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By (user no longer on site) OP
over a year ago
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My First Time
I was sixteen when I joined the Merchant Navy and after ten weeks training at Gravesend as a catering boy was flown to Jeddah to join my first ship. Although being quite small I was good at sports and had my share of girlfriends but nothing too serious. My main passion was dressing up in my older sisters and sometimes my mothers clothes, it was such a thrill and I so wanted to take some of my femme stuff with me but as we were flying was worried about being caught out at the airport. There were about ten of us flying from Heathrow and we were put up in a hotel in London for a couple of nights so that we could meet each other and fly out together. This is where I met Paul, he was twenty seven, a steward, the phrase tall dark and handsome fitted him perfectly, he really was quite a dish and I thought to myself, a hit with the ladies. Although most of us stayed around the hotel in the evenings Paul would venture into town, anyway one of the others explained to me that he had worked with Paul before and that he was into tranny’s as he put it and that he had most probably gone looking for some fun, but that I should not be put off as he was a nice guy, and kept himself to himself. Obviously he didn’t know of my secret passion and far from being put off, all I was thinking of was how I was going to get to know Paul better.
Paul really was a good guy and looked out for me and another catering boy during our flight and on board the ship, anyway after two weeks in port we were told we would be sailing back to Falmouth to go into dry dock for a week before setting off for America, this really was an exciting time for me as I had never ventured far from home before. The work wasn’t that hard and I soon got used to the routine and ship life, we had our own cabins with en suite which was great. I spent most evenings in my cabin, reading or listening to music or chatting to the others, Paul as was said kept himself to himself and although he would join in sometimes, he would spend most evenings in his cabin. In bed all I could think about was Paul and what it would be like to be dressed and with him. It took us about three weeks to get to Falmouth and we were given the option of going home for a few days or staying on board, I decided to go home although Paul stayed on board. My mother and sister we so pleased to see me but all I could think about was when would I have the chance to dress and have some fun with myself, eventually they decided to go shopping, I don’t think they had reached the end of the path and I was in my bra, panties, suspender belt, stockings and heels riding a candle as I stroked myself off thinking about Paul, I remember cumming loads then just laying there, thinking of how I was going to make it happen for real. The good thing was that I could take a nice bath, shave my legs etc and take some femme stuff back with me.
Once back on board one of the first guys I bumped into was Paul, I asked if he was going into town later, but he said that he had been and that it really didn’t do much for him, it was lunchtime so we still had evening meals to do, which Paul and I served during which I eventually built the courage up to say “if you are not going into town why not pop to my cabin and we can catch up with what I have missed and I can show you my new cassette player (as it was in those days lol) . We arranged a time of eight o’clock.
When we had finished and cleaned down I went to my cabin to get ready, after showering I sat at my mirror shaking like a leaf trying to blow dry my hair and put my make up on, once happy I started to dress, white lace panties and bra with a pink trim, matching suspender belt, lace topped tan stockings, 3” high heeled grey sandals, grey skirt and a white blouse, all my older sisters cast offs, in fact most of the stuff she threw out never made it to the bin. Dead on eight o’clock there was a knock at the door, weak at the knees I got up and went to the en suite “come in, will be out in a minute” I shouted. A quick touch up of my lipstick, a spray of Charlie, a final check in the mirror and a deep breath and I opened the door, Paul turned round and his jaw nearly hit the floor, “wow” was all he could say, I walked over to my cabin door and locked it, then turned to him, he must of seen how nervous I was and that I was lost for words “don’t worry” he said “your secret is safe with me” I remember explaining that he was the first person that had ever seen me dressed and he asked if I had a girly name “Angela” I replied, she was a girl I had fancied in school and the first name that came into my head. He started to speak again but I just walked over to him and kissed him, he took me in his arms and kissed me back, I felt his tongue on my lips and opened my mouth, we kissed passionately and fell onto the bed, “are you sure this is what Angela wants” he asked, I kissed him again undoing his shirt, “oh you can call me Angie, and yes she is sure” I said. He had a nice hairy chest and running my hand through it made me feel so girly, I kissed down his chest undoing his trousers and took them and his shirt off, then I slowly slid his boxers off, his cock was already hard but stiffened even more as I started to kiss it, then I run my tongue up and down his now throbbing shaft, 6” uncut, I couldn’t wait to get him inside my warm wet mouth and start sucking him, my first cock and it was even better than I had imagined, he held my head and slowly started to fuck my mouth, it was all too much and I came in my panties, then soon after that I felt him twitch, he said he was going to cum, expecting me I think to stop, but I didn’t, I wanted to swallow his cum, and god was there a lot to swallow, it tasted so good, as he lay there getting his breath back I licked him clean. “mmmmmm that was so good” he said. As we kissed again he started to undress me, my, blouse and then my skirt, I was a bit embarrassed that I had cum already but he just pulled my panties down, licked me clean and made me hard again “you taste so girly” he said. He came up alongside me and we kissed again, I could feel his cock getting hard again as we kissed and caressed, I reached down and slowly started to stroke his cock “I want you to make me feel like a real girl” I said “ and before you say anything, yes I am sure” I said as I handed him some Vaseline from my bedside table, he started to kiss me all over, and I loved him calling all my bits by their girly name, my breasts, my clittie, my pussy, it all just made me feel like a real girl, he slid my heels off, put some Vaseline on his hands and started to finger me, one then two fingers, all the while talking to me, relaxing me, he then put a pillow under my waist, spread my legs and looked at me “ yes I am sure” I smiled, he lifted my legs and placed his cock at the entrance to my pussy, slowly entering me, always looking into my eyes to check I was ok, when he was all the way in he came down on top of me and slowly started to fuck me, I was whimpering with pleasure, my clittie trapped between our writhing bodies, my stockinged legs wrapped around him, as he got faster I just remember whispering “yes, yes, cum for me, cum for Angie” this must of done the trick “now, now, all for you” he said, the feel of his cock exploding inside me making me cum too, we lay like that for a minute or two, kissing, panting, then he slowly slid from within me, the feel of his cum dribbling from my pussy was wonderful, I kissed down his chest again and licked my cum from his belly and he returned the favour. We then lay there talking about where we would take it from there, we decided to keep it discrete and we would meet in my cabin about once a week for some fun, we seemed to get away with it and what followed was perhaps the best three months of my life.
Sadly Paul paid off the ship when we were in Rotterdam, I was devastated and although he said he would write he didn’t. Mind you that was just the beginning of Angie’s adventures and when I get the time I will write about some more.
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