When I was given the part, I didn't know how to react. I was in an all-girl school and someone had to do it, so I guess why not me? But how would I play the part of a teenager approaching manhood when I didn't know much about guys? There had been little chance to get to know how boys carried on as I was an only child and although I had met some boys while out with girlfriends, few had impressed me to the stage where I had a real relationship. Besides, being considered a bit of a nerd, I had my school work, acting and music to keep me occupied. So I needed to do some research to play the part. I just had to succeed in this character as I always want to be the best, just as I wanted to get into the university course I desired. My school drama teacher was of little help, only saying to get to know the character and how he would react. How could I do that when I knew little of a guy's mind anyway.
I talked to the director of the playhouse near home where I had been acting since I was a child. Miss Smith was a strange woman, not overly liked by most of my friends, but I managed to get on with her. She had taught me a lot about theatre as I grew up and she was the only one I could think of talking to. She was more than obliging, even had a sparkle in her eye when I said I had to play a boy and had to give a pretty good account of myself as it meant so much for my final year results.
She was the one who suggested I literally step into the shoes of a male to experience what they went through. I was gobsmacked but she showed me how, with a little make-up and a wig, and a few costume changes it could be done. Over several weeks I learnt the stagecraft that would transform me, leading to the time when I would step out as a male for the research. Little did I realise just how it would transform my life completely.
I selected a night out at a rock concert in a nearby town to put the changes to work and used the dressing room at the theatre to get ready after Miss Smith gave the permission. The transformation involved wearing a wig over my ginger hair that I had already cut shorter and temporarily darkening my natural ginger eyebrows into a dark brown. Some padding in my shirt gave me broader shoulders and the jeans and sneakers could have been worn by any sex. I did take the extra precaution of binding my breasts by wearing a skin tight, sports compression t-shirt that flattened them perfectly. It would give me the look of having worked out, resulting in great pecs, as long as my nipples controlled themselves.
The transformation shocked me when I had one final look in the mirror. I was nothing like my former self. I was reasonably tall and long limbed for a girl as it was, but I had filled out recently without being fat, so I fitted reasonably well into the guy clothes I had borrowed and scrounged from seconds shops.
I headed to the concert where I intended to simply be an observer, watching guys and their reactions. Walking through the door and past the security was a bit scary as I expected them to frisk me, but nothing happened and I joined the throng. I didn't expect to meet any of my friends as the concert was in the next town, requiring me to drive more than an hour in my mum's car to get there.
I got into the groove of the concert and was dancing away with the massive amount of people, enjoying the silliness of the guys and their antics as they showed off to each other, not even worrying about picking up girls. It was then an older girl bumped into me, and she was right out of it. She was either drunk or high and I tried to steady her when some boof-head of a guy pushed me away and said: "Get your hands off her, she's with me." I couldn't believe the reaction by this jerk, angered by something as simple as her running into someone else and then construing I was "picking up his property." I was about to tell him off when the girl put her arms around me and gave me a passionate, if wet and sloppy kiss on the mouth. I was stunned. "I'll do what I want. You don't own me you jerk," she screamed out at the guy over my shoulder. I pushed the girl away and turned to the jerk when all of a sudden I saw him throw a punch in my
direction.
Now, I have done lots of courses at school and one of them was self defence. So being sober, I easily avoided his drunken, wild swing, which resulted in him being thrown off balance, falling to the ground with a bit of help from my outstretched leg. But before I knew what was happening security was hustling the three of us out of the venue. I was protesting my complete innocence but they were stoney faced. "Don't fuck with me mate. You are out. I don't care who started it." So there I was on the pavement with this stupid bimbo and her boyfriend who then tried to fight with security only to be quickly bundled away from us.
"Fuck, fuck, fuck, how do I get out of here now," the girl said as she staggered along the pavement. She was as I imagined a stupid blonde bimbo to be, pushing the boundaries with her short skirt and very revealing top. "He seemed so nice, then he turned stupid and clingy," she slurred. "Shit. Prick must have spiked my drink, I'm out of it." I suddenly felt sorry for her, but realising the night was wasted for me, I started to walk away. She came staggering after me, grabbing my arm, pulling me around.
"You were great. I saw it all. You dropped him. What a lump he is. He said he was going to get me home. Please help me." I turned and started walking away, not wanting to get involved. "Bastard, a girl can't trust any of you guys."
It was then I realised I was, in her eyes at least, a guy and stopped. Well, if I can't do the right thing for a fellow female in trouble what sort of person would I be. I turned and stepped towards her with my hand held out. "Come on then, where do you live? My car is around the corner," I said in my deepest voice. She smiled and leaped into my arms, again giving me a wet, passionate kiss, this time sticking in her tongue. I pushed her away. "I'll give you a lift, that's all," I said.
"Great, let's go," she said putting her arms around me. Holy shit, I thought. What is going on here. What an idiot I am by getting involved in the first place. I was supposed to be heading home, now I'm helping her out. I started walking, pulling her quickly to the car, wanting this to all end as soon as possible. She hopped in as I held the door open for her. "A real gentleman," she said smiling at me as she sank into the seat, her short dress riding up to her crotch. She caught me accidentally looking at her blue-coloured panties, spreading her legs a bit more to give me a better view as I looked away. I felt myself turning red with embarrassment and shut the door. She didn't seem to worry much about it and gave me directions without trying anything else. Luckily I vaguely knew the way and we safely arrived at her place.
I helped her out of the car, putting my arm around her waist and struggling with her to the front door as she leant against me. She couldn't use the key so I grabbed her hand and held it in the lock. The door opened and we fell inside. It was a beautifully-kept small apartment, very feminine and certainly not what I was expecting. I asked her where the bedroom was and helped her until I was able to flop her onto the bed. She lay there all arms and legs, with her dress riding over her hips and the top askew exposing her lace covered breasts. I turned to go, glad I had at least got her safely home. She grabbed my arm suddenly and pulled me down. I landed on top of her.
"Please don't go, every guy I have been with has treated me like shit and would have been jumping me by now. Not you. What are you gay or something?"
"Of course not," I said not wanting to expose myself and be caught out. "I just don't want to take advantage of you like this. It's not right."
"Oh you are just so different, aren't you," she said. "Where have you been all my life? Please, just stay." She began gently running her fingers over my face, then playing with my hair, wig. "Wow, you have had a really close shave, like a baby's bum," she laughed.
I smiled at that, thinking if she only knew what was before her. Before I realised what was happening, she kissed me, a soft gentle embrace, nothing like the sloppy drunken mash from earlier. I tried to pull away, but I was pulled in, entranced by my situation as the closeness and the heat generated by our two bodies started to arouse me. I was a girl, acting as a guy with a girl who wanted me. Wow.
Before I knew it I was responding to her kiss, my tongue playing with hers. I started to enjoy it, enjoy her. Her smell, her touch, her softness. I was really turned on by the situation, feeling moist between my legs. She grabbed my hand and led it to her breast. I tried to fight her but I had lost control of the situation as, I must admit, I really didn't know what to do. Expose myself, as a girl of course, or just try and escape somehow.
I was really starting to enjoy kissing this girl, I had become somebody I never knew existed. I had never, ever, thought of being attracted sexually to a woman, only admiring beautiful girls from afar, as any girl would do. But this was taking me to places I never realised existed.
With that thought I suddenly felt a chill pass through my body. The message it carried was get out of there now. I was kissing a girl, a woman obviously older than me, at least in her 20s, but something kept me there in the embrace. I should walk out on her knowing I would never see her again and everything would return to normal. She wouldn't remember me as she was so high on whatever had been forced on her. But I stayed. I wanted the abnormal in my life all of a sudden. I wanted this. My fingers worked their way past the lovely, lacy bra, enjoying its soft satin feel until I started playing with her erect nipple.
"Your bra is so lovely. I haven't seen one so nice," I said as she pushed my head down and I started kissing her velvety soft skin.Â
"Funny thing for a guy to notice. You guys just normally want a look then take it off."
"No, I really like it, the blue suits you," I said lifting my head.
"You've already seen what else I have," she said, smiling in a wicked way. I began kissing her between her breasts as she had moved my hand down her body to the waist of her panties. The soft material gave way to the ever so gentle covering of hair leading to her vagina where her wetness covered my finger. She moaned and forced her mound up to meet the pressure I applied and I was lost. I should get out of here, I thought, but she opened her eyes and looked at me with such lust. "Oh that is wonderful, please, please ..."
My fingers moved as they had done the night before in my own pussy. I found her nub, gently caressing it and this sent her over the edge, as she moaned louder in total enjoyment. So I continued, playing with her, running my fingers along her opening, and coming back again to the hard clit, gradually entering her until she came with such a rush my hand was absolutely covered in her cum.
"Oh my sweet, oh that is so wonderful. You are great." She pulled my cum-covered hand to her mouth, licking it then offering it to me. My tongue had a mind of its own and started tentatively at first licking her sweet tasting nectar. We kissed and I was lost in a whirlpool of emotions, sinking so deep into woman love that I didn't know how to escape. She started working her way to my pants undoing them.
"Here let me get you off," she said in a rasping voice. I was about to let her reach inside my pants as I desperately needed a release, oh how I needed it. But I grabbed her hand pulling it back. "I would rather please you more," I said.
"OK," she said a little too quickly as she pushed my head down past her breast to her hips, my tongue leaving a trail all the way, tasting her salt-sweatened skin. I reached her blue bikini panties, obviously part of a set with the bra I had spied earlier in the night. "You were right, I love these, they're so lovely, but..." I said as I grabbed either side and pulled them off as she raised her legs. She then spread her legs before me, revealing her pussy, glistening through the light covering of hair that was now inches from my mouth.
I didn't mean this. I intended to again have used my fingers to get her off and to get out of there. I tried very hard to pull away but she put her hand forcefully on my head: "Please, make me cum, lick me to heaven." Her smell was overpowering. I had already tasted her and enjoyed it like a drug and now her pussy was in front of me, the lips oozing in anticipation.
Thoughts of damnation were screaming through my head as my tongue again took over, my first tentative attempts gently licking her sweet, soft lips. She moaned again, rising her hips to meet my lips and I immediately kissed the soft folds, sucking her, wiggling my tongue against her nub which stood out like a sentinel. She started to writhe like an out of control beast under me and I worked harder, my tongue flicking in and out, up and down.
Oh how I was enjoying this. I didn't care that what I was doing was wrong, against everything I had been brought up to believe in. I had walked over the threshold into woman love and was enjoying every minute, except I wanted to cum as well. With one last scream she came and her juices again flowed freely as I licked then drank every drop. She just lay there as I moved back up to face her, her eyes closed with the complete look of satisfaction that I had produced. She opened her eyes and I realised l was in love, as our mouths joined, our tongues flicking and playing, swapping the juices I had just lapped up.
"What's your name?" she asked. I was stunned. We had just shared one of life's most intimate moments and we didn't know who we were. "Jen," I dreamily said, then realising my error quickly said, "Ben, Ben Smith." "Hi Ben, I'm Steph," she said smiling. "You are the best. I have never cum so much. Most guys don't want to go down on me. They want me to do it to them though."
We cuddled and she started feeling me, working her hands over my back to my arse, then towards my crotch. Though I loved it and wanted more, I realised I couldn't let it happen. "I really have to go. My folks will be expecting me." She laughed. "Are you still living at home?" I wanted to say, of course yes, I am a girl in my last year at high school and heading to university next year. "Of course I am living at home. Saves money," I said extricating myself from her clutches.
"I want to see you again," she said and before I had a chance she grabbed my mobile, that had fallen from my trousers, entering her number. She then pressed dial and it called her phone which she picked up. "Now we have our numbers," she said. She kissed me and I responded with such intense love that I didn't realise I could ever feel. In the car I lowered my pants and brought myself off. It didn't take long, I was so fucking horny.
I should have deleted the phone number then and there. My life had been turned upside down and I should have stopped it from getting worse. I now looked at my close circle of girl friends through different eyes. Even at the other girls at my school. I was sure I was not interested in them sexually, but appreciated their bodies a lot more. One friend caught me looking at her a bit longer than usual, throwing me a questioning look which I smiled at. I got through my theatrical performance, giving the leading lady a big surprise when we had to kiss. Instead of the expected hesitant coupling that had been happening before at rehearsals, I grabbed her shoulders with both hands and planted my lips on hers with fervour. She was a bit taken back, but like a true actor she carried on and we received good applause for our efforts. I was given great compliments for the way I had responded to playing the young man's character. But I was troubled and within days
had to sit the first of the practice exams before the real tests the next month. Expecting to pass with flying colours, I just managed to scrape through, my mind that had been so focussed and never let me down, was elsewhere.
Steph rang several times, leaving messages for me to ring her but I didn't. Then one day she caught me and I stupidly agreed to see her again. We made a date at a club. I intended to let her down, tell her I was not interested in her so I dressed as a guy again. Meeting her at night was good as it helped with the disguise. We met hesitantly, I kissed her cheek and we went in, ordered some drinks and started to chat. My intention of dropping her was lost as the time flew by. We had so much in common as I quickly found out and then we danced, not too close but responding sensuously to each other. It was late when we left and I really had to get home for sleep because of study. She talked me into driving her back to her place. We stopped outside and turned to each other. I thought now is the time, tell her and end this, but when I looked into her eyes I hesitated and before I knew it she was kissing me.
We made it into her apartment, kissing each other, struggling to her bedroom running our hands over each other's body. I was so high on lust I bent down and lifted her up, carrying her the last metre to the bed. Luckily she was lighter than what I imagined, and we flopped down onto the bed laughing like crazy people. I kissed her lips then moved to her neck, working my way to her breasts. I undid the buttons on her shirt, lifting it away revealing a red lacy bra, even fancier than her blue number. "Wow, you have great underwear. It is so lovely," I blurted out as I rubbed my face into the bra pushing it aside with my chin to find her nipple. "There is more to come," she giggled. There was no stopping me this time as I sucked on each nipple, Steph moaned enjoying every bit. I then kissed my way down to her jeans, stopping as I looked back at her and she had this wicked look on her face. I undid them pulling them off as she raised her butt off
the bed revealing red panties, a match to the bra. I had never thought much about lingerie, never being able to afford it but it was so lovely that I exclaimed, "Oh Steph, these are just so lovely," as my mouth sucked on them over the wet spot made by the juices from her pussy. The reaction was immediate as she bucked, thrusting her hips up so I sucked again, drawing her lips into the soft material.
She played with my hair and my hands reached up and played with her breasts, squeezing her nipples as I continued sucking her and the panties. She moaned and bucked as I pushed by mouth, chin, everything against her, and then the flood started. She came with wild enthusiasm, squeezing her legs against my head, but I refused to stop. I didn't need to finger myself, I came just after her, the tightness of my clothes and the enjoyment I had in pleasing her sending me over the edge.
We lay beside one another exhausted. All of a sudden I realised she had worked her way down my body and was starting to undo my trousers. I immediately came out of my reverie, sitting up and grabbing her pulling her back to up to me. "What are you doing? It's your turn to cum," she said.
If she only knew. "I can't," I said. "I really have to go."
"No, no way, not after what you did to me. That was just so wonderful."
I pushed her gently to the side as I stood up, looking back on the disappointment shown on her face. I leant over and kissed her, then grabbed my things and left before anything more happened. I had failed in my quest to be honest with her. I just couldn't bear to let her down.
My school work was suffering so much, even my parents realised that something was wrong. I was just not concentrating, so I decided I had to sort it out or the year would be gone and my aspirations for university lost. I would front Steph at her work, she had told me where when we were having our drinks. The only way I could find the time was after school, so dressed in my school uniform and with no disguising make-up or wig, I would somehow tell her Ben could no longer see her or was no longer around. With that in mind I went to the store and was wandering around looking at the lingerie when she approached me. "Can I help you miss?" she said. I turned to her looking into her lovely eyes but couldn't say a word, lost in her beauty. "I, I'm looking for some matching set lingerie, similar to that a friend wears. She has these lovely blue and red sets." Whether she thought I couldn't pay for them or somehow thought she recognised me and was
trying to figure out where it had been she saw me, she hesitated a bit. "We have some nice sets over here," she said wandering away. I followed her, realising I had little money in my account to pay for anything if I bought it.
We looked through the lingerie as I recognised a similar set to the what she had worn, fingering them thoughtfully, "You can try on the bras, but not the panties, as they should be regular sizes. Try these, they should fit you. There are changing rooms over there. What's your name?" she said pointing to rooms at the rear of the store. "Ahh, J..Jen," I managed to get out. I didn't know what to do. I went inside, removing my school shirt and old white cotton bra, slipping on the lacy, red bra first.
I was thinking it did look nice on me and the right size when there was a knock and she asked: "Can I come in, perhaps I can help."
Before I knew it Steph was in the cubicle with me, looking me over. "Looks lovely on you. I have a set exactly like this," she said. I went cold. Had she recognised me? She put her fingers on the bra, pulling the sides so they fit tighter, then she touched my breasts. "Sorry about that. But you have probably been wanting me to do that for some time," she said looking me in the eyes. "Are you sure your name is Jen. Not Ben as well is it?" I was busted, but how?
"I'm so sorry. How did you know? I couldn't find a way to tell you."
"I realised your face was too soft the other night. Then you had to race away again before I could touch you. Then there is one other major thing. You have a little mole where your adams apple should be, as a guy would have. What is going on?"
I was dumbfounded not sure what to do when I realised she still had her hands on my breasts and was fingering my nipples. I weakened at the knees. "So how old are you then?"
I swayed as I melted under the enjoyment of her touch. I told her and said I was in my last year at high school, then explained about pretending to be a boy for the play and how things got carried away.
"Well you were pretty convincing, I can tell you. You had me coming," she laughed. I relaxed, realising I was not in that a bad situation, but perhaps in something I might end up enjoying.
"We need to get together and have a talk. What are you doing tonight?"
"I, I can't. I have a really important exam tomorrow. How about Friday?"
We set the time at her place and she let my breasts go and left, pausing to say loudly as she left the cubicle, "That colour really suits you miss."
I took the lingerie to the register where she asked, "Have you enough to pay for this?" I shook my head no. "Well when you come on Friday I will tell you how you can earn enough to buy it and more."
She took the bra and panties from me and placed them in a nearby trolley.
I couldn't believe what was happening. Here I was, a normal girl without a worry in the world, heading for a planned career and life, when all of a sudden everything had been flipped upside down by this gorgeous woman.
I don't know why, but I was a little more settled at school for the rest of the week getting through my work, but I still couldn't get Steph out of my mind and our planned meeting. Friday came and I found an excuse to stay overnight at a schoolfriend's house and went to her house. I don't know what overcame me but I put on make-up for the first time in ages, and was wearing the newest undies I could find, hoping I wouldn't be having them on for too long. She answered the door in a slinky one-piece catsuit leaving little to the imagination as her nipple poked through the material that clung tightly to her body. I hesitated and my jaw must have dropped. "Stop drooling and get in here," she said. Before the door had shut she grabbed my arm, pulling me to her. "Well lover, I didn't expect you to be a fiery redhead but it probably answers how you turned me on so much."
We kissed passionately, our tongues gently playing and our hands moving ever so gently over each other, I thought I would come straight away.
"Now enough of that," she said breathing heavily as she forced herself from me. "We need to talk. I have a proposition for you." We sat and Steph explained how she was always interested in other women, but had never found the right one, until perhaps now? She said the night at the concert she was picked up by the guy who was friendly enough and must have spiked her drink, hence her willingness to end up wanting to have sex with me.
Although she worked in a store, she also did some freelance modeling and working for a lingerie company that sold its goods through home parties.
She talked to me about the women's groups she had in mind, all older lesbians or bi-sexuals who met regularly for fun, and she wanted me to join her - dressed as a guy.
"What do you mean, I would have to be a guy. Everyone would know anyway if you ended up picking it."
"That's all part of it you see. The women I plan to introduce you to would enjoy the novelty of a girl dressed as a guy and it will lift our sales. You will be a hit, believe me. And there's a lot of commission for us both on sales. After all, you are such a lovely guy," she laughed.
Well I was surprised to say the least. This was one thing I didn't expect.
"But you are so beautiful. I'm just ordinary. I would mess it up. Besides, I have my exams to worry about." She reached over, took my face in her hands and kissed me, oh so tenderly. "You, my love, are beautiful and such a sexually charged chick that you will be a hit. These women we will meet will see that, I'm sure of it. They too will love you. Just remember we'll be together. Besides, we will start after your exams so you will be ready to take on the world."
A thrill went through me when she said we would be together and any thoughts I had that our relationship was wrong were forgotten.
The zipper on her catsuit was hard to find but I helped her peel it off, revealing her wonderful boobs. I latched onto her nipples straight away first one side then the other. She told me to slow down, but I couldn't I was relentless.
I don't know why I worried about my fresh panties, as they were gone in seconds and she was there greeting my pussy for the first time.
She then gave me an orgasm I had never even dreamed about, using her tongue with such great effect I thought there would be no end to it. Then she attacked my other love hole, sending me around the world all over again.
Needless to say I stayed that night and our lovemaking took me to another dimension in my life.
My exams were barely over when we organised our first party. We worked on a routine where I was to be the waiter handing out drinks and nibbles before the show began. Then I would disappear coming out after Steph had run through several outfits and she would strip me to reveal another set of underwear.
The party went perfectly, with my disguise working well enough though I had never run into such an aggressive pack of women before. I am sure several women knew I was a girl, sidling up to me in a suggestive manner, with one actually pinching my bottom. Of course I smiled and spoke to them as if they were children, "Naughty, naughty, I will have to smack you if you do that again." Of course most did try and I had to smack their hands. My striptease was a hit as my body was revealed. Steph kissed me and ran her hands all over my body, taking clothes off as she did. It was very, very sexy, even from my perspective and my panties were the worse for wear. But by then I was not worried and just went along with the fun as the women cheered as each piece of clothing revealed more body and lingerie.
We made a killing with sales, as most of the lingerie was sensible briefs and bikinis wanted by the older women and very lovely lacy bras of course. We were talking to the party organiser and she wanted us to do our show on a regular basis, and was even prepared to cover costs if there were not enough sales. She loved the fact I was so young. I was explaining I was aiming for university hoping to get into law when she said "Say no more. If you are equally as good at your studies as you are thinking up a show like this I want you on my team." She offered me work immediately as a clerk at the law firm where she was a partner. "My dear, I can see we are going to have a great relationship together," she said, putting her hands around me and kissing both my cheeks. She didn't let go before a feel of my arse. I didn't know what to think, but if I could control her urges, my life was certainly on the up.
I told Steph and she laughed, "She is sex madd. You will need your wits about you."
"With you as my partner, I won't have any problems," I said.
I hope those who emailed me after my first story enjoy this.
Copyright 2012 pixiekim5@yahoo.com