Holiday Humiliations Part 5

My final instalment of our holiday fun.....

 

Our last venue (2 days) for the holiday was an amazingly plush and luxurious inland location with some of the most amazing vistas.  Miss and i were accommodated in yet another opulent and magnificently appointed suite which quite simply lacked nothing in terms of splendour and comforts. 

 

There is a confession i have to make however and i don't know if Miss will read this blog  - sometimes She does and sometimes She does and won't tell me She has.  The confession is that i had a play, without permission....and....that i used one of the condoms over my tiny cock whilst i played.  This rebellious act took place on the first day of our stay at our final venue and happened in the middle of the afternoon.  Miss was on the enormous balcony, reading and sunning Herself.  i was in a horny sissy mood but did not think that Miss was in the mood to play.  i had already stripped off my male clothes, leaving me in just a pair of pretty pale blue full cut satin and lace panties and my tiny clit was stirring. 

 

i just had to have relief and reasoned that i would not need to disturb Miss or inconvenience Her by just having a play myself.  Using the condom seemed a great way of adding some self-humiliation to the situation.  Rolling the rubber over my tiny cock i let my mind wander to fantasies which i knew would make me squirt my sissy cum in quick time.  i imagined a scenario of utter humiliation and embarrassment.  Miss and some of Her lady friends mocking my small penis and forcing me to masturbate myself wearing a condom.  i imagined their uproarious laughter, their mocking tones....it did not take much....i pulsed and squirted into the rubber....hardly filling the tip.  If Miss does discover this transgression then it is likely i will be punished.

 

 

 

Later however, on our final day of the holiday, Miss and i did indulge in some wonderful sex.

 

Day 12  Everything packed and ready to go, Miss and i had some time to kill before leaving.  i had cheekily suggested that we could have a cock humiliation (condom) play and Miss seemed quite enthusiastic as long as She had Her personal affairs sorted out in time.  Miss left me down by the infinity pool whilst She went about packing and arranging Her belongings.  Taking a chance, i texted Her to hint that sissy was feeling horny and hot for Her.  To my delight Miss replied with messages that 'sissy would be called upon when required'.  Shortly after the text came through that 'sissy is required to pleasure me'.

 

i entered our suite to find Miss beautifully dressed in a pink silk baby doll nightie, gorgeous white lace panties and hold up stockings!  Wow - stockings.  These were a pair of the stockings Miss had made me buy for Her before our holiday.  On our enormous bed was also a condom - so it was clear that i was going to be allowed inside Miss but again the humiliation of denial of the condom would be employed.

 

Under Her orders to use my fingers and tongue, i began to pleasure Miss orally.  As a sissy it is incredibly important to get this right for Miss and to be good at it.  When my cock is as small as it is and when we both know that it hardly satisfies Her, the oral aspect is where i can make up for those deficiencies in penis length and girth.  i must have been doing ok as Miss made several compliments, calling me a 'good little sissy' but then very cuttingly making me know full well that it was a good thing i could worship pussy competently since my cock was so pathetic. 

 

Miss demanded to know if my 'sissy clit' was hard and i replied it was.  She ordered me to put a condom on and to try my hardest to pleasure Her - to try my best to use my cock like a real Man would. Miss must have been extremely turned on at this stage with Her undoubted control and dominance of the situation.  Her thoughts were probably miles away from me, rather thinking of real cocks on real Men who knew how to properly satisfy a woman.  She soon became quite verbal, describing a scenario with a lover - with me left outside on the balcony - only listening to their lovemaking.  She asked me if i would enjoy that happening.  i replied that i would but that i would enjoy the fact that She was getting the sex She desired, wanted and needed from a superior lover.  Miss came hard and i waited for Her instructions for my release - if there was to be any.

 

Miss then told me to take my tiny cock out of Her and that i had permission to cum on Her panties.  i knelt obediently between Her legs, removed the condom and focussed on the lace of Her pretty panties.  Miss continued with Her verbal humiliation of my tiny cock, mocking the amount of cum that i could produce - comparing everything to what a real Man is capable of.  As usual, i did not last long and getting my little cock as close to Her lovely panties as i could, i squirted two or three weak jets of sissy juice over the front of them.  i kept my head bowed low - hoping to hear Miss order me to clean Her panties with my tongue but She was not interested in giving me any more allowances. 

 

 

 

A few hours later we were on board our flight home.

 

A wonderful holiday with Miss - the sex was wonderful. i had secretly hoped that perhaps Miss might be able too find a lover or two and have some fun that way but we were always so busy enjoying ourselves and doing such great things together that it really made no difference.  The things we did together and the things we saw together are memories made to last forever. x