The White Sissy Slave Society A Walk into Sissyhood
- 3 years ago
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My Ongoing Sissy Story, Part 2 free porn video
As some of you liked my story (my first time as a sissy) I thought I would follow it up with my next encounter.
Some 10 years had passed since my affair with Andy and I was now happily married with a family although I used to sometimes reflect on the lovely times I had with him but had decided that my bi crossdressing side was firmly locked away and that Nicole, my alter ego, was locked away with it. The only thing that remained from that era was my dislike of body hair so I was super smooth all over and my love of using a butt plug or dildo on myself.
I was now employed as a sales representative covering the North of the UK and loved my job as it was varied and no two days were ever the same, this was most certainly the case one fine autumn day! I had made an appointment with a designer to explain our product range after he had visited our stand at an exhibition. I arrived for my appointment slightly early at a private house, rechecked the address and it was correct. Some designers prefer to work from home whilst others prefer the office setting. So I got my presentation folder and rang the doorbell and after a couple of minutes it was opened by Peter, my prospective customer.
He was I would guess around late 40’s, nicely suntanned and well groomed. I apologized for being a bit early and he said not to worry and ushered me in to a large lounge overlooking the private rear garden and swimming pool but more of that later!
After a cup of tea and chit chat we got down to business sitting opposite each other with a coffee table in between and it was only then that I realized he was wearing either stockings or tights as they were clearly visible at his ankles! Anyway, I carried on showing him technical drawings of the range he was interested in but must admit I found it very hard to concentrate, so much so that Peter asked if I was ok. Yes I said glancing down at his ankles and then Peter must have realized that he was wearing nylons and went cherry red with embarrassment. To save him from further embarrassment I asked if they were tights or stockings and he said stockings. I went on to tell him that I had once been into wearing sexy lingerie and all of a sudden we were discussing bras, panties and other girly clothes as if we had known each other for ages and not under an hour!
I told him about my fling with Andy and that I had only ever been with him, he said he had his first experience at school with a teacher and they kept on seeing each other until he went to University, after that he concentrated on getting his degree with no distractions, either male or female. He showed me a photo of his partner Jill and they had been together for over 20 years but never had k**s. He confided in me that he suffered from erection problems and would often go limp after he had entered her which at first was frustrating to both of them but they had come up with a simple solution ----a strapon! He said he was really good at fucking her with that and she usually had at least a couple of orgasms before she used the strapon on him. He used to dress for her in, as he described it, a slutty schoolgirl outfit which really got my attention. Evidently that was one of Jill’s favourite scenarios as she would first of all restrain him, then spank and sometimes even cane him before fucking him with the strapon. I said that was amazing and told him Andy liked me in a similar outfit before our lovemaking sessions, Peter winked and said we can have lots of fun together but I think we will have a schoolgirl theme sooner rather than later!! I had to pinch myself that this was happening but yes it was and Nicole, now out of her long sleep, was ready & raring to go.
I got up to go and sit next to him but Peter said we would be more comfortable upstairs so I duly followed him into a bedroom, again overlooking the rear garden. The curtains were only slightly open and Peter shut them before turning on the lights. My heart was pounding and I was trembling with excitement and it came to me in a flash that Nicole was back and ready to play.
Peter again asked if I was ok and I mumbled yes but that I was really nervous and excited at the same time. He put his arms around me and we just stood like that for a couple of mins before he kissed me on my neck and eventually we were kissing passionately, out tongues probing each other’s mouths. There is something massively erotic about kissing a man as you can feel the power and lust being transmitted in huge waves! When we finally came up for air Peter said “Crikey, you are really hot” which made me really happy. My hand went down to feel his rock hard cock straining against his trousers and he did the same to me. We stood back from each other and Peter said “Well, this is certainly an unexpected pleasure” and guided me by the hand to sit on the bed with him sitting next to me. He asked if I would like to get changed into something nice and girly and I said oh yes please.
We both went into another room which was kitted out as a home office, however against one wall there were floor to ceiling cupboards. He opened a couple and they were racked out with drawers and hanging space which had a couple of short black dresses, several miniskirts including 3 or 4 schoolgirl ones and some white blouses, scarfs, shoes and boots etc. Wow I thought to myself standing back and feasting my eyes on this Aladdin’s cave!! Peter could see the excited look on my face and asked if I approved, rather I said dreamily. He then pulled open the drawers which contained a gorgeous selection of bras, panties, stockings, tights, dildos, butt plugs, a spanking paddle and other bdsm gear.
I asked him about the bdsm stuff as it was something, with the exception of being spanked by Andy, I had no experience of. He said that Jill was really into it and it turned her on to be the domineering woman in the relationship which he was ok with as he enjoyed it as well. He said we can try some tame bondage & spanking to start with and if I liked it we could try more ambitious things. I loved the way he described the various role plays and it was making me so horny I could scream with pure excitement!
Peter selected a black bra & matching lace panties, a suspender belt and stockings and left me to get changed which I did at super quick speed, relishing the feeling of being Nicole once again. My cock by this time was hard and the end just oozing a bit of precum which I tasted, mmm lovely!
I called for Peter and he returned only this time also wearing a similar outfit to mine but with white bra & panties and black stockings. The contrast between the white lingerie and his deeply tanned body was really erotic and a massive turn on, not that I needed any encouragement there!! I said wow you were as quick at getting changed as I was but he admitted he had been wearing them under his male clothes as had to get dressed quickly when the doorbell went otherwise he would have been changed into all male clothes. I told him I was so glad I was early otherwise we would not be standing together now dressed in lingerie! Fate works in strange ways indeed!
He kissed me deeply whilst his hands caressed my bum through the panties saying that he liked very much what he was feeling and I said likewise. By this time we were lying on the bed feeling other’s cocks (or clit as I started to think of mine as) whilst kissing and caressing. He asked if I was ok and I told him I felt I was getting near to orgasm which he said was ok as long as I could cum again which I said yes to. It’s really difficult to describe the emotions that were exploding within me and I was completely powerless to resist them even if I had wanted to which in my highly aroused state was nigh on impossible. By this time our panties were off and we got into a 69 with me on top, Peter’s cock was I guess about 8” uncut and stood like a rocket, I gently pulled down his foreskin and took him in my mouth, first licking and then swallowing him as far I could get without choking. Peter was doing the same to me but also licking my pussy-hole as well and the feeling was really intense. I rolled off Peter and he asked if he could fuck me, oh yes please you gorgeous man I cried and he got me into doggy position, put some lube on his fingers and started to finger me, first one finger, then two and finally three. He was really gentle and asked if was ok and he was ready to fuck ne if I was, I said could we call it making love instead of fucking and yes I was eager to feel his massive cock inside me. I use a butt plug a lot at home as really enjoy the sensation but my plug was nowhere near as thick as Peter’s cock so I asked him to be very gentle and slow. I could feel the tip of his shaft starting to push inside me and the feeling was wonderful. He pushed his cock a bit further into me and was whispering that I was the most gorgeous girl and that he wanted this to go on for ever. With a final push he was all the way inside me and I started to push back enjoying every second of being the girl. He started to thrust faster and I could hear his balls bouncing off my cheeks , this went on for a few mins then I could feel his cock swell inside me before with a cry he shot his spunk deep inside me. I thought he would pull straight out but he didn’t, instead leaving his twitching cock inside me whilst whispering romantic things in my ear. Finally with a squelch he pulled out and flipped me on to my back with him lying beside me propped up on his elbow. He asked me to clench my bum cheeks together as he wanted to lick the spunk out once he had his breath back! We lay like this for a while, kissing and cuddling each other. Peter asked if I wanted to cum yet and could he suck me and swallow if I did or would I prefer to fuck him. Without realizing it I had reverted back to Nicole mode and said if it was ok with him I would prefer to be the girl which he readily agreed to. He told me he had been waiting for a long time for someone like me to come along and that now he had found me he would make sure I was happy. I told him about my first time and how deeply I had felt for Andy and that me being the girl just felt right.
We had been cuddling and stroking each other and Peter took my soaking wet clitty in his mouth and very gently began to lick me whilst at the same time pulling my foreskin back, in no time at all I could feel an inferno starting within me and cried out I was cumming and I shot my massive load of creamy thick spunk into Peter’s mouth. It seemed to go on for ever, the spunk just pumping out until finally it stopped. Peter kissed me letting me swallow some of my own spunk which tasted lovely and creamy, yummy! We lay side by side for a while and Peter asked me to squat over his mouth which I gladly did letting his spunk flow out of my pussy and into his mouth. We kissed some more and Peter said let’s have a break and passed me a gown to put on before going downstairs.
I told him I couldn’t stay all day as had another appointment a few miles away in the afternoon but he told me he had a solution to keep my firm happy and wrote out a very large order promising me this was the start of a profitable relationship in more ways than one! I asked if I could borrow his ‘phone (this was before mobiles were in common use) and rang may 2.30pm appointment and asked if I could reschedule it because something unexpected had come up and they said not a problem. I next called the office to tell them that I had rearranged my afternoon appointment as my morning call was more complex than I was first led to believe so I could now concentrate on enjoying myself with Peter.
Whilst I was on the ‘phone Peter was sucking my clitty back to hardness so we returned back to the bedroom and lay back on the bed together. Peter was rock hard again and I asked him how many time he could cum in a day and he reckoned maybe 4 or even 5, wow I said that’s an awful lot of cream and could I have it all please to which he replied it’s all for you my gorgeous girl. It was quite uncanny how quickly we had accepted that he was the man & I the girl.
We talked about what turned us on apart from each other and found out we had a lot in common, I used to love dressing as a schoolgirl for Andy and Peter said it was a big fantasy for him to seduce one with a cock!! Well I said I’m here for the taking!! We got into a 69 again and Peter gave equal attention to my still wet pussy and now hard cock. He told me he was ready to make love again and this time I lay on my back with my legs over his shoulders. He entered me easily this time as my pussy was still soaking wet with his spunk and fucked me nice and slowly, nearly pulling out before pushing himself deep inside me. During this we were kissing, murmuring all sorts of soppy things to each other! Peter pulled out and lay beside me, I asked if everything was ok and he said yes but he was conscious that he seemed to be having all the fun so what would I like to do. He suggested maybe a bit of role play and I readily agreed thinking to myself all the time that I was incredibly lucky to have found such a lovely & considerate man as a lover.
We went back into the office room and looked through the various skirts etc and I said I would love to dress as a schoolgirl for him knowing it was a fantasy for him as he had mentioned it earlier.
He told me to pick my outfit out so I selected a grey pleated mini skirt, short sleeved white blouse and tie and some black shoes, however something was missing so I asked if he had any white knee length socks as that would make me a proper schoolgirl and unfortunately he hadn’t but said he would get some for next time. Having got dressed in my uniform (still wearing stockings & suspenders) I returned to the bedroom.
Peter instructed me to bend over the bed which I did, he then pulled my skirt up and started spanking me through my panties first quite gently but gradually getting harder and harder before he pulled my panties down to me knees and spanked me on my bare bottom. The spanking was quite hard by this time and was beginning to hurt so I whimpered and he stopped, bending down to first kiss my cheeks before sticking his tongue deep inside my pussy. The feeling was exquisite and was further enhanced by my cheeks which were stinging after the spanking! He stood up and I felt his cock beginning to enter me and without further ado he thrust his length into me and started to fuck me in long slow strokes, I could hear my pussy squelching like a wellington boot in mud and gradually his strokes became faster and faster before he cried out and shot his spunk deep inside me. This time he pulled out and started to lick my pussy whilst I started to wank myself off, I was getting close when Peter positioned me on my back and started sucking and licking me and I shot my load once again in his mouth and like last time he kissed me immediately after dribbling my spunk into my mouth which I received like a good little slut.
It was past lunchtime when we finally finished our lovemaking and went & had a shower together.
There is more to tell if anyone would like me to continue?
Some 10 years had passed since my affair with Andy and I was now happily married with a family although I used to sometimes reflect on the lovely times I had with him but had decided that my bi crossdressing side was firmly locked away and that Nicole, my alter ego, was locked away with it. The only thing that remained from that era was my dislike of body hair so I was super smooth all over and my love of using a butt plug or dildo on myself.
I was now employed as a sales representative covering the North of the UK and loved my job as it was varied and no two days were ever the same, this was most certainly the case one fine autumn day! I had made an appointment with a designer to explain our product range after he had visited our stand at an exhibition. I arrived for my appointment slightly early at a private house, rechecked the address and it was correct. Some designers prefer to work from home whilst others prefer the office setting. So I got my presentation folder and rang the doorbell and after a couple of minutes it was opened by Peter, my prospective customer.
He was I would guess around late 40’s, nicely suntanned and well groomed. I apologized for being a bit early and he said not to worry and ushered me in to a large lounge overlooking the private rear garden and swimming pool but more of that later!
After a cup of tea and chit chat we got down to business sitting opposite each other with a coffee table in between and it was only then that I realized he was wearing either stockings or tights as they were clearly visible at his ankles! Anyway, I carried on showing him technical drawings of the range he was interested in but must admit I found it very hard to concentrate, so much so that Peter asked if I was ok. Yes I said glancing down at his ankles and then Peter must have realized that he was wearing nylons and went cherry red with embarrassment. To save him from further embarrassment I asked if they were tights or stockings and he said stockings. I went on to tell him that I had once been into wearing sexy lingerie and all of a sudden we were discussing bras, panties and other girly clothes as if we had known each other for ages and not under an hour!
I told him about my fling with Andy and that I had only ever been with him, he said he had his first experience at school with a teacher and they kept on seeing each other until he went to University, after that he concentrated on getting his degree with no distractions, either male or female. He showed me a photo of his partner Jill and they had been together for over 20 years but never had k**s. He confided in me that he suffered from erection problems and would often go limp after he had entered her which at first was frustrating to both of them but they had come up with a simple solution ----a strapon! He said he was really good at fucking her with that and she usually had at least a couple of orgasms before she used the strapon on him. He used to dress for her in, as he described it, a slutty schoolgirl outfit which really got my attention. Evidently that was one of Jill’s favourite scenarios as she would first of all restrain him, then spank and sometimes even cane him before fucking him with the strapon. I said that was amazing and told him Andy liked me in a similar outfit before our lovemaking sessions, Peter winked and said we can have lots of fun together but I think we will have a schoolgirl theme sooner rather than later!! I had to pinch myself that this was happening but yes it was and Nicole, now out of her long sleep, was ready & raring to go.
I got up to go and sit next to him but Peter said we would be more comfortable upstairs so I duly followed him into a bedroom, again overlooking the rear garden. The curtains were only slightly open and Peter shut them before turning on the lights. My heart was pounding and I was trembling with excitement and it came to me in a flash that Nicole was back and ready to play.
Peter again asked if I was ok and I mumbled yes but that I was really nervous and excited at the same time. He put his arms around me and we just stood like that for a couple of mins before he kissed me on my neck and eventually we were kissing passionately, out tongues probing each other’s mouths. There is something massively erotic about kissing a man as you can feel the power and lust being transmitted in huge waves! When we finally came up for air Peter said “Crikey, you are really hot” which made me really happy. My hand went down to feel his rock hard cock straining against his trousers and he did the same to me. We stood back from each other and Peter said “Well, this is certainly an unexpected pleasure” and guided me by the hand to sit on the bed with him sitting next to me. He asked if I would like to get changed into something nice and girly and I said oh yes please.
We both went into another room which was kitted out as a home office, however against one wall there were floor to ceiling cupboards. He opened a couple and they were racked out with drawers and hanging space which had a couple of short black dresses, several miniskirts including 3 or 4 schoolgirl ones and some white blouses, scarfs, shoes and boots etc. Wow I thought to myself standing back and feasting my eyes on this Aladdin’s cave!! Peter could see the excited look on my face and asked if I approved, rather I said dreamily. He then pulled open the drawers which contained a gorgeous selection of bras, panties, stockings, tights, dildos, butt plugs, a spanking paddle and other bdsm gear.
I asked him about the bdsm stuff as it was something, with the exception of being spanked by Andy, I had no experience of. He said that Jill was really into it and it turned her on to be the domineering woman in the relationship which he was ok with as he enjoyed it as well. He said we can try some tame bondage & spanking to start with and if I liked it we could try more ambitious things. I loved the way he described the various role plays and it was making me so horny I could scream with pure excitement!
Peter selected a black bra & matching lace panties, a suspender belt and stockings and left me to get changed which I did at super quick speed, relishing the feeling of being Nicole once again. My cock by this time was hard and the end just oozing a bit of precum which I tasted, mmm lovely!
I called for Peter and he returned only this time also wearing a similar outfit to mine but with white bra & panties and black stockings. The contrast between the white lingerie and his deeply tanned body was really erotic and a massive turn on, not that I needed any encouragement there!! I said wow you were as quick at getting changed as I was but he admitted he had been wearing them under his male clothes as had to get dressed quickly when the doorbell went otherwise he would have been changed into all male clothes. I told him I was so glad I was early otherwise we would not be standing together now dressed in lingerie! Fate works in strange ways indeed!
He kissed me deeply whilst his hands caressed my bum through the panties saying that he liked very much what he was feeling and I said likewise. By this time we were lying on the bed feeling other’s cocks (or clit as I started to think of mine as) whilst kissing and caressing. He asked if I was ok and I told him I felt I was getting near to orgasm which he said was ok as long as I could cum again which I said yes to. It’s really difficult to describe the emotions that were exploding within me and I was completely powerless to resist them even if I had wanted to which in my highly aroused state was nigh on impossible. By this time our panties were off and we got into a 69 with me on top, Peter’s cock was I guess about 8” uncut and stood like a rocket, I gently pulled down his foreskin and took him in my mouth, first licking and then swallowing him as far I could get without choking. Peter was doing the same to me but also licking my pussy-hole as well and the feeling was really intense. I rolled off Peter and he asked if he could fuck me, oh yes please you gorgeous man I cried and he got me into doggy position, put some lube on his fingers and started to finger me, first one finger, then two and finally three. He was really gentle and asked if was ok and he was ready to fuck ne if I was, I said could we call it making love instead of fucking and yes I was eager to feel his massive cock inside me. I use a butt plug a lot at home as really enjoy the sensation but my plug was nowhere near as thick as Peter’s cock so I asked him to be very gentle and slow. I could feel the tip of his shaft starting to push inside me and the feeling was wonderful. He pushed his cock a bit further into me and was whispering that I was the most gorgeous girl and that he wanted this to go on for ever. With a final push he was all the way inside me and I started to push back enjoying every second of being the girl. He started to thrust faster and I could hear his balls bouncing off my cheeks , this went on for a few mins then I could feel his cock swell inside me before with a cry he shot his spunk deep inside me. I thought he would pull straight out but he didn’t, instead leaving his twitching cock inside me whilst whispering romantic things in my ear. Finally with a squelch he pulled out and flipped me on to my back with him lying beside me propped up on his elbow. He asked me to clench my bum cheeks together as he wanted to lick the spunk out once he had his breath back! We lay like this for a while, kissing and cuddling each other. Peter asked if I wanted to cum yet and could he suck me and swallow if I did or would I prefer to fuck him. Without realizing it I had reverted back to Nicole mode and said if it was ok with him I would prefer to be the girl which he readily agreed to. He told me he had been waiting for a long time for someone like me to come along and that now he had found me he would make sure I was happy. I told him about my first time and how deeply I had felt for Andy and that me being the girl just felt right.
We had been cuddling and stroking each other and Peter took my soaking wet clitty in his mouth and very gently began to lick me whilst at the same time pulling my foreskin back, in no time at all I could feel an inferno starting within me and cried out I was cumming and I shot my massive load of creamy thick spunk into Peter’s mouth. It seemed to go on for ever, the spunk just pumping out until finally it stopped. Peter kissed me letting me swallow some of my own spunk which tasted lovely and creamy, yummy! We lay side by side for a while and Peter asked me to squat over his mouth which I gladly did letting his spunk flow out of my pussy and into his mouth. We kissed some more and Peter said let’s have a break and passed me a gown to put on before going downstairs.
I told him I couldn’t stay all day as had another appointment a few miles away in the afternoon but he told me he had a solution to keep my firm happy and wrote out a very large order promising me this was the start of a profitable relationship in more ways than one! I asked if I could borrow his ‘phone (this was before mobiles were in common use) and rang may 2.30pm appointment and asked if I could reschedule it because something unexpected had come up and they said not a problem. I next called the office to tell them that I had rearranged my afternoon appointment as my morning call was more complex than I was first led to believe so I could now concentrate on enjoying myself with Peter.
Whilst I was on the ‘phone Peter was sucking my clitty back to hardness so we returned back to the bedroom and lay back on the bed together. Peter was rock hard again and I asked him how many time he could cum in a day and he reckoned maybe 4 or even 5, wow I said that’s an awful lot of cream and could I have it all please to which he replied it’s all for you my gorgeous girl. It was quite uncanny how quickly we had accepted that he was the man & I the girl.
We talked about what turned us on apart from each other and found out we had a lot in common, I used to love dressing as a schoolgirl for Andy and Peter said it was a big fantasy for him to seduce one with a cock!! Well I said I’m here for the taking!! We got into a 69 again and Peter gave equal attention to my still wet pussy and now hard cock. He told me he was ready to make love again and this time I lay on my back with my legs over his shoulders. He entered me easily this time as my pussy was still soaking wet with his spunk and fucked me nice and slowly, nearly pulling out before pushing himself deep inside me. During this we were kissing, murmuring all sorts of soppy things to each other! Peter pulled out and lay beside me, I asked if everything was ok and he said yes but he was conscious that he seemed to be having all the fun so what would I like to do. He suggested maybe a bit of role play and I readily agreed thinking to myself all the time that I was incredibly lucky to have found such a lovely & considerate man as a lover.
We went back into the office room and looked through the various skirts etc and I said I would love to dress as a schoolgirl for him knowing it was a fantasy for him as he had mentioned it earlier.
He told me to pick my outfit out so I selected a grey pleated mini skirt, short sleeved white blouse and tie and some black shoes, however something was missing so I asked if he had any white knee length socks as that would make me a proper schoolgirl and unfortunately he hadn’t but said he would get some for next time. Having got dressed in my uniform (still wearing stockings & suspenders) I returned to the bedroom.
Peter instructed me to bend over the bed which I did, he then pulled my skirt up and started spanking me through my panties first quite gently but gradually getting harder and harder before he pulled my panties down to me knees and spanked me on my bare bottom. The spanking was quite hard by this time and was beginning to hurt so I whimpered and he stopped, bending down to first kiss my cheeks before sticking his tongue deep inside my pussy. The feeling was exquisite and was further enhanced by my cheeks which were stinging after the spanking! He stood up and I felt his cock beginning to enter me and without further ado he thrust his length into me and started to fuck me in long slow strokes, I could hear my pussy squelching like a wellington boot in mud and gradually his strokes became faster and faster before he cried out and shot his spunk deep inside me. This time he pulled out and started to lick my pussy whilst I started to wank myself off, I was getting close when Peter positioned me on my back and started sucking and licking me and I shot my load once again in his mouth and like last time he kissed me immediately after dribbling my spunk into my mouth which I received like a good little slut.
It was past lunchtime when we finally finished our lovemaking and went & had a shower together.
There is more to tell if anyone would like me to continue?
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