Mentoring a Crossdresser in Berlin

Once I had put a condom on I gave her a nice long hard fucking, slowing down several times to draw out my orgasm.

As I did with her, Sasha removed my condom and licked me clean.

After we had slipped in to some silky gowns we discussed at length what we would do next.

We agreed that a hotel meet would be nice....with a public sortie included. We agreed that it would be best and most efficient if we met at her apartment and caught a taxi to my hotel. A lengthy discussion followed about who should dress, or both of us. Sasha was the local and absolutely did not want to be recognised en femme but she would have far more chance of being recognised as a guy.....and a guy who was with a somewhat passable crossdresser.

We arrived at the conclusion that we should both dress but very 'safely' so as not to draw too much attention. Safe on the outside anyway.....underneath all manner of lingerie and nylon would be pinching at our flesh. We didn't talk any further on what we should wear but Sasha had the day off to organise and think about it.

The waiting was so desperately tantalising.

Hotel meet Wednesday night

The next day I arrived at around 6 pm again. Of course Sasha was already made up. She was there now....she could do herself nicely on her own. She was just mincing around in 60 denier glossy tan nylons and a silk kimono. I could tell she was a bit nervous. I was nervous also.

I had decided to wear a beige, long pleated skirt with a simple white shirt. As it was autumn I wore a burgundy Kashmir scarf. Over this I would put on a long camel coloured trench coat that I had bought on the way over to hers. Footwear would have to be pragmatic....I don't claim to be the best walker in heels although I absolutely love wearing them. I opted for a pair of pink girly style trainers.

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That was the safe bit......underneath I would be wearing a pink silky thong, a beige rago 6 strap girdle. For the all important nylons, a base of 60 denier glossy tan nylons similar to the ones Sasha was wearing last night and a pair of 10 denier, light tan, fully fashioned seamed Cervin stockings. The solid pink hem would go nicely with my silk knickers.

I chose to make my makeup more subdued, all very mat, including the lipstick. I chose a chestnut mid length wig that would sit tidily on my shoulders.

We discussed Sasha's attire at length.....we decided on a pair of navy stretch fitted trousers and some 2 inch white pointy heels. On top she would wear beige turtle neck silk shirt with a bow on the collar, which was irrelevant in public because she would wear a mid length button up coat, nicely cinched at the waist. While she was putting on her burgundy coloured gartered bodysuit and the 20 denier Matt stockings I took the pleasure in sucking her to near full hardness. She wore a long flowy Auburn wig tied back in a ponytail. And yes her suspender straps were visible through the navy trousers but only just!

We enjoyed a smoke and a glass of bubbles while waiting for the taxi.

Of course she would have to do the talking and we agreed no talking in the taxi.

With handbags full of toys, condoms, lube and other necessaries, we took the lift down with hearts pumping!

We hopped in to the black Mercedes and Sasha quietly gave the name of the hotel.

For the entirety of the journey we didn't say a word and looked at our mobile phones, exchanging a few naughty messages on WhatsApp.

When it came time to pay Sasha simply handed over her credit card and uttered a simple 'danke'.

Once out of the car a bellhop asked if we had any bags. Again just a one word answer from Sasha.

There was moderate activity at the hotel, it was around 8pm. We walked side by side through the lobby. I did have the pleasure of seeing us both in a large floor to ceiling mirror....we scrubbed up alright.

When waiting for the lift an elderly gentleman joined us. We entered all 3...he was going to the third floor, us to the fifth. Once he left the elevator I breathed more easily and gave Sasha's ass a god squeeze.

I let her get out first and indicated to the right. I followed behind enjoying the view of her bobbing ponytail and the heavy scent of eternity perfume. I was however fully flaccid.

Once in the room we didn't speak at all for a few minutes. The thrill and success of us both performing our first crossdresser outing required some reflection. We took off our coats and eventually embraced.

After some time and a smoke on the balcony we made love.

All very conventional with me poking her pussy, standing on the edge of the bed with her lying down. I did indulge in a cum exchange by removing my filled condom and placing it over her shaft so her member was bathing in my cum. Once she has fucked me and orgasmed I removed the rubber and locked and sucked her cock clean before engaging in a deep cummy kiss with her lips.

I must have dozed off because when I woke at midnight Sasha was gone.

I realised she must have had to go out en femme by herself.

I texted to see was ok.....it was all good.

Dayshift Thursday

On Thursday I woke around 7. About half an hour later I got a message from my work that there had been a fire alarm incident at my work and no access would be available until further notice.

BONUS!!!!

I texted Sasha immediately to see if she could come over to my hotel. Not until about 10 but she was coming.

I got online to do what work I could and clear my calendar from 9:30 to 3:00.

I decided that Sasha could do my makeup and be the boss.

She would be arriving in guy mode so I would have give her the bathroom to prepare.

I applied some basic foundation and a blonde bob wig so I wouldn't be in total guy mode when she would see me.

Firstly I needed to shave all over since it had been 3 days since I last did I it.

I cleansed my passage and inserted my but plug.

What to wear? I settled on a more casual look given it was during the day.

It felt like a pink day....

20 denier pink nylons and a long sleeve plain pink bodysuit with a turtle neck. Bra and size C silicon inserts obviously. So that was quite simple.

On top just a plain white stretch mini skirt that finished just above the knee.

I didn't feel the need for any footware.

I layed out the makeup with the colour elements of pink eye shadow and a soft pink lipstick.

When I came out of the bathroom the sun was streaming through the window on to the bed. It was a beautiful, clear November day. It all gave a very relaxing rather dreamy feel to the scene.

I then realised that I had never actually done anything with Sasha during daylight hours.

I relaxed on the bed in the sun and waited for her.

She messaged just before 10 and I then left the door ajar so she could come in.

When I heard the door click closed I made myself a cup of coffee.

I hesitated before I stepped outside on to the balcony to enjoy a cigarette with my coffee.

Why shouldn't I be visible in public I asked myself. I had been out last evening fully dressed, I was dressed as a girl now despite only minimal makeup and who could really tell from the 5 floors away?

A few minutes after I came back inside Sasha appeared from the bathroom.

She was wearing shiny white 20 denier nylons and a pale gold mid calf length pleated skirt. On she wore a white long sleeve chiffon shirt with a pink lacy bra clearly visible underneath.

Her hair piece was a dirty blonde, wavy shoulder length number.

Her makeup effort was really very good now. The gold eye makeup went nicely with her skirt. Lipstick was a pale red/pink hue. For foot ware Sasha had chosen a pair of blush pink 2 inch heels.

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Sasha was quite excited when I told her that she had to do my makeup.

We laughed that this was the last part of her training.

We went to the bathroom and did the necessary. I found this sublimely relaxing.

I only had to make a couple of minor adjustments at the end.

We then made our way towards the sunshine filtering through the sheer curtain on to the bed.

Oh how the sunlight caught the sparkle of her nylons!

I made us a couple of coffees and we popped on to the balcony for a smoke.

The sunshine was making us so relaxed.

We sat down in chairs beside each other and I hooked my right leg over her left thus dangling my calf in between her legs and resulting in some divine nylon rubbing.

That got us both a little aroused from our super relaxed state.

We went inside and Sasha lay on the bed with her calves and feet dangling over the edge of the bed. She stretched her arms back which heightened the bulge under her nylons. I licked her hard cock through the nylons until it was totally firm. At this point I engorged her cock and sucked until I tasted her sweet, salty precum. Now I stopped and moved to a half sitting position with my back against the head rest if the bed. Sasha took my cue and followed me up to curl up beside me.

She leaned in to give me some gentle kisses and rubbed my semi hard cock through the nylons and bodysuit.

Once fully hard Sasha lay flat on her stomach and place her head under my white skirt and started sucking my shaft.

After a few minutes I broke free and stood at the edge of the bed. Sasha took my cue and lay face down on the bed with her ass on the edge.

I lifted her pleated skirt and tore her white nylons.

I generously lubed up her ass crack and started fucking her cheeks.....I had no real intention of penetration so no condom was needed.

With plenty of lube I could squeeze her cheeks together to increase friction.

This way Sasha got an nice anal massage.

When I could feel my orgasm rising I released Sasha and wondered what to do next.

She had the perfect answer.

She got up and went to her bag and came back with a pair of scissors and a couple of condoms.

After fully lubing her own cock (mine was already glistening with lube) Sasha opened the condom and cut the end of with the scissors.

She then slipped it over my cock so my head was poking out the end.

She gestured me to lay down on my back on the bed with my feet on the floor

She then stood and faced me and moved in so our cocks were touching.

With a bit of stretching she then squeezed her own cock in to the same rubber sheath.

Slowly but surely she started pumping so both our cocks were rubbing together.

To keep everything in place she had to lightly grip both of our members in one hand.

I loved this. It was new and super sensual. It perfectly suited our lazy mood that day.

The sheer friction resulted in a near climax for both of us. When we were both close she slowed to draw it out for longer. She could have gone on for hours like this.

When the time came for the big release she repositioned the condom slightly so that her cock was also poking out the end.

I exploded first shooting a couple of big spurts over my pink body suit as far up as my right breast. Just as I had finished cuming Sasha did the same but reached the underside of my chin.

Relaxed and contemplative Sasha leaned in to lick up the few drops of her own cum under my chin.

I thought this was a perfect opportunity to clean each other up so I removed the misused condom and we got in to a 69 position to lick each others cocks dry.

After rearranging ourselves in the bathroom we lounged in silk gowns and glossy nylons.

We discussed what we would do the next evening as we both came to realise that it would be our last.

We both agreed that it would be a full cocktail, dress up evening.

Sumptuous gowns, glamorous make up, high heels and pin up lingerie seemed only appropriate.

Where we needed a lot more discussion was if we should invite a paid third party to join us and what form they should take.

This revealed both our fantasies.

I was keen for a young super smooth twink or a mature pin up vixen.

Sasha was more keen on full professional tranny or a young voluptuous female.

Of course deep down we would have made the most of any of these options.

But fundamentally we needed to decide if we wanted to share another cock or branch out with some lovely pussy.

I liked the idea of being fucked twice by two other cocks, servicing the other one with my mouth while it was idle.

A nice pussy would have the advantage of the possibility of double penetration.

Of course we didn't have to invite anyone at all.

We ended up agreeing on a smooth, sleek, 21 year old sissy boi.

Finding him was quite quick. Sasha obviously spent a fair bit of time perusing the web looking for this kind of thing.

Mikael was 21. He looked super androgynous and had the most gorgeous ass.

What sold him was the photo of his arrow straight erect cock pointing down his left leg under a pair of 10 denier tan nylons.

I insisted that he was totally smooth and wore nylons under his trousers.

Liberal perfume and clear lip gloss would also be appreciated.

We made it quite clear what we would be doing.

We thought that we would want a bit of time to ourselves first, a couple of hours so we asked him to arrive at my hotel room at around 9.

The choosing of our assistant and the excitement about tomorrow evening forced us in to orgasm my mutual cocksucking.

By about 6pm Sasha had left and I turned in early to bed.

Cocktail party Friday

What to wear???

This was obviously the night where we were going to go all out.

I recommended starting from the inside out.

As a base I chose a pair of glossy tan crotchless tights and a pink satin thong with white lace front panel. Then of course my pocket bra with D size silicon inserts.

Some Rago shapewear came next, a beige, full open bottomed girdle with the obligatory 6 suspender straps. For stockings I chose some full fashion heel, seamed beige Cervin with pink welt.

I had chosen my favourite above knee length, salmon sequinned dress with 3/4 length sleeves. The sequins were only from the waist down. The top half was a of stretch material that just revealed the lace patterns of the Rago girdle. To highlight my waist I added a gold metal hoop belt that fit nicely thanks to the cinching effect of the Rago girdle.

Shoes were a 4 inch heel, one inch platform, cream coloured with a flower over the toe.

Pearl necklace and bracelets, large hooped earrings complete the ensemble.

I agonised over the wig a little but I settled on a long flowy blond wig that I could

tie in to a nice bun.

For the makeup I really went to town, matching my salmon sequins with pink eye shadow and bright red lipstick.

Because I could, I added a fine pearl ankle bracelet. That would be my ensemble, well for at least the first 15 minutes until layers would be lifted, stretched and generally discarded.

For Sasha we decided on a blue theme.

Like me glossy crotchless tights and pocket bra with D size silicon inserts on first. Then a navy blue long sleeve bodysuit that was of lurex material from the hips up. On top of this we would have to add a suspender belt (this night without suspenders and stockings would seem inappropriate).

Mikael looked exactly as advertised on her site.

He was wearing tight blue capri pants (bulge clearly visible), black trainers and a plain white t-shirt. His lips were already glossy....I loved that.

After basic introductions we handed over the fee and let Mikael do the necessaries in the bathroom.

Proceedings started with Mikael standing in only a pair of black crotchless tights and Sasha and I on our knees either side of him.

I was on the front side and started licking his soft, cut member.

Sasha was on his back side and started with her tongue on his delicious behind.

Once fully aroused I stood to kiss his glossy lips. Mikael put his arms around my waist to pull me in to the embrace.

Sasha continued to pleasure him from behind.

After a few moments we made our way to the bed where all manner of spit roasting ensued. Of course Mikael was the first to be plundered, first by Sasha then me.

In total we each orgasmed 3 times with varying degrees of situations, intensity and duration. Between us we used up an entire one dozen pack of condoms.

Apart from the odd pause for wardrobe adjustments and cigarette stops, it was basically non-stop for about 5 hours.

During one of these pauses while Sasha was fixing herself in the bathroom, Mikael and I found ourselves face to face with me lying on top. I had just pumped his ass for the second time and Mikael had delivered her load on to Sasha's face.

He pulled me in for a sloppy kiss then held me and rolled us on to our sides. Here in our locked embrace we enjoyed a tender intimate moment of hugging and kissing.

It was all very intense and exhausting. the sex had started around 10pm and we finally collapsed in to bed around 3am.

Extras:

Sasha was the first to wake around 9am. Sasha and I had slept in the king bed while Mikael collapsed on the two seater couch.

At about 9:30 Sasha reappeared from the bathroom lightly made up and wearing a pair of black exercise tights and her long winter coat. She had her plain brown wig on and some pale blue trainers. I could see her suitcase was packed and she was ready to leave.

She approached the bed, carressed my thigh and pecked me on the lips.

"Thanks" was all she said. With that she left. Not overly emotional at all which was quite surprising given the torrid week we had just spent together.

The clicking of the hotel door awoke Mikael. He went straight to the bathroom.

He was in there for a while. I had a small panic about how I looked after the torrid night of three way sex.

I stood only to look at myself in the mirror beside the bed. I had slept in a pair of pantyhose and a silk shirt....yes I remember now.

My makeup was a bit worse for wear but not terrible. I straightened my wig and redid my lipstick (always handy beside the bed).

I lay back down and started to nod off again.

Mikael appeared from the bathroom looking remarkably fresh. Wearing only lip gloss and a pair of my pink, baggy silk tap pants she sat down on the edge of the bed without saying anything.

She started stroking my member through the pantyhose until I was aroused.

"This is for free" she simply stated.

With that she tore my pantyhose and wrapped her glossy lips around my 3/4 erection.

After a few minutes of sucking I was fully hard. Mikael found a condom and rolled it down my shaft.

She then straddled me, easing my cock up her pre-lubed back passage, pulling the baggy tap pants to the side.

Once fully impaled Mikael rode me and leaned forward to kiss me.

This was fantastic.......I had done nothing but lie there......and it was compolimentary! Should I tell Sasha?

As my orgasm started to rise, Mikael sat up and started to stroke his member will still pumping me.

She did a magnificent job of timing her orgasm straight after mine. She spilled her load on my silk shirt.

Once he had caught his breath he got up and removed my condom. Mikael then proceeded to lick and suck my semi soft cock clean.

Once this was done he leaned in and kissed me on the lips and neck, very gently and intimately.

Without saying anything he got up and went to the bathroom and left about 15 minutes later.

It was now almost 11am I needed to clean up and pack. I managed to delay my flight until 3pm.

What a night! What a week! And what a mess.....

Since I have had a few awesome sessions with gurls but not for such an intense and sustained period.

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