Swimwear For sissies

Miss and i will be going away for a much deserved break soon.  Our venue has private bathing facilities.  Facilities where just Miss and i will be able to bathe - on our own!  This sissy has never worn a swimming costume/bikini/tankini/swimdress before so it's going to be very exciting, very humiliating and of course, very sexually thrilling for me.

Miss, however, has only given me permission to wear some girly swimwear as long as i buy Her a new swimsuit as well.  With the results of Her fitness and dietary regime so wonderfully obvious these days, Miss is no doubt looking forward to seeing how Her gorgeous sexiness looks in a swimsuit.  i know She's going to look hot and hopefully Miss will allow me to worship Her - in our swimsuits?? 

 

So last night, i bought something for Her and something for myself.  i know already that i will look like a proper sissy with probably no breast forms and my tiny clit providing an unsightly bulge whilst Miss is going to look stunning.  My sissy cuckold mind fantasising about Miss calling a lover over to our private pool and ordering me to leave whilst they enjoy themselves intimately.

 

Talking of intimate.  Last night, Miss and i made love with me predominantly in male mode - although i was wearing a pretty pale blue double chiffon baby doll and navy blue lace panties.  i was inside Her and trying my best to provide enough for Her to achieve Her own orgasm.  i failed miserably and Miss ended my efforts by telling me that i should cum as She was not going to.  i duly spurted and my tiny cock went very flaccid, very quickly. 

 

i asked Miss if She was going to have 'a cum' the following evening - forgetting that She is away overnight on business today - and Miss replied that 'maybe I will'.  She had remembered She was away - i had forgotten.  i suddenly realised.  A wonderful way for Miss to play with my mind again and who knows - She may well get Her cum this evening, and maybe not alone. x x

All The Things She Said.... She Said....

 

Miss constantly humiliates, shames and embarrasses me verbally whether i am in sissy mode or male mode.  So She should.  She is totally justified in doing so. We both know full well that my cock in male mode and clit in sissy mode is nowhere near big enough to satisfy Her sexually.  Indeed Miss pretty much has to assist Herself with clitoral stimulation when that tiny cock/clit is lucky enough to be insider Her.

 

Whilst it is delightfully arousing to a sissy to be reminded of her sexual inadequacies by Her superior, even beneath the sex games there is, between Miss and i, an understanding that Her comments, teasing and comparisons to former lovers are 100% real and 100% true.  Miss means what She says.

 

But something was said last night that might have moved the goalposts........

 

Whilst my tiny condom encased cock was inside Her, Miss casually remarked 'I think it might be time to find a lover sissy'.  How i managed not to spurt pathetically into the rubber when i heard those words is a miracle.  i let the words sink in and then told Miss that would be wonderful and that i would be so honoured to help Her make that happen.

 

Miss verbally slapped me down with Her response that i would be told if i was required and not to get above my station.  i said no more and instead used Her words for my own play in my chambers later.

 

Followers may or may not know that previously Miss and i actually did play on the scene whereby Miss and i together arranged for suitable lovers to provide Her pleasure.  Sometimes i watched and sometimes i listened.  We did it all together and loved each other more and more.  Then things changed.  Miss underwent some surgery, Her confidence fell, my pressuring increased and it became a problem for us that almost cost us our relationship.  sissy did not exist to the levels i do these days and sissy actually came about as a solution to the problems that were tearing us apart.

 

And it has worked.  Was what Miss said last night a culmination of many things?

 

1. My male mode has stopped being forceful and pushy to get back to cuckolding?

2. The bringing into our lives of me as 'sissy' has allowed the fantasy, the hope of a return to playing to be more likely?

3. Miss is feeling amazingly sexy about Herself? (i would if i was Her!!)

4. Miss feels our relationship has become as strong as it was when we played?

 

There might be other emotional factors too?

 

So how about the physical?

 

1. Miss is getting a bit bored of my tiny clit?  It's not satisfying Her?  Well that's a given as far as size goes!

2. The condom last night - did it remind Miss of Her fun in the past?  i asked Her this whilst inside Her and She did say it did.

3. She's getting attention?  Is there someone already subtly signalling to Miss that they find Her attractive? More than one person perhaps?  Has Miss noticed?

4. Is there someone Miss has seen at work or somewhere else to whom She is physically attracted?

 

Whatever it is i am not going to push it, either in male mode or as sissy.  Miss has always had and always will have the control when it comes to involving a third party for fun.  She might just want some one night stand arrangements - just as we used to do.  She might want something more - a trusted lover who could play our game by our rules?  Whatever Miss wants it will be at Her pace and my involvement will be at Her discretion.  She knows i will have many ideas and scenarios but they are to stay canned unless asked for by Her.

 

 

 

Of all the things She said.....x

 

 

 

 

Condomination

Early yesterday evening Miss sent me this text:

 

'sissy, I expect you to be dressed in suitable nightwear when I get home later.  The pink gown that is on the bedside table in my chambers should suffice, with suitable lace lingerie. There is also something there I may let you use later, though your smallness may not allow it'.

 

That 'something' was a condom.  The wetness in my panties from the text alone was nothing compared to the wetness in them when I actually saw the condom.  There, on top of my nightgown.  Miss was actually going to let me inside Her!  i dressed as instructed.  The pink Olga 3/4 length gown over a white lace bra, white suspender belt, smoky grey stockings and a pair of my special sissy panties with 'sissy clit' embroidered on the front in pink.

 

 

 

But maybe the condom was not for me? Maybe Miss was bringing someone home with Her?  I asked the question - by text, and received this reply:

 

'(no one is coming home with me)....but I thought I might let you try and make me cum with your little clit and as I have said (in the past) you couldn't have sex with me perhaps you could wear it and then you are pleasuring me, rather than yourself'.

 

A wonderful reply from Miss and that is exactly how it turned out to be.  With Miss dressed in a gorgeous blue camisole with pretty blue lace panties and looking in such magnificent condition with the results of Her workouts, runs and eating plan so clear to see in Her sexy shape, my clit could do nothing but be hard for Her. Pathetically small - but hard. Hard enough it remained as She made me put on the condom.  I was going to be allowed inside Miss!

 

She clearly just wanted to feel some sort of hardness, to use it for Herself, to not allow me to actually be in Her like a real man would be but to have the condom do it's job by humiliating me, reminding me of my place and empowering Her - all at the same time.

 

Miss beckoned me to get on top of Her, telling me to use my tiny clit whilst She thought of well endowed lovers.  She told me in no uncertain terms that She would be thinking of the Men She had enjoyed in the past, remembering how they pleasured Her and how much bigger and better than me they were.  i knew i could not cum unless being given permission. i knew that this was Her pleasure and not mine.  Maybe i might be allowed to cum but only if She said so.....

 

 

                                              (The condom Miss made me wear)

 

She didn't say so. Miss came hard, no doubt over the thoughts of a lover. i remained hard in the condom, well....as hard as a small cocked sissy can be.  As Her waves of pleasure subsided Miss told me that i was to leave Her and go to my own chambers with permission to play.  'To remind you of your subservience to me sissy', were the words She used.

 

But there was something else Miss said, whilst i was insider Her,  Something quite profound and wonderful.  It was over those words which i played with myself in my own chambers and came hard, after only three or four pumps of my tiny cock, squirting my weak, pathetic sissy squirts over my lace suspender belt (Miss had made me take my sissy panties off earlier). 

 

My next post will 'muse' over that but for now, thank you Miss for the shame, the humiliation, the re-affirmation of your superiority, for allowing me inside you and for allowing me to play. x

You Can't Stay But You Can Play.

The default sleeping status for me as sissy is in my own chambers, with Miss in Hers.  Sometimes i will, in the hope that i may join Her, ask where i am sleeping for the evening.  i tried that tactic last night and it failed miserably with a swift rebuke from Miss that 'you will be sleeping in your own chambers sissy'.

 

i think from now on that's what i should assume  - unless Miss says otherwise.  One thing that is certain however is that wherever i sleep, i absolutely must not play with my sissy clit UNLESS Miss gives permission.  Last night then, whilst i was denied Her company, Miss did give me permission to play.

 

i retired to my chambers still wearing the 'control panties' Miss made me change into earlier in the day, white lace bra, white suspender belt and natural stockings.  Along with a pretty blush pink chiffon capped sleeve semi sheer baby doll nightie i felt very girly and femme.  Even though the panties Miss gave me to wear were not elaborately sissy or girly, they used to be Hers and that in itself was exciting.

 

The rules of being allowed to play are that i must describe for Miss in my blog what i was thinking about during my play with my tiny cock.  With it being Valentines day today i imagined Miss having laid out some of Her sexy black lace lingerie on Her bed and telling me to dress Her for 'our date'.  'Our date'?  i questioned - thinking we were going out together.  Miss replied 'yes, our date.  Your date is at home, my date is with my lover, we met last week, did I not tell you?  Now be a good little sissy and get me ready for Him.  I'll text you later to let you know what I have been up to and maybe a picture or two so that you can see what a real cock looks like'.

 

 

 

That's as far as i got as i spurted pathetically all over my panties.  x

Unsightly Bulges

i've been in sissy mode all day today and will remain so for the whole day and evening. Miss has had me do some domestic chores in Her chambers.  A full dust, hoover and bed sheet change.  i've been wearing a very tight just below the knee length red/white/grey check pattern wiggle skirt and a snowy white polo neck jumper.  Underneath that i had been wearing a matching set of pretty white lace panties and bra along with a six strap white suspender belt and natural stockings.  It's been a sissy delightful to be doing the chambers for Miss today. Feeling my tight skirt brushing against my stockings and...as an added bonus...my silicone breasts are being worn!

 

i say 'had been wearing' because Miss demanded a lingerie inspection when She got home from work and was less than satisfied that my tiny sissy bulge in my panties was spoiling the lines on my skirt.  Even though She added that it was so small a bulge it still did not look particularly feminine.  So Miss ordered that i step out of my panties and She rummaged deep into Her own lingerie drawers to produce what She called Her 'big panties'.  Miss has not worn these for ages for Herself as She has lost so much weight, their tummy flattening qualities are no longer needed. 

 

i changed as ordered, standing directly in front of Miss with my pathetically tiny cock dangling whilst Miss pulled up the pair She had selected.  Naturally i started to harden and blushed, explaining weakly that with Miss standing there in Her pretty blue lingerie my clit would always try and harden.  Just minutes before i had been helping Miss with a new dress She had bought. Miss looked gorgeous in it and as i zipped, clipped and then unzipped and unclipped it for Her at the back i imagined a lover doing just the same for Her prior to a passionate love making session.

 

My tiny bulge does look a little better in these. Bearing in mind it is in a state of excitement and almost fully erect. The loose suspender strap is very slack of me!

 

 

 

i'm now wearing the 'control panties' but my clit is still wet.  Miss has demanded that i get a slip for this skirt to stop it riding up.  She also remarked that i will be buying Her a pair of shoes- online -very soon.  i can't wait.  i also can't wait for a real life shopping trip with Miss and all the opportunities for humiliation and embarrassment that might go with it. x

Afternoon Delights.

Miss was on top form Sunday morning and had me carry out several domestic chores whilst still wearing my sissy lingerie.  i was soaking my panties with arousal with every command She made and was quite clearly making too much of a sticky mess in them as Miss noticed this and demanded that i change. 

 

Miss had already been out for a run and i was very hopeful that She might require some special sissy soothing from me later in the day.  i was somewhat cheeky when serving Miss her post run breakfast when i asked Her if there was anything else that might like to be eaten today.  i think Miss kept that though to Herself as one i had changed into some clean and fresh lingerie She told me that She was going to make use of me in my own chambers.  i was wearing this delightful set:

 

 

Red is not usually a sissy colour but i just love the panties.  Full vintage pin up style with a pretty bow. Naturally the bra had to be worn to match.  My tiny clit was already wetting my panties as i followed Miss to my chambers. 

 

She demanded a massage with oil and i willingly and dutifully applied my best techniques over Her hot body both front and back.  Miss was wearing a gorgeous pair of navy blue lace and silk panties with a luscious lace panel trimmed in black at the front.  After almost 20 minutes of massaging Miss demanded that i touch Her in more intimate parts and i gently began to tease the petals to Her damp sex.

 

Miss clearly wanted something more substantial and told me to get Her glass dildo from Her chambers and use that on Her instead.  As i retrieved it i noticed an un-opened packet of condoms in the drawer and instantly became even harder in my panties.  i tried to raise the subject of the condoms but Miss told me to concentrate on Her.  i found that very hard to do, having just seen condoms and naturally all sorts of cuckolding thoughts were in my head. 

 

Miss though was becoming more and more aroused with the glass dildo sliding effortlessly in and out of Her wetness.  i had a front row view as i pushed and pulled it back and forth, the sounds of Her wet sex driving me mad with lust for Her.  Despite my best efforts and Miss telling me in no uncertain terms what She was thinking of (an endowed lover with sexual prowess way beyond mine) i can't have been doing too well as Miss took the toy from me and turned it round so that the fatter end went in first.  From there She took over and i watched in awe as She described Her lover and his big cock satisfying Her.  She came loud and hard, moaning with pleasure. 

 

Miss must have felt like rewarding me. She told me to come and lie next to Her.  Explaining how my little clit would not be going inside Her as She would hardly feel it, She told me to play with myself and cum for Her.  Such an honour!  Miss knew my pathetic staying power would result in a sissy squirt very soon and no doubt She wanted it all over and done with quickly.  Miss proceeded to comment on my tiny cock, laughing at it's smallness and uselessness, She demanded that i try to cum like a real man, to show Her if i could cum like a real man would. 

 

Well..... of course i could cum, but nowhere near like a real man. i simpered and whimpered like a proper sissy, my tiny cock pulsing and twitching in my hand.  Miss was relentless in Her humiliation and within minutes i had squirted and spurted.  To me it felt like a massive jet and several other jets but once the ecstasy had subsided Miss told me quite categorically that i had just cum a pathetic amount and had only managed to reach the top of my panties.  The shame was complete.  What else should i have expected with such a small cock? It's hardly going to produce 'man sized' quantities of cum!  Hoping to impress Miss i scooped up a small dribble of my squirts and tasted before swallowing.  Miss just laughed. 

 

Thank you Miss for allowing me that pleasure.  Thank you for allowing me to pleasure you.  It truly was an 'afternoon delight'. 

 

Now.... about those condoms....?? Miss said later that they were out of date. Do they need replacing?? x

 

Busy...Busy....Busy....

 

 

If you follow my blog you will have noticed a significant drop off in posts recently.  There are times when 'real life' just gets in the way of all things 'sissy' and i'm sure you know that these things can happen.  Miss too has had a hectic week. She continues vigorously with Her fitness and healthy eating regime, which, combined with Her heavy workload, means that there are and will be times when our sissy/Miss relationship goes on the backburner.

 

But yesterday evening and today we are back with a bang!  Firstly last night at Scrabble and Miss took quite a thrashing from sissy (in points!!).  i think Miss helped me considerably however with two things.  The first being that She somehow forgot to distract me with any verbal teasing, mockery or humiliation - a tactic that has proved successful in the past.  Secondly She made a quite generous gesture in showing me where i could place a tile which lead to a seven tile placement of mine across a triple word score and a whopping 85 points.  There really was no way back for Her from there in terms of winning the game and sadly for Miss a hat-trick of wins did not happen.

 

i was secretly hoping that Miss would allow me to pleasure Her after the game but instead She ordered a cup of tea to be delivered to Her chambers and that i was to bring one to Her in the morning at 7.45.  It was quite clear that Miss was not up for playing and that i would be sleeping in my own chambers  - with no permission given to have a play of my own.  Frustrating as it was to be dolled up in a pair of my gorgeous 'sissy panties' with 'prissy sissy' embroidered across the front and a pretty baby blue cap sleeved chiffon baby doll nightie, Miss had not given permission. 

 

The following afternoon however, things between us got seriously hot and sexy and i'll write that up in my next post later today.  One of my hardest and most powerful cums as a sissy - though Miss made sure to bring me right back down to earth with Her observations....... x

 

 

Pleasure Me......And Leave.

Miss and i had a really good weekend.  Lots of fresh air and exercise. We both enjoy the outdoors - it's so invigorating.  Miss has also had two cums this weekend, one given to Her from me in male mode on Saturday morning and one last night, given to Her from me in sissy mode.

 

In male mode it was penetrative sex and i was wearing a pretty yellow lace bra with a pair of my special cuckold embroidered panties, also in yellow.  Already an oxymoron as how could i possibly be in male mode dressed like that? i suppose it's that blurred lines area between sissy and male - Miss sometimes calls it 'sissy boy'.  It was wonderful love making with me on top of Miss, trying to make sure my tiny cock stayed as hard as it could for as long as possible to be of use to Her. i must have held the tiny erection as Miss came quite hard - no doubt thinking of someone else. Naturally i would not last long and Miss made sure of that with some delicious verbal humiliation about my cock size, pathetic technique and my small amount of ejaculation. 

 

Last night however, it was 100% sissy with Miss only concerned with Her pleasure.  My face and fingers between Her legs, worshipping Her sex.  She told me in advance that once She had cum that i would be sent to my own chambers with permission to play.   She also told me that whilst i was using my lips, tongue and fingers that She would be thinking of a lover in order to enhance Her cum.  Whilst doing my duty i secretly hoped that Miss might let me stay and cum in Her presence but She was having none of that and within minutes of Her release i found myself alone in my chambers whilst Miss glowed in Hers. i left with a proper curtsey and a bulge in my wet panties.

 

 

 

i fantasised about Miss with a real man in Her chambers, pillow talking after a wonderful love making session with Him. Occasional laughter, talking about my inadequacies, the sound of kisses, sheets being moved, soft moans from Miss and then more passionate love making.  i came hard over my cotton floral panties. 

 

Yes, a great weekend with Miss both emotionally and physically.  x

Left High......But Not So Dry...

When Miss came home from work yesterday i was dressed in lingerie for Her.  i wanted to look my most girlish and sissy with an emphasis on frills, froth and all the other sissy trimmings.  i chose a white strappy translucent lace gown with a gorgeous split at the front.  Under that and quite clearly showing through, a pretty pale pink lace bra, six strap pink and white suspender belt and natural stockings. i had also chosen a pair of my special sissy cuckold panties.  These ones were high waisted full cut satin, in pink, with delicious ruffles on the back and the words 'sissy cuckold' embroidered on the front.  i own four pairs of these 'special' sissy panties in all the correct girly colours and wear them either when Miss demands it or i am feeling more sissy than usual.

 

i had been hoping all day that Miss would require me to pleasure Her that evening and that perhaps She might also allow me to cum in Her presence, maybe inside Her or in a condom or make me cum whilst humiliating me.  None of the above happened. Whilst it was an honour to be allowed to sleep with Miss in Her chambers, She was not in the mood for any play.

 

So this morning, before Miss went to work, She told me what my household chores would be and then gave me permission to play whilst She was out.  i never pass on that sort of opportunity and have now cum hard into my sissy panties.  As the rules from Miss state, i have to let Her know through the blog what i was thinking of whilst i played.

 

My thoughts were of Miss, texting me a few hours after leaving this morning.  She texted me to tell me She would be late home today because 'an opportunity' had arisen.  We both know exactly what the term 'opportunity' means.  Miss texted me again to say that i was not to text or call again until She texted me to say She was on Her way back.  Miss sent one last text describing how She would have a special present for me in Her panties. 

 

Every sissy should know EXACTLY what that means......

 

These are the panties i wore when i spurted my sissy squirts.  i hope Miss is pleased.  x