Adventures of Alice and Alex Pt. 05

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More Cross-Dressing Stories for Alice.
1k words
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Part 5 of the 5 part series

Updated 06/08/2023
Created 11/23/2016
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Alice is intrigued to hear more of Alex's stories about his growing interest in cross-dressing ...

A few nights later, Alice and I were in bed relatively early and I took the initiative to ask if she would like to hear more of my next adventures in Joanne's underthings. She paused and coyly suggested that, to enhance my mood, I may like to "slip into something." I had not even dared to think about this, and of course was thrilled. As I was slipping into the black baby-doll, I noticed Alice was also wearing underwear- a pair of tight black briefs. Back in bed, we kissed and caressed, the baby-doll sliding between our bodies, and I began to recall my exploration of the pleasures of lingerie.

"A few years later, between jobs, I stayed at Rick and Joanne's unit for three weeks, mostly to mind their cat. They were going on vacation for two weeks, except for the beginning of the first week when they would be working 9-5. After they left for work on Monday morning and I had the place securely to myself, I was racked by temptation. I hadn't mentioned this before, but as well as being attractive, Joanne was a rather tall girl and I was aware that, as well as her pantyhose, there was a good chance that some of her other clothes might fit me."

"I tried to distract myself with tasks around the house but finally decided I must get out for a walk. I headed off for the local shop to purchase something- anything. At the local shop there were two women customers and a salesgirl, and as I circled the shelves I still could not escape from my secret desires. I was fascinated by how they women had coordinated their ensemble, their jewellery and make-up; and wondered how it would look on me!"

"I took a deep breath, and calmly told myself that I was just postponing the inevitable. I bought a few items and then forced myself to walk as casually as I could back to the unit. My first step was, of course, a visit to the laundry basket. This proved to be a mid-week treasure trove; there were three sets of panties, bra and pantyhose. I chose what looked like the most used example of each and, trying to keep myself relaxed, spread the lingerie on the bed in Rick and Joanne's bright and sunny bedroom."

"After a quick shower, I returned to the bedroom in a towel. Sitting on the bed, I examined the panties- plain white briefs with just a touch of lace and size 10. I discarded the towel and pulled on the panties- they were very tight, and felt fantastic. Although I had done this before, I was shaking as I rolled the pantyhose up my legs and needed to pause and take a deep breath before standing up and pulling them up over my hips. My body tingled as I stepped to the end of the bed, to admire myself in the mirror. I posed, pouted, and twilled, and as I touched myself, my thoughts returned to the first time I had played dressing-up in that delicious pink tutu."

"I got so excited that I pulled down the panties and started to seriously stroke myself but my attention was drawn back to the bra. With some difficulty, I tucked myself back into Joanne's panties and tights and as I sat on the bed examining the bra, the temptation to wear it was overpowering. It looked fairly simple, hooks at the back and some adjustment in the straps. As I had seen girls do, I slipped an arm though each strap and went to attach the hooks behind my back. Unfortunately, this was not as easy as it looked, and anyway the straps were far too short. Disappointed, I removed the bra and looked at it once more. I slightly adjusted one of the straps and noticed that the glide had left a mark in the fabric. Joy and relief- I could safely adjust the straps to their full length, and later confidently re-set them back to Joanne's correct size."

"The problem with the hooks did not take me long. After fully extending the straps I fastened the hooks at the front, then swiveled the bra before fitting the straps over my shoulders. My efforts were rewarded when I returned to the mirror, my feminine look enhanced by my then shoulder length hair. But it was not long before once more I pulled down my knickers and was spraying my cum all over the towel."

With this Alice stretched open one leg of her panties, pulled me inside her, and we both came as our bodies thrashed together.

It was a couple of days later before Alice again mentioned my secret fetish. Driving on our way home she said "So, when Rick and Joanne were on vacation, I suppose you had plenty of time play in her lingerie?" I answered with a wide a grin, and couldn't resist adding "... and more."

I explained that when I had the unit to all to myself, I had the chance to fully explore Joanne's wardrobe. Alice was intrigued, but said she could wait till we got home to hear all about it. I readily agreed. I then ventured to recall the last time I wore the baby-doll, and she had worn black panties.

When I asked if this meant she was getting into wearing lingerie, Alice shook her head to indicate a definite no. But she blushed and smiled as she said "It's for a very different reason ... um, ... when I touch myself I like way the fabric under my fingers is a softer, more gentle, feeling. Now keep your eyes on the road, but something like this." Alice placed one hand in the crotch of her jeans, then tightly squeezed her thighs around it, and gently moved her fingers. After one quick glance (OK, two) and breathing deeply, I begged her to stop- It was very distracting and badly affecting my driving. We both agreed it best to wait until we could fully indulge ourselves in private.

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AnonymousAnonymousalmost 7 years ago
Lucky

Damn you are one lucky guy to have a girlfriend that not only understood, but also indulged to some degree. I would give my left nut to have a girl like that. Enjoy!!

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