Adventures of Alice and Alex Pt. 04

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Alex's Introduction to Cross Dressing.
1.5k words
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Part 4 of the 5 part series

Updated 06/08/2023
Created 11/23/2016
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Alex wears lingerie again, and Alice hears of his first cross-dressing experiences ...

In the following days I nervously waited for Alice to mention, what had for me been a momentous occasion, and now I could not stop thinking about sex with Alice while I wore the red teddy, or perhaps the black baby-doll, and I was desperate for more.

After about a week, my patience had evaporated and as we retired, with considerable nervousness, I quietly asked if it would be alright if I wore the black baby-doll. Alice smiled, and said it was fine, and the evening was just as hot and intense as the before. And yet again there were no questions from Alice.

It was several nights later, when we had just got into bed, before Alice finally broached the subject of my desire for wearing lingerie, guessing that I might have done this before. I was nervous, but thrilled and excited at the chance to talk about my secret desires. Clearing my throat, I started my story of the Pink Tu-Tu.

''In my early years, as I was starting to be aware off my body, my family visited a business friend of my father on the weekend. As the families became comfortable, I went out to the back yard to play with their son, Rod, a year or two older than myself. After half-an-hour, his mother came out to tell us that they were all going to visit the local club, and we had the option of going or staying. Rod, my new friend, said he would stay, and I went along with it."

"Rod became a bit nervous and quite, but once he had checked that we were really alone, he became animated. 'My older sister has a chubby-house at the end of the garden,' Rod said, 'and when everyone is away, I go there to play.' Clearly this was something he kept hidden from his parents, and when he suggested that we could go there now, I agreed, excited by something that what was obviously secretive or naughty, or both."

"Before I knew it we were inside the chubby-house and the door shut. It was surprisingly spacious, with a small table and chairs and cupboards painted to look like a stove and sink. But Rod's attention was focused on the rack of fancy costumes hanging at one end. He then made his mission clear. When I am here alone, he said, I dress up in my sister's dresses, and he asked if I would like to play."

"Relishing the tension, and well aware that this was very, very naughty, I nodded. (Alice gasped softly.) Rod quickly chose a cowgirl's skirt and vest, and in a flash was taking off his clothes. Left alone in front of the clothes rack, I selected a pink satin tutu with a short flared tulle skirt, and with my back to Rod, I also hurriedly undressed. I stepped into the tutu, pulled the thin straps over my shoulders, and felt incredible."

"I looked over my shoulder to see Rod admiring himself in a long mirror. With a huge smile, he turned and asked if I also wanted to have look. I was speechless, and again I could only nod. As Rod moved away from the mirror, he pointed his toes and slightly swiveled his hips in a feminine way."

"Taking his lead, I moved in front of the mirror in a similar manner, and I instantly understood why Rod enjoyed this secret fun so much. Even though I was already well aware of it, as I pirouetted in front the mirror the hem of my skirt lifted just enough to show that I was very aroused. I was oblivious to whatever Rod was doing, and as I was admiring myself in the mirror our fun suddenly turned to blind panic - Rod's mother was calling him!"

"In a wild panic, we returned the dresses to the hangers, got dressed, and were outside with just enough time to calm down and compose ourselves before we were found. The families had returned early as one of the children had taken ill. I was never to see Rod or his sister's pink tutu again, but after that day there were many nights when I thought long and hard about it.''

While I talked, Alice and I gently stroked ourselves as we lay together, but the "unresolved" ending was clearly unsatisfying. However, we quickly resumed our fun when Alice snuggled up to me and softly asked if I could tell her the story again. The second telling was more concise, and our excitement became more urgent when Rod asked ''Do you want to pick a dress?" And when I got to the point where I was admiring myself in the mirror in my pink tutu, Alice suddenly pulled me inside her and we both came frantically.

After weeks of hesitancy and uncertainty, I had finally confessed to Alice my long term fetish for cross-dressing, and found she was more than interested in my kinky desires. The very next night she was definitely frisky and later in the evening I had a strong indication of her growing interest. We were watching a variety show on television and one of the male characters appeared in "drag." Careful to be unobserved the others, Alice gave me a subtle nudge followed by several sly and knowing glances.

After this teasing, the wait for a respectable time to retire was excruciating. When I finally made it into the bedroom, I immediately slipped into the black baby-doll, confident that tonight Alice would find this acceptable, if not expected. By this time I had decided that the red teddy was way too tight, Alice being smaller by at least three sizes. The baby-doll, however, was a lovely fit.

When Alice arrived, she walked to the bed and gently lifted the bedclothes, just enough to see the shoulders of the baby-doll. She nodded and gave an approving smile, as if to say I thought so. Alice undressed and joined me in bed and as she ran her hand over the baby-doll, she softly asked me to continue my dressing-up story. Of course, I had given this a lot of thought in the last 24 hours and was able to take up the story of my first time in pantyhose.

"Many years later, and after many happy nights thinking about the pink tutu, I was sharing a house with a friend, Rick, whose girlfriend, Joanne, regularly visited at weekends. One day I noticed that when Joanne had done some laundry a pair of her pantyhose had fallen just under the edge of the washing machine. Feeling very guilty, I nudged the pantyhose just a little bit further out of sight and for the rest of the weekend I patiently waited, wondering if Joanne had missed, looked for, and perhaps found the wayward nylons."

"Returning home on the Monday afternoon, a visit to the laundry was my first priority. With a strange mix of relief and excitement, I found the pantyhose and I rushed to hide them in my room."

By now Alice and I were more than stimulated and we were now riding very slowly and gently together as I continued the story.

"That night, I gathered the pantyhose from their hiding place, removed my clothes and visibly shaking, carefully rolled them up each leg and then pulled them up around to my waist. With fond memories of the pink tutu, I sashayed across the room, turned off the light, and quickly jumped under the covers. After feeling how good my legs felt between the sheets and between my hands, I had to roll down the top so I could fully enjoy myself."

"Over the next few weeks my appetite for Joanne's pantyhose was insatiable. Not only was I wearing them to bed for play every night, but on some afternoons, before Rick got back from work, with much haste and trepidation, I succumbed to my guilty pleasure."

As my story climaxed, so did Alice, and I quickly followed. As we lay side by side catching our breath, I mumbled "Of course this couldn't last, and in a matter of weeks those pantie-hose were so disheveled that I had to throw them out. Joanne's pantyhose were no more. But, a few years later I had another chance to wear her pantyhose." With a wicked smile, Alice said she was looking forward to more of my kinky stories.

But, as we lay together I was very aware that my story for Alice was a condensed version. When I had recalled how the danger of getting caught by Rick added extra excitement, I did not dare tell the whole story. In my wildest fantasies my housemate secretly desired to play with boys, and he would be highly aroused to catch me playing in his girlfriend's lingerie. I imagined myself lying back on their bed- with Rick treating me like the wicked sexy gurl I so wanted to be.

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