Taken The First Time

Story Info
Crossdresser is raped.
2.4k words
4.4
39.8k
24
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
TammyPanty
TammyPanty
1,174 Followers

I could not wait to turn 18 and move out on my own and live as the girl I knew I was. The week after my 18th birthday I had my own apartment and I had a full wardrobe of feminine lingerie. I also had a four poster canopy bed with a very feminine white top. It was the beginning of a dream for me.

Over the next two and a half years I did everything I could to feminize myself. I shaved all body hair away. In about six months it stopped growing back. I dressed every day in full lingerie and dresses. I put on make-up every day and got very good creating a "girl-next-door" look. I allowed my hair to grow and it was shoulder length in a shorter amount of time than I expected. I also purchased estrogen hormones I found online and began taking them as directed.

Because I was not taking the estrogen under a doctor's care I later found I was taking a dose that was very high, almost three times a normal rate. As a result my skin softened. My hips widened. And my breasts showed a slight increase in size. To my total delight, any form of erection completely stopped. My penis was permanently limp and it began to shrink noticeably. All wet dreams ended and any attempt to ejaculate ended without anything at all. My testicles shrank to next to nothing in less than three months. Sexually I was becoming a girl and becoming one very easily and much quicker than I imagined.

At just over twenty years old I had only ejaculated semen from my tiny penis twice in my life. Both times I squirted the sticky white cream into my hand to see what it looked like. I did not like the sex act of ejaculation at all. On the second ejaculation I did manage to lift my hand to my mouth and to lick the mound of white cream. I found I enjoyed the feel and taste of the cum and I was able to take in and swallow all the hot, puffy, semen from my palm. I later considered this my first sex act as a girl.

I wore a complete set of overly feminine lingerie on a daily basis. I wore a dress every day I and always wore make-up. I did have a guilty pleasure; I would leave the blinds in my bedroom window open when I was dressing in the morning. My penis had shrunk almost out of sight, so when I was naked getting out of the shower, it was very difficult to tell from a distance I was not a female. I had no body hair and nothing between my legs that could be seen. My breasts looked small, but feminine.

Outside I passed in public with ease. My voice was slightly higher and did not sound masculine. My look was fully female. I wanted to push things farther and I made arraignments to have surgery for breast implants. I was careful not to have the implants interfere with my sexually sensitive nipples. Just about all my sexual pleasure came from my nipples. The doctor assured me the implants would only increase my sexual enjoyment and it was decided that my completed bosom should be a size 38C.

The surgery was easier than I anticipated as it was done laparoscopically leaving only a tiny line in a fold of my armpit. My recovery time from the surgery was less than a month. My finished breasts looked wonderful and I loved lowering them into my pretty satin and lace bras every morning. In the evening, it was fun to unhook my bra and let my breasts dangle free. I was a fully functioning and totally natural girl and I could not have been happier. If someone was looking through my bedroom window while I was naked and dressing they would enjoy a very pretty girl getting ready for the day.

I knew there were other windows in my apartment complex that could see into my bedroom window but I did not look out my window as I got dressed each day, I just hoped I was being seen by someone who was finding me sexy. It was not very long before I found out this was true.

It was around 8pm one evening when there was a knock at my door. I looked through the peep hole and say a young twenty-something man in jeans and a white t-shirt standing there. He was very well groomed and had a young, handsome look. I was fully dressed in a knee length dress so I opened the door.

"Yes?" I said holding the door open just a little bit.

In that quick moment he pushed on the door and it opened against me. He was very strong and he quickly pushed his way inside closing the door behind him. His hand was over my mouth before I could say anything. I was a little bit scared.

"You little tease! Let's stop teasing and start some fucking." He said softly as his other hand caressed my breast through my clothes. My eyes filled with fear and he could see this.

"Oh honey...don't be afraid. I'm going to slowly take my hand off your mouth. Will you promise me not to scream?" He asked quietly.

I nodded my head yes.

"That's a good girl. Now you stay quiet as I move my hand away." He sneered.

As he removed his hand from my mouth I began to nervously breathe deeply. I kept my eyes looking straight into his eyes. He put his arm around my back and pulled me in closer to him. I must admit I liked the feeling and I liked the way he was taking charge of the situation.

"You're not going to hurt me, are you? Please don't hurt me." I said meekly as I was still fully dressed.

"It might hurt a little in the beginning, but you are gonna love the ending." He said with a sinister smile.

"I'll do what you want, just don't hurt me. I'm a special kind of girl." I said almost crying.

"I know that! I've been watching you for several months through the window. You are very girly and I know you have a really tight pussy for my cock. So let's get you undressed and ready for your new daddy." As he said this he began unzipping my dress.

As he unzipped my dress it fell to the floor around my ankles. I was wearing my very pretty set of lingerie which was a cream colored half-slip and camisole over nylon and lace full cut panties and a matching satin and lace bra.

"Oh, you're wearing my favorite set of lingerie! This is gonna be a very special fuck!" He said as his eyes got bigger looking at me.

"I'm a virgin at fucking! I have never done this before." I said quickly.

"Don't worry...daddy will show you how to please a man." He said with a smile.

I could see he was becoming aroused as there was a noticeable bulge between his legs under his pants. I began to get excited myself in anticipation of seeing his erect penis.

"Take off your slip and your camisole, and do it slowly. Let me see you in just your bra and panties." He demanded.

I did as he asked very slowly and was in front of him in just my bra and panties. My nipples became very engorged and erect and were clearly visible through my bra.

"Looks like you are enjoying what's about to happen little girl." He sneered with a smile.

"Looks like you are too. That's a pretty big bulge in your pants." I smiled and said.

"It's a full eight inches honey, and I'm only half-way there. Now let me see those beautiful tits. Take your bra off slowly."

I did as he asked and as my bra fell to the floor I put my hands over my enlarged nipples.

"Get your hands down! Show daddy your jugs. I want to see what I'll be sucking on later." He said gruffly.

I did what he said and followed by slowly lowering my full cut panties. When I stepped out of them I was totally nude and he was still fully dressed.

"You are beautiful! Just beautiful! And your special little clit is just that...it's just the size of a clit. Baby, you are one sexy momma. Daddy is going to love breeding you."

"Breeding?" I asked quietly.

"Yes baby. I'm going to fuck you till you scream." He said as he began to pull off his shirt.

"Now come over here and unbuckle my pants and pull them down. Show daddy you want what is in his pants."

I slowly approached him trying to hide the fact that I was getting really turned on. I undid his belt and then unzipped his pants and pulled them down to his ankles. He was wearing jockey shorts and his penis was getting bigger in front of my eyes as I quickly lowered his underwear. His ever growing cock sprang out in front of me and I dropped to my knees.

"That's right little girl. Wet daddy's cock before he fucks you with it. I want it to get as long and hard as it can so you can feel me inside you." He grunted.

I did not hesitate at all. I put my mouth on the still growing cock and began to lick the shaft with my tongue. My own tiny penis remained fully limp and retracted. His erect cock quickly grew to all of the eight inches he had bragged about.

"That's it baby! Get on the floor on your back and raise your legs and spread them for daddy. We're going to fuck like animals!" He shouted as he pushed me backwards.

"I don't really want to do this...You are so big! Can't I just suck on you with my mouth?" I said as I kept my legs down.

"No way little girl. You've teased me long enough and now daddy is going to fuck you and fill you with his seed." He said as he got on his knees and lifted both of my legs and spread them wide to reveal my very tight pussy.

"Please...Please...Don't hurt me. I've never had a man's cock back there!" I pleaded.

"Shut up you fucking tease and take my cock!" He said with authority as he lowered his rock-hard cock to my anus.

I looked down at the head of his cock and saw the hole in the tip of it begin to open as pre-cum began to ooze out. He moved it up and down my hole as if to lube it and before I could resist he pushed forward into my body. There was a very sharp pain as his cock helmet entered me. Fortunately, the pain gave way rather quickly to a feeling of pleasure as he slid deeper inside of me. I was being fucked in a way I never had experienced and I began to enjoy it even though I was being forced to fuck.

"You fucking little bitch! Take all of me and feel me cum inside you!" He shouted as he started to pound in and out of me.

"Oh my God...Oh my God, fill me with your cum!" Was all I could say as I gasped for breath.

He pushed as far as he could go inside me and then stopped as he lowered his mouth to my now enormous nipples. He put his mouth on my nipples and used his tongue to flick at them and I went wild with sexual excitement. My larger than normal mounds responded to his sucking and sent bolts of sensations all through my body.

"Oh suck me! Suck me harder! I feel like I'm going to cum!" I shouted in delight.

He sucked on me harder and then rose up and began pounding me again. It was the most physically taxing sexual session I had ever experienced.

"Take this you teasing bitch! Take it all! I'm going to fill you with sperm!" He grunted as he pushed deep inside me.

"Do it! Just do it! I'm about to cum too, and I want you to fill me up!" I gasped as I began to have muscle spasms and twitch in delight.

At that moment I felt his cock swell up and begin shooting rope after rope of hot cum deep inside my body. I was being fucked like a girl and I was enjoying the feeling after being very scared and being forced into intercourse. My tiny penis remained fully limp the entire time I was having intercourse. There was only a tiny dab of white, sticky semen covering the slit on my penis head that must have come out as I had the most intense climax of my young life.

My assailant kept his cock inside my body as he began to soften. I squeezed down with my butt lips to keep him copulated inside me. As he put his head down on my chest he gently began licking and lightly sucking on my engorged tits.

"That's it honey...calm yourself down and suck on mommy's tits as you do." I said in a baby voice.

I had been forced to have sex with a man I had never seen before and it was frightening at first, but now I was at peace having been pushed into intercourse. I actually felt myself wanting to have intercourse with a man this way again, but I did not want to let on to my attacker I liked it.

"That wasn't so bad, was it? You were a very good fuck. I've never had such an intense orgasm. And from the way you let me pound you it appears you liked it too." Said the attacker.

"I don't ever want to be forced to have sex like that again. If you don't hurt me, I'll say nothing and you can just leave." I sighed.

With that his penis fell out of my body and he got up from the bed and quickly dressed and left the room. I never saw him again, but I will always remember my first ever anal intercourse that was forced upon me. I now regularly engage in anal sex as my lone sexual outlet and it always pleases me and my male lovers.

TammyPanty
TammyPanty
1,174 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
AnonymousAnonymous10 months ago

Delightful. Reminds me of my first time except, I gave it up willingly. Also, hundreds of times since. Perhaps thousands. Who's counting? Being bred while on my back, always wearing nylons is heavenly. Always brings me to completion, too. Adult movie theaters, in vehicles. (Front seat from behind. Back seat on my back. Bent over the hood. ) Anywhere and everywhere, I can receive it. At just about any time my partner desires. I especially love it in the mornings. Sleeping in nylons and lingerie and being awakened by a turgid member against my lips before they position themself between my legs for a gentle entry into my well lubricated opening from the night before. I feel them enter and thrust to completion. Totally wonderful beginning of the day. Spending my day with their seeding in me looking for an egg to fertilize will keep me wet and ready for more. Feed me, seed me, breed me. Anytime, anywhere. All this is true. Some days I just can't get enough.

AnonymousAnonymousabout 1 year ago

Love it wish it was me

redfantasy72redfantasy72over 1 year ago

I liked it, was hoping for more resistance from her and not dressed slutty enough for me. All in all though was pretty good.

AnonymousAnonymousover 1 year ago
New Slut

Becoming was my dream for a long time.Now i have the female body i always wanted.With breast slim waist firm butt hairless body and now long hair.After doing my hair make up lips eyes and nails i was ready to dress.First my push up bra string thong High waist eight strap garter belt black ff seamed stockings and red six inch strappy stripper heels.Next a short tight red slip dress.My first date picked me up and thinking i was going out to eat he took me to a motel.Once there he stripped off my dress forced me to my knees and throat fucked me filling me with my first load of cum.That went on all night sucking and fucking me until i could not walk.

jay1459jay1459over 2 years ago

Great story -- thank you

Show More
Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Substituting for My Wife I substitute for my wife with her boyfriend when she's away.in Transgender & Crossdressers
Groomed to Depravity Ch. 01 A college boy's life goes awry on Halloween.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
More Stories