Another ‘first time’ lesbian story – it takes a while to set the scene, so if you like to get straight into the action, this story may not be the best for you. Any resemblance to real persons or places is coincidental.
copyright: Lesley Tara, 2009
I grew up in a medium-sized resort town on the English coast. Every summer, the local theatre would put on a show during the holiday season, with the lead roles taken by an actor and an actress who were familiar faces from television – not famous stars, as we were not big enough to afford them, but those making a name for themselves or second-rank celebrities. In the summer before my sixteenth birthday, they decided to do ‘The Sound of Music’, an ever-popular family favourite. Either to save money or as a publicity stunt, the production company advertised for local schoolchildren to audition for the parts of the younger Von Trapp children. Those successful would be paid a modest amount, and more importantly the experience would help if they had ambitions to go into acting as a career.
Encouraged by my family and friends, I decided to have a go. Although there were dozens at the first auditions, I won through and was picked for the part of the second-oldest daughter. In a way it was not a great surprise, for I had a good strong singing voice, and I looked just right for the role. Although it was only a few weeks until I would be sixteen, my appearance was closer to a fourteen year old: I was only five foot four inches tall, and had a slight figure, boyish with slim hips; my breasts were nice, but a bit below the average size for my age. Most of all, I had a youthful and innocent face, and my long, straight blonde hair was suitably Germanic. The part itself was easy enough: I had only a few lines of dialogue of my own and no solo songs, so it was mainly being on stage with the others and joining in the choruses. Because I was not yet sixteen, there were legal limits on how long I could work, and so I shared the role with another girl, each of us doing alternate days.
On most days, there were two shows: an afternoon matinee and an evening performance. I had become friendly with the leading actress who was playing Maria, and the pattern developed that I would pass the couple of hours between shows in her dressing room, chatting idly or sometimes listening to records or the radio. As she is still a well-known television actress, I won’t give her real name: let’s call her Felicity. At that time, she had recently come to public notice in a popular drama series, and she had a really powerful clear singing voice. She was then still quite young, maybe twenty-two or twenty-three. She had brown hair which had been dyed blonde and cut fairly short for the part of Maria, who starts out as a convent girl. Felicity was tall and slim, but with a generous bust for her build. She was fun and interesting, and treated me sort of like a kid sister – there was no arrogance or superiority about her at all, and she clearly found it relaxing just to be ‘girls together’ with me; for that reason, she politely discouraged any of the other actors or crew from joining us, which wasn’t too awkward as her dressing room was quite tiny.
We talked of all sorts of things – her family and mine, and our ambitions, hopes and fears. Once I asked if she had a boyfriend and she shook her head; no, there just wasn’t time – she daren’t turn down acting jobs now they were starting to be offered, and her hours of work were so strange as well. Slightly sadly, she said that relationships didn’t tend to stand the strain, but then she brightened, saying that however there were compensations – though she didn’t explain what that meant. She enquired about my ‘love life’, and it was a thrill to hear an adult call it that, even if it was basically non-existent – at least she assumed that I might be having one! But I replied honestly that I had no boyfriend, had never had one, and frankly didn’t think that I was missing much, going by my friends’ experiences. She gave me one of her warm vivacious smiles, and asked if I had a girlfriend then. I felt a bit strange with that question; I wasn’t sure what she really meant, or if she was just ribbing me, so I decided not to rise to it and just replied that, of course, I had several female friends, we did quite a lot of things together, and so on. Felicity may have sensed my awkwardness – she was very attuned to people, one reason for her acting success – as she changed direction a bit. ‘You must have someone you admire’, she said, ‘someone you know personally, I mean, not a pop star or anything like that.’
And so, perhaps in reaction to the unsettling moment just before, I told her all about Miss Henderson, my wonderful English Literature teacher. I must have gushed on enthusiastically for quite a while, but Felicity was content to listen with a slight smile on her face. Miss Henderson had only been at our school for four years, and I knew that it was her first teaching job since completing her training, which put her age around twenty-six. I thought she was so good-looking: she had lovely auburn hair that fell in waves below her shoulders (although generally she kept it pinned up), together with her bright greenish eyes and round pretty face. She had a nice figure, with a high bust that was more prominent when you saw her in profile, and shapely legs. Miss Henderson always wore neat and tasteful skirts and dresses in warm bright colours, and in winter she had tooled brown or sheer black leather boots. I don’t think I had ever seen her in trousers, and her skirt length rose and fell with the seasons, getting quite short in the summer, but she never looked less than professional. Her favourite combination was a calf-length red skirt with a bright green woollen turtle-neck jumper; the latter was quite tight and figure-hugging, and it was cinched around the waist with a wide tan-coloured belt. I waxed lyrical about the way she dressed, her lively personality, her good humour, her patience and helpfulness with awkward or struggling students, her command of her subject, and so on, as Felicity regarded me with a mixture of interest, amusement and understanding. ‘She sounds lovely’, she said, slightly wistfully, as I finally ran down, the gush of my admiration slowing to a trickle in my embarrassed realisation that I had let myself go – indeed, had said things I had never said aloud before, and even barely thought. ‘Oh, yes,’ I responded, ‘she’s brilliant!’ ‘Well,’ said Felicity, patting me on the knee, ‘I think you’ve got quite a crush on her.’ I hadn’t exactly put it that way to myself, but of course she was quite right.
A couple of days later, after we had taken our curtain calls for the matinee, Felicity and I trotted down to her dressing room, chatting amiably. We hung up our costumes, Felicity donning a silk kimono over her underwear, whilst I put back on my short summer skirt and short-sleeve top. Then we cleaned off our make-up – another nice thing was that we always helped each other with this chore, once she had shown me the correct way to do it – and I settled down on the couch. Felicity sat in the chair in front of her dressing table and mirror, and winced as she rubbed around the back of her neck. ‘I’m really stiff’, she said, ‘I must have slept in a funny position last night’, and then she gave a suppressed snort, as if saying that brought back a memory. ‘This won’t do – I’ll be locked rigid by the evening show, and it’ll affect my voice. Sally, will you do me a favour?’ she asked: ‘give me a massage to loosen me up.’ I was a bit doubtful – not because I didn’t want to help my new friend, but because I had no idea how to do a massage. When I explained this, Felicity laughed and dismissed the problem; a firm and steady rub was all that was needed, she assured me.
She slipped off her pretty kimono wrap, and came and sat on the end of the couch, with her back to me. I knelt behind her, placing a hand on each shoulder, and started to squeeze and rub them, using a circular motion towards her spine and back again. She gave a pleased sigh, slightly tossing her head, and told me that I was doing great. Felicity was only wearing some quite skimpy pink panties and a matching bra which was low cut at the front. As I knelt close behind her back, I couldn’t avoid looking downwards into it, and I could see almost all of her good-sized breasts, including the tops of her nipples. As I rubbed her shoulders and back, the bra straps and clasp kept getting in the way – I was having to move around them awkwardly all the time. So it didn’t seem at all odd when Felicity asked me to undo and get rid of it; after that, I really started to get into this massage thing, and began to feel that I was getting pretty good at it. I rubbed each side of her back with firm corkscrew motions, starting with a large circle and working in to the centre of the shoulder blade. This alternated with running my fingernails across the top of her shoulders and then all the way down her spine to the top of her panties. I was enjoying the feel of her warm skin under my touch, and she certainly seemed to like what I was doing, as from time to time she slightly squirmed and gave little grunts of approval.
It was quite sweaty doing this energetic massage on a summer day, down in the poorly-ventilated dressing room. Felicity remarked that she felt a bit embarrassed to be nearly nude when I had all my clothes on, and she urged me to get more comfortable and strip down to my underwear. She also asked me to lock the door, as ‘we don’t want someone barging in, just when I’m starting to feel relaxed.’ I hesitated only a second before complying, as it seemed obviously sensible and more comfortable in the circumstances. I quickly turned the key in the lock, and shed my skirt and top. This left me wearing a white bra (one of my favourites, with a lace-effect edging around the skimpy cups) and a matching pair of brief cotton panties, plus I still had on the white socks that were part of my costume, which came up to just below the knee.
Felicity began to direct my motions to the places where she felt most stiff, and these included on her sides and a bit around to her front as well, so that I was sometimes touching the sides of her breasts. After a while, she said lazily ‘time to do the other side’, and changed position to lie on her back along the couch. I had stood up whilst she did this, and wasn’t sure where now to sit – but she gestured to me to climb on to the couch and sit astride her. I settled with my knees beside her hips, straddling her. It was both strange and somehow exciting to feel a woman’s warm body between my spread thighs, as my buttocks rested just above her knees Felicity looked at me for a few seconds through half-closed eyes, and then she quietly asked me to massage her front. At first I wasn’t sure what she meant and I rubbed gently across her stomach, above the panties, but she caught my gaze with her own and breathed softly: ‘not there, my sweet, higher – do it higher.’ I felt a fluttering of nervousness and excitement in my stomach, but I was caught up in the intimacy of the moment and slowly I worked my hands upwards. At first I tentatively did a circular massage around each of her breasts without really touching them, as she lay quite still with her eyes closed and her mouth slightly open. ‘Closer,’ she whispered, and with sudden boldness I began to stroke and rub her breasts, right up to the nipples – which were already erect. Felicity suddenly opened her eyes and looked at me directly. ‘I bet you’d like to be doing this to Miss Henderson,’ she said with a mischievous grin. I realised with a shock that indeed I would, and I felt a strange warmth and dampness in my pussy.
As I stroked Felicity’s breasts more firmly and with growing confidence, she arched her back and told me how good it was making her feel. Then she said that she wanted to see mine, and before I could think what to say she reached up and unfastened my bra, and it fell away into her hands. Somehow I knew that a crucial line had been crossed, that this was no longer a friendly massage but a sexual seduction, and that things would in future never be the same again. I felt a bit embarrassed as she gazed at my budding breasts, and said something about them being rather small. ‘No, they’re perfect’, she countered, and she took one in each hand, cupping and stroking it. The effect was amazing, creating a tingling sensation which ran all through me, making me feel intensely alive and sensitive. Then Felicity said, ‘I bet you wish Miss Henderson was doing this to you!’, and I gave a kind of broken moan at the thought. ‘Or this!’, she added, and she slipped a hand across my stomach and down inside my panties, one finger stroking up and down my slit. The combination of her erotic touch and the image which her words brought to mind was too much for me, and I creamed my panties. I can think of no better word to describe it – they were soaked with the juices which flowed from my pussy, as my whole body trembled with my first-ever experience of an orgasm. My muscles lost all co-ordination and I more or less collapsed on top of Felicity. She rolled me to one side, and her mouth sought mine for a long deep kiss.
I enjoyed the comfort of lying in her arms for a minute, and made no resistance as her hands tugged my panties half-way to my knees, and then down to my ankles. Then she asked me to remove her panties as well, and with a dry mouth and a fluttering stomach, I slipped my fingers inside their elasticated waist and drew them downwards, exposing her cunt. She spread her legs slightly, and I saw that she had quite a prominent mound and her labia were pink, puffy and slightly separated. Her pussy hair was neatly trimmed in a triangle around it, and I gazed with interest as I drew the panties down to her ankles, and then away. Felicity asked me to rub her there, and when I hesitated for a moment she reached for my hand and guided it to her crotch. Touching her there was like an electric shock, sending a jolt of excitement and apprehension through me. As I started to caress her, she directed my motions – telling me to push in first one finger, then another as well, and how to move them around. The feel of her soft inner flesh was strange but intriguing, as it parted softly and wetly before my probing, and her hips pushed up against my downwards motion. Quite soon, her breathing changed to short ragged gasps, coming at ever-shorter intervals, and building up to a kind of broken shuddering yell. After lying for a few seconds with her eyes closed, so that I was just hovering on the edge of anxiety that I had done something wrong, she opened them and gave me a radiant smile. ‘That was wonderful, Sally, I feel so unwound and relaxed,’ she said, and then with a laugh she added: ‘... and horny, too!’, and she playfully grabbed me and rolled me onto my back, to lie where she had just been.
She parted my legs, traced a finger along my slightly open and very moist vagina, and then did an amazing thing. She shuffled backwards on her knees, bent down between my legs and brought her face right up to my pussy. Slowly she licked around it, then up and down, applying a little more penetrative pressure each time. Simultaneously, her hands were parting my labia, and she probed into me with her tongue and her fingers. I was soaking up the revelatory new sensations – not only had I never experienced their like before, I hadn’t even been able to imagine anything of this kind. Felicity entered me further, but then her questing fingers encountered the resistance of my hymen, and at once she stopped. ‘Are you still a virgin?’ she asked, to my ears a little incredulously, and I nodded, slightly abashed. She withdrew her fingers a little, which in my aroused state was the very last thing that I wanted. ‘Don’t stop now!’, I gasped, ‘please – I want to go all the way.’
Felicity looked at me doubtfully. ‘Don’t you want to save it for Miss Henderson?’, she asked, mainly seriously but with a slight teasing look. However, I didn’t have any certainty that Miss Henderson would be interested in me that way or any definite indication that she was a lesbian – just an increasing hope, as I started to think about her consciously in a new and more sexual way. ‘No,’ I replied, ‘you are first – I want you to be my first.’ Felicity seemed pleased as well as clearly excited by the prospect. ‘I’ve never fucked a virgin before,’ she said, ‘I’ll be careful – I promise.’ She said we would not to do it there and then – there wasn’t enough time before we needed to get ready for the evening show, and it also was not the right place for something so special. So I telephoned my parents to say I would be going to a party after the evening show (quite true – but a party just for two!) and would get a lift back, and I promised to be home by 1.00 a.m.
After the last curtain call, we quickly removed our costumes and make-up. Then we slipped away, and Felicity drove me back to her rented apartment on the sea-front promenade. It was on the top floor and we went quietly up the stairs and into the small bed-sit. As soon as we had shut the door, we began kissing and caressing each other, and I let Felicity undress me down to just my panties. Then I helped her out of her clothes, until she was completely naked, and I looked with fresh eyes at the womanly curves of her breasts, waist, stomach, hips and thighs. She knelt in front of me and tugged my panties down, and then pressed her tongue into my pussy, warming and loosening me. I liked the feelings even better this second time, and told her so. As I began to feel warm and flushed, she paused and took down from the top of her wardrobe a locked suitcase, from which she removed two things. I could tell what they were, although this was the first time I had ever seen either of them in real life: one was a vibrator, and other a strap-on plastic dildo. Felicity offered me my choice (and for a split second I though irreverently of picking weapons for a duel), but when I hesitated she recommended the vibrator, saying that she would have more precise control over it. She quickly stripped her bed of its duvet and undersheet, and spread a large beach-towel on the mattress, so as to avoid any tell-tale stains on the bed linen.
I lay down on my back, now a little nervous alongside my excited anticipation. Felicity was so intuitive that she detected this, and instead of proceeding at once to the fucking, she spent some time on foreplay, kissing and caressing me until I was again aroused and melting under her attentions. Without asking further, she slipped the tip of the vibrator about half an inch into my slit, and began working it up and down, easing the opening wider and deeper. At first she used it just as an inanimate rod, but when it was starting to slide easily in and out to a depth of a couple of inches, she switched on the motor. Although not the biggest of vibrators (thank goodness!), this one was well designed both in its shape and in the motions that it made – it was not just a basic one-speed constant, but varied interestingly and unpredictably.
I was already gasping with pleasure when the tip of the vibrator reached and pushed against my hymen. Felicity hooped an arm under my back, half raising me as her mouth feasted on my small young breasts, and my legs felt loosely apart. Her mouth found my neck for a moment, and then my ear. ‘Now?’, she whispered huskily, clearly very aroused herself. ‘Yes, oh yes!’ I assured her, and then a stream of words jumbled and tumbled from my lips: ‘do it, yes – yes, mmm! oh, fuck me, please, take me, fuck me NOW!!’ And on that last high note, her wrist made a deft motion that did not so much push the vibrator through my virginity as twist through it. There was a moment of pain – more than I had thought there would be – but my yelp was muffled by kisses from Felicity. There had been a weird tearing sensation that somehow had not felt wrong, despite the jab of pain and a sharp, almost vinegary, feeling in my pussy. There was anyway no time for a post mortem: the vibrator was now going deeper, definitely into uncharted territory – into virgin country. Nerves and muscles that I had no idea even existed began to respond to the stimulus. I sweated and panted, and thrust my hips upwards in the air in a rhythm that began to build to a new and even more ultimate crescendo. ‘Harder, harder!’ I begged her, as I felt myself at the top of a wave – a tidal wave – that needed to break. I reached for it mentally, whilst audibly whimpering and pleading. Felicity responded to my eagerness and my need, turned up the vibrator’s motor to a rougher and faster level, and giving me deeper and firmer thrusts. I could hear a wailing noise, which I suddenly realised was me, and then for the second time ever, I spasmed and flooded in an orgasm.
I was almost spent after this, and in truth was also a little bit sore between the legs and inside my pussy. I drew Felicity’s body close, kissed her on the lips, and sincerely thanked her for a wonderful introduction to womanhood and to the pleasures that women could have with each other. ‘Be my guest, honey,’ she smiled, and then added more seriously: ‘it’s been a pleasure and an honour.’ We still had nearly two hours left before I would have to be home, which was only about a ten minute drive away. In that time, Felicity got me to use my mouth on her breasts, stomach and vagina, and I had two more new experiences that I was to repeat many a time since then. The first involved my first-ever oral service to a woman’s cunt, and to my relief I found the taste and smell to be fine – unusual, yes; distinctive, yes; but also to be savoured, mixing sweetness with a hint of salt. The second revelation was when she showed me how to ‘69’, which has been one of my most favourite activities ever since – it is so mutually satisfying, so complementary, and if done right can take you both higher than any individual fucking, for you have the sensation of taking someone else over the edge whilst simultaneously losing control of yourself.
The remaining three weeks of the show’s run passed in a blur, with most of my off-stage time spent with my head up Felicity’s skirt or lying on my back and spreading my legs for her pleasure. She was making the most of the little time we had left as well, and I was also seeing her on the days when my alternate was acting the part (for whatever reason, reluctance on one side or instinct on the other, Felicity had made no pass at her), coming to her rooms after the evening performance for a late-night special show all of our own. It went by too soon: the theatre closed at the end of the summer holiday season, and Felicity and I bid each other a slightly tearful, but surprisingly happy, farewell.
Felicity left for Scotland, where she would begin filming the dramatisation of a classic Victorian novel, but for me it was back to school. Miss Henderson resumed taking our class for English lessons, and I still thought she was wonderful – but now I was contemplating her in quite a new way. Four weeks into the autumn term was my sixteenth birthday, and I prepared with care. During the previous couple of weeks, I had unobtrusively followed Miss Henderson after school, shadowing a different bit of her journey each time, as she took a bus across town and then walked to her home. This turned out to be a small house in a quiet suburban neighbourhood, and when I investigated more closely I could see it had been divided into two flats, one on each floor. The bell beside the door of the ground floor flat had the name ‘J. Henderson’, and I knew from overhearing her conversation with another teacher that her first name was Janet – so it seemed that she lived alone. There was a small park and children’s play area further down the street, and I spent most of the weekend before my birthday sitting in it on a bench from which I could see her house – I wore a cap and scarf, and pretended to be reading a newspaper. I saw her a couple of times, but no one else went in or out of her door.
Early on the Saturday afternoon after my birthday, I stood on her doorstep and rang the bell. I had dressed carefully, with white half-length boots and one of my prettiest summer dresses – it hugged my figure nicely above the waist, and had a demure knee-length skirt below. After a moment, Miss Henderson opened the door, looking relaxed in a pair of tight blue jeans and a cut-off white T-shirt, with a bit of her stomach visible between the two. Of course, she was amazed to see me there. ‘Sally? What are you doing here? How did you find ...’, she asked in surprise.
I took advantage of her confusion to step into the hall and close the front door. ‘There’s something I need to see you about’, I said quickly, before I could lose my nerve, ‘are you alone?’ ‘Well ... yes ...’ she replied uncertainly, but before she could say more, I cut in again: ‘It was my sixteenth birthday on Thursday, you know.’ She seemed puzzled, so I continued: ‘I’ve always wanted to do this’, and I kissed her on the lips. For a second she responded; her lips parted and I briefly felt the tip of her tongue, then she took a step backwards and regarded me in shock. ‘Sally!’ she exclaimed, ‘What are you doing? You can’t do that!’
I replied: ‘I have kept a birthday present for you’, and with both hands I lifted the front of my dress up above my waist. She gave a gasp, for I had planned this with care. Under the dress, all that I was wearing was a pair of stockings with a milky-white sheen, held up by the four clips of a thin suspender belt in frilly pink and white. I had no panties, and I had carefully shaved so that my teenage pussy was totally exposed. ‘It’s all yours’, I said. Her mouth opened in amazement, but then she visibly gathered her thoughts, and protested: ‘Sally! I can’t – I’m your teacher!’
‘So teach me – teach me everything you know!’ I replied, which nonplussed her. I could see she was wavering, so I played my last card, and asked the question that Felicity had suggested: ‘Miss Henderson – what did YOU want most in the world when you were sixteen?’
For a moment, she was lost in a distant thought. Almost of its own volition, her right hand came forward to cradle and caress my cunt, her middle fingers stroking my slit and feeling its wetness and openness. I needed no more encouragement, and with one hand I cupped her left breast, feeling the nipple harden through the T-shirt as I brushed my thumb across it. She gave a slight shudder and moan, and then muttered ‘I shouldn’t be doing this’, as she took my hand and pulled me into her bedroom.
For the rest of that wonderful year, during the week at school Miss Henderson taught me English Literature in a class of twenty-six pupils, and on Saturday afternoons at her house she gave me private one-to-one tutorials in lesbian love-making. She was very, very good at both.
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