Learning to Crossdress

I am a "Closet-Crossdresser" - something my wife would not accept, but a secret I indulge in whenever she is out of the house for a while.

This is my story of how a beautiful older lady, who had a "fetish" for lipstick, nylons, high heels, and lingerie, introduced me to the pleasures.

It was the late-1980's, we had just moved from a small town in the UK, to a large city, in Canada. I had recently turned 18, was 6 foot tall, athletic build, as I did a lot of running and played rugby.

My cousin had his own painting company, and took me on as a "Helper", during the summer months. We spent a couple of weeks doing the outside of this lady's house, and every time she went in or out, I couldn't help but stare at her.

She was probably in her 40's, about 5'7" tall, always dressed immaculately wearing a short, fairly tight skirt a few inches above her knees, which emphasised her buttocks, and a silk blouse, tucked into the waistband of her skirt, that highlighted her huge breasts, and she always wore 4" heels and nylon stockings with that "Fantastic" seam up the back. Her hair was usually tied back in a bun, but she always had very dark eye shadow, and very heavy red and glossy lipstick.

When she walked past she would always stop for an instant and ask how I was doing, and probably enjoyed my embarrassment when speaking to her, and always "Looked Back" to see me staring at her lovely seamed nylons as she walked away.

We finished all the painting on a Friday, and my cousin asked me if I would go back to her place on Saturday and clean all the windows, as he believed in leaving everything spotless.

I of course said "no problem," and that I would go over Saturday morning. As it was a hot summer's day, I just wore my shorts and T-shirt and runners, as I was only going to be doing windows, so didn't need the painting overalls.

When I was almost finished, she came out looking as stunning as usual, and asked if I would like a glass of water.

To which I said that would be very nice after I finished, as I only had 2 more windows to do.

She said great, when you are done come on in and relax and we can have a chat, and I'll get your water.

I knocked on the door, a short time later.

She called to "Come In."

So I took off my runners as was the custom in going into anyone's house. She was standing in the kitchen, and I asked if I could wash my hands first, and she showed me the guest toilet and said to come into the Family Room afterwards.

When I went in she was sitting on the edge of the sofa and pointed to a chair opposite where she had placed my glass of water, and said to make myself comfortable.

As I took a sip she thanked me for cleaning up, and started asking all sorts of questions about, where I was from previously, how long I had been here, what were my plans for school, etc., and then asked if I had a girlfriend.

I said I did have before, but had not met anyone since moving here.

She said "Well that probably explains why you stare at me a lot."

I was really embarrassed and answered that "I was really sorry, if I was being rude."

She said "Not at all, actually she found it quite flattering, and asked what it was that I found so attracting about her?"

I replied that she was very beautiful, and always looked amazing.

She then asked what it was that I found so appealing.

I blushed, and was sort of choking on my words.

But she said don't worry, I really want to hear what a young man like you finds attractive about "An Older" lady.

I said, well first it's the way you do your make up, your eyes are always perfectly done and your lipstick is so full and red and glossy, and looks amazing, that I can't help but gaze at you whenever you pass.

She said, well "Thank You," I take time every day to do my make up before going anywhere and I love to wear lots of heavy, creamy lipstick, as it feels so lovely on my lips.

She then asked if my previous girlfriend wore lipstick.

To which I said "No she didn't."

She replied "What a Pity."

Now she said, what else do you like about me as you are always looking at me when I'm walking past.

I again blushed, and said I loved the way she wore her short skirt, showing off her legs with her lovely seamed stockings and high heel shoes.

She said thank you again and that she loved to wear her "Fully Fashioned" nylons as they accentuate a woman's legs, and that she loved the way they felt against her skin.

She was sitting with her legs crossed and was running her hand up and down her beautiful nylon covered leg.

She then startled me by asking if I enjoyed the feel of nylons.

To which I gulped that I had never had the experience.

She then said, well come and sit over here beside me on the sofa.

She then re-crossed her legs with her right leg over her left, causing her skirt to move up a bit and show the dark top of her nylons, my heart was pounding as she said "Now sit close to me," then took my left hand and put it on her knee and guided it up and down her leg.

She asked if I liked how it felt.

I said it was absolutely wonderful.

To which she replied that she was glad I liked it and to keep running my hand all the way up and down as she really enjoyed her legs being caressed.

After a while she held my hand on her thigh, and uncrossed her legs moving her left leg over so that my left hand was "Pinned" on her right thigh with her left leg on top of it.

She then said now use your other hand and run it up and down my left leg.

I was in "Seventh heaven" and couldn't believe this was happening.

She just smiled and asked if I was enjoying the feel of her nylons, and said that she absolutely loved the feel of nylon, silk and satin against her skin, as it felt so exquisite, and she always wore all three every day.

She then looked me in the eye and asked if I would like to share with her, the feeling of all three nylon, silk and satin against my skin.

I said that would be incredible, not really understanding what she had in mind.

She then took my hand and placed it on her breast, and I let out a gasp. Then she cupped my face in both her hands and leaned into me, I was trembling and could smell her lipstick as she was almost "Nose to nose" with me, and she asked if I would also like to taste her lipstick?

I was hypnotised and said that I would love that.

So she said well first I had to promise her that I would do exactly as she asked "No Questions," and she would introduce me to all these wonderful sensations.

I said "I promise."

She then took my hand and said "Come with me" and led me into her bedroom.

She said "We are now going to play a little game, where I will remove a piece of your clothing and you then have to remove a similar piece of mine," and you have to follow everything I say.

We were standing at the side of her bed, which had the covers turned down, and pillows "propped up" against the headboard.

With her right in front of me, pretty much eye to eye in her 4" heels, my head was spinning thinking of what was going to happen.

She then lifted up and took off my T-Shirt and dropped it on a padded bench at the foot of her bed and said "Now I want you to take off my blouse."

My hands were shaking as she guided them to unbutton it, and pull it out from the waistband of her skirt, and as I slipped it down her arms I gasped at her voluptuous breasts which were cupped in a shiny black fabric, with lace trim, and bulging out over the top of her bra cups. I likewise placed it on the bench.

I couldn't believe what was happening as I had never seen anything so beautiful other than in magazines.

She then took my hands and held them to her breasts and said this is what satin feels like. Did I like it?

I just stood there fondling her amazing breasts and repeating over and over "Yes, yes, yes."

She then loosened the tie on my shorts and let them fall to the ground and told me to "Step out of them, and unzip her skirt."

She turned with her back to me so I could reach the zipper on her skirt, and as I unzipped it and slid it down her legs, she turned to face me.

She was wearing a black "Half-Slip" that came just to the top of her nylons, and did a quick turn and asked what I thought.

She was stunning in her 4" heels, black seamed nylons with the dark tops now fully showing, her half slip, and sexy satin bra, with her amazing eyes and heavy, creamy lipstick.

Even in magazines and movies I had never thought anyone could look as beautiful and breath taking as she did to me right then.

I said that she was absolutely beautiful.

She then took hold of the waistband of my underwear and slid then down my legs, so that I was now completely nude in front of her, with a raging hard on.

Now you have to take off my panties she said, and guided my hands up her hips, beneath her slip, and helped me to slide them down her nylon covered legs.

She stepped out of them and then my next "Shock" came when she said "You have nothing more for me to take off, so I want you to put on my silk panties."

I looked in disbelief, and she said "Now remember your promise to me," so I slid them up my legs and the sensation when I pulled them over my cock was unbelievable that I thought I was going to cum on the spot.

She said, "Well this is your first introduction to silk, the rest is soon to come, so I want you to lie back on my bed, and I'll prop up the pillows so you can lie back and be comfortable."

She then got on to the bed, kneeled across my thighs, just in front of my silk covered cock, with her nylon covered legs on each side of my hips, and told me to relax and keep sliding my hands up and down her nylons while she let me experience the exquisite feel of satin.

She leaned forward and started sliding her beautiful satin covered breasts back and forth across my face, and then put her hands behind my head and pulled my face between her breasts saying "First my nylons, then my silk panties, and now you get to enjoy the feel of satin, and of my warm breasts."

I was starting to get less tense, and take in all these wonderful sensations, but still not really understanding what she was leading me through.

She then said, it's now time to let you taste my lipstick, and sat back and reached for a tube of lipstick on the bedside table.

I watched transfixed as she popped the top off, and a beautiful dark red stem emerged, which she coated liberally on her already heavy made up lips, from side to side, over and over.

Then she leaned into me, squeezed my lips on either side so that my mouth opened, and then her mouth came down on mine and our lips literally stuck together as she sucked on my mouth. The slippery, sticky feeling and taste of her lipstick and saliva was so intense, that my precum was oozing into her silk panties.

She then broke away and our lips seemed to part with a pop. She smiled and said "Wow you have taken off nearly all of my lipstick, and I want you to give it back."

She then slipped the shoulder straps off her satin bra and unhooked it, fully exposing her breasts and said "I now want you to kiss and suck my breasts so that they are covered in my lipstick."

"We'll start with the left, then I will redo my lipstick and you will repeat the process on my right breast."

She then leaned into me, told me to open my mouth and held her beautiful breast and guided it into my mouth. I sucked, and kissed and licked for what seemed like an eternity, when she pulled back and said "Let's see," - "Yes, I think you have returned enough, so let's get started on the other." She again picked up her lipstick and started re-applying, layer after layer.

Then it was my turn "In Paradise" again, kissing, licking and sucking on her right breast. I couldn't believe how big and hard her nipples became, almost filling my mouth on their own.

I was on the verge of exploding, when she reached down inside my panties and squeezed my cock, that sent a surge of pain through me, but definitely quelled the urge to blow my load.

She said "We will take care of that shortly, but for now I'm not done putting on more lipstick, and also lip gloss, because when we have our next kissing session I will take your virginity."

If you want to hear more, I'll post the next chapter soon.