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True story of an old man in the woods
I was just a young lad the first time i did any thing with another guy, i was still living with mom in the house she inherited from her father after he died in a small village that mainly had elderly people living in it.
There certainly wasn t any one my age about so contact with other youth s was limited to school.
Most of my time was spent playing alone or helping mom about the house, then some thing happened that was to change me for ever.
It was a Sunday morning and mom was home doing some house work, i was watching cartoons on the TV when she called to me to help her get the washing in as it had started to rain.
I put my shoes on and went to help, i worked my way down the line till i came to some of her tights and hesitated till she told me to hurry up.
I grabbed them off the line but the moment i touched them i became fixated at how the material felt on my skin, they felt so silky and smooth and i just wanted to hold but new mom would wonder what i was doing so i moved to the next item on the line a pair of silk full back panties.
Again i was amazed at how they felt to the touch and new i wanted to play with them more.
After that every chance i got i would go in the bathroom and search the laundry basket for a pair of tights or panties just so i could touch them.
I didn t put them on at that time just touched them, it hadn t even occurred to me to wear them i just loved how they felt in my hands.
This went on for a few months till one evening i saw a program on telly about men who like to dress as girls.
It was like a revelation to me and i new i had to try it with some of moms tights, not wanting to be caught i waited till the next time i new she was out for a while so i would be safe.
The moment i felt the silky smooth material on my skin i knew this was something i wanted to do over and over.
Of course because of my age at the time it wasn t a sexual thing it was just something that felt natural to me but i knew others would be upset if i was ever caught.
I had been wearing the tights just in the bathroom for a few weeks when mom nearly caught me and over the next month she almost caught me 4 more times.
As the risk seemed to be getting higher i decided that may be i should stop doing it around the house and look for some other place to indulge my hobby.
As we lived in a rural out in the sticks village at the time it wasn t hard to find an out of sight place to continue my dressing.
For just over 3 years i continued to do my dressing in the woods behind our village when ever the weather let me, i had found a perfect place hidden from the roads and out of sight of any houses.
The woods were in the middle of a big farm field and no one ever really went in them, in the center of the woods was a clearing with a large amount of tallish under growth closing it in and a large fallen tree trunk making it perfect for my needs.
By the time i was 12 i had started buying my own things when pocket money allowed and had grown from just wearing tights to putting on panties bras stockings and suspenders and even skirts from time to time and when the chance arose some of moms shoes.
Being the only k** in the village and with very little to do there at weekends and school holidays it led to a lot of free time on my hands that i used to further my dressing.
So dressing is what i did more and more, i would head to the woods recover the clothes i had hidden in bags there and play dress up.
Most of the clothes were things mom had thrown out and a few things i had sneaked off washing lines during lunch breaks at school when i would sneak on to the housing estate to see what i could find.
In the woods i would pick what i wanted to wear then put it on and just walk around loving how the garments felt on my skin, some how it made me feel more relaxed more comfortable it still wasn t sexual at that age but it was becoming a very big part of my life.
When i was 12 an older gent had moved in to the house 2 doors down from us, he was easily in his mid 50 s and lived alone.
From the start he used to make me feel uneasy as every time i went out he seemed to be in one of his windows and would watch me till i was out of sight.
At first i just thought he was some old guy poking his nose in because he was lonely being by himself all the time.
One Saturday as i was off out to the woods i saw the old guy watching me from his window as usual, i don t know why but as i looked up at him i smiled but it was what he did next that caught me off guard as i smiled at him he winked back at me then disappeared from the window.
I somehow felt a little uneasy at what had just happened so rather than head straight for the woods i walked round the village for about 20 minutes.
When the feeling had gone i walked back up the main road to head towards the woods but as i rounded the bend in the road i saw the old guy walking in my direction.
I started to feel uneasy again but kept walking, as the old guy passed me he smiled and winked at me again i just smiled a faint smile in return and carried on.
When i got to the gate of the field that i had to cross to get to the woods i stopped, i rested at the gate something telling me to hold there for a while and look back to see if the old guy had followed me.
I waited for about 5 minutes but didn t see any sign of him, i thought about going back home but as i was at the gate and it was a nice day i really wanted to go play dress up so i decided to carry on to the woods.
As i reached the edge of the woods i climbed over the fence surrounding it and moved in to cover of the first line of trees.
I held there for a little while looking to see if the old man was following but i couldn t see any one.
Feeling safe i headed for the area of the woods were i hid my things and sure that i was now alone and had not been followed i started to pick what i was going to wear.
I settled on a tight black sports type bra that almost made me look as if i had small boobs and cleavage i matched them with some black full back nylon panties and to finish off a pair of black tights and some 4 inch heels mom had thrown out some weeks before.
I could feel a light breeze on my skin that and the warmth of the sun with what i was wearing made me feel great and so i started to walk around.
Normally when i m like that i m lost to all around me, caught up in my own world and loving how wearing women s things made me feel.
I used to spend hours just prancing around the woods in what i had chosen to wear wishing that i could dress like it all the time, sometimes i would think about wearing panties and tights under my jeans when in the village or at home but was to scared.
On this day as the sun shone down and the light breeze brushed my skin as i was walking around in nothing but bra, panties, tights and heels i for the first time also felt a little sexy.
I started back to were i had gotten dressed thinking it was time to try some thing else on but as i got to the small clearing were my things were i stopped dead in my tracks.
Were my male clothes and dress up things should have been there was now nothing.
Panic took over me and i started to run around looking for my things but sure i had left them in the clearing.
I was lost, what was i going to do i mean there was no way i could walk back home dressed as i was and i couldn t stay here for ever either.
I went back to the clearing again to think what to do but as i got there in front of me was the old guy from 2 doors down.
He was sitting on the fallen tree trunk and on the floor at his feet was the bags with my dress up things in them.
At first i didn t know what to say or do i was just frozen to the spot unable to move or do anything.
I stood for what seemed like ages but was probably only a few seconds before i fully understood what was happening, i was standing in front of the old guy who lived near me dressed in panties, bra, tights and heels and nothing else.
As my senses returned and i could see him looking at me with a big smile on his face i jumped behind some of the high under growth that surrounded the clearing.
After a few seconds he called out that it was no good hiding as he had seen me and what i had on.
I shouted for my clothes but he told me they was safe for now and not to worry about them just yet, when i asked what did he mean he just laughed and said it depended on me as to what happened to them and when i got them back.
I was getting worried now, there i was dressed in nothing but women s undergarments with an old guy looking at me telling me i was supposed to do some thing to get my male clothes back.
He called again telling me to come out from behind the bushes but i said no, it wasn t till he said that if i didn t do as he told me he would collect up my things and leave that i really started to understand what was happening.
He told me to come out again and that he would count to 5 then leave.
I had no choice so slowly and trying to cover my self as best i could with my arms i stepped out from the bush straight into his gaze.
He told me to move closer to him so i took a few steps forward, he was looking me up and down that grin still on his face.
I was just a few feet from him when he stood up and walked behind me, i went to turn to see him but he told me to keep facing the way i was.
I looked straight ahead wondering what was going to happen next when i first felt something slap the cheek of my ass and then what i new must have been his hands grope both my ass cheeks.
My worst fear was coming true but at the same time i felt a tingle in my body as he squeezed my cheeks a few times.
I turned to face him trying to look angry at what he had done but before i could utter a word he laughed out loud and said don t act so shocked you little bitch, you cant go round dressed like that and then be surprised when an man catches you and starts to feel you up some.
With that he turned me to face away from him and once again i felt his hands on my ass squeezing and rubbing my cheeks hard.
In my head i was screaming to run away but my legs wouldn t respond and as his hands continued to play with my ass i new i was starting to like how it felt.
By this time all i could do was stand there as the old guy continued to feel up my ass through my tights squeezing my cheeks and the odd slap on them.
I became aware of the sounds of heavy breathing and it didn t take long to work it out it was me but as i tried to slow my breaths down i herd the old guy breathing heavy to.
I new i was starting to like how his hands felt on me but i also new that really i should be trying to run away, yet all i did was stand there and let him touch me as he pleased.
The strange thoughts went round my head until i was pulled back to reality by the old guy now wrapping his arms round me and pulling me close to him.
His hands were now on my chest his fingers searching out my nipples through the bra i was wearing, he trapped each one between finger and thumb and began to pinch them softly at first but getting harder all the time.
It hurt a little as he pinched them but at the same time i could feel my self starting to enjoy what was happening more and more.
I wasn t what you would call tall at that age but the old guy was only a few inches taller than me and so the perfect height to lean in and kiss my neck as his fingers continued to work my nipples.
This went on for what seemed like an age but was more like 2 or 3 minutes all the time my mind and will had turned to jelly and all i could do was let him carry on making me feel more and more sexual about the hole experience.
He moved his right hand from my chest and i felt it near my bum, he was doing something but it wasn t till i herd the noise of a zip being undone that new what he was doing.
With his left hand still playing with my nipples his right hand now grasped me round the waste holding me tight against him and i felt something pressing against my bum cheeks.
I had not gone to the woods that day intending to do any thing other than my usual dressing up and had never even thought about doing any with sexual with a man before and even tho i had let things get this far the feel of his cock now pressing against my bum (even if i was in tights and panties) was starting to go further than i wanted it to.
I tried to pull away but his hold on me was to strong and he easily pulled me back against him, he put his lips to my ear and said we are not done yet baby we only just getting started.
The enjoyment i had started to feel up to that point now left me a little and worry was taking its place.
I could feel his cock starting to rub hard against my bum his breathing getting hard and fast with each movement, his hand round my waste now moved back to my ass squeezing my cheeks hard.
I tried to pull away a couple more times but he was to strong and in the end i gave in hoping that it wouldn t go any further.
He asked me if i had done any thing with a man before and when i told him that this was my first time he told me he was going to enjoy breaking in my virgin ass, as he said this i was filled with a mix of fear and excitement in equal measure.
I could not deny that i was enjoying the feeling of him pinching my nipples and playing with my bum and even the feel of his cock rubbing on my ass cheeks through my panties and tights was starting to feel pretty good to.
Until this day any thoughts i had about sex was always about females yet here i was my first sexual encounter and not a girl in sight just me dressed as a girl and a horny old man who was now looking to use me like a girl.
My head was swimming with thoughts of what might happen when i became aware that i had relaxed so much my head had tilted back and was now laying on the old mans shoulder, my body had gone limp and i had surrendered my self to his touch.
My thoughts were interrupted by the old guy saying my moans were proof that i wanted this to happen, until that point i had not been aware of the mild moaning noises i was making.
He must have seen this as sign that i was willing as he turned me in his arms to face him and as i stood looking into his face his put one hand on my shoulder and started to push downwards.
To this day i don t know why but i allowed him to push me to my knees and as i found my self eye level with his cock i new what he wanted me to do, i know now that he wasn t what you would call big but at that age his 5 inch cock looked big enough.
He was fully hard and his foreskin had pulled back to uncover a deep purple mushroom shaped cock head, for a few seconds i just stared at it being the first one out side of my own i had even seen but already i was entranced by how it looked.
He didn t even have to say a word as my own curious nature took over and i reached out my hand to take hold of it.
As my fingers closed round the shaft i was hit by how soft the skin felt the warmth of it, i was lost in the moment not even aware of the guy him self it was just me and his cock and the longer i held it a growing urge to take it in my mouth.
As i held his cock in my hand i noticed the slit in the end had leaked some pre cum and again with out being prompted my curious nature took over and i lent in and with the tip of my tongue licked it from his head.
As i licked the pre cum he let out a long loud moan and i found my self kind of proud that it was me who had made him do it, i opened my mouth my head forward and took his cock in my mouth and as i closed my lips around it i new that i was really enjoying what was happening and didn t care any longer what would happen next.
I doubt very much i was doing a great job at giving my first blow job but for me i was loving having his cock in my mouth, sucking it every now and then getting a taste of his pre cum.
He placed his hands either side of my head and held it as i worked his cock in and out of my mouth, my actions being spurred on by his comments about me being a good gurl sucking his cock.
Them more he showed his pleasure the more i tried to please him as i used my lips tongue and fingers on his cock and all the time i was getting more excited at what was happening.
I loved how his cock felt in my mouth its taste and texture the way his hands held my head as he now started to pump my mouth, even the way he spoke to me as i sucked calling me a gurl and how my mouth felt good on him and how he always wanted to find a slut like me.
I worked his cock in my mouth for ages all the time wishing it would never end, surprising my self at how much i enjoyed it despite never having thought about men before let alone letting one do such things to me.
I herd his voice as he asked if i wanted him to stop or carry on and cum in my mouth, i wasn t sure if i wanted him to do that but i new i didn t want him to take his cock out as it felt so good so i held his hips and pulled him into my mouth in time with his pumping motion.
I guess that was the answer he was looking for as i felt his hold on my head tighten and his pace quicken before feeling his cock twitch several times and then start to flood my mouth with a warm salty sticky fluid.
He was still pumping my mouth as he cum so i had no choice but to swollow his load but even this turned to pleasure when i herd him telling me what a hot little fucker i was for eating his cum.
All caution was gone now i was left with just the urge to please him to know that what i was doing was making him happy, i know that sounds weird but its how i felt at the time.
I new i wanted to do this over and over and figured that if i did what he wanted then he would want to do it more as well, when he pulled his cock from my mouth i suddenly felt sad that it was finished and with out thinking i mumbled that i wanted to do it again.
He told me i would do every chance he got and that just cause he d cum once didn t mean today was over either, with that he lifted me to my feet and gave me a long hard kiss on the lips his one hand starting to work my nipples again.
I was loving every moment of it now all doubt and worry gone, just caught up in the new and highly erotic feelings that covered me head to toe.
He moved his free hand down to my ass and once again i felt it start to squeeze my cheeks rubbing the material of my panties and tights against my skin i was shaking a little with the pleasure of it.
I then felt him start to work his hand in side my panties so he was now touching bare skin his kisses getting harder and more intense his breath coming faster, my arms were d****d round his neck holding him as we continued to kiss his tongue now searching my mouth as his hands did the same to my bum.
Slowly he started to lower my panties and tights and once they were clear of my ass he moved his face away from mine took his middle finger of his right hand and put it to my mouth telling me to suck it and get it all wet.
This i did and when it was wet enough he pulled it from my mouth and moved it to my tight little hole, he gently at first pushed the tip of his finger into me telling me that i really was tight and how that excited him.
He moved the tip of his finger in and out of me getting me ready for what was to come, i wasn t sure if i would like it but to my surprise the motion of his finger in my ass just added to feelings growing in me and i wanted to feel what it would be like with his cock doing it instead.
After a few minutes of his finger working me all the time still kissing me he pulled it out and much to my excitement he then sucked it giving a low mmmmm noise as he did.
He took my hand and led me to the fallen tree trunk turned me to face it and told me to lean over keeping my bum in the air, i was expecting to feel his hands on my ass getting me ready for his cock but when i felt his breath on my hole followed by his tongues an electric bolt of pure ecstasy shot down my spine and my hole body began to shake with pleasure.
I could feel him pulling my cheeks apart and trying to push his tongue into my hole and as he did the intensity of what i was feeling exploded and despite him not having touched my cock it twitched a little and then shot one of the biggest loads i had ever done over the fallen tree.
My hole body was now shaking so hard i couldn t have stopped it if i tried,i was aware of him talking telling me that from this day on despite being a boy i was going to be his special gurl and that when ever we were together that s how he would treat me and refer to me and my body.
My hole was so wet at this point that i could feel his saliva starting to run down my leg he then worked his finger into my hole a few more times getting it ready for what he called a good fucking be fore standing up and placing his cock head against my pussy (his words).
With one hard forward motion his cock not only managed to open my hole to him but also sunk its self balls deep in me, even though he wasn t that big and he had lubed me really well the initial pain of him entering me was blistering and i almost screamed out loud.
His cock now deep in my pussy he halted while he moved his hands back to my nipples and began to pinch them he leaned over me laying his body on my back and started to kiss and nibble on my ear, all the time my ass was really sore but starting to accept the hard cock that was now lodged deep inside it.
Slowly he started pulling his cock out till only the head was left in and then gently pushing it all the way in me again, this lasted a few minutes and i was grateful as it allowed me to time to get used to him fucking me and my sore ass to recover some.
I began to feel him speed up his motion with each forward thrust of his cock, his fingers pinching my nipples harder and harder and his breath was really loud and heavy in my ear as he nibbled my lobe.
My own excitement was also growing and i new i was enjoying this even more than i did having his cock in my mouth, i had seen the odd porn movie before and remembered that in most the women always asked the guy to fuck them harder and being so out of control at what this guy was doing to me i found my self saying the same words over and over.
He obliged and i felt his pace quicken and also the power he put into each push forward and i could hear the slapping sound as his skin touched mine every time he rammed his cock back into me, i could feel my cock was rock hard and i felt my own orgasm brewing inside me.
Once again i shot my load not as much as the first one but enough for me to know i wanted to do this for ever more.
By this time the old guy was fucking me so hard and fast that i thought he was going to pass straight through me, he was shouting in my ear how tight my cunt was and horny i was making him.
He managed to slam into me for just a few more minutes before he to shot several hot loads of cum deep in my ass and i could feel them all, just before he slumped on top of me and as the last really hard thrust slammed hard into my pussy he whispered in my ear i fucking love you bitch .
We stayed in that position for what seemed like ages, in one of my dressing up bags was an old blanket that i sometimes just lay on while dressed up in the sun and the old guy got it out spread it on the floor and we both lay on it.
For the next hour we kissed cuddled and caressed each other every now and then he would tell me something dirty about the sex we just had like how hot my pussy was or how i was such horny slut letting him cum in my mouth.
At the end of the hour we both horny and he kept his promise and let me suck his cock again and i swollowed yet another one of his loads.
By the time i got home all i could do was shower and then lay on my bed thinking of how unexpected and unplanned the day had been, i thought over how easy it had been for him to get me to do the things he wanted and yet how much i had enjoyed it and that i couldn t wait for it to happen again.
Before we parted ways the old guy told me that he would be home all day tomorrow and he new my mom would be at work for and gone from the house for over 10 hours, i was going to be his special little girl for every minute of it.
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