Jennifer's Journey: Becoming The Perfect Wife -- Part 1 free porn video

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Jennifer's Journey: Becoming the Perfect Wife - Part 1 By Jennifer Madison Introduction This isn't one of those stories where a husband gets tricked into wearing his wife's panties only to learn that it secretly excites him. There's no magic or sorcery either. This is the true story of discovery of who I really am and about the lovely woman who guided me on this journey. Was this journey entirely voluntary or was I coerced? Had I known where this journey would take me, would I have so willingly gone along? Did I subconsciously desire to be transformed into what I have become? To this day, I don't know the answers to these questions. I am a lifelong sissy who has always enjoyed to sensations of looking and acting and feeling like a woman. And my lovely wife knows this. She has always known of my secret desires and for years we had found fun ways to incorporate this into our relationship. But what started out as fun and games took a decidedly more serious turn about two years ago. But before we get to that, a little bit more about my wife and me. My "real" name is John and my wife's name is Sarah. We are both in our late thirties and have been married for over ten years. Since graduating from college, we have managed to stack away quite a bit of money, especially considering that we're really not that old. I made a lot working in high tech and my wife did very well as a stock broker. On top of our incomes we made some really good investments along the way. Two years ago, at the age of 37, I officially retired and these days my wife works a very limited and flexible schedule. Sarah, who is a strikingly beautiful Asian woman, has always treated my female alter ego, Jenny, with great tenderness and care. She understands that Jenny is very much a part of my personality. And while I've have always tried to portray a fairly masculine image when out in the real world, the truth is I'm just not very manly. I'm skinny, I'm not very strong, my skin is very fair, and frankly, below the waist I don't have much to brag about. Nonetheless, Sarah always seemed to love and care for me - although I never forgot for a single minute that a beauty like her could have any man she wanted. My New Goal As I said, I retired a couple of years ago. This gave me plenty of time to relax and putter around the house in ways that I had been too busy to do before. And of course, this gave me plenty of time to enjoy being Jenny. On a typical day, I would get up early, maybe 6:00, and shower and shave and get ready for the day. Ever since I stopped working I've been keeping my whole body shaved and smooth. Assuming that there was no need for me to go out (and there rarely was), I might put on some light make-up, a nice outfit, some jewelry and perfume and be Jenny for the day. Typically a simple blouse and skirt (over my lacy underthings of course) would do the trick. Or else maybe a silky ladies t-shirt over capris - things like that. I would go downstairs and make breakfast for Sarah and bring it to her in bed around 7:30 or so. We would then chat for a while, her still in bed, me in a chair beside her. We would discuss our plans for the day. She would often have chores around the house that she wanted me to do, which was fine since I wasn't working any more. She would often go out for part of the day, either to work or to go to the gym or to meet up with friends. I typically found that the day flew by - between doing some chores and watching a few soap operas -- a bad habit I developed since I stopped working. I would always plan a nice dinner for the two of us, and I would usually change into something a little more dressy and spice up my make-up a bit. To make it special, most nights I would set the table in the dining room with a table cloth and candles and a bottle of wine. After dinner, we'd watch TV in bed and chat some more before drifting off to sleep, my in my nightie and Sarah in her flannel pjs. Anyway, I was truly enjoying the simple pleasures of being retired, having time to be Jenny and having a supportive wife who didn't seem to mind. I still remember the night. It was two years ago last September, a couple of months after I stopped working and started spending most of my days as Jenny. Sarah and I were curled up in bed, her arm draped over my satin clad body, and she said, "Jenny, it's been so nice having you around so much. And dinner was just so lovely tonight. You are becoming quite the wonderful little housewife." I shuddered with both excitement and with the sudden realization that she was right. I was becoming the housewife to a sexy, successful, exotic beauty. And she enjoyed it. "But you know Jenny," she continued, "I worry about you a little. You spend your days here all alone and that can't be healthy. I was also thinking that since you seem to have decided that being a housewife is what you want to do, I think that together we can make you into simply the very best little housewife you can be. Would you like that?" she asked. My head was spinning. "Well, yes," I responded. "If that's what you would like." "I would like that very much," Sarah said. "I have some ideas that we can get started with right away. I love you, Jenny. You're going to make me so proud." And with that she gave my bottom a little squeeze and kissed me good night. Let me tell you, I was up for hours that night! Saturday Morning Not much more was said about my becoming a better housewife for a couple of days. I was beginning to think that maybe Sarah was just making conversation. But on Saturday morning, over breakfast of Eggs Benedict that I prepared and that we ate in our sun room, Sarah started to share with me her plans. And as is typical for Sarah, she had everything thought through. "Jen, the way I see it, there are a few areas that I want you to focus on. First, is your appearance," she started. I was suddenly feeling very self- conscious. I started tugging at the hem of the sleeveless cotton dress I was wearing, and staring down at my stockinged legs and my sandals with the little heels. My wife, of course, was wearing jeans and a sweatshirt. She sensed what I was feeling and quickly continued, "Don't get me wrong. I think you look very nice. But I do have some ideas. First, I would like you to lose 10 pounds." "Ten pounds?" I thought. Jeez, I thought I was pretty skinny to begin with. I would be really slim if I lost 10 pounds. "We'll start you on your new diet today. If we don't make good progress quickly, then we'll enroll you at Jenny Craig and that should do the trick." Sarah continued, "And you need to get some exercise. I would like to you to start joining me at my Tuesday and Thursday morning Aerobics classes. You can come in your boy clothes." "Now for other aspects of your appearance, I think we need some professional help. I made some calls and found a salon that was very interested in having Jenny as a client." Sarah continued. "You mean you told them all about Jenny - including her...secret?" I asked. My mouth was completely dry and I was beginning to get a bit dizzy just thinking about where all this was going. "Oh yes, I told them all about you and they are thrilled. I have arranged a weekly appointment for Jenny with them every Thursday afternoon. We will decide what you'll have done each week - manicures, pedicures, facials, waxing, that sort of stuff. They also sell and style wigs." she explained excitedly. My head started spinning. I was equally thrilled and terrified by her plans. I couldn't believe what I was hearing. Is this really what she wanted? Is this really what she wanted me to become? I composed myself and said, "Wow - that's a lot. You really planned this all out, didn't you." "Jenny," Sarah replied, looking at me piercingly, "I'm just getting starting. Your appearance is just one of the things I want you to focus on. Now I want to talk to you about certain skills." "Skills?" I asked. "What kind of skills?" "To be specific, I've enrolled you in a sewing class and a cooking class at the YWCA two towns over. These classes are right after our Aerobics class, so you'll already be out and about on those days. On Tuesdays, you'll be home around lunch time, so you'll still have plenty of time to change out of your boy clothes and be Jenny again if you want. On Thursdays you can go straight to the salon after cooking class." "Sewing and cooking at the YWCA?!!" I exclaimed. "But I'll be the only guy there. Besides, I'm not sure I want to take sewing and cooking classes." "I want you to take these classes," she replied sternly. "If you're going to be the housewife, I expect you to put your heart into it. I've shown incredible patience and kindness to you, Jennifer. I expect you to return the favor by being supportive of this plan." "I...I...I'm sorry", I stammered. "You're right. You've been nothing but kind to me. I will try to be open minded about this. I'll do my best. I promise." "I'm sure you will." She replied matter of factly. "Let me continue. We're going to work together on some other aspects of housework that I think you can improve on. Ironing for one. But we'll work on that over time." Sarah continued. "The third area of focus is going to be social. Like I said, you spend too much time alone. I think the exercise classes, the cooking and sewing classes, and the weekly salon appointments will help, but I think there's more we need to do. I think you and I should plan to get out together, as girls, at least once a week. We can drive a few miles away from here and no one will know us. Would you like that?" she asked. "Oh yes, Sarah, very much." I replied. My breathing was quickening from the excitement of what I was hearing. "Good. We'll plan to go out on Thursday evenings, when you're done with your salon appointments. Also, I've also arranged for us to have a weekly massage, here at the house. Again, I've made all the arrangements. Jenny, you will simply love getting a massage every week." "You mean, I will be dressed as Jenny, and a person will come to the house and give us both massages?" "That's right, girl," Sarah replied. "It will be great." "Sarah," I asked, "Why do you want to do all of this?" Sarah replied, "I want to do this for the both of us. You may not be able to admit it, but I know, down deep, this is what you want too." Jenny's New Schedule And so, just as Sarah described it, I was on a new schedule. Sarah was expecting a lot from me and I didn't want to disappoint her. For about three-quarters of my week, I was living as Jenny. Life quickly settled into a pattern, and while I never bargained for any of this, I must admit that I was living out my most incredible dreams. I was becoming the loyal, dedicated - and increasingly attractive - housewife to my sexy wife. Sarah planned my daily schedule and chores. She also made quite a few changes to my wardrobe. My daily attire of simple tops and skirts or capris was slowly being replaced by new things Sarah was buying for me. Increasingly I was put into white or pastel tops that were cuter and lacier, often with little cap sleeves or a poofy short sleeve. Some of the tops had pretty ribbon details. My skirts were fuller, swingier. Some days I wore dresses, typically sleeveless or with short sleeves. Most of my dresses fell slightly below my knees and were nicely fitted, with princess seams or darts, and some with skinny belts that I could cinch in tight around my waist. On my feet, Sarah might pick out sandals or pumps with a small heel, or else sometimes ballet flats. I wasn't so dressed up to be comical or outrageous, but I was certainly more dressed up than most other housewives. I could see Sarah was less interested in turning me into another soccer mom - and more interested in turning me into June Cleaver. And I loved it! Every time I passed a mirror in our house as I went about my daily chores, I would stop and gasp and admire myself. I would think, as I smoothed out my skirt or fix my hair in the mirror, how lucky I was to have found such an understanding woman who seemed to know my deepest desires better than I did. Now at this time, my hair had grown out pretty well - it was kind of shaggy and pretty long. But I could never get it to grow out thick and long enough that it looked truly glamorous. And besides, I was still going out in public as a boy pretty often. So I settled for living with my own hair when I was around the house, and with some work it really didn't look bad. But for going out purposes -- or if I simply wanted to look my best for Sarah -- I would sometimes pin on a wig. I was really pretty happy with how I looked. I certainly wasn't a true beauty, but I was almost passable (and very passable under the right conditions). And the dieting really did pay off. I lost a couple of pounds each week so there was no need to go to Jenny Craig. I even lost more than 10 pounds in the end, and Sarah was right - it did improve my appearance. My shoulders and arms looked a bit more slender and my legs looked a bit leaner (although I have to admit, my legs have always looked great). I took better care of my skin by copying Sarah's nighttime routine and my complexion looked smoother and clearer. I was taking better care of my hands and feet too. Overall, I was, day-by-day, becoming softer and more delicate in ways that pleased me very much. And so by the end of September, I was starting to live as Jenny - pretty much full time from Thursday afternoons until early Tuesday mornings. The more time I spent as Jenny, the more natural I felt as Jenny and the more Jenny's personality was able to shine through as it had never been permitted to before. Tuesday afternoons and Wednesdays were usually spent in boy clothes, as I would sometimes use this time if I needed to run errands outside the house or do some chore in the yard. Although over time, this too would change. So Fridays through Mondays - four days a week -- I would rise early and get my self cleaned up and dressed. (Sarah would usually suggest what I should wear the next day as we lay in bed the night before). Over breakfast, Sarah would list out the chores she wanted done for the day and to let me know her schedule. Sarah was usually out of the house for at least several hours a day - and was rarely home at lunch time. As I said, she still worked and enjoyed it, although her schedule was very flexible. As soon as the breakfast things were cleaned up and put away, I would get busy on my chores, such as the laundry and vacuuming and dusting. I got better at ironing over time with some help from Sarah and soon I was spending a lot of time ironing her clothes. My chores included paying bills, so about 2 days a week I spent some time in Sarah's home office taking care of bills or balancing the check book. I call it Sarah's office as I had really given up use of our home office to Sarah after I stopped working. In the middle of the day, I would make myself something light to eat, always being careful to stick to my diet. I might take a break during the day to watch some TV or read a magazine -- Allure has become my favorite. By mid-afternoon, it was time to start planning for Sarah's dinner. Anything that needed a lot of time to prepare I would start on right away. Then by 4:00 or 4:30, it was back to the bathroom to fix myself up. After a long day of chores, I would need another shower and would have to redo my make-up. Still in my robe, I would get most of the rest of the dinner preparations taken care of, like setting the table, getting the wine out of the cellar and making the salads. By 5:30 or 6:00 or so, I would change into my outfit for dinner. It became very important to me to look my best for Sarah each evening - and I worked hard at it. When I finally came down the stairs each evening for dinner, Sarah would usually be in the living room reading the paper and waiting for me to emerge. My heart would swell to near bursting when she would stand-up as I came down the stairs and rush to give me a big hug (no kissing on account of my make-up). She would shower me with compliments about how beautiful I looked, how nice I smelled, or how pretty my outfit was. She would often make me twirl around in the living room for her so she could take in the whole effect, especially if I was wearing something new that Sarah had gotten for me -- which was really pretty often at this point. My typical dinner outfit might include a little black cocktail dress, some pearls, smoky black stockings and sexy high heeled sling backs. The compliments and hugging would continue for several more minutes until we finally sat down for dinner. About once a week I would enter the dining room to see that Sarah had bought flowers for me! I would serve up dinner and I conversation turned simple and conventional. We talked about our respective days, the news, that sort of thing. I would sometimes serve Sarah dessert and an after-dinner drink in the living room. There, sitting on the couch, with a little alcohol and a good meal in us, we would often start making out like teenagers. Sarah would whisper sweet and sexy things into my ears while nibbling on my neck and running her hands all over my body. Things would heat up until it became clear that we better get to the bedroom in a hurry. Upstairs, I would quickly change out of dinner dress and into a very pretty nightgown or teddy (I had loads of them). Sarah would usually strip down to her undies. And then we would make love. In my new role, it was understood that Sarah would take the lead in bed, and I was perfectly fine with that. Whatever she wanted, I was more that happy to comply with. After much foreplay -- often with me orally serving her for a little while -- Sarah would tell me it was time to put on a condom (condoms were so much neater Sarah explained). She would roll me onto my back, lift up my nightie, straddle me, and slip my little "Princess" (that's what Sarah liked to call it) inside of her. Soon she would shift around so that her legs were between mine, allowing me to wrap my legs around her waist. Sarah would bring her knees up a bit so that she was almost kneeling between my legs. As she started to get more excited, I needed to fight any urge to release too soon. It was important that I perform well and long enough for my loving and deserving wife. Often I would feel her fingers work their way down to massage her clitty while she fucked me. I would feel the tips of her long nails scraping the base of my little "Princess". As she got more worked up Sarah would moan and start talking to me as she stared down into my eyes. "You like being fucked by me, don't you Jennifer? You love having your legs wrapped around me and having me fuck you, don't you?" "Oh yes, Sarah, I do. I love being fucked by you." I would whimper in response. "Oh you are so hot, Jenny," Sarah would continue. "You are so sexy. I love feeling your silky smooth legs around me. I love having your little "Princess" deep inside of me. I love having my own little housewife to fuck whenever I want. That's what you are, isn't it. My own little housewife, my own little fuck toy?" "Oh yes, Sarah. That's what I am. I love being your housewife. I am your little fuck toy. I would do anything for you Sarah, anything," I replied breathlessly. And with that, Sarah would press her lips hard against mine and thrust her tongue deep inside my mouth. She moved her hand away from her clitty and grabbed both of my soft, manicured hands in hers and held them down on either side of my head, pinning me to the bed. Sarah's body would shake as she climaxed. This was my signal to release as well and I exploded inside her. Our combined orgasms seemed to go on for minutes. After a while, Sarah would begin breathing normally again and come back down to earth. She would smile at me and tell me how much she loves me. I would of course tell her the same and tell her how lucky I felt to be married to such an incredible woman. Sarah said she felt the same way about me! Things to Learn As you recall, Sarah had insisted that I take some classes, both to improve my skills as a housewife, but also to get me out of the house a bit each week. And in the end, the gym classes and even the cooking and sewing classes weren't too bad. The Aerobics classes were kind of fun, even though I was the only guy there. And it really paid off. Combined with the dieting, the exercise made my tummy flatter and I think my butt looks nicer too. To the gym I would wear light-weight sweat pants and a long sleeve t-shirt because I don't like people seeing that my arms and legs are hairless. The bad part is that I have to take a shower in the Men's locker room at the gym because I go straight to other classes right after Aerobics. Fortunately, the Men's locker room is pretty dead most weekday mornings, but sometimes there are other men there. Most of the time, I can figure out some way to avoid letting the other men see that there is a hairless, silky-smooth- skinned sissy in the locker room. (One time I had neglected to remove my bright red toe nail polish and didn't realize that there were other men in the locker room who could see my feet beneath the curtain as I took my shower - but that's another story). While I didn't mind being the only male in Aerobics, sewing and cooking classes were a bit more awkward, due in part to fact that I went to these classes alone, without Sarah. I could tell that most of the other ladies felt I didn't belong (after all, these were courses at the YWCA). Nonetheless, I took the lessons seriously and I think I learned a lot. Sarah always complemented me on the foods I had prepared that I brought home from cooking class. And I even made a skirt for Sarah in the sewing class. That was all the easy part. Then there was the salon. Let me first say that ever since Sarah put Jenny on this new program, she's been driving me around a lot. We have two cars, but these days she seems to like shuttling me where I need to go. After Aerobics (which we go to together anyway), she waits for me to come out of the locker room. Then she drops me off for cooking or sewing class. She comes back 90 minutes later, either to take me home (on Tuesdays) or to take me to the salon after stopping for a light lunch together on Thursdays. Although we never talked about it, I think there are two reasons why she likes to shuttle me around: First, it ensures that I really go to the commitments Sarah has made for me. And second, it is one more way that Sarah can use to make me increasingly dependent on her and to emphasize to me that I am no longer the free and self-reliant man I once might have been. Anyway, after sewing class on Thursday, Sarah would drive me over to the salon for what would typically be a 3 hour session! Upon my arrival, I would be sent into the back room. Fortunately, I was almost always treated in the private area in back, not in the big rooms out front with all the other ladies. I would change out of the boy clothes I wore to sewing class and into a light robe the salon provides wearing nothing else but my panties. While I was changing, Sarah would discuss the afternoon's treatments with Denise, the salon owner who had expressed delight to Sarah in having me become both a regular customer and a project. As I was led away to start my first treatment of the day, Sarah would retrieve a garment bag from the car and leave it in the salon office where she would collect my boy clothes that had been left in a bag there. Obviously, I would go into the salon each Thursday a boy and have to come out dresssed as a girl to match the rest of my look. A typical afternoon at the salon would start with a waxing session. I have been waxed repeatedly - all over my body (yes - I mean all over). As a result, the hair on my body seems to be growing in more slowly and finer than before. Then, typically a facial, or sometimes another treatment like a body wrap or a parafin treatment. Then it was onto the manicure/pedicure. Depending on what Sarah asked for, sometimes this was a fairly simple affair, although often she would have requested nail wraps for me, giving me, at least temporarily, long, sexy nails. Very quickly I realized I wasn't just Denise's project. I had become the pet project of the entire salon staff. Over time I got to know all the girls who worked there, each taking turns with her specialty with me. Each visit would include some work with either my own hair or with one of my wigs. My natural hair has been given a pretty, layered cut -- the best they could do with what I have. It's now got pretty auburn highlights. The style and highlights are both subtle enough that I can still be out dressed as a guy, but with a little fluffing and styling, it looks pretty girlish. And after a visit to the salon and some professional attention, my own hair could look really pretty. The last step of each visit was make-up and Denise almost always did this herself. This was part make-over and part instruction. I would pay careful attention to her lessons and then practice each new technique or with each new product the following week. After the salon girls were done with me, I retrieved my garment bag from the office and changed in an unused treatment room. I was always anxious to see what outfit Sarah had picked out for me to change into because I never had any idea what she packed. And seeing the outfit Sarah picked would give an indication of where the rest of the evening would go (of course the salon girls knew everything, but wouldn't share a bit with me). A simple outfit, like slacks or capris or a denim skirt might indicate that after the salon, Sarah would take me to the movies or maybe an evening in the park which we enjoyed several times before the winter started. Something dressier would usually mean that we were heading out for dinner. On these occasions, the salon girls would generally been instructed to give me a more glamorous look and to style and pin on one of my wigs for the evening. Sarah and I had a found a restaurant that we could feel very comfortable at and it soon became our favorite destination on Thursday nights. So while my hours in the salon were sometimes painful, sometimes tedious and almost always a bit embarrassing (because the girls at the salon would make such a fuss over me), it was all worth it. Sarah would squeal with delight upon seeing me emerge fully dressed and fully made-up. I would be greeted with an enormous hug and praise. Sometimes she would claim not to have found parking out back so we would exit through the front of the shop past all the other lady customers and have to walk some distance down the sidewalk to where Sarah had parked. So for my many hours in the salon, not only did I get one night a week where I looked absolutely super and make Sarah so happy with me, but my overall look improved a lot over time with the repeated treatments and instruction. And so my new life began to take shape. Gratefully following the path my wife picked out for me, I began to transform into the very model of a perfect housewife. I worked very hard to please my loving and deserving wife, to make her life at home just the very best it could be. I worked to look my best so that she would be proud to be out with me. As my feminine being bloomed, I found I was ever more dependent on Sarah for everything - for making decisions, planning my days, setting my diet, deciding what I would wear. I felt my old self slipping away. I also found that I lived for Sarah's compliments. My hours of work in straightening the house or making a meal or prettying myself for her were all worth it when she would show her appreciation and affection. My life was becoming more fulfilling by the day, knowing that I was becoming the housewife that my lovely wife deserved.

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Jennifer's Journey - Becoming the Perfect Housewife, Part 16 I took full advantage of Sarah's absence for the rest of the weekend, using my time alone to think about my decision to make my life as Jennifer more permanent and more complete. The more I thought about it, the more certain I was that this was the right thing to do. I was tiring of the fantasy of being Jenny - and excited about the idea of letting Jenny become a real person. Sarah returned on Sunday evening. She said...

2 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 14

Jennifer's Journey - Becoming the Perfect Housewife, Part 14 My Sister's Phone Call The week following my birthday party - the fourth week of March - was certainly memorable. The phone was ringing when Sarah and I arrived home after driving back together from our Sunday night "dates" at our boyfriends' houses. It was Caitlin. She was wasting no time converting Friday night's 'one night stand' into a full blown affair. After repeatedly saying how much fun she had at my party, she...

2 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 5

Jennifer's Journey - Becoming the Perfect Housewife, Part 5 January had been a busy and exciting month for me in my new life as Jennifer. I started to develop a bit more of a life outside the house and independent of Sarah. As Jennifer, I was enjoying my therapy sessions and spending time with my new friend Vicki. But there was one more, big, new experience for Jennifer that would make January an unforgettable month. Friday Massages From the very beginning, Sarah had suggested...

4 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 8

Jennifer's Journey - Becoming the Perfect Housewife, Part 8 Two Calls on A Tuesday Night Sarah and I were spending a quiet evening at home on Tuesday. We had enjoyed a nice dinner together and I had finished cleaning up the dishes. The two of us were sitting at the table in the bedroom where I usually serve Sarah her breakfast while I did Sarah's nails. The phone rang. "Bear a dear and get that, would you?" Sarah said, wiggling her wet nails to demonstrate that she was...

1 year ago
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Jennifers Threesome

You see my wife Jennifer is a great looking lady despite our middle ages, of course age takes it toil but she holds her age wonderful and the guys still look her way when she walks by. With her 40dd tits and long legs and dressing slutty. We have been going to a local nightclub/pub for a few months for dancing and drinking. The people seem to know us and we seem to attract new friends, male and female. One night Jennifer had gotten really bad drunk and was having a great time.. Let me say that...

Cheating Wifes
4 years ago
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My wife becoming a hotwife 1

My wife becoming a hotwifeMarie's journey from housewife to hotwifeThis is a true story about my shy demure wife's journey into exhibitionism and into being shared.I am Eugene and my wife is Marie. This a true story about her journey from a woman who would never even think about cheating, to the role of my hotwife and on to slutwife. She was 5'4"and tipped the scale at about 135 but she carried it well. Her best assets were her 38D tits with very prominent dark nipples which she always tried to...

3 years ago
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Jennifers Need

This is a continuation of the story in Jennifer’s Shame, so if you’ve not already read it, I suggest you start there. As always, all comments and scores are gratefully received. When she got home, Jennifer went upstairs and ran a bath. Easing herself gently into the warm water, she lay back, closed her eyes and let her mind drift back over the events of the afternoon. She could almost hear the sound of the swishing cane and again experienced the searing sting as the rattan bit into the soft...

1 year ago
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Jennifers Shame

At the age of 37, Jennifer Carson still had it. Her face was unlined and she was fitter than she had ever been in her life. Appraising her naked body in the mirror, she allowed herself a small smile of satisfaction. Her breasts were still pert and her bottom was round and smooth. On this sunny Monday morning, she would be visiting her old secondary school to appraise its current standards and decide if she was going to send her own daughter there. 20 years ago it had been a great place and...

2 years ago
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Jennifers Eggnog

The first shot struck Jennifer under the chin. That one came from Lawrence. She was still yelping when Trent’s delivery took her full in the face, filling her mouth and blinding her in an explosion of thick white. She spat and wiped her eyes clear, then pursued her boyfriend, scooping snow as she ran. Trent taunted as he fled, but stumbled knee-deep in a drift. “Bastard!” She laughed as she pelted him, then pushed him over while he was still off-balance. He pulled her with him and they rolled...

2 years ago
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Jennifers Story

Jennifer's Story by Marci Manseau Gail - Part One My dad died of a heart attack when I was a infant. Unfortunately, I never really got to know him. All I had left was a few pictures of him and my mother's reminiscences. Growing up without a father was difficult, so when my mother remarried, I was as delighted as she was to finally have a man around. Actually, two men. My new father's name was Jack and he had a son named Bernie who moved in with us just after the wedding. ...

3 years ago
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Wifes journey to becoming a slut

I have several stories relating to this journey so will start at the beginning.My name is Bill and her name is Debbie.We were young married and both adventurous I had no idea how wild my wife would become. We had c***dren within the first year and from there even though we had an active sex life it was getting mundane. Deb was always open to things as loved to show off her beautiful legs ass and tits. Loved to wear skimpy shorts and tube thops that showed off her big nipples. Access was very...

2 years ago
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Jennifers Cum Bath

A guy sighed and the cock in her left hand began to go off, sticky cum splattered against her wrist and dripped down between her fingers. Almost as soon as he pulled his cock away from her grasp, the two guys fucking her squelching cunt blew their loads too, she could barely feel it as it splattered deep inside her body. "Mmm," she moaned around the cocks in her mouth.Her right hand was still jerking off a particularly large cock as the two guys withdrew from between her legs, managing to...

1 year ago
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Jennifers Gang Bang

When the group arrived at the cottage, they went straight back to downing more shots of Tequila. Jennifer said there seemed to be a lot of men in that small cottage, more than she remembered being at the bar? Jennifer alone in a room full of guys playing drinking games. Not being very good at the games mean's that she had to down extra shots as penalties. Jennifer was feeling the buzz of the Tequila, but also loved being the centre of attention. Before long, two of the guys moved either side of...

Cheating Wifes
1 year ago
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Jennifers boyfriend

She stood before the judge, head down, and remorseful hearing his words, his question. “Ms. Starkey, would you like to explain why you did it? Why did you let it happen?” She collected her thoughts. She wanted to explain herself, but how do you do that with your dad, your mom, and your bigoted brothers in the courtroom with you? “Ms. Starkey why did you do what you did?” the judge asked again. His tone was more forceful. Her dad, a judge also, probably didn’t want to hear her explanation. She...

Interracial
1 year ago
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Jennifers Birthday Paddling

Jennifer was really a sweet catch, and an older woman to boot. I had been working a Real Estate office for 2 years in sales, and she joined the company in May of 89′. I immediately liked Jennifer a lot, not only because she was older but had a very sweet and kind air about her. I was 27 at the time, and Jennifer was a bit older than me (closer to 40 I guessed). I have always enjoyed the company of older women since my mid twenties. The have their act together, know what they want, and are at...

4 years ago
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Journey Of Indian Wife To Whore Part 8211 1

The heroine of the story Priya is a 26yr old Indian wife married to Arjun. They were married for a year now. They had a very wonderful one year. Priya was a bomb. She’s a show stealer right from her college days. The guys always use to imagine what it feels like to see her nude and touch those 34D firm breasts of her. She’s a modern and outgoing girl, so the jeans and t-shirts she used to wear only enhanced her 34-28-36 body size. Her height of 5ft 6in only added to her beauty. She had a few...

2 years ago
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Becoming Anthea

My name is Anthony and I am twenty-two years old. I have extra-long dark hair and darker eyes. I tie my hair into a ponytail and have a close trimmed beard. I look handsome and enjoy keeping myself in shape. I am a lucky guy as I have a very sexy girlfriend who is two years older than me. Zoe and I met at a mutual friend’s party and hit it off right away. She has short blonde hair and blue eyes. Her small beautiful mouth sits beneath a cute button nose. All in all, Zoe is a goddess and I love...

Crossdressing
2 years ago
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Mandirarsquos Journey from Traditional Wife to Sexy Sl

Mandira and Abhishek are a beautiful couple based in Bangalore. Mandira is 32, a beautiful, innocent and traditional housewife and Abhishek is 36, working in one of the companies in Bangalore. Abhishek got married to Mandira at the age of 30 who is from his native village. They have 2 k**s as well, elder son is studying in UKG and second son is still very young, Mandira is still breastfeeding the second k**.Mandira is a very beautiful housewife, had a somewhat fair complexion, 5′ 2″ height, has...

1 year ago
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Jennifers Home At Last

My wife finally moved home only because I told her to keep seeing other guys. The catch was she had to bring them home to a cottage on our property to fuck them. Tonight I'm waiting for her to come home from a date. So I can watch my slut wife suck a strangers cock and get fucked. Jennifer is a 45 year old 6ft with 40dd tits and voluptuous ass and pussy. When she left tonight she had on black blouse and half bra with fish net stockings and come fuck me boots. Finally I seen lutes pulling into...

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1 year ago
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The journey from ldquowiferdquo to ldquoHot Wiferdquo

This is a story about a journey my wife took to become a hot wife. In truth I thought my wife would never succumb to being a “hot wife”. Being an optimist I felt there was an outside chance, having often role played threesomes in the bedroom. She enjoyed the role play (within reason) so I thought I could induced her through reasonable argument one day? I always assumed if she did agree to cross the Rubicon we’d take the initial steps together, how wrong I was.Setting the scene:My wife Angela is...

2 years ago
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Becoming Anthea Part 2

My name is Anthony; I am twenty-two years old and live with my beautiful girlfriend Zoe. As you have read I have dark hair and dark eyes and I am clean shaven. Zoe is older than I am by a couple of years and is the driving force of our relationship. I am what many call a cross-dresser: a guy that gets great sexual satisfaction from dressing in women’s clothing.Of course, my girlfriend knows all about my cross-dressing. In fact, she encourages me to cross-dress. Once a week, generally on a...

Toys
2 years ago
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Chrissys Journey to Becoming a Woman Chapter 2

Chrissy's Journey to Becoming a Woman - Chapter 2 By Scott Wilson As I was approaching my twelfth birthday and puberty, I started to panic. We had talked with Dr. Brown about me starting hormone blockers so I wouldn't start puberty and develop the masculine characteristics associated with it. Her thinking was that I would start them around the age of 12. Unfortunately, she retired and I was referred to a Dr. John Anderson. Dr. Anderson had dealt with several Trans children over...

3 years ago
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Sharons Journey Part 9 Con te Partiro

Sharon's Journey Part IX - Con Te Partiro As Sharon sat in Julie's kitchen, gazing out the window, her attention was not on the park below but on the sky, a panorama of bright blue mostly shunted into the background by huge patches of thick clouds, the sides facing the sun fluffy and white while the mass away from it a brooding dark grey. Though November was not quite a week old, New York's November sky was apparent, bringing with it a brisk wind. "Wishing on a star?" Julie asked...

1 year ago
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Thangaiku Theriyaamal Amma Magalai Oothen

Indru tamil kama kathaiyil ilamaiyaana magalum pinbu vithavai ammavaiyum eppadi usar seithu matter poten endru ungaluku solugiren. Suvarasiyam athigam irukum kama kathaikul selalam vaarungal, en peyar karthik. En veethiiyil oru pen ilamaiyaaga sexiyaaga irupaal, avalai thinamum sight adithu kondu irupen. Thinamum aval kalluri sendru varum pozhuthu iru velaiyilum sight adika arambithu viduven. Aval peyar nandhini vayathu 21 irukum, avaluku veetil aan thunai kidaiyaathu. Veetil oru amma iru...

2 years ago
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Incest Journey 8211 Part 3 Mother Wife Sister Sisterinlaw

Hi readers, I am here with the third part of the series, “Incest Journey”. I hope you all enjoyed the first two parts of the series. Let’s start with the third part. Our marriage was set for the next month. Mom was too busy with marriage arrangements. She didn’t even have some time to spend with me. But fifteen days before my marriage, one night I forced mom for some bed pleasure. Mom: Can’t you wait for some more days, Vijay? You will get a wife and can fuck her. Me: Are you still loving me,...

Incest
4 years ago
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Stage nine of my journey to becoming Joann

It was almost midnight when I got home from my foursome. When I walked into the house Mandy was sitting on the couch watching the television wearing a shear teddy with nothing underneath. She looked at me and said, “Where have you been all night young lady?” I answered, “Out with the boys, Sis.” “I hope you don’t mean what that sounds like.” I responded, “If it sounds like I had sex with multiple men at the same time, then that’s what it means. I didn’t realize Joann was such a slut.” Sis...

Crossdressing
2 years ago
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Stage seven of my journey to becoming Joann

Life as Joann was moving forward rapidly. With the house to ourselves, I began ordering many things online and having them delivered to the house. In addition, to clothes and lingerie, I ordered a women’s facial electric razor, a laser hair remover, and several kinds of women’s skin cream. I also ordered some different breast forms to try out. Sis insisted on seeing everything that was delivered to the house, which wasn’t a problem, until an order of hormone treatment medication arrived. “What...

Anal
1 year ago
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Stage Ten Of My Journey To Becoming Joann

I was excited about the next soccer practice. There were no guys at the last practice due to Gurls Night. I was hoping Donny would be there this week. I stopped working at 4:00 so I would have enough to time to get ready. I went into the bathroom and filled my douche bag with a little over two quarts of warm water and special soap. I took off my shorts and panties before pushing the enema nozzle into my ass. I still get a hard-on as the warm liquid fills my bowels. I cleaned my face as I held...

Crossdressing
2 years ago
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Chrissys Journey to Becoming a Woman

Chrissy's Journey to Becoming a Woman By Christine Wilson Final Chapter With Sami being gone for the summer, I was hoping to have more time with Roger but, life had its way. Kim, the receptionist, took a leave of absence for the summer to have her baby. Dad asked me if I wanted to work there and I said yes. I told him that he had to pay me and that I needed some new "work" clothes. The salon has a reputation for being upscale and trendy. Those working there had to look the look. Mom,...

3 years ago
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Wife Journey Part 3

Wife’s Journey Part 3After my wife’s date with T things got back to somewhat normal. I say somewhat, because we are experience a whole new level of connection with each other after the gangbang night and her new connection with T. We still have our normal responsibilities, work, bills, k**s, etc. But it’s almost like we are on our honeymoon again. There is a level of excitement and sexual energy around her like I haven’t seen before. It is now Tuesday night and for whatever reason Tuesday...

4 years ago
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Jennifers Geschichte

Ich stand mit rasendem Herzen vor meinem Schminkspiegel, als ich mich inspizierte. Als ich mein Kleid über meine Hüften glättete, erregte der Glanz meines diamantenen Eherings meine Aufmerksamkeit. Ich überlegte, ihn auszuziehen, aber als ich mich an Sallys Kommentare über die Beliebtheit von verheirateten Frauen erinnerte, beschloss ich, ihn anzulassen. Ich freute mich über meine sexy Reflexion. Da ich kleine Brüste hatte, trug ich selten einen BH, und der dünne Stoff meines Kleides umriß...

Interracial
2 years ago
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Becoming Suzanne A Womans Journey

Becoming Suzanne - A Woman's Journey The third injection period was completely different than the first two. There really wasn't much sensitivity then. But just the change in my whole physical structure had felt so deliciously alien. It was as though I was this mystically intimate voyeur. It went so, so far beyond simply looking or watching. most mystical, mystical voyeur. It went so, so far beyond simply looking or watching. I had to wait much longer this time. I knew...

3 years ago
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Wife Journey Part 2 Wife has date

Wife’s Journey Part 2 Both wife and husbands perspectiveThe following week after my wife had her gangbang night we were lying in bed talking. I was in a playful mood as always but I usually let her call the shots if we are going to have some play time. She always keeps me guessing.She was still wearing her bodysuit that she wore to work that day. She likes to feel sexy under her work clothes and flirt with guys and sometimes girls when they come in to her store. She shared with me that she had...

1 year ago
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Becoming Suzanne A Womans Journey Part 3

Part 3 Becoming Suzanne - A Woman's Journey The project took a couple of weeks longer than expected, but everyone was very happy with the results. To mark the success, the prime developer rented out a slick new restaurant on the lower East side and everyone who'd been involved was invited. That meant nearly a hundred writers, directors, media people -- a heavy dose of "creatives" and a few business types all mixed together. It would be a great way to blow off the pressure of the...

1 year ago
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BDSM Journey Of My Shy Wife Zainab

Hello to all ISS readers, this is my first story on ISS. My name is Zubair Khan. I am 27 years old and working as a software engineer in a top IT company in Pune and I come from an upper-middle-class family, living in a 2 BHK apartment in a posh locality in Pune with my beautiful wife. Being young and energetic, I have maintained my physique very well as I regularly go to the gym. It was recently that I got married and it was an arranged marriage. My wife’s name is Zainab. She is so hot and...

3 years ago
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Hotwife Chapter 3A The Continuation Of My Hotwifes Weekend

HotwifeI woke up during the night with Marcus cuddling me and playing with my pierced nipples, which once again was making me wet.I climbed on top of him and proceeded to rub my pussy all over his hard cock. It wasn't long after that I pushed myself down him which caused us both to orgasm again and then we fell back to sleep.We woke up about ten. We both needed a shower. Marcus proceeded to wash me paying special attention to my pierced nipples and pussy. I decided, 'Two can play this game.'I...

Wife Lovers
3 years ago
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Journey from Mangalore to Bangalore drinking mothe

Hi Friends, this is Rajesh, presently 38 years working as an Engineer in an MNC, and settled in Bangalore now.. I am fair in colour, well built with a gym body and most important with an 8 inch dick. I was aware of the woman anatomy at that age by reading sex books and watching porn, but never had any chance to see a woman naked, but was longing to see a naked woman and masturbating myself thinking about it.This is an incident which happened when I had been to Mangalore to attend a marriage...

1 year ago
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Thelma and her brother

Note : This story is completely fictional!In nineteen forty six Thelma Lou Anderson was married with three kids. Linda was the oldest. She was sixteen. Guy and George was ten and Guy seven. Thelma owned a beauty shop in Kansas City. She suspected her husband Lawerance was cheating on her again. She followed him one day when he thought she was at work and saw him go into a house. A woman opened the door and he went in. That was all the proof she needed. She went home and packed her suitcase and...

Incest
3 years ago
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Wifes Journey Part 5

Wifes Journey part 5 Con't. It’s been about a week since my wife had her time away with T. The week was pretty busy with work, k**s and family stuff. It was now Tuesday and I always look forward to this night because it seems to be the night my wife and I have some fun with each other. It happens other times during the week but definitely Tuesday nights.We head back to the bedroom after our daughters go to bed. My wife asked me to bring the laptop back. I love when she tells me that, because it...

3 years ago
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The Passion of Mother Ethel

Mother Ethel always enjoyed the short walk to the train station. It was beautiful Autumnal morning and Mother Ethel took the opportunity to walk to the train station as she knew that she had a very busy day ahead. Those that saw Mother Ethel along the way bowed reverently,they knew that Mother Ethel was a Nun of the Monastery of Repentance and when a Nun or a Monk walked past it was polite to bow, for many knew what the Nun's and Monk's of the Monastery were capable of. As Mother Ethel strolled...

2 years ago
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Stage six of my journey to becoming Joann

As I awoke on Christmas morning I found three presents on the end of my bed. There were handwritten tags on each with the message: open in private. There was no doubt in my mind as I opened them that they were from Sis. The first was a body shirt that pulled down and snapped in the crotch. It was white with a v-neck trimmed with lace around the neck and sleeves. The second was a set of breast forms slightly bigger than my regular ones with conspicuous and pert nipples. The third was a very...

Crossdressing
3 years ago
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Wifes Journey Part 4

Wife’s Journey Part 4My wife works in retail so her hours vary, day shifts, night shifts, weekends, etc. This particular day she was working the night shift and doesn’t go in till 2PM. Sometimes she likes this shift because it gives her time home alone without me and our daughters. I got home before my daughters did and when I went back into the bedroom I noticed the laptop on the bed. Sometimes this means she was either shopping or looking at porn and having some fun. I also noticed some...

4 years ago
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Holidays with Peggy my wifes sisterpart2

So nothing else happened that night between me and Peggy, and I needed the rest so my sore cock could heel. The next day was Thanksgiving, spent with the whole family, again pretty tame day, no sex. On Nov 25th, the day after Thanksgiving, I had to be in work early, but also got to leave early. I got home and as I walked inside I heard the shower running. I went upstairs and figured it was my wife, it was. I stripped down and hopped in with her. We started messing around and eventually ended up...

4 years ago
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Stage five of my journey to becoming Joann

As I opened my eyes it was quite light. I sensed it was late morning. Bob was still spooning me, but his dick was soft and must have pulled out of my ass sometime through the night. I quietly rolled out of the bed and walked to the bathroom. Before sitting to pee, I reached around and pulled another condom from my ass. I guess when he lets his dick soften inside me it shrinks from the condom leaving it in my tight ass. I’m finding it to be an after sex turn-on. I sat on the toilet and peed....

Crossdressing
3 years ago
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Becoming Suzanne A Womans Journey Part 5

Chapter 5 (Final Chapter) Becoming Suzanne - A Woman's Journey Steven noticed Suzanne across the restaurant shortly after she arrived. It was a large open room and she was getting a drink with Julie and laughing with some of the others at the bar. She wore a tight black dress, with a plunging neckline, that hugged the contour of her curves. "God," thought Steven, at once frustrated and intoxicated. He hadn't stopped thinking of her since that time they'd shared a smoke in...

2 years ago
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My Wife8217s Journey From Frigid To Super Hot

Thanks very much for positive response to my stories. Since all stories in ISS are based on real experience and I was apprehensive of readers reception to fantasy based sex stories and am gratified to receive appreciative messages please find one more story from fantasy dreamland and I hope you will enjoy. I had a stopover at Amsterdam for four hours, so I sat in the air port bar nurturing a whiskey since it was past midnight, the bar was almost deserted. I chose a farthest table in a dark...

2 years ago
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Dot Dorothea and Dick

Dot, Dorothea, and Dick Chapter One Dear sister: I found this letter among some others, scrolled up and tied with purple ribbon, in a chest belonging to our great grandfather. The name Charles has belonged to several in our family line, but I believe I know the one who received and saved this letter, and kept it preserved for so many years. I believe the letter speaks for itself, so I will now offer it up to you. Dearest Charles: I hope this missive finds you in such good...

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