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Meet Number 1  

AmberCandygirl 50T
0 posts
3/9/2021 9:46 am
Meet Number 1


It seems like such a long time ago now.

How to start?

Where to start?

The beginning or somewhere hot then backtrack?

Maybe with just with the headline news?

Just over three weeks ago Amber sucked her first cock and swallowed a mouthful of warm cum.

Circumstances meant that for once (and the opportunities are very rare indeed) I knew I had Friday night to myself. That if I were lucky I could spend the whole day dressed and perhaps in the early hours of Saturday either invite a man into my home or (as actually happened) jump in my car and drive to his (whoever he turned out be).

For once rather than fantasise and do nothing about it, which invariably leads to me ending up fingering myself on a webcam in a chatroom somewhere whilst watching someone wank over me, I mentioned to an admirer I'd exchanged a of emails with over the previous months that I might have a small window of opportunity. To my great surprise, he replied saying that the timing could work for him too.

I spent the next few days trying to come up with reasons not to meet. Of which there were a million and one. Whilst at the same time becoming more and more excited the idea.

Come Friday I was a bag of nerves. I was still stalling a little and I checked my messages with not a little trepidation. He had sent me his phone and asked me to send him something naughty during the day. I put his into my phone but told myself I probably wouldn't use it.

Having just finished working on a long contract I had the whole day to myself to prepare. I was too nervous to eat anything all day and subsisted on caffeine and copious cups of tea.

I painted my toe nails. Took a long bath, shaving my legs, chest, genitalia and armpits. I took a picture on my phone of my smooth legs in the bath tub and nervously sent it to him knowing that now he would have my too. Looking back I was deliberately painting myself into a corner whereby unless it was him that cancelled I would feel obliged to come through.

I moisturised all over, slipped into some stockings and heels and took more pictures which I then sent directly to him. I imagined him at work hiding a hard on beneath his desk, trying to concentrate on the computer screen, only able to think of me. It made me uneasy and hot as hell at the same time.

The day stretched out in front of me. I played on cam on birchplace for all to see, I chatted to a few people on tvchix and shemalechatcity, I practised my make-up over and over so that later I could throw something basic together quickly. I tried to think of all the ways I could get out of what I was thinking of doing and nearly accepted the first excuse given to me.

For various reasons (his and mine) any meet had to happen after pm. 9pm it was obvious there was a party going on upstairs. There was no way on earth I could receive visitors. As I wasn't going to be able to contact him until later and the plan (in my head anyway) had been to accommodate him at my house I figured that nothing was going to happen. In lots of ways I was relieved. I waited for him to contact me so that I could break the bad news.

It was then, knowing it probably wasn't going to happen, that I realised I was disappointed. That I needed to do this, that I wanted to be treated like a girl, to experience a cock even if it was only once. When he finally texted I replied saying if we did meet it would have to be at his as there was a party taking place. His reply didn't fill me with confidence but it ended asking me to call him. We had never spoken and I was terrified. It took me almost half an hour to pluck up the courage to hit dial.

He answered, "Hello Amber". I was so nervous my voice was almost breathless and probably (thankfully) more girly than normal. He explained that it was a shame I couldn't accommodate and that maybe it was okay. We'd finally made a physical (phone) contact and perhaps we should build on that and take things slowly. Plus he wasn't at his normal location ( minutes walk from me) and so it would be a minute drive for him even at this late hour. I didn't know what to say. I had spent the entire day building up the courage to do this, something, anything.

I hadn't had anything to drink so I suggested I come to him but warned that I wouldn't be able to arrive dressed as I needed to put some petrol in the car and that would require being out in the open. He said if we were going to meet we should have a minimum set of expectations. I told him how much I wanted to be kissed, to feel hands on my body, to be a girl. He seemed to want more of a reason, that that wasn't enough really and said 'Anything else?'.

I told him I would suck his cock.

Finally he gave me his and said it was okay, I could change there.

I was so nervous. I showered again, slipped on a pair of cute panties under my jeans and shirt, stuffed a wig, bra, panties, heels and a couple of dresses along with some basic make-up into a bag and went out to the car.

Even when I was stood filling up the car all I could think was 'I'm driving to someones house I don't know to suck a strangers cock'. I didn't know how I felt about that only that it was exactly what I planned to do.

I arrived well after :. The cul-de-sac where his house was was thankfully quiet and devoid of any waking neighbours who might see me. As I pulled into his drive he opened his front door and stepped out to welcome me.

Although I wasn't dressed he greeted me as Amber and ushered me inside. I could see into the living room and he had a bottle of wine set out and two glasses. He asked if I wanted to sit down and chat briefly or if I wanted to change first. I mumbled that I would prefer the latter option and he waved me upstairs telling me where the bathroom was, "Take your time Amber, come down when you're ready".

I locked the door behind me and stripped off, shaking, my heart beating too quickly.

I slipped on some lace panties and matching bra before slowly pulling on hold-up stockings. I chose the first dress that came to hand and pulled it over my head. I slipped my stockinged feet into my heels.

I noticed I had stupidly only brought half of my make-up which though annoying at least meant I wouldn't be able to keep him waiting for too long. I applied foundation, eye liner, eye make-up, lipstick and mascara and then put my new short wig (which as an aside I'm not 100% convinced ) on. Less than 10 minutes in total. Part of me knew I was rushing, part of me needed it to be a rush so that I couldn't have the time to overthink things and back out. I took a deep breath and went back downstairs.

He stood up as I entered the room, told me how pretty I looked, asked me to twirl around for him. I did. I could hardly look him in the eye and kept my sentences brief (and I hoped girly). I was so nervous and yet it felt right to be dressed as a girl and hearing compliments.

He poured me a small glass of wine (I said I was driving) and we sat down together on the sofa. Bless him he tried to engage me in conversation but I was just too damned nervous to really along so I kept dropping my eyes from his eyes to his lips and then back so that he knew it was okay to just go ahead and kiss me. Mustering up every last bit of courage left in me I placed his hand on my stockinged thigh to hopefully encourage him to just go for it. I knew if he didn't I would never be able to actually say anything out loud and that the longer he took the more I would just want to run away.

He kissed me.

I opened my lips to let his tongue into my mouth and greedily kissed him back, closing my eyes hoping he would just let loose with his hands. I lifted my legs into his lap so he could have free access to them and let him kiss me as deeply as he wanted, licking at his lips whenever he paused for breath to signal he could continue if he wished.

I needed to know if I was turning him on and rubbed my fingers over his crotch. I could feel his cock hard in his trousers and and I massaged it through the fabric. His fingers found my panties and my hard freshly trimmed and shaved cock pressing against the lace. He gently pushed me back so he could see it framed in my panties.

I rubbed him again letting him know I needed to see his too. He loosened his trousers and opened them. It wasn't huge for which I was grateful (although I would love to be confronted with a cock which did scare me too) but it was hard and I didn't care what size it was as long as it was obvious I was turning him on. I touched it, felt its warmth in my hands, slowly stroked it whilst he kissed me.

I attempted to get on my knees in front of him so that I could take it in my mouth but I think he misunderstood my attentions and thought I wanted to lie on the floor. I let him control proceedings (as I wanted to be a good submissive girl) and lay on the blanket and he lay on top of me kissing and touching me.

He asked me to take my panties off and so I slipped them over my heels and dropped them on the carpet. He stroked me slowly for a while and I enjoyed feeling his cock brushing against mine. I held them both together and stroked them both at the same time listening to him tell me how pretty I was and how much he had fancied me for the last months. I kept raising my hips up towards him in the hope he might start touching my bare thighs and ass. Finally I felt his fingertips on my tight hole slowly circling it.

He asked me if I had any lube.

I did. Upstairs in my bag. I asked if he wanted me to get it.

"Yes Amber, be a good girl and run up and get it."

Even though I was in my heels I was quick and I handed him the tub when I returned. I lay back down in front of him and he lubed up a finger and slid it inside of me, kissing me at the same time.

I couldn't but stroke myself. He sat back and watched for a while before telling me he wanted me to cum for him. I needed something inside of me so slipped my own fingers into my ass and stroked myself for him. He encouraged me along verbally and before long I came, my whole body shaking as he descended on my cum covered cock and balls, licking it all up.

He kissed me forcing me to taste my own cum in his mouth and told me he wanted to cum inside of me. For the first time I said no. There were no condoms to be seen and although his cock would have probably been a perfect size for my first A level common sense screamed out at me that it might be the wrong thing to do.

"Okay. Where should I cum then Amber?"

Not his fault - he shouldn't have let me cum - I was already out of the room mentally - note to self until completely relaxed with these things NEVER cum first but I just wanted everything over now so I blurted out, "In my mouth". Firstly because I thought he might be upset about me saying no to him me, secondly because that was what I'd promised on the phone.

Thirdly because I desperately wanted to suck a cock

He stood in front of me and I let him fuck my face. His hands in my hair, his cock at the back of my throat almost gagging me. I worked my tongue and lips all over it and when he finally came I almost choked as thick wad of his cum hit the back of my throat. It was all over too quickly, I hardly even tasted it or savoured the moment (again mine not his fault).

I sat there on the carpet, his cum cooling on my stockings, my own cock wet and limp on my thigh feeling empty. Not dirty or guilty or used just empty, unsure of how I should feel. Shy and vulnerable and desperate to just leave and work out what my emotions were in a less foreign place.

I made my excuses, got changed, removed my make-up and left soon afterwards hoping I hadn't offended him as the mixed emotions were personal to me rather than directed at him.

Will I meet him again?

No and I won't continue to contact him online either BUT I have to underline strongly that's not a reflection on him personally.

He was, if not exactly what I was looking for, a perfect gentleman and I can only thank him for helping me achieve my desire to suck my first cock and I hope I didn't disappoint him either. Unfortunately though he is probably as inexperienced as me and I need a slightly dominant tv or admirer I feel more of a physical attraction to (as well as mental - which is what I felt towards the man I met - a mental attraction which had built up over time) who will hold my hand a little and take things a little slower, teaching me how to please them and allow me to learn to enjoy pleasing them and how to be a good submissive.

When I will ever get the opportunity again though to do such things is anyones guess.

I'm glad I seized the chance I got.

I hope another comes my way. I did very much love having a cock between my lips. I would dearly love to be taught how to savour the moment for longer too.

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