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First meeting with a crossdresser

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By *obbi_sutherland OP   TV/TS
4 days ago

Dornoch

While I had been dressing since very young and playing in front of glory holes for years, I didn't have my first meeting till I was at university.

Unfortunately due to the accommodation I was in a double room so no opportunity there.

For those old enough to remember, toilets used to be full of pornographic graffiti and I used to go and wank to it.

However amongst the graffiti downstairs in the main university block would be offers to meet up.

I replied to one, a crossdresser called Susan. Saying I would meet her.

I waited a day or two and went back, there was a reply asking when. I said a time and date.

I came back at the allotted time. Due to my double room, I didn't have anything fun to wear so went male.

I went into the toilets, the cubicle with the meeting graffiti was shut.

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By *obbi_sutherland OP   TV/TS
4 days ago

Dornoch

I went into the cubicle next to it and waited. I could hear the sound of breathing next door.

I looked down to see just the tip of a pointed patent shoe sticking under the partition. Obviously a woman's shoe.

I touched it with my shoe, more appeared. I reached down and stroked the shoe, feeling onto stocking clad leg.

Susan was there. I exited my cubicle and she let me into hers.

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By *iv JonesMan
4 days ago

cardiff

More please

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By *obbi_sutherland OP   TV/TS
4 days ago

Dornoch

It wasn't the best lit of toilets being in the basement, no natural light and the days when it was all dark wood. It was 1986.

I could smell Susan's perfume, something nice and floral.

I looked at her, she was fully dressed.

A mid length, slightly spiky wig, large round sunglasses, deep red lipstick.

A necklace on top of a black sleeveless silky top. A bracelet that matched the necklace on each wrist.

There was a dark mini skirt, not so short as you could see her stocking tops, but short enough.

Lace top hold up stockings. Black.

And then the patent high heels. Probably only 2 inch heels but sexy in the black patent leather.

She was slender, quite petite. Not even as tall as me in her high heels.

She had to tilt her head up slightly to look me in the eye.

"Do you like what you see?"

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By *anchesterMale1990Man
4 days ago

Manchester

Great start

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By *orned-toadfishMan
4 days ago

Weston-Super-Mare

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By *obbi_sutherland OP   TV/TS
4 days ago

Dornoch

I was shy as this was my first time ever with a cross dresser, and I was not exactly what you would call experienced with women either.

I mumbled yes, aware of our surroundings. I let Susan take the lead, as she was obviously much more experienced than I was.

However, even she was a bit nervous, only now much later and experienced do I realise what a risk she was taking, how much time and effort she had put into her appearance.

She reached around and pulled me to her, my whole body next to hers, smelling her perfume but feeling her shaking a little as well.

Her lips were a glorious shade of red, all glistening, she placed them on mine, I could taste the lipstick, feel the texture of it as it transferred to mine.

I wrapped my arms around her and kissed her in return. My tongue flicking out of my mouth in a wee exploratory motion between her lips.

I heard her softly moan.

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By *nly1meMan
3 days ago

here there n everywhere

love to hear more x

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By *ucksguy2000Man
3 days ago

aylesbury

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By *urabriteMan
3 days ago

stafford

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

We kissed as we wrapped our arms around each other, pulling ourselves tight together.

Running my hands up her back I could feel her bra strap under her top.

The softness of her breast forms pressed into my chest.

My head tilted slightly as we forced our tongues into each others mouths.

Susan broke away and nuzzled herself into my neck, it felt so good her mouth and face on my skin there.

But I wanted to kiss her more so used my hands to hold her head as I locked my lips on hers again.

I pressed my body against her, forcing her small frame backwards, pinning her against the cubicle wall with my weight.

Her hands were under my teeshirt her fingers on my skin, stroking me, encouraging me to kiss her, to push against her.

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

Susan grabbed the hem of my teeshirt and pulled it up over my head in one quick movement, I didn't resist in anyway, leaning forward to help it come off.

We embraced again, I slid my hands under her top feeling her soft back under my fingers. She gave a little shiver as she bent her head and kissed my chest, the last of her lipstick coming off onto my skin.

At this point we heard the main toilet door open and both froze, arms around each other.

We kept very still as we waited, heard him pee, then wash his hands and then the door went again as he left.

Didn't realise how tense we had both been until the door closed again and we both gave out a big breath.

It energised us.

Susan started to undo my jeans. Safe to say I had been fully erect for a while now. Something she could not have missed during our embracing.

I had been aware of her clit, all aroused in her panties. I reached down and rubbed her hardness through her skirt.

My jeans were down to my ankles, my boxers like a tent.

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By *hemarcus2376Man
3 days ago

gorseinon

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

She placed a hand on my chest and pushed me back against the wall on the other side from her her. I hardly noticed the coldness of it.

I looked down to see her use two hands on the outside of my boxers, through the thin cotton she scooped my balls and then ran her fingers up my shaft.

I thought I was going to explode there and then.

Her fingers continued up and then hooked the elastic of the waistband and pulled them down. My cock sprang out. I don't know if I had ever been so hard before that moment in time.

"Nice" was her response.

She kissed me again on the lips as her hand wrapped around me and she gently massaged me.

Her thumb and forefinger in a tight loop around the base of my cock, her other three fingers stroking me.

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By *icki222TV/TS
3 days ago

Lincoln


"She placed a hand on my chest and pushed me back against the wall on the other side from her her. I hardly noticed the coldness of it.

I looked down to see her use two hands on the outside of my boxers, through the thin cotton she scooped my balls and then ran her fingers up my shaft.

I thought I was going to explode there and then.

Her fingers continued up and then hooked the elastic of the waistband and pulled them down. My cock sprang out. I don't know if I had ever been so hard before that moment in time.

"Nice" was her response.

She kissed me again on the lips as her hand wrapped around me and she gently massaged me.

Her thumb and forefinger in a tight loop around the base of my cock, her other three fingers stroking me."

Mm...this is so yummy 😋💋💋

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By *ameulMan
3 days ago

Nr Norwich

This is so erotic!!!

Please keep going.

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

With my back still against the wall, Susan leaned down and kissed my cock.

My first ever oral contact on my cock.

It felt so good.

She took the tip in her mouth. How I didn't cum there and then I didn't know.

She ran her tongue around the head of my cock. I leaned back and enjoyed the sensation.

Looking down, all I could see was her wig as she moved her head back and forth.

I put my hands on her shoulders, gently squeezing her, showing my appreciation.

I pushed her off me, not wanting to cum yet and she stood up so I could kiss her.

I could see a mix of her saliva and my precum on her lips and I licked it before kissing her.

I could taste me on her. (I was no stranger to the taste of my precum and even my own cum)

My hands went down her front. I reached and lifted the hem of her skirt. I wanted to feel another cock for the first time in my life.

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch


"This is so erotic!!!

Please keep going."

All completely true.

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By *andyel73Man
3 days ago

Leyland

Hmmmm can't wait to hear more

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

It was now Susan's turn to be back against her side of the cubicle. Her skirt lifted up.

Her cock was straining against her black lace panties. She reached down and slipped her panties off, down her stocking clad legs. She stepped out of them entirely.

I was looking at her cock, and then for the first time in my life I had another cock in my hands.

She was not big, in fact from my experience since it matched the rest of her, quite petite.

But it felt so good nestled in my hand. Susan must have thought so too as she made some appreciative noises.

I wrapped my fingers around her hardness, and watching myself, I slowly wanked her. Nice and slowly.

She was arching herself now, her neck all exposed.

I leaned in and kissed her neck as I played with her, tasting her perfume. Enjoying her feminity.

I was only 19 and as yet sexually inexperienced but Susan must have been in her 30s or 40s. Difficult to tell when you are that age, everyone older than you appears old!

I was moving my hand faster when she stopped me and turned herself around.

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By *eterpervisMan
3 days ago

back where i came from

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By *tephine DommeTV/TS
3 days ago

Waterford

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By *istresskaty1981TV/TS
3 days ago

brigg

Love where this is going xx

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By *olflordMan
3 days ago

Exeter

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By *ickyxxx99Man
3 days ago

Lewisham . Se London

Loving this, sexual encounters in public toilets was I big part of growing up for me. First time I had my cock sucked was through a glory hole with my legs shaking and I'm thinking oh my god what's just happened to me.

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By *aximumperversion2Man
3 days ago

All around the place

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

I ran my hands over Susan's ass, it was smooth and hairless, just like her cock and balls. Can't remember if I said that earlier.

My hands came to a halt on her thighs on her stocking tops.

She twisted her head and told me to fuck her, but I'd need to remove something first. I felt in arse and there was a wee string, I pulled a tampax slid out of her. She'd been using it to keep her ass full of lube.

A finger slipped up inside her easily but it wasn't what she wanted.

Now at this point I could pretend that I was some sort of teenage superhero and fucked her vigorously for hours but I shall stick to the truth.

Nerves overcame me as I moved closer, the height difference meaning I had to bend my knees somewhat as she spread her legs. I lost some of my hardness as I tried to enter an ass for the first time and failed miserably.

But she very understanding and gentle and helped guide me into position. I hardened at the feel of her hand on me, making sure I was at the right angle, "Push" she said and I followed her instructions. It was tight, very tight but slowly but surely it was sliding into her.

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

The fucking started slowly, as much Susan moving back and forth on my cock as me thrusting into her.

But it soon became a mixture of the two before it was definitely my thrusts pushing her forward, pushing her onto the wall.

My hands still on her thighs, pulling her towards me as I pushed my cock into her.

She was playing with her own cock with one hand and bracing against the wall with the other forearm.

It didn't take long but my breathing was giving away that I was about to cum, my thrusting deeper but slower when with a grunt I started to cum, I slid my arm around her and held on as my cock spurted what seemed like stream after stream of cum up her.

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By *obbi_sutherland OP   TV/TS
3 days ago

Dornoch

Susan held onto my arm that was around her, not letting me go, as she worked her cock with her free hand.

She came with a wee moan and everything relaxed. Some of her cum landed on my trainers, a small price to pay for the experience.

I could feel myself slowly shrinking and sliding out of her, my cock and pubes covered in a mix of lube and my own cum.

Susan stepped back into her own knickers and pulled them up.

I pulled up my boxers and jeans. The cubicle which had seemed ample room for the two of us to play and fuck now seemed very small and we kept bumping into each other. I reached down and found my teeshirt and popped it back on.

Susan told me I should go first, I slowly opened the door, made sure that the toilets were empty and made to leave.

She gave me a peck on the cheek and said "Thank you". I thanked her back and left.

Am not sure why, but I never managed to arrange another meeting with her. She didn't put any more messages on the back of the toilet door not even in response to mine.

There have been many adventures since that one but even now, after nearly 40 years I can recall every moment of this first time with a crossdresser, all 15 minutes or so of it!

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By *eterpervisMan
16 hours ago

back where i came from

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By *usie pTV/TS
13 hours ago

taunton

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By *rishman30Man
13 hours ago

Holywood

Very horny, thank you OP xx

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