Mentoring a Crossdresser in Berlin

Intro:

I have been a crossdresser for many years.

I have become really rather good at it.

It is a big sexual turn on for me.

I am married so only could indulge when I travelled which was frequently.

I often looked for hookups but this was tricky and had only happened a few times.

I had been living in Germany for much of my cross dressing life. I now found myself in the UK but travelling regularly back to Germany.

I would trawl the meeting websites usually to no avail.

One day I received a message from an admirer announcing themselves as a beginner looking for some guidance.

After a few exchanges we agreed that I could be her mentor.

Sasha was 23 (to my 42) and stood at at 173 cm. Sasha was quite thin and neutral looking in terms of gender.

She had a few photos of her in rather tacky dresses but no facial pics other than the one of her as a clean shaven, buzz cut guy.

We agreed that the first step was to sort her wardrobe.

Over a period of about 3 months I directed Sasha to purchase all manner of feminine items.

Silicon breasts, heels, lingerie, wigs, nylons. I particularly enjoyed selecting dresses for her. I basically chose things that I would like to wear.

My style is very chic secretary. Nothing slutty. Pearls, rago shape wear, usually a little more demeure than those I interacted with.

Sasha kept insisting that I should teach her makeup. I said this was really impossible online and would best be done in person.

She grew quite frustrated at our not being able to meet but I kept her enthused with my constant expression of admiration of her improvement in dressing style.

And then the opportunity arose. She lived in Berlin and work needed me there for 4 days that I would end up turning in to 6.

We got to work buying her makeup and the final bits of her wardrobe. Including a butt plug.

I booked a hotel nearby which meant that during the day I would have quite a long commute to go to my place of work. Too bad.

Although we didn't talk about sex much it was quite clear that this was part of the enjoyment for both of us.

As I was her mentor we agreed that once she was ready I would be able to help myself to the spoils of my subject.

I packed as much of my wardrobe as I could. I knew that if this worked it could lead to several evenings of crossdressing sex.

Although I only needed to be at work on a Tuesday, I flew out on Sunday afternoon.

I have never been one for going out dressed in public so we arranged that I would arrive as a guy and change there.

Prior to my departure I shaved completely. Sasha did the same.

We agreed she should be wearing some basic lingerie when I arrived. I would then do her make up and fully femininize her.

Enemas were totally compulsory, and if she thought it took 5 minutes then she should do one for 20. Me the same.

First encounter on Sunday

I arrived at about 8:00pm on a Sunday night. After I was buzzed in I went to the 3rd floor and found the door of her apartment ajar. As agreed I found the bathroom and preceded to get ready. We agreed that it could be weird if we were to see each other as guys at our first meet so Sasha was waiting in the bedroom. The bathroom was spotless, with a shower, chair and a decent clean surface for makeup and accessories.

I decided to go for my classic look. Glossy, tan 10 denier pantyhose, Burgundy bodysuit, silicon breast inserts. A knee length, floral print pencil skirt and a blush pink silk long sleeve shirt buttoned up to the neck. 4 inch beige heels complimented my height. The wig I chose was long, wavy blond that I pulled back in to a pony tail. A necklace of pearls, pearl bracelets completed my look. I took extra time with my makeup as I was supposed to be presenting myself as an example by now. I love the final act of putting on bright red lipstick, such a turn on for me. As is typical, by now I was rock hard...and a little nervous. I'm sure Sasha was also.

All this took about 45 minutes...when I was done I gently called out "ready".

Sasha gently tapped on the bathroom door.

My first impression was one of relief. She looked just like in our zoom sessions. 173 cm, brown buzz cut hair, thin without being scrawny. Her face was gender neutral. Very androgynous overall. She was wearing a pair of 20 denier glossy black nylons and a black mid calf length négligé with cream lace trim.

The second thing I noticed was that Sasha was liberally perfumed with Dolce Vita...as requested.

She looked nervous which was normal. I leaned forward and hugged her. She commented on my stylish looks.

After some brief small chat I suggested she sit down in the chair so we could get started on her makeup.

After applying some foundation I left to get a stool from the kitchen to save my back.

Neatly poised on the stool I started on her make up. This is far more difficult than on oneself. Although I am good at it on me, it is quite a different skill to to the make up of someone else.

The occasional friction of our pantyhose was mutually appreciated.

It took time. I opted for a heavy set makeup to be on the safe side.

I think Sasha enjoyed the final lipstick application as much as I do. I decided on a deep pink matt. As I was finishing this application I noticed some movement in her crotch area. The silk of the négligé had changed reflection.

We were done...

I told Sasha to stay there while I chose her wardrobe.

Most but not all of the items I recognised, I had after all bought them for her.

I decided on a lightly stretchable mid calf length black wiggle dress with gold polka dots. It was a full length round collar neck with short sleeves. It required a thin gold belt.

Underneath I couldn't resist a 6 strap wide band garter belt with matching bra. Stockings were black glossy 15 denier. For a modicum of modesty I chose a pair of black satin bikini briefs with a floral print. From the collection of half a dozen wigs I selected a deep auburn bob. Shoes would be 4 inch open toe back strap heels. the jewellery was up to her. I hoped she had some clip on earrings.

I took the wig back to the bathroom and completed my part of making her presentable.

Having fitted the wig I brushed her hair for a couple of minutes and asked for a drink. Sasha said there was some sekt in the fridge.

We parted company while she dressed and I drank.

About 30 minutes later Sasha appeared looking gorgeous. Was I happy with the makeup....yes but not totally. I would have other opportunities.

I took both her hands and puller her in for a hug in the hope to relax her. I walked around her 360 degrees ton inspect. Not bad for a first effort but just one glaring mistake.

Her nylons were bunched around her ankles and a gentle lift of the hem of the dress revealed that the stockings only sat a couple of inches above the knee.

I instructed her to go and fix that. The garter belt should pull the nylon so they are lightly pinching at the skin I explained.

She came back with this remedied.

We sat and talked about the make up application. I wasn't good enough to give a running commentary as I applied her make up.

It was good that we had exchanged on zoom. Most of any initial awkwardness wasn't there.

We shared a glass of wine and a cigarette.

When sitting down on her sofa I scooched over closer so our thighs were touching. I put my arm around her and leaned in to give her a peck on her lips. She froze. Sasha was nervous but I could tell form the shape through her dress that she was also aroused.

I ever so gently grazed her bulge which only caused it to become more prominent.

The time had come for me to lead her through to her very tidy bedroom.

As I took her by one hand and our heels clip tapped on the hard floor, I felt my pulse race and my member swell.

Once in the bedroom I pulled her close and squeezed her but with both hands. We pecked lips. Sasha made to engage in an open kiss but I pulled back. I wanted to save her make up.

Like she was in a trance I lay her down on the bed on her back with her feet on the ground. She instinctively put her harms straight up over her head, resting them on the bed.

I sat on the bed and caressed her thighs, eventually moving up to her swollen groin.

Once she was fully hard I got down on my knees and lifted her dress up to her waist.

What greeted me was perfect. Her full member was pointing up and to the right straining against the black, floral panties.

I licked her shaft through the satin admiring the hardness of her.

When I decided that I must absolutely have this in my mouth I pulled her satin panties to the side to release her shaft.

I saw a 5 inch rock hard, arrow straight, cut cock standing perfectly vertically. Her balls were contracted to form one homogenous oval shape at the base of the cock.

I don't get in to sizes too much but this was slightly below average and with normal length/girth proportions.

I worked and sucked her shaft until Sasha had advanced about 80% towards orgasm.

I stood up and removed my skirt and shirt.

My own member was straining up and to the left against the glossy pantyhose and burgundy bodysuit.

Sasha sat up and did as I had done to her, kissing my member through the layers of synthetic material.

After a couple of minutes I unclasped the body suit to reveal my own 6 inch cut member shielded by the thin nylon that was now dotted with pre cum.

For Sasha I ripped the nylon to release my cock. She sucked rather hesitantly at first.

Just as she was getting the hang of it I gestured her on to the bed on her stomach.

With her dress still lifted around her waist I pulled her panties down to reveal her but plugged hole.

I wondered about this, had she remembered to insert one. I had forgotten to ask. I had asked about the enema though....all good.

After massaging her but for a while I removed her plug. I then reached for the bottle of lube I had eyed earlier.

I generously applied.

Eventually I worked my way in to her boy pussy with one finger. Then two.

When it was time to enter I rolled her on to her side.

My plan was to fuck her form the side so I could keep her calm with whispers and gentle kisses to her neck.

I lubed my own cock then applied a condom.

Penetration was not easy for Sasha, she was smarting.

I went slowly enjoying the perfume emanating from all of her.

I fucked her gently for about 5 minutes before I came.

As soon as I had caught my breath I removed my condom and started to work on her cock. She looked bewildered.

She needed to fuck me.

When fully hard and as vertical as she could be I put Sasha on her back.

This needed to happen quickly now.

Within about a minute I had lubed her cock, put on a condom and lubed that, removed my but plug and lubed my ass.

I then gently impaled myself on her enjoying the ease of her slightly below average girth.

But her hardness more than made up for it. This thing was rock solid!

Once fully entered and a few in and outs completed, I bent over to kiss Sasha passionately.

Lipstick was being smudged and smeared amid a wrestle of tongues, lips and groans.

She preferred it slowly so I rode her shaft for about 10 minutes before she came up my ass (protected by gossamer of course).

By the time she came I was about 90% aroused again.

While still impaled on her I rubbed myself to orgasm, dribbling just a few thick gobs of cum on her smooth belly.

That was enough for the first session.

Sasha's make up was adequate, her crossdressing was very good, she had lost her virginity and orgasmed once, I had orgasmed twice.

After some chit chat I spent 30 minutes in the bathroom getting myself in shape for the re entry in to male, publicly acceptable life.

Make up chair on Monday

The next evening was similar. I arrived at Sasha's and went straight to the bathroom to get ready.

Once my heavy makeup was on (again bright red lipstick) I chose to wear a pink satin and lace 6 strap suspender with 40 denier bronze stockings. Pink matching bra and panties also. I wore a mid calf length blush pink pleated skirt and a navy blue, long sleeve, collared chiffon shirt, buttoned up to the neck. I chose a chestnut mid length wig that I let flow. I slipped on some 4 inch navy velvet blue open toe heels. A pink ankle bracelet finished the ensemble.

I then walked through to the bedroom where Sasha was not.

She was in the living room having a skinny smoke and a glass of wine.

This time Sasha was fully dressed.

She wore black glossy 10 denier tights and a metallic grey, fitted mini skirt. On top she had a black, long sleeved cotton top that I only assumed was a bodysuit although I didn't recognise it. Her hair was a straight auburn bob.

Footwear consisted of 6 inch, diamond studded stilettos. She looked like a bit of a night club slut to be honest. I could see she she had put on a thin layer of foundation. Under the bodysuit her silicon breasts looked huge and delicious.

We chatted for 5 minutes and then went through to the bathroom. As per the previous evening we sat down and I did her makeup. It was quicker this time. She had already started and I was getting better.

When done I simultaneously reached under her skirt to caress her bulge and kiss her. When my hand reached its target she was 3/4 aroused, soon to be fully erect. We exchanged bright red lipstick. I was fucking horny....Sasha was starting to look real hot. As the chair was an office style chair it could be lowered quite a bit, which I did.

There was nothing left to do but remove my but plug and lift up her skirt. I unclasped her black bodysuit to reveal her throbbing cock.

I lubed up her and me then put a condom on her.

If we lowered the chair and Sasha slid down I could straddle her and have my feet on the floor

I then lifted my pleated and straddled her. Entry was a little painful without much prep but she was in.

So my thigh workout began with my pleated skirt covering entirely the business area....

Due to the position this would be a slow one.

On every up stroke my freed erection made itself noticeable through my skirt.

Much kissing and groping of Sasha's D-cup silicon breasts accompanied my riding action.

Her orgasm was long and drawn out, I slowed down even more when it was approaching.

I held her face to my ample bosom while she deposited her load in to the condom.

I was a little exhausted.

I sat back on the bathroom bench with my legs dangling to catch my breath.

After having realigned her outfit Sasha then scooted the chair forward and ducked her head under my skirt.

She worked my shaft until I was full hard again.

Having barely caught my breath and with tired legs Sasha led me through to the bedroom. She lay down on her front and lifter her mini skirt up to her waist.

She pulled down her nylons and panties to her mid thighs.

She removed her butt plug while I took off my skirt and lubed up. Condom on.

When ready I lay on top of her and eased myself in to her. Again not a lot of prep so it was not the easiest of entries.

Once fully in I pumped slowly and deeply a few times before Sasha starting lifting her hips slightly to meet my cock and clenched her butt cheeks around my member.

This way all I had to do was support my own body weight with my arms and Sasha could massage me to orgasm.

As my orgasm approached I took control and within a minute of of slamming my cock up Sasha's ass I released my spunk.

We lay down to catch our breaths and take stock. We were both looking rather dishevelled with torn nylons, crumpled clothing and smeared makeup.

We tidied ourselves up and sat on the couch for some snacks and a glass of wine.

We talked about her progress and where to go from here. Sasha had the next day off and wanted to practice her own makeup.

So when I arrived tomorrow evening Sasha would be made up and dressed. We decided on her clothes.

At any rate she was loving our lingerie fueled sex evenings.

Over the last couple of days more clothing packages arrived for Sasha. We opened and inspected these, salivated at the possibility of trying them on.

More to come.

Kitchen encounter on Tuesday

As agreed I arrived around 6pm with my suitcase of clothes and accessories.

The door was ajar and I went and prepared.

As a base I put on a cream short sleeve bodysuit with a built in bra and with a high collar.

I chose a white 6 strap suspender belt over the top of this and selected glossy, 10 denier stockings.

A pair of white, stretch capri pants would allow the lines of the suspenders to be clearly visible.

Footwear was a pair of 4 inch beige angle strap, open toe.

I went big on the wig. Blond, long and wavy.

Clip on hooped earrings added a bit of glam.

Once ready I went through to the lounge and then kitchen to see Sasha opening a bottle of Champagne.

She was wearing what we had discussed.......A white, floral print knee length mermaid dress with high collar and elbow length sleeves. Nylons were tan,10 denier and super glossy. Her wig was dirty blond short to mid length with straight bangs. White 6 inch heels.

After chatting for a bit I turned around to the kitchen bench to pour some more fizz.

Sasha came up behind me close and reached around to massage my crotch. As she did this she gently kissed my neck.

I stiffened to her stroking.

Before long the button of my capri pants was being undone. Next was the catches of my bodysuit.

Sasha pulled down my pants to mid thigh. Sasha parted my legs as far as the pants would allow using her knees against my inner thighs.

I kicked off my heels, I knew how this worked. I had to be lower than her to give her leverage

Sasha then removed my butt plug and then massaged my ass with lube and stroked my cock.

Sasha entered my ass with her protected cock.

What ensued was a very quick hot fuck. It only lasted about 3 or 4 minutes.

In fact it took about that long for her cock to go semi flaccid, at which point Sasha removed herself.

She stepped back and lent against the kitchen wall still catching her breath.

As I already felt slightly used and degraded I knelt down on my knees and removed her condom.

I then took Sasha semi-soft in to my mouth. I licked and cleaned her cock of her own cum making sure to get some on my lips.

Just as she was starting to stiffen again I stood up and kissed her gently on the lips.

She hesitated at first but became increasingly aroused at tasting her own juices.

We tidied ourselves up and moved through to the living room.

More Champagne and another cigarette while we talked.

I sat on he couch with my legs together but not crossed.

Sasha lay down with her head on the arm rest and nestled the heel of her foot in my groin.

Oh so gradually I hardened. Before long I had to adjust as my member was straining against my white pants.

I stood to remove my Capri pants. I had to take my heels off to do so but I made the effort to put them back on.

When I sat back down Sasha positioned herself on her knees on the floor in front of my hard cock that was now straining through the bodysuit.

I parted my legs and Sasha started gently kissing my inner thighs while caressing my outer thighs. She had a delicate touch.

She made her way slowly up to the base of my cock.

Her lipstick was long gone, smeared over my nylons.

She released the hooks of the bodysuit and gave me a nice long blowjob.

When we both knew it was time, Sasha lay on her tummy on my lap as if waiting for a spank.

Instead I pulled down her nylons and massaged her pussy with some lube by slipping my hand underneath her white satin panties.

When she was ready Sasha got up and knelt on the couch facing the back. This way I could fuck her by standing up and resting my knees against the edge of the couch.