First Steps to Sissyhood
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crossdress – sissy – anal - plug – oralI thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like what you see, send me your number and we can set up something, Steve." I sat there in a matching...
They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car.It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. Im very easily intimidated. And there I was in a tiny plaid mini and white pump sandals about to mince my way passed a group of young black street-toughs....
Pepper and I knelt on the silky sheets of the bed and studied each-other in disbelief; our cocks rigid and ready for relief. I took her sweet sissy cock in hand as I sniffed and licked at her face and neck; her skin as white and silky as the sheets. She thrust her slippery little sissy cock back and forth between my fingers as I teased her glistening little pink bell-end. Pepper panted with anticipation as she unhitched her crop top; her sweet little breasts stood firm and inviting, my...
Master's Sissy slave by llatex39 Understanding After the final orgasm I could feel Marcus's hands over my penis and it then being forced back into the constrictive chastity cage, with a turn of the key I was now safely locked away, not that I had any more desire after cumming 6 times over the course of the night. Completely dazed after an incredibly restless night I felt the machine loosen it's bonds on me so I could stand up away from the machine. Marcus then removed the VR...
Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave’s cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty’s thong. She smiled with a sense of admiration as he licked and lapped at the savoury gusset without faltering in any way; she watched over him, whip in hand as he lovingly licked at the tangy brown...
Chapter 4 Love It took a full day to recover from the previous evening. After I had passed out Master had clearly taken me down and fitted me into the latex sheet that I was currently resting in. I had awoken in the morning expecting Master to untie me and let me prepare for the day. Thankfully he recognised the rest that I needed and as I lay there slowly I begun to feel the lasting effects of last nights session. My body was aching and stung everywhere, none more so than my...
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...
I was starved for sexual attention, all those hormones swelling up in me, it got to the point where I would spend hours locked away in my room watching 100's of hours of porn desperately wishing I could take the place of any of these actors I didn't care who I just needed a release! After a while porn wasn't enough, I began frequenting chat rooms looking for girls to talk to but as I soon found out on the Internet Men are Men and so are most Women and the Women who were actually Women...
Another huge African was now in attendance at Ella's fortress; Ayesha, no stranger to slave; he knew every nook and cranny of the magnificent woman's beautiful physique, he had licked her clean before. The haughty bitch wore only a purple chiffon full length dress and a golden thong which barely covered her sumptuous womanhood; this was there purely as part of her schedule of titillation; she had been key in developing slave's wanton urge whenever confronted by soiled panties. As she...
She had always been very rough with him, the big woman, but this morning was exceptional, and different. She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or had him lick her till she grunted out yet another orgasm, before serving him with cane or whip. Now morning was here she face sat him; her...
Minimum Sissy Slave Requirements:A SISSY GURL IS KEPT IN CHASTITY: A sissy must be ‘permanently’ locked into a chastity device at all times, (except during supervised cleaning), her orgasm’s denied and any discharges graciously granted will be 100% controlled by her key holder and under the proviso that the sissy will consume them. The sissy no longer has a penis; she has a “clitty” and will always refer to it as such, the “clitty” is for her Alpha owner to control and use as their...
She had always been very rough with him, the big woman, but this morning was exceptional, and different. She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or had him lick her till she grunted out yet another orgasm, before serving him with cane or whip. Now morning was here she face sat him;...
And talking about her, you can hear now a familiar sound. Yes, she’s coming because as a good sissy submissive you know the celestial / infernal sound of the High Heel shoes on the floor, so you open your eyes as in front of you some soft lights begin to turn on. You see her coming in a way you have never known before. Yes, she’s coming towards you, but OMG! She is absolutely naked now, except for those High Heel shoes you sometimes hate and sometimes love, but you still not surrender yourself...
Chapter 3 - Broken For the following days and weeks I settled into a routine of Masters design. With my resolve to comply with the commands of my Master and see out this month I surprisingly found satisfaction in the simplicity of being a slave and following orders. I had worked so hard to follow all of Masters rules and apart from a couple of unconscious misdemeanours, that Master accepted were not malicious I had found myself enjoying the life. I mean I would have preferred my...
From A Society Girl From A Society Girl To A Slave Anonymous Chapter I All the inhabitants of the villageof Kronink in Scotland know the castle of Kelingtonwhich stands majestically a few miles outside of the village, and which neverfails to draw all the visiting tourists who are struck by the mysterious charmof its old-fashioned towers looming at the horizon and surrounded by the thickvegetation of an immense park. In that castle lived Lord Kelington, the heir of an oldScottish family...
Ella took the chain from their collars when they reported to her, together for the first time, in the morning. Pepper’s eyes were exceptionally bright this morning, and slave looked full of vigour and ready to carry out any command that befell him without the slightest hesitation. Pepper gripped his hand tightly, lest she should suddenly wake from this beautiful dream; she smiled to herself, the tenderness she felt in her bottom could not be down to any dream, she had been well and truly...
Master's Sissy slave by llatex39 The beginning "Welcome to you new life" Stirring slowly I opened my eyes to see my Doctor Marcus standing over me. I was at a loss... where was I? what had happened last night? I could remember having a couple of drinks after going to Marcus's house and then nothing. Everything felt off, my skin felt weird - feeling trapped and constrained, I tired to sit up but had no power left in my limbs. "Don't worry Jessica," Marcus said, "you'll get the...
With Kind Proofing by Vickie Tern Maid to Measure, or Sissy Slave by Design, Part 3 By Mistress Kathrine The morning after Kathrine let Nikki sleep in the Master bedroom with her, she lay thinking about the things she still needed to train her pretty Sissy. Sissy Nikki didn't know anything about Kathrine's plans to marry her, and have a child with her, not yet. She decided it was time to wake her Sissy and get at least the wedding...
My first time with a guy, orally was a bit different than what usually happens with young teenage boys and their sexual experimentation, but not as much as it might seem. Growing up, next door to me was a pair of sisters, the youngest was 3 years older than me, which during this time in the story, I was 14 and she was 17 and her sister was 19. One summer day, we lost power in the neighborhood cause of a bad train wreck. Well, the sister's, their names were Cathy was the younger one and...
Maid to Measure, or Sissy Slave by Design, Part Two By Mistress Kathrine The room was very bright. It hurt to open his eyes so he tried to cover them with his hand but found he couldn't move it. He started going over carefully the last things he could remember. He was in a beautiful home, Kathrine? No Mistress? Oh if only he could wake up and remember what happened? As his mind began to clear he could start to see more clearly. It looked like he was in a...
(Note from Author - This final more polished version would not have been possible without the very kind help I received from Vickie Tern. Thanks again Vickie) Maid to Measure or Sissy Slave By Design, Part One [by Mistress Kathrine] Nick It was early on Monday morning when the CEO himself knocked on Nick's office door and asked if he was busy? Nick had never said anything more than hello a few times to the man. What was this all...
Chapter 6 - Penitence Waking up in a latex straitjacket with masters arms around me in bed, I felt a huge amount of relief. Master was here to take care of me. Waking slowly I remembered the ordeal that had been my first full day as Masters slave. The warm embrace helped sooth and recover me but deep down I still had intense and mixed feelings about what had happened. Clearly a number of people had known me at that club, some were shocked at my transformation others clearly weren't. ...
sharleesisterboyYes, Sadie, I am a 'Lil Slave Bitch' for My Big 'brother's Cock use, when He and His friends get in the Mood for Young Sissy Boy meat to strip and abuse on the livingroom floor, inside the 'Big House'! I'm f******n and have been His Secret Sissy, Piss-Whore Slave since He traded for me five years ago when I was Nine! He KEEPS Me Locked Up in a rusty, smelly old trailer, parked inside a dark, Old Red Barn. I'm Locked up inside and I sleep on an old, Urine Smelling, Stained...
I actually began this with my boyfriend during our junior year in college. I became interested in feminization, and later sissification because my older sister’s husband is a doctor who has done some work with transsexuals. I began reading books and gathering information on websites and got started by crushing up Feminique and Triple Strength Mammary and putting them in Mark’s food and drinks without his knowing. Mark had a body I knew would convert with relative ease, average weight and...
Joanne, my wife, has for many years insisted that I wear lingerie and girly things under my male clothes when at work as part of my sissy training. At home I am a sissy slave.“Sally” she said “Today we are going to make you feel more aware of the pretty things you wear”. After years of taking hormones my breasts are a nice 38C with dark brown shades round my nipples and Joanne had arranged for me have my balls and sac removed when we went to Thailand one year. Despite this and though my cock...
Hello master and mistress , I am your sissy slave Arvind alias Ananya . I am novice in story writing so please ignore my grammatical mistakes . I am working in a private firm , I am a regular visitor ISS . I really fond of gay story and submissive and feminine character story . Read many stories related to above topics and loved to be sissy sex slave to any man (masters) and women (mistress) . Let me come to the story , due to this interest I started chatting with guys to be my master and treat...
Gay MaleJohn was on his way to a conference, and had been driving North for at least four hours. The rain was pouring down on his windscreen as he continually wiped his eyes. 'I've got to find somewhere to stay', he thought to himself. After about ten minutes he came to the next exit on the motor-way. He found himself hopelessly lost in the dark countryside. 'Yess!' John had just discovered the sign for a bed and breakfast. He decided that staying the night there then getting his...
Would you be our full-time cross-dressing lesbian boislut? Of course you would. I knew that from the moment we'd made you beg to be fucked whilst dressed in a red corset, knickers and stockings ensemble. Your clothes matched those of me and my new student girlfriend, and your makeup was messed only by our juices. It was easy to make you submit after that. A hard fucking does wonders for a sissy's attitude. You moved in a week later, and I knew you were ready for the next step. We...
Pepper and I knelt on the silky sheets of the bed and studied each-other in disbelief; our cocks rigid and ready for relief. I took her sweet sissy cock in hand as I sniffed and licked at her face and neck; her skin as white and silky as the sheets. She thrust her slippery little sissy cock back and forth between my fingers as I teased her glistening little pink bell-end. Pepper panted with anticipation as she unhitched her crop top; her sweet little breasts stood firm and inviting, my cock...
Heather's SissyMy husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.I'm not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it...
Sissy slave to my house hold servant. It’s all gone with in a year, coming back to start point? I am weight 51kg comparing to my height 5.11 inch you can assume my week personality. I am working with software programmer I am earning 5 digit salaries per month; with my experience in work area I am expert in web programming and hacking websites database. I have my own flat, car every thing more for a bachelor. Sorry I forget to say my where I am from- I am from India, I am single in my flat...
Slave kissed Pepper’s pretty face to reassure her before they were both shackled and then gagged, and sat on a prominent open seat on Ayesha’s carriage, their hands bound in front of them; Ayesha loved to display her power and ownership of slaves, and would always ensure other people were made aware of it, even if the chattels were only hers to borrow. Slaves cock was in an erotic quandary as he felt the closeness of his soft sissy; bound and submissive and thinking only of how she could...
Hello Masters , Thanks for your comments , Small recap – I’m arvind , who was sexually excited after reading feminine , boy to girl transformation ,BDSM , Sissy stories . To fantasize he found guy called kamal on chat . Kamal treated me as sex slave and kamal’s girlfriend came up with a idea to transform me to completely a girl . Here part 2 starts , As per my masters and mistress wish accepted the transformation , they told me sign a agreement , it has few conditions .. they’re , 1 . I...
Gay MaleReward The next morning I woke up in my bondage jacket with Masters gently pumping in and out of me. After a slow but loving morning fuck Master came inside me and let me get ready for the day. As I was walking out of the room Master told me what I had been waiting for. "My Jessica, your performance was fantastic yesterday and you have earned your reward. I will allow you to orgasm this evening during our training session. Now go get that sexy ass ready for the day." My heart...
From the last story I got good reviews and many interested mistresses contacted via mail. Below is one special story for slave lovers. I got a mail from one of the mistress after reading my story. She mailed me asking that “can I become her slave for 2 day”. I saw that mail next day, I replied for that mail saying “yes mistress”. After that next day again I got a reply about asking my details, I sent all my details. After that she asked me for a contact number. I sent her my contact...
Glen always got k**ded about how young he looked. Even on his wedding day, three months ago, someone had called him 'the baby-faced bridegroom'. He took it all good-naturedly. After all, he was quite short and slender, and really did appear to be in his teens. At 21 he still got carded in liquor stores. He didn't get carded in bars because he never drank there. Even the neighborhood place, which was completely tame, seemed too rough to him. Maybe that was why he felt so comfortable with Leesy,...
Hello everyone ….. Vaibhav from Delhi……First of all huge fan of iss been reading erotic stories for 2-3 years…Any lady or girl, married or divorced basically any female who wants to make me their slave or any other fantasy can mail me on all the emails will be replied….I am decent boy, well mannered, educated, neat and clean and obedient slave…I love being dominated by someone and moreover if the female is much older than me and turns into a full super dominating bitch… The story I am going to...
SISSY SISTER STREETWALKERS by Throne It was a dark street in a disreputable part of the city. Cars cruised up and down, their male passengers eyeing the tawdrily dressed females who strolled along, flaunting their bodies. One car pulled up to the curb. The gruff voice of the driver said, "We're here, sissy. Get your pretty pink ass out of the car and earn me some money." "Yeah," seconded the voice of a female in the passenger seat. "My man needs his beer and you're paying for...
I had been a submissive with ever more disgusting fantasises for several years now and had acted out a fair few of them over that time.I was a manly, muscular lad who everyone looked up to and would think was the textbook "normal man".I held a professional job, steady girlfriend and a good standard of living, to the outside world, the perfect existence.Behind closed doors i had harboured a strong, submissive streak which i could simply never satisfy and a desire to be controlled and humiliated...
Honey was viewed like a new toy by her new master’s people as she was led whimpering to the ominous looking padded pole, the males jostled to fondle her soft white bottom and rubbed their erect cocks against her sweet little body at every opportunity; the womenfolk smiled with eager anticipation at the prospect of seeing a whipping; the sissies looked on with blank faces, having tasted the whip before. The males at the front howled with wicked derisory laughter as they viewed Honey’s little...
I leaned closer to the mirror to apply my lipstick, the bright red smudged across my pink lips. I needed to hurry and finish my make-up, John would be home soon enough and I didn’t want to make him wait. I was looking forward to our outing tonight. I was already dressed. My black high heel boots that came up to my knees, my black leather mini, my black cotton tank top with the word “Sissy” written in big silver letters across the front. My thong was a vinyl material that fit snug so I could...
I leaned closer to the mirror to apply my lipstick, the bright red smudged across my pink lips. I needed to hurry and finish my make-up, John would be home soon enough and I didn’t want to make him wait. I was looking forward to our outing tonight. I was already dressed. My black high heel boots that came up to my knees, my black leather mini, my black cotton tank top with the word “Sissy” written in big silver letters across the front. My thong was a vinyl material that fit snug so I could...
“I’m in the bathroom, just finishing my make-up!” I called out. He said something but I could not make it out. I stared intently into my eyes not wanting to slip up. I was using the liquid eyeliner and didn’t want to apply too much. I started thinking about my hair and how quickly it had grown. Almost to my shoulders, light brown. I had thought about going blonde or maybe jet black, that would look great with my fair skin I thought. I would ask John. I continued applying my eyeliner...
This man was Anthony, or at least that's the name he'd given me when I asked. We'd met online a couple weeks ago on a gay dating site. For a few months now I've been exploring my feminine side. Actually, I haven't been "exploring" so much as diving right in. After a bad breakup I had last year with my ex girlfriend I went on a self exploration binge and discovered I was pansexual. Shortly after coming out, I began to discover more and more about myself, such as how fascinated I was by...
It was a tough morning....I got up and walked around in a bit of a daze wondering what i had done and what would happen next.I hoped the whole scenario was a lesson for me concocted by Empress and Saskian to mind fuck me and make me realise how stupid i had been.I made tea, popped in some toast and sat uncomfortablly to watch something i can't recall on TV.About 11.15am my mobile shook violently on the table next to the sofa and beeped loudly jolting me to my senses and scaring me so my...
When Empress had finished taking pics and videos and collecting enough evidence to ruin an army, let alone one guy she sat at her laptop and downloaded all the images onto her hotmail account and sent a copy to Mistress Saskia who was sat with her."There sissy, now they are safe in our hands and there is NO WAY you can get to them or more importantly, get rid of them. You are one fucked little whore boi"Her words echoed in my head... she was right... i was screwed over...Empress rose to her...
Arrived at Master’s house , as instructed at 10.30am wearing black lacy lingerie under my normal clothes and waited nervously and excited for him to answer the door. Master soon appeared and showed me into a darkened room. Sitting, he watched as I stripped down to my undies and paraded before him like the Sissy I am, desperately seeking his approval. Knowing he would not be pleased if he saw my small girly clit getting hard inside my panties. Standing up, Master told me to pull my panties...
The black man saw the bright lights across the street advertising the adult bookstore. He felt a stirring in his groin and he pushed down on his cock. He could use a jerk off session, he hadn't cum in a few days. It was a very warm night, and the rain had stopped, leaving the smell of wet asphalt in the airHe went to the counter. "How much to go in the back?" He asked the clerk."Six bucks," the clerk said. The black man handed the clerk a ten. The clerk took the ten and handed the black man six...
The royal wedding of Catherine White and Lord Grimmson was a spectacularevent that happened after the death of the former king and the husband ofCatherine White. Arthur White the crowned king approved his mother'swedding and Lord Grimmson was made the general in the army.Lord Grimmson won many battles along with king Arthur White. Arthur Whitesoon decided to marry and consumate the marriage for the heir to histhrone. He marries the beautiful Princess Bella. The wedding was brilliantand the...
Black Man's White Pussyboy Story from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog. I let Jay into the apartment. He was looking for a one bedroom,furnished place and had called about my ad in the newspaper. I hoped torent this place quickly, then I would be full and could devote my time tosome maintenance and repairs rather than showing places. I looked...
On the bed in the guest room, Jamie lay back against the flowered pillows, feeling pretty in his pink satin nightie, his stockinged legs spread wide, and the long black vibrator pressed to the mound in his panties that betrayed his tied-back cock. He slid the straps of the nightie off his shoulders and pulled one pale little tittie out a frilly lace-lined cup. He squeezed the small sensitive nipple and took the vibrator off his already wet panties and placed it instead against his tight...
Weekend is over, but what a weekend! I’d agreed to be a sissy slave for a friend of mine, her name is Candy. I’d spent 24 hrs getting ready, full body wax, painting my nails, buying sexy lingerie and heels for the occasion, I’d never been a slave before, I would be at the mercy of Candy all weekend.I arrived at Candy’s and she was smoking hot as always, she had a perfect figure, standing 6’5 with 36” legs, wearing a red basque, black stockings and red heels. She immediately put a collar and...
Hi all ISS readers. This is bustybitch. This is my real life story and please leave your comments at my email. I provide services to both gay males and straight women and also open to a relationship. The story begins. I came into the business of gay male due to my school professors who used to bang me during my school days. I was their personal sissy slave and I was given rough treatment from them. Anyway, soon I came to realise that there were many and men out there who wanted to fuck...
Gay MaleThe Making of a White Sissy Slut When he replied to my ad online, Steven said he was an attractive, 30- something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by saying, "Well, no one's ever told me that I was unattractive." When I suggested that was because...
The Making of a White Sissy SlutWhen he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I’d said something to offend him and responded by saying, ?Well, no one’s ever told me that I was unattractive.? When I suggested that was because no one had...
Let me remind you how you came to be in this situation before you refuse. I’ve been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what really turns me the fuck on is to take something precious and submissive and to transform it into my own little...
Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what really turns me the fuck on is to take something precious and submissive and to transform it into my...
Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what really turns me the fuck on is to take something precious and submissive and to transform it into my own little...
Crossdressing