The 1st Time
The very first time
Now at 18 years of age I have been dressing in secret using family members clothing when ever possible since I was around ************.
My parents are out for the evening at a local event and my brain is already swimming with ideas on which of her sexy lingerie I can wear this evening while they are out. My mother suddenly shatters my dreams when she tells me that I have been volunteered to baby sit for their friends **********. Don't worry she says they will sleep right through the night and his parents will be home by 3am.
Great there go my hopes and fantasys for this evening.
Time comes and I pop round to their house and knock on the door, I have met them a few times but don't really know them.
Julia answers the door in a sexy blue cocktail dress and heels and I can feel myself blush at the thoughts running through my head of me wearing it, her wearing it with me etc etc
I am invited in and find her husband Steve playing on his Playstaion 1 on the sofa.
Steve is what I would call an average guy not handsome but also not ugly if you know what I mean, tonight hes in shirt, trousers and tie but does not look glad to see me.
I soon gather by his choice of words and comments he would rather stay in instead of going to the event but Julia has insisted he go out.
I am instructed that their daughter is already in bed fast asleep and never wakes up and that they will be home at 3am on a private bus.
Steve as hes going out the door tells me that I can play his PS1 if I want to keep myself entertained and that there are more games in the draw under the TV.
So my planned night of excitement gone I sit down and start playing Grand Turismo after an hour or so im bored and go to find what other games are in the draw.
Opening the draw under the TV I find a few other games and some VHS tapes, out of boredom and curiosity I flick through the titles until I settle on one without a label.
You always dream about this kind of stuff but I thought no it cant be if they had some porn surely it would be somewhere else, but with excitement starting to build again I place the tape into the Machine and push the play button.
My mouth falls open as the scene on the screen in front of me, is of a bed made with black satin sheets and on it in a sexy black and red basque with black stockings and black high heels lays Julia.
Im not sure which reacts first my brain or my cock as its instantly hard and pleading for me to touch it.
I sit back down on the sofa and start to watch as she takes a pink realistic dildo and starts slowly fucking herself with it with one hand while the other works her clit.
I can hear he moaning and its making me harder than I thought possible when suddenly I hear a male voice and Steve appears on the screen naked and hard.
Julia removes the dildo and Steve slides deep inside with a satisfying groan and I am in exstacy.
Sitting there watching the 2 people who were in this very room not long ago fucking on their TV was driving me crazy and I was about to reach for my rock hard cock when a naughty thought popped into my head.
"Hmmmm if shes wearing that in this video that means her basque and stockings are in this house somewhere" and like that Im off practically running up the stairs to get to her bedroom.
5 draws later and I have hit the mother load im so excited as I leaf through all her sexy gear and there is sooooo much of it.
I finally find the same outfit from the TV and now is my time to have fun.
I remove my boy clothes and pile them in the corner, I first pull on the basque which is crotchless, then the stockings which I snap the plastic clips onto too hold them up, by now im adept at doing this but on TV I had seen most women wear them one in front one on the side, where as I had always found it more sexy to have one on the front and one straight down the back nice and tight so I can feel it on my ass.
Dressed I look in the mirror on the wardrobe and admirer how I look, not good enough is the thought then I remember her heels so I start the hunt all over again. Within 2 minutes I have found the shoes and an additional surprise I hadn't considered.
Luckily the shoes are a size 6 and I am only a 7 so they fit but its hard to stand in them properly.
The additional surprise is the same dildo Julia was using on her self in the video, in the same draw I had found lube and condoms.
Now is the time as I really cant hold myself back any longer so I carry the heels, dildo and lube down stairs.
Put the heels on and get comfy on the sofa heel tips digging into the edge so my legs are apart and up in the air.
I push play on the video from the start as I want this to last and I place some lube on my index finger and start to rub my tight ass.
Slowly I slip my finger in and then im rubbing like crazy to match Julias hand movements on the screen.
When Steve appears on the screen I hit paused and apply way to much lube to the dildo but it is a little scary.
As I unpause the video and Steve enters her I slowly push the pink Dildo into my ass thinking its him doing it and then as he thrusts I thrust.
I continue this for 10 minutes while refusing to touch my begging cock, until Steve unloads into Julia and then the video stops. I rewind it and start to watch again but its just not the same.
Again another naughty idea pops into my head, so I pause the video and remove the heels, but keep the dildo in pinching my cheeks together to hold it in place and then head upstairs.
Standing in the bedroom door looking at the same bed with the same sheets I had just watched made me smile. I put the heels back on and lay on the bed just where Julia was, at this point I realise that all along in the video she wasn't looking at Steve she was watching her self in the wardrobe mirror. Super pleased I start to fuck my ass with her dildo just like she had.
5 minutes pass and im starting to think about getting my cock out and finishing myself when Steve bursts into the room.
"What the fuck are you doi…… he stops dead mid sentence and just stands there looking at me.
Scared shitless im going to get either beaten up or shamed to the world I start to cry and beg that he doesn't tell anyone.
"Shut up" he says
"Tell me exactly what the fuck you are doing"
Well I found the video downstairs while looking for something to watch and started to watch it, then things kind of got out of my control.
I wanted to see if Julia still had the same outfit, then I thought I might just put it on to try it out, then I found the same toy and and and then this happened, im sooo sorry please don't tell anyone.
He stands there looking at me and looking at the scene and I see a small grin appear on his lips, I don't know weather to be scared or what as its a weird face too pull at this situation but at least hes not shouting anymore.
"So you found our little video then thought you would dress as Julia on the same bed in the same position?"
Yes I honestly don't know why but I just did it, I couldn't stop myself.
"So if you want to recreate what you saw in the video then lets recreate it"
Im confused what does he mean whats he getting at and then I see him start to undress.
The fear that is coursing through me is also accompanied by massive amounts of joy that this could be it this could be the moment when someone finally makes a "Girl" out of me.
Now naked and with a decent size hard on standing in front of my im paralyzed with fear.
"Don't talk okay, just do what Julia did on the video and when Im ready I will walk over to you just like you watched downstairs"
Oka...
"DONT TALK"
I just nod back and slowly start to push the dildo in and out of my tight ass
"Julia was rubbing her clit if I remember correctly, I don't see you doing that"
Nervously I pull my once again hard cock from the side of the basque and start to rub the tip with my other hand.
Steve is now standing there rubbing his hard cock and seemingly enjoying the show before him.
1-2 mins of this feels like forever when he finally stops walks to the cabinet at the side of the bed and removes a condom from it.
Tearing the packet I lay there still pleasuring myself watching with both fear and joy at what he is doing, I have never had a real cock before and im nervous but also sooo excited to finally become the "Girl" I really want to be.
Steve slowly walks over just like in the video and takes the lube from my side and applys generous amounts to his cock, he then pulls the dildo from my ass and drops it on the floor.
He moves his hand down and I for the first time ever feel someone else touch my ass, his fingers start to explorer my hole and also apply fresh lube to the area which I am more than grateful for.
1 finger soon becomes 2 and hes getting deeper and faster with his thrusts, all of a sudden he judges im ready and pulls them out, NOW is my time please please please let this happen.
He moves the tip of his cock to the edge of my hole and slowly rubs it around which drives me crazy, im trying to push myself down the bed desperate to get it inside me to feel what I have always dreamed of.
He leans forward and moves both of my arms upward above my head, then positions himself in a crouch at the end of the bed and slowly ever so slowly and delicately slides his hard pulsing cock into my ass.
My cock almost explodes the moment he is in and again when he reaches the very top, I had never pushed a dildo that far in and it feels amazing.
He starts to thrust and I start to moan, slow at first but gradually getting faster and harder just like his fingers did earlier.
3 mins which feel more like 50 mins of amazement pass and with one huge hard deep thrust I feel his cock go crazy inside me and I know he is cumming.
Ohh my god I cant believe this im such a slut and its what I have always dreamt of being, a few more thrusts and he is spent, laying on top of me he holds my face and kisses me deeply our tongues rolling around each other.
After the kiss finishes I reach for my cock with the plan of draining myself as fast as I can.
"NO, no don't do that I want you too wait. Julia has loads of clothes and will never miss these ones so I want you to take them home and I want you to wank yourself silly in them as much as you can"
"You cant take her heels but if your a good girl and come and visit me next time she is away or the next time I can sneak away from a get together I promise I will buy you some of your own"
And that is how it went for many months me popping round and servicing him in payment for him buying me my very own first wardrobe, heels, stockings, dresses, lingerie, makeup and a wig all of it.
The end of that one I hope everyone enjoys and please any tips etc feel free, as I said never written a story before never mind an erotic one but thought I should put some stuff down for others to enjoy SO ENJOY
Hopefully there will be more
LOVE and keep safe Sammy x
Now at 18 years of age I have been dressing in secret using family members clothing when ever possible since I was around ************.
My parents are out for the evening at a local event and my brain is already swimming with ideas on which of her sexy lingerie I can wear this evening while they are out. My mother suddenly shatters my dreams when she tells me that I have been volunteered to baby sit for their friends **********. Don't worry she says they will sleep right through the night and his parents will be home by 3am.
Great there go my hopes and fantasys for this evening.
Time comes and I pop round to their house and knock on the door, I have met them a few times but don't really know them.
Julia answers the door in a sexy blue cocktail dress and heels and I can feel myself blush at the thoughts running through my head of me wearing it, her wearing it with me etc etc
I am invited in and find her husband Steve playing on his Playstaion 1 on the sofa.
Steve is what I would call an average guy not handsome but also not ugly if you know what I mean, tonight hes in shirt, trousers and tie but does not look glad to see me.
I soon gather by his choice of words and comments he would rather stay in instead of going to the event but Julia has insisted he go out.
I am instructed that their daughter is already in bed fast asleep and never wakes up and that they will be home at 3am on a private bus.
Steve as hes going out the door tells me that I can play his PS1 if I want to keep myself entertained and that there are more games in the draw under the TV.
So my planned night of excitement gone I sit down and start playing Grand Turismo after an hour or so im bored and go to find what other games are in the draw.
Opening the draw under the TV I find a few other games and some VHS tapes, out of boredom and curiosity I flick through the titles until I settle on one without a label.
You always dream about this kind of stuff but I thought no it cant be if they had some porn surely it would be somewhere else, but with excitement starting to build again I place the tape into the Machine and push the play button.
My mouth falls open as the scene on the screen in front of me, is of a bed made with black satin sheets and on it in a sexy black and red basque with black stockings and black high heels lays Julia.
Im not sure which reacts first my brain or my cock as its instantly hard and pleading for me to touch it.
I sit back down on the sofa and start to watch as she takes a pink realistic dildo and starts slowly fucking herself with it with one hand while the other works her clit.
I can hear he moaning and its making me harder than I thought possible when suddenly I hear a male voice and Steve appears on the screen naked and hard.
Julia removes the dildo and Steve slides deep inside with a satisfying groan and I am in exstacy.
Sitting there watching the 2 people who were in this very room not long ago fucking on their TV was driving me crazy and I was about to reach for my rock hard cock when a naughty thought popped into my head.
"Hmmmm if shes wearing that in this video that means her basque and stockings are in this house somewhere" and like that Im off practically running up the stairs to get to her bedroom.
5 draws later and I have hit the mother load im so excited as I leaf through all her sexy gear and there is sooooo much of it.
I finally find the same outfit from the TV and now is my time to have fun.
I remove my boy clothes and pile them in the corner, I first pull on the basque which is crotchless, then the stockings which I snap the plastic clips onto too hold them up, by now im adept at doing this but on TV I had seen most women wear them one in front one on the side, where as I had always found it more sexy to have one on the front and one straight down the back nice and tight so I can feel it on my ass.
Dressed I look in the mirror on the wardrobe and admirer how I look, not good enough is the thought then I remember her heels so I start the hunt all over again. Within 2 minutes I have found the shoes and an additional surprise I hadn't considered.
Luckily the shoes are a size 6 and I am only a 7 so they fit but its hard to stand in them properly.
The additional surprise is the same dildo Julia was using on her self in the video, in the same draw I had found lube and condoms.
Now is the time as I really cant hold myself back any longer so I carry the heels, dildo and lube down stairs.
Put the heels on and get comfy on the sofa heel tips digging into the edge so my legs are apart and up in the air.
I push play on the video from the start as I want this to last and I place some lube on my index finger and start to rub my tight ass.
Slowly I slip my finger in and then im rubbing like crazy to match Julias hand movements on the screen.
When Steve appears on the screen I hit paused and apply way to much lube to the dildo but it is a little scary.
As I unpause the video and Steve enters her I slowly push the pink Dildo into my ass thinking its him doing it and then as he thrusts I thrust.
I continue this for 10 minutes while refusing to touch my begging cock, until Steve unloads into Julia and then the video stops. I rewind it and start to watch again but its just not the same.
Again another naughty idea pops into my head, so I pause the video and remove the heels, but keep the dildo in pinching my cheeks together to hold it in place and then head upstairs.
Standing in the bedroom door looking at the same bed with the same sheets I had just watched made me smile. I put the heels back on and lay on the bed just where Julia was, at this point I realise that all along in the video she wasn't looking at Steve she was watching her self in the wardrobe mirror. Super pleased I start to fuck my ass with her dildo just like she had.
5 minutes pass and im starting to think about getting my cock out and finishing myself when Steve bursts into the room.
"What the fuck are you doi…… he stops dead mid sentence and just stands there looking at me.
Scared shitless im going to get either beaten up or shamed to the world I start to cry and beg that he doesn't tell anyone.
"Shut up" he says
"Tell me exactly what the fuck you are doing"
Well I found the video downstairs while looking for something to watch and started to watch it, then things kind of got out of my control.
I wanted to see if Julia still had the same outfit, then I thought I might just put it on to try it out, then I found the same toy and and and then this happened, im sooo sorry please don't tell anyone.
He stands there looking at me and looking at the scene and I see a small grin appear on his lips, I don't know weather to be scared or what as its a weird face too pull at this situation but at least hes not shouting anymore.
"So you found our little video then thought you would dress as Julia on the same bed in the same position?"
Yes I honestly don't know why but I just did it, I couldn't stop myself.
"So if you want to recreate what you saw in the video then lets recreate it"
Im confused what does he mean whats he getting at and then I see him start to undress.
The fear that is coursing through me is also accompanied by massive amounts of joy that this could be it this could be the moment when someone finally makes a "Girl" out of me.
Now naked and with a decent size hard on standing in front of my im paralyzed with fear.
"Don't talk okay, just do what Julia did on the video and when Im ready I will walk over to you just like you watched downstairs"
Oka...
"DONT TALK"
I just nod back and slowly start to push the dildo in and out of my tight ass
"Julia was rubbing her clit if I remember correctly, I don't see you doing that"
Nervously I pull my once again hard cock from the side of the basque and start to rub the tip with my other hand.
Steve is now standing there rubbing his hard cock and seemingly enjoying the show before him.
1-2 mins of this feels like forever when he finally stops walks to the cabinet at the side of the bed and removes a condom from it.
Tearing the packet I lay there still pleasuring myself watching with both fear and joy at what he is doing, I have never had a real cock before and im nervous but also sooo excited to finally become the "Girl" I really want to be.
Steve slowly walks over just like in the video and takes the lube from my side and applys generous amounts to his cock, he then pulls the dildo from my ass and drops it on the floor.
He moves his hand down and I for the first time ever feel someone else touch my ass, his fingers start to explorer my hole and also apply fresh lube to the area which I am more than grateful for.
1 finger soon becomes 2 and hes getting deeper and faster with his thrusts, all of a sudden he judges im ready and pulls them out, NOW is my time please please please let this happen.
He moves the tip of his cock to the edge of my hole and slowly rubs it around which drives me crazy, im trying to push myself down the bed desperate to get it inside me to feel what I have always dreamed of.
He leans forward and moves both of my arms upward above my head, then positions himself in a crouch at the end of the bed and slowly ever so slowly and delicately slides his hard pulsing cock into my ass.
My cock almost explodes the moment he is in and again when he reaches the very top, I had never pushed a dildo that far in and it feels amazing.
He starts to thrust and I start to moan, slow at first but gradually getting faster and harder just like his fingers did earlier.
3 mins which feel more like 50 mins of amazement pass and with one huge hard deep thrust I feel his cock go crazy inside me and I know he is cumming.
Ohh my god I cant believe this im such a slut and its what I have always dreamt of being, a few more thrusts and he is spent, laying on top of me he holds my face and kisses me deeply our tongues rolling around each other.
After the kiss finishes I reach for my cock with the plan of draining myself as fast as I can.
"NO, no don't do that I want you too wait. Julia has loads of clothes and will never miss these ones so I want you to take them home and I want you to wank yourself silly in them as much as you can"
"You cant take her heels but if your a good girl and come and visit me next time she is away or the next time I can sneak away from a get together I promise I will buy you some of your own"
And that is how it went for many months me popping round and servicing him in payment for him buying me my very own first wardrobe, heels, stockings, dresses, lingerie, makeup and a wig all of it.
The end of that one I hope everyone enjoys and please any tips etc feel free, as I said never written a story before never mind an erotic one but thought I should put some stuff down for others to enjoy SO ENJOY
Hopefully there will be more
LOVE and keep safe Sammy x
5年前
