I was coming up for 17, and a very good looking crossdresser. Clothes looked good on me, being 5' 6, slim and hairless. shaving all over every day. Dad had walked out when I was 7, and since then I'd been allowed to dress up in my mummies clothes. It wasn't that she didn't mind, she encouraged me. If I had PE at school that day, I'd wear boys clothes, but if I didn't, she'd find some navy blue gym knickers and long white socks for me to wear under my "Normal" clothes. Once back home, I was allowed to pick some clothes of hers to wear around the house, and at bedtime I wear a full-length petticoat as a nightie, with nylon panties underneath. By the time I was 11 or 12, my mothers clothes fitted me beautifully, and I looked good in a mini-skirt, stockings, 3 inch heels, see-through blouse and a padded bra.
By now mummy was teaching me the art of make-up, and we'd often sit on the settee together in the evening, talking about boys and men. She freely admitted that she had no interest in men anymore, preferring her vibrators and the company of "Auntie Joan", her longterm weekend guest. Both mummy and Auntie Joan tried to make me look as feminine as possible. My hair had been allowed to grow long, and they'd sit me down, one doing my hair and the other my make-up. It felt lovely, and I'd quickly get a hard-on. Neither seemd to mind me going to my room now and again to have a wank, and Auntie Joan sometimes brought me magazines showing young boys with men, or ladyboys with men. I got really excited looking at the ladyboys, in their sexy underwear, servicing their men. That christmas I got a selection of vibrators from a small slim one up to a beautiful pink cock-shaped one, and some KY jelly. Mummy didn't know that I had been using hers secretly for years. It wasn't long before I was easing the nice big pink one slowly up my boy-hole, as I lay alone in bed, wishing it was a real one.
On my 13th birthday, mummy took me out for a ride in her car. As usual I was dressed as a tart, in her clothes, skirt up at my stocking tops, and blouse undone to show off my padded bra. She said I had to wear sunglasses, and then I could see how many men were going to look in at me. Wow, every time we stopped at traffic lights, men would look at me, at my legs and my false boobs. "Open those legs more" mummy would say, "and smile at them" I did. "Look at the bulge in those trousers" she'd say "Wouldn't you like to get that out and play with it?" I couldn't help it, I just blurted out "Oh Yes.....Yes" Back at home I opened my cards, some were boring boys stuff, but mummies said "To my lovely daughter Janet" and Auntie Joans said "Lots of love to Janet, who now needs a boyfriend" I knew that Auntie Joan had a friend, a chubby middle aged man called Jim. Mummy and her had talked of him often, saying he was queer but harmless, and that he liked little boys. One evening, sitting on the sofs, Autie Joan had her arm around me, talikng about her friend Jim. Mummy was out, and Joan slid her hand up under my skirt, and began to fondle the front of my panties, saying that Jim would love to get to know me, and how I'd make a perfect "Girlfriend" for him. Soon her hand was inside my panties, slowly wanking me, and she was suggesting that we invite Jim for dinner, so that he could meet me. Oh, the idea was growing on me, and soon I was spurting my boy-cum all aver Auntie Joans hand. "Good" she said as she wiped her hand clean on my skirt "I'll invite him on Friday, about 7.00pm, that'll give you time to bath and change"
Friday soon came, and as sson as I got out of the bath, mummy and Auntie Joan were deciding what I should wear. It was to be a high necked see-through white blouse, black padded bra, wrap-around pleated skirt, stockings, 4 inch heels and a hair do that they were seeing to. The door bell went, it was 7.00. All I had to do was put on some jewlery, but mummy insisted I wear a big bold pearl necklace. I didn't like it, but also didn't know what it stood for. Mummy went downstairs and let him in. I heard them talking, her saying how beautiful Janet was looking tonight, and how he'd love being with her. Just then Autie Joan and I appeared at the top of the stairs. Joans skirt was so short, Jim could clearly see her panties, and I saw him looking. I took 2 steps down, then pretended to forget something, turned and ran up to my room, giving Jim a good look at my black thong, disappearing between the cheeks of my bottom. Minutes later I was coming down the stairs, and Jims eyes were only on me. At the bottom, mummy and Auntie Joan kissed Jim on the lips and them introduced me. "Go on" said Mummy "Give Jim a kiss" I lifted my head slightly, as Jim was a bit taller than me, and gave him a little kiss on the cheek. "No that wont do at all" said Mummy "Go on Jim, give her a proper kiss, we wont look" I turned to see Mummy and Auntie Joan having a long kiss, as they often did on the sofa in front of me. Suddenly I
felt strong arms around me, as Jim pulled me to him. I looked up to see his lips coming towards me. Oh, bristly lips, so rough, then his tongue, probing. A hand eased up the back of my skirt and fondled my bottom. "That's it Janet, do as Mummy says, and let Jim have a proper kiss" I parted my lips, Jims tongue explored my mouth. The kiss went on for some time. "Save a bit for later" I heard my Mummy say. I stood back, feeling so embarrassed, looking at the floor.
"Let's go into the lounge and sit down" Joan said. Jim took hold of my hand and began to lead me along the hall. It felt nice and feminine to be led by a man, so I followed in my nicest sissy walk. There were two sofas in the lounge. "You two sit together on that sofa" Mummy said, pointing to the one near the fireplace. I sat as dainty as I could next to him, as Mummy and Joan sat together opposite us. "Doesn't Janet look lovely" said Auntie Joan "She's so pretty and very feminine, don't you think?" "Oh Yes" said Jim "you really are gorgeous" as he looked me in the eyes. "Give her a cuddle Jim, go on put your arm around her"said Joan. Jim put his arm around my shoulders and pulled me towards him. I put my hand out to steady myself, but it landed on Jims thigh. It surprised me a little, so I just left it there. "OH look Joan" said Mummy "Janet looks like shes about to get Jims cock out. Do you want to Janet, do you" I was shocked ans surprised. "There,
there Janet" said Jim "we're ok as we are arn't we?" I nodded. "Give me a kiss then" he said. I lifted my head, his bristly lips found mine and his tongue felt like an old friend.
Jim and I spent the next few minutes kissing as Mummy and Joan whispered about us. "Why don't you sit in Jims knee at the table, while I dish up" said Joan. Mummy and Joan went into the kitchen, while Jim selected an upright chair and sat down at the table. I sat sideways on his lap and felt his arm slide around me , holding me safely. I looked up, and Jim kissed me again. I felt his hand slide up under my skirt, and as I parted my lips, I opened my legs to give him more room. As his tongue flicked into my mouth, his hand fondled the front of my thong. Between kisses Jim whispered lovely things like. "Oh you really are lovely. I'd love you to be my girlfriend, and make love to you". Then "Why dont you stand up and slip your thong off?" I quickly looked around, Mummy and Joan were in the kitchen, so I stood up beside him and lifted my skirt right up. In seconds he had tugged it down to my ankles, and as I stepped out of it he whispered" Come and sit astride me, facing me.........please"
I lifted a leg over him and sat down over his zip, putting both my arms around his neck and pulling myself up for more kissing. Again I felt my skirt being lifted and his hands on my little cock. "Don't mind us" I heard as dishes were being put on the table. Using one hand I reached down and began to tug at Jims zip. "OK we can see you need help" said Mummy. I opened my eyes. Stand up a minute Janet and move to one side. I obeyed and watched as he stood up and they unfastened his trousers. They fell to the floor and I saw his bulging Y fronts for the first time. In one movement they pulled them straight down to his knees. Thats when I saw Jims cock for the first time, a purple helmet, but just like my pink vibrator. I longed to touch it.
"Now sit down as you were before, and have fun" whispered Mummy as she slapped my bare bottom. Jim sat down and I sat astride him. Oh feelling his bare thighs on my bottom cheeks was lovely. I looked down and saw his cock pointing up at me, with that big purple helmet. I reached down and took hold of it. I heard Jim sigh softly as I began to wank him. We began to kiss. That's when I heard Mummy call Joan. "Come and have a look Joan, I think they're in love. We just kissed and wanked, then Joan whispered "Remember where your pink vibrator goes?" I nodded "Lift your bottom a little" I heard. I lfted my bottom a few inches and suddenly I fely very cold jelly being spread between my cheeks, a finger teasing my boy-hole and my mummy saying "This is where Jims cock belongs darling, you lift a little more and mummy will guide it to you." I lifted a fraction more and felt Jims helmet sliding along my bottom cleavage ..........until...Oh it touched my
entrance. I looked down, I could see mummies fingers around Jims cock, wanking him and holding him in place.
"Now darling, gently lower yourself onto Jims cock, nice and slowly. That's it a bit more." A brief flash of pain as my boy-hole gives way, the. "That's it...Oh...Yes.. all the way down. Come and look at this Joan, Janet has a man up her". I could feel Jims soft curly hair on my bottom cheeks. His kisses were non-stop. "Now ride up and down on his Cock darling, until ...oh..he CUMS deep inside you,.then you are a Woman"
I put my feet on the ground and began to raise myself up...oh what a wonderful feeling, then firmly down, oh heaven. We stopped our kissing to watch. Up again, then down. Waves of feminie emossions were flooding over me. Jim was moaning and sighing, Joan had found the camera and was taking lots of close-ups.In a moment I had a good loving rythm going, up and down, up and down. At the end of the downstroke, I could feel Jims lovely helmet deep inside me, where it belonged. Minutes later Jim began to jerk and thrust upwards. I looked up, his eyes were closed, his head was back. Then 3 or 4 big slapping sounds as his hips hit my bottom, then "I'm CUMING" His lips were thrust to mine and I knew his loving semen was spurting into me. As he subsided, I lifted my legs and wrapped them around the back of his chair. Slowly rocking to and fro, I could clearly feel his stiffness inside me. We looked around at Mummy and Joan. They were standing each side of us. Mummy pushed her head between us and placed her lips on my. I felt her mouth open, then her tongue. After a long kiss I heard Joan whisper "If you slowly get off, we may see a trickle of cum ouze out of your pussy, there it is" she cried as I slid off the end of his cock.
Jim went upstairs for a shower, I put my thong back on and we eventually sat down to dinner.
At about 9.00 Mummy said it was bedtime, and told me to go upstairs and put my new nightie on. I couldn't wait and rushed up to change. The nightie only just covered my bottom and was transparent, with matching transparent knickers. It was high necked and long sleeved with lots of frilly bits. As I got back into the lounge, I saw Mummy and Joan down to their underwear, kissing and cuddling, with Jim in just just y-fronts watching them with his hand down inside them, playing with himself.
I sat beside him and pulled his face away and kissed him, Oh I felt his tongue and knew he was still mine. "Come on Janet" I heard "Pull his pants down and suck your boyfriend off. Come on, we want to watch"
End of part one