SHARING NEW EXPERIENCES WITH SISSY CAROLE free porn video

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A few months ago while chatting with Carole and talking about things we would like to do, she told me: “Would you like we do together some of the things we have talked about and we both like? Would you dare to make our fantasies a reality?” At first I thought she was like joking at me and I replied: “Of course I would like, do you think I am not able?” She then said: “Then why don’t I visit you and have a lot of fun with me”. I told him that I would think about it.

From that moment the idea of meeting Carole was in my mind all the time. I couldn’t stop thinking about it and that had me is a state of almost permanent sexual excitement. Intentionally I didn’t chat with her for a week but finally I couldn’t resist more and decided to talk with her. I asked her if she was serious about having an encounter. She said that definitely yes. I told her: “Then let’s do it and enjoy together as much as possible”. Since that moment we started to talk a lot about how would be our encounter and what things we could do together. At the beginning I was not fully aware of my decision and I had lots of doubts because I have never had a sexual experience like that but Carole is a sissy with a fantastic cook that attracts me a lot and I got myself convinced that I really wanted to go through that because we both are quite pervert and like punishment and torture.

During weeks we discussed a lot about the scenario and the content of the sessions we would have together. We considered that it was very important to fix some rules, to list and delimit the things we would do one to the other and together and to establish our preferences. Carole is not much for certain things that I like and at the same time I am not much for other things that Carole likes; therefore we decided to respect each other’s desires. In that sense we agreed that needles would be only for me and as the question was to enjoy together she would put them on me. We also agreed that Carole would not fuck my ass with his cock but as she loves to be fucked I would fuck her beautiful pussy ass as much as possible.

We both got very busy organizing everything. I selected a place for the encounter, purchased things we both wanted and together set up many details. We agreed that she would visit me for a week and that we will stay in a very remote place where nobody could be watching us. I found a large and isolated house in the mountains and in the middle of a forest with a generato for electricity. The access was restricted and I could be sure that nobody would see and disturb us. We would have full privacy and that made me feel very safe and free. The house had two floors, a very large Japanese style bathroom with hot spring water pools, one indoors and the other outdoors. On one side of the house there was a large workshop with some old machinery. I thought that was the perfect place where to perform together many things. I got the necessary equipment and made of it a dungeon.

Carole bought her plane tickets. Upon arrival she would have to take a domestic flight to a small town. She also reserved a hotel near the airport at the final destination because she wanted to rest after the long flight and we decided we would meet the day after her arrival.

I bought a lot of equipment and stuff I thought we would need for our sessions of pleasure, lust and torture. A few days before encounter I went there with everything I had bought including food and drinks for a week. I arranged and cleaned the house and specially the workshop or yarn where we would have our sessions.

It is Wednesday middle of August. Carole sends me a message saying that she is ready to embark and that she feels nervous, a little worried and afraid of what is going to happen but at the same time she really wants and needs to live this adventure with me. I get sexually excited thinking about her arrival and my cock becomes very hard.

The same day I visit several shops I had previously selected via internet. First I go to a sex shop where I buy things I think will be good to use: restrains, ropes, clamps, dildos and other things to insert. After I visit another store but specialized in BDSM articles. There I buy two sets for electro stimulation, needles I want Carole uses with me and two sets of sounds plus some additional items. Later I go to several lingerie boutiques and I buy some panties, bras, stockings and camisoles that I will give to Carole as a present and that I want her to wear while being together because I know she loves that.

Next day, on Thursday I leave my house and travel by car to the town where Carole would arrive. It is quite far away and I get there when it is already dark. I lodge at a hotel different than the one Carole will be already staying. I received a message for Carole saying that she is already at her hotel and she is willing we meet next day. I am extremely nervous and excited but I hardly can wait to be together and start our promised sessions of pain and torture. I decide to write a list of the things I want to do to Carole and the things I will ask her to do to me. That excites me more but I finally get sleep.

It is Friday morning. I leave the hotel and drive to the hotel where Carole is waiting for me. The moment of the encounter with Carole has finally arrived. It is 8 a.m. when I see Carole getting out of the hotel. She is wearing a nice blue dress, high hills a wig and big sunglasses. I approach her, exchange a couple of kisses and we quickly get into the car. I tell her: “Thanks Carole for coming. You look very attractive and sensual. I am willing to see what is under that dress”. Then Carole raises his dress and I can see her beautiful legs and the sexy stockings and garter she is wearing.

We drive for long. Carole gets sleep because of the jet lack. I wake her up when we are arriving at our destination. I check the time and it is already midday. Once there Cole likes a lot the place and the area full of trees and surrounded by mountains. She also likes the big house a. We unload the car and enter. Carole says: “Thanks a lot for inviting me. I like very much this place. We will make of it a house of non-ending lust, pleasure and torture. As you said I can see that nobody will disturb us. I want to tell you that from now on you can do to me whatever you want, and as your submissive please do not hesitate to use on me any torture you may consider my body deserves or need. I am willing to start but first show me the house please”.

I take her to the large living room, the kitchen, the several bedrooms and the large Japanese bathroom that she loves. We go to the back part of the house where there is the large yarn where I have arranged a long work wrench and tools and winches hanging from the ceiling. There is also a nice sofa and a narrow low bed. I tell Carole: “This is going to be our dungeon and I think I already have here most of the things we will need for our sessions of pleasure and torture. Later you can have a look at what it is inside those lockers and cabinets in order you get familiar with them. I hope we will use them all. Let’s go back to the kitchen and prepare something to eat”.

We have a light lunch with some wine. Carole says: “Thanks again for inviting me; I am very much pleased to be here with you. I would like to know how you feel. Do you feel comfortable with me here? You must be aware that this is real and everything we have been discussing since long ago we will occur from now on, I respect you and we will only do what we really desire, we must feel relaxed and not forced to anything. Torture is pleasure for me and that implies some pain. I want to make sure again that you want to share this with me. I understand that if you have taken the decision of inviting me is because you wanted and know well that our play is going to be very intense. I don’t know to what extend you bear real torture, how much you like it and how you will accept it once you are in the real and hard situation you told you want for yourself. I tell you that I am sure of what I want and need and I am fully committed to experience new and hard things with you. Anyway we will be evaluating that along the sessions. And if you are not tired and feel recovered, I will like to start as soon as possible, we have to do many things and the time is limited”.

I reply to Carole: “I am perfectly fine, you don’t have worry, I am full of energy and ready to start an soon as you may decide. Be sure I know well why we are here, what you want and what I want: and this, fortunately, is real. I don’t have a large experience and I cannot tell you now to what extend my body can bear the tortures you are thinking of but I can tell you that maybe I become a surprise for you. Be sure that my mind is willing and ready to share with you many things. You will be my submissive and I will procure you as much torture and pleasure as you may request or need and you will experience new things. I want you to deliver me with amounts of pleasure in the same way I will do with you. I will also be your submissive because, as we agreed before and you promised, you have to make of my ass a new source of pleasure for me. As we also agreed I will train your cock in sounding while you train my ass to be able to be penetrated with large objects. I would love we both become capable of deep penetrations in our cocks and asses. And now why don’t we have a shower together to relax and start to know each other in a more intimate way before we go into the hard things?”
We go to the bathroom. Carole takes off her dress and I can see the beautiful lingerie she is wearing. She takes everything off while I get rid of all my clothes. We are now fully naked one in front of the other. Our cocks are fully erected. I like Carole cock and balls. All her body is smoothly shaved. We shower and wash our bodies. I tell Carole: Your body is so smooth, I love it. I would my body to be like yours. Could you please shave me now? Please shave well my pubis, my balls and my ass, don´t leave one single hair down there”.

She lathers me with soap and while she is shaving me my cock gets harder and I feel very excited. She first shaves my sack and cock and after all the pubis down from the belly. She does it very slowly and every passage of the razor on my body becomes a source of excitement and pleasure for me and for him. She makes me to set apart my legs and to lean forwards and she shaves my ass with a lot of care. She starts massaging my anus and then introduces just the tip of a finger on it. Nice feeling. When she finishes with the shaving of that area I tell Carole: “Please shave also my chest, my legs from my feet, my arms and my armpits. I need to have my whole body totally smooth to feel better the tortures I will receive from you”.

Carole does it and when she finishes says: “This is very exciting and this is creating among us the intimacy and conspiracy we need for what will come. I think it is time I put your cock in my mouth and tastes you. I cannot wait more for that”. She kneels down in front of me and I push her head towards my hard and excited cock. She is really good sucking and my cock goes deep to her throat while she caresses and pulls my balls. It is too much excitement and I don’t want to come. We stop. Then I take her hard cork with my two hands. I like it. His cock head is big and his cock is thick and hard. I pull down hard her balls and she screams with pleasure. But we must wait; it is not the time yet for our mutual sessions of pleasure. We dry; we put on bathrobes and go back to the living room.

Once there I go and get the presents I bought for Carole. I give her ten different sets of lingerie and say: “I want to see you wear lingerie at all times, a different set for every session we will have. Please use always a pair of stockings, a bra and a panty and if you wish a camisole. As you can see the bras are open cup and the panties are open crotch, like that your nipples will be accessible to me and your cock will be always out for my pleasure and your torture”. She tells me: “Thanks very much. I love them all and I promise you that I will wear lingerie for you all the time. As you know I love to do it and I will only take it off if you need me fully naked. But I would like to ask you something. Why don’t we both wear this beautiful lingerie and other I have of myself? That would be very exciting for me. Your body is so smooth now that the lingerie would be a perfect fit for you. I would like to select the best combination for you before every session and I would also like to dress you up before every session. Would you like? I accept and Carole becomes very happy about it.

I tell Carole: I also bought some things we should take to enhance our lust, to have lasting erections, to be able to orgasm and cum several times a day and to increase our capacity to feel torture and pleasure. First these are some Chinese herbs and powders which we must boil and make an infusion with them. We should drink that all the time to burst our sexual desire; we will help us not feel tired and will allow us to ejaculate many times. We must also take these special pills, there are like Cialis but much more powerful and their effects last longer. I can assure you that taking them we can have our cocks erected for at least 12 hours, even after we ejaculate. They are very safe. We must have one in the morning and another in the evening. Finally these are 3 different lotions. One is for our tits and nipples and will make them extremely sensitive to the touch. The second is for our cocks, it will penetrate thought the skin and produce a big dilatation of the blood vases, like that our erections will be harder and our cocks will become thicker. The last one is for our glans, it has the double effect of making them hyper sensitive and activates the blood concentration there, our cock heads will grow and we will able to feel very strongly”.

Carole: “For sure we will use all those things. Thanks for bringing them, I think you had a great idea. I want to have my cock hard all the time and I really want to cum many times and make you cum for me a few times a day. I want eat your cum and have it inside my ass, I will not waste a single drop of it. Should we take the first pill now?” I say: “No, let’s take it later, I think it is better we rest for a while and that would be difficult if we have our cocks fully erected and we feel over excited. I prefer we have a long and intense session tonight and for that we both must be in very good shape. I am willing to start taking care of your cock and balls, I can hardly wait you start doing things to me. Let’s first go to the kitchen and prepare a couple or jars with these special herbs and powders”.

Once in the kitchen and while I am preparing the infusion Carole goes to the dungeon to see what devices and items I have arranged for our mutual satisfaction. She looks all over around and checks what is it inside of drawers and lockers and she is happy to see all the things we will use together. Once she is back on the kitchen we go to our separate bedrooms for a little rest. I tell Carole: “Please rest well. I will wake you up just before 8 and we will prepare dinner together. After dinner we must start with our first training session and after that we will have our first session of intense torture”.

We go to our respective bedrooms. I quickly fall sleep. After a few hours I knock at Carole’s door to wake her up. She tells me to wait and after a while she opens the door and I can see that she is wearing a beautiful red set piece of lingerie and red stockings with high heels. She makes enter her bedroom and stand up in front of her. She takes off the bathrobe I am wearing and puts on me a black nice bra with very small cups and also black sexy panties. My cock is hard as a rock. She also puts on me a black nightgown. It is first time I am dressed like that and I like. I notice that Carole is as excited as me. We go to the kitchen where we prepare dinner. We enjoy the food. Each of us drinks two large cups of the infusion I had prepared with the herbs and powders I brought with me.

Carole says: “I think the time to have our first session together has arrived. But first as you said we should go under the training we agreed. While showering together I noticed that your ass hole is much more closed that what I thought, therefore you ass dilatation is something we must start as soon as possible and it will require long sessions of training and even something else. I have taken with me this cream that will relax your anus and will relief you from the pain you would feel with a too fast dilatation. Let me take care of you in this aspect. As I promise you your ass will become a new and fantastic source of intense pleasure. I think that in a couple of days you will be ready to penetrated and start enjoying it. We must share some of the dildos and I hope that to see me with the larger dildos fully plugged in my ass will encourage you to be penetrated more and more. In order to achieve a good and lasting dilatation you must keep dilatators on your ass all the time, including while you sleep. I am also willing to begin with the training of my piss hole as soon as possible in order to be able to share sounds with you. I am sure that will be a new source of pleasure for me.

I tell Carole: “I think it would we good if we make regular training sessions of at least one hour before our torture sessions together. We can do the training after breakfast, after lunch and after dinner. I agree with you that I need and urgent and intense dilatation of mu anus and I and ready to have in my ass the dilatators of the increasing caliber you may consider and for all the time needed. Regarding the stretching of your piss-hole I think you will also must have some stretching devices inside your urethra all the time and for a few days. I have prepared a special room for that in the basement that you haven’t seen yet. Let’s go there and let’s start. I think we both urgently need it”.

We take our pills and go down to the basement. Carole is very much happy when she sees the equipment of the room: two machines, two low tables and a large sofa. I tell Carole: “I call this big machine “The Stallion”, it is perfect for a hard, deep and good penetration of our asses. It is made entirely of steel and very resistant. The motor is powerful enough to leave us a lasting impression. The linear arm of the machine can swing anywhere from 10 to 100 degrees for greater flexibility and will allows us to take the machine in a missionary, doggie or cowgirl style position. We can use many of the u-lock dildos I have and adjust the stroke between 0 and 180 strokes per minute.

I continue explaining to Carole: This other machine is called the “Shock Spot Fucking System”, it is very advanced and has a robotic pleasure system. It motions that are impossible for rotary-based fucking machines to perform. We will be able to control the stroke length, speed, smoothness and pattern at the touch of a button. The system has software installed for selecting pre-programmed routines or creating our own, using our intuitive point and it is fully automatic and programmable, with or without voice recognition. Although it is not as big as the first one, it is very powerful, 17.535 pounds of push force, and the maximum speed can be up to 23.62 inches/sec. Also the stroke capacity per minute is incredible, 340 strokes/min at stroke length of 2.0 inches and 250 strokes/min at stroke length 4.0 inches. At the beginning we will use the big one for your anal dilation and the other one for your urethra and piss-hole dilation.”

Carole says: “It is time to start. Please lay down on doggy style now. So, is your bum ready for the BIG time? Great, but remember there’s no rush! As with any training session, you must warm up first. So, relax”.

Carole starts off by inserting her little finger in my anus and slowly moves it in a circular motion. I feel comfortable so far. I notice how she tries to gently stretch my anus with two fingers. I tell her: “OK Carole, now I am ready for action!”

She starts with a small, tapered dildo. She inserts it into my anus. She points slide it back out. She waits for a moment and repeats the process. I find that this time I can enjoy some deeper exploration. She repeats until I have gobbled the dildo up whole. Then she takes a bigger dildo and repeats until I have the gaping hole that she is after. She puts some cream on my anus and switches on “The Stallion” a bigger dildo. Then place it in front of my ass and insert it on it. The dildo has only 3/4 inch diameter but it 5 inches long. It goes easily inside my anus. Carole connects the machine and the dildo comes in and out my ass. I like the sensation. I push back my ass and the dildo goes deeper inside of me all its length. After a minute Carole changes the dildo and attaches to the machine a dildo one inch diameter. She places the dildo facing my anus and switches on again the Stallion. I feel some pain when the dildo goes inside on me but I also feel pleasure. Carole increases the speed and the dildo goes in and out of my ass very faster and faster. I push back my ass t until feel that dildo also goes full into my anus.

Carole kneels in front of me and with the Shock Spot Fucking System facing his erected cook. She attaches a thin sound of only to the end of the other machine. She puts some lubricant on his piss hole and slowly inserts the sound in his piss hole. I am very close to her and I encourage her to have inside all its length. She switches on the system and the sound starts coming in and out her cock. It is very exciting to watch her while I feel the dildo going deep inside my anus.

After a while Carole leaves her machine and come to me. She makes me change position to a missionary one. She caresses my hard cock and put it in her mouth for a while. She says “You are doing in it wonderfully and I also feel that I can have my piss hole stretched pretty soon for you, I am enjoying it. Are you enjoying your anus stretching? I say “Carole this is fantastic. I am enjoying a lot and I also want to have wide open soon in order you can insert into me some of the things we have in those drawers”. Carole says: “Now I must use with you a different dildo, a cone type one, like that the dildo will stretch your anus in a progressive way. You can move forward it you want it stretches you more. Let’s go”.

She attaches the new dildo to the Stallion and places in front of my anus. The tip of the dildo goes easily inside. She switches on the Stallion and I feel how my anus opens and close. I move backwards for a bigger stretching. Carole returns to her machine and uses a thicker sound on her cock. After a while the conical dildo goes full in and out of me. I feel so good. Our cocks because of the pills are hard as ever and the infusion has made us very excited and in urgent need of torture. One hour has passed. We leave the basement go to the dungeon ready to start our first torture session together.

TO BE CONTINUED

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Sissy Clinic for Bois, Chapter One: My New Sissy Client Summary: A young woman meets with a rather unconventional psychotherapist who offers a unique form of treatment aimed exclusively as effeminate young men. "I appreciate you taking the time to meet with me," Jaiden Chapman told me as my assistant Susan served us both coffees. "Professor Greene at Texas Woman's University recommended you," she continued. "Professor Greene, Kristen, is my thesis adviser -- I'm working on my...

3 years ago
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sissy cunts New Life Pt 1

sissy cunt's New Life - Part 1 The plane finally touched down in Cape Town. It pulled to the gate, and the tone sounded, signaling that we could stand and take their luggage from the overhead. Grabbing my purse, i slung it over my shoulder and stood, stepping out into the aisle. i ignored the disapproving stares of the other passengers, my face turning bright red. They could clearly see the business cards, condoms and make up through transparent sides of my bright pink purse. i...

2 years ago
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Trucker Daddy gets himself a New Sissy part 1 and 2

TRUCKER DADDY GETS HIMSELF A SISSY BY DEEWET It could easily be the lowest point in Denny's life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truck Stop. He almost jumped out of his skin when someone knocked on the window. Denny...

3 years ago
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Sissy Clinic for Bois Chapter One My New Sissy Client

“I appreciate you taking the time to meet with me,” Jaiden Chapman told me as my assistant Susan served us both coffees.  “Professor Greene at Texas Woman’s University recommended you,” she continued.  “Professor Greene, Kristen, is my thesis adviser — I’m working on my M. Ed. in curriculum design, and when I shared my story with her she was certain you would be able to help us.”I recognized the professor she was referring to immediately from working with her several years earlier when I...

Femdom
3 years ago
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Teaching the Sissy Maid Workshop at the MVG Chapter One Training a New Sissy

I simply loved teaching the introductory Sissy Slave Classes at the Matriarchal Values Group, or MVG, and since the class is limited in size it is almost always fully enrolled and most people who take the course end up registering months early to make sure they will have a place secured for the upcoming class.The Matriarchal Values Group, or MVG, was a private society of like-minded, dominant women who believe and live our lives based on our individual interpretations of what it means to be a...

Femdom
3 years ago
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A new Master for sissy 2

I was shaking as I stood at the counter waiting to buy Master’s coffee. I knew I had taken a major step by leaving my mobile phone with Him, and that it was a complete leap in the dark. At this stage I was more scared than excited, already questioning my judgement, almost wishing I’d not been so stupid as to open my life up to a complete stranger, giving Him the power to control and ultimately destroy me. But it was too late for second thoughts, and as I took His coffee upstairs and walked...

3 years ago
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Masters Sissy Slave Chapter 7 A new game

Chapter 7 - A new game Again awaking in the morning in a simple straitjacket, Masters control was now so strong that I considered a straitjacket simple! In Masters arms I felt a huge sign of relief that my evening was over but again I had to resolve myself to the fact that this was my life now. My body was screaming in pain, the torture inflicted on my gorgeous breasts was beyond what I had ever imagined. It must have been a sign of my diminishing mind and need to please master that...

2 years ago
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New GF Trains Me to be a Sissy Slut

"That's it baby! You are such an amazing cock sucker!" I moan around the cock in my mouth as I bob up and down quickly. I feel hands on the back of head grab my hair to stop me from moving up and down the amazing 10 inch black cock. I've been kneeling for almost twenty minutes slowly working this monster. I've only been able to take just over half of the cock so far. "You are doing very well sucking your first dick. Though a good cock whore needs to learn to deepthroat and feel what it's like...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

4 years ago
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Club Gomorrah The Sissy Saga Chapter 3 The New Girl

The headset was suddenly dead, it was only moments later when she heard a voice call out that she realised the moaning was her own. “I said that’s enough Slut.” Pain shot through her as the collar around her neck began to shock her. “Dumb slut. The fun’s over, your Master’s waiting.” The woman sighed, and the collar sent another shock. “That one was for making me wait. Clean her up and bring her to the viewing room, and don’t fuck around. The guests are waiting and I want them to see my new...

2 years ago
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Birth of a New Sissy Part III Completion

Birth of a New Sissy Part III: Completion By DarkPrince67 [email protected] I suppose at some level I knew it would happen. Or at least I should have. After nearly a month of servicing Jeff's cock and fucking myself silly on my dildo lover things took a turn. I came home from work a little early on a day Laura was off as well. When I got home she was out, but as soon as I walked into the house the phone rang. I grabbed it, not really thinking much about...

2 years ago
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A new Master for sissy 1

As a submissive and obedient sissy with a deep craving for humiliation I’d served a few online Masters during my 50’s, but when I hit 60 I started to crave the experience of serving a Master in real time. I knew that to do this I’d need to join a site through which I could contact local men, and so created a sissy profile on fabguys. I uploaded pics of me as a sissy, wrote a reasonably honest summary of my experience to date, made it clear that it was real domination I was after, and kept a...

2 years ago
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Carole

I wrote this story a awhile ago where it was posted on my blog I have since re-visited the story and this is the revamped version I hope you enjoy reading it. Hello I’m Carole 42 years old divorced with a twenty year old Son Frank this is my story.all this occurred five years agoI have always loved my son yes I know a Mother is supposed to love her son or Daughter but my feeling went deeper than that I admit I adore my son at fifteen he is in every way an adult, I also realize the fact that my...

2 years ago
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SISSY MOMMYrsquoS NEW LOVER

SISSY MOMMY’S NEW LOVERI looked down at the poor thing, he had such sad eyes. “What’s the matter dear, corset too tight?” He shook his head ‘no.’ “No, Mommy, it’s fine.” “Fine? Well then perhaps we can get you down another half an inch. Up,” I commanded. Dejectedly he rose to his feet & turned his back to me. Would he never learn to give an answer without getting himself in more trouble? I do believe that his continual sissification was dumbing him down. He might very well end up an...

1 year ago
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First Sissy Experience

I accepted a new job in an executive role at a company in Kansas City and obviously with the new job came a new home and new neighbors. My wife and I were really excited to move into a very nice upscale neighborhood, we looked forward to getting "plugged into" our new community as well as get to know our new neighbors. What I could never had imagined is what "plugged into" would mean for me.We moved into our new home the first week of September and were warmly welcomed by the neighborhood with...

4 years ago
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My New Sissy Life

I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted online seeking two submissive males for "training." I read the description which said, "Attention sissy boys! Have you ever wished that you were a trained sissy slut? Of course we both know the answer to that! I'm sure as you were pathetically scowling the web to find things to excite your little...

Crossdressing
3 years ago
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A Sissyrsquos New Daddy Search

I couldn't sleep last night so I figured I'd fire up the laptop. Lately I have fantasized about being totally dominated and used by a real top daddy since my old one moved away. When I’m in this type of mood I usually will do a quick hookup, but I was in such a sassy state, I really missed having a man taking charge of me, to humiliate me. It was a good night, I was getting a lot of messages from guys interested in teaching a little sissy how to keep her daddy happy, and how my fat brown ass...

3 years ago
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The Birth of a New Sissy 1

If you are offended by male to male sexual encounters or other explicit sexual situations, STOP now! This is your last warning. :-) Birth of a New Sissy - 1 ? by: DarkPrince67 [ [email protected] ] I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old, about average in most respects, a little spare tire trying to form around the...

3 years ago
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sissy Meets her New Daddy Ch 1

So I took the plunge and put out an ad on Craig’s List. I was travelling in a city about 120 miles from home and figured this was far enough to not be found and close enough to go back if I had success meeting a fuck buddy that could be longer term. I got myself all primped and wore a tight print dress, matching bra panty set subtle yet slutty makeup and my fave long blonde wig. The ad attracted immediate attention and I was sure to mention I was a sissy who wanted to be treated like a girl. I...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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A Sissy Fantasy A Day And Night With Daddy

A Sissy Fantasy - A Day And Night With Daddy Daddy's Cocksucking Princess I awoke after falling asleep after last night's escapades, and the first thing I I notice is the chastitiy, it immediately reminds me of what happened last night. I wasnt expecting to be put in chasitity last night, Daddy had hinted at it, but I did not think he was have me in it so soon. I did not really want to have my clitty locked up like that, but I really want to please Daddy, so of...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

3 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

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