Learning to Crossdress Pt. 03

I had just had the most amazing first time sexual experience, with the most beautiful erotic lady, I could have ever have imagined, who would introduce me to silk, satin, nylons, and then cover me in lipstick and lip gloss and have me cover her breasts in more and more lipstick kisses before losing my virginity.

We had been "relaxing" together for about an hour now, with my head between her breasts and my cock, after coming out of her, being held between her nylon covered legs.

Our faces and bodies were covered in lipstick, so she said we needed to shower and clean up before our "Next Session".

As we moved to get up my cock which had been covered in our juices, and her lip gloss, was stuck to her nylons and she laughed as she took hold of it and peeled her nylons away.

I stood and she slid off the silk panties I was still wearing, and she slid down her half slip and stepped out of her 4" high heels, she had kept on the whole time. She then unfastened the clips of her garter belt from her nylons, and held up each leg for me to slide off her nylons, then unhooked her garter belt, and placed everything on the padded bench, at the foot of the bed.

We then looked in the mirror and laughed at how much lipstick we were covered in, all the lipstick I had left on her breasts was also smeared all over my chest, and my face was absolutely covered.

We stepped into the shower, and she took a large fluffy sponge and started cleaning off all my lipstick, and then gave it to me to do the same for her. To be with this beautiful lady, in the nude, and washing her body all over was breath taking, and as I said earlier, I knew I would do anything she asked of me.

We got out of the shower and dried one another, then she took a couple of silky bathrobes from behind the en-suite door, and said "one each for us to wear" but before we go downstairs we need to put on our panties, so we went back into the bedroom, and she opened one of the drawers on her dresser and took out 2 pairs of black silky panties and gave one pair to me and said slip into these while I slip into mine.

I had no hesitation about putting them on, and we then put on our robes but before we went down to the kitchen she applied another liberal amount of lipstick.

She reminded me that I was to stay overnight.

So, as I still lived at home, I made a call saying I had met a friend in town and would be staying at his house till Sunday afternoon.

When I hung up the phone, she came over and gave me a huge hug and kiss, which felt so soft and warm.

I just moaned and returned her kiss and then was "brave enough" to part her robe and kiss her beautiful nipple.

She gave me another kiss and said I was a "good learner, recognizing the things she enjoyed" and now had to kiss her other breast, to keep everything equal.

She then prepared a meal, and I offered to help wherever I could, as I just wanted to be beside her as much as possible.

When she had put it on to slowly cook, she said let's sit down on the couch again and have a nice chat with a glass of wine.

I said I wasn't used to drinking wine, but I would love to have a glass with her.

So with our wine in hand we sat down to chat, and I recall her telling me she had been a widow for a couple of years now, and that she tended to keep to herself, at home.

When she did go out shopping, she said she always liked to "Dress very fashionably" and wear lots of makeup and lipstick, and didn't care initially about the stares and nasty comments she heard from strangers.

She loved going to the fashion and lingerie store and buying her favourite fully fashioned nylons, and silky sexy lingerie, and the latest colours of lipstick, and always fantasised about sharing them with someone, as her late husband would not kiss her if she was wearing lipstick.

She said she hadn't been with anyone since her husband passed, and although she had "Teased" a few men, she had always "Backed Away" when they responded to her advances, because she found them to be overly aggressive and not really listening to what she wanted.

She said that she had also spent an afternoon with another woman, and while she loved sharing lipstick kisses with her, and feeling their nylons next to each other, it didn't progress the way she wanted, nor imagined.

However, with me she knew I was totally infatuated with her and she wanted to see how far she could "Lead me" and turn me into her girl/boy.

She said she was delighted, and excited, when she was able to get me to caress her nylon covered legs, and when she put my hand on her breast and I said I would love to taste her lipstick, she just had to take me to the next step.

When I put up no resistance to putting on her silk panties she felt sure she could follow through and have me do whatever she asked.

Also, knowing that it was going to be my first time was doubly exciting for her, and she wanted to prolong it for as long as she could.

Now that we had had our first mutual sexual experience she wanted to extend the rest of my "transformation," to have me as her personal young girl/boy.

I said then that I really didn't understand what she meant, but that I would do whatever she wanted just to be with her.

She said "Thank You," that pleased her completely, and that she knew I would enjoy everything we were going to experience, and that I would totally discover the exquisite feeling of wearing nylon, silk, and satin, and her creamy lipstick.

She then said that after dinner, she was going to dress me "As her beautiful Girl", and along with my silky panties, she would select a lovely corset, and bra, pick out a lovely pair of her seamed nylons to attach to the garter straps of the corset, and also have me try on a pair of her open toed high heel sandals.

She would be dressed almost identically, and then we would sit at her make up dresser and she would do mine the same as hers, with eye shadow and lots of lipstick, and a covering of lip gloss.

I was turning as red as a beet, but said, if that's what she wanted I would be really happy to let her dress me.

She cupped my face in her hands, gave me the softest, sweetest kiss and said that since we showed up a couple of weeks ago to paint her house, she noticed me immediately and the way I always looked lustfully at her, and had been thinking about how wonderful it would be to have me with her like this.

She had dreamed about having me dressed in her nylons and lingerie, lying next to her, with our nylon covered legs sliding against one another, our silky panties together, and our fully lipsticked mouths being locked together, as I became her "Personally Groomed Girl" but with a difference, in that whenever she wanted she could slide down my panties over my "Boy Part" and have her "Girl/Boy" inside of her, and hold me there for as long as she could, until she was ready to let me go, "Just like earlier."

We continued to enjoy our glass of wine, and we sat at the table and had our meal, put the dishes in the dishwasher and then she took me by the hand and said "Now my beautiful young boy, it's time for me to transform you into my beautiful young girl."

We went back into her bedroom and I had a hard on already in anticipation of what was about to happen.

She led me to her dresser and opened a wide drawer which had 4 rows of corsets and bustiers, each row at least 4-5 deep, of all different colours, and next to that, 2 rows of neatly folded matching bras and panties, with 4 in each row and again 4-5 deep.

My mouth hung open looking at such an array of the sexiest range of lingerie I could have imagined.

She then took out a beautiful black satin corset and what (I was to learn) was a waist cincher. (I was soon to learn what all these amazing, beautiful, sexy items of lingerie were called, as she would later model the different styles for me to admire, and select which I would want her to wear.)

Then she stepped into and pulled up her corset, until the bra cups fit around her beautiful breasts, and asked me to do up the open clips in the back, saying she normally had to do it up in front and pull it around then try and squeeze herself into it.

She then put her arms through each shoulder strap and pulled them up and adjusted her fantastic breasts into each cup. They were spilling over the top of the underwire bra cups, had a lovely satin fringe on top, and pulled together in a mouth watering cleavage.

Seeing her breasts supported and pushing out of her bra cups like that was breath taking, she was so fantastic looking.

She saw me staring at her breasts and said "you like these, don't you" and I said how much I enjoyed cuddling and kissing them, and just lying with my face between them.

She said there will be lots more of that to come, but for now "Let's look at you."

She told me to turn around and brought the waist cincher in front of me and clipped it behind my back, with the ten little catches.

I turned around and looked in her mirror at how my waist had been pulled in and I had these straps hanging down the front of my panties, 2 in the front, one on the side, and one in the back, of each leg.

She went back to her drawer and took out a black satin and lacy, long line, bra, that definitely would not have fit her, and had me put my arms through the shoulder straps as she then fastened it behind my back.

She smoothed it around the top of the waist cincher and then adjusted the side of my chest and inserted a soft, rubbery pad inside each bra cup which pushed my breasts "Up and together."

I couldn't believe it as I looked down, I actually had a cleavage. She told me that she had purposely bought this bra, during the week, hoping and anticipating that she would create the opportunity for me to be here with her, as she told me there was no way my "Lovely little breasts" would fit into one of her own corset or bustier bra cups.

She then opened another drawer, which was neatly stacked with dozens of pairs of nylons, still in their packages, and took out 2 black, fully fashioned, seamed pairs.

She had me sit on the edge of the bed, took out and unfolded a pair from the package, ran them across my face, then rolled up one of the nylons and slid it over my toes and then pulled it slowly, ever so slowly, all the way up my leg, little by little, making sure I was enjoying the experience. She then asked me to stand and turn around so she could make sure the seam was straight, then she attached each of the garter clips, to the lovely dark tops. Then repeated the process with the other leg, it was such a fantastic feeling and I loved the sensation.

I started running my hand up and down the nylons and she asked if I liked how they felt on my own legs, to which I said the feeling was incredible, and I loved it.

She smiled and took her pair of nylons, and said "Watch Closely" how I put mine on, so you will be able to do it yourself in future.

I just sat there in admiration, and lust, as I ran my hand up and down my own pair of nylons and watched this beautiful lady put on her nylons, check the seams were straight, and attach them to the garters of her corset, which she had pulled beneath her panties before clipping them to her nylons.

She then said to come into her walk-in closet, and look at her shoe rack and see if we could find a pair that would fit me.

She picked out a pair of 5" pumps and said, these would be for her, and put her hand on my shoulder as she stepped into them and now seemed to be towering over me, but she looked so amazing, in her heels with her long statuesque legs, in her black seamed nylons, and the sexiest of corsets, with "Ribs" running up her front and sides and highlighting her amazing breasts, I think I was drooling.

Then reaching to a top shelf, she pulled out a pair of 4", open toed, strappy sandals, and said we better have you sit on the side of the bed while I see if these will fit you.

So back we went and she kneeled in front of me and slid my foot into the open toe, and then pulled the strap behind my heel and buckled it around my ankle. It felt tight, but my foot seemed to fit into it, so she put on the second one, and then took my hand to stand up.

I wobbled somewhat trying to balance on them, but she said to take her hand and we walked around her bedroom as I became somewhat accustomed to the newest sensation of wearing high heels. Probably because I was rather fit, I seemed to "Master" it quickly and let go of her hand and "Strutted" out on my own.

Again, I was admiring myself in her mirror, and she was saying she was so happy that I was enjoying it so much, as now with the "Finishing touches" she would have created "Her Own personal, beautiful Girl/Boy."

She told me to now go and sit on the bench in front of her make up table, and she sat beside me.

She first took out a foundation and covered my face in it. I looked sort of a "Light tan" all over with no defined features. She then did exactly to same to herself, followed by a soft fluffy brushing of a rouge on our cheeks to highlight them.

She then used a pencil to highlight her eyebrows and next took out different shades of blue eye shadow and told me to watch as she coloured her eyelids with different shades, then applied a black eye liner, and finally she attached these long eyelashes.

Again, she went through the same process with my eyes, and when she was finished, I "Fluttered" my new eyelashes up and down, as she smiled.

Now it was time for our lips. She took this bright red pencil lip liner, and outlined her lips once, twice, three times, until she was satisfied she had the perfect definition, and of course, she did exactly the same to mine, as I again just sat there trying not to cum in my panties.

Then she picked up 3 different tubes of lipstick, and opened each, slowly turning up the delicious stem of colour in each one, and said this is where she always found it hard to decide which one to pick. She asked me if I had a preference, and I pointed to the deepest, brightest red, and she said I had good taste as that was her favourite.

She then coated my lips in this luxurious, creamy, red lipstick, going over and over until it felt quite heavy, and sticky, on my lips, telling me to "Smudge" them together and then re-applying another layer.

When she was satisfied I was wearing enough she spent the next 5 minutes coating and re-coating her lips, as I just watched in admiration while running my hands up and down my nylons and over my lovely satin bra, feeling my own breasts.

She then told me to just sit for a minute and went back into her closet and came out with a brunette, bob wig, and fitted it over my head, which came half-way down my forehead and curled up under my chin on each side, as I now went into stunned silence.

She said we should now stand and admire ourselves in the mirror, as we both look stunning, and as I looked I had to agree.

I couldn't believe the reflexion was me.

Standing beside this beautiful lady, who had the most perfect long legs, toned body and mouth watering breasts, was a very hot and sexy looking young girl, dressed in high heels, with the same black seamed stockings and garters, her large, and my small breasts standing proudly in my black satin and lace underwire bra, and both of us with blue shades of eye shadow, long eyelashes, and the heaviest, deepest red creamy lipstick. Me with lovely brunette bob hair style, and her same colour hair in her usual tied back bun.

I turned to her and said that I looked and felt fantastic and that if this is how she wanted me to look as her "girl/boy," she could dress me anytime as I couldn't believe how much I loved being dressed in her high heels, stockings, silk panties, bra, and being made-up to look as stunning as her, and I loved the feel and taste of her lipstick, and with wearing the wig I certainly looked and felt like "Her Girl," and I so wanted to make her happy, and would do whatever she asked.

She said that made her very happy, and she was hoping I would feel that way, as she had been dreaming about it for the past week, after seeing how much I was infatuated with her, and was now eagerly anticipating our upcoming sexual session, when she would introduce me to some new pleasures.

I said I couldn't imagine anything feeling better than being next to her dressed the way both of us looked, and feeling my nylons sliding against hers, with our silk and satin, and sharing our lipstick with each other before I hoped to be inside her again.

She said, you know all of that is going to happen, but first I want to you to put on the skirt and blouse, I was wearing today, so I can see how you look, in an outfit I wear when I'm ready to go out.

So I buttoned up her blouse and slipped on her skirt, which she zipped up behind me, and she then told me to walk back and forth across the room. She said that since I had commented how great she looked when she walked past in her heels, seamed stockings and short skirt, she now appreciated how it would be a "Turn On" for boys, as she thought I looked great.

Now she said, she needed to put on a skirt and top and we would go back downstairs and relax on the couch with another glass of wine, so we "Girls" could get to know one another better, and she would teach me how to walk and sit as a "Proper" girl should.

She selected a short leather skirt, that hugged her hips and came half way up her thighs showing a good part of the dark top of her nylons. She selected a top and slipped it over her head and pulled it down over her glorious breasts. it was a silky, semi-transparent material through which her corset and ample cleavage were definitely on show.

We went downstairs, and she taught me to walk in my heels by placing one foot directly in front of the other, as this gave a feminine sway to my hips, so with a couple of practices she was satisfied with my composure.

She then instructed me that when I sat on the chair, I had to make sure my knees were together, and then to sit with one knee crossed over the other, because this revealed more of my nylon covered thighs, which attracted lovely looks.

She then asked me to join her on the couch, and with both of us sitting with our knees crossed, she snuggled up so close to me and started rubbing her hand up and down my nylons, saying how much she enjoyed the sheer feel and touch of them, and asked me to caress hers "Just like before," so both of us were running our hands over each other's nylons and I was reveling in every sensation.

She then took my hand and put it on her breast, again like before, and then she started fondling my breast and said "This is where I wanted you to be with me, as my beautiful girl/boy," she then put her other arm around the back of my neck and pulled me into a gentle, sensuous, lip lock, and we shared our lipstick, with our tongues in and out of each other, then she pulled me in hard and really started engulfing my mouth.

I responded equally as fervent, and while I kept squeezing and fondling her breast, my hand went back to caressing her nylons, up and down, and under her mini skirt and between her legs to where I was stroking against her panties.

She said, that feels so nice, and I want to let you know that a woman has "Two sets of lips," the first you have been kissing all night, but I now want to teach you how to kiss, and suck, and lick my more sensitive lips and cover them with your lipstick, and please me with your tongue.

Afterwards, I will wrap my lips around your "boy part" and suck and cover you with my lipstick, before we get on the bed, and I hold you tightly, inside me and we lock our lips together and I "Fxxx" you again.

So now my beautiful girl, let me take you back upstairs, and we will get ready for the rest of the night.

Again, I need to take a breather before my next episode.