My first time in the woods to a straight guy (true story)

Born a boy, I've been dressing for as long as I can remember. I'm 27 now, but I have a few vague memories of roaming around the house playing dress up aged 5 or 6, and dress up in this case invariably pulling on one of my sister's dressed. Every other outfit my parents got me was neglected - I'd always gor straight back to the dress. As I got a bit older I used to sneak into my mum's room while she was at work - and when I'd wangled the day off school somehow - and try on pairs of her panties and suspender belts. It wasn't really sexual at all at that point - at least not until I was about 14. The it became sexual without me really realising it - I would get an erection whenever I stripped off and put my panties and heels on.

By the time I was 15 I'd built up quite a wardrobe. I saw that it was hidden from my mum but in hindsight she definitely would've known it was there. Indeed I know for a fact she did, as some years later she told me. At the time though it was my own private world. People at school used to call me girly and, with my clothes off and from the back, you wouldn't have been able to tell what I was. I was slim, had a pert little bum and had shoulder length blone (natural) hair. I'm not exaggerating if I say that I bore a resemblance to a young Daniel Evangelista (I'm sure most of you know who that is).

I was painfully shy, however, and so my dressing - at this point I could turn myself into a very attractive teenage girl - was saved for my room. By this point - aged 15 - it had also taken on more of a sexual component. I loved dressed however I felt, but if I was feeling horny I'd wear sexy lingerie I'd bought online - corsets, boots, stockings etc. - and I'd lie on my bed thinking about boys at school and older men who'd come round sometimes and fuck my older sister next door. I used to get soooo jealous of her at this point. I would lie naked under the covers in my bed, listening to the creaking back and forth that would be coming through the wall. I'd imagine he was fucking me, and I'd get changed sometimes while they were doing it and tell myself that I was going to go down to the sandunes near to where we lived and let one of the men down there (anyone) fuck me. It was a notorious cruising area and I was sure that someone would fuck me if i went down there and just stuff my arse in there air. I was so horny. I didn't do it though - too shy basically.

My first experience was with a guy from school who was two years above me. We used to chat on MSN Messenger, and one time when I had a few drinks (my sister's wine) I sent him some pictures of me dressed. We arranged to meet secretly near my house when he was at a party. I drank in my room then went down to soom woods round the back of a churchyard where he was waiting for me. We kissed, he fingered me (I didn't really like it - it felt like I needed to poo!) and then a gave him a blowjob until he cummed in my mouth. It was OK for a first time I suppose, but I hadn't really 'done it', had I? He went off sheepishly back to the party whereas I went to the toilet in another local pub to clean myself up a bit. This turned out to be a fateful decision. Despite only living half a mile down the road, I wouldn't end up getting home for another hour and a half yet.

After I was done at the pub I started to make my way up the road to my house. Terrifyingly, I spotted some people from my school sitting on a bench drinking, and they were obviously going to the same party Josh (the older boy from school) had been to. Worse still, they recognised me and started to holler at me to come over. At the time I wanted to sink into the ground - I was dressed remember, and could still taste another boy's cum in my mouth. I tentatively went over as there was no where to hide. I hoped I guess that they just wanted a lighter or somethng.

And yet...they were all really nice. It was three girls and one boy, and they said they knew I was transgender and it was fine they accepted me. It felt amazing actually, but things were already getting a bit more progressive in attitudes at that point. Plus they were drunk, and I soon got drunk with them. I smoked some weed too which made me feel really horny and tingly in my pants. After about half an hour I told them I'd better go home and they were all huggy and kissy and "oh it was so lovely to meet you etc". Lol drink!

So walking up the hill I noticed a man looking at me from the entrance to the gym as I walked past. I.e. looking at me hard, especially at my arse. He was older, mid-40s by the look of it, and big and muscly. I was wearing a blue denim dress, black knee high boots and coffee coloured stockings. I got a bit of the way up the road and looked to see if he was still looking at me. He was. Normally at this point I'd carry straight on up the road to where I lived, but this time I made a diversion at the fork and headed towards a wooded area (we called it the 'forest' when we were kids). Before I did that though I stared hard at this man, whose abs I could see through his button down shirt. Then, just before I walked away, I turned and I lifed my dress to reveal my ass. I was wearing a little black thong and I inclined forward a bit and suggestively rubbed my butt with my hand. We were only about 70 yeards aparts and my heart was beating like a hammer in my chest. I then started at him hard again before heading on into the woods. I turned a bit as I got into the undergrowth on the footpath and I saw that he looked around and then started to follow me. I carried on walking for about three minutes and then I stopped and went into a little clearing on the side. My heart was beating like anything at this point and I was shaking a bit with nerves. I went a bit further into the clearing and put my leather jacket on the floor and sat on it.

I sat there and I waited for what felt like forever. Then, suddenly, I heard some sticks breaking underfoot. It was him! I could see it was him from the cobalt blue colour of the shirt I'd seen him in - pretty distinctive. I hesitated for a moment, and then I realised that it was probably too late to go back: he would probably see me if I didn't move anyway. So I hissed at him a couple of time and he started looking in my direction...and then he started coming toward me. I was properly shaking at this point and I think he saw that I looked nervous because when he was stood a few feet away from me he laughed a bit and asked if I was alright. I replied with something stupid - "you want to sit down for a bit?" I think it was.

He said he would though, and almost as soon as he had he started to kiss my neck. I tried to push him away but he carried on. I was quite tipsy by this point and I didn't think he knew that I was a boy. He wouldn't have - as I say I was totally convincing. He started to stroke my leg and I started to get hard. I tried to move his hand but he carried on, moving in tentatively closer to the front of my panties. The bulge was visible but he didn't say anything. To sort of pre-empt it - and prolong the fun before he found out and got angry - I turned over on all fours and got his cock out. It was soft and then it went hard in my mouth, a big veiny thing - easily the biggest I'd seen. He was tanned all over too, and his stomach was rock hard.

He started to wank me off too - he'd found my little cock at this point - and then he put his finger up my ass. It still felt sort of weird. He started to tell me that he knew who I was, and knew - more importantly - what I was, and that he'd seen me walking past sometimes. I told him where I'd been that night - not everything mind - and told him that I wanted to have sex that night. I sucked him a bit more and while I did so he got some cream out of his back and rubbed it on my bumhole with his fingers. He then put it on his dick and made me turn around to face a nearby tree on all fours. I felt his strong arms take hold of my hips and I felt the tip of his cock go inside a bit. It was soo painful. I told him to stop and he did for a second before pushing again. After some initial pain this time it went right in. As it filled up my arse I started to cum a bit (pre-cum) and shivers went right through my body. He did it gently at first but after a bit of this he was hitting it solidly from the back. I started to cum properly after about a minute. It then felt slightly uncomfortable him riding me for about a minute beofre it started to feel good all over again. I came twice more and the last time I did he grunted and unloaded his semen inside me. He bit my neck and I was wanking my cock as he did so. I squeezed my arsehole around his dick in order to get every last drop out of it. As he pulled out he was still hard and I felt the cum dribbling down my leg. I was still on all fours, wiping some of the cum off with a spare pair of pants I'd brought with me in my bag, when he scampered right off without saying anything bar "see you later". My arse was on fire and so I just lay there smiling to myself.

When I got home I had a shower and sat up in my room. Everyone else was out so it was no stress. As I got ready for bed I put some of my stuff into the washing basket and I found a note with the guy's number that he'd obviously slipped into my pocket before he left. I hadn't expected to see him again but we set up quite a few rendezvous like this over the next two years - until I started at college. I'd wait for him somewhere - he came round my house a few times when everyone was out - and he'd turn up, fuck me and go. By the time I got to college I was an experienced anal queen ;), thanks to that man, though when I returned a couple of years later he and his wife - because I found out he had a wife - had left town. Thanks, then, if you're reading this. Sometimes, to this day, when a guy is fucking me I close my eyes and pretend it's you in those woods on that night in the summer way back. That usually makes me cum ;)

Selina xxx