Lara & Jack to Melissa – the beginning

I am a 24 year old girl with long black hair always worn in a ponytail or a braid. I`m not tanned so my skin is white almost as white as snow and I have big green eyes. For my 5ft and 9” I have really long legs with almost 3ft 7” length. I have a nice round and perfect formed ass and I am very happy about my 38D.

I started masturbating really early at the age of 10. At the tender age of 13 I had my first sexual experience with someone else then me. But soon after my first encounter with malehood I recognized my interest for girls. At first I dated both boys and girls but after an incident in the gyms locker room with my best 2 friends I changed my sexual orientation completely to girls. Maybe I will tell you what happened some day.

After I left my parents’ house and got my first apartment I started to change my sex partners often. The sporty and always dressed in short or sexy clothes girl disappeared and my new style was born. Now I am a sexy vamp in stilettos, boots, plateau-boots, tights, catsuits, corsage, suspender, nylons, PVC, leather and latex. I even got tattooed and pierced.
Sometimes I wear trouser suits with white blouses, glasses and a Victorian braid because some of my girls like that. Because of my new found sexual preferences I bought many funny things… dildos, vibrators, butt-plugs, vibro-eggs, handcuffs, paddles, whips, strap-ons and many other toys.

But let us start with a nice little story…

On a party last fall I drank a bit too much so that I could not drive home. Because of that, Jack, one of my friends, invited me to his apartment to sleep there. It was a walk of about 10 minutes but we needed much more time. Being a nice guy I could sleep in his bed while he slept on the couch in the living room.
When I woke up at 9 am I needed a long hot shower. Because I needed a towel I searched his wardrobes. There were no towels but lots of clothes. Not only male clothes but also a lot of woman clothes. That was a bit irritating because Jack never had a girlfriend, at least non who lived with him. I decided to ask him later at breakfast why he had so many skirts, tops and even some shoes.
I started searching a towel again and after some minutes I finally found them. They were stored in a little wardrobe and I took one out. I heard something falling to the floor and as I looked I found some photos which were stored between the towels. “Why Jack stores photos between his towels?” was all I could think so I picked them up and looked at them.
I WAS SHOCKED!
On the photos there was Jack. Not really Jack but Jack in sexy short skirts completely done as a girl going out to party all night long. With breasts, bra, top, skirt, nylons, high heels, trinkets and even a wig.
I checked all of them and on every photo he wore different outfits. Different skirts, trousers, tops and even one catsuit he wore.
I have to say Jack is not a “sporty” guy. He has a slim body and is a bit smaller than me. Even his face is not a male one and he has no growth of beard. For everyone he is the typical IT-nerd and yes, he is an IT-nerd.
Not knowing what to do I decided to go showering and put the photos back between the towels. I went into the shower and started thinking about what I had seen.
After some minutes I started to feel that the photos of girly-Jack turned me on in some strange way.
I don`t know why but a man pretending to be a woman, actually a really nice one, made my nipples erected and even my pussy started to get wet. Not knowing why I started touching me. I softly pinched my nipples and caressed them while my other hand moved slowly down to my bald shaved pussy.
As my fingertips touched my clit, thrills shot through my whole body and I started to rub it. I pinched and rubbed it but after some minutes this wasn`t enough anymore. The other hands fingers moved down too to enter my slippery hot cunt. I fingerfucked me some more minutes while I still was rubbing my clit until I could not stand it anymore. My fingers started to search for the magical spot.
With my fingertips I massaged the holy G-spot. my massage quickly got more and more rapid, my breath got harder and my legs started to shake. I bit my lower lip so that I was not too loud and my eyes turned up as I cumed, shooting sweet pussy juice onto my fingers.
Shivering I had to sit down in the shower because my legs quitted their job and I had to rest a bit. It was one of the best orgasms I ever had.
I hoped Jack did not hear me and I listened. “No sound. That’s good.” I though. After I recovered from that shower session I formed a really dirty idea. I dried my still wet body and went to his bedroom to get dressed. I had no cloths to change and I wanted to put on not the same as last night.
I again opened the wardrobes and took out some really sexy almost slutty outfit. A black red pleated mini skirt, black stockings combined with red fishnet stockings, a black tank top combined with a black PVC-corsage and after some more searching I found some beautiful black knee-high plateau-boots.
I put on some make-up, sent the girly-Jack photos to my e-mail account and went with the photos in my hands into the living room. As I entered Jack was lying on the couch watching TV. I sneaked behind the couch.
“Good morning Jack! Have you slept well?” He turned towards me with a shocked face “Morning La…” then he realized my new outfit and his face went to totally shocked. “…ra.” Was all he could say. “You have really nice outfits in your wardrobe… and they fit me perfectly… didn`t know that we have the same size…”.
Jack tried to deny that. “These are not mine. My ex-girlfriend left them when she broke up with me…” – “Really, but why I found some photos on which you wear these outfits?” I gave him the photos and waited.
His face went from shocked to red to shocked and red and after some seconds all he could say was “Ohhh…”
“Come on Jack, you are a very sexy woman but with some advancements. For example your make-up, it could be done much better. Or these stupid wigs… everyone can see that it is a wig. Let your hair grow longer, than you don’t need a wig anymore.”
He sat there ashamed, speechless and almost crying.
“Oh Jack. Do you like to wear such outfits? Do you really like it?”
“…Yes…”
“What Jack, I could not hear you!”
“Yes, I like it.” It was barely audible but it was loud enough to hear.
“That’s perfect Jack… from now on you will dress as a woman whenever I am around. But “Jack” is not a fitting name for such a beautiful and sexy woman. From now on I will call you Melissa. Do you understand that Melissa?”
“But I don’t want that… I want to wear my outfits when I am alone. And I don’t want to be called Melissa!”
“But Melissa think about what could happen… I copied all your photos and send them via e-mail to my account. If you don’t obey me, these photos could easily be sent to your friends, to your work and, of course, to your family. Think about that…” was all I said.
He, or should I now say she, went once again from red to white back to red and again to white.
“Ok, I will become Melissa if you promise that these pictures will never be sent to anyone. Promise it!”
“Melissa… that sounds perfect. I promise that these pictures will never be sent to anyone except you don’t obey me. Now stand up and get dressed, I have put out a nice outfit. It`s lying on your bed. Now go!”
Jack went to the bedroom and after a while Melissa came back wearing all I put out for her. She wore a nice light blue medium long skirt with a white top, a push-up bra with silicone breast prostheses in it, a black cardigan, body-former shorts to hide his dick, a string, white pantyhose and black high heels. A blonde long wig and some plastic-trinkets completed her outfit.
“You look so beautiful but one thing is missing. I will do your make-up. Come over here and sit down.” She sat down and after a while her make-up was done.
“Ok Melissa wait here I will fetch some things.” I went to the bedroom and after some minutes I came back with I big bag.
“Come on, let`s go.” Melissa looked at me shocked. “What the fuck? Are you kidding? I don`t leave the house in this outfit! NEVER!”
“Oh come on Melissa, do I have to explain everything again? If you don`t obey me I will send your pictures to everyone. And, by the way, we are not walking around… we will drive to my apartment. You don`t have to worry.”
“Promise it Lara.” – “OK, I promise that we directly drive to my apartment. Is that ok for you, you chicken-hearted hot chick?”
Melissa agreed and we left her apartment, went to her car and we drove off.
During the whole time Melissa tried to hide behind her hands or her now not anymore fitting male sunglasses.
We arrived at my apartment and my vicious plan could now take the next step.
I placed Melissa on my couch and went into my bedroom only to take out some of her sluttiest outfits I took from her wardrobe.
I put out a really short and tight white skirt, a matching white tight tank top, a black push-up, a body-forming slip, a black string, white stockings and black fishnet stockings.
From my sex-toy-collection I added a chastity rod made of plastic, black leather-boots with high heels, a leather collar and a small sized butt-plug.
After putting it all onto my bed I went back to Melissa.
“Go to my bedroom and change your outfit, I have put you something sweet there. And, that’s important, wear everything. Do you understand that Melissa? I will check that!”
“Ok Lara.” was her answer. She went to my bedroom and after I don’t know how long it lasts, she came back into the living room walking like a cowboy.
“Melissa, what is your problem? Why do you walk so un-woman-like?”
“These things… it hurts in my ass… and my cock hurts as well. He can`t get hard anymore.”
“Bear it and close your legs. From now on you will wear these things every day and every night Melissa. It will make you more woman-like. By the way, come here.”
Melissa came to me, I lifted the skirt, slipped down her string and slip and locked the chastity rod with a small padlock. I did the same with her boots and her collar and after that I examined her with a devilish smile.
As she realized I locked all these things she went crazy and begged me to let her go but after some explanations about e-mailing photos she calmed down and accepted it.
If she would have known my plan, she would have left my apartment at that point in this slutty outfit. But she could not figure it out; lucky me.
She had to shave her whole body and during the next hours I taught her walking in high-heels, doing make-up, speaking as a woman, postures of women, behavior as a woman and so on. In all these education lessons I was cruel to her. I slapped, I condemned, I insulted and broke her.
In the afternoon of that glory day my pet Melissa was perfect. After all what she gave to me it was time to give her something back. So I went to my bedroom and changed my clothes.
I put Melissa`s clothes I was wearing into one of my wardrobes and took out something more fitting for this occasion; my black latex-body with red appliqués, black latex tights and black latex opera-gloves. This outfit was completed by black PVC 8” plateau sandals and a black latex collar.
I actually changed my make-up towards something appearing more dominant.
From my toy-collection I took some different sized dildos and butt-plugs and, of course, a nice big strap-on. All these toys I placed on my night table and put a silky scarf over it. Then I called for Melissa to come in here.
When she entered my bedroom she looked a bit shocked but then admiration took place in her sweet face. I ordered her to take off her string and slip and to lay down leg-spread on her belly showing me her little spread asshole.
“Now Melissa you will learn how it feels to be fucked into the ass. I have already widened your ass-pussy so it should not be too painful. It will be painful but you have to stand that.”
Without any further warning I rammed an 8” long and 2.5” thick dildo completely into her gapping ass.
She screamed as loud as she could but that was ok. I love that crying and screaming because I knew it would give her the rest. Big tears ran down her face and made a mass out of her make-up while I was pumping that dildo in and out of her beautiful wide open ass. She did not struggle or said any word to stop, she laid there crying and bearing the pain.
Quicker and deeper my strokes got and after some minutes she stopped crying. After some more minutes she started to moan quietly and I knew she enjoyed it. I fucked her with some more strikes but quitted it quickly after her first moans. As I drew the dildo out of her ass and not putting it in again she started to beg me for more.
“Please Miss Lara, fuck me. Please!” But I denied it and put a now fitting bigger anal-plug into her stretched ass.
“Now it is your turn to work and if you do it good, I will fuck your ass-pussy later.You better do a good job missy. Understand?” – “Yes Miss Lara, yes of course.” was all she answered while I belted my strap-on. It was a small purple one, only 6” long and 1.5” in diameter and as Melissa saw it she looked at me in a hopeful way.
“Melissa, I won`t fuck your ass, I will fuck your face. Or better I will let you fuck your face with my cock. Now, SUCK IT!”.
Melissa looked shocked at that, for her, big rubber cock and shook her head.
“Please Miss Lara. Don`t let me do that. It`s way too big.” – “STOP FUCKING AROUND, MELISSA! Suck it or I will let you suck it. And this would be much worse. Or do you already know how to deepthroat? I hope so! NOW, SUCK IT!”
With that I gave her a hard slap into her face. She looked at me as if she would start to cry instantly but started to lick on the rubber-cock`s head. “Good girl” I patted her head.
“But now take it into your little suck-hole and SUCK IT!” I moved my hip towards her and entered her mouth. Melissa recognized her misbehavior, my resulting anger and finally started to suck her first cock.
At first in a very nervous and cowardly way but after a bit of practice, some slaps and 3 rams with the Strap-on she showed me what a fucking wonderful cock-sucker she was.
“You don`t do that the first time, right? How many cocks have you sucked? Answer me, bitch!”
Melissa wanted to let the cock slip out of her mouth but because I awaited it I once again slapped her.
“With the fucking cock fucking your fucking face, little sissy-bitch!”
“I … never… su…cked…a…ny…co…ck…”
“Then you practiced with some dildos, didn’t you, whore?”
“N…o…Miss…La…ra…”
“OK my little cunt, then you are a real natural, you little cock-sucking bitch. Good for you, sweetheart. Now take it deeper. I wanna see you choke. NOW!” I again rammed my cock into her mouth but this time to the end.
Melissa`s eyes nearly popped out of her head and tears built up but she handled it.
With both hands I held her head firm and close to my body and waited. After only a few seconds she started to choke but I still held her. The tears began to ran down her face and she again got red so I decided to let her breath.
“Good little whore. You made it. Now you know, how to deepthroat. From now on every time someone is facefucking you or you give a blowjob you will at least deepthroat twice. Did your little bitch-brain got that?”
Still struggling for air Melissa looked at me saying “Yes… Miss… Lara…”
“Good little sissy. You are learning really quickly, that’s good for you.” I rammed the dildo again and again into her throat but every time she handled it better and soon she stopped crying.
After some more minutes penetrating her fuckface I stopped and slipped the dick out of her mouth.
“You are such a good girl now it`s time become a real girl.”

With that I went to the night table, grabbed a dildo for the strap-on and changed it.
I now had a 12” long and 3.1” thick dildo in my harness and I remembered that all my former girlfriends at first were shocked but after I penetrated them all were satisfied. Melissa saw that monster-dick hanging between my legs and gasped.
“Don’t worry sweety, you will not suck or deepthroat it…” Melissa gasped another time but of relief. “… you will be fucked into your ass! Get on the bed like a dog, with your ass-pussy towards me. And get that little anal-plug out of your ass. NOW!”
Melissa had a fearful look in her eyes but did as I said. Fortunately the bigger butt-plug stretched her ass more than the first one.
Her nice shaved and gapping asshole was right in front of that monster-dick`s head and again, without warning, I entered her rear but more gently than the first time.
As the head entered her ass, she bit the pillow and again tears started to ran but she had to bear it as a first-time ass-fucked woman.
After her ass stretched enough I began to fuck her asshole slowly. With every stroke I shove more and more of that cock into her and after some minutes I got it in completely.
“You are a pretty nice and loose ass-slut, Melissa. I hope you enjoy it because from now on you will be fucked really often. That’s the purpose for all little sluts like you.”
I pulled out the whole dick and jammed it with all my power completely into her ass. She screamed but that did not concern me. Over and over again I rammed that fucking cock into her ass-pussy until her screaming disappeared.
Instead of screaming she suddenly started to moan. It got louder and louder again and I was sure the angle I was penetrating her ass-pussy was perfect.
With every stroke I massaged her prostate and she started to love that new feeling. I speeded up my fucking and as quicker I got as louder she got.
All of a sudden she started shivering and her legs began to shake as she shouted out “Ohhh… my…. Gosh!!! OHHHH……. my……. Gosh! OHHHHHHHHH………….my…………….. AHHHHHHHHHHH!”
With that she came as hard as I ever seen! Such a beautiful anal-orgasm I had never seen before. Her whole body began to spasm and then there was silence. All her muscles relaxed and she sank into the bed.
I smiled happy but also a bit devilish, pulled the dildo out of her ass and put in a now perfectly fitting big butt-plug. As it went in I heard a soft moan from Melissa, I put her slip and string back on and covered her with the blanked.
After this exhausting day she had the privilege to sleep.
Out of my wardrobe I took some normal clothes went into the living room and got dressed in a normal way with jeans, tank top and high heels. Then I left the apartment to drive to my favorite clothes-, sex-toy- and fetish-shops to get more funny things to use with and especially in and on Melissa.

—The end(?)—

If you liked that little story mail me and I will write the 2. day