FabSwingers.com forum: My first time crossdressing meet (true story)

By *mmy_sextoyslave OP TV/TS
10 weeks ago

Walsall

Hi everyone I'm going to tell you about my first dressed up experience which is totally real. Hope you enjoy

Weeks and weeks I'd slowly been treating myself to various online shopping. Getting all the basics covered. Plenty of outfits. Heels and thigh boots. Various types of make up. A few big purchases which included my very first silicone fake breasts. I was finally doing what I'd craved for a very long time. Becoming ammy, and it was such a thrill to think my journey was about to begin.

I still lived with my parents at the time so everything was very discreet. Hiding my collection. Picking the right time to try everything on. Practice make up and really get to know what turned me on and what I wanted to experience.

I started browsing online sites and gradually adding photos of me as my inner cock craving cross dresser ammy. I loved the attention and messages I was getting.

Experience wise with males. I'd only ever had a few meets in male mode and only ever gave a number of bjs. I was very eager, very turned on by the fact I craved soo much more than this.

I remember the day like it was yesterday. Thinking of my first time still gets me going soo much. I'd been talking to a local Asian taxi driver for about 2 weeks. The messages we had been sending each other constantly got my girly cock throbbing hard. He understood I couldn't accommodate and was soo keen to be my first meet while I was dressed.

A Sunday morning we got chatting. By dinner time we had agreed he would pick me up and take me to a house he was renovating. The plan was for me to dress and leave my house when it was dark outside. The timing could not of been any better as both parents were out. He asked me to wear some stockings. Ankle boots. Pvc mini skirt. My fake boob's. He insisted I wear some cheap nails and a short blonde wig I'd sent pictures of me in. He wasn't too bothered about full make up. Aslong as I had lipstick on and fully shaved. That was my first time using hair removal cream. Everywhere, smooth. I felt amazing. I had a little black pair of knickers on which matched my black bra. I agreed to walk round the corner at half past 7. I managed to hide 90% of my clothes under a long coat it purchased.

Half 7 arrived and he messaged saying her had pulled up round the corner from my house and to walk round. My belly was full of butterflies. My little girly cock was leaking pre cum before I even stepped out the door. This was it. All this build up. It was finally happening...

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By *eekingfun999TV/TS
10 weeks ago

whitstable

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By *harlotte39cdTV/TS
10 weeks ago

rochester

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By *ndisMan
10 weeks ago

Liverpool

Nice start.

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By *olflordMan
10 weeks ago

Exeter

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By *ark_sentinelCouple
10 weeks ago

Andover

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By *obtvloverMan
10 weeks ago

bideford

Nice start more please

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By *otfoot377Man
10 weeks ago

Chingford

Sounds fantastic

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By *ecretpantyTV/TS
10 weeks ago

lisburn

More please let the precum flow.

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By *inkycdxxxTV/TS
10 weeks ago

wrexham

Love dressing up sluty for guys to wank over me in panties and white ankle socks xxx

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By *iona38ddTV/TS
10 weeks ago

north east fife

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By *idlothian manMan
9 weeks ago

midlothian

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By *lwayslooking22Man
9 weeks ago

newcastle

Love a guy in sexy lingerie love to have dressed fun with a guy

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By *orned-toadfishMan
9 weeks ago

Weston-Super-Mare

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By *amieforfun1973Man
9 weeks ago

bognor regis

Let’s hear more

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By *issyswitch9TV/TS
9 weeks ago

Gateshead

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By *mmy_sextoyslave OP TV/TS
9 weeks ago

Walsall

Hood up on coat. Zipped up as I tried to leave my house as quickly and discreetly as possible. Was such a thrill just knowing people could see my ankle boots and bottom half of stocking. Door locked and I headed round the corner looking for his taxi car. I soon spotted it parked up on opposite side of the road. Our eyes locked as he had his window down. He looked me up and down and smiled and told me to get in.

Oh my God the butterflies were next level. I was finally doing it. Before I even sat my bum down on his seat. My sissy clit was semi hard. I could feel it in my girly knickers. Seat belt on and we pulled away. Just after 7.30 pm. He was wearing some Adidas joggers and jacket. Base ball cap. I could smell his strong aftershave. Mature guy, slight stubble. Id say early 50s. Which in itself was a turn on for me.

Within the first minute of us being on the road heading to somewhere he said he was working on and had the keys for, his hand jumped off the gear stick and nestled on the top on my thigh. Lift that coat up please show me what's underneath. I did as I was told. He ran his hand from my knee to my black knickers. Someones excited I see he said. There was a significant buldge on show. I couldn't help it. I put my hand on his, he commented on nails and said I looked stunning. I'd never had a compliment in the flesh like that. I loved it.

It's was while I had my hand on his while we we chatting. I felt a ring on his wedding finger. I looked down and didn't say anything. It made me feel soo naughty. He then said something along the lines of this was our little secret and he wanted me to give him the attention and rudes he wasn't getting regular at home. I said thats exactly what I wanted and would love to be his naughty bit on the side.

We're not far from the house now he said. But you've got to do something for me when we pull up. Your going to take that coat off and walk to the house dressed like the naughty girl you are. Nobody around her knows you. You might not even be seen but I want you to get used to being out and about fully dressed and accepting who you are ok. I said that's fine. Inside the butterflies were back.

Hi clenched my hand and placed it on his semi hard penis. What do you think of this. I was lost for words and think I mumbled out something along the lines of I couldn't wait to get it in my mouth. Well it will be as soon as we're in that house he said. We're here now.

We pulled up and parked up in a car park. There was a row of house opposite. About 100 yards or so away. Here's the key, number 22 he said. Go let your self in and wait for me in the middle lounge. I undid my seat belt. My long coat was chucked on back seat. I'll be in after you in a few mins. Go get yourself comfy her said.

Wow I thought. I was now walking across the car park, passed about 5 houses, full girl mode. Ankle boots, stockings. Knickers. Finger nails. Red lippy. New wig. Fake boob's, body stocking and pvc mini dress. Not sure if anyone saw me through any of the windows but it was such a thrill. I'd never walked so fast.

I got to the front door. Drive was covered in old house stuff and skip full on what seemed to be old kitchen etc that had been ripped open. I took a few steps into the hall. It smelled of fresh paint. 1st longe her said, so I carried on walking and entered the 1st room on my left. The room was stripped back. No carpet. Looks like it was being plastered. In the middle of the room there was a double mattress with few towels chucked on.

The room was lit up by a plugged in lamp in 1 corner. Next to the bed I clocked a few condoms and some lube. I pulled my stockings up and just sat on the end of the bed. I was soo turned on. All this build up. The time had come.

I head the door open and heard it get locked. HOPE YOUR READY MY LITTLE NAUGHTY SLUT he shouted. Your mine for the next hour or so now. He then walked into the room. Looked at me a said perfect. It's about time. He walked to the end of the mattress. My head level with his groin. He looked into my eyes and said now show me how you suck this cock. It's all yours from now..

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By *eekingfun999TV/TS
9 weeks ago

whitstable

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By *arenbabesTV/TS
9 weeks ago

near ashington

Wonderful! It’s taking me back to some of my early ventures outdoors. Such a thrilling read, can’t wait for more x

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By *eterpervisMan
9 weeks ago

by the river.

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By *tephine DommeTV/TS
9 weeks ago

Dublin /Waterford

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By *rash26775Man
9 weeks ago

all over

Looking forward to more

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By *harlotte39cdTV/TS
9 weeks ago

rochester

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By *igkidexyMan
9 weeks ago

Dublin

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By *usie pTV/TS
9 weeks ago

taunton

:- Frigging hell.

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By *aul 6870Man
9 weeks ago

Wolverhampton

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By *din_DomMan
9 weeks ago

East Calder

Brilliant read

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By *rishman30Man
9 weeks ago

Holywood

Very hot

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By *hythmic DriverMan
9 weeks ago

Croydon

Loving this story. Very distracting whilst I work 😉

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By *lare_thomas38TV/TS
9 weeks ago

my town

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By *ateworkMan
9 weeks ago

the country

Oh wow I’d love to have someone that dressed for me

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By *issy_slut_cdTV/TS
9 weeks ago

Exeter

Love the story

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By *obtvloverMan
9 weeks ago

bideford

She started nice and slow but always going in as far as she could pressing against me after a few minutes she start to speed up it most of got her in the right spot as she started to moan getting faster pounding me harder and hard soon she screamed she was cuming pounding me faster and faster till she stopped pulling out leaving me gaping she told me to stand up and she got on the bed on all fours telling me fuck her and be quick about it I got on the bed slipped my rock hard cock in her in one move and fucked her fast and hard going balls deep each time bang her as hard as I could I only last 20minutes till I started to cum shooting 2 or 3 good squats in her I pulled out,looking at her hubby she told him to clean up 1st he licked misstress pussy clean then turn to me he licked and suck my cock and balls clean,Misstress stood and picked up her coat and told him to dress which he did just before going misstress said she will come back tomorrow morning for a quickie before breakfast if I liked, yes please I replied ok 8am be ready ….

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By *harlotte39cdTV/TS
9 weeks ago

rochester

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By *ark_sentinelCouple
9 weeks ago

Andover

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By *yrwolfxxxMan
8 weeks ago

City centre

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