across my ass. I did not know when she was going to start whipping me but I was wiggling back and forth every time she picked up the whip and slowly rubbed it across my back and ass.

After what seemed like forever Mistress Lauren began to whip my ass first. Stroke after stroke I felt the strands of the whip cut into my skin and set my ass on fire. Next my back and then my shoulders are whipped over and over until they felt like they were on fire too. I eventually passed out from the pain of the whipping. Deep down inside of me I deserved the whipping because I was late for our date.

I don't know how long I was out but Mistress Lauren brought me out of it by rubbing my ass with a handful of ice cubes which was not only painful but made me tingle all over. She gently slapped my face a few times until she was certain that I was ready for more or her evil desires!

Once again standing in front of my face Mistress Lauren instructed me to lick her hard shecock until she was ready for me to stop. I suddenly felt two additional pairs of hands begin to squeeze my ass and play with my pussy.

I was not certain what was going on until Mistress Lauren's two beautiful t-girl friends walked around in front of the chair and the three of them stood there in front of me stroking their shecocks and getting them ready for me. I could not believe how beautiful the three of them were. As always Mistress Lauren dressed in black except for the red garters and stockings that I had sent her as a present to wear on our first date. Her two beautiful t-girl friends were wearing nothing but babydoll nighties, one red and one teal. As their shecocks were getting rock hard they too put leather cockrings around them so that they would stay as hard as Mistress Lauren's.

Mistress Lauren told me that her friends had been watching her torture me and were now going to help her fuck me and let me experience my first triple penetration with nearly two feet of shecock meat. I did not know what was going to happen to me now.

First, I felt the pain of the duct tape being ripped off of my cunt lips and the dildo being slid out of my throbbing cunt as my juices began to drip out of it. Next Mistress Lauren let the air out of the butt plug and slowly pulled it out of my asshole making certain that I was uncomfortable the whole time.

I could not hold the warm wine inside of me any longer but just as it started to flow out of me Mistress Lauren caught every drop of it in a glass pitcher which she had sitting on the table beside the chair. She filled a wine glass full of it.

Next Mistress Lauren took the ball gag out of my mouth and grabbed a handful of my long blonde hair pulling my head back and instructed me to drink my warm red wine. It had a funny but earthy taste to it now but I drank it all down as she instructed me.

"Well bitch are you ready to be fucked now?"

I weakly nodded my head yes and began to anticipate what was going to be done to me next. Mistress Lauren placed an ottoman between my legs and one of her t-girl friends got on it and straddled my hips slowly inserting her 8-inch rock hard shecock inside my asshole.

Mistress Lauren's other t-girl friend stood behind me and filled my cunt with her huge rock hard shecock too. Once again Mistress Lauren stood in front of me grabbing two handfuls of my long blonde hair and slid her hard shecock inside my mouth.

"If you don't give me the best blowjob of my life you will regret it forever my blonde bitch."

Mistress Lauren and her two t-girl friends began to slide their shecocks into me slowly at first but after a few minutes they began to pick up their pace filling my openings. I wrapped my tongue around my Mistress's hard shecock and scraped my teeth up and down the shaft of her shecock as she pumped it in and out of my mouth. I assisted her pumping it deep inside my mouth by sucking hard on it with her every stroke. I continued to lick and suck her shecock as the three t-girls fucked me for nearly an hour.

The three of them made me orgasm over and over more times than I can remember and I was quivering all over when the three of them suddenly stopped fucking me and pulled their shecocks out of my mouth, my ass and my dripping wet pussy.

The handcuffs were removed from my hands and feet and I was thrown on a sheet of black plastic on the floor. My nipples screamed with pain as the nipple clamps and weights were jerked from my swollen titties and they were slapped again and again by Mistress Lauren's two t-girl friends and pinched savagely by their long red fingernails.

Mistress Lauren and her t-girl friends now stood over me stroking their shecocks as they began to fill with cum! Removing their cockrings next they continued to stroke themselves to orgasm.

One after another they took turns cumming all over my face and tits. Mistress Lauren went last and after she came all over me she smeared her hands in the combined gooey mess. She then made me lick her cum covered hands clean!

"Well my little blonde haired slut bitch it is time for us to end our first date."

"I hope it is one that you will remember for a long time or at least until next weekend when you are going to be the treat for a party of my t-girl friends all weekend."

"You can leave my house with your purse, your thigh highs and pumps only."

"But before you leave we have one last thing for you to remember this night by."

And with that the three of them stood over me once again with their shecocks in their hands and peed all over me and filled my open mouth with their warm golden elixir.

After the three of them finished I got up and walked out into the night naked to my car covered with cum and piss from three beautiful t-girls that were standing in the doorway looking at their little slut!

I then drove home with a weak smile on my face and licking my fingers as I wiped up the remains of their fluids from my naked body.

I can't wait until next weekend...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 9 years ago
Powerful writing

Who knew a shecock, could be so wonderfully utilized in a story. The shecock is grabbed, but then there is a sexxxy price to pay. To me, the story centers on how they react to the use and access to the shecock, something I've not read before, and I've read many. The characters are there to do a sort of ring around the rosy around the shecock. It's just brilliant. The author should do a full legnth. In just this shecock-centric style. The characters are there to serve the shecock not thee other way around. Just splendid it is.

Share this Story

Similar Stories

His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
How I Met My Shemale Shy man dates a shemale.in Transgender & Crossdressers
Her Bulge The woman at the gym has a bulge in her spandex.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
More Stories