Buy Me Stockings sissy!

 

 

Miss and i are soon going on holiday.  On paper it looks to be a totally exotic and indulgent time of opulence, extravagance and luxury.  Let's hope that the reality is the same. 

 

i'll be in male mode for most of the time away but there will be times when i'm allowed to be fully sissy.  We have not agreed those occasions yet but have agreed that it will likely be three occasions.  i will be packing accordingly - for both me in male mode and me as my true sissy.  Even in male mode i will make sure that i have enough lingerie, stockings and prissy nightgowns to keep me feeling femme.

 

Just this lunchtime, Miss was busy on Her tablet whilst i was looking at some sport on TV when She suddenly got up and came over to me:

 

' Is sissy available right now'?  'Yes i'm sure she can be' - my reply.

' Good.  Then buy me these stockings and have them sent express delivery'.

'Yes Miss'.

 

She handed me the tablet and on there were two pairs of hold ups.  I noted the details and within 5 minutes had ordered them, paid for them and ensured express delivery.

 

The stockings looked luscious.  It's pleasing to know that Miss is going to include stockings for Herself on our holiday.  Pleasing for me in both modes.  She knows they turn me and sissy on and She knows that both of us love the thought of Her wearing them for a real Man.  i asked Miss if She was also taking a suspender belt on our holiday.  She will be - it's getting even better!

 

What if Miss makes an 'acquaintance', dresses for him and then texts me to let me know?

 

 

 

A short while later Miss commented that She would probably not be 'pulling' when She is away for the early part of next week on business.  To our American friends and other non-Brit readers, 'pulling' means picking up, hitting off, trapping.  She explained that was because all of Her sexy lingerie was going to be packed for the holiday. i remarked that if anyone chatted Her up during the business days away they would not be doing so just because of Her lingerie as they would not see it to start with. Miss agreed and said 'well I won't be revealing sexy lingerie to them then'.

 

My panties got quite moist when i heard Her talking about pulling!  It just came straight out of the blue.  i wonder what triggered that?  Is there a possibility?  Has She got someone in mind and is just waiting for the right moment - and to be dressed the right way for Him?  Hmmmmmmm.

 

So i'm in sissy mode right now with male clothing on top.  Unless Miss says otherwise i shall remain in that mode.  The reminder right now is the fact that i'm wearing  a gorgeously pretty yellow lace bra and matching panties.  Maybe tonight, sissy will be required to pleasure Miss?  i hope so! x

p.s i suggested that Miss might like/need some condoms for our holiday. 'Get them sissy' She said. x     

He Definitely Noticed

In an ideal world, i'd be dressed as a sissy all of the time.  Outwear and underwear.  The real world however dictates that there are occasions where it's 'male mode' on the outside and sissy lingerie underneath.  i do this quite often. It's a reminder of the sissy within the male - a 50/50 compromise for when it is not possible to be fully 'sissied'.

 

Yesterday we had made an appointment for a conservatory door fix at our house.  They weren't closing correctly, especially on hotter days when the doors were expanding slightly. i was dressed predominantly in male mode - merino jumper, jeans, socks. Underneath however i had on a pretty salmon coloured bra and panties set and must have been so comfortable in it that i totally forgot that the repair man was coming round.  It was too late once the doorbell rang.

 

Too late for what?  To remove the bra!  Why remove the bra?  Well, the bra lines, straps and cups were quite evident under the jumper.  But aren't you a sissy?  Yes i am. Then you keep it on then sissy and suffer the humiliation and embarrassment.  Yes - that's right.  It's what sissies enjoy isn't it?

 

 

 

The above paragraph was my Gollum thinking - all carried out in a nano second.  Now however, the door was open and the repair man was there - definitely too late!  i was very conscious of my bra now. i felt it almost burning on me. i daren't look down to see if anything was noticeable even though i knew it was.  The cups, the straps, the back band.  He saw it, i'm sure He saw it.

 

i tried to remain calm but there was definitely a very brief acknowledging smirk from Him. A herculean effort from me not to blush.  He only stayed ten minutes,, easily repairing the door. 

 

My tiny sissy clit was wetting my panties with the arousal of the embarrassment.  No physical attraction to the Man at all - just the situation making me wet - a classic sissy situation.  No hardness in my clit, just wetness.  Delightful.  Wonderful. 

 

If He'd been better looking??  If He'd been better looking and said something??  If He'd been better looking, said something and expected something??  Would i have???

 

 

 

Hmmmmm..........x

Even Better Than You sissy.

 

 

Since just about every sissy is considered to be utterly hopeless at satisfying a Woman with the excuse they have for a cock it is widely accepted that the best weapon a sissy has to pleasure a Woman is their tongue and lips.  Furthermore, many sissies consider themselves 'experts' at pleasuring a pussy orally.  Some go as far as believing that they are even better at it than real Men.

 

The mistake here is that it does not follow that just because your cock is tiny and fails to satisfy that your oral skills aren't going to be equally as rubbish - in comparison to a real Man?

 

Imagine as a sissy being told at some point that even this aspect of your efforts to pleasure Her are well below the standard of a lover or lovers?  Imagine being told as a sissy that 'you are ok sissy but He's much better'. Where would you, as a sissy, be then?

 

 

 

Utterly humiliated. x

 

 

Shopping For Miss

 

 

Well..... it finally happened!  Miss and I had a great day on Saturday even if we did not find absolutely everything Miss expected me to buy for Her.

 

Despite having to wear male clothes for this very public venture i was wearing a pretty beige bra and panties set underneath with both pieces delicately adorned with pale blue bows.  i wanted hints of bra lines to show under my male top and once Miss approved of the lingerie was pleased to see that there were indeed subtle lines noticeable.  It is quite important to a sissy that there is always the chance of people noticing things like bra lines when out in public.  The potential for embarrassment....for humiliation....so very arousing.  Miss was looking very classy in tight black jeans, suede boots and a gorgeous semi sheer white blouse.  For effect, She deliberately wore a very lacy pink bra underneath Her blouse without a cami top so Her bra lace was very noticeable.

 

'Not for your benefit sissy' She told me.  i like Miss to dress suggestively so that She will be noticed by real Men. i'd like Her to do it much more often.  She looks so hot going to work in Her dresses and heels.  Men must surely be noticing Her?  It was good of Miss to allow so much of Her bra lace to be seen for this shopping trip and i did catch a few Men looking straight at Her gorgeous breasts whilst we were out and about.  Real Men usually will look without worrying about being subtle because usually they have proper sized cocks to back up the looking!

 

This was a new experience for both Miss and i so not everything went according to plan.  Sometimes Miss forgot to call me 'sissy', instead using my real name.  i guess that will come with practice and confidence?  i assured Her that i would not be in the slightest worried about what anyone else thinks.  That's the whole point isn't it? If they hear it then great, let their minds come to conclusions and if they don't hear it then great also.  She did get it spot on several times though with the best example being 'put that in the bag sissy' - the sales lady heard it most definitely and i blushed girlishly. 

 

Miss made sure that i carried items around shops that She wanted to try on and of course made sure that i paid for the things that She had decided the day before that i would be paying for.  i tried my best to provide good suggestions and opinions on dresses, skirts and tops - those that looked good and those that were not worthy of being on Her body.  It was very pleasing to have Miss make me buy a quite expensive dress that i picked out for Her. 

 

The idea of lunchtime cocktails and having Miss quite brazenly look at and maybe flirt with other Men constantly kept me excited in my panties and my little clit was going from hard to soft and back again as we went in to shop after shop.  Naturally my panties were considerably soaked with sissy juices and a patch had definitely begun to form on my jeans. 

 

With it being a Saturday it was pretty busy and perhaps this, coupled with the changeable weather meant Miss could not work any opportunities to embarrass me or humiliate me with real Men so it was a shame that aspect did not happen.  Also disappointing was that we could not find any lingerie that Miss wanted me to buy for Her.  It was lingerie that would have provided Miss with the best chance of shaming me, embarrassing me and humiliating me but without the right items it just could not play out.  (Miss did make up for that somewhat by making me buy Her some new lingerie online once we got home).

 

Overall though the shopping experience was wonderful.  Miss mostly got what She wanted to get and i really enjoyed having to pay for the things She wanted me to buy for Her.  i think Miss knows that we can make this experience even more exciting for us both when we do it again and maybe She will ask my views when in sissy mode or ask me in male mode what sissy might like to happen before we do it again?  One idea we did agree on was that sissy should have Her own shopping trip where Miss really could go to town on embarrassment and humiliation.  Naturally the shopping trip would include purchases for Miss but be mostly for sissy to be exploited.

 

We went out for dinner later that evening - paid for by me.  Miss looked ravishing in a dark blue top and tight jeans.  Under that She wore Her sexy black and blue lace bra and pantie set - a set neither sissy or me in male mode has been allowed to enjoy Her in.  Well.....sissy bought it for Miss to feel sexy in for others so there's the answer! i wore a new set of male clothes on the outer and underneath a delightfully girly pink camisole top and matching French knickers.  Both prettily trimmed in cream lace.  This set was hardly noticeable on through the male outerwear but felt wonderful to wear. 

 

We were close to home for this meal so Miss, perhaps wisely, chose to keep the sissy reference to a minimum and chose, again perhaps wisely, not to be flirtatious with any real Men.  Maybe that's something we could do away from home? We also had the son of a friend waiting our table so it was especially difficult to play the game.  Despite that we had a good time and i think Miss knew that i was feeling very horny in a sissy way when we got home. 

 

On our sofa, with me in just my pretty lingerie and Miss in Her dressing gown with that hot sexy set beneath, Miss ordered me to take my tiny sissy clit out and play with it for Her amusement.  Miss was not interested in any physical contact in the slightest, totally refusing my hopeless requests to 'do anything for you Miss'.  She just did not want pleasuring at all.  Possibly wishing that a real Man was at hand? i was not allowed to touch Her except to hold and kiss Her hand.  The verbal humiliation began in earnest.  Belittling my pathetic cock......talk of what a real Man could have done for Her tonight.....going out for dinner with real Men.....forcing me to watch......forcing me to listen......encouraging me to squirt my sissy juice over my panties. 

 

 

She knew i would not last long.  Moaning and whimpering, my free hand clutching at Hers and then caressing the lace at my breasts of the camisole....imagining.....hearing Her and then limply pulsing my cum over my panties. 

 

Miss then retired to Her own chambers, telling me to spend the night alone in mine.  Maybe Miss had a play on Her own?  If She did there's no way She would have been thinking of me!

 

Hopefully we can do a shopping trip again soon and perhaps we can discuss beforehand some things that we could make happen during it? I am so lucky to have Her. x   

Sissy Shopping Humiliation

 

 

Around Christmas time last year, Miss had arranged  day where sissy was to take Her shopping.  Unfortunately that day never happened due to a flu bug that made Miss quite ill over the holiday period.  That trip is now back on - tomorrow!

 

Yesterday afternoon Miss was feeling especially horny and demanded that i get my tiny cock hard enough for Her to use.  To assist me in keeping it hard She deliberately changed Her panties to a hot sexy black lace pair with a sheer back.  The sort of panties a hot sexy Woman would wear for a real Man - and it was that thought that i kept in order to help my small cock stay hard for Her.

 

We lay on our bed, side by side. Miss in Her sexy panties and me in a pretty pair of pink cotton panties.  We were both stroking each other.  My fingers pressing gently on Her clit through Her panties and Miss lightly touching my tiny cock.  Miss then began referring to 'sissy' in the third person.  'What would sissy like to happen when we go shopping tomorrow'?  i replied, on behalf of sissy, that 'she' would love to be publicly embarrassed, humiliated and teased. Miss knew that would be the type of answer and went on to say 'she'd enjoy buying me lingerie that would be for someone else, a boyfriend, a lover'.  Oh yes!!  And not just lingerie.  Dresses, skirts, shoes. 

 

Miss was definitely getting aroused at the thought of this power and knowing that the more She might humiliate Her sissy whilst shopping then the more would be spent on Her by sissy.  A very simple but highly effective formula!  Then Miss added something which made my tiny cock as hard as it could ever be.  'I might make sissy take me to a cocktail bar around lunchtime.  Make her pay for everything whilst I look at the talent, at all of the real Men there. I could get sissy to buy a Man a drink - someone I like the look of.  Perhaps get her to tell Him I like the look of Him. Tell Him you are a sissy and I need a real Man?'  Miss then ordered me to put my little cock inside Her.

 

 

 

Somehow i managed not to cum but Miss was loving it and all of these thoughts must have been working for Her as She climaxed hard on my small cock - no doubt aided considerably by what She had said and just how much fun She could have embarrassing and humiliating sissy.

 

With my still hard cock insider Her Miss knew that She could make me cum easily and then proceeded to describe how sissy could then take Her out for dinner after shopping and pay for it whilst Miss once again flirted with real Men.  That was all too much for me, causing my puny little cock to pulse and dribble into Miss. 

 

Miss is clearly going to enjoy Herself tomorrow with sissy on their shopping trip.  i can't wait for it.  So very excited.

 

Let's see what happens. x