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.