Sunday, December 30, 2012

onto the bit you are waiting for part 1

I have written this in a bit of a note format, and to be honest i can't be bothered with fleshing it all out.  i assume you get the picture...

my heart skipped a beat when he knocked at the door.  i walked over, smiled sexily and opened the door to let him in.  he looked me up and down, walked past me and then said, "hi, you look very nice, well, this is me i hope i don't look too bad"

he looked like a smaller version of Bobby Davro, slightly plumpish, unshaven and smelling of smoke despite his profile saying he didn't smoke.  he was about 5 ft 6 inches tall, which meant that (since i am about 5'7" to start with, then i was wearing 5 1/2 heels) i towered above him!  all in all not someone i would fancy.

he held his arms out with a "so what do you think" pose.  i thought what the hell, i am here, dressed and raring to go, i might as well.  so i smiled and said OK, and took a step towards him and started to kiss him.  He instantly put his arms all around me and then his mouth was all over mine.  i think he must have a really big mouth, because he just smothered me.  I could taste the smoke on his tongue as we embraced.

he had his arms around my back/waist and i had my arms around his back and it seemed to feel a little awkward until i realised that girls tend to put their arms around a mans neck.  once i had adjusted this it felt better and he pulled me even closer.

you can tell how interested i was as i remember listening to jo whiley..

his hands were soon on my ass, pulling up my dress, me pulling it down a couple of times, until i decided not to bother and let him feel away.  we were close together. not really dancing, but did have a bit of a sway.

he roughly grabbing my boobs, which was a bit of a shock, especially how hard he was feeling them.

i dropped my hand to feel his cock, stroking it through his trousers.

bit more kissing

then i unzipped his trousers, more rubbing of his cock

by now dress was around my waist, panties and suspenders / stockings on show

i was having trouble undoing his trousers, so he undid them and let them fall to the floor

feeling him up in his boxer shorts i could feel his penis, and it felt hard, but there didn't seem much of it.

he stripped off his jumper and t-shirt while i tied my hair into a ponytail to keep it out of the way.

he then walked up behind me and grabbed me, so i started grinding my panties against his boxer shorts after a bit i was turned back around for more kissing

feeling into his boxer shorts, grabbing hold of his cock and wanking him

lots more kissing, often quite rough from him - he was definitely not a good kisser.

I could feel the damp stickyness of precum on his penis on my hand

was expecting his cock to grow and grow, but that was it.  how small could it be i thought?

i could feel he wanted my dress off so i did. i took off my dress and managed to keep wig on

 i kicked off my shoes to make us more level

This is what i looked like (except with some make-up on!)

he paid me a few compliments on how good i looked etc

kissing my neck turning me on a bit and making me shiver which was nice.

i put my hands in his boxer shorts and pulled them down exposing his cock

the cut head was about the size of a small mushroom and perfectly formed, but the shaft was about as thick as my thumb and i have small hands. How long was it? i hear you ask- as it had a pronounced upwards curve i would be very generous 4 1/2 inches. and yes that is generous.

"Is that it" i thought as i kissed and wanked him off a bit, hoping it would fill with blood and grow.
more kissing and a bit of wanking and i gently felt his hands on my shoulders, i took this to mean that he wanted me on my knees.

i kissed his neck, then slowly traced my tongue and kissing down his body towards his groin, until i was on my knees facing his cock.  this was the first time i had come face to face with a cock, and it seemed even smaller when i was next to it.

i gave it a few more squeezes with my hand before i put my lips against the head and gave it a lick.  i could taste the pre-cum mixed with a bit of urine, but after a few licks the taste disappeared.  i licked up and down the shaft (which didn't take long), over the head and again on the shaft.  a few kisses on the side before i took the head into my mouth and bobbed my head on it.

i was now a cock sucker.

as it was so small i could use my tongue on the head while it was in my mouth, so i did.  i took it out of my mouth, held it in my hands again and licked kissed it a bit more.  it felt like licking a lollipop, in fact i have had bigger lollipops!

i took it back in my mouth and i thought i would swallow him.  deep throating would not be the phrase to use as it only just reached the back of my mouth!  i held it for a few seconds before i felt my gag reflex about to go so i just composed myself and sucked on it.    i felt his hands on my head so i just bobbed my head in time with the rhythm. after a few seconds he took his hands off the back of my head , which was actually a bit of a disappointment as i wanted the guidance, and having his hands there helped me concentrate on the task and they just sort of felt good!

i kept up the rhythm for a few seconds, then went a bit faster

I was bobbing my head away, often taking all of him in my mouth when he said slow down I don't want to cum yet. I had only been sucking for about 20 seconds!

to be continued......

Saturday, December 29, 2012

during the day

i had booked and paid for the hotel, getting lucky as i found a discount code for £10 off.  the room cost a total of £21, which wasn't bad really.

i was excited all day for the meeting.  my nerves were causing knots in my stomach and i could hardly work with anticipation.  i was about to be a fully fledged sissy, and i wanted it badly.

The hotel was booked and paid for, the car was loaded up with all of my sissy clothes, underwear and make up that i thought i may need.

throughout the day i was checking for when my new dress had been delivered to the local store.  all day checking my phone and the tracking details on the website.  the tracking details didn't change and i had a bad feeling that i was not going to be wearing a new dress, especially as it was one that i had fallen in love with.

alas it was not meant to be.  there was no email or text message, and i even checked with the delivery point on my way to the meet.

I also thought i was not destined to get there either.  i had set off about 30 mins earlier than i had planned, but then the motorway was shut for an accident.  luckily i knew a bit of a back way and i got to the hotel at about 7.15 pm

i quickly set about getting shaved and getting dressed.

i glued my breast forms to my chest and put on my new bra and thong in lacy black/pink.

i did my make up - foundation, powder 2 shades of eye shadow, mascara and some red lipstick.

i put on  a suspender belt and stockings, making sure i could still get my thong off.  i lubed up my behind and i was going to put a medium butt plug in to help me relax, but it slid in so easy i decided against it.

my short black dress was next, followed by my wig and jewellery.

a couple of text messages to/from him and i was ready.

i knew he loved babydoll nighties, and i had bought one for the meet, so i hung it at the back of the toilet door, with a pair of hold up stockings and the matching g-string.

i was just about to put my shoes on, when i snagged my stockings (a silk pair from ann summers).  luckily i had bought a spare pair that day (as well as the hold ups) and quickly changed.

I dimmed the lights, put the condoms next to the bed and did a quick tidy up.  i was ready with about a minute to spare when there was a knock at the door.......

Friday, December 28, 2012

the email exchange 3

 monday 17th dec
you can go in first,get ready then text me your room number xxx
 That is fine i will let reception know that i am expecting you later.
What time do you think you will be able to get there? i was hoping to get there for about 7 and then get dressed etc (approx 30-40 mins)
got a guy coming round to fix my pc at 4-45. i will get there for 7-45/8-00. give you time to make yourself beautiful for me. i can only stop till 10ish. my number xxxx xxx
 That is like you - perfect!!
i hope we have time to have a dance (the girly romance bit i am looking most forward to), then plenty of time to make you happy, at least twice if possible
 darling i am not perfect, grey hair, 57 years old etc. we will have time to dance and anything else romantic you would like. laying together and just kissing and cuddling xxx
you are perfect to me, that i s why i agreed to marry you.
you treat me like a lady until we get into bed - then treat me like a whore. what more does a girl want?
 I keep reading this over and over. having a slow dance with you, sneaking a kiss here and there, you touching my bottom, me leaning on your shoulder before we undress each other and climb into bed for lots of kissing and cuddling sounds perfect to me.
i do have one other request if posible (please feel free to say no) - would it be possible for you to take a couple of pictures of me. i would like a couple of me dressed (if we can wait that long) and if possible one while i am pleasuring you with my mouth and bottom?
i am sure you know how to treat a lady...

Monday, December 24, 2012

the email exchange 2

Sunday 16th December
good morning lover. i have just read your last email from last night about the next time you cum it will be in me.
i am sooo honoured, i feel like i have won the jackpot, that was such a nice thing to say, i am fingering my pussy thinking about it.
 Hi lover
as you have not seen your wife in a while, she is desperate to ensure that you are happy.
she is starting to think about what she will be wearing for you, especially for the moment you walk in.
would you prefer she wears a sort of secretary look, with a white blouse and black skirt, and if so what would be your preference for the length of skirt?
i have one that goes to below the knees, and is posibly quite demure, or i do have a pleated mini-skirt?
if i hadn't been so excited about meeting you, that would have been the only options, however i have been looking at some dresses. i own a couple of dresses and you have seen the photos (black micro mini dress, and a silver dress). i have fallen in love with a dress online though.
it is a cocktail / evening dress that is floor length. i would describe it as a minidress, but with a see through bit fastened to the bottom. it has a long zip down the back. the "problem" with this dress is that i would definately need help getting out of it. and since it is reasonably glamorous, i think i would want to dance with you a little in it first before taking it off.
i obviously have not bought it yet, but they do next day delivery, so i may be able to have it by tuesday night, but not 100% certain.
can you please choose what you would prefer - cocktail dress, one of my other dresses or secretary look, but also make a choice of skirt length for the secretary look just in case.
would like you in the little black number or if you feel inclined to buy the evening dress that would be good too. you must wear sexy underwear too. it would be a pleasure to dance with you whatever you wear xxx loads of love your husband dave xxx
 Hi loved one.
I couldn't resist, so i went and bought the evening dress. i am such a girl that i just had to have it.
i will not get chance to try it on until tuesday night, so i will take my little black one as well in case it doesn't fit right.
i will warn you, the little black one, is VERY little, if i reach to the ceiling you will see all of my panties (i know you obviously want this, but i would rather tease you a little). i have to keep pulling the dress down to cover most of my stocking tops (it never really covers them all)
would love to dance in the evening dress though - if it fits i am sure you will like it.
ok would love to have a slow sexy dance with you and make you feel like a sexy girl xxx 
 that is exactly what i had in mind.  a slow dance, you running your hands up and down my back, the odd kiss, until you kop a feel of my arse.  i move your hand a couple of times, but enetually let you feel me up because it feels so good been in the arms of a strong man.
"kop a feel of your arse" dont want my wife swearing did you mean your womanly bottom
sorry sir, yes i did mean touching my womanly curves, although they are there for your pleasure!
i promise i will be more ladylike in the future for you.
good its not ladylike to use bad language darling xxx
i will remember, but i cannot promise to remain calm while you are consumating our marriage. xxx
you can let yourself go in our bed susan xxx
thank you, i do hope though that you will be in charge of our love making, ensuring that you get what you want.  once i have had my little bit of romance with a slow dance, i intend to hand my body over to you.
if i am not doing anything to your satisfaction, please let me know.
got to go now susan. you will also need a sexy nightie for our date. take care now darling xxx hubby dave
i already have a sexy nightie ready for you.
and in response to an earlier question, i will be wearing a nice dress that you will need to help me out of, but underneath i will guarentee some sexy lingerie!!
if you get chance to come back on tonight - what about the travelodge at xxxx?
wifey susan
dont expect you to be totally sub. women have more freedom nowadays including in the bedroom. want you to tell me what you enjoy/dislike during our lovemaking
i like lots of kissing, and i will enjoy your hands all over my body
i will tell you what i like, but i suspect that you will be doing it!!!
travelodge xxxx sounds good xxx
nit nite sweetheart
wifey susan
nite nite babe xxxxxxxxxxxx hubby dave
 Hi loved one, if you read this in the morning i hope you have had a good nights sleep. sorry for the long message.
now for the exciting parts - i have booked the hotel (travelodge lakeside) for tuesday night.
if you cannot make it for whatever reason, please let me know before 12 on tuesday, so i can cancel without cost.
you can message me on xxxx.
i do not have access to this site while at work, but i do have access to my email - xxxxxx
it would be nice to hear from you during the day!
as for the hotel, i do not know what your intentions are?
do you want to meet me and go in together (male mode), but you will then have to wait for me to get ready.
do you want to message me and i will come and meet you at reception while dressed up? i understand any need for privacy as we are near your home.
would it be preferable if when i checked in i got 2 keys and then left one say underneath the front wheels of my car with the room number on it - you could let yourself in then and hopefully i would be sat waiting for you.
or something else?
very excited now

Sunday, December 23, 2012

the email exchange 1

So on with the story...
this is a copy of the emails we sent each other prior to meeting.  I am the pink one if you hadn't guessed.....

i was hoping to set a really flirty and sexy mood for when we met.

15th December 2012
hows my number 1 wife
missing my husband terribly
missing my bedmate too
since we last spoke, i have changed my hairstyle. i hope it does not put you off me. i want you ON me, not off me
xxxx (sent with pic)
you look gorgeous my wife
thanks, but i knew you would say that - you kust want to get into my knickers
no its important that husbands compliment their wife. getting into their knickers is a husbands right
only after one thing though!!
 no not at all. wives call the shots as far as sex is involved. the praise was genuine
ohh thanks, you certainly know how to charm a girl - i am putty in your hands, and i would do ANYTHING you wanted....
just name it
well as my wife its your duty to please me
i could please you by turning the Tv over to sport, or by washing your clothes and cooking for you, but is that what you want?
amongst other things yes, but being a whore in our marital bed is the priority
now you are talking!!
compliment me again and you will another picture!
as well as looking a million dollars my wife needs to act as a 20 dollar whore
would you pay $20 for this? (sent with pic)
maybe $10 whore
if you treat me well, the first one will be free!
doubt it theres always a catch with you hookers
you are right, if you treat me right, the first one would be free, but the second one would cost you nothing!
make me scream and the first 100 will be free
think your pimp wont be happy
you could buy out my contract?
i will pay you back in sex
will need to sample the goods 1st before i hand over any cash
i also want to know if i will like the taste
of what my dear???
of your kiss, your sweat, your cock and your cum
i want to taste them all
and i want to taste your vagina susan
you can, and you will!!
i know our schedules seem to be preventing us from meeting, but ithink i may be able to do something on chritmas eve morning?
sorry am working. am free next tuesday and wednesday evening
i might be able to swing something next tuesday night. is that possible?
yes but will have to be hotel meet
that would be ok by me. han hotel would give us both chance to relax a little more.
true. you choose the hotel then
could you make the travelodge at ******?
bit far out i am central ******
i don;t know many hotels around ******. i will have a look and get back to you.
goig to wish you good night now.
please think of me when you get into bed!
think wife no2 wants sex am i allowed its up to you
Of course you can.a man has needs and I am not there to take care of them, so I have no problem is someone else does.
I hope she treats you well, and that you will save your best for me - you will need it !
Lovely to talk to you again, missing you loads.
thought it was bedtime
hoping you might be jealous baby
I am very jealous, but understand your needs.
You wouldn't get much sleep if I was with you.
no worries i have told her no

Thank you for that, I am glad you are faithful to me.
I need to reward you for that. New lingerie needed before we meet
yes faithful to you. lingerie pic from you???
Ok, go on then. A pic of me in some frilly knickers ready for you....(sent with pic)
they look like adult baby knickers
Maybe a bit, but they are just frilly slinky knickers with a rear hole.....
My only other lingerie pic on here you have seen before (sent with pic)
love the baby nixs
They wouldn't be on long though with you about
so true my wife very kinky
I will bring them along, but I have other lingerie in mind for you
go on wife
Stockings and thong underneath my dress.
Maybe change into a baby doll later
you tease. check for a hotel my wife
I will, but I am having too much fun teasing you.
Is your cock hard yet?
you know it is my bitch
I would have my red lips around it before you got it out of your pants
you are a slut susan
More compliments will only make me more horny for you
think you will need a wedding dress too. another pic please
My dream wedding would be followed by all yours dreams coming true later that night!
Last photo and post tonight.
Missing you. Whisper my name when you next cum....
Xx (sent with pic)
when i next cum it will be in you my darling. you are my true wife now

Thursday, December 20, 2012

Teaser Trailor

Hi everyone

In the tradition of the hollywod blockbusters, this is just a teaser trailer to the next few posts on this blog. I still have the fantasy story I was working on, but I think you may enjoy reading about what happened in my real life instead.

There were be several posts, and i will try to add some suitable pictures, so it may take a week or so to post them all.

It could be a bit long and rambly, but i hope to be able to write about it an an interesting and (possibly) amusing way.  The adventure does have a couple of little twists and turns.  I do hope that at some stage you have a smile on your face!

Anyway, as promised to give you a clue - it rhymes with "I cooked a sock."

Tuesday, December 18, 2012

sissy dictionary

sorting through some old files and i found these two listed under dicktionary!!!

they are from a previous set of training information that can be found earlier on the blog

the quality of the picture isn't great, but is readable.

Monday, December 17, 2012

i just love this image.  i have just had some hot sex with my boyfriend. so while i let him sleep a little i  just put on my bra and panties and go make myself a cup of coffee.  i know that he will want some more sex when he wakes up, so i want to be ready for him.

if only i looked like that

Sunday, December 16, 2012

new dress for christmas

As you may know i have been shopping mad lately.  since i last wrote i have bought at least 12 pairs of panties (everyday panties for work etc) and some bits of make-up.

however today, for the first time ever i was seduced by an advert on the internet.  you know when an advert appears at the side of your email or a webpage etc.  i usually ignore them, but today in a sissy state i could not resist.

The advert was for "Very", a clothes catalogue in the UK, and the piece was a long dress.  i just fell in love with it.  i checked the sizings and if the sizes are correct it should fit me like a glove (or dress!)

i thought about it for a while, before finally i could wait no more.

i think it is quite sexy, but quite demure / glamourous as well.

i have bought it with a special occasion in mind, but the news about that will have to wait....

Saturday, December 15, 2012

why am i a sissy? (part 2)

Please see part one of this to be able to follow what i am talking about!

Post wife
About 6 months after meeting the wife, i managed to get a computer and get on the internet.  this was obviously a wide passage into sissydom, and i quickly found myself masturbating while reading sissy assignments, joining sissy training sites and even following a programme that replicated a period.

me and the wife did have sex through this, but before she moved into my house i insisted that i had 2 weeks on my own.  this time ws spent with shaved legs and lots of lingerie as you can imagine.

the training websites pushed my resolve and i went out in public again in the daytime in a miniskirt and heels, and i also bought a dildo that i have sucked and used in another orifice!!

since we have been married we do not / have not had much sex.  i am not very good at it, and i don't get any practice!  when the wife was pregnant we didn't have sex until 3 months after my son was born, and to date it is at least 11 months since we had sex.  i think the wife has used her hand to "relieve my frustrations" on about 2 occasions though.

as my life as gone on, i have joined cottaging / gay cruising sites and attempted to meet men (without success), had sex with my dildo on a webcam for a man, and been to a london nightclub dressed.  i also now find myself trawling through sissy websites on a daily basis.

I have been buying myself more panties and clothes, wearing them whenever i get chance.

I am practicing my makeup skills whenever i can.

For long journeys at work i am wearing a skirt and wig etc

as i said in my first post, does the series of events that is my life indicate a sissy in the making, born to be a sissy, or an unlucky man who has become a sissy?

whichever it is, i do LOVE wearing skirts and heels!!!


Thursday, December 13, 2012

why am i a sissy? (part 1)

Why am I a sissy?

after reading the excellent guys who wish they were girls blog (  it got me thinking a little about how or why i had become a sissy.  i have looked back at my life and i now ask you if the following series of events etc sounds like someone who has just stumbled on been a sissy, or someone who was destined to be a sissy.

i have split this over two posts as there are two distinct categories - one before i met my wife and the other afterwards.  the reasons will become clear as you read.

Pre Wife (from the age 0-28)

I was a popular boy in school up to the age of 13 when i left my usual school and attended a boy only school until i passed my a-levels at over 19 years old.  (note - nothing sexual happened at school in case you was wondering)  my confidence took a beating there though.

i was dressing in female clothes (my mothers) before i had ever masturbated.

The first time i ever masturbated was when i was 17 while watching miami vice (but not dressed), and i almost didn't know what was happening and i just laid on my bed using my thumb and finger as i had seen people call each other.  the second time that i had an orgasm i was wearing some of my mothers underwear and a black skirt.

i actually own more bras than i have had female lovers

As a teenager i went out fully dressed as a girl before I slept with a girl or even touched a boob

Used a vibrator before touching a girl

Used make up regularly before been with a girl

used to wear panties, tights and a bra etc to university beneath my male clothes. (i lived at home while at University)

i am not sure about the actual timings, but i don't think i ever kissed a girl while i was in university.

Bought female clothes before been with a girl

Bought various items of female underwear before been with a girl

Visited a tv shop several times before been with a girl

Had a wig fitting before been with a girl

bought various shape garments including padded panties, waist clinchers and silicone breast forms before been with a girl

used cock shaped objects in my mouth and pussy

Bought books and magazines for tv and sissy

i did not lose my virginity until i was 25

not including the wife i have slept with 4 women, including 1 prostitute on holiday

i only ever had sex with the women once. and never saw them again for various reasons (1st was unbalanced, 2nd never wanted to see me again after my failure in bed, 3rd i was not attracted to her (beer goggles on), 4th prostitute)  my wife is the only woman i have had sex with more than once.

i think the most telling ones are that i was masturbating at a young age in womens clothes, i went out dressed a as woman before touching a woman, and the fact that none of my girlfriends had sex with me more than once.  been at an all boys school through my teens didn't help.

looking back though, i can't believe that i went out dressed in a skirt etc before i had even got close to a woman!

Wednesday, December 12, 2012

fantasy stories

as i have said many times on here, i do not have much time to indulge on my sissy side, so every little bit is precious to me.  As i don't have much time to be a sissy, i don't have much to say.

but i do think about been a sissy a lot, and i have had the sudden urge to start writing about the fantasys i have and i would live my life as a full time sissy.

i am not a great writer, and i don't know how long i will be motivated to keep writing, but i will do my best.  i can work on these stories at work, so that is a bonus and i don't feel guilty just looking at sissy pictures!

i will hopefully post my first (and only written story so far) later this week.

all of the stories will be written from a personal perspective.

maybe writing these stopries will help motivate me to get out more and improve my sissyness.