Date: Fri, 01 Mar 2002 15:10:35 +0000 From: Meno philist Subject: Submission for crossdressing section - "Help with my first period" part 1 When I was about 15 I had my first experience of a menstruating woman -- I had been a cross dresser of sorts -- as a little girl as it were, but as I began to be really aware of the difference between men and women, the one thing that really caught my attention was periods -- I had begun, aged about 14, to try wearing my own sisters and mothers sanitary pads, and a turning point cam when I spent a whole day, at school, wearing a pad, and really enjoying the feeling of it rubbing against me in my white cotton knickers. I had wondered what a period was like, and felt that the girly side of me should try to experience something similar. Then along came puberty, and I wrestled these thoughts with my attraction to women. I loved to hear the girls in class talk about their first periods, and by careful and discrete looking in their bags and sometimes lockers had established pretty much which girls wore pads and which tampons. My first real girlfriend let me fumble a bit, and on one memorable occasion warned me off because of my period -- I think I came in my pants pretty much instantly, but despite my best efforts got no closer. So one summer holiday, aged 15 I was staying with a friend, James, in his parents large house in Cornwall. James had 3 delicious sisters, all very different, all older than him. Staying for about a week, I had my own room, and vowed to wear a different pair of knickers each day, and really relish the opportunities at night time to be girly -- the door to the room locked, and so I slept all dressed up -- I had spent a fortune on knickers and had a white bra of my sisters as well as a pair of tights I wore in bed, and I have to admit which were very sticky after the first night, but by the second night pulling on a pair of sticky wet tights, anticipating spending the whole nights with my hand in my knickers, and the occasional finger up the bum was divine for an experimental little pervert. The one thing I had forgotten was any pads -- by now I was wearing pads fairly often, although I had not been brave enough to buy my own I had to be careful not to "borrow" so many that I would be caught. On about the third day I noticed a faintly worn pad in the bin in the bathroom, and on the grounds that no one would miss it, spirited it back to my room for the following night. That evening is parents were out until the next day, and his middle sister who was the only one there was charged with making sure we did not get up to anything we should not have. She of course took the opportunity to go to the pub, and so James and I watched a video he had secreted of frankly the most enormous cocked men fucking the most filthy looking women I have ever seen since into a state of submission. I was of course supremely excited by the time I went to bed, and after about 30 minutes by which time I assumed al was quiet I started to get dressed, but could not find the pad. I was too excited to think sensibly, so pulling on jeans and a t-shirt over knickers and bra I ventured out of my room onto the landing. James room was on the next floor up, and the room next to mine was his eldest sisters -- I slipped in as quietly as I could and closed the door behind me. I fumbled around until I found a bedside light, switched it on, and headed for a promising looking bedside set of draws. In here was a stash of underwear that made my eyes pop out -- I knew I should not take anything simply for fear of discovery, but I rationalised that if I was careful and did not make a mess I would be safe. After a lot of thought, and too much choice, I selected a set of underwear that seemed to start with a red and black suspender belt -- this I clipped on to myself, lowering my jeans to the floor, and then slipped them off to put on the matching knickers. The bra too I found, and stripped off my t-shirt to try. As I looked for stockings in a draw below found a single simplicity pad, quite large, and the pristine soft whiteness was too much for me. I pulled my knickers down and carefully placed it into the front of the knickers, lining up with my very very hard and dripping cock. It stuck out slightly above my waistband, but then again so did I, and I was rubbing myself softly through it when I heard a toilet flush. I could have reacted quicker, and I do not know why I did not, but in a stupor I stared at the door as the handle turned, and in came Danielle, the middle sister. She was quite beautifully naked, holding her breasts it seems, and in the other hand a wrapped up sanitary towel. "I thought it was James up to his tricks, but what have we here?" I could not say a word, and she walked over to me while I quaked. I could imagine the humiliation, my parents finding out -- I was hoping to at least hide the pad, but of course it was the first thing she noticed. "that's what I came in for you little cunt, I'm out of pads -- and I'm not wearing it now -- what are you doing?" It all came out, my confusion about my sexuality, my dressing up, my fascination with periods -- she remained silent the whole time, and I was beginning to hope she would feel sorry for me -- saying it all out loud I began to feel pretty sorry for myself. "You'd be ok as a girl -- let's see what I can make of you -- I always wanted to dress up James poor boy -- get some stockings on." So saying she reached to the still open second draw and took out a pair of beige stockings and a box of tampax. I obliged, and rolled them up my legs a little self-consciously. I was most aware of the pad as I turned towards her, and as I clipped my stockings onto the suspender belt I moved to pull it out. "No" she said, "Leave that there -- I think you will have to have your first period starting tonight". I blushed, but I was excited -- she kneeled again on the bed, and took a tampax out of the packet "These will be a good start little girl -- nice and slim -- - do you need instructions, or have you done this before?" I shook my head, and she peeled the paper off a tampon and handed it to me. I knew what she wanted me to do, but couldn't bring myself to say it -- I began to pull my knickers down again, over my stockings, but she stopped me. "Here, come up to face me -- your "hole" is in the wrong place, so ill show you " I was right up against her -- she had a divinely round belly that I was pressed against, and as I put one leg up on the bed she reached round me in what I thought was an embrace, and then I started to feel something pushing at my hole "Here we go -- relax, it's easy". And it was, it seemed to pop in, and I at once came in a shower of cream on her belly in front of me -- she recoiled back, almost yanking the tampax all the way out of me, and I stood still again, feeling the discomfort of the thing half in my hole, half out. "Lick that up you cunt!" she screamed -- I hesitated, but as she lay back I kneeled to the edge of the bed, and within seconds was greedily lapping up my own still hot come from her belly, starting just below her breasts to the pool that had formed in her belly button -- I gobbled it in seconds, but wanted to continue, and looking up at her, now eyes closed, and carried on -- I slowed as I got closer to her honey pt, and now the smell was beginning to intoxicate me. "Do it well" were her only words, and I slowly began to circle her pussy with my tongue -- after a few minutes, while I go up on the bed and continued my ministrations, she began to open up like a flower, and again the smell hit me, but rather than be repulsed I simply carried on with more thoughts racing, until at last I tasted the first drops of her period. To be continued -- Danielle takes me to buy some pads to share, offers me a lollipop, makes sure I know what a period is like from beginning to end, and at last, after a long hot drink, allows me to make love to her...