The Breaking of Victoria Price

Story Info
Crossdresser has first experience with sex.
2.3k words
4.39
91.4k
12
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 had met Jarred in a chat room and we had been on-line for a number of months now, however there was still a great deal of apprehension about me for filling my fantasy of being dressed as a woman and being with another man. I have been dressing for some time and have managed to build a large array of nice things including heels, wigs, dresses, makeup and especially lingerie. I enjoyed the opportunity to be with him on cam and on-line together and during our time we have explored each other bodies and masturbated. I had also used a vibrator on myself as he directed me I simulated him entering my two openings.

I had also managed to keep my secret from my wife Judy of some 14 or so years and took every opportunity to dress whenever she was away. My room was located down stairs and she would only enter when invited to do so. I spent a great deal of time there and Judy didn't mind in the least as it kept me out of her hair. Jarred had convinced me to be on cam and I had also taken a great number of pictures of myself for him dressed in all my pretty things. He had continued to insist that I should meet someone and he would love to see pictures or even live on cam, me with another guy taking cock in my mouth and also being fucked. There was still that whole AIDS thing which frightened me and I couldn't bring myself to go through with it. I was becoming more and more consumed with the thought of going all the way with my fantasy.

Jarreds request for a real meeting with someone else was usually the main focus of our chat and it was during this last time on-line time together he had sown the seed. He told me that there were escort agencies that had male escorts who would do what ever for payment and that this could please us both. He told me how much he wanted and loved me that I was his girl and if I loved him I would do it. I finally agreed to his request and that by the time we were on line next I would have done what he wanted.

Nervously I made the call and spoke with an escort from the agency. Dominic seemed very pleasant and explained that he was more than happy to help me. He also offered to bring a friend who could take the pictures I required. We agreed in principle that the photos would be erotic with only my face in them and that there would be some of me looking at his cock and others with me pretending to lick it and with it resting on my cheek. I informed him that there was no way that I would be taking any one in my mouth and that there was no chance of him taking me in the arse. He agreed to my requests and for the rest of the week I was on tender hooks as I waited for the weekend to arrive

It was Saturday and Judy would be away. I booked into the hotel early and laid out the pretty things I would wear for my photo shoot.

Jarred liked me in black and I would dress for him. Black lace panties and bra,together with black lacetop stockings and heels. I would be blonde with peach eyeshadow and pink lipstick. I had convinced Judy to let me have my ears pierced so I would wear large gold hooped earings. I took a long hot bath while sipping champagne which would relax me as the hot water would soften my body. I was smooth all over as I had removed all traces of my body hair prior to my arrival. Dominic would be here at 5 PM and I would be ready. I drank a few more champagnes and was very well relaxed as I dressed and applied my makeup. I had just put the finishing touches to it as a knock at the door broke the silence.

I opened it to find a tall handsome young man standing before me. Beside him was an older man with a receding hairline and he was a little overweight. In his hand was a camera case and I assumed that he was the photographer.

"Hello' enquired the tall stranger.

"I'm Dominic."

"Hi" I stammered.

"I'm, ah Victoria."

"Nice to meet you Victoria."

" Can we come in?

I ushered the two men into the hotel room and locked the door behind them.

"This is my assistant Max."

The man reached out his fat sweaty hand and I shook it after which he went about his business of setting up his equipment.

"Well Victoria may I say you look lovely."

I felt myself blush as I thanked him for his compliment.

"Could I join you for a champagne?

I took a glass and poured him one from the bottle. All the time his eyes roamed my body as he sipped his champagne.

"So tell me are you doing this for yourself or do you have a friend?

"I have someone who wants these photo's and I'm doing it for him."

"May I ask a personnel question?"

"Ok."

"Have the two of you been intimat?

His question surprised me a little.

"NO, no we haven't."

"He is my on-line friend" I replied.

"Well he is a very lucky guy to have someone as pretty as you."

I felt myself again blush as I took an even bigger gulp of my champagne.

The silence between us was broken when Max informed him that he was ready.

Dominic took the glass from my hand and taking my other hand led me to the bright lights.

"Now I know what you want so why don't you do what comes natural and Max will shoot it ok?'

I shook my head and also acknowledged Max's direction.

I moved to my knees in front of him and the flash of the camera now took over. I pressed my hand against Dominic's crutch and could feel his cock harden as I massaged it through under the material. Max began to direct me from the side as he continued to snap away.

"Reach up and unzip him."

My hand shook nervously as I reached up and I grasped the zipper between my thumb and fore- finger. I slowly pulled it down with the sound of the zipper echoing throughout the room.

"Now reach inside and take it out."

I found myself again complying with his direction.

"That's it now stroke it."

"Stroke it long and hard."

"And smile, like your are enjoying it."

I felt my lips smile and I gazed at his young and thick black cock.

I slowly began to masturbate him as the camera continued to capture every single moment. The champagne had completely relaxed me, as I beginning to feel very light headed.

"Now move your head and mouth forward."

I again complied with Max's direction as the bright flash of the camera-exploded time after time.

"Oh yeah baby that looks hot, now stick out your tongue."

My lips parted and my tongue darted out almost touching his stiffened cock.

"That's it Vicky look at it long and hard like you want it."

"You look so fucking hot."

I was beginning to enjoy my new experience as I wanted to be a part of it and my hand had quickened its pace.

"Put those pretty lips closer."

I was beginning to become a little hesitant, as it seemed to be almost touching my tongue, but again followed Max's direction.

"Put your mouth on it" he hissed.

I turned to look at him.

My expression told the story that I was not impressed at what he wanted me to do.

"I told you I'm not doing those sort of shots."

"Honey I wasn't asking you bitch, I was telling you to put your mouth on his cock."

I pulled away and was about to get up when I felt Dominic grab my head and pull my face to his gaze.

"Listen to me very carefully Victoria."

"You will do what you are told to do and you won't get hurt."

"Or if you don't I will beat you good understand."

My mind raced, as I knew that he was in control.

"Oh god no please Dominic, please don't make me do this."

"I've never done this before."

His hand struck my face hard and sent a stinging sensation throughout my body.

I needed time to think.

"Oh god please don't hurt me Dominic I'll do what you want."

"Oh I'm sure you will Victoria."

"You see Max and I intend to fuck your pretty holes real good and you are going to enjoy it."

Tears began to fill my eyes as I could see the evil grin on Max's face.

"Now you will do what Max tells you and you will take my cock in your fucking whore mouth."

I nodded in acknowledgment as I opened my lips and mouth and then felt him pull me head to his cock. I felt his cock slide over my lips and into my mouth, where it pressed against the back of my throat. He held my head tight as I fought hard to breath. Dominic began to pull my head back and forth on and off his cock, using it to pleasure himself. The camera stopped as I could see max from the corner of my eye hurriedly undress. He now joined us as Dominic withdrew his cock from my mouth and Max moved into position.

Max immediately grabbed my head and pulled it to his placid cock.

"Open your mouth you fucking whore."

I again complied with his order and soon found my mouth again full of cock. He pushed it down my throat forcing it deeper with each thrust. I gagged and fought hard not to choke as he continued to rape my mouth.

Dominic grabbed the camera and was taking pictures of Max with his cock buried deep in my oral cavity.

"God this bitch's mouth is so fucking hot."

"You were right Dom, this cunt sucks better that my misses."

"I'm gonna enjoy shooting my load down her slut throat."

I was now their new fuck toy and soon realised that I would be here for a long time while the two of them used me.

"Bring her over here so we can both get off in her" yelled Dominic.

Max pulled out and grabbed my wrist hard dragging me to my feet I stumbled toward the coffee table where Dominic grabbed me and they lifted me onto it. My head hung over one end and my bottom over the other. They grabbed my wrists and ankles and using some tape secured them to the legs.

Dominic moved between my open legs and Max moved back to my head. He again grabbed it and steered his cock to my aching mouth. It was again full of cock as Max thrust in and out of me. Dominic grabbed a hand full of my black lace panties and tore them from me, exposing my virgin opening. He greased his cock and I then felt the head against my anal opening. He began to push and I could feel the resistance. I cried out however my cries were muffled with a mouth full of cock. Dominic began to push and his cock was beginning to enter me, pushing past my sphincter. My screams became louder as his cock was tearing its way into me,stretching me wide. His eyes were full of lust as he seemed to enjoy giving me pain. It was almost half way inside me and he wasn't finished yet. He pulled out and then thrust forward and it was becoming easier for him. His balls gently slapped my buttocks as he continued his assault on me.

I was now there bitch and all thought of me not being forced to suck cock and be fucked was well and truly long gone. My senses were returning as I could taste Max's precum and could feel Dominic fill my anal hole. I knew they intended to cum in me and that they would also exchange places once they had become hard again.

"Oh fuck Dom I'm so close to fill it's mouth with cum."

"Her Fanny is so fucking tight as well."

"Your gonna enjoy fucking it Max."

I wasn't prepared as I felt Max's cock twitch and with one more shove his cock exploded in my mouth. It caught me by surprise as so much soon filled my mouth. It gushed from my lips and spilled down over my nose and onto my forehead. He continued to expend it all thrusting deeper with each spurt. I struggled to breathe and gag, as I didn't want it in my belly.

"Swallow it you bitch" he hissed as he pulled hard on my nipples.

I opened my mouth further and felt it slip down my throat. It tasted vile as it made its way to my stomach. The sight of seeing Max cum now tipped Dominic over the top and with one last thrust he too exploded in my anus. I could feel his seed spurt hard, deep in my bowel as he thrust one last time. His cock began to soften as he pulled out of me and I felt his cum ooze from my opening.

Max had taken the camera and was now shooting pictures of my cum filled body. I had been broken in and they would in time release me. I was forced to shower and apply new make up. There was no need to be secured this time as I was now a willing partner and would be again serviced by the two of them. Susan must have thought it strange as she watched me hobble, as I was too sore to walk after the fucking I had been through. Jarred loved the pictures and liked the thought that his bitch had been fucked and that I would be well prepared for our eventual meeting.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousover 10 years ago
you want it don't you

I bet you really wanted to suck his cock all along. Don't try to say that you dress up in sexy women's clothes but that you don't want to act like a woman. I know that whenever I dress in women's clothes it makes me feel so feminine and horny that I can't get enough cock in my mouth or in my man-pussy. All of us sissy bitches are all the same -- we are cock-sucking sluts who love to have men with big cocks use us to get their rocks off. Welcome to the club !!!

AnonymousAnonymousover 11 years ago
please continueq

I can't wait for the next chapter to this story. Looking forward to reading about you and your lover. It makes me want to do exactly what you are doing - - suck cock and get fucked while dressed in my sexy clothes.

AnonymousAnonymousover 15 years ago
hot

my first night in he big city i slept well, dreaming about what mightsoon occur. as an 18 year old who loved women but was a virgin, i also knew i was attacted to mwen. i had heard about a porn theater where i might see some action. showeringm, shaving the little hair i had on my body, i was trembling with excitement. i wore a tight tank top that slightly showed byrather full breasts and large nipples, grown from years of masturbation. i fould the nearby theatre, paid and entered, excited. i found a seat in the back row and was surprised to feel someone almost immediately sit next to me. he said hellow honey and i felt his hand grasp my cock. i jerked and came instantly. he said you are a hot luittle slut arent you. i felt my head being pulled down and his cock enter my mouth. soon afterm there were nands all over me and a funger was probing my ass. they started to undress me. i hesitated but was told everything was safe in the theater. i spent the whole day there. i dont know how mant delicious lloads of cum i swallowed. my ass was fucked so raw i limped asi wa;led home. now as my cock gets hard remembering that day 40 years ago, i wish everyony had the thrill of being fucked and used without the worry of aids. even now im happy to have a cockin my man cunt, but its not the same without the complete feeling of being filled with hot cum. oh, i stil;ll love the taste of a hot cunt and a genberous mouth full of girl pee.

Share this Story

Similar Stories

First Time Being a Woman Crossdresser experiences being a woman.in Transgender & Crossdressers
The Perfect Age Ch. 01 Young man begins his journey as a young girl.in Transgender & Crossdressers
Like Mother, Like Sissy A sissy learns he is a princess . . . and a sperm whore.in Transgender & Crossdressers
New Job, New Life as as Sissy Slut Man gets a job cleaning a house, but gets much more!in Transgender & Crossdressers
A Helping Hand An offer to help leads to an unexpected transformation.in Transgender & Crossdressers
More Stories