Learning to Crossdress

I was now totally dressed, in 4" open toed sandals, with black seamed fully fashioned stockings attached to the garters of a tight fitting waist cincher, wearing an underwire long-line support bra with "Pad inserts" that pushed to give me a cleavage.

My makeup was incredible, with blue eye shadow, long eyelashes, and heaps of lipstick, and I was wearing a brunette bob style wig. I was also wearing her skirt and blouse which she had been wearing earlier in the day.

The beautiful lady who had dressed me like this was more stunning than ever in her heels, stockings, short skirt and see-through top, with her usual outstanding makeup and heavy lipstick.

She had just given me lessons on how "A Girl" should walk in her heels, and how to sit properly in her short skirt, and followed that with both of us together on the sofa, caressing each other's nylons and sharing our lipstick, of course.

Now it was time to go back to the bedroom.

When we got upstairs, she told me to take off her top, and she undid my blouse, then to take off her skirt, as she did the same for me. Then it was her panties, which I slid down her legs and over her black 5" pumps.

She then sat on the edge of the bed, parted her beautiful nylon covered legs, and told me to kneel between them.

As she then parted her pussy lips, she said that these were the second and "more sensitive" lips that every woman had and she wanted me to learn to kiss and enjoy them, but also telling me that the little bud between them was the most sensitive, and she wanted me to lick and suck on it, and then to put my tongue in as far as I could between her lips and lick the insides.

I said I would do whatever she wanted, so I positioned my head between her legs and started to kiss her and cover her lips with my lipstick.

Then I found "her bud" and wrapped my lips around it and began to pull and suck on it, and twirl my tongue around it, and stick my tongue between her lips.

The taste was unnerving at first, and I wasn't sure I wanted to continue, but I had agreed to do whatever she asked, so I kept going and started getting used to the taste and didn't really mind it.

I then felt her pulling my head closer into her, as she put her legs over my shoulders, and I instinctively started licking and pushing my tongue in as far as I could, I was running my hands over her nylon covered thighs and trying to please her as much as I could by licking and sucking as feverishly as I could.

She lay back on the bed and it sounded like she was moaning.

She continued to pull my mouth deeper into her and her moans got louder, and suddenly she sat up saying "we need to stop for now" and that I had done really well for my first lesson in oral sex and that she didn't want to cum in this session as she wanted me back inside her again before we each had our next climax.

She relaxed her hold on my head, and the squeezing of her nylons against the side of my face, and said that when she got her breath back it would be my turn to experience oral sex.

She relaxed back on the bed, and as I started to move back, for whatever reason, as I felt her nylons against my cheeks, I started kissing her left inner thigh and running my tongue along her nylons, and just sliding my cheek along them. She rubbed her hand over the back of my lovely bob wig and said she was really enjoying her legs being licked and kissed and to please not stop.

I lifted her leg and continued kissing and licking down her nylons, slowing for a bit behind her knee, then running my tongue down her seam and kissing my way back up her calf.

When I got back to her ankle, I slipped off her pump, and licked and kissed her insole then over and over the dark shaded heel of her fully fashioned nylons.

I moved to her toes and was sticking my tongue between them through the dark toe piece, then I took her toes in my mouth and sucked each of them before taking as much into my mouth, as I could.

This was something I had always dreamed of, to be kissing beautiful nylon covered legs like this and filling my mouth with her nylon covered foot, so I was in my own fantasy land, just experiencing this.

I reached over and slipped off her other pump, and held her foot against my face, while I was still sucking on her toes of her left foot, then switched to have her right toes in my mouth, and then was running both her nylon feet all over my face.

She said that she enjoyed having her toes sucked immensely, and she could see that I really had a fetish for her nylons, that she would share with me anytime I wanted.

I told her that ever since she first walked past and I saw her wonderful seamed nylons, I fantasised how wonderful it would be to kiss her nylons all the way up her seams.

She replied that I was welcome to indulge my fantasy anytime, however, I needed to put her pumps back on her feet and stand between her legs, as it was her turn to please me.

She picked up her lipstick and did her usual heavy coating, as I stood there she reached under my waist cincher and pulled down the waistband of my panties under my balls, my raging hard on just stood out inches from her mouth.

Next she gave the base of my cock a firm squeeze, and put her lips to my cock head, leaving a lovely bright red lip imprint.

She pulled back and looked at my glazed eyes and then slid her luscious lips down over my cock and pulled back again, leaving another beautiful red ring around it, for me to enjoy.

Then she started sliding up and down my cock taking me deeper and deeper while still squeezing the base.

I was reeling with dizziness when she pulled back and said it was now time for us to get comfortable on the bed as she needed me back inside her, but first we had to "Freshen" our lipstick.

She re-applied hers, heavily as usual, then gave me the tube of luscious, creamy, red lipstick and told me to do mine, as her beautiful girl/boy should be able to apply her own lipstick.

I put on coat after coat as she lay back on the bed and then I knelt between her legs and slid my hands all the way up her nylons and over her satin corset, moving slowly and relishing the feel of her magnificent lingerie, and fondling her beautiful breasts.

She took hold of my cock again and positioned it against her pussy lips and wrapped her legs around my buttocks and pulled me closer.

I had my hands behind her shoulders and leaned into her and we started kissing so tenderly, and as our creamy lips seemed to be sticking together, I slid fully into her and felt the warmth of her wonderful vagina as she started squeezing me with the amazing control she had of her muscles.

She then broke our kiss and said she needed to close her legs "like before" as gripping me tight inside her was a favourite sensation for her as we moved together.

Our hips were together and our nylons were sliding over one another as I moved back and forth, with my breasts on hers, and then our fully coated lipsticked mouths were together again.

The feel of our nylons against one another, and of my "breasts" in my bra against her corseted breasts as we kissed was pure exstacy, and as I moved back and forth I could feel the pull of my garters on my nylons, which just increased the sensation of being so wonderfully dressed and having sex with this amazing lady.

We kept up our lovely motion, as her vaginal muscles kept tightening and easing their grip on my cock, until she dug her nails into my buttocks, pulled our bodies even closer together and we both came together.

We just rolled onto our sides and continued to cuddle and kiss, as she kept hold of me inside her.

We were starting to "Doze Off" and she said I should pull up my panties, and put my wig at the bedside table, and we should both take off our heels and get under the covers and try to get some sleep.

We did eventually fall asleep, with our arms around one another, after lots mote cuddling and kissing.

When I awoke in the morning, I looked at this beautiful lady, on the pillow beside me, and looked at how I was dressed, and thought about what a magical day, evening, and night, I had just experienced, and wondered what I could possibly do to thank her for my "Transformation" and teaching me how she liked to be pleased.

I looked at her, still asleep, and moved under the covers and parted her nylon covered legs, and started kissing and licking her pussy lips.

I knew she liked "Her Bud" to be sucked, so I concentrated on that and pushed my tongue deeper between her pussy lips.

She let out a "Little Squeal" and gripped the back of my head and really pulled me into her, so I just tried to increase the tempo of my licking and insert my tongue as far as I could.

She was moaning, and getting louder, then another squeal, and she thrust her hips up and started "Bucking" against my face.

All of a sudden, this warm gush of her cum came flooding into my mouth, and she was holding me so tight that I had no option but to swallow.

My first reaction was one of "Being Scared", as I was trying to back away, but her grip wouldn't let me, so I tried to relax and just kept taking in the next several floods of her cum.

When she had stopped climaxing, she pulled me up to her and covered my mouth with hers and was tasting her own juices.

She told me that was the most wonderful way she had ever been awakened, and that she was going to have me keep visiting her for sleep overs, on weekends, or anytime I wanted to visit her.

I said that if she would always dress me as her girl/boy, I would love to visit her as often as I could.

She said that she had absolutely adored transforming me into her "Beautiful Girl" and that she would be shopping for some really sexy corsets that would fit me, so that I could have a selection of lingerie to wear.

We just lay there talking, cuddling and kissing, while running our hands all over one another,for the rest of the morning.

Over the rest of that summer, I visited her nearly every weekend.

When I started university my visits became less frequent, but still continued on a semi-regular basis.

Ever since then I have definitely had a fetish for cross dressing, and wearing nylons or pantyhose, but always with high heels and a couple of gorgeous corsets that she let me have to take with me, as well as a few tubes of "Her Favourite" creamy, red, gorgeous lipstick.

I'm married now, but am what is referred to as a "Closet Cross Dresser." I have collected my "Stash" for dressing whenever I have the chance.

In reflection, I have re-lived my first weekend with my beautiful "Tutor" over and over.

I will never forget it, and it would be wonderful to have my "First Time" sensations all over again, but the memory will never fade.