Tomorrow Was My 25th Birthday

This is the continuing tale of a young boy and his development into a sissy by his Aunt and family, includes incest and some BDSM. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... otherwise enjoy.

Please leave honest comments or suggestions, it really does encourage those of us who write to continue...

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Once she had left the room I struggled briefly, testing the cuffs, all to no avail she had made sure I had little movement and that I was not going anywhere.

I could hear laughter from downstairs, and conversation, and I suddenly felt very alone, what was to become of me, I was sure Auntie had plans for me but no idea what they were. No doubt I would be told when she though I needed to know. Right now all I knew was that I would become the family sissy and that I loved Auntie and will do anything to please her.

As I listened I heard footsteps on the stairs, more than one set, then giggles, and whispers, it seemed that the family was coming to see their new toy. As the door opened the whole family came in Auntie, Mother, Sally, Jane, Jessica and a total surprise Matthew.

I struggled hard not wanting Matthew to see me like this he was my best mate from school and deep down I wanted him to remain friends. Auntie said "We hope you don't mind but Matthew having seen your panties the other night called round, think he wanted to take you out on a date, so we asked him to stay and watch your initiation."

I am sure I blushed so red, but little I could do, as he had seen me tied out like this, cage locked on, in my frilly nighty, not a lot could be worse could it. As I looked at him, he smiled at me, I also noticed a considerable bulge in his trousers, he was excited by what he saw.

Auntie came over to the bed and sat beside me, She gently stoked my hair as if to sooth me and I did enjoy her touch. She gave me a pill, "Now take this, from now we will be doubling your hormone dose, this will speed up your body changes and make that thing in its cage shrivel and become useless." I swallowed it.

"Pricilla," she said, "you need to know more about your family and you new situation. As I told you your duty is to submit to all of us as the sissy in the family, and it seems that Sally has taken a shine to you so she will provide most of your training."

I groaned inside as I could tell from the grin on Sally's face that this was not going to be good for me.

"However tonight," she continued, "is to be your initiation. The family as a whole is either lesbian or bi-sexual, and we include Matthew, and it will be your pleasure to serve us all now in whatever way we enjoy." She smiled down at me, leant over and kissed me on the forehead as you would a little girl.

As I turned to look at the family, Mother had started to undress. I didn't remember see her naked for many years. As she took her skirt off and then her blouse she exposed her mature body in a sexy basque with suspender belt, stockings and what looked like french knickers. She got Jessica to undo her suspenders then loosen the lacing on the basque so that she could undo the basque revealing heavy pendulous breasts and a little fat around her middle. As she slipped her knichers off, an extremely hairy pussy came into view, and she started rubbing it. She moved over to the bed, looked down at me, "I have waited a long time for this my darling girl."

She signalled for Jessica and Jane with her hands to come to either side of the bed and she climbed onto it, facing my feet, straddling me. She held the girls hands to steady herself and then slowly bent at the knees, lowering herself down onto my face, I watched in horror and amazement and I saw her hairy wet pussy coming down on me.

Horror because she was my Mother, amazement knowing that she wanted to smother me and no doubt wanted me to lick her to an orgasm, it was something I had done at university with a girl I knew, but never with a member of my own family.

With an agility that surprised me, she was soon sitting on my face and smothering me with her fat hairy pussy and ass which was already wet from her ministrations. She lifted a couple of times to spread herself more, my nose was buried now in her pussy and she wriggled about obviously wanting me to lick her asshole which I did.

While I was surprised by her actions I did what all good sissy bois did and started licking her, her aroma was strong but exhilarating, and as she ground down on me I struggled for breath but she seemed to sense this and lifted so I could get a breath before coming back down on me.

She was obviously being watched by the others when she said "I don't know where she learnt but she is a good pussy and ass licker." Her breathing was getting heavier as she moved on my face, my tongue buried as deep as I could get it in her, I started to enjoy the pleasure I was giving her, although my mind was in turmoil, was this right, she was my Mother after all, but it was not an option to stop, so I did my best.

It was during these thoughts that she orgasmed. I had heard of women that squirted when cumming but I was not prepared for the gushing that came from her pussy, and I had no option but to drink her juices, while a lot of it went onto my nighty soaking it.

The rest of them laughed and clapped as they saw Mother cum, and although I could not see it I was sure she would have a smile on her face and she slumped down on me cutting all air off, making me wriggle and struggle to grab a breath.

She suddenly realised she was smothering me, and rolled off me, I was a mess my nighty was soaked, as was my face and hair all covered in her juices.

She went and sat down at my dressing table and turned the chair so that she was facing the bed. Auntie then simply said "Jessica, Jane your turn now."

Both of my sisters stripped off in record time, Jessica was very pale and skinny, her breasts were not a lot larger than mine, a B cup perhaps, but unlike Mother her pussy looked very tight and was totally bald. Jane on the other hand carried a little more weight, she was not fat by any means but she her breasts were probably a D cup, I was quite good at judging from my experience in the shop, and she had much wider 'childbearing' hips than Jessica, she also had a bald pussy.

They looked at each other and giggled. Then Jessica climbed onto the bed and sat facing me, her pussy sitting on my cage, she then leaned back exposing her pussy to me. Jane climbed onto the bed and sat with her ass toward me and leant forward, moving her pussy onto my face so I could reach her with my tongue, and although I could not see I was sure she was licking Jessica as I excited her.

As she licked Jessica I felt her tongue probing through my cage, teasing me as well as Jessica and I realised that being in this cage would be at times like now very painful as I so wanted to get hard but could not, it did not stop my cock trying to get hard. I groaned as she teased but continued to probe her pussy with my tongue. Auntie said "Don't worry sissy, the extra hormones in time will take away your ability to want to get erect."

After about ten minutes the girls swapped places, both of them were looking flushed, and we continued until both of the girls came, sadly without any relief for me.

All this time the others had been watching intently, Matthew obviously had a hard on, and judging by his bulge in his pants he was quite a big boy, I have never seen him naked, but suspected I would soon, and never having had a cock or been with a man before that worried me, but Mother and the girls so far had taken my mind off it.

Auntie had pulled a chair up to the bed and was sitting with her legs apart, the show so far had obviously excited her as there was a damp patch in her knickers, satin ones in blue.

Sally was leaning against the door, a smirk on her face, and I wondered what she had in mind for me, I was getting quite worried about her as she seemed for some reason to have taken against me, and I had a feeling I was going to suffer when she had me alone.

Auntie it seemed was to be next as she got up and started undressing. She was a stunning lady, just 30 years old, very fit as I knew she worked out, and as she undressed I admired her firm belly, her breasts a C cup with very hard looking nipples, and the v of her groin, like the girls, was totally smooth, but with a protruding clitoris and hood. She also have quite fleshy labia and with her panties pulled tight had a lovely looking camel toe.

As she pulled her panties down I noticed she was wet, evidenced by the patch on her knickers, and it was glistening. Fully undressed she leaned forward and pushed a nipple into my mouth which I circled with my tongue feeling it get harder before taking it gently between my teeth and nibbling on it. She gasped, and I realised that her nipple were obviously very sensitive, and when she pulled away she presented me with the other one.

By now my tongue was getting tired but I did my best to pleasure her, I so wanted her to be my teacher in this journey of mine to feminisation. Shortly she climbed on to bed and sat on my face so I could lick her to orgasm, which surprisingly did not take long, I think all of us there were extremely turned on by the whole situation, I know I was although tied as I was and caged there was going to be little I could do to get relief for myself.

She climbed off me and gave me a kiss, pushing her tongue into my mouth, then moved away saying "Thank you little one."

When I looked sideways at the others I saw Sally was rubbing her crutch and was obviously very aroused, and Matthew had unzipped his trousers and had his cock in his hand, I didn't realise men could be that big, he was thick and at least eight inches long, his foreskin pulling back and showing his head as he stoked himself, he had a big grin on his face, I suspect as he knew he was going to use me soon.

Auntie motioned to him and he stood up, approaching me, his cock advancing towards my mouth. I tried to struggle and get away but my bonds held me there, and in no time his cock was at my lips. I kept my mouth shut breathing through my nose, but he just grabbed my nose and squeezed it shut forcing me to open my mouth.

As his cock pushed pass my lips he smiled down and just said "Lick me my sissy boi." I tasted his precum, it was not nasty and I circled his cock head, licking gently, tasting him as I tried to remember what it felt like when a girl had done this to me, he pushed a little more in me and groaned as my warm mouth took a couple more inches.

I opened wide as I could and a couple more inches entered and I was then starting to choke, but her reassured me, telling me to relax it would be ok, holding his cock at the back of my mouth till the gag reflex subsided a bit, then he pushed further.

He took his time withdrawing then pushing back in and it was not long before he was fully in my mouth and throat and I could feel his balls on my chin. "She is going to be such a good cocksucker." He declared as he started to slowly fuck my mouth.

It was not long before he was groaning and increasing his pace, ignoring now my gagging he held my head and pushed in and out of me only interested in getting to satisfy himself using my mouth. With a major push and a grunt I felt him unload, his salty cum hitting the back of my throat, I had no choice but to swallow what he was injecting into me.

As he withdrew, still with that stupid grin on his face, the whole room clapped and laughed, and congratulated me on doing so well.

All I could think about was that I had just taken my first cock and it was not so bad, and that there was only Sally left to please.

Once the hubbub had died down in the room Auntie said, "We had a draw earlier which Sally won. She will now spend the night with you as your first night being a sissy. She has my authority to do whatever she pleases with you, have fun kids." And with that she ushered the rest of the family and Matthew out of the room, shutting the door behind her.

I was worried now, it seemed that Sally did not like me or what I was to become and when she went to the door and locked it taking the key out and grinning at me she dropped the key into her jeans pocket, I knew then this would not be a good night for me.

She sat on the side of the bed and released the cuffs holding me spread eagled, and then shuffled down and released my feet. She told me to sat next to her which I did, and she grabbed me and kissed me hard, her tongue immediately pushing itself into my mouth exploring me, I could not help but respond and as she pushed me on my back we were still locked together by our lips. Perhaps it will not be so bad.

As we kissed she grabbed my cage and played with me, getting me excited again and I groped her breasts through her top, feeling her hard nipples. She broke off briefly saying "Take my top of sissy." Then she went back to kissing me. I struggled to get her top off, she was wearing a training top and training bra, those that are tight and stop her breasts bouncing when exercising, and when I eventually got them over her head I was surprised how large her breasts were, very firm and a D cup, and she had a six pack from all her training.

I thought about it as she pushed my head down to her breast, she always dressed like she was ready to train, or else in tight jeans and tight tops, almost like she was trying to suppress her obvious sexuality, I guess as a lesbian and built as she was she wanted to project herself as the dominant party in any couple.

As I circled my tongue around what I can only describe as a fat juicy nipple, only to find that she was pierced with a bar, I found that odd as I have never licked a nipple with metal in it, and I played with it with my tongue, while Sally kept dragging her fingernail across the head of my cock in its cage, making me very aroused but even more restricted. I thought then it would be a long night if she kept on teasing me.

She as pushed me to her other nipple I had to move myself to reach it, and then suddenly I felt her finger at my anus, putting a little pressure on my ring. I tried to concentrate on her nipple when she entered my ass, I gasped partly with surprise but also because no one had entered there before, but she just held my head and pushed me back onto her hard nipple.

As I licked and sucked I could feel her moving her finger inside me ass, it was not unpleasant so I carried on with my sucking, that was until she pushed a second finger in and started to use both to widen and stretch me. This was a bit more uncomfortable and I lifted from her nipple and said "Sally please don't do that."

She laughed loudly replying, "You better get used to it sissy, I will be using it a lot and I know Matthew wants a piece of your ass, you will learn to accept it, you wanted to be a girl, and girls get fucked all the time, and this" she roughly spread her fingers in me "is your fuck hole, your pussy for those that want it, better get used to that bitch."

She pushed me back to her breast, and I automatically started licking again. How could my sister be so nasty to me, was it just she had something against men? I didn't see why with me now, I was hardly a man dressed as I was in this nighty, in my cage, and sucking on my sisters breasts.

Suddenly she pushed me off her looked at me hard and stated in a matter of fact voice "Sissy I am going to break you, by the time I have finished with you, you will do anything, and I mean anything, to please me and anyone I choose to use you in any degrading and humiliating way they wish, you will be my personal slave, just eager to please to avoid the pain you will suffer if you disobey me."

With that she pulled my nighty roughly over my head so I was sitting there naked next to her. She reached under my bed and pulled out a bag, not mine, she must have put it there earlier. "Now do as I say or it will be worse for you."

I was scared now, I thought I knew my sisters but Sally was not what I thought, there was no sibling love with her, she seemed to hat what I was and what I wanted to become, and I was not sure how I could get away from her, she was stronger than me, the door was locked, should I scream, but that would be hard to explain as nothing bad had happened so far.

She opened the bag and dug in it, and came out with a pair of vicious looking nipple clamps, sprung with metal with teeth that clamped the nipple and a screw arrangement that could be tightened when fitted.

Smiling she pushed me back and straddled me, pushing my arms under her knees, effectively immobilising me, she pulled on my nipple before slipping the first one on, and then the second one, they were connected with a chain. The immediate pain made me cry out and she smiled down at me before using the screws on each to tighten then till I was crying out and wimpering, I had always known my paid threshold was quite low and this was not enjoyable at all.

She grabbed a large ball gag form her bag and lifting my head forced it into my mouth before fastening it as tightly as she could behind my head. "That is so you don't wake the house when you start screaming."

She then turned the screws a bit more on my nipple till I was crying and thrashing around under her trying to get away. She just held me firm looking down with that same evil grin on her face, before slapping me across my face and back again to clam me down. The pain was subsiding a bit and I looked at her with hate in my eyes, and tried to mumble into my gag "What have I ever done to you?"

She climbed off me, and lifted me, throwing me down onto my front, causing another wave of pain through my small titties, and then she grabbed me by the waist lifting my ass and bending my legs so I was in a head down ass up position.

As I was trying to cope with the pain, she took a length of rope securing my wrist to my ankle, and then repeated it the other side before sitting back admiring her handiwork.

"Now that is the best position for a sissy to be in, the only useful bit of you exposed and available." She stated as she pushed her two fingers back into my ass. As she moved then around obviously trying to stretch my hole she said "My god your tight, I am going to enjoy this, but I doubt you will much." A third finger joined the other two and she continued to work them to stretch me.

She then withdrew them and reached round to turn the screws another turn making me scream into the gag. I felt her move away and off the bed, only to return shortly to the side of me so that I could see that she was now wearing a huge strap on, it was obviously double ended, one end buried deep in her pussy, then other soon to be in me. It was as big as Matthew had been, eight inches and fat, curved from the base of the holder round her waist, the tip had a small hole in it but it looked so big and I shivered knowing what was to come.

I mumbled into the gag trying to say don't or be gentle but she just looked back at me with a lustful look ignoring what I was trying to say, this was just about her and her power over me, what could I do but let her rape me, my own sister.

She moved behind me, and grabbed my hips, placing the strap on at the entrance to my virgin hole. I felt her spit on me, and then she was rubbing the dildo against my tight hole, then there was pressure as she pushed, it increase and I felt myself opening slightly, then there was an intense pain as she breached my sphincter and she entered me, pushing as hard as she could while holding my hips to stop me trying to move away from the pain.

I cried and sobbed and tried to scream as she withdrew only to thrust in again, a bit deeper this time, and she continued without regard to how I was feeling. As she got it deeper and deeper, I was in more and more pain, I was sure she had split me in two, at least that's what it felt like, but she just continued, building up speed as well now as she fucked me in my virgin hole. I could hear her grunting as the other part was thrust inside her every time she entered me fully, and it was not long before her breathing got heavier and heavier as I realised she was getting herself to an orgasm.