My Jottings: Little Sissy’s Vacation

This is a recent jotting and as the previous events may not be clear, as they are now in last year’s notebook, I will give the initial background once in this notebook:

I own a town house - in Prince of Wale Terrace, London with a view of Hyde Park - and I advertised at the art college, which stands a few streets over, that there was a spare first floor available for a student with a fairly cheap rent for London. The floor has enough space for a smallish art studio, a sitting room and a large separate bedroom and bathroom. I wanted some company, as I am away abroad for business a lot and never have had a chance to settle down, so sharing with someone who was also interested in art who I could chat to and share dinner with, on occasion, was the aim.

I did get a lot of interest, as you can imagine, due to the location and the surroundings but in the end I am sharing with Emma - who is 25 and is an art student studying fine art at UCL. Emma is now in her third year and has shared with me these last nine months and has somehow become my little sissy girl who likes to make cummies and calls me “Daddy”.

The following happened just before I left on another trip abroad with a whirl of meetings planned and a number of happy customers – I deal in analysing data on companies, trends and market movements and rearranging that into useful actionable information and this is how I can afford my lifestyle at 35 - but that is by the by:


‘Come into the main sitting room Emma’ I shouted as I faced the open door.

‘Coming Daddy!’ Emma trilled as she bounded up the stairs and through the door, dressed in a pink corded and pleated silk and lace dress, white lace hold ups and cute pink Mary Jane shoes. Her luscious dark brown hair swinging in its ponytail.

‘That is me almost ready to go on my trip to New York for the weekend’ I told her.

‘Can I not come with you?’ pleaded Emma pouting.

‘No! I have a lot of meetings scheduled in and there is a fair bit at stake, I can’t be distracted – even by someone as lovely as you. Besides, you have chores to do here and I expect them to be all done before I get back - or you will need to be punished. Is that understood?’

‘Yes Daddy, I am a big girl and promise to do all my chores.’

‘Good. You know, you have been very well behaved for a few weeks.’

‘Thank you Daddy!’

‘So good, I bought you a small surprise for the weekend.’

‘I love surprises. Where? Where?’

‘Look under the middle window dear’ I suggested as I stepped aside.

‘Oh Daddy! Is it all mine?’ she squealed as she saw the thick six inch pink dildo mounted onto the wall with a pink ribbon in a bow tied around it.

‘Yes, as you have been such a good girl I thought I would let you have a little fun this weekend.’

‘Thank you Daddy! I love you!’

‘I know darling, I love you too and I want you to use it to make cummies for me before I go’ I ordered as I kissed her cheek.

‘Ok Daddy! Can you help me get undressed?’ She said quickly turned around, so I could pull down the zip of her dress.

I enjoyed the view as I pulled down the zip, exposing more and more of her tanned smooth skin until she was able to step out of her dress and she then kicked off her shoes. The lace edged pink bra was next as she unclasped it and let it fall away exposing her pert breasts.

Then the plain lace edged cotton panties were slipped delicately down her long shaven legs and off onto the pile of clothes on the floor.

‘Leave your socks on,’ I stated as I took in her smooth shaven body, her pert breasts, her gorgeous hazel eyes, her smile, the sexy knee high white lace hold ups and her cute soft two inch sissy clitty.

‘Yes Daddy,’ she answered as she leaned in for a hug and a kiss.

‘You look lovely honey. But you better hurry up and play with your new toy, I need to leave soon. I will supervise you and tell you what to do and then you can try different things all weekend. First go over and kneel in front of the toy facing it.’

‘Good, now untie the ribbon from it and tie it around your little clitty.’

‘Aww that is cute. Next I want you to kiss the tip. And again. Now lick the length of the shaft.’

‘Kiss it passionately, running your tongue all over it, up and down, up and around’

‘Is that good darling?’

‘Yes Daddy!’

‘Now take it deeper and get it all wet. That is so good. In and out, in and out.’

‘Great. You are such a good girl! Take both hands and gently run them along the shaft until you get to the base. Rotate your hands to turn the toy clockwise and you will have set the vibration. Now face me and kneel so your legs are under you.’

‘Like this Daddy?’ Emma asked biting her lip as she gazed up at me.

‘Exactly like that. Now the fun bit, wiggle and lean back so the wet toy goes into your little behind. All the way, keep going darling. Yes that is it and stay there. How does that feel?’

‘I feel full but it is so good’

‘Now I would like you to bounce on it. Taking it all the way in and out. And again and again and again.’

‘It looks like you are getting excited and what nice moans. Keep at that speed now for couple of minutes.’

‘Stop! Good little girls do not touch their little clitty when playing with toys, do they Emma?’

‘No Daddy! Sorry Daddy!’

‘Not unless you want to be in chastity all weekend. Now start bouncing again and faster but no touching your clitty, just let it sway prettily.’

‘Good girl, now go faster and take it all. Faster again for a few minutes.’

‘Ok from the noises you must be really close now. Do a few slow thrusts, all the way in and all the way out. That is it. Now fast thrusts in the same way’

‘There we go and what a cute moan. You have made such a lot of cummies from your little clitty all over my carpet. I hope you enjoyed that?’

‘I really really did Daddy,’ squeaked Emma as she rolled and lay on her back on the floor looking up at me panting.

‘Well I am glad you appreciated your new toy. And you have all weekend to work out another ten ways to have fun using it and I will want to hear all about it, when I get back. I will expect honesty though and if you tell me you touched your little clitty when playing or I find you have not done all your chores or you have not completed a bit of your uni project, then you are going to be punished. A spanking over my knee, chastity time and maybe a week of being my diapered little baby girl. Is that clear honey?’

‘Yes Daddy, I will try and be a good girl!”

‘Good. Now please get up and give me a big goodbye kiss. See you on Monday darling.’

‘Bye Daddy, I love you!’