I had been wooed on line by my male friend for weeks - chatroom first then on webcam - now I was meeting him in real time for the first time - my first man!

I had been talking to John online for months - I met him in a chatroom for crossdressers and their admirers. We progressed to swapping emails and photos and then going on webcam. After three months of video chat, we had seen just about everything there was to see of each other - me always dressed for him and him often undressed for me!

When he asked me to meet him, I was scared but it seemed the right thing - we already knew what we each looked like and I trusted him. So, I said yes and then panicked for the next three days.

We arranged to meet in a carpark in the Ashdown Forest near where he lives at 2.00pm on Thursday. He told me it is a popular cruising place for men and for doggers so we would not look out of place! However, I was up at dawn, showering, shaving, creaming, and doing my makeup and hair. I have natural blonde shoulder length hair so I do not need wigs any more. I think I was ready by about 9.00am so spent the next couple of hours dressing and undressing, trying on this, then that, outfit.

Finally, I settled on a deep blue shirt with a silver thread running through it and a black skirt that I knew he liked, especially as it only came to mid-thigh. I matched it with my favourite black undies - lacy bra, thong and matching deep-cut garter belt - and black stockings and four-inch shiny court shoes. My make-up was the best I had ever managed and my lips were glossy and red. I looked a picture!

Then into the car and the two-hour drive to meet him.

Bang on 2.00 I got to the carpark and drove in - I knew I was looking for a large blue Volvo estate and sure enough it was there but parked in a bay for a single car. It meant I had to park a little away from him and get out and walk to his car - I knew he had planned that to be the case.

There were two other cars parked there with people sitting in them and I had to walk past both to get to John’s car. I plucked up courage, opened the car door, and swung my silky legs and shiny heels out. I stood up, closed the door, straightened my skirt, and started to walk slowly towards him.

I could feel the eyes in the other cars watching me as I tottered across the rough surface in my heels, my heart beating faster and faster and my confidence draining with every step. But finally, I reached the Volvo and with relief opened the door and slid in beside my real-life John for the first time.

We smiled and said a whispered hallo to each other and then he simply leaned towards me and placed a very gentle kiss on my lips. My first male kiss and it seemed so natural and right. For the next few minutes we made very polite and banal conversation but all the time the tension was rising and we both knew something was about to happen.

Finally he said, “Come here Tiff, I want to kiss you properly now” and he slipped an arm around my shoulders and drew me to him for my first proper kiss with a man - our lips met and parted, his tongue sliding into my mouth and around my tongue, our mouths locked together in the most beautiful moment of my entire life.

We stayed locked in each other’s arms kissing and gradually cuddling more intimately for a good five minutes and then paused for breath. I realised there were now four other cars in the carpark, all had single men in them and they were all watching us. That just excited me even more and I knew I did not want things to stop now.

We kissed again and this time his hand slipped to my thigh and slowly pushed my skirt up until my stocking tops were showing and his hand was caressing my bare flesh above them. He gently pushed my legs apart and continued to slide his hand up my inner thighs, until he reached my small silky thong. He slid his hand under my ass as we kissed until his fingers found my virgin secret entrance - my girly hole as he had called it in our video chats. He fingered it gently and then forced a stiff thick digit into me as I spread my legs wide to help him. The first time I had been entered by a man’s finger and my anal ring seemed to know to let this alien thing enter easily.

Then he whispered in my ear - “take me out and hold me”. Oh, just what I wanted. I reached down to his groin and felt an enormous hard bulge there. I found his zipper and gently pulled it down and then undid his belt and buttons and opened his pants. I reached into his boxers and found the thing of my dreams - I had seen it like this on cam but now here it was for real and actually in my hand.

I moved my fingers gently up and down the solid seven inches of uncut male flesh - my next first time - stroking a man’s cock as he kissed me and fingered my own tight little anus.

After a few minutes of this he pushed his hand into my hair and with controlled power eased my head down towards his rampant rod. As I lowered my face into his lap, it was the most wonderful thing to know I was about to take this big hard man-thing deep into my mouth and give him satisfaction like he had never known before.

I opened my mouth and took him in - just between my lips to begin but then deeper and then moving up and down and bobbing my head as he leaned back and moaned. Suddenly he tensed, grabbed my head, and thrust his cock deep into my throat almost choking me with the size of it. “Now!” he cried and with a gasp he exploded into my mouth filling me with thick salty cum that I just had to swallow as there was nowhere else for it to go. My sense of achievement was overwhelming - I had made my first man cum in my mouth and I loved every drop of it and every minute that he stayed in my mouth was ecstasy.

Finally I sat up and looked around the carpark as I wiped my lips with a tissue John gave me. Eight cars faced me, each with a solo man watching. I smiled with delight and gave John a long slow kiss of my own. “Come back to my place?” he asked. “Of course, darling” I replied happily. “Get your car and follow me then,” he said.

This time I opened the car door and swung my legs out with confidence - no longer the scared and anxious novice - now I was the experienced t-girl leaving her lover to walk back to her car and be enjoyed by my audience.

I sashayed across the long walk to my car, smoothing my skirt down as I walked, and giving each lonely man in his car a knowing look and a coy smile. My world had just changed for ever and I wanted them to know it. As I reached my car and opened the door, one man stepped out of his and simply smiled and said “nice one girl - I come here most afternoons - why don’t you come and see me next time”

When I had met my waiting admirer, I had not only had my first-ever male kiss but also, I had ended up letting him have the benefit of my first-ever attempt at giving head. I had been ecstatic with pride and pleasure when I had made him cum and, even better, I swallowed it all without even thinking. My slow walk back to my car in front of a bunch of solo male watchers in other cars, straightening my skirt and coyly smiling at them, had been a massive turn on. But now the best was yet to come - I hoped.

John drove out of the car park and I followed obediently behind in my own car just as he had told me to do, my heart aflutter with a mix of excitement, fear, and pure basic lust.

John drove for about twenty minutes to the small country town where he lived and turned into a quiet residential street. I had followed him all the way and had felt more and more apprehensive about what was to come but still so excited and curious. As we had stopped at traffic lights, he had waved to me and had made sure that he loitered long enough at the lights to make sure that any passing pedestrian noticed me and had a chance to look into my car and see my stocking clad thighs. It was a deliberate effort by him to show me off and I knew he was enjoying it - so was I!

He reached his house and turned into the drive but there was only room for the one car, not a surprise to him but not something I had thought about. I was forced to park on the street a little way past his house. I got out of my car and then walked slowly back towards him on my 4-inch heels, straightening my skirt again as I tottered towards him.

As I reached him, he leaned towards me, gave me a light kiss on my lips, gave me a quick fondle on my ass, before taking my hand and turning to go to the house. “That will give the neighbours something to talk about” he laughed, as I looked around, just in time to see two women standing on the other side of the road talking and watching us going through the open front door.

Inside the house he immediately took me in his arms and gave me the most wonderful passionate kiss, our hips wedged together and his hands pulling me close against his body. “Nervous?” he asked. “Yes” I whispered back. “Don’t be - I will be gentle” he said. “Well to start with anyway!” he added, with a sexy smile that made me go weak at the knees.

He took me through to his lounge, where we settled onto his leather couch and once more fell into an embrace where our lips seemed to be locked together for what seemed like hours. His hands gradually exploring my body and mine encouraged to do the same to him, before he mumbled in a dry-throated voice “How about more of what you did in the car?”