A Sissy's Long Weekend in Fairyland

My Weekend in Fairyland

Lily arrived at the station by evening to be picked up by Babs and driven to his house which was out in the country. Babs was so excited that he couldn't stop talking all the way and asked dozens of questions. Babs a youthful looking 60 year old. Greying long hair, not very tall, say 5.6 and slim built. He wore a smart but casual two piece and talked with a soft northern accent.

As we drove up to his house l could see it was detached with a large garden around the front and back with open fields. The house was very old and had three bedrooms. Babs said it was his mother's until she died a few years ago. He lived there on his own.

He drove his car along the side of the house and l followed with my bag into the house via the kitchen. Babs said he would later show me my room where l could put my things. He made a drink and sandwich for us both and we chatted until he said l should go upstairs and shower and change into something more comfortable.

I followed him upstairs to be shown a nice clean bedroom. On the bed lay a silk nightgown, slippers and several toiletries.

"After you've showered put these on and come downstairs to my living room and we can discuss further what will be happening over the next few days together. Okay?"

I nodded nervously and began to undo my bag to take out my things before going to shower. Then on return to the bedroom l put on fresh panties and bra and the nightgown and slippers before going downstairs.

As l entered the large living l heard the sound of piano music being played. Babs was sat on a stool playing a tune on an upright piano wearing only a flowery dressing gown. The room was half lit and the windows looked out over the hills in the far distance.

"Sit down dear Lily while l play you some of my favourite tunes. Just relax and take it easy."

Babs played several short pieces none that l was familiar with, except maybe Chopin. After he finished he shut the lid and minced over to sit besides me on the sofa. We talked for the next hour about our personal experiences and shared similar stories though he'd had miles more sexual partners than l'd ever had.

He was very interested in what l really wanted from the weekend and said he couldn't change me but only help me learn to be more comfortable with my own sexuality as a submissive fairy. He wasn't particularly interested in BDSM methods, unless it was something l was wanting to do. He only wanted to show me what I could enjoy as a gay sissy person.

The tests he prepared were mostly to do with uncovering my own particular inhibitions and hang ups. So by the time l was ready to go home l would hopefully feel more comfortable in my own girly skin.

The first test Babs gave me then was to see how much a fairy l was already. He told me to stand up and casually walk about the room. Then after five minutes remove my gown and continue to walk around the room for a further ten minutes. I felt silly doing this in front of this gay older man as his eyes followed my every move.

"Now take off your panties and bra and continue."

I removed the rest of my clothes and paraded naked before him. Babs slowly but deliberately opened his gown to expose his genitals and l saw his cock was fully erect pointing at me. Then l felt my loins began to automatically stir and my little clitty stand to attention.

"Ok enough little girl. Stop right now. I can see you are a true sissy from the delightfully quick response l got from you and you lost control of your little inadequate member. You walk like a boy not a sexy girl so that needs fixing. Tomorrow after a good sleep we will start on your fem dress sense and mannerisms. But for now l want you to get dressed and after a drink of cocoa you can br

So Babs made me a hot chocolate drink and I'm sure he put something in it as l began to feel drowsy as l followed him upstairs to bed. He tucked me in and kissed my forehead and wished me goodnight sweetheart. I fell into a deep sleep within minutes. I had several vivid dreams of dancing somewhere dressed in a glittering gown.

I woke at 8.30ish, mouth dry and head swimming. The house was quiet and still outside except for the sound of birds in the distance. Babs came in with a breakfast tray, which he put on the bedside table.

"Here sweet girl. Some tea and cereal for you. Afterwards shower and get dressed we've a busy day ahead for my pretty little girl."

It had already been an interesting stay with Babs and I had much to learn about being a sissy fairy. Saturday morning l finished my breakfast in bed and showered and went downstairs in my dressing gown. Babs was in the kitchen drinking coffee. He was fully dressed in a short dark skirt, black tights, pretty sleeveless blouse and 2 inch heels. There was a hint of makeup and his long greying hair was in a bun.

"Did you sleep well Hun? I heard you snoring and talking in your sleep. Don't worry you're in good company here. Have some coffee or orange."

I sat across the table from Babs sipping a glass of orange. I thought he looked more like a woman today than l'd seen him before and his mannerisms had changed in both voice and bodily movement. Was this the same person facing me? I muttered how much l liked the atmosphere of his home. Very calming and relaxed. He agreed it was to his liking. Then he said we had a lot of work to do today and the first thing was to get dressed in my own girly clothes l'd brought so he could see what l was required to help me be a better more convincing fairy.

After l finished my drink l went to my bedroom and laid out my clothes to wear. I put on my best frilly lingerie, black leather skirt, blue v neck t shirt, hung up stockings and applied blusher and lippy. I put on my blond wig and brushed it straight. I stood in front a full length mirror and l honestly thought l looked passable but not sure if Babs would agree.

I made my way back downstairs to find Babs was in his conservatory at the back of the house. He was watering many plants as l waddled into the room. It was a cloudy day with just occasional breaking in the cloud for hints of sun streaming through. Babs turned to look me up and down and said nothing about my choice attire but instead continued to water the plants. I stood awkwardly waiting. Then Babs signalled for me to follow him outside in the garden. On the patio he walked around me inspecting my clothes and gait.

"This is not acceptable sweetheart if you think your convincing then your seriously mistaken. Not that most men would refuse you as your quite pretty and your smooth slim body is very fuckable. But and it's a big BUT you need a lot of fixing.

Later today we shall look at a new wardrobe for you and go into my local town where l know the owner of a lovely fashion shop. It won't cost the earth only a hundred or so. Now go into the living room where there a few instructive videos for you to watch until it's time to go to town."

I watched half a dozen videos in the living room of Babs for over an hour. The videos were about fem wear, makeup products and procedures, testimonials from T girls etc and other things like learning how to speak, walk and be more like a woman. Nothing about sex or being hypnotized. Babs said sex and hypno was not on the agenda as they were for another time or not necessary if l'd already experienced Bambi hypno triggers and anal and oral sex.

Babs drove me to his local town still in his fem wear. I wore casual, as he didn't insist l wore fem, unless l wanted to. When we got to town we parked near the fashion shop. The lady there was very welcoming and l was introduced by Babs as his new sissy friend Lily. It was all matter of fact and l soon tried different girly outfits for the next hour.

Babs was very keen to see me in pastel shades and tight fitting to show my shape. In the end l chose and bought a pretty pink knee length dress, some inexpensive bling and a choker. Babs bought me a matching flowery shirt skirt and blouse. We left to go for a late lunch with my new outfits feeling very contented with my new purchases. After lunch Babs wanted to show me the countryside area in his car before heading back to his home.

Later that afternoon on returning to his house Babs showed me his wardrobe which had dozens of outfits of every colour and pattern. Drawers full of lingerie and bling and makeup and assortment of wigs. He opened a large cupboard full of toys of every kind and sizes. Babs was the real deal when it came to having the perfect fairytale lifestyle...except l wondered where were all the lovers in his life? I didn't dare ask or assume that was his business.

After Babs showed me all his wardrobe he told me he wanted to see me fully dressed in my new outfit. It was late afternoon and the sun had gone in as l began to undress and begin my transformation. Unfortunately he was a smaller size than me bring 12 compared to my 14. So only a few items in his wardrobe would have fitted well with my new purchases.

Likewise, Bab's heels were size 7 compared to my feet 8.5 and as l didn't have room to bring any heeled footwear l wore my black slip ones. It took sometime to make my mind up what l looked best in but l eventually decided on my new dress, stockings, Choker, blond wig, make-up and earrings. I couldn't stop thinking why Babs hadn't been interested in fucking me all the time l was with him? Didn't he fancy me or was he waiting for me to make the first moves?

I thought his ample sized cock looked very inviting when he showed it off when l walked naked in front of him. I heard his voice calling from downstairs to come and present myself before him. I nervously hold my clutch bag and took the stairway to the living room. The lights were on in the hallway leading to the living room and on entering l saw Babs in a different outfit standing in the middle of the room. Dancehall music was playing in the background.

Babs beckoned me forward to take my hand and lead me into a sort of waltz around the room. I'm a lousy dancer but he was leading me so l followed as best l could. His hand was on the small of my back and at times found it's way onto my bum. He looked me in the eye and then kissed me softly on the lips. Then l felt his hard cock pressed against my groin. We danced like that for the whole tune until it faded.

"You look lovely tonight l could eat you alive. Much much better than the dress you brought with you. Now you look the part. What reward would you like my sweet girl?"

I didn't know what to say as my head was spinning and my pussy and clitty were equally throbbing. Then l said l so wanted his cock. Please Babs please will you fuck me as I'm dying for your cock! Babs stood away from me and lifted up his dress to expose his rock hard cock and before he could say another word l blurted out the trigger:

"Drop for Cock!"

And down l fell onto my knees to gratefully receive his cock. It was so fucking nice to suck and lick him while he stroked my neck and shoulders. Babs held off cumming like a true expert and took me over on my hands and knees to his piano stool. There l laid across the stood facedown while he pulled down stockings and panties. I heard Babs walk across the room only to return with a tube of lube which he filled my pussy with. I lay waiting impatiently for him to enter me but he just fingered my hole and stroked my hanging balls.

"You really are a lovely girl aren't you sissy and true fairy like me except l'm far more your superior in more ways than one. Your tiny micro clit is sweet but inadequate and your smooth slim body is perfect for a real man to use. But you need to be tested to be a proper gay fairy. But for now l will give you what you desperately ask for which is my cock."

For the next three hours Babs fucked me all around the living room cumming and cumming and cumming. I must have looked a complete slutty mess by the time he'd finished with me as his bitch. It was past 9 pm by he time l went to shower and Babs went into the kitch to cook us a late supper. After l showered l got into my dressing gown and went to the kitchen to eat. We spoke very little throughout the meal and only afterwards did Babs say he enjoyed "our little dance".

It was time for bed and so l left the kitchen and went to my bedroom. I didn't fall asleep until after midnight. I could hear Babs talking on the phone laughing with someone at the end of the phone. I wondered if he was laughing at me and what he'd put me through. I fell asleep for three hours to be woken up by Babs who was lying naked alongside me. He was fully erect and he entered me once again and fucked me for another hour!

I fell into a deep sleep with him on top of me. When l woke again four hours later he was no longer in my bed. It was just before 9am when l heard the sound of his car reviving up outside. I looked out the window and saw Babs getting out of his car. I got dressed and went downstairs to the kitchen side door to see Babs was getting out of his car. He no longer was wearing fem but a instead a grey track suit. He wished me good morning and said whether l was ready to go home after breakfast. He looked in a hurry to see me off.

We had breakfast and then l packed my things and put the bags in his car ready to be taken to the station. Babs said before leaving he enjoyed having me and showing me the ways l can improve as a fairy. I asked if we could meet again to continue in some way. Babs replied it was possible l could return at another time. I got that distinct feeling Babs was not committing himself to future meetings. So l asked him what he liked and didn't like about sissy Lily. He was brutally honest about my undersized clitty and my lack of feminine finesse but he liked my pussy bubble bum and my fair haired pink skinny body.

We kissed on parting at the railway station and waved goodbye. Maybe we will meet again or maybe not. l don't know but it had been a nice weekend in fairyland.