FIRST ENCOUNTERS
GRABBING THE RING!
THE TRUE STORY OF ELAINE'S FIRST ENCOUNTER -- how she grabbed the ring and ran!
{Sexually explicit material follows}
When I was fourteen, I regularly stayed for weekends at the home of my school friend, John. We spent our time in the normal boyish things of bike riding and chatting about music etc. For several years, I had enjoyed the pleasure of wearing a slip or night-dress of my mother's when left alone, but this was my secret and certainly not one to be shared with even a close school friend.
One weekend, John's mother was busy making a bridesmaids dress for a relative's wedding and I found myself taking a particular interest in what she was making, and was wondering how it might feel to wear such a floaty, layered dress with all its petticoats. She obviously thought my interest odd and asked why was I watching her. Obviously I denied any interest whatsoever but she could tell that I was not being totally honest and presumably thought to tease me by showing me the details of the dress so I could appreciate all its delicate layers. She explained that the dress was being made for John's cousin but that it had not been tried for size or to check how the layers hung, as she lived some distance away. I knew John's cousin was a year older than me, but about my build and I longed to have the courage to make the obvious suggestion that I model it for her, but couldn't possibly think of admitting my secret passion. Whether my interest was too obvious for me to hide, I don't know, but she suddenly held the dress against me and made the very proposal I had been too embarrassed to offer.
She suggested I should go to her bedroom to change into the dress, and she came with me to help. I stripped to my underpants and she held the dress over me and allowed it to slither down. However, the skirt was a full one and it didn't hang correctly, despite its layered construction. She explained that this dress really needed the separate petticoat, but of course she didn't expect me to put on such frilly underwear! By this time, my willingness to crossdress had been revealed, and I volunteered to wear anything she thought necessary. She realised I was actually enjoying this process, so she suggested I take off the dress and start again, not only to put on the petticoats, but also other items of underwear. She took me to her dressing table and opened the second drawer, inviting me to choose a bra, panties and suspender belt set. I had peeked in her drawer on a previous visit to the house but could hardly believe that this was for real. I was here with her - being invited to make my choice and was not sure what to select. I still had the feeling that, for the sake of my maleness, I should select the least feminine things, whilst my real desire was to indulge in as much silk, ribbons and lace as possible. Fortunately, logic took control and I realised that any pretence of maleness was ludicrous, as I contemplated wearing even the dress, let alone the lingerie, and she helped me to choose some lovely items in pale pink satin with lace trim. I was looking forward to feeling the petticoats swishing against my legs, and my first reaction was to suggest that I did not need to wear stockings, and therefore the suspenders (garters). She commented that this was nonsense and, if I preferred, I could wear tights. I admitted my anticipation of how the petticoats would feel against my legs and she was quick to re-assure me that stockings would do nothing to spoil this; indeed, their sheer finish would make the lower layers slip more easily over my legs.
I dressed with her help and was soon wearing several beautiful layers of feminine things from my panties to petticoats. She suggested I put on some makeup before finally putting on the dress, and I sat at her dressing table whilst she applied powder, lipstick and eye make up. I could hardly believe what was happening to me, and I was beginning to feel far from relaxed inside my panties. She sensed my condition and suggested I should spend a little while on my own to get used to the sensation of wearing these clothes. As she opened the door to leave me, I saw John standing outside looking at me through the open door. I had worn a slip before, sometimes even a night-dress, but always in secret, and now here I was dressed in the most gorgeous underwear and being observed my school friend. I closed the door quickly and locked it, finding my arousal now completely replaced by a feeling of enormous embarrassment. However, secrets lost are no longer secrets, and what I was doing was so delightful, that it was not long before I was undergoing the most wonderful sensations I had ever known.
John's mum returned shortly afterwards and helped me into the dress and fastened it behind me. She knew that John had seen me in my underwear and suggested he ought to have the chance to see me now fully dressed. I agreed and we walked downstairs to the lounge where I apologised to him for looking so ridiculous. He replied that I was far from ridiculous and actually looked rather pretty. His mum then left us and said she had to go to the shops, but would be back in an hour or so. As she left, she called me to one side to say that, if I wanted to, I was welcome to wear one of her night- gowns in bed that night, but to remember that I was sharing the room with John! The hour passed quickly and without any sexual contact, though John asked me a lot of questions about my clothes and how it felt to be wearing them. I admitted that they felt lovely and I was really enjoying having them on, as this was how I had always longed to dress. I began to wonder if he was envious of me and would like to try on some of the pretty things himself, but was pleased to find he had no interest in that at all! I told him of his mother's offer to lend me a night-gown for the night and asked if he minded.
His reply made it clear that he far from minded and would actually be looking forward to bedtime! His mother returned, and we spent the evening watching television, me still wearing my bridesmaid dress. I found the lace edgings of my petticoats sometimes came into view, and I had to start to learn that art of adjusting my dress to remain properly modest. John and I were both looking forward to bedtime, but were reluctant to be seen eager. Eventually his mother said she was going to bed and left us alone downstairs on the sofa. We had maintained a respectful separation between us all evening but now snuggled closer together, and John began to whisper to me how desirable I looked, like a bride on her wedding night. I couldn't help admitting that this was exactly how I felt and we went upstairs, hand in hand.
Once the bedroom door was closed we locked it behind us. I had to face the new experience of undressing from my delightful clothes with him watching me. I had thought earlier that this would be embarrassing, but when the time came, I found I was longing to be seen in my pretty underwear. I needed John's help to undo the rear fastenings of my dress. Then, I was once more as he had seen me earlier. This time there was no bolted door between us and he reached out to hold me through my silk and lace lingerie. The arousal I had experienced earlier on my own was nothing compared to this and he continued to caress me as I removed my petticoat, but kept on my bra, stockings and suspenders. I slipped a full length white silk night-dress with a chiffon overlay over my head and delighted in the feel of it slithering down to cover me before slipping on the matching chiffon and lace negligee. These things were nothing like the simple night-dresses my mother owned and I realised that these beautiful clothes were the sort I had to wear from now on.
My sexual experiences up till then had all been solo ones and now my first experience of lovemaking was to be whilst dressed as a girl. Our love making was so tender and I did my best to please him, seemingly with success, in return for the real self he was helping me to discover. It was only when we looked at the clock did we realise just how many hours we had been in bed, and so far from asleep! We finally fell asleep and I awoke the next morning to find myself still in John's arms. When we went down for breakfast, I wore a matching negligee over my nightie and the smooth layers of fabric still felt every bit as good as they had in bed! John's mum obviously realised I had "found" my true self in these feminine clothes and suggested I should wear a dress again that day. This time I had no hesitation in selecting the loveliest underwear to put on beneath a thin summer dress. It was obvious that I was extremely comfortable in the female role and John's mum suggested we go shopping to buy me some things of my own. She was very happy to buy things for me, but on condition that we made no attempt to hide that the clothes were for me. I didn't feel ready to go around town in a dress so I had to wear my boy's clothes whilst we visited the lingerie and dress departments of a large store. Although having petticoats and nighties held against me in public to judge the sizes was very embarrassing, my desire to have them was so strong it easily overcame any reservations I might have had. My stay with John was extended to a week and I spent the entire time as his girlfriend and lover. I wasn't at all worried when I realised the outline of my underwear showed through the dress and indeed, I loved it when John noticed some detail, perhaps, of my bra, slip or camisole and made a comment. I kept my new clothes at John's house and would often go round to dress, though we still tended to play the same sort of games as if I had been a boy. If we were being a bit too boisterous, I sometimes became a little immodest and John would enjoy a fine view of my lingerie and petticoats - but I didn't mind that one bit!
When we went away to university, John and I lost touch with one another, but now, away from home, I had the opportunity to be feminine much more regularly - every day in fact, but normally just alone. I have since had hundreds of enjoyable hours wearing nice dresses and petticoats and sleeping in lovely night dresses. I love to wear soft, floaty clothes whenever I can, which is now almost every day when I am alone at home, and my wife and children are out. However, that experience of spending a full week as a girl, and with a boyfriend, was one I have never been able to repeat, though I often relive it in my memories.
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