Making Dreams Come True

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Writer345
Writer345
181 Followers

Between us we had made quite a mess on Mom's bed, but if her look of triumph was anything to go by; she didn't mind. After we returned from her bathroom where we had cleaned up we slipped into bed with her and cuddled up to her. "That's enough for tonight." She said languidly. "We'll play lots of new games together in future, but Mommy's tired now..."

I remember drifting off to sleep that first wonderful night hoping that Tilly was as happy as I was.

  1. Tilly's Awakening.

I used to by Timothy but Mom has had my name changed to Matilda, or Tilly for short. I used to be a boy and a weedy one at that who was pushed into the background by my beautiful twin sister. Although she tried not to show it, it was pretty obvious that Mom preferred Saffie to me. I wasn't jealous: honest, I wasn't, and loved my sister as much as we both loved Mom.

Okay, as Sapphire has said, she wasn't really our Mom: but she had raised us after our parents had been killed. She was our only relative and like everyone else who lived in the Chilterns, seemed to be rich.

We were eight when we moved in with her: our nanny, Concita, came too and it was really her that had raised us... Mom just paid the bills. As I got older, I realised that I wasn't like the other boys that we met occasionally. I was always small and girlish for my age, and my voice never broke. Concita seemed concerned but Mom wasn't and kept reassuring me by saying that I was a late developer.

We went to a small, very expensive private school were most of the other pupils were girls. When I commented on this, Mom just shushed me and asked me what I'd got against girls?

It was a gentle and sheltered existence, far from the rough and tumble of the local Comprehensive School. We had each other for company and a twelve acre walled garden to play in but above all, we had Mom and Conchita and a bevy of assorted maids to care for us. We were happy, mainly because we were sheltered from anything that could make us unhappy so I suppose that our childhood could be described as idyllic.

I say that we had Mom... This was technically untrue because Mom had us and was not going to let us go: besides, where would we go to? The outside world was a big, scary place that we were not equipped to deal with so why would we want too?

The years drifted by, Saffie blossomed into a beautiful young woman while I didn't really change besides getting taller. We didn't want for anything material and before we knew it we were eighteen and were told that we were adults in the eyes of the law. Our eighteenth birthday party was odd: no presents for a start, Previous parties had been attended by carefully selected school friends, although the events had been carefully stage-managed.

This birthday was different: there was just the two of us along with Mom and Concita... An increasingly grumpy Concita at that. It was after our afternoon tea that Mom dropped her bombshell and threatened to turf us out into the big wide world so that we could fend for ourselves.

It had taken a few minutes for the enormity of the threat to sink in... We could take our trust-funds, walk out through the front door and take our places out in the real world where we would sink or swim in what ever was out there.

Or.

We could stay with Mom: we could work for her at her bank and become exactly what ever she wanted us to become.

Only thing was, if we left: that would be it! There would be no coming back.

We just sat there in shock. Why was she doing this too us? Why was she throwing us out?

Concita glowered at her. "And just how will the poor darlings survive out there?" She demanded. "It's not as if you've prepared them for life... This is so wrong!"

Mom shushed her. "They can stay on my terms. It's up to them."

Saffie broke our stunned silence. "Can Concita stay too? You are not throwing her out are you Mom?"

Mom chuckled. "Oh, Concita is staying: I wouldn't dream of letting such a treasure go. Who else could run our household as efficiently as she does?"

Concita seemed to shudder but Saffie didn't notice, instead she looked at me.

"Timmy?" My sister asked.

"I'm staying with Mom!" I said as emphatically as my little-boy voice would allow and that was that.

Mom was as good as her word and we both stayed on her terms... If I had known in advance what those terms were, would I have been so eager to stay? How can I answer that? It wasn't a choice, was it? Before a choice can be made there must be alternatives presented. Mom didn't do that! Oh sure, it looked like a choice but it was more of a manipulation. We wouldn't go: Mom made sure of that. And as for Concita, well she knew too much and she would be staying too. The three of us were staying but on Mom's terms.

She changed us alright: she recreated us both in her image and we became a special family: a shemale and her daughters.

After our stay in that Indian hospital Mom took us in hand and guided us expertly as we awoke to our new lives: lives that she had ordained for us sometime in the previous ten years. She loved us but was determined to see a return on her investment while we had gained a purpose in life, it was now our sole function to make her happy in anyway that we could.

We had our own room which we shared with Concita, but when Mom was home, we usually slept with her in her massive (triple) bed and it was here that she awoke our new sexuality.

I remember the first time: we had only been back home for a few days when she sent for us; she'd already played games with us and explored our bodies: I remember her masturbating me for the first time. In my enforced innocence, I hadn't realised that it was possible and nothing prepared me for the feelings and sensations that coursed through me as the world inside my head exploded into light and pleasure for that first time... Now it was Saffie's turn and Saffie was the first one to be taken by Mom.

The bedroom lights were dimmed when we entered and romantic music was playing in the background. Diner had been informal and we had sat around the table chatting until late and drinking more wine than was good for us. We weren't used to it and my sister and I were giggly as we were led, hand in hand, up the wide staircase into the 'Mistress-Bedroom'. I suppose that that should have read 'Master' but the word was totally inappropriate in every way imaginable.

Even before Mom eagerly pulled us in through the door she had begun to almost rip our clothes off with a burning urgency that was born out of impatience and frustration. We left a trail of clothes in the hall way and on the bedroom carpet. Mine; Mom's, Saffie's all jumbled up and not needed. Then, slipping an arm around each of our waists, she propelled us towards that massive bed with its silky-soft sheets and covers. With my head spinning from the wine I needed no encouragement to scramble up and climb under the covers,

"No, Tilly, not tonight." Mom murmured softly. Her husky voice quaking slightly. "I want to see your beautiful bodies, I want to enjoy the sight of them as I take possession. Tonight is when all of my dreams come true."

She encouraged Saffie by positioning her on all-fours, on hands and knees; stroking my sister's flawless and hairless skin as she did so. Saffie giggled as Mom moved her knees apart and knelt behind her.

"Tonight I'm going to pop your cherry, my darling." She purred as she began to ease something into my sister's tight little rosebud. "Don't worry, my pet, its just lubricant: I want to make love to you, not hurt you."

She encouraged me to sit in front of Saffie so that I could watch whatever it was that Mom was going to do.

Saffie looked a picture waiting their, unsure as to what would happen next, her breasts hung down as did her willy. All three jiggled every time that she moved. I couldn't see Mom's as she was kneeling behind my sister's raised bottom but I could imagine it growing hard.

Then it began. She slipped a beautifully manicured finger into my sister's arsehole which caused her to gasp in surprise it also caused her little tool to stiffen.

"Ooh!" She moaned as Mom reached down and grasped herself.

I didn't know it at the time but she was about to fuck Saffie... Tonight it was her turn; soon it would be mine. She jiggled around and then suddenly grasped my sister around her waist and eased forward.

"Ahh - Ahhgh!" Saffie gasped as she was entered, her eyes bulging wide. Was she in pain? Was Mom hurting her? Should I do something?

Mom eased back, then moved forward again which caused Saffie to give a little barking gasp. Mom's face was ecstatic, no, it was triumphant, as she began to thrust rhythmically. Slowly at first, then faster and faster. Saffie's tits and cock began to swing backwards and forwards in time to those loving thrusts. Saffie's groans changed to grunts and then into moans of pleasure which kept times with Mom's urgent thrusts. Pull back slowly -- slam forward. Pull back slowly -- slam forward. Pull back slowly -- slam forward. Each thrust accompanied by a moan, or a gasp, or a squeal. All of them, none of them.

Saffie's eyes were wide and unseeing as each meaty slap of Mom's thighs against her arse sounded against the background music and elicited a gasp from my sister. Then, like poetry in motion, Mom's magnificent tits swung backwards and forwards, jiggling in time with her thrusts, just as Saffies smaller ones and her cock did.

Suddenly Saffie squealed and squirted her load down onto those beautiful silk bed covers in one single long jet. Mom carried on with her rhythmic pounding for perhaps another half a minute until she screamed. "Oh Fuck! Oh Fuck! Oh Fuck!" as she herself orgasmed and collapsed across Saffie's back.

The three of us slept until late the next morning oblivious to the mess that we had made of the sheets. Yes, I say 'we' because I joined in taking my little willy in hand and wanking myself off in time to the pounding that Mom gave Saffie and I added my little load to the general mess of that wonderful night. Mom had popped Saffie's anal cherry and I had played with myself as I watched.

Two nights later it was my turn. Mom's approach was the same: wine and then bed upon which I found myself perching on all-fours waiting for Mom to enter me. My head was spinning from the amount of wine that she had encouraged me to drink.

"It'll relax you, my darling." She had said.

Maybe she was relaxed enough for she hardly drank any herself.

Then with Saffie sitting in front of me in exactly the same position that I had occupied, we smiled at each other... God! My sister really is beautiful! I didn't quite adopt the same posture that she had, instead, I rested on my forearms, rather than my hands.. This had the duel affect of forcing my arse even higher and bringing my head down almost onto Saffie's crotch. For some reason I ducked down and kissed the end of her girl-cock. I don't know why I did it -- it just seemed to be the right thing to do.

Suddenly I felt something cold being squirted against my rosebud as Mom applied lubricant and then worked her finger into me to make sure that she had used enough. I gasped because her finger really did feel massive. I guess that I must have wriggled because I felt my breasts move: I still wasn't fully used to their weight hanging from my chest: they really did seem huge when compared to the previously flat-chested me.

Next I felt Mom's hand slip down my thigh and gently move around and under my belly. Her finger tips traced an intricate pattern, which made me shiver expectantly, before they came to rest on my little girl-cock which they gently fondled and caressed.

"Oh Tilly, Tilly, Tilly, you are becoming hard aren't you?" She purred as her fingers rippled. "You've got a little stiffy."

The hand stroked and squeezed lovingly. She grasped my little organ and masturbated it gently for a few seconds before moving on to fondle my little balls in their hairless sac. I gasped.

Then she let go and I felt something being rubbed up and down the crease between my arse cheeks as Mum pressed the end of her now hard girl-cock against me. I must admit that I enjoyed the sensation.

"Relax, my beautiful girl." She hissed as she lined herself up. Then it began. She entered me. The stab of pain was really unexpected and cause he to squeal.

I had a virgin arse-hole -- nothing had ever forced its way into me before so this was a completely new sensation. Mom pushed into me further and further and her girl-cock felt massive. Hell, I had no idea how big cocks could be... Mine was just about three inches long when angry -- Saffie's being about two and a half inches longer and quite a bit thicker too.. Mom's, needless to say, was bigger still and seamed to take for ever going into me. It really seemed as if I had been filled beyond bursting point and I felt as if I needed to relieve myself, only how? Surely something inside me would tear apart?

Suddenly I felt something else enter me. My mouth was only inches away from Saffie's willy -- only it wasn't any more and I felt it grow erect and the bulbous end rubbed against my tongue. As Mom thrust forward again I gasped and drew it further into my mouth.

Mom's arms hugged my waist as she thrust her way in before pulling slowly back. She was gentle at first allowing my newly stretched arsehole to get used to the intrusion.

Each thrust hurt but I soon realised that their was another sensation -- it was nice; I felt as if I was being massaged on the inside.

As Mom thrust in again and again then I felt Saffie's fingers lock into my hair as she took control of my head. Mom thrust herself into my arsehole while my sister thrust herself up into my mouth and I felt myself being fucked at each end simultaneously.

Mom rammed into me with increasing power while Saffie worked her girl-cock in and out of my mouth. If I had been thinking at this stage I would have been confused but instead I felt a warm glow spreading out from my bowel. The stabs of pain were still there, but they didn't matter any more: all that did was the glow and the pulses of pleasure that went on and on, a pulsing glow that I didn't want to ever end. Mom's cock only existed for one reason, and that reason was to give me pleasure.

The pounding went on for several minutes and I felt the tension begin to build up inside me until it exploded and I could feel my own little cock begin to twitch and jerk rhythmically as I orgasmed and it released its load in a series of squirts down onto the bed.

Mom speeded up getting faster and faster until a warm something flooded out into my bowel stretching it even further. As Mom orgasmed, shrieking as she too shot her much larger load into me in pulses of liquid fire as her cock twitched and throbbed inside my bowel and then she paused and I could actually feel her penis soften inside me before she pulled it out a minute or two later. Finally Saffie came into my mouth as she shot her slimy and rather earthy tasting load into it. I remember swallowing as I heard her too squealing in ecstasy. We had satisfied each other -- life was indeed wonderful.

Again we ignored the messy bed and fell asleep nestled in each other's arms. Mom was happy, my sister was happy so I was happy. What the two of us kids lacked in skill and experience we more than made up for with youthful enthusiasm. We had discovered sex and planned to let it take centre stage in our new life with Mom.

  1. At Home to "The Circle" (Saffie).

On every third Thursday afternoon of each month Mom was "At Home" which is a quaint, old fashioned term that means that the mistress of the house is in residence and happy to receive visitors. However the visitors are rather special: they are all women and are members of what is referred to as "The Circle".

Ever since we were little when Tilly was Timmy, we had known about these rather formal visits by Mom's smartly dressed friends and acquaintances. They always gathered in Mom's drawing room, the one next to her library, where they sat and exchanged pleasantries and engaged in small talk or so it had seemed to us as children.

Actually, as children, our interactions with these gatherings had been strictly limited. When not at school we had been paraded, freshly scrubbed and neatly dressed, before the gathered ladies for them to admire. As we grew older, we assisted by helping to serve tea, small sandwiches and tiny cakes to the assembled group receiving compliments as to our behaviour and appearance in exchange. Then while 'afternoon tea' was in progress, we were always spirited away by Concita and given tea and cakes in our sun-lounge.

There were never less than four women in attendance and never more than about a dozen but as our contacts with the group was limited they never seemed to be more than Mom's friends. As the years passed by we noticed that sometimes one or more of the women would be accompanied by younger companions who seemed to stand or sat quietly while playing no real part in the proceedings. Other than that the gatherings were just part of our normal life at home.

It was only after our eighteenth birthday that we found out just what "The Circle" represented and just what the women who belonged had in common, however, the realisation came in stages. Mom had explained human sexuality with the emphasis on the parts that were relevant to us: we knew how 'shemales' differed from 'biological females' and how 'lesbians' differed from 'straight women'. Mom wanted to avoid the complications that would be produced by us trying to force ourselves onto one of the latter. Although she needn't have worried as we were both very submissive and shy: she had seen to that and had explained that it was for our own "protection".

Well the women of "The Circle" were all gold-star lesbians: wealthy and influential ones at that. A few were also shemales or transwomen, but the majority had been born female -- not that it seemed to make any obvious difference who was what, I guess women aren't as judgemental as men.

"The Circle" was formally-informal and did not have an official membership list or even leaders. It was a de-facto group that existed to protect and serve its members and to facilitate them in their pursuit of the lifestyle that they chose to enjoy. As time went on we became acquainted with them all, although I hesitate to claim that we knew them. Mistresses are far too self-contained and controlling -- they made sure that no one really knew them or at least knew no more than the false front that they presented to the world in general and to each other in particular. But above all they kept each other's secrets: the greatest of which being that they existed at all.

As I have said, the non-group did not have any leaders: leading a group of Mistresses would be akin to trying to herd cats! However two of the most influential leaders that they didn't have were Mom and a woman named Margaret Baxter. Mom held sway by reason of her being a banker and as such was in a position to safe-guard the others financially and to make sure that their funds were always invested in the safest funds that produced good returns. Margaret Baxter was a consultant psychiatrist and an eminent one at that: when she spoke, she spoke quietly and with such authority that the others always listened. Like Mom, she tended to be a moderating influence which is the sort of thing that every group of over-confident and egotistically lesbian slavers needs if its members are to remain at liberty in a homophobic world that pretends to place the rights of the individual above all else or at least to pay hypocritical lip-service to it.

The first "at home" that my sister and I attended was about six months after our birthday: Mom wanted to be sure that we were comfortable with our modified bodies, our altered genders and our revised sexuality before exposing us to the full glare of her 'friends'. Margaret Baxter had visited a couple of times and we had got to know her as a friendly, if quietly spoken, middle aged woman. She talked to us in depth over tea or while just relaxing and always seemed happy to listen to whatever came into our empty heads. She really was a nice lady.

Writer345
Writer345
181 Followers