Learning to Crossdress Pt. 02

Since relating my "First Experience" to you, I have been re-playing it over and over, in my head, and realise how fortunate I was to meet a lady who wanted to indulge her fetishes with me, and established my desire to crossdress.

As I left off, she had me wearing her silk panties, with her kneeling across me, my hands sliding up and down under her half slip and over her sheer nylons, with her just having covered my mouth in her thick, creamy lipstick and then taking off her bra and letting me kiss and suck her breasts, and super hard nipples so they were smeared with her lipstick.

She then asked if I enjoyed the taste of her favourite lipstick, and the feel of her silk panties, and satin bra and nylons.

To which I nodded and said "Oh Yes," I love the taste of your lipstick, and seeing it on your beautiful breasts.

Well she said I can tell you enjoy my silk panties with that nice bulge I can still feel.

It's so nice to find you share my fetish for very heavy lipstick and my nylon stockings and silky panties, so now I am going to put on heaps more layers of my deep red lipstick, and then cover them with this tube of shiny red lip gloss and take your virginity.

She then continued to kneel over me and started applying lipstick over her lips, then more and more on her bottom lip and smudging them together, and re-coating them with more and more layers.

I couldn't take my eyes off her, totally enthralled, as her lips seemed to be sticking together. How's that she asked, and picked up this little tube of red lip gloss and started squeezing this wonderful gooey shiny gloss all over them.

My heart was pounding as she said "are you ready" and took the waistband of her silk panties, I was wearing, and pulled it under my balls letting my rigid cock stand straight up. She then took a strong hold on the base of my cock and squeezed the rest of the tube of lip gloss onto my cock head.

She said "This is only the beginning, I'm now going to teach you how to please me."

She continued to keep a tight grip on the base of my cock, and with her other hand pulled up her half slip exposing her vagina, as I stared in awesome wonder at my first ever look at a totally shaved and bare pussy.

She then rubbed it up and down, inserted her finger, parted her pussy lips, then she then positioned the head of my cock between her lips and slowly started rubbing my cock head up and down between them, covering them with the lovely, slippery lip gloss she had covered me with, and then, positioned me inside them, eased me into her and slid down on me, until I was fully inside of her.

It was the most incredible feeling I had ever had, then she pulled me up so that she was sitting firmly on top of me, then pulled my hands around her body, wrapped her hands around me and pulled my head into her and my mouth on to hers.

It was like our lips were glued together, and she started kissing me hard and sucking and nibbling on my upper and lower lips, and covering me in her lipstick and gloss, then she stuck her tongue into my mouth and we were "French Kissing" which again was an amazing turn on.

The taste of her lipstick, lip gloss and saliva was absolutely overwhelming, and with her rocking back and forth on my cock, I just knew I would do anything this lady wanted of me.

She then rolled over so that I was now on top of her and said now "F***" me hard.

As she wrapped her nylon covered legs around my back and pulled me tighter into her, and kept kissing and sucking on my mouth, I was in "Seventh Heaven" and I didn't last too long before erupting inside of her.

My whole body went rigid and she said I had done well for "My first time", but she needed to keep me inside of her for a while longer, so she grabbed my buttocks which were still encased in her silky panties, and pulled me closer and said she was going to bring her legs together so I had to reposition mine at the sides of her nylon covered legs.

She was squeezing me with her vaginal muscles and told me to move up and down "gently" as even though I was semi - soft I still felt that I was deep inside her.

She then said, "Now my lovely boy I'm going to devour you."

She then pulled my head into her and started kissing me all over my face, and biting and kissing my neck, then back into another long lasting tongue tasting session with her lipstick and lip gloss flooding my mouth and taste sensations.

I knew then that I would do anything she wanted, and then realised that with her vaginal grip and control of my cock and our lovely back and forth rythym, I was starting to get hard again.

She then said, "I can feel you are getting aroused again, so know that you are now mine, to enjoy, and teach you how to please me as my lovely girl/boy."

The meaning of her words didn't register, but I remember that I just said to her that I would do anything she wanted.

She then said to go a little faster as she eased her cock grip a little, and pulled me closer, but still kept her legs together. She would then tighten her grip on me again and say slower now, then repeat the faster/slower routine, and even though I thought I was going to cum again, I was lasting through all this "Cock embrace."

She then fiercely grabbed my buttocks, digging her nails into me, and her body stiffened, and I felt this wonderful warmth encasing my cock, which I didn't realise was her cumming.

She started moaning but continued with our fast/slow rythym for a lot longer, and I felt the wonderful warmth of her cumming, flooding my cock, several more times, before we both arched in unison and came together.

I was now holding her so tight, our lips locked, and she was still digging her nails into my butt, and my head was spinning.

We finally both relaxed and she said now we were going to lie and cuddle, and she was going to give me "Booby Cuddles", so we lay on our side and she moved my head between her gorgeous breasts, but also gripped my semi-soft cock between her nylon covered legs, and as we wrapped our arms around one another, she planted a kiss on my forehead, and said that she was really happy to find her own girl/boy who "like her" loved nylons, silk panties, satin, and heavy lipstick, and that after we rested a little she had many more wonderful things to share with me.

Again, her "girl/boy" words didn't register anything with me, but I just looked up at her and said that I thought she was the most beautiful and amazing lady I had ever met, and, as I ran my hand up and down her nylon covered legs, and felt them squeezing my cock, said that I loved everything about wearing her silk panties, the touch and feel of her nylons, her lovely satin bra and slip, and especially kissing and tasting her heavy, creamy lipstick and gloss, and that I would do anything she asked. Especially if we could do everything all over again.

She pulled my head back between her breasts and said that I had really pleased her and that we would "definitely do everything, and more, over and over again."

She said she wanted me to stay overnight with her, but for now, just to lie and cuddle.

I lay between her breasts, stroking her nylons, and was re-playing in my mind all the exquisite pleasures she had just introduced me to, and thinking how lucky I was to have had this beautiful lady give me my first sexual experience.

After an hour or so of cuddling, she said let's go shower, clean ourselves up, get dressed, and have a something to eat, so I can get my energy back, and then I would be ready for her to teach me more of her pleasures, as I was no longer a virgin.

The rest of that evening filled me with this desire ever since then to cross dress.

But I will explain what and how, if you want me to recall more.

(How can I possibly forget).