I had just moved into the country to a nice little cottage that my mother owned, she left it to me when she died. I had lived there for a couple of months, and began to feel at home and took to exploring the countryside. Across the lane from my house was a footpath lined on both sides by a tall hedge, it went past a large mansion house, which was the only other building for miles. The path led to a small wood, which I thought I would investigate at some time.
My name is Andy I was 23 then and loved dressing as a women (still do). One Saturday afternoon, it was quite sunny and warm. I felt very sexy and decided to get dressed up and walk down the footpath to the wood. I had never seen anyone at the mansion so I felt quite sure that I would not be seen. I put on a white suspender belt, dark tan stockings, white frilly panties, a fairly short flared black skirt, a pink short sleeved shirt and black high heels. I put my favourite dildo into a small bag along with a jar of lubrication cream, I was going to have a good time.
I left the house and set of down the path I loved the feeling of the wind blowing up under my skirt onto my bare thighs above my stocking tops. I could feel my cock getting harder as I walked on past the mansion house, I could hardly see it for the high hedge and trees that surrounded it. I walked on into the wood ducking under branches, I lifted up the hem of my skirt to around my waist exposing my suspenders and panties. The long grass was tickling my upper thighs and my panty covered crotch. My cock was really hard now, I began to stroke it and wank it as I went further into the wood, pulling my panties to one side my balls and cock came out into the open it was lovely to feel the wind around them.
I came to a little clearing, the grass was quite short a tree had fallen down at sometime the trunk was partly overgrown with weeds, It made a good seat. I sat down and slowly played with my cock with one hand, the other playing with my balls. After a while, I stood up and pulled my panties down to my knees I lifted my skirt up high and sat back down on the tree trunk the roughness of the surface and the weeds felt good on my bare ass. I took the jar out of my bag, opened it, took some cream onto my fingers of my right hand and began to rub it around my ass hole.
I continued wanking with my left hand as I pushed one finger up my hole working it in and out, lubricating it then I worked in another finger alongside the first and worked them both in and out. Then a third, my hole was ready for my dildo, it shone brightly in the afternoon sun as I rub on some cream I was getting very excited now, the dildo shagging my ass always gives me a huge orgasm. I placed the tip of the dildo against my hole it felt quite cool as I gently began to push it in, the end began to force open my hole stretching it further as it slowly entered, deeper and deeper it was soon as far in as it would go. I pulled it slowly out then pushed it back in, then out and in getting faster each time soon I was thrusting away like mad wanking my cock at the same time really enjoying every thrust.
Then from nowhere a man’s voice asked if he could help. I just froze, I did not know what to say or do. The man was middle-aged 46ish average height and build in smart trousers white shirt with an expensive looking tie. He did not wait to long for a reply - he just knelt down in front of me grabbed hold of my panties and took them off, he pushed my legs wide apart took my hand of the end of my dildo, then slowly he began to push it up me. Slowly at first then gradually getting faster, soon he was giving my hole a good fucking. I was still wanking myself really beginning to enjoy this new experience, having never been with a man before.
I looked at him, as he was ramming my dildo up me he was undoing his trousers with his free hand, he said he was sure I would enjoy the real thing more. He pulled the dildo out of my hole stood up took off his trousers and pants and knelt back down in front of me. His cock was quite a size bigger than mine, already erect the tip moist as he pulled back his foreskin. He took hold of my ankles one in each hand lifted my legs up high in the air the tip of his cock touched my open hole. He thrust forward in one movement his cock was totally embedded in my ass. I let out a big sigh, I was being totally filled by his cock each thrust he was ramming his cock as far into me as it would possibly go, his balls slapping into my ass each time.
I can tell you are enjoying this he said, as he fucked me some more. He suddenly pulled his cock out of me and told me to get up and turn round and bend over the trunk on my knees. I just did what he said, he lifted my skirt up out of the way, as it was covering my ass, and then I felt his cock back up inside me again. He fucked me for a little while longer then I could tell he was just about to cum he pulled out and sprayed my ass with his spunk. I could feel it running down between the cheeks of my ass and down the back of my thighs. He stood up and I got up and sat on the trunk. He picked up my panties, wiped his cock and balls in them and gave them back to me.
He said he owned the mansion house. He lived there alone and if I wanted to join him the next weekend at his house we could have some more fun but in more comfortable surroundings. If you do come, he said, come Saturday afternoon and to dress like a tart - fishnet stockings, mini skirt etc. Then he left.
I was totally amazed - the whole thing seemed like a fantastic dream but my sore ass and the cum dripping off me told me it was very real. My cock was still hard so I continued to wank myself off, having an amazing orgasm. Then I pulled on my panties, the mans cum soaking into them from my ass. It felt good, as I walked back up the path, I could feel the damp patches on my stocking tops where the man’s cum had run down to and soaked in. As I passed his house I was thinking about next weekend, should I go, or not. My ass felt quite sore from the pounding but it did feel good.