I was raised in a strict household on the East Coast of the UK. I had 2 sisters a lot older than me however my 3rd sister was just 18 months older. The 2 older sisters had left home by the time my story started in the early to mid 60’s. Some say the swinging 60’s in Britain.
I was just 16 when this all started and my sister still at home was almost 18.
Being the only male in the house, as a little kid I was used to seeing my sisters walk around the house in various states of undress as they prepared to dress for work, go out with friends etc. going to and from the bathroom and bedroom. Being a little kid I guess they saw nothing strange in it and to be honest I just thought they looked funny in what I know now as suspender belts, stockings, bras, panties, putting on makeup etc. It all made me laugh but my how that was to change.
At 16 I was developing my sexual ‘awareness’. I remember shoplifting girlie mags with their black & white photos of girls showing their stockings and suspenders as they sat in a car or on a park bench … all innocent enough stuff but enough to get me roused and yes … when alone in my room I would masturbate looking at these pictures. I didn’t have a girlfriend, I was lacking in confidence and my parents were so Victorian and disapproving. In fact my father was so strict and brutal he would beat me for the slightest misdemeanour .. being the only boy I guess he thought that was OK as he wouldn’t hit the girls. When he did beat me my sister would be very kind and come to my room where inevitably I would be distraught. crying. She would put her arms around me and tell me things would be OK .. just a cuddle I guess. I never put my arms around her.
Although I was older and more ‘aware’ that didn’t stop my sister going around the house on occasions in various states of undress as she got ready for a bath or ready to go out .. much like my older sisters years before. However as I was older she would make attempts to cover up if I happened to see her. What I did see was very provocative I have to admit .. nice shapely legs in dark tan or sheer black stockings usually wearing her stiletto heels, sexy looking full cut see through briefs( I specifically remember a red pair with a heart at the crotch). She pretended to mind if I saw her but also seemed to enjoy me looking at her as she did not hurry to cover up. I remember when she was in her bedroom changing I used to try and look through the crack of the door as she dressed and undressed. Often when she was out I would look through her undie draw as I was developing a ‘thing’ for ladies panties and underwear. I loved the pictures I saw in the magazines I stole and touching real panties used to rouse me in an instant. On more than one occasion I would take a pair of my sisters panties and gently massage my cock through them whipping them away at the last minute before I ejaculated a creamy white stream onto the floor. In fact I recall actually putting the panties on, admiring myself in the mirror with a big bulge and then pulling them down slightly while masturbating until I came over the floor. I put it down to the fact I was developing and it was my way of getting close to a girl…
My parents often went away .. holidays, work etc. leaving my sister and I at home. We were older now, me just leaving school and she at work but both capable of looking after ourselves. On one occasion during an early evening I was sitting in the lounge watching the television. My sister walked in dressed in tight slim pencil skirt and stiletto heeled shoes, the fashion at the time having just come in from work. She plopped herself down beside me then swung her legs up over my lap so her legs were resting on me and declaring she had been on her feet all day and was tired. She asked me to rub her legs. I laughed and said OK and I gently rubbed between her ankles and knees as we both looked at the TV in silence.
After a few minutes she sighed in a relaxed way and asked me to rub and massage higher pushing my hand above her knees. As I massaged I started to push the hem of her skirt up a little as she wanted her thighs massaged as well. The skirt was tight so I had to push a little harder so she raised her bottom and pulled the skirt up for me. I looked down and could see the tops of her stockings and almost the crotch of her red panties. She giggled and told me not to be shy as I had seen her in her stockings before. Nervously I continued massaging her thigh over her stocking tops. She took my hand and made me go higher still so that I was rubbing her suspender belt; her skirt and black lacey slip were almost at her waist and I had full view of her gorgeous red panties with the black heart on the crotch. Now I was getting roused. My God.. unnatural feelings for my sister but she just lay there almost purring like a cat.
After a few minutes she told me she had seen my secret stash of shoplifted girlie mags. Oh no! I thought. She’ll tell my parents or friends … oh no! She just gave a little laugh and asked me why I needed magazines when she was around. I blushed asking what she meant at which she slowly stood up with her skirt high around her waist showing these gorgeous legs. She did a little twirl around so I could see her sexy undies across her shapely bottom and then just stood in front of me her sexy crotch just 18ins. from my face. ‘Well .. what do you think?’ she said quietly. ‘You can say what you want, I won’t tell…’. Am I as sexy as the girls in the magazine?’ I was trembling and she knew it and clearly enjoyed the effect it was having on me.
She sat down beside me again and started stroking my thigh very gently but ending very close to my very hard cock. She remarked that a lot of her friends thought I was becoming quite attractive and said she agreed I was quite good looking. She extended the thigh stroking to just start touching my hard cock but she said nothing. She asked me if I was a very good kisser to which I just gave a nervous giggle. She the said,’let’s see shall we’ and gently pulled my face towards her and with her mouth full open gave me a mind blowing kiss. Jeez! .. incredible. She pulled back briefly then started a full on kissing session with me, massaging my thigh and gently squeezing the cock beneath my trousers. I put my arms over to her and she responded by taking my right hand and placing it on her breasts. I was beside myself, it fealt incredible, I fealt like I was drunk and she just gently continued taking this lead. Needless to say it was all too much and within a minute or two I groaned and came in my trousers with a dark wet stain developing very quickly at my crotch. This time she giggled and said,’What a shame .. you’d better go and clean up’ Which is precisely what I did with my mind whirling. What had just happened???
Similar episodes weren’t repeated however but in the following days my sister did not seem to care so much when getting ready to go out. By that I mean she was not so concerned about covering up in front of me; she just carried on as ‘though it were natural and often asked me to unzip the back of her skirt or buttons at the back of her blouse when getting undressed. Before going out she would ask me how she looked and for her birthday she asked me to give her the money for a low cut bra. When she bought the bra she took great delight in modelling it for me and her milky white breasts did look good. Even when I was alone watching TV she would come into the room to watch something like a rock band or some kind of news item; sometimes fully dressed but often in her undies. On these occasions my eyes were all over her and often she caught me and just giggled saying she knew what I was looking at… I just blushed.
One particular Saturday she came home from work and after lunch said she was meeting friends in town. My parents were away for the weekend so it was just me and her in the house. She went to the bathroom to wash, make-up, change etc. After a while she called out for me to go upstairs to the bathroom which I duly did. There she was putting on her make-up but dressed in her short black lacey slip which just revealed the stocking tops of her American tan stockings. She was wearing black very high stiletto heeled shoes and the low cut bra I had paid for. Her hair was done… all back combed high and her make up on .. lots of dark eye shadow and mascara as girls wore in the 60’s. She was looking in the mirror putting on a pearly pink lipstick and turning to me told me she had a date that afternoon and that she was using a new lipstick; she said that she wanted to test how well it stayed on. Because of that previous kissing session she said she wanted me to kiss her to see how well it stayed on. Nervously I agreed.
She slowly walked towards me and gently holding either side of my neck she kissed me deeply after which she looked in the mirror at herself. She thought the lipstick seemed OK but then kissed me deeply again pushing herself into me. My hands slipped to her waist and then lower to her thighs. I could feel her through her slip, her stocking tops and panties. I started to respond with the kissing and before long we were exchanging passionate kisses with her rubbing herself into me and what was now my very hard cock. After several minutes of this she pulled back and said she thought the lipstick was fine and needed to continue getting ready. What happened next I can’t explain…
Call it bravado, call it impulse, ravenous desire or possibly just confidence but in an instant I said to her, ‘Oh no you don’t!’ With that I took her by the hand and into my bedroom. She giggled asking what I was up to and with that I gently pushed her onto her back on my bed. As she lay there her slip raised I could see the crotch of her panties fully exposed, her stockings on her shapely legs, her stiletto heels and white breasts struggling to escape her bra. I was beside myself and lowered myself on top of her. She giggled but now a little nervously. I told her she was gorgeous even ‘though she was my sister.
Her giggling started to fade away and gently she held my neck pulling me towards her. As she started to kiss me my cock fealt like it would explode but I was doing OK holding back. I slid my hand to her breasts and she kindly turned slowly so I could undo her bra. Her breasts were not big but they were firm as I gently stroked them. I loved her erect nipples and gently kissed them. She just murmured in what I guess was delight. Gently she took my hand and put it to her crotch. Her panties were very damp I remember so well. I was thinking about different things to help stop me from cumming and succeeding too. ‘This is very naughty’ she said softly, ‘No one must know’. With that she reached down to my hard cock and started to unzip the fly of my jeans. Within seconds she expertly held my hard cock in her hand .. Oh my God it fealt good.
The kissing stopped briefly and she looked at me without saying anything. Softly she then said, ‘You want to don’t you?’. I nodded and she said,’Be very careful then and don’t cum in me’. I couldn’t believe what was about to happen. Slowly she raised her bottom and with my help slowly removed her panties. With her legs open she took my very stiff cock and gently put me inside of her moaning as she did. She then slowly wrapped her stocking clad legs around me and pushed upward. Kapow!! My cock slid into this warm wet welcome and sadly with just a few pushes I quickly withdrew showering the tops of her stockings and suspender belt with cum. And did it feel good .. my head was swimming with various thoughts and delighted I was no longer a virgin .. important for a teenager. My sister smiled lying there with cum dripping off her suspender belt onto her pubic hair. Mmm she purred … quite the man now eh? How would you like to do that again? She reached for my cock again smiling at me and gently played with it. I became hard very quickly at which point she pulled me over on top of her and put my cock inside. Again it fealt amazing .. so wet .. so warm. This time as she pushed herself up against me I was able to respond thrusting back at her. She wrapped her legs around me tighter as we really rocked into each other quite physically. She moaned as we did so and her moaning increased. Stupidly I asked if I was hurting her to which she just swiftly replied,’Shh .. don’t stop’. I carried on, I could feel myself wanting to cum again but my sister then all of a sudden gasped, went very stiff and let out a sigh settling back on the bed with a satisfied smile. She then thrust up at me again as if asking me to continue but after a minute or two I quickly pulled my cock out of her cumming all over her already wet suspender belt. I lowered myself beside her and we lay there holding each other for a few minutes just touching and kissing.’ I really have to go and see my friends’ she said and got up picking up her panties and going to her own room. I lay there, my cock exposed and wet. I could not believe I had just had full on sex with my sister but who had seduced whom? Affectionately she returned to my room after a few minutes, dressed and ready to go out. She kissed me tenderly on the lips and said softly ‘Remember it is our little secret ‘ and left.
The following week she came home from work as usual at about 5.30pm. My parents were in the house and I was upstairs in my room. I had been attending day-release college and was doing some homework when I heard her walk up the stairs and pause before coming into my room. She looked smart. Even at the end of the day she was well made up and wearing her smart tight skirt and stilletos. She asked me how I was. I was at my desk facing away from her and she slowly walked over, put her arms around me and gently kissed my neck. She said someting like,’sexy boy’ and kissed me harder then pulled me round towards her and started kissing me passionately. I responded. She said,’shh’ very quietly and I started pulling her skirt up around her waist; needless to say I was already very hard. She just responded by being more passionate and soon she had my cock out and started wanking me. Oh … it fealt good and within a few minutes I gasped and shot cum into her hand and onto her skirt. She giggled, winked and said that I obviously still fancied her. And boy … did I! The evening passed without event.
About 2 weeks later my parents were away for the week. My sister had made no advances and I was too shy to try anything. Before bed one evening she was getting ready for bed wearing a ‘baby doll’ sleepset. This comprised a very short slip and matching panties; the slip was designed intentionally so short so that one could have full view of the panties fitting nicely around the bottom and crotch. She saw me and said someting like how would the sleep set look if she wore high heels and with that she slipped on a pair of white stilletos. And boy it looked very , very sexy. I fancied her like hell .. and she knew it. She asked me what I thought and then after reminding me that our parents were away she took me by the hand into her bedroom. She leaned with her back against the wall and one shapely leg slightly bent inward to hide her panty clad crotch. She was teasing me intentionally. I approached her, held her hands by her side and pushed myself into her. I could feel my hard cock sliding over the soft nylon of the sleep set. She responded by thrusting back…
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