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First time dressed and going out

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By *vman64 OP   TV/TS
over a year ago

Telford

One of my fantasies is to go out side somewhere quite dressed, what was your first experience going out dressed for the first time? Where did you go and what happened? xxx

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By *usantvTV/TS
over a year ago

Epping Forest

My first time was at quest in Leeds, was very nervous and met another CD there. who calmed me down. Then met a black guy in there and had my fist BBC and ever since then I crave black cock. I really need to get some more when this blows over

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By *uvseamsMan
over a year ago

glasgow

My first time was in car driving round and needed to get fuel , it was late at night and I waited outside a garage till it was empty then went in , while getting fuel another car came in .Went in a d paid , the sound off heels on forecourt was amazing .I had on short dress and stockings. Went in a d paid, the lady behind counter just spoke as normal not even looking at me twice , felt amazing. Still get a buzz thinking about it.

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By *irtyTrucker1Man
over a year ago

Telford

[Removed by poster at 05/05/20 16:00:07]

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By (user no longer on site)
over a year ago

Before Internet I posted a Classified ad in the local paper.

I'd dressed up in the home, but needed to take my dressing up more seriously.

I needed to force myself out of the house, in order to grow as a person, as crossdressing was at the time was consuming me.

The advert was answered and I had to retrieve the message from an 0908 number.

An arrangement was made to meet him in a train station car park.

He pulled up and I got in.. He had a Lovley car from recollection.

At that time of my early crossdressing,kissing was out of bounds.

But we both enjoyed masturbateing one another.

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By *vman64 OP   TV/TS
over a year ago

Telford


"My first time was at quest in Leeds, was very nervous and met another CD there. who calmed me down. Then met a black guy in there and had my fist BBC and ever since then I crave black cock. I really need to get some more when this blows over "

Thanks for sharing, I am really nervous about doing it

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By *vman64 OP   TV/TS
over a year ago

Telford


"My first time was in car driving round and needed to get fuel , it was late at night and I waited outside a garage till it was empty then went in , while getting fuel another car came in .Went in a d paid , the sound off heels on forecourt was amazing .I had on short dress and stockings. Went in a d paid, the lady behind counter just spoke as normal not even looking at me twice , felt amazing. Still get a buzz thinking about it. "

Thank you for sharing, that sounds amazing, I don’t think I’ve got the guts to go somewhere like a garage xx

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By *vman64 OP   TV/TS
over a year ago

Telford


"Before Internet I posted a Classified ad in the local paper.

I'd dressed up in the home, but needed to take my dressing up more seriously.

I needed to force myself out of the house, in order to grow as a person, as crossdressing was at the time was consuming me.

The advert was answered and I had to retrieve the message from an 0908 number.

An arrangement was made to meet him in a train station car park.

He pulled up and I got in.. He had a Lovley car from recollection.

At that time of my early crossdressing,kissing was out of bounds.

But we both enjoyed masturbateing one another.

"

Thanks for sharing sounds very horny

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By (user no longer on site)
over a year ago

First time was to a dressing service had heard about on the radio

Nervously went in, was dressed as maid and saw myself wigged and made up for the first time

Spent some time chatting

Nothing sexual, that came many years later

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By (user no longer on site)
over a year ago

Hun no one really cares anymore... Its all in your own mind...

The odd stare that lasts 3 seconds.

It's only clothing made of cotton, nylon or viscose.

You imprison yourself with negative thoughts and feelings.

Go out with confidence. I do and so do many others. It's 2020 not 1820

Just go out

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By (user no longer on site)
over a year ago

Cannot remember the first time but it was probably a walk at night which is one of the more stupid things to do.

You make mistakes those early times out but its all part of the learning curve.

I have some good memories of first events such as going to a club in London that was packed with trans folk and going to the first ever Sparkle event in Manchester where it felt like the entire trans population had turned out.

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By *omerset tvTV/TS
over a year ago

Weston-super-Mare

A good tv friend of mine who goes out dressed all time gave me some good advice if your going out at night and gonna be a distance away from your car or not with friends always wear flat shoes or boots cus you wont be able to run in heels if its needed ... very good advice

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By *indacxd2000TV/TS
over a year ago

Knocklyon

Amsterdam was my first proper night out walking the streets. After the first five steps your in cruise control. Go for it it’s such a buzz

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By *orkDefenderMan
over a year ago

Just East of Wakefield


"My first time was at quest in Leeds, was very nervous and met another CD there. who calmed me down. Then met a black guy in there and had my fist BBC and ever since then I crave black cock. I really need to get some more when this blows over "

I go to the 'TV Thursdays' af Quest, whenever l can get there

A most enjoyable afternoon!

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By *everlyandersonTV/TS
over a year ago

newcastle

My experience story is on my profile x

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By *vman64 OP   TV/TS
over a year ago

Telford

Sorry if I’ve given the wrong impression here, I don’t mean dress as a lady and go out, like around the streets and shopping and stuff, as I’m no where near convincing, I mean dress in like a basque stockings mini skirt and high heels , and like go walk around some woods or club or something like that, hope I haven’t upset or offended anyone xx

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By *vman64 OP   TV/TS
over a year ago

Telford


"My first time was at quest in Leeds, was very nervous and met another CD there. who calmed me down. Then met a black guy in there and had my fist BBC and ever since then I crave black cock. I really need to get some more when this blows over

I go to the 'TV Thursdays' af Quest, whenever l can get there

A most enjoyable afternoon!"

Where is Quest?

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By (user no longer on site)
over a year ago

I want to go out dressed. dont know where to go though

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By (user no longer on site)
over a year ago

I normaly go for a drive at night all dressed up and go to some wooded areas so I can have a nice walk round even get to have a bit of fun sometimes with some kinky guys.

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By *vman64 OP   TV/TS
over a year ago

Telford


"I normaly go for a drive at night all dressed up and go to some wooded areas so I can have a nice walk round even get to have a bit of fun sometimes with some kinky guys."

Sounds good, where did you go the very first time? xx

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By *ndreacdxxxxTV/TS
over a year ago

Derby

I did my first walk out of premier inn before lockdown, oh my goodness I was so nervous you can only imagine if you’ve done it, I pretended to be on my phone so had it to my ear to try and hide my face as I walked past reception, I think the lady on reception could hear my heart beating through my blouse and jacket though.

I got to my car and was so relieved but I then realised I had to go back at some stage, oh my goodness how will I cope with that, it was early evening so thought I will go for a drive, I had on knee length boots so easy enough to drive in, I drove for about 5 miles but didn’t know where to as was so nervous, I pulled in a lay-by and tried to compose myself, I put on interior light and had a look at myself and I must admit I felt I looked okay, my mid thigh leather mini skirt was not showing my stockings, my make up looked good, I wanted more excitement but not to public, maybe a service station but don’t think I was brave enough, maybe a multi story car park so as I could get out and have a walk around as I had my big red coat as well to hide my leather skirt if needed, but how do you google that, so I put in google adult shop, wow 12mins away called Pulse and Cocktails, not heard of it but wasn’t too faraway so worth a look.

Driving there although it was dark was still very exciting, then sure enough here it was on side of dual carriageway next to a garage, I pulled in semi lit car park and only 1 car here but it said open 10-10pm, I so wanted to go in but I couldn’t, I got out walked around towards entrance but then noticed camera and I bottled it, I wanted to go in but couldn’t get up the courage, I was thinking what if they reported me, what if they laughed at me and many other scenarios, so I got back in car and needed to head back to premier inn

I got back to premier inn and was flat because I hadn’t got out and walked around or saw anyone, so all this dressing up and doing make up and wig was for nothing, but then I started to get nervous as I needed to get to my room, here goes as I walked to reception entrance 2 men from adjoining pub came out and headed towards the reception entrance as well, so I stopped in my tracks and turned round pretending to be on my phone, oh my goodness what do I do, then one of them said something, so I turned around, he was holding the door open for me and gestured for me to go first, I put my hand up and held phone and said I’m ok thanks (in my best quiet female persona) agh come on love especially as your so sexy he said, oh my goodness I smiled and turned away pretending to be on phone.

He went on in so I waited as was worried they might be talking to receptionist so I checked they had gone through reception and said to myself come on you have to go in, I must be honest I was extremely flattered by what this man had said, I went through first reception door, I had my phone in my hand just in case, but they had gone and the lady on the desk was not looking, not till door went shut and she spun round and looked straight at me, well actually she just slowly looked around at the door shutting but it felt 10 times worse trust me, good evening she said, hi I replied as best as I could, she then said your looking very lovely tonight my dear, agh thank you I said, enjoy and goodnight she said, wow and what did she mean by that, as I went through doors to lift were the 2 men still there, no they had gone what a relief, well sort of

I decided I would take stairs as I just knew lifts would fail and I would get trapped, highly unlikely but I didn’t want to take the chance, so I took the 2 flights of stairs and by now I was extremely confident and wouldn’t mind my gentlemen holding the door open for me now, but nope no one around and I made my way to room as slowly as I could and opened my door and I was in the safety of my own room, I was still all dressed up and feeling so sexy ??

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By *ecretpantyTV/TS
over a year ago

lisburn

Would you have liked to be asked into one off the guys rooms for a night cap?

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By *everlyandersonTV/TS
over a year ago

newcastle

Mmmm sounds fantastic ,, yes the buzz you get when out dressed up is amazing ,I'm hoping to do it again aswell ,go for a nice long drive again as Beverly ,, I'm also going to try it during the day sometime aswell x

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By *ickey10Man
over a year ago

coventry

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By *ack Seat LoverTV/TS
over a year ago

Woking

Im going out delivering for amazon dressed up this afternoon....

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By *harlotteBrooke9TV/TS
over a year ago

Warwickshire

I love going out dressed, from my first awkward time bumping into a cyclist, many shopping trips as a totally convincing young girl to meeting guys...oh and having a complete stranger cum over my ass in a public park and leaving me exposed. Love feeling of totally being dressed up. Happy to tell any particular stories people want to hear x

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By *andybigboiMan
over a year ago

Mount Pleasant

Amazing stories!!

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By (user no longer on site)
over a year ago

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By *harlotteBrooke9TV/TS
over a year ago

Warwickshire

Had several messages asking for one of my stories so here you go:

True Story: Once I was walking through the park during the day in my blue tight flowery dress, black tights and boots. I needed to sort my boots out so I leant over the bench to get the stone out. It was at that point I felt something brush against the back of my tights and ass. I looked around and couldn’t see anything. I then noticed a guy walking away looking back at me as he went off into the tree lined path. I didn’t think anything else of it.

I began to turn back and walk back through the park, along the paved path. Part way down I looked around and the same guy - fairly well built with a medium length beard - following me. There was the odd other person around walking through, it was midday.

The guy got closer and then before I knew it, he had his hard right up my skirt and feeling up and down my tights and was fiddling with the strap of my purple thong. We walked side by side, not saying a single word. He was turning me massively on though not knowing who he was!

As we walked he got progressively more confident and rubbing all around. I needed to stop and thought I’d be nice and allow him a better view to fondle my ass without us moving. I walked over towards a tree and leant against it. This was just near the path so still the odd person walking through could have seen us.

The guy then proceeded to lift up the skirt of my dress and really start to feel my ass, squeezing it and slapping it a couple times. Then he got bit closer and started to rub his crotch against me.

Next thing I knew without warning, he started to hump me, placing his hands around my thin petite waist and pushing up against me. This went on for w good minute or two. I lost track of whether anyone was around and I hoped he was keeping an eye out since it was broad daylight right on the path.

After a couple minutes of him moaning and me being naive, I suddenly realised he had his cock out and was pushing it up against my ass. He then leant over in his final groan and said “I’ll try and be discreet” and next thing I knew, a warm hot sensation flooded my ass through my tights. I’d never felt anything like it, I was naive and young. His cum quickly seeped into my thong and onto my hole.

Once he had finished pumping away, he simply gave one final push against me and then started to walk away, leaving me bent over at the tree with the skirt of my dress up and over my hips and tights-covered ass with cum dripping down for the whole world to see.

After the shock of this all suddenly happening, I came around and quickly put my dress back down encase anyone could see. I wanted to ask how the guy knew of me and what his name was but he was already half way through the park and I was dripping with his cum. I walked through the field and sat down. Realising how much cum had soaked into the tights and my thong, I took the tights off and out some fresh ones on. However I had no other underwear so I had to drive home with cum stained panties still sweeping through into my hole.

Hope you enjoyed my story xxx

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By *urabriteMan
over a year ago

stafford

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By *aulaxd2020TV/TS
over a year ago

dudley

My first time out dressed in public was 9years ago last week I went to Worcester for a night out quite nerve wracking walking from car to the pub totally different walking on pavement to carpet at home I’ve not looked back since that night and love going out when ever I get the chance x

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By (user no longer on site)
over a year ago


"Had several messages asking for one of my stories so here you go:

True Story: Once I was walking through the park during the day in my blue tight flowery dress, black tights and boots. I needed to sort my boots out so I leant over the bench to get the stone out. It was at that point I felt something brush against the back of my tights and ass. I looked around and couldn’t see anything. I then noticed a guy walking away looking back at me as he went off into the tree lined path. I didn’t think anything else of it.

I began to turn back and walk back through the park, along the paved path. Part way down I looked around and the same guy - fairly well built with a medium length beard - following me. There was the odd other person around walking through, it was midday.

The guy got closer and then before I knew it, he had his hard right up my skirt and feeling up and down my tights and was fiddling with the strap of my purple thong. We walked side by side, not saying a single word. He was turning me massively on though not knowing who he was!

As we walked he got progressively more confident and rubbing all around. I needed to stop and thought I’d be nice and allow him a better view to fondle my ass without us moving. I walked over towards a tree and leant against it. This was just near the path so still the odd person walking through could have seen us.

The guy then proceeded to lift up the skirt of my dress and really start to feel my ass, squeezing it and slapping it a couple times. Then he got bit closer and started to rub his crotch against me.

Next thing I knew without warning, he started to hump me, placing his hands around my thin petite waist and pushing up against me. This went on for w good minute or two. I lost track of whether anyone was around and I hoped he was keeping an eye out since it was broad daylight right on the path.

After a couple minutes of him moaning and me being naive, I suddenly realised he had his cock out and was pushing it up against my ass. He then leant over in his final groan and said “I’ll try and be discreet” and next thing I knew, a warm hot sensation flooded my ass through my tights. I’d never felt anything like it, I was naive and young. His cum quickly seeped into my thong and onto my hole.

Once he had finished pumping away, he simply gave one final push against me and then started to walk away, leaving me bent over at the tree with the skirt of my dress up and over my hips and tights-covered ass with cum dripping down for the whole world to see.

After the shock of this all suddenly happening, I came around and quickly put my dress back down encase anyone could see. I wanted to ask how the guy knew of me and what his name was but he was already half way through the park and I was dripping with his cum. I walked through the field and sat down. Realising how much cum had soaked into the tights and my thong, I took the tights off and out some fresh ones on. However I had no other underwear so I had to drive home with cum stained panties still sweeping through into my hole.

Hope you enjoyed my story xxx"

Wow wow wow

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By *anabecdTV/TS
over a year ago

Limerick/ tipp

Loving these stories

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By (user no longer on site)
over a year ago

I haven't been out yet, while I'd happily go to a club,and change, I'm 6"2 before the heels, so reluctant to try.

Loved Andrea's hotel outing, I travel with work, and would love to meet another girl to hold each others hands.

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By *harlotteBrooke9TV/TS
over a year ago

Warwickshire

Glad you enjoyed the story hehe. Some more of my naive days if you’d like to hear x

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By (user no longer on site)
over a year ago


"Glad you enjoyed the story hehe. Some more of my naive days if you’d like to hear x"

Please xxxx

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By *anabecdTV/TS
over a year ago

Limerick/ tipp

Yes please

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By (user no longer on site)
over a year ago

Yes more please.

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By *harlotteBrooke9TV/TS
over a year ago

Warwickshire

Ok so here is another.

The first time I ever came across the world of dogging. I was 21 so pretty naive to it all but loved dressing up. I’d been going out dressed down a little country path outside the block of flats I lived in. I’d been fantasying about going as a school girl and mastubating outside and cumming over my tights. I decided this was the night.

I put on a black skater skirt, black tights, white blouse and school tie. I then put my boy clothes on and went out the door. Didn’t have a wig or make up at the time, it was the early days!

So I went to the country path and walked all the way to the end where you have cross a duel carriageway and it goes into a lay-by. I then walked around and spotted a quiet dark field which looked perfect. I wanted to feel the adrenaline so I stripped off my jeans but left my jacket on as it was freezing cold. I could feel the cold air wrap around my black tights and blow up my skirt, it felt exciting!

I got to the centre of the field and making sure I didn’t step into anything, I shone my mobile phone torch around. I then laid my jacket on the floor and sat down. I started to rub myself from under the skirt like the girl I am. As I got closer to orgasm, I reached under the waist band and took my cock out. It didn’t take me long and cum was pouring out all over my tights and legs. It felt amazing as anyone will agree when your outside and the adrenaline is pumping.

After coming down from my orgasm, it was at that point I looked up. There, standing just 5ft away was a large built bloke. Thinking back, likely a trucker who had spotted my torch from when began and came to investigate. It was pitch dark and I think he was holding his phone taking a few pictures or video, I’m not sure.

I froze for a moment. I didn’t expect this at all. It was 10/11pm in the dark! I regained my senses and panicked thinking he was going report me or was the land owner, I got up and ran. Cum was still dripping down my tights. I reached the bush I’d hidden my clothes in and quickly put on the jeans, consequently spreading the cum up my leg. I then very quickly walked home.

To this day, I have no idea how I didn’t hear the guy. I also wonder what would have happened if I’d spoken to him...or perhaps if I’d not been as quick, maybe he’d not given me a choice and put his cock in my mouth. I mean, I was basically on my knees already!

I’d love to talk to him now, know whether he did capture anything from that night. I’ll never know how long he’d been standing there. X

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By *eathersarahTV/TS
over a year ago

warrington

Canal street in Manchester was my first public outing Had my make up done by friend n went out dresss fully in leather I had great night n plenty off attention even ended up have Plenty fun in toilets of one of pubs Omg wish I was back there now x

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By (user no longer on site)
over a year ago

Great stories

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By *istressZoeTV/TS
over a year ago

cheshire

I went to the wonderful Kellies dressing service In Manchester it was 1996x

I had been to Kellies a few times before and had met girls there who arrived to dress safely before going out to canal street

One Wednesday I was there after work and fully glammed up x two girls arrived around 7 and got ready x after a few drinks in her apartment I was cajoled into joining them for drinks at Naps x

The thrill of my thigh boots on the canal side cobbles has stayed with me til this day x

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By *oodtime maryCouple
over a year ago

dub

well since the wife found out that i was a tv after years together she wanted me to go out dressed and i wouldn't then we heard about a tranny club not far from us so one night i had a few drinks on me and she got me to go there first time we went

i didn't dress but we have been back many times since and always dress wit the added bonus of the wife doing my make up and since this covid has us all in lock down wit now were open we have gone for walks into town and a few drives and into 1or2 sex shops

so after covid we are planning to go out a lot more and plain a trip to sparkle and London a.s.a p

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By *erry bull1Man
over a year ago

doncaster

First time was in basque stockings and panties , drove to local dogging spot and sat with door open , it wasn’t long till guys were wanking and cumming over me

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By *anabecdTV/TS
over a year ago

Limerick/ tipp

Once was dressed driving around town in my car, until I got enough courage to take a short walk up and down a dark street.

Felt great, that breeze on my stockings and up my dress.

Would love to do it again with some company

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By *everlyandersonTV/TS
over a year ago

newcastle

I can't wait to go out dressed and driving around knowing others are looking at me

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By *iAbbyTV/TS
over a year ago

Newcastle upon Tyne

I cannot wait to go to club F dressed in basque, stockings, panties, heels and wig

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