tagTranssexuals & CrossdressersFirst Time Being a Woman

First Time Being a Woman

byregina_allen55©

My heels clicked on the concrete path as I made my way toward the secluded toilet block in the southern parklands. Tonight would be my first experience being with a man whilst I would be dressed as a woman. I had been dressing now for some time and had fantasised about what it would be like. I didn't know anyone in my own personnel life and had read in the paper that men came to the block to get sex from other men. I was so nervous I could feel my body tremble as I approached the doorway. I took one more look around before I entered.

I had selected something conservative for that evening with a grey short skirt and matching jacket with a white blouse. Under it I wore a white lace bra and panties with sheer pantyhose and white heels. I was blonde to night and wore peach eye shadow and pink lipstick. I had also applied an extra coat of lip-gloss. I could feel myself becoming aroused as the softness of my panties rubbing on my own cock with each step that I took. I made my way into the vile smelling place and waited for my eyes to adjust in the dimly lit ablutions.

The lighting was ultra violet and there were about five cubicles which ran down one side of the building at the far end was the figure of a large male who stood smoking a cigarette as he leaned against the wall. My throat was dry as I attempted to make conversation.

"Hello," I smiled.

"My name is Janette."

"Well hello Janette," came his reply.

"So Janette, what brings you here?"

"Well I don't really know," I stammered.

"Then let me help you Janette."

"Do you give or do you receive?"

"Ah, I, Ah give," I gain answered neverously.

"Have you ever had cock in that slut mouth of yours Janette?"

"NO."

"Well now a first timer," he laughed.

I was beginning to tremble at his questions and I was now not so sure as if I really wanted to go through with it.

"Look I think I may have made a mistake," I said nervously.

"I think I should go."

"Oh I don't think so Janette," he hissed.

It was then that I realised that there was a second person standing behind me preventing my departure.

"You see Janette, Mark here and I are looking to have our cocks serviced and I think your just the girl to do that for us."

Fear gripped my body as I now realised that there was no escape. I had heard there had been a number of bashings at the toilet block and I knew that if I put up any resistance that they would hurt me. I needed to try and gain control so I tried to take the initiative.

"Please I, I will do what you want only please don't hurt me."

"Oh Janette I'm glad you said that because we would really hate to hurt you."

"Now why don't you come over here and show me what you can do to satisfy me. I was like a robot as I walked toward him. I was soon on my knees on the cold hard cement floor and I reached up, grabbing the zipper on his trousers and slide it down. I reached inside and pulled his cock free. It immediately began to stiffen as I slowly stroked it.

"Oh yeah Janette that feels real good."

"Now use that pretty tongue and lick it for me."

I opened my lips and my tongue darted out where I slowly licked the head of his cock. It tasted salty and there was also the taste of precum mixed with his sweat. I tried not to gag as I ran my tongue down the shaft and then back to the head.

I could hear him moan as I worked my tongue around his cock head and then again up and down the shaft. His hands gripped the back of my head and he was now in control.

"Oh yeah baby that feels so fucking hot."

"Put your mouth on it."

"Put that cock sucking mouth on it you fucking whore."

He was becoming aggressive and I knew that if I didn't please him I would suffer.

"Mark, this bitch knows how to suck."

"You have done this before haven't you Janette?"

This was my first time and I wasn't enjoying the experience one bit. I was hoping to find someone a little more accommodating and not some red neck.

He held my head tight and pushed his cock against my painted lips. It soon pushed past them and into my mouth. I felt it hit the back of my throat and I fought hard to control my gag reflex. He began to pull my head on and off it and he was soon fucking my mouth. I began to whimper as he pushed his cock deeper down my throat. It wasn't long before his balls slapped my chin with each thrust into my oral cavity. I was soon deep throating him and I had managed to prevent myself from gagging.

His intensity now increased as he thrust into me, raping my now willing mouth. I felt dirty and cheap and now knew what it was like being a woman and being forced to give head.

His cock began to twitch and swell and I knew he would soon climax in my mouth.

"I'm gonna cum real soon bitch and your going to swallow every last drop."

"If I see you waste any I'll fucking hurt you bad."

I positioned my tongue so as to allow his seed a better opportunity to flow down my throat. This would be the first time that I would taste cum and also the first time I would swallow. I won't gag I told myself as he was now on the brink of climax. With one last thrust I felt his cock buck and then it happened, it exploded in my mouth. I gulped it down, forcing myself to swallow his seed. It tasted strange like tin as I continued to swallow again and again. I had never seen anyone cum so much. He held my head preventing me from pulling his cock out of my mouth until he had expended every last drop. As he released his grip on my head I slumped to the cold hard floor coughing and spluttering like some freshly landed fish. I lay motionless as he pushed his cock back into his trousers and zipped himself up.

Time passed and I hoped that they would leave however there was now the second man who would need to be satisfied. I thought that he too would want to take my mouth only he had other ideas. He bent forward and grabbed my wrist, pulling me roughly to my feet. He steered me to the end cubicle and pushed the door open. He reached into his pocket and pulled out two thin plastic ties. He took my wrists and pushed them down to the pipe which ran behind the seat of the toilet. Next he used the plastic to secure them tying on to the other around the pipe. I stood on my heels and he completed his work. The tearing of some black duct tape filled the cubicle as he applied the piece to my mouth.

"Now bitch you will stay on your feet or I'll fucking beat you,"

"Understand you fucking dirty bitch?"

I nodded my head in acknowledgment of his orders and he moved behind me and he grabbed the hem of my skirt pulling it up around my waist. I could hear and feel his fingers tear a small hole in the back of my pantyhose. He inserted his finger into the hole and pushed the elastic leg band of my panties, which ran around my thigh. My anal opening was now exposed and I knew that he intended to fuck me. This was not part of my plan as I struggled against my bindings and screamed into my gag for him not to do this.

"Yeah bitch you got it right."

" I gonna fuck your cute tail and your gonna enjoy it."

I began to sob as I heard the sound of his zipper being undone. Next there was the sound of him spitting into his hand after which he applied the saliva to his rod. I now felt it against my anal opening and it slowly began to push against the resistance.

The pain was intense as he again pushed into me. My sphincter was preventing its entry only I knew it wouldn't be long before I would be impaled on his monster. He continued to push into me and his cock was slowly gaining entry. The head had pushed past my opening and was now on its way to where he wanted it to be. It slowly inched its way deeper and deeper as my anal tunnel gripped it tightly. I thought I would black out as the pain was now burning my insides. His monster was tearing me open and I knew that it would wreck my anal cannel and the damage would be permanent.

His cock was now almost completely into me and the pain started to ease. He gripped my hips tight and pulled back the shoved it forward. Finally his balls slapped my buttocks letting me know that he was now fully inside me. He now started to fuck me, riding me like he would his bitch. I was impaled on his cock and he was in complete control.

"Fuck Janette your man pussy is so fucking tight."

"I'm so glad that I'm your first."

He was now fucking me and the pain was less and less. He started to pound my sore arse and his hands reached around to my crutch. He took the soft sheer material of my pantyhose and tore them open. He reached inside my panties and pulled my cock free. He began to stroke me in rhythm to his cock, which now slid in and out of me.

"Come on baby get that cock nice and hard for me."

"I want to feel you cum too while I fuck you good."

My cock was becoming hard as he stroked it forcing more blood into the shaft. I was now being turned on at the thought of being his bitch and being raped in some dirty place against my will. I was pushing my bottom back into his thrusts and my body was now a willing object of his advances. I wanted to be fucked and I wanted to cum. I could hear myself moan into my gag as he pushed and pulled his cock in and out of me.

His rhythm intensified and he was now close to shooting his load into me. I too was now so fucking close and I wanted him to finish me off. His next thrust would do the trick as he cried out the first lot of cum shot deep inside my bowel. At the same time my own cock exploded and I shot my load all over the toilet set in front of me. He continued to fuck me making sure that every last drop of his cum would remain inside me.

He had finished and pulled out of me. I could feel his cum ooze from my anal opening. He cut the ties from my wrists and in an instant both me were gone. I adjusted my dress and tried to fix myself up.

I made my way slowly back along the path where I managed to hail a taxi. It was difficult to sit, as my bottom was sore from my anal rape.

When I arrived home I took a long hot shower and washed their seed from my body. I slumped into bed and my mind re-lived my first experience. I knew that in time I would return to the block for another taste of being a woman.

Report Story

byregina_allen55© 10 comments/ 167509 views/ 8 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartRoadog1, stehlen1 and 6 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous08/30/14

Kinky

It's kinky I always wanted a guy to cum in my ass. Btw what color were your pantyhose? Keep on living free you got respect from me takes a lot of guys to live free in this cruel world.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous06/09/14

oh yessssssss

I'm still hard 5 minutes later,wishing that was me

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous01/20/14

wow!!

now that made me hard ..........and jealous....that's how I would like my first

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 10 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel