To the Woods !

[shiningstar]

To the Woods!

Chapter 1​

It was a warm, autumn afternoon when Brian picked me up at my flat and we drove into town. On the way Brian told me about the 24 year old guy
he 'd met..... Steve...... who was a cross dresser. He had arranged to meet Steve in the lounge of the George and Dragon at 2 pm.
" Steve will be in his female persona , " said Brian, " so we must call her .... Heather.... "
"OK " I said, "will do ."
I was a little bit surprised.... how did Brian.... a 53 year old , middle aged guy.... pull a 24 year old cross dresser ? Ok, Brian was a good looking, well hung guy.... but there was a huge, 30 year age difference !
Brian was big into cam corders back then ... in 2003.... and liked nothing more than making sex movies on video tape. That's where I came in.... I was his favourite cam corder guy !
He taught me how to use his expensive cam corder.... how to zoom in for close ups..... I was becoming quite the expert !
" Is Heather up for a bit of filming ? " I asked Brian as we drove along.
" Yeah, she's up for it , " said Brian, " I promised to buy her some gear as a sweetener .... "
" Gear ? you mean drugs ? " I asked.
"No" said Brian , smiling..... " I'm going to treat her to some sexy underwear..... I think she deserves it.... it's an expensive game being a cross dresser.... you need two sets of clothes..... I feel I v'e got to help the poor girl out ."

We arrived at the George and Dragon just before 2 pm.
" I'll have a swift half with her.... then we'll walk over to Matalan... " said Brian . I stayed in the car while Brian went into the pub to meet Heather.
Brian was in the pub for about 15 minutes, then I saw him leave with the attractive Heather. They set off walking to Matalan.... a big store not far along the main street.
I had a 30 minute wait.... sitting there in the car park of the George and Dragon ..... fantasising about an afternoon of sex. At last I saw them.... walking along together.... Heather carrying a posh Matalan carrier bag. I opened the car door and got into the back seat to allow Heather to sit up front with Brian. To my surprise she put her carrier bag on the front seat then came and sat in the back with me !
" Hi, I'm Dave.... " I said... shaking her hand.
" I'm Heather , " she said, smiling shyly. The brown eyes.... the auburn hair on her shoulders.... those breasts outlined by a thin, pink blouse .... she looked sexy and attractive....... I was so impressed !

On the short drive to the lake we chatted about this and that.
As we chatted I could see that Heather was quite nervous..... after all she was in a car with two older guys she hardly knew.... Brian age 53 me age 43.
I casually put my hand on her knee and rubbed up and down her black stockings. She did n't flinch ...... which only served to make me even bolder... I moved my hand up and under her black , pleated mini skirt. I reached her panties and felt the outline of her cock getting hard and erect.

Brian .... in the driving seat..... was moaning on about Blair and Bush .... blaming them for kicking off the Iraq war ...... as I leaned over to kiss Heather . As we kissed I felt Heather's cock through her soft panties..... I sqoze her cock in my hand and felt her slowly begin to relax as we became more intimate. I put my hand inside her stylish pink jacket and felt her ample breasts..... they felt so real, she must have had an expensive boob job somewhere down the line.

At that point Brian looked as us through the rear view mirror and realised we were n't listening to his political rant ...
" Are you two having fun back there ? " he asked .
" Keep your eyes on the driving ... keep your hands on the wheel..." I replied... in the words of that corny old pop song .

Soon we reached the lake and parked in the cafe car park.
Brian went to the boot for his cam corder shoulder bag and passed it
to me through the car window. I took the cam corder out... it was all charged up and ready to go .

We walked along a path beside the lake then stopped to admire the view. I panned the camera out across the lake then onto Brian and Heather standing beside me.
" I'm going to make you a movie star... " I said to Heather ... joking.
Heather smiled and waved at the camera.... " I'd love to be in a real movie ," she said " I could play two roles... one as Heather and one as some guy.... I wonder if anyone would realize it was me playing both roles ?"
I looked at her brown eyes.... her auburn hair falling on the shoulders of her pink jacket... she looked so feminine and attractive. I looked at her slim legs in those black stockings and the high heeled ankle boots with golden chains. It was hard to believe that Brian.... a middle aged guy.... had pulled such a young beauty !

It was a warm, September afternoon in 2003.... a year that had been dominated by America and Britain's invasion of Iraq. Saddam's statue had been toppled and Saddam had fled Bhagdad as his once powerful regime collapsed around him.
There was endless TV coverage of events and we were beginning to realize that this Iraq war was going to go on for years and years. Blair and Bush had landed us right in it !

There was of course other... less serious news going on at that summer... Posh Spice and Becks had left the UK to go and live in Madrid. The Cheeky Girls had arrived from Romania to become a sexy pop sensation.
It was also in 2003 that the first Harry Potter novel was published... a book that was soon to become a series of blockbuster movies.
I ll always remember 2003 for the fabulous summer we had in the UK .... for once we had enjoyed long, warm summer days with lots of sunshine !



We walked on and took a path that led deep into the woods. There was the smell of pine on the warm breeze.... the oak and ash trees were showing the first signs of autumn colours..... there was the sound bird song.
I turned my cam corder on and filmed Heather walking along in front of me.... her high heeled ankle boots... not the best footware for this rough woodland path ! She turned and gave a wave at the camera.... then she beckoned me with her right hand..... that cheeky gesture will look great on the video I thought. Her light, pink summer jacket.... her black pleated skirt and black stockings.... she looked sensational I just had to zoom in .
At that point Brian stopped and looked back... he was impatient that we were n't keeping up.... " Come on you two " he said, "we 'll never get there !"
" Cool it Brian, " I said, " I'm getting some valuable footage back here ! "

To be continued.....



.

 

[Autolycus]

Thank you Shiningstar for a story that is different to possibly any that has been published here in the past. -Looking forward to the next episode.

 

[Shelby29]

To the Woods!

Chapter 1​

It was a warm, autumn afternoon when Brian picked me up at my flat and we drove into town. On the way Brian told me about the 24 year old guy
he 'd met..... Steve...... who was a cross dresser. He had arranged to meet Steve in the lounge of the George and Dragon at 2 pm.
" Steve will be in his female persona , " said Brian, " so we must call her .... Heather.... "
"OK " I said, "will do ."
I was a little bit surprised.... how did Brian.... a 53 year old , middle aged guy.... pull a 24 year old cross dresser ? Ok, Brian was a good looking, well hung guy.... but there was a huge, 30 year age difference !
Brian was big into cam corders back then ... in 2003.... and liked nothing more than making sex movies on video tape. That's where I came in.... I was his favourite cam corder guy !
He taught me how to use his expensive cam corder.... how to zoom in for close ups..... I was becoming quite the expert !
" Is Heather up for a bit of filming ? " I asked Brian as we drove along.
" Yeah, she's up for it , " said Brian, " I promised to buy her some gear as a sweetener .... "
" Gear ? you mean drugs ? " I asked.
"No" said Brian , smiling..... " I'm going to treat her to some sexy underwear..... I think she deserves it.... it's an expensive game being a cross dresser.... you need two sets of clothes..... I feel I v'e got to help the poor girl out ."

We arrived at the George and Dragon just before 2 pm.
" I'll have a swift half with her.... then we'll walk over to Matalan... " said Brian . I stayed in the car while Brian went into the pub to meet Heather.
Brian was in the pub for about 15 minutes, then I saw him leave with the attractive Heather. They set off walking to Matalan.... a big store not far along the main street.
I had a 30 minute wait.... sitting there in the car park of the George and Dragon ..... fantasising about an afternoon of sex. At last I saw them.... walking along together.... Heather carrying a posh Matalan carrier bag. I opened the car door and got into the back seat to allow Heather to sit up front with Brian. To my surprise she put her carrier bag on the front seat then came and sat in the back with me !
" Hi, I'm Dave.... " I said... shaking her hand.
" I'm Heather , " she said, smiling shyly. The brown eyes.... the auburn hair on her shoulders.... those breasts outlined by a thin, pink blouse .... she looked sexy and attractive....... I was so impressed !

On the short drive to the lake we chatted about this and that.
As we chatted I could see that Heather was quite nervous..... after all she was in a car with two older guys she hardly knew.... Brian age 53 me age 43.
I casually put my hand on her knee and rubbed up and down her black stockings. She did n't flinch ...... which only served to make me even bolder... I moved my hand up and under her black , pleated mini skirt. I reached her panties and felt the outline of her cock getting hard and erect.

Brian .... in the driving seat..... was moaning on about Blair and Bush .... blaming them for kicking off the Iraq war ...... as I leaned over to kiss Heather . As we kissed I felt Heather's cock through her soft panties..... I sqoze her cock in my hand and felt her slowly begin to relax as we became more intimate. I put my hand inside her stylish pink jacket and felt her ample breasts..... they felt so real, she must have had an expensive boob job somewhere down the line.

At that point Brian looked as us through the rear view mirror and realised we were n't listening to his political rant ...
" Are you two having fun back there ? " he asked .
" Keep your eyes on the driving ... keep your hands on the wheel..." I replied... in the words of that corny old pop song .

Soon we reached the lake and parked in the cafe car park.
Brian went to the boot for his cam corder shoulder bag and passed it
to me through the car window. I took the cam corder out... it was all charged up and ready to go .

We walked along a path beside the lake then stopped to admire the view. I panned the camera out across the lake then onto Brian and Heather standing beside me.
" I'm going to make you a movie star... " I said to Heather ... joking.
Heather smiled and waved at the camera.... " I'd love to be in a real movie ," she said " I could play two roles... one as Heather and one as some guy.... I wonder if anyone would realize it was me playing both roles ?"
I looked at her brown eyes.... her auburn hair falling on the shoulders of her pink jacket... she looked so feminine and attractive. I looked at her slim legs in those black stockings and the high heeled ankle boots with golden chains. It was hard to believe that Brian.... a middle aged guy.... had pulled such a young beauty !

It was a warm, September afternoon in 2003.... a year that had been dominated by America and Britain's invasion of Iraq. Saddam's statue had been toppled and Saddam had fled Bhagdad as his once powerful regime collapsed around him.
There was endless TV coverage of events and we were beginning to realize that this Iraq war was going to go on for years and years. Blair and Bush had landed us right in it !

There was of course other... less serious news going on at that summer... Posh Spice and Becks had left the UK to go and live in Madrid. The Cheeky Girls had arrived from Romania to become a sexy pop sensation.
It was also in 2003 that the first Harry Potter novel was published... a book that was soon to become a series of blockbuster movies.
I ll always remember 2003 for the fabulous summer we had in the UK .... for once we had enjoyed long, warm summer days with lots of sunshine !



We walked on and took a path that led deep into the woods. There was the smell of pine on the warm breeze.... the oak and ash trees were showing the first signs of autumn colours..... there was the sound bird song.
I turned my cam corder on and filmed Heather walking along in front of me.... her high heeled ankle boots... not the best footware for this rough woodland path ! She turned and gave a wave at the camera.... then she beckoned me with her right hand..... that cheeky gesture will look great on the video I thought. Her light, pink summer jacket.... her black pleated skirt and black stockings.... she looked sensational I just had to zoom in .
At that point Brian stopped and looked back... he was impatient that we were n't keeping up.... " Come on you two " he said, "we 'll never get there !"
" Cool it Brian, " I said, " I'm getting some valuable footage back here ! "

To be continued.....



.

Looking forward to reading lots more...

 

[shiningstar]

Chapter 2

We walked deeper and deeper into the forest.... there were waist high ferns.... there were trees fallen across our path.... blown down by last winter's storms. Sunbeams shone down through the branches of the trees..... what a fabulous day I thought to myself.

We reached a small pond with oak , ash and holly trees growing around the edge.... their roots exposed ..... there were reeds growing all around the pond.... it was an idylic woodland scene ! Two ducks took flight and landed on the opposite side of the pond ..... we'd disturbed their peaceful life.
Brian sat on a nearby log as Heather stood close beside him. She took off her stylish pink jacket and hung it on a nearby branch. I got a shot of them together and began to zoom in . Heather looked sensational.... her lovely breasts outlined in her thin, pink blouse. I zoomed in as she unbuttoned her blouse to reveal her pink bra.

Brian ran his hands up and down her legs, raising her skirt to show she was wearing black suspenders. Heather seemed so calm and relaxed in front of the camera ..... as if she'd done this kind of thing many times before.

" I think we 're ok here," said Brian , looking round....
"if anyone comes we can split up and walk away in opposite directions. Brian stood up and took off Heather's pink blouse..... he folded it and laid it on the log. Heather unhooked her black, pleated skirt and took it off.
She looked like sex on legs.... standing there in pink bra and pants.... black stockings and those cute ankle boots with the golden chains. Brian unzipped and pulled out his huge cock.... I could see he was excited.... " Heather smiled.... looked round at the camera and then took hold of his cock in her right hand.
She wanked him slowly as they kissed ... right there in the middle of the forest. Brian unhooked her bra as Heather kept wanking his cock.... I zoomed in to get a close up of her hand giving Brian such erotic pleasure.

Porn scenes like this are usually filmed in some seedy flat or film studio ... to film out there in the woods.... with trees and nature all around... was a bit special.
Brian loved to get his sex life on video....
" When I'm in my 70's and cant get it up anymore , " he once told me..... " at least I'll have these videos to look back at a time when I was horny and up for it !"
On that warm....September afternoon... Brian was definitely horny and up for it.... he was loving every minute !
I pulled back and got a wide shot of Brian and Heather with the trees and the pond in the background. Heather turned to the camera as if to show off her lovely, firm pair of tits. I thought I saw the feint signs of a scar where the silicone implants had been put in..... but other than that they looked pretty perfect to me .

I wondered how it would feel if I had the operation and got myself a nice pair of knockers .... would they make me more attractive to men... or would men look at me as kind of freak ?

Brian put his hand inside Heather's panties and pulled out her large, erect cock. She had everything.... a perfect pair tits to turn on every man and a thrusting.... 8" cock enough to satify anyone !
Brian knelt down and took Heather's cock in his right hand. I zoomed in for a close up as he pulled back the foreskin to reveal a lovely red knob. He began sucking.... at the same time Heather began deep breathing and let her head fall back. She put her hands on Brian's head and pulled him to her as her cock went in and out of Brian's mouth.... Brian was giving her deep throat !

I wanted to join in.... I wanted to get a piece of the action but I knew my job was to operate the cam corder and get some hot video.
That in itself was fun... I was enjoying it.... I could n't wait to see the footage on Brian's wide screen TV.

We were living in incredible times ..... times when anyone could get hold of a cam corder and begin making sexy movies. Then there was the Internet ..... even way back then in 2003 Brian was putting a few movies on the net.... that wonder of modern communication.
The internet by 2003 was already full of a million erotic pictures and sexy movies. For years we'd had to send away to Germany or Denmark to get hard core magazines or videos. We'd face arrest and prosecution at the airport under the obscene publications act ! Now with the magic of the internet.... everything was available on line.... in full living colour !

Meanwhile Brian was having the time of his life with this 24 year old tranny .... and Heather was enjoying herself too. I zoomed in as Brian put his hands on her slim waist and began sucking her tits. Her nips were big enough for Brian to suck and bite ..... she teased him as he tried to lick and bite those lovely nips. Heather put her hands on Brian's shoulders and pressed her cock against his.
As Brian sucked Heathers tits and slowly wanked her cock... I could see that Heather was in raptures..... " I'm going to cum ," she said at last.
Brian knelt down on the dry ground and wanked her hard cock.... Heather put her hand on the branch of a tree to support herself. Soon her body convulsed and she came...... I saw thick, white cum squirting onto the dusty forest floor. I zoomed in to get that look of extacy on Heather's face as Brian stood up and wanked himself off.

It had been a good sex session... one of the best I can remember for a long time.
I turned off the camera ... I had about 25 precious minutes of video. I wondered if Brian would eventually put this sexy forest session on line ?
Heather had no objections.... no one would ever recognize her in that auburn wig and heavy make up. Brian on the other hand might be recognized by one of his workmates logging onto some obscure porn channel.... but he did n't give a stuff !

Heather put her clothes back on and made herself respectable... then we set off walking back to the lake.
It was... Mission Accomplished... Brian had had a good time and he now had some super sexy video that would keep him happy in his old age !
Heather certainly enjoyed being fondled by an older guy.... I think she secretly got a thrill from having all the attention of two older guys.... both old enough to be her father!

At last we reached the lake to see the sun going down in the west ....its golden light sparkling on a thousand tiny ripples .
On the car ride back to the George and Dragon I managed to make a date with Heather for the following saturday afternoon..... I promised to buy her some sexy underwear then we'd go back to my flat for a hot session. Once more I put my hand on Heather's black stockings and felt my way to her panties. I found it fascinating that a guy would go to so much trouble to look like a girl.... even going to the operating theatre
for breast implants..... but then ... it had been going on for a long , long time. Back in the 1970's it was hip for guys to look feminine.... glam rock was full of guys in full make up.... there were gay clubs everywhere.... something strange was happening in western society .
As Ray Davies wrote in his song... Lola....

Girls will be boys and boys will be girls
It's a mixed up, muddled up, shook up world
Except for Lola

Yet for all that it seemed to me that it was men who were doing all the changeing... it was young men who were acting and dressing female.... I did nt see that much in the other direction !


It had been a good day filming Heather and Brian ... deep in the woods beside the pond. Meeting a guy with such lovely breasts up close and personal had given me a lot to think about. I admired the way Heather dressed and the trouble she took to look so glamorous and sexy .
I looked forward to meeting her again next saturday afternoon... I knew we'd have a good time together. I might even get the phone number of her breast surgeon !

THE END

.

 

[Autolycus]

Well! The second half of the story was everything the first had promised. For me, boys should be 100% boys but there is something about the likes of Heather that does account for more than just curiosity.