Dressed As A Girl By My G/f In Front Of My Mother

I'm very submissive sexually so do what my g/f wants. I like her to cane me in particular, but when she really wants to punish me she makes me wear a dress. It's an old school tunic which I have to wear with blouse knickers knee length white socks and red welly boots. 

I find it really humiliating. A couple of weeks ago I was standing in the corner, hands in head, dress tucked up and knickers down after a good caning when she brought my mum into the room. Mummy nearly wet herself laughing but really approved. She has always believed in a firm hand with me. She caned me until I was 18 and liked to humiliate me, as she says humiliation teaches humility and is the best way to keep boys willies on check.

They made me stay in the dress all day until Katie ordered me to change into a night dress, which I slept in. I was back in the dress the next day and was taken out in the car like it. 

Today they returned from shopping with new surprises from the charity shops - a wrap around summer dress, a girl guides uniform and a pair of blue wellies. When I refused to try them on Katie first threatened then took me upstairs to cane me. She gave me stroke after stroke until I agreed to be a good boy and dress like a girl. I had to go downstairs, apologise and say that as such a naughty boy I had to dress as a girl in the hope that I'd be a better girl. 

I tried them on in turn whilst mummy took photos. As I'd been such a bad boy I wasn't aloud back into boy clothes but was put back in a night  dress. But the final humiliation was still to come - a set of cloth nappies! I resisted and got another caning this time in front of mummy. I had lie on the floor whilst mummy showed Katie how to put it on me. I was there for an hour while she practiced. I was then put in the corner and told to stay there until I needed the toilet. Having peed Katie changed me on the coffee table. I was so humiliated my c**k shrank to nothing. I have since been sent upstairs to rest on a cot bed mummy made up. I'm not to come down unless I've done a poo in my nappy. 
I've been told that Sunday we're going for a drive and a walk, and I've to choose between the girl guides uniform with blue wellies or summer dress with red wellies. 
I'm lying here thinking which would be least worse and trying not to poo. I've a feeling a poo filled nappy comes with another caning. Three in a day is too much! My poor bottom is very red and very sore. I can't even comfort myself by fingering my c**k or bum hole as the nappy is in the way!!
Sorebt Sorebt
18-21, M
2 Responses Oct 30, 2010

I'm starting to think tha all male are submissive but some are just to shy to admit it, they love being humiliated

It is always Good when the Women take control of the men and Feminize them. We males belong in Skirts and dresses!