7. A Sissies Journey - An Ex Girlfriend Pays A Visit

 

One evening MS called me over to the table where She was sitting at with another couple of Ladies and Sirs. I was told to fetch drinks and then Ms told me to look up and asked me if I remembered one of the Ladies. As I looked up and it was one of my ex girlfriends, the one who had  thought I had jilted Her.

“Oh look how sweet you are in that pretty maids dress that is so suitable for you.” She laughed

“Yes Miss, thank You Miss.” I curtsied.

“And so deliciously appropriate.”

“Yes Miss, thank You Miss.”

 “And how submissive you are now mincing around serving us sissy.” She laughed

“Yes Miss, thank You Miss.”

“And she always pleases her superiors now , dont you sissy.” Ms asked.

“Yes Miss, thank You Miss.” I curtsied.

“And lots of oral & anal for you sissy.”

“Yes Miss, thank You Miss.”

“Just not how you expected sissy, and threesomes even four or five somes too.”

“Yes Miss, thank You Miss.” I curtsied.

“Are you still interested in ‘him’ now she has been effeminized and properly subjugated. Ms asked 

 

 “Oh not really she is far too pathetic now.”

“Yes Miss, thank You Miss.”

“That little cocklet of Hers always was small and quite unsatisfying but is so soft and tiny now.”

“Yes Miss, thank You Miss.” I curtsied.

“You can take her to one of the rooms for a good caning and or a pegging, for old times sake, my treat.” Ms offered.

I noticed She only offered a pegging not oral.

“Oh no but thank you so much for the offer anyway.”

She paused as if She hadn’t been thinking about this all along

 “Oh but my boyfriend might like to fuck that tight little bottom.” She said “After a spanking and fellatio with those soft glossy lips, you do remember my boyfriend don’t you sissy ?”

I looked at Him  & I did recognize Him, He was one of the jock types who used to hang around with us, always quite confident imposing, tall and muscular.

“Yes Miss, thank You Miss.” My voice even to my ears was very high and squeaky

“Do you remember when you confessed to me about your little college infatuation sissy, with the other jock?”

I was very embarrassed “Yes Miss, thank You Miss.” My voice seemingly even higher.

She giggled as I squirmed “Well my boyfriend  has heard all about that, but don’t worry it wont be gay, for Him at least sissy.” Miss and Her boyfriend both laughed and He patted my bottom.

“But you can hurry and fetch us fresh  drinks first sissy.” Ms told me

“Yes Miss, thank You Miss.” I curtsied

“How sweet.” Miss laughed

“Yes Miss, thank You Miss.” I curtsied and hurried to fetch more drinks.

Later when I was serving drinks and sticky under my dress with Her boyfriends cum, Miss told me that She was still looking for my ex infatuation.

Wouldn’t that be lovely for you sissy ?

You were the bottom in your infatuation weren’t you sissy ?

Oh not that matters really sissy does it ?

“Run along now sissy, I’m sure you have lots of housework and chores to do.”

“Yes Miss, thank You Miss.”

Some time later Ms told me, that they had found and contacted the boy, Man now, from college, but

being gay He wasn’t particularly interested in sissies or me.

One of the other Men stopped me in the hallway, it was going to be a very busy and sticky night.

Miss came to the club a couple of nights later, but Ms didn’t offer Her my ass for pegging, nor for a caning. She did however cane me in front of Miss. In fact She put me over Miss’s lap to cane me. Over Her short leather skirt so that I could feel and smell Miss getting aroused by my pitiable cries and struggling as Ms caned me. Ms was aroused too.

Afterwards Miss said it was quite enjoyable feeling my tiny chastity tube on Her lap as I was being punished. And did the Sirs feel it when I was being spanked over their knees.

I must admit I had never thought about it before now. But now She had mentioned it I wouldn’t ever be able to not be terribly self conscious about it. I curtsied and as if to emphasize my acute embarrassment smoothing my apron down in front of me hesitating on my tiny bump as I brushed over it.

“How sweet and lovely.” Miss laughed

“Yes Miss, thank You Miss.” I curtsied

The two Ladies smiled as I smoothed my apron down again.

“No wonder your Ms enjoys pegging your cute ass so much, I bet the boys do too sissy.”

“Yes Miss, thank You Miss.”

“I know I would if I liked little nancy sissies.”

“Yes Miss, thank You Miss.”

“I hope you aren’t getting excited in your chastity sissy.” Miss voice suddenly turning sterner

“No Miss,  Yes Miss, thank You Miss.”

Ms lifted my skirt and pulled my panties down. Miss made a point of exaggerating peering at my cage.

“How can you tell, its so tiny and soft.”

“Yes Miss, thank You Miss.”

“As it should always be sissy.” Ms told me

“Yes Miss, thank You Miss.”

She is a little more squirmy than usual, it is her time of the month and mine, so I’m always very horny.”

Ms said looking directly at Miss

“Oh how delish.” Miss said again not looking at me.

“And because we sync sissy is always a little more excited and emotional at this time, and the Sirs  do enjoy it too, don’t they sissy.”

“Yes Miss, thank You Miss.” I said, squirming vulnerably, knowing I would be on my knees and bent over the benches a lot tonight and for the next week nights.

“More wine sissy.” Ms said snapping my panties back into place.

“You may face the wall now sissy.” I was told after fetching two more glasses.

I felt so belittled and patronized when my superiors chatted between themselves. I deserved to be left facing the wall unobtrusive until I was wanted again. They were far more intelligent than I was and had such interesting lives. I was just a sissy maid there to serve them prettily and obediently. Sissies thoughts are not valued, and no-one is really interested in her trivial little concerns feelings. The hormones keep us far too dependent  and emotional, in a constant state of fluster and sexually charged fright. Mincing about prettily devoted to our superiors pleasure and be seen to be devotedly eager to be found pleasing.  

“Yes Miss, thank You Miss.”

Later I was caned again, while Miss went to get Herself ready, for getting excited in my chastity earlier. Then sent back to the club when Ms and Miss went on to another club for the evening. This wasn’t the first time I had noticed that Ms liked Men and Ladies as well as sissies. The Sirs do love to spank sissies after they have been caned and tonight was no exception.