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Romy's Sexual Journey from Schoolgirl to 'Schoolgirl' Part 1

2022-07-06 00:00:03

Hi, my real name is Romy Benson. I’m a pretty successful actor who you would probably know by my stage name (but I’m not going to divulge that here!). Prior to getting married and, I hasten to add, since, I’ve always had a varied and exciting sex life. These days I’m still a fairly tall, blond haired woman with good sized, natural, breasts, a good figure and a shaved pussy. For much of my time as a actor I tended to be cast as a femme fatale in the films I made. Films that I had started making in in the 1960s.

My interest in sex really started when I was about teens. One Saturday morning in the 1950s I was at home whilst my parents had gone out to visit my gran. The only other person in the house was my brother, Joe, who was just over a year older than me. I was doing my homework downstairs when I hit a snag. I needed a ruler and I’d left mine at school. I knew my brother probably had one and popped up to his bedroom to borrow one. He mustn’t have heard me coming up the stairs and opening his bedroom door because there was an immediate rustling, some bed-creaking and a moan. He was lain on his tummy when I entered. ’What the hell do you think you’re doing?’ he shouted, ‘This is my room and you’re not allowed in here!’ That was news to me. It had never been out of bounds to me before. I was a bit non-plussed. I apologised and told him what I’d come up for. ‘Anyway,’ I asked, ‘what were you doing that was so private?’ Then I noticed something. He appeared to be laying on something navy. I recognised what it was immediately. ‘What are you doing with my school knickers?’ I asked. ‘I don’t know what you mean they’re not your school knickers,’ he replied as he tucked the item further under his body. ‘Go on Joe I’d love to know what you’re up to that’s so secretive. Is it naughty? I won’t tell anyone if it is. Honest. I’m just curious,’ I said. Joe seemed to be turning it over in his mind, ’Well, if you really won’t mention it to anyone else. And, remember, a promise is a promise. OK? I’ll tell you. I was just having a wank,’ he stated. ‘What’s a wank?’ I asked. ‘It’s what boys do by rubbing their cocks for a while,’ he replied. This was such a mystery to me. Odd sounding words and funny references I hadn’t got any idea about. I knew boys referred to their penis as a cock sometimes but I hadn’t seen a penis since Joe and I used to be bathed together when we were very young. From my recollection his ‘cock’ was a floppy little flap of skin in between his legs. ‘Can I watch you ‘wank’ then?’ I asked. ‘It’s a bit rude. And it might shock you too. So are you sure?’ he replied. ‘Yes,’ I said, ‘I’m very sure.’ And with that reassurance from me he turned over onto his back. What I saw was amazing. Joe’s penis was sticking straight up. Far, far bigger that I ever remember it. It was also very, very pink. Even quite red in places. I came forward to get a closer look. Then I did indeed see my navy school knickers on the bed. ‘What are you using my knickers for? And where did you get them?’ I asked non-confrontationally. ‘I often find your, used, knickers left around the place. You’re not the tidiest person in the world and, some time ago, I just wondered what it would feel like to rub my cock with them. I’ve been wanking with them for ages now. I just have to be careful I don’t get cum on them!’ he informed me. ‘What’s come? I asked. ‘Ah,’ replied Joe, ‘It’s spelled c. u. m.,’ he explained, ‘And it’s the stuff that comes out of my cock when I have an orgasm. But before we get into what an orgasm is etc. I should probably demonstrate.’ He started to rub his cock. I got even closer to him. I was fascinated. And sure enough he started to rub it with my knickers. After only a few minutes he said, ‘Stand by I’m about to cum. Step back a little ‘cos the spunk that comes out sometimes flies into the air and, although it’s not dangerous, it can leave a bit of a stain sometimes.’ I did as he asked and not before time. Joe closed his eyes very tightly, threw aside my navy knickers and started to ‘cum’ (As I’d been informed). And what a sight it was to see too. All that cum shooting out and Joe’s obvious enjoyment of it gave me a funny feeling in my ‘tuppy’ area (as my mum called it). Gradually, Joe, who had sort of flopped back onto his bed, started to regain control of himself. ‘There,’ he said, ‘That’s a boy cumming. What did you think?’ ‘Frankly, Joe,’ I replied, ‘That was the most exciting thing I’ve ever seen. Can you do it again for me, please?’ ‘It’s not as simple as that I’m afraid,’ he informed me, ‘I need a little bit of time to build up my spunk again. But if you really want to watch it again I’ll let you know when I’m going to do it.’ I was thrilled. And so began my interest in sex.

Over the next few of months, until Joe went off to university, we had hundreds of sex sessions. He eventually let me wank him lots of times (often with my navy blue knickers), I once licked his cock after he came and tasted his spunk. It was nice and I did it a few more times after that. Furthermore, he started to instruct me how girls could also have cums by stroking their ‘tuppies’. I always did that with my knickers on, even in front of Joe, I just felt very self-conscious about him seeing my pussy. But I did discover that I got the most enjoyment by stroking my pussy slowly and gently after making sure that I had lubricated it before I started if I wasn’t moist enough.

When I was in my laterteens I regularly got dates with guys from my school class or school year. I had, by then fairly good sized breasts, with a slim but quite curvy figure. Dates usually involved a visit to the cinema where, because it was dark, the guys thought it was open season to grope me. In some ways I didn’t mind because my fascination was with their cocks. Firstly, though I had to let them squeeze my breasts then start to rummage under my skirt. To make things easier for them I never wore any knickers (which they did seem to find particularly tricky to negotiate their way past without my help!). But in every case they tended to be get themselves so excited that they ended up almost ‘attacking’ my pussy. Never moistening their fingers before trying to get entry into my pussy hole and they never, ever found my clitoris! I always needed to fake an orgasm as soon as I could. Of course they thought to themselves how brilliant they were at bringing me to an instant orgasm whereas I just wanted them to leave, what was a very sensitive part of my anatomy, alone. More often than not, they scratched me down there and it took me quite a while to recover. But the bit I liked best of all was wanking them. I guess, with all my past experience with Joe’s cock, it meant I could usually get the guy to spunk within seconds! Depending how much they’d hurt me with their cack-handed assault on my pussy resulted in me spraying their spunk in the worst place (all over the front of their trousers or on their jumper. ‘Sorry!’) or into my hand, then on to my handkerchief if they’d been not too bad. I never saw these dates more than once anyway.

My parents came into a bit of inheritance money and thought it would be a good idea to send me to an all girl’s boarding school, a fair distance away, for the Sixth Form years of my schooling. So at the beginning of the next school year I found myself ensconced at St Winifred’s School For Girls. I have to say it was a bit of a shock to my system to have been in a mixed sex school and then, within weeks, to a school only full of girls. After, initially, having problems settling in (a not unusual experience according to Matron) I started to make friends with a few of the girls - mainly the full time boarders like myself. Six of us shared a dorm on the top floor of the school building and after lights out used to chatter about lots of things but mainly centred around boys and sex. As I had just come from a school half-full of boys I quickly became the centre of attention. I didn’t go into a lot of details at first mainly because I didn’t know them that well but one particular incident occurred and really broke the ice! One night the girls were talking about orgasms (We all had a good, quiet wank when we settled down after lights out). Margie, was a lovely, fairly tall and large chested girl who was very popular with us all. One night she asked us, ‘When you have a cum does cum actually come out of your pussy?’ ‘What do you mean, Margie? I get pretty wet with some juices but that’s natural I think,’ I replied. ’No,’ she said, ‘it’s like a white, sticky stuff that comes out of me.’ We were all intrigued. ‘Shall I show you?’ she asked. The consensus of opinion was that she should. ‘OK,’ she said. Margie sat up on her bed’s headboard, pulled up her nightie and pulled down her bottle green school knickers. (We all had to wear our knickers at night in case we had to suddenly leave the building in case of fire or something). A couple of the girls had torches which they shone on Margie’s slightly hairy pussy whilst she started to wank herself. She was quite slow and deliberate alternating between putting her fingers in her hole and gently rubbing her clit. She started to edge towards her orgasm. She was experiencing more and more little quivers through her body then let rip with a full blown cum. And she was so right. Out of her pussy seeped a white liquid that looked like spunk to me. ‘It looks like spunk,’ I said. ‘How do you know’ asked one or two of the girls. I ignored them for the moment whilst getting closer and closer to Margie’s pussy. I leant right up to it and licked the pussy cream. She shuddered (another slight orgasm perhaps?). It was the first time I’d ever licked another girl’s pussy and it rather turned me on. ‘And it tastes a bit like spunk as well,’ I announced. Again there was an even bigger wail of, ‘How do you know?’ ‘It’s getting a bit late now but I’ll tell you more tomorrow night. OK?’ I replied.

So, over the next few nights I regaled them with stories of spunking cocks; of how cocks spurted their spunk a long way sometimes; of what spunk smelt like and what it tasted like and how you rubbed a cock to get it to cum. The rest of the girls were enthralled and certainly whilst I was relating my stories there was quite a bit of action taking place with hands down knickers followed by murmured groans.

For all that we didn’t have boys in our school we were, sort of, teamed with boys from a Grammar school a short distance away. We joined up for one or two activities throughout the year - Barn Dances, Sports Days etc. Through these activities I got to know a few of the boys to talk to. Having been in a co-educational school only a short time before I wasn’t cowed by their presence like a lot of my friends were who often got rather tongue-tied when near the boys. In the dorm prior to one of our get togethers the girls challenged me to pick-up a boy (or boys) and take him somewhere so they could watch me wanking him. I was game for that if it could be arranged. I managed to get a note delivered to a boy called Paul who I had got talking to and dancing with at a previous Saturday dance. Talking was about as far as it ever went though because any real fraternisation was heavily discouraged by the staff.

Both Schools were all due to have a joint Cross Country Run on a forthcoming Saturday and I arranged that at a prearranged spot, in a little copse of trees we passed on the run, I would peel off from the run and if he, or one or two of his friends, did the same I’d give them a bit of a treat. Meanwhile, a few of my fellow pupils, who would pretend they’d got an injury or it was the wrong time of the month would secrete themselves in the copse prior to me and the boy (Boys?) arriving. Dressed in my PE kit, consisting of a yellow aertex shirt and my bottle green school knickers I set off with the participants of both schools on the run. But when I got to the agreed location I found five boys from the Grammar School hanging around in a little clearing. ‘Hi,’ I said to Paul, ‘There’s a few more than I expected. Not to worry, I’m sure I’ll manage,’ and arranged them in a circle. I could hear a bit of rustling going on in the background which I assumed were the other girls getting a good viewing spot. ‘I don’t know how many of you have ever been wanked by a girl but I’m pretty sure you’ll enjoy the experience. Can you guys just lower your shorts and let me see your cocks please?’ Suddenly, there in front of me were five lovely cocks most of which were in quite a state of arousal already. I started. Bending down beside the first boy I lay both my hands on his cock. He stiffened immediately. I sucked it for a few moments to get lubricated then began to wank him. I guess he must have been pretty worked up already because he came virtually straight away. Spraying all over the ground in front of him. Luckily, as soon as I notice he was about to cum I moved quickly to one side to avoid being sprayed. The next boy, having seen me wank his friend, was already almost at orgasm point himself. I decided not to suck him incase he off-loaded a cock full of spunk into my mouth. A couple more strokes and he was gone. Spunk shot out and landed several feet away, (Very impressive!). The next boy was also pretty steamed up, so much so that as soon as I touched his cock he came. He sprayed some of his cum onto my leg because I failed to move quickly enough. I didn’t mind. I simply wiped it off with my finger and popped it in my mouth. The fourth boy had a lovely, good sized cock for a fairly young boy. ‘I’ll enjoy stroking this one,’ I thought to myself. And it was indeed a bit of a handful. I reckon it stiffened another inch at least when I lubricated it with my mouth. He was be far the most restrained and appeared to be absolutely ecstatic as I stroked his rampant member. But he couldn’t hold out forever and soon his hot sticky spunk sprayed the ground around his feet. That left Paul to be seen too. ‘Are you ready Paul?’ I asked. ‘I should say so’ he replied holding his rampant cock in his right hand and slowly stroking it. ‘There’s just one problem I’m afraid,’ I said. ‘Oh what’s that?’ he asked, probably expecting me to say I was too tired or something. He certainly looked a bit crestfallen. ‘No,’ I said, ‘Don’t worry. It’s just that all these cocks around me have made me incredibly horny and I’d really like you to wank me first. OK?’ ‘Yes,’ he replied, ‘I’ve never done it to a girl before though. Tell me what to do and I’ll very happily give it a go.’ So I moved him round to my back so his cock was rubbing against the back of my knickers and, sucking his fingers to get them wet enough to enter my pussy (If the truth be told my pussy was already pretty wet but it’s good idea to teach someone how to carefully handle a pussy and clit), pulled the front of my knickers out a little and said to him, ‘Slide your hand down the front of my knickers, Paul. Down there you’ll feel two things. Firstly, a little bump which is my clitoris and below that a sort of slit which is my pussy. Slide a finger into my pussy first then slide it up to my clitoris and give that a very gentle rub. If you keep doing that for a little while I’ll cum. OK. Off you go.’ I have to say, Paul, carried out my ‘orders’ perfectly. He was careful and gentle and, probably because I was already well worked up, I came! Wow! ‘Well done, Paul. That was beautiful. Thanks,’ I said, ‘And now let me return the compliment. Oh! and thank you for not cumming on the back of my knickers. Might have taken explaining when I got back to school if you had!’ I took hold of his lovely cock and rather hand wanking him I started to suck him. Seconds later out shot his spunk. Quite a load too but swallowing it wasn’t a problem. Paul, was fully drained and a bit wobbly-legged as I left him and the rest of the guys to get back into the race. I feigned a damaged hamstring and limped my way back to school.

That night as we settled in our beds there was only one topic of conversation. All the girls had wanked themselves silly as they reviewed what was happening before them. ‘Watching you extract all the spunk from the four boys you wanked had been erotic enough, but allowing that boy to wank you was absolutely brilliant. And then to suck the cum from his cock and swallow it will live long in all our memories I reckon,’ And I’m sure that’s not to mention their fingers as they beat a cum out of their own from their very swollen pussies.

And talking of swollen pussies. My joint experience with Margie and her creamy pussy had intrigued all of us but my licking of her pussy had sent an ‘electric charge’ through us both. My feeling was that both Margie and me maybe wanted to push things a little further. Many of the girls had sexual relationships with each other. Mainly, it seems, it was wanking each other off while sharing a bed. And though this could be fraught with danger — if Matron, on her nightly rounds, caught anyone there was hell to pay! Margie caught me on my own one day studying a play *********** (I was already leaning towards a career in the theatre if I could get to Drama College) and asked if we could have a bit of a ‘snuggle’ together sometime. I said that I thought might like that. I asked her what she would like out of any liaison - a wanking; a licked cum or a bit of mutual masturbation. ‘A bit of all of those would be wonderful,’ she told me, ‘But I can’t get over the feeling you gave me when you licked my pussy.’ ‘OK,’ I replied.

Every night we all had to have a shower prior to getting ready for bed. Thereafter our time was usually our own. Some of the girls went down and watched the TV in the TV lounge. Some went to the library but most of them didn’t return to the dorm until just before lights out at 9 o’clock. A couple of nights after our previous discussion I sought out Margie as she came out of the shower room wrapped in a large white towel. ‘Leave your knickers off when you get ready for bed,’ I said, ‘I’ll be along in a few minutes.’ and went for my own shower. When I went up to our dorm I found Margie sitting on her own on her bed dressed in her nightie and, with her knees up, could clearly see she hadn’t got her knickers on. ‘That’s a lovely sight,’ I ventured, ‘I must take a closer look.’ I popped on my knickers and nightie. I asked Margie to, initially, sit on the end of the bed with her nightie pulled up. I pulled it up a bit further so I could suckle on her lovely breasts and nipples for a few moments, then asked her to lay back whilst I got a very close look at her pussy. She was obviously a bit excited in that region because she was extremely swollen. He clitoris was just starting to emerge from it’s hood as I stated to carefully lick around it. It quickly started to enlarge and Margie started to moan a little. Working my way a little further down I gently spread her pussy lips open with my fingers and started to dart my tongue in and out of her pussy hole. And boy did she like that! I don’t know how long it look but it seemed like seconds before she started her orgasm. She shivered and shook and trapped my head between her thighs as she had the most amazing cum. As she eased away from her orgasm I looked at her pussy and there was a fantastic amount of creamy girl spunk starting to seep out of it. I watched it for a while then closed in on it and sucked it all up. ‘Wow! again, Romy, that was incredible, Thank you so much. Now let me give you a wank. Doubt I’ll be able to do it as well as you, I’m afraid.’ But with a bit of gentle coaxing from me Margie did give me a very much needed cum. ‘That was just lovely, Margie,’ I told her, ‘Thanks.’ We kissed each other and that was that. We never repeated our ‘liaison’ but I have to say it was a fantastic experience (for both of us) and certainly ‘scratched an itch’ that we both needed scratching!

A few weeks before the end of the school year, when I would be leaving St. W’s to go down to London to study at a London Drama Academy, I decided that I was going to lose my virginity. I had already decided who was going to take it too — Paul. He from the local Grammar school who I’d sucked off a few months ago. An event had been organised between our two schools to do a sort of ‘Top of the Form’ quiz show. The Grammar school against us but it did give me a chance to slip a note to Paul. It read ‘I want you to be my very first fuck. You name the date and place x’. I watched him as he read it and he went bright red!! Not surprising really. I don’t suppose he had many invites like that one.

A week or so later I received a return note. Paul had a friend who’s sister was in my school so passing a note wasn’t that hard. Paul, who was not a boarder like me but lived locally, said in his note that ‘he would love to ‘help me out’! That his parents and younger sister where all away this coming weekend so he’d meet me at the main bus station at 10 o’clock on Saturday morning.’ I was rather excited and was desperate to have wank after wank in anticipation but thought it would be better to keep my libido in check till Saturday.

At St. W’s we boarders were allowed to odd trip into town on a Saturday as long as we were not in groups any larger than four and we must always wear our school uniform (this was a sort of control on us by thinking that we would be easily identified if we got up to any tomfoolery). When Saturday arrived the four of us caught the bus outside the School gates. We always went upstairs on the bus so it gave the bus conductor and anyone behind us a teasingly, lovely view of our knickers as we climbed the stairs. When we got to the Bus Station Paul was waiting. The other girls knew what I was up to and couldn’t wait to hear all about it later. Paul’s house was a short walk from the town centre and only took us about 10 minutes to get there. ‘Shall we go to my bedroom?’ he asked. ‘That would be good,’ I replied. His bedroom was still like a young teenager’s bedroom with posters of footballers, Model aircraft hanging from the ceiling and so on. I started to take my clothes off as did he. My school knickers were the last things I took off and lay myself on the bed. Paul was obviously a bit apprehensive and said ‘Is it going to be messy and a bit bloody?’ he asked. ‘No,’ I replied, ‘Don’t worry, my hymen must have been broken ages ago with the amount of stuff I’ve poked up my pussy when I’ve wanked myself off.’ He removed his underpants and there before me stood his lovely cock. He was already pretty big as he gazed at me in the nude. With my largish breasts and my shaved pussy who wouldn’t be? He joined me on the bed and grabbed one of my breasts but I said, ‘Whoa! Gently please Paul.’ ‘Guess I’m a bit over eager. Sorry,’ he replied. So I, kind of, took over instructing him how to kiss, stroke and lick my breasts in order to get my juices flowing further down, then, although he had done this before, how to fiddle with both my pussy and clit. Without any hard work from me his cock was very, very rigid in my hands. I stroked it until I could feel he was starting enjoy it a bit too much.’Steady,’ I said, ‘I don’t want you to cum too quickly. And I certainly don’t want you cumming inside me either. So you must pull out if you feel you’re about to cum. OK?’ I lay back, opened my legs fairly wide, wet my pussy by pulling out some of my internal juices and guided his cock to my pussy lips. ‘OK, Paul, just ease your cock into me,’ I instructed. He did as I asked and the feeling was incredible — it certainly beat the various vegetables, candles and garden trowel handles I had used in the past! — and gradually Paul began to move. ‘Sorry,’ he said, ‘ I’m already about to cum!’ I pulled him out and cum he did all over my breasts and tummy. ‘I’m really sorry, Romy,’ he said, ’The feeling in there was just so wonderful that I couldn’t hold it back.’ ‘Don’t worry, Paul, I quite understand. Let’s see what your powers of recovery are like and you probably won’t be as worked up next time.’ Within minutes with me stroking and licking his cock it was full size again. Again I moistened my pussy and popped him into me. We got into a lovely rhythm together and it wasn’t long until I had my first ‘cock’ cum and it was simply amazing. Paul had obviously realised I’d had cum and made to pull his still very engorged cock out of my pussy when I said, ‘Not so quick! Us ladies aren’t quite like you men in that we can sometimes have many orgasms in a row. And that’s certainly how I feel right now. So just plough on, please.’ My second orgasm happened just moments later and it was a whopper! The third was even better but took a little longer for me to ‘explode'! ‘Phew! I think that’s about it from me just for the moment. Think it’s about time I extracted some more cum from that lovely cock of yours though.’ I proceeded to wank and suck him till he came in my mouth. I swallowed. I had another couple of cums after that but by now we were both pretty much spent. We decided to get up and get dressed. As I was about to pull on my school knickers Paul said, ‘Romy, do you think I could have your knickers as a keepsake to remember this day for ever. I had no problem with that request. And after saying good bye and wishing each other all the best for the future we parted probably never to see each other again. Devoid of knickers the bus conductor and the two men that followed me upstairs must have thought it was their birthdays and Christmas’s all rolled into one with, ahead of them a puffed up, hairless and well-used pussy in view.

To be continued.