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Jane's mum and me pt 2

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By *andy57 OP   TV/TS 40 weeks ago

york

Right young man or should I now call you lady !!!

You best get walking about in those heels and get used to them before we go out this evening O my god the fear of hell had just struck me having heard those words out this evening talk about a novice this was the actual first time I had actually been dressed fully the fact Jude kept telling me not to worry as stated previously my own mother would not have recognised me plus I couldn't believe how feminine I looked and felt.

I was instructed to place my habd on the dressing table top where she started to shape and file my nails into a more fem shape then applied two beautiful coats of a deep maroon coloured nail varnish topped by a clear coat to finish it of matching lipstick applied and I was told to check myself out in the full length mirror on the wall.

Right you pop down stairs and practice walking about in those heels ill ve down shortly. About 30 mins past when I heard the room door open and this vision walked in looking so so sexy. Right let me see you walk I must say I was surprised at how easy and natural I found walking in the heels so just a few pointers like when you walk take smaller steps and put one foot in front of the other thiscwill give you a more fem natural hip swing each time walking back and forth xatching a glimpse of myself in the large room mirror the fact I was not to tall really helped. Right all I need to do now is just teach you to reapply your lipstick as this will rub of throughout the evening.

TBC the step outside into a whole new world xx

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By *onmacMan 40 weeks ago

glasgow

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By (user no longer on site) 40 weeks ago

This fabulous story reminds me of my encounter with an older work colleague and how she got me into dressing fully

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By *hil911Man 40 weeks ago

Solihull

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By (user no longer on site) 40 weeks ago

Ready for pt 2

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By *nardriMan 40 weeks ago

near town

The fact that this is all true is mind blowing

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By *andy57 OP   TV/TS 40 weeks ago

york

Well the time had arrived my big step out into the whole new world dressed as a woman fortunately it was the time of year where the daylight finished early.

Come on then let's go I was then furnished with a set of perls and a pair of perl clip on earrings out of the bowl onthe hall table nice it's the finishing touches that are all so import Jude stated she then fetched me a small to medium size clutch bag with a purse some money in it the most important lipstick and compact for makeup touching up through the evening,a lightweight 3/4 length black coat was slipped onto my back and Jessica was ready jess was her sisters name jude gave me as she said it was really easy for her to remember.

To this day I will never forget that first feel of early evening air surrounding the tops of my lace top stockings under my dress a d thinking shit that feels so sexy.We walked towards the car and I thought thank god were not going the bus into town,my heart pounding with both anticipation and excitement at the same time me concentrating on getting used to the heels although I say it myself I was lucky enough to master very well the fact they were not to high. Jude informed me to remember to get in the xar like a lady now your wearing a dress you don't want to be flashing your stocking tops to all, lol. I remembered watch my mum getting in and out of dad's car legs together and a wing them in remember it's the little finishing touches that make all the difference Jude stated act fem and nobody will notice. It was at this point I had to ask have you done this before at all then ? She turned and looked at me with the reply of no but it's something I have always wanted to do so it's as big a thing for me as you and remember I could get seen out with you tonight as you with me !!!

TBC XX

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By *J GeminiTV/TS 40 weeks ago

Northumberland

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By (user no longer on site) 40 weeks ago

Brilliant, carry on please.

Steph xx

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By *cubasexMan 40 weeks ago

dudley

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By *eed AttentionMan 40 weeks ago

Oxford

Very nice

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By *laric-DomMan 40 weeks ago

Chapelhall

Sounds like a fun night is about to be had

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By *iona38ddTV/TS 40 weeks ago

north east fife

Enjoying this and where will it end mmmm

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By *athytvsubTV/TS 40 weeks ago

Bulwell, Nottingham

Need to hear more of this xx

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By *oppy12Man 40 weeks ago

Swindon

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By (user no longer on site) 40 weeks ago

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By *andyel73Man 40 weeks ago

Leyland

Amazing thank you for sharing

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By *achelOTV/TS 40 weeks ago

exeter

Love where this is going, can’t wait to find out more.

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By *rgar27Man 40 weeks ago

Bognor Regis

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By *midsfabguyMan 40 weeks ago

WMids

Stunning x

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By *he Ring WraithMan 40 weeks ago

Bradford

Sexy and I bet the girlfriend finds out !

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By *eterpervisMan 40 weeks ago

back where i came from

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By *andy57 OP   TV/TS 40 weeks ago

york

It wasn't long before we were pulling into the restaurant carpark a nice Italian. At this point I asked are we really sure about this Jude as I have never done anything like this before yeah you'll be fine the fact you with a genuine woman I don't think anyone will actually notice. Mmmmm I'm thinking the opposite her looking like she did I'm think we are going to be getting a lot of attention.

Well your in for the full experience she said I remembered to get out of the car the same way I got in without flashing my stocking tops and more to the point my knickers.

As soon as we were both out of the xarvi again felt the cool evening air around the tops and the slight breeze lifting my dress up I watched jude control hers so again copy her and everything is normal again.

The darkness was broken by a husky voice spoil sports we were hoping you sexy girls were going to give us a flash. With that comment both of us ignored the men turned our backs on them and waked to the restaurant door opened by a very good looking guy who welcomed us in with a good evening ladies table for two is it,as he took our coats the fact I had at least got some small breast enhancers in I did managr to have some form of female chest to speak of.

Now I had agreed with Jude that that she would do all of the talking as no way was I going to fool any guy that I was a woman.

So the meal went without a hick up apart from the odd caressing of my leg under the table from jude !! Both finished we paid our bill collected our coats and headed of to the cinema which was on the same complex so we decided to walk the short distance the sound of my heels clipping in time with hers was a great sound and as she stated well you have mastered the shoes ??

The tickets purchased and we entered the darkness of screen 4 not a massive size so we decided to sit at the back.

The advert finished the movie started jude getting comfy next to me five or ten mins in she takes my hand and place's it up under her dress and whispers in my ear finger me now I move my hand up and feeling the warm mound between her legs I pull the satin knickers to one side and slip my middle finger into her warm pussy she gives out a gentle moan fortunately the headrest couple to us were a few seats away

TBC

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By *he Ring WraithMan 40 weeks ago

Bradford

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By *hil911Man 40 weeks ago

Solihull

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By *J GeminiTV/TS 40 weeks ago

Northumberland

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By *21funguyMan 40 weeks ago

Bicester

Pt2 wow

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By *onmacMan 40 weeks ago

glasgow

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By (user no longer on site) 40 weeks ago

Just gets better and better

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By *rgasm4u69Man 40 weeks ago

Warrington

You hopefully get pucked up by a couple of guy's

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By *lare_thomas38TV/TS 40 weeks ago

my town

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By *usie pTV/TS 40 weeks ago

taunton

mmm fantastic.

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By *ecker30Man 40 weeks ago

Northwich

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By *inkyfuntimesMan 40 weeks ago

Northampton

Loving this story

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By *enuine photographerMan 40 weeks ago

Swansea

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By *andy57 OP   TV/TS 40 weeks ago

york

I continued to finger her for sometime when she whispered in my ear let's get out of here

We are walking back to the car and she suggested we go get a drink now been I a darkened cinema but walk into a open well lit bar was a whole different thing then I felt the cool air blowing up under my dress and I thought hey what the hell we walked through the door and it was really busy go get that table ill get us a drink as I sat down I was promptly reminded that I still had a but plug in me as the seat was a hard cushion ?? uncomfortable yes but again still pleasurable as jude sat she asked if I was OK I explained and a big smile appeared on her face.

Again I copied her as she held the glass as be more and more fem the more I became fem the more I got turned on. It was at this point a handsome tall guy came over and pecked jude on the side of her face hi how's you I'm fine and you good very good.

In her next breath I was introduced to Mike who had worked with jude a few years ago as Mike leaned in a pecked me I herd him say my god she Don a great job on feminising you and his hand caressed my leg I knew he could feel my suspenders through the dress. So hey we are heading home in a mo fancy a night cap Mike!!!

I glared at jude as if to say no your mine I didn't want to share her o how I was so wrong he wasn't interested in jude but me !!!

TBC

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By *he Ring WraithMan 40 weeks ago

Bradford

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By *exbot 1Man 40 weeks ago

Chester le street

Mmmm.

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By *J GeminiTV/TS 40 weeks ago

Northumberland

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By (user no longer on site) 40 weeks ago

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By *onmacMan 40 weeks ago

glasgow

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By *andy57 OP   TV/TS 40 weeks ago

york

We arrived back at judes and sat on the sofa while jude fixed the drinks all the way back home all I could think about was WTF.

jude came into the room and announced she was popping upstairs to the loo. Mike, I think saw this as his signal and took a massive gulp of his drink and moved in close next to me. It was at this point I made my excuses and left the room for the same loo.

At the top of the stairs I met jude now out of her dress and supporting a different satin gown. W.T.F. is happening I asked. I was not expecting her reply well you have been wanting to be feminised well this Is the final part to make you complete,here and she took my hand into the bedroom un zipped my dress requested I slipped into something more comfortable and handed me the nylon lace see through gown I had seen her in previous. What you should know is apart from the shoes jude was a woman of a fuller figure so I was lucky her clothes fitted me well. As she removed the dress I asked if the butt plug could also be removed not yet sweety not yet was the reply.

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By *hil911Man 40 weeks ago

Solihull

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By (user no longer on site) 40 weeks ago

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By *urabriteMan 40 weeks ago

stafford

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By (user no longer on site) 40 weeks ago

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By *J GeminiTV/TS 40 weeks ago

Northumberland

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By (user no longer on site) 40 weeks ago

Love this story

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By *cubasexMan 40 weeks ago

dudley

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By *andy57 OP   TV/TS 40 weeks ago

york

Now I have to be honest and I felt well outside my comfort zone !!!

With that we went back down stairs Mike was still sat on the sofa but had removed his shirt and trousers.

Jude pointed for me to sit next to him and she got hold of the chair opposite and moved it round to be able to get a clear view of us both.

Now the fact I had reapplied my lipstick and the gown on I felt so so sexy and here's a guy really interested in me as a potential night of fun.

Mike's hand landed on my leg and started to caress it slowly moving it slightly higher and higher on each stroke till he reached the giggle line any woman knows the giggle line its the stocking top get past that and your laughing ??

As I felt his hand reach my panty line the fact they were strong control ones all he could do was feel the outline and the fact my cock had been tucked so well by jude he commented that I felt just like a real girl. While continuing to caress my groin area I felt his breath nearing my face (now I had up to this point never kissed a guy) his lips approached mine as I felt his lips touch mine and he started to explore my mouth with his tongue. For some strange reason I started to feel his manhood through his boxers and it felt so good not to thick but it felt long.

I glanced across at jude who was sat watching us with her hand down the front of her knickers as the wet patch I noticed was getting bigger and bigger her other hand teasing her nipples

TBC

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By *unGent66Man 40 weeks ago

Newport

Awesome story, I wish I'd been so lucky at 19!! Keep it coming

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By *J GeminiTV/TS 40 weeks ago

Northumberland

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By *rgasm4u69Man 40 weeks ago

Warrington

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By *athytvsubTV/TS 40 weeks ago

Bulwell, Nottingham

Can't wait for more xx

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By *hil911Man 40 weeks ago

Solihull

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By *ton_maleMan 40 weeks ago

Shoreham

This is so well written!

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By *andy57 OP   TV/TS 40 weeks ago

york

I was instructed to lift my bottom of the sofa with Mike removed the control girdle and removed the gaf tape holding my cock making my groin as fem as possible alowing a fem pose.

As he released the feeling of freedom was great and I immediately began to get hard, on moving down my body his lips met my cock and he started to lick the large amount of precum that had built up throughout the evening. I then felt his warm mouth take my now rock hard cock deep and I mean deep where upon jude got up and came across removing the satin gown and her panties she climbed onto the sofa and presented he pussy which was dripping wet in front of my face with the instruction to lick it slut. As I buried my face into her licking and slurping her love juice she told Mike he could remove my plug as it came out it was replaced by two of Mike's fingers which started to pump my arse in rhythm of him sucking my cock this seamed to go on for ages applying lubricant every few strokes with no sign of me unloading anytime soon. jude suggested we move to the more comfortable bedroom .

By now jude was down to her barley black stockings and suspenders Mike had removed my gown so I was more relaxed. I positioned myself between jude,s legs and start where I had left of Mike positioned me so my arse was in the air with that I felt something warm in it mikes tongue this was the first time anyone had ever rimmed me again it seamed like went on for ages then within a min I felt a cold liquid been applied and Mike's fingers starting to work on my hole again more cold liquid then I felt what I thought was a vibrator no it was his cock as more lube was applied my head was forced back down into judes pussy. Then with a gasp I felt him enter me he was so gentle but the fact I gad been prepared well with having the butt plug in for so long. A few pumps he with drew and applied more lubricant then re entering it felt so comfortable not to thick and not to long just right slowly building a rhythm and jude giving him encouragement with the word this is what she has needed all evening

TBC

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By *hil911Man 40 weeks ago

Solihull

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By *oppy12Man 40 weeks ago

Swindon

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By *he Ring WraithMan 40 weeks ago

Bradford

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By *cott60Man 40 weeks ago

Perth

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By *exbot 1Man 40 weeks ago

Chester le street

Very horny

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By *ilkyphoebeTV/TS 40 weeks ago

Biggleswade

Mmm such a horny story...more more

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By (user no longer on site) 40 weeks ago

Wow

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By *21funguyMan 40 weeks ago

Bicester

Wow

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By *eterpervisMan 40 weeks ago

back where i came from

Mmmmmm

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By *rgar27Man 40 weeks ago

Bognor Regis

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By *enuine photographerMan 40 weeks ago

Swansea

Different

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By (user no longer on site) 40 weeks ago

Loving this story

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By *usie pTV/TS 40 weeks ago

taunton

Oh heck wish I hadn't read this right now still at work I am going to have to risk it and have a wank in the office.

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By *acksmith22Man 40 weeks ago

cannock

Stunning

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By *onmacMan 40 weeks ago

glasgow

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By *andy57 OP   TV/TS 40 weeks ago

york

Mike thrusting became more vigorous and with one final thrust I felt him unload in me he seamed to pump half a gallon in me then it hit me ge was bareback and I didn't know him.

As he pulled out I felt the hot sticky cum run down the inside of my thigh. Jude moved down the bed to position herself under my cock Mike's spunk dripping of my cock onto her pussy now use it as a lubricant and give me a good fucking .Mike moved to the chair and was watching me give it to jude he then went to the bathroom came back all cleaned up and moved to judes face he was already hard again he then slipped it into her mouth she took the whole length moaning with pleasure two cocks serving her it wasn't long before I could feel the sap rising she screaming give it to me now and hard my last few thrusts and I exploded deep inside her I cum so hard and was able to keep thrusting a few seconds after me Mike unloaded his second load down judes throat.

By this time it was passed 1 am Mike said his good byes and left jude and myself lay in each others arm's and fell asleep. We both woke early and showered and cleaned it as today was the day Jane and her dad would be coming home. I never met Mike again but I was lucky enough to have a few more encounters with jude.

The other one that is also very prevalent in my mind was the time I met with jude and one of her pals Joyce,buts that's for a nother day.

I continued to dress and after Jane had decided to change sides. So I ended up marring one of her pals who knew all about my dressing and helped and encouraged it we also met as a couple visited clubs went out and about dressed together dhe fave me 20 fantastic years before she was take far to soon.

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By (user no longer on site) 40 weeks ago

Brilliant

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By *oppy12Man 40 weeks ago

Swindon

Excellent

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By *andyel73Man 40 weeks ago

Leyland

Amazing thank you for sharing

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By *cott60Man 40 weeks ago

Perth

Loved it

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By *unlovers769Couple 40 weeks ago

Beverley

Fantastic

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By (user no longer on site) 40 weeks ago

Hope to here about joyce

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By *rgasm4u69Man 40 weeks ago

Warrington

Brilliant story thanks

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By *lare_thomas38TV/TS 40 weeks ago

my town

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By *outhweel2Man 39 weeks ago

Newark

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By *exbot 1Man 39 weeks ago

Chester le street

Love it

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By *heswingerMan 39 weeks ago

the steel city sheffield

Can’t beat an older woman

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