Trapped Sissy 2
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After I had finished at college, I started my first real job in an industrial town in the West Country. The Personnel department found me lodgings, and so I arrived on the Sunday afternoon at the house, which luckily was not far from the station as my suitcase was its usual over-loaded state.
I was greeted by a couple, Fred and Susan, and shown to my room, which it turned out had been their son’s until he had left home a year before to join the army.
I joined them at 7 for supper, and started to get to know them a bit better. Fred was probably about 40 or so, and what in those days we called a commercial traveller, in other words a travelling salesman for an engineering firm in the town, and he knew the company I was joining pretty well, having done his apprenticeship there when he had left school.
He and Susan had been schooldays sweethearts even though she had been several years his junior, and had married soon after he had qualified at 22, but they had only had the one c***d, quite soon, which seemed to sadden them as they talked about their early married life.
The conversation soon changed to a happier note as they asked about me, which with the candour of youth, I regaled them with for some time. As we finished supper, I asked if I could help clear away, but was firmly told that this was Susan’s job, and that seemed to be the end of the matter. Fred was, it seemed, away a lot, but when he was at home he ruled the house with a firm and ordered grip, making it very clear that they each had their own roles to play.
My first few months went very quickly, doing the programme that had been laid out for me, a very intensive training in a number of departments in the company, lasting for the next 12 months. I had expected to find a flat to share and not to stay in my lodgings, but I was comfortable and there seemed to be few restrictions, so there I stayed.
I saw little of Fred as he was away most of the week and I tended to travel up to London where most of my college friends were at weekends. As a result, it was not surprising that it was Susan whom I got to know rather better, and discovered that she was a very intelligent woman, with an interest in many things. She was anything but the person that she seemed to be when Fred was home. His presence seemed to create a set of rigid rules, which because of the time they had been together, Susan adopted immediately when he returned.
Fred was friendly, but there seemed to be a barrier there that was impenetrable to me, and I wondered if it was also as difficult for Susan. Still, they seemed content enough, though from my young age I had little real idea how people of their age would behave together with a paying guest in their house.
One evening we were talking, and I remarked that I was surprised that she had not worked after she was married, and she became a little tearful, saying that Fred wouldn’t hear of it. I passed her my hanky and put my arm round her shoulder in a friendly sort of way, not really knowing what else to do. She took it and blew her nose, but rather than passing it back to me, kept hold of it, and leaned into my arm. The moment passed, but after that I was conscious of some kind of change in our relationship.
It manifested itself in various ways, but was more of an attitude than any specific action, although I think overall Susan was less guarded in the things she would say, sometimes being critical of Fred, and then laughing and saying that she was glad he wasn’t here to hear her go on like this. I noticed as well, that when I would go down for breakfast, there were days when Susan wore her dressing gown and slippers, rather than being already dressed, as she was when Fred was home. It seemed as though she felt more relaxed with me, and to be honest I think I became more so as well.
One morning I woke early and went along the corridor to the bathroom, to hear noises from Fred and Susan’s bedroom. It sounded like whispering, though there may have been a groan or two as well, but the doors were thick and I couldn’t hear clearly, and wasn’t sure I should pry. I assumed that Fred had returned late the previous evening, but just then Susan emerged, wrapped tightly in her dressing gown, with rather a flushed face and was clearly a bit surprised to see me there.
She said something about early birds and not being able to sleep, and how lovely the sunshine was that morning, pointing to the garden through the window. That action caused her dressing gown to fall gape open, of which she seemed to be oblivious.
I was anything but oblivious as she revealed a lovely full breast, tipped by a puffy nipple, which caused an entirely natural reaction in me. Now it was I who started to flush, as suddenly she became aware of the bulge in my pyjama bottoms, and putting a hand to her mouth to stifle a giggle, said that she hadn’t had that effect on anyone for a long time.
I wasn’t sure how to respond to that so I simply said that if she went around showing such a lovely breast to horny young men, what could she really expect! At this she suddenly realised that her dressing gown was open, and somewhat flustered said, "Oh, I’m sorry."
"You shouldn’t be," I said, "your breast is lovely, and I’m sure you have another equally perfect."
"Obviously," she said, and rather coyly asked me if I would like to see it.
"Of course," I said, at which she took me by the hand and led me back into my room. Closing the door behind her, she dropped the dressing gown on the floor, revealing a body that I had hardly suspected under her usual dowdy clothes. I stammered and said, "But you are lovely....and yes, your other breast is as wonderful as the other."
"Come here, silly boy," she said, so I did, leaning down to meet her upturned lips, and feeling her warm body press into mine. "This has to be our secret," she said, "Fred doesn’t know I have such wicked thoughts, and ever since you came here, I have wanted to touch you." Saying this she did just that, her hand reaching down to encircle my erect penis, and to draw it out of my pyjamas.
"Oh, that is good," she said, and dropped to her knees, to start to suck me. I was glad that I had masturbated last night, looking at pictures in Playboy, else I think I would have cum almost as soon as her lips touched my cock. She worked on my cock in a way that I hadn’t experienced before, her tongue being so much more active than other women I had been with.
I think she sensed me getting close to cumming so slowed down, and told me that she was ready for me to fuck her, as she had already brought herself off earlier that morning.
"Ah," I said, "that was what I had heard earlier."
"Did you like the sounds?" she asked.
"I wasn’t sure what they were," I said truthfully.
"Come here, and you’ll hear them again, and more I hope, if you behave yourself."
She moved to the bed and laid down, her legs over the bed end. I approached her from the side, and she said, "No don’t be silly, that’s not where I want you," and raised her legs up, so it was obvious that she wanted me to stand at the end of the bed and fuck her vagina which was perfectly placed for me.
The pleasure of entering her was supreme, surprisingly tight, and as I slid my cock deep into her and started to build my speed, I realised that the position she had adopted made my cock stroke up the upper side of her vagina. She told me to do that more, as she was so sensitive right there.
I pushed my cock deeper into her and then almost pulled out, the feeling of her warmth around me so exquisite that I wanted this to last for ever, and continued to pump her hard. After all too few strokes, she tensed and started to shake as her orgasm spread through her body. The feeling of this on the length of my cock was wonderful, and after just a couple of fast strokes my cum was flooding her, though as soon as she realised I was ejaculating, she pushed me away and dived down to lick and suck the remnants of my sperm.
From that day on, whenever Fred was away on business, we slept together. I learnt that after their son was born, Fred had cut off marital relations for reasons that Susan couldn’t even now get him to explain. They had sort of drifted into a state of amiable companionship, but my arrival changed that, it seemed.
She hadn’t dared have an affair, in case someone in the town found out and said something to Fred, but had enjoyed herself when he was away, practicing masturbation almost every day, and she said, using various implements as dildos. She still had a lot of time to make up for, and seemed insatiable, demanding my cock every night and every morning before I went to work.
I was in heaven, and learnt more than I could have imagined about a woman’s body. I had been with a few women during my college days but in comparison those affairs were pale imitations of what now I learnt sex could be. She taught me control, and she taught me how to please her and how to tease her. There seemed to be no end to the delights she could bring me to experience.
Susan and I had been having sex together for a couple of months, and we had experimented with all the positions that we could think of, and kept trying to find new things to do. She seemed to enjoy my fingers stroking her anus, but she had never given me any encouragement to do anything else.
The subject of anal sex was one that I had obviously heard about, but never experienced. In my circle of male friends, it was regarded as a dirty thing that homosexual men did, or the very worst sluts allowed men to do, but that didn’t stop us thinking that it might be a good thing to try, if we ever found a woman willing to so it.
One night after we had finished a really heavy session which ended in me taking her doggy style, having a great view of her tight pink asshole, I decided to broach the subject of anal sex. She was a bit surprised, I could see, and said that she had always considered it as dirty and unnatural. As we talked further, I said that all I knew was that the talk in the rugby club was that some women did enjoy it, but how many and how, I didn’t know. She diverted our conversation by a quick dive down the bed to suck my cock hard again, so we didn’t progress the subject.
That was that for a while, until one day, a Wednesday remember for some reason, we had eaten supper, and were sitting in the living room, when she suddenly said, "You know our conversation about anal sex awhile back?"
I said, "Yes, and so?"
She said that she had gone to the library and looked at various books on anatomy and sexual practices, and that the talk in the rugby club seems to have been right, in certain cultures, anal sex is a common practice, and it seems to be quite highly regarded. So, she said, she had decided that she wanted to see what it was like, and that I was going to help her!
Of course I did, not without some apprehension, but what we did was very special and added another dimension to our secret life together. She took my hand after telling me that she had bathed while I was at work, so was clean, and told me how I was going to help her, and with the theory in my mind, we went upstairs.
There we undressed and started to cuddle, my fingers stroking her breasts and her nipples, all excited and standing out, as she snuggled into me, spooning, my cock hard but pressed against her bottom while she revelled in my attentions. I was stroking her pussy lips, and had just slid a couple of fingers into her moist and slippery vagina, when she twisted a little and this caused the lower two fingers of my hand to press against her asshole.
"Oh, you dirty girl," I whispered, as I concentrated more and more on that firm circle of muscle.
"I want to be dirty," she said, "and I want to get dirtier," her hand going to grip my penis and starting to stroke it. I moved my hand back to finger fuck her, with my thumb rubbing her clit as I did, until she came, and her juices covered my hand.
Kissing her deeply, I then started to stroke her asshole again, using her juices as lubrication, and after some time of stroking round and round, I ventured to press a fingertip into the little hole in the centre. She groaned at this, tensed slightly and then relaxed, and not just her body, it felt as though she had relaxed her anal sphincter, as my finger popped inside her. I held it still, partly surprised myself at the ease with which it entered, and partly so as not to do anything she might not like.
I need not have worried, as very soon after it was she who started to move, and feeling this, I also did, starting to slide my finger in and out of her asshole, up to the first joint, and then as she groaned for more, past the joint, the passage of which through her tight muscular rings made her groan again. I asked if all was well, and she whispered that it was bliss, and for me to carry on.
In those days, you couldn’t buy lubes as we can now, so Vaseline was the only easily available answer, and she had some handy, so I applied it to her asshole and my cock, and so one finger easily led to two, and I finger fucked her until I could see her asshole staying open as my fingers retracted. That was what she had told me to look for, so “Up now,” I said, and she obeyed, getting on to her hands and knees.
"Closer to the end," I said, and she moved to the end of the bed. I could see both her pussy and her asshole, and taking hold of my slippery cock, I positioned myself, pressing the end directly at the little hole in the centre of her asshole, and just teasing it round. With all the foreplay there, she was quite relaxed, and with little real pressure, I was able to push the head through.
It seemed to me that I should hold things there, but she didn’t want that and moved back onto me, so that my cock was hilt deep in her ass. It felt so hot, much hotter than being in her cunt, and she told me that she felt so full. As I had been told, I started slowly at first, and then as it became clear that she was starting to enjoy the sensation, I built my pace, her ass muscles gripping me and then relaxing, tighter around me that I had felt before, and it wasn’t long before I felt myself getting close.
She was close as well, as she started to make a deep guttural sound in her throat, followed by her body shaking in very hard orgasm. The sensation on my penis was just fantastic, and my balls emptied in record time into her anal cavity. Totally spent, I fell down upon her, and she collapsed as well, the two of us lying there, utterly exhausted.
After we had recovered, she said that she now understood what the books were talking about when they said that the anus had more nerve endings that the vagina. It was such a different type of orgasm, she felt she couldn’t handle that too often, but by the next night she seemed to have forgotten that. It seems to me now, looking back, that either every night over the next couple of weeks ended with anal intercourse, or else the joy of an anal awakening the next morning.
That is a real pleasure, and one I still enjoy greatly, the spooning together in the warmth and sleepiness of wakening, building into such sensations that waken and stimulate very nerve ending in our bodies.
Susan taught me not only about the basics and mechanics of sex, but also how to open my mind to accept the possibility of many other ways of giving and receiving sensual pleasure, and to rid myself of the normal constraints of intimate behaviour. She taught me that any part of the body, if properly stimulated, can give pleasure. She taught me to follow my instincts and to talk about my desires with my partners, and to work towards mutual pleasure. I am eternally grateful to her for all of this.
I left that town to move to London and said goodbye to a lovely older woman, whom I have never forgotten. I should have kept in touch, but never did, which is now something that I shall always regret.
I was greeted by a couple, Fred and Susan, and shown to my room, which it turned out had been their son’s until he had left home a year before to join the army.
I joined them at 7 for supper, and started to get to know them a bit better. Fred was probably about 40 or so, and what in those days we called a commercial traveller, in other words a travelling salesman for an engineering firm in the town, and he knew the company I was joining pretty well, having done his apprenticeship there when he had left school.
He and Susan had been schooldays sweethearts even though she had been several years his junior, and had married soon after he had qualified at 22, but they had only had the one c***d, quite soon, which seemed to sadden them as they talked about their early married life.
The conversation soon changed to a happier note as they asked about me, which with the candour of youth, I regaled them with for some time. As we finished supper, I asked if I could help clear away, but was firmly told that this was Susan’s job, and that seemed to be the end of the matter. Fred was, it seemed, away a lot, but when he was at home he ruled the house with a firm and ordered grip, making it very clear that they each had their own roles to play.
My first few months went very quickly, doing the programme that had been laid out for me, a very intensive training in a number of departments in the company, lasting for the next 12 months. I had expected to find a flat to share and not to stay in my lodgings, but I was comfortable and there seemed to be few restrictions, so there I stayed.
I saw little of Fred as he was away most of the week and I tended to travel up to London where most of my college friends were at weekends. As a result, it was not surprising that it was Susan whom I got to know rather better, and discovered that she was a very intelligent woman, with an interest in many things. She was anything but the person that she seemed to be when Fred was home. His presence seemed to create a set of rigid rules, which because of the time they had been together, Susan adopted immediately when he returned.
Fred was friendly, but there seemed to be a barrier there that was impenetrable to me, and I wondered if it was also as difficult for Susan. Still, they seemed content enough, though from my young age I had little real idea how people of their age would behave together with a paying guest in their house.
One evening we were talking, and I remarked that I was surprised that she had not worked after she was married, and she became a little tearful, saying that Fred wouldn’t hear of it. I passed her my hanky and put my arm round her shoulder in a friendly sort of way, not really knowing what else to do. She took it and blew her nose, but rather than passing it back to me, kept hold of it, and leaned into my arm. The moment passed, but after that I was conscious of some kind of change in our relationship.
It manifested itself in various ways, but was more of an attitude than any specific action, although I think overall Susan was less guarded in the things she would say, sometimes being critical of Fred, and then laughing and saying that she was glad he wasn’t here to hear her go on like this. I noticed as well, that when I would go down for breakfast, there were days when Susan wore her dressing gown and slippers, rather than being already dressed, as she was when Fred was home. It seemed as though she felt more relaxed with me, and to be honest I think I became more so as well.
One morning I woke early and went along the corridor to the bathroom, to hear noises from Fred and Susan’s bedroom. It sounded like whispering, though there may have been a groan or two as well, but the doors were thick and I couldn’t hear clearly, and wasn’t sure I should pry. I assumed that Fred had returned late the previous evening, but just then Susan emerged, wrapped tightly in her dressing gown, with rather a flushed face and was clearly a bit surprised to see me there.
She said something about early birds and not being able to sleep, and how lovely the sunshine was that morning, pointing to the garden through the window. That action caused her dressing gown to fall gape open, of which she seemed to be oblivious.
I was anything but oblivious as she revealed a lovely full breast, tipped by a puffy nipple, which caused an entirely natural reaction in me. Now it was I who started to flush, as suddenly she became aware of the bulge in my pyjama bottoms, and putting a hand to her mouth to stifle a giggle, said that she hadn’t had that effect on anyone for a long time.
I wasn’t sure how to respond to that so I simply said that if she went around showing such a lovely breast to horny young men, what could she really expect! At this she suddenly realised that her dressing gown was open, and somewhat flustered said, "Oh, I’m sorry."
"You shouldn’t be," I said, "your breast is lovely, and I’m sure you have another equally perfect."
"Obviously," she said, and rather coyly asked me if I would like to see it.
"Of course," I said, at which she took me by the hand and led me back into my room. Closing the door behind her, she dropped the dressing gown on the floor, revealing a body that I had hardly suspected under her usual dowdy clothes. I stammered and said, "But you are lovely....and yes, your other breast is as wonderful as the other."
"Come here, silly boy," she said, so I did, leaning down to meet her upturned lips, and feeling her warm body press into mine. "This has to be our secret," she said, "Fred doesn’t know I have such wicked thoughts, and ever since you came here, I have wanted to touch you." Saying this she did just that, her hand reaching down to encircle my erect penis, and to draw it out of my pyjamas.
"Oh, that is good," she said, and dropped to her knees, to start to suck me. I was glad that I had masturbated last night, looking at pictures in Playboy, else I think I would have cum almost as soon as her lips touched my cock. She worked on my cock in a way that I hadn’t experienced before, her tongue being so much more active than other women I had been with.
I think she sensed me getting close to cumming so slowed down, and told me that she was ready for me to fuck her, as she had already brought herself off earlier that morning.
"Ah," I said, "that was what I had heard earlier."
"Did you like the sounds?" she asked.
"I wasn’t sure what they were," I said truthfully.
"Come here, and you’ll hear them again, and more I hope, if you behave yourself."
She moved to the bed and laid down, her legs over the bed end. I approached her from the side, and she said, "No don’t be silly, that’s not where I want you," and raised her legs up, so it was obvious that she wanted me to stand at the end of the bed and fuck her vagina which was perfectly placed for me.
The pleasure of entering her was supreme, surprisingly tight, and as I slid my cock deep into her and started to build my speed, I realised that the position she had adopted made my cock stroke up the upper side of her vagina. She told me to do that more, as she was so sensitive right there.
I pushed my cock deeper into her and then almost pulled out, the feeling of her warmth around me so exquisite that I wanted this to last for ever, and continued to pump her hard. After all too few strokes, she tensed and started to shake as her orgasm spread through her body. The feeling of this on the length of my cock was wonderful, and after just a couple of fast strokes my cum was flooding her, though as soon as she realised I was ejaculating, she pushed me away and dived down to lick and suck the remnants of my sperm.
From that day on, whenever Fred was away on business, we slept together. I learnt that after their son was born, Fred had cut off marital relations for reasons that Susan couldn’t even now get him to explain. They had sort of drifted into a state of amiable companionship, but my arrival changed that, it seemed.
She hadn’t dared have an affair, in case someone in the town found out and said something to Fred, but had enjoyed herself when he was away, practicing masturbation almost every day, and she said, using various implements as dildos. She still had a lot of time to make up for, and seemed insatiable, demanding my cock every night and every morning before I went to work.
I was in heaven, and learnt more than I could have imagined about a woman’s body. I had been with a few women during my college days but in comparison those affairs were pale imitations of what now I learnt sex could be. She taught me control, and she taught me how to please her and how to tease her. There seemed to be no end to the delights she could bring me to experience.
Susan and I had been having sex together for a couple of months, and we had experimented with all the positions that we could think of, and kept trying to find new things to do. She seemed to enjoy my fingers stroking her anus, but she had never given me any encouragement to do anything else.
The subject of anal sex was one that I had obviously heard about, but never experienced. In my circle of male friends, it was regarded as a dirty thing that homosexual men did, or the very worst sluts allowed men to do, but that didn’t stop us thinking that it might be a good thing to try, if we ever found a woman willing to so it.
One night after we had finished a really heavy session which ended in me taking her doggy style, having a great view of her tight pink asshole, I decided to broach the subject of anal sex. She was a bit surprised, I could see, and said that she had always considered it as dirty and unnatural. As we talked further, I said that all I knew was that the talk in the rugby club was that some women did enjoy it, but how many and how, I didn’t know. She diverted our conversation by a quick dive down the bed to suck my cock hard again, so we didn’t progress the subject.
That was that for a while, until one day, a Wednesday remember for some reason, we had eaten supper, and were sitting in the living room, when she suddenly said, "You know our conversation about anal sex awhile back?"
I said, "Yes, and so?"
She said that she had gone to the library and looked at various books on anatomy and sexual practices, and that the talk in the rugby club seems to have been right, in certain cultures, anal sex is a common practice, and it seems to be quite highly regarded. So, she said, she had decided that she wanted to see what it was like, and that I was going to help her!
Of course I did, not without some apprehension, but what we did was very special and added another dimension to our secret life together. She took my hand after telling me that she had bathed while I was at work, so was clean, and told me how I was going to help her, and with the theory in my mind, we went upstairs.
There we undressed and started to cuddle, my fingers stroking her breasts and her nipples, all excited and standing out, as she snuggled into me, spooning, my cock hard but pressed against her bottom while she revelled in my attentions. I was stroking her pussy lips, and had just slid a couple of fingers into her moist and slippery vagina, when she twisted a little and this caused the lower two fingers of my hand to press against her asshole.
"Oh, you dirty girl," I whispered, as I concentrated more and more on that firm circle of muscle.
"I want to be dirty," she said, "and I want to get dirtier," her hand going to grip my penis and starting to stroke it. I moved my hand back to finger fuck her, with my thumb rubbing her clit as I did, until she came, and her juices covered my hand.
Kissing her deeply, I then started to stroke her asshole again, using her juices as lubrication, and after some time of stroking round and round, I ventured to press a fingertip into the little hole in the centre. She groaned at this, tensed slightly and then relaxed, and not just her body, it felt as though she had relaxed her anal sphincter, as my finger popped inside her. I held it still, partly surprised myself at the ease with which it entered, and partly so as not to do anything she might not like.
I need not have worried, as very soon after it was she who started to move, and feeling this, I also did, starting to slide my finger in and out of her asshole, up to the first joint, and then as she groaned for more, past the joint, the passage of which through her tight muscular rings made her groan again. I asked if all was well, and she whispered that it was bliss, and for me to carry on.
In those days, you couldn’t buy lubes as we can now, so Vaseline was the only easily available answer, and she had some handy, so I applied it to her asshole and my cock, and so one finger easily led to two, and I finger fucked her until I could see her asshole staying open as my fingers retracted. That was what she had told me to look for, so “Up now,” I said, and she obeyed, getting on to her hands and knees.
"Closer to the end," I said, and she moved to the end of the bed. I could see both her pussy and her asshole, and taking hold of my slippery cock, I positioned myself, pressing the end directly at the little hole in the centre of her asshole, and just teasing it round. With all the foreplay there, she was quite relaxed, and with little real pressure, I was able to push the head through.
It seemed to me that I should hold things there, but she didn’t want that and moved back onto me, so that my cock was hilt deep in her ass. It felt so hot, much hotter than being in her cunt, and she told me that she felt so full. As I had been told, I started slowly at first, and then as it became clear that she was starting to enjoy the sensation, I built my pace, her ass muscles gripping me and then relaxing, tighter around me that I had felt before, and it wasn’t long before I felt myself getting close.
She was close as well, as she started to make a deep guttural sound in her throat, followed by her body shaking in very hard orgasm. The sensation on my penis was just fantastic, and my balls emptied in record time into her anal cavity. Totally spent, I fell down upon her, and she collapsed as well, the two of us lying there, utterly exhausted.
After we had recovered, she said that she now understood what the books were talking about when they said that the anus had more nerve endings that the vagina. It was such a different type of orgasm, she felt she couldn’t handle that too often, but by the next night she seemed to have forgotten that. It seems to me now, looking back, that either every night over the next couple of weeks ended with anal intercourse, or else the joy of an anal awakening the next morning.
That is a real pleasure, and one I still enjoy greatly, the spooning together in the warmth and sleepiness of wakening, building into such sensations that waken and stimulate very nerve ending in our bodies.
Susan taught me not only about the basics and mechanics of sex, but also how to open my mind to accept the possibility of many other ways of giving and receiving sensual pleasure, and to rid myself of the normal constraints of intimate behaviour. She taught me that any part of the body, if properly stimulated, can give pleasure. She taught me to follow my instincts and to talk about my desires with my partners, and to work towards mutual pleasure. I am eternally grateful to her for all of this.
I left that town to move to London and said goodbye to a lovely older woman, whom I have never forgotten. I should have kept in touch, but never did, which is now something that I shall always regret.
Geraldine
- 06.01.2022
- 6
- 0
