January 2019 "Reader Retention Contest"

(This story is semiautobiographical adult fiction. Explicit content. There are six chapters. All rights reserved. Comments are appreciated.)

Chapter 3 of 6 (Not work place safe)

Our story follows 72 year old Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. Her story culminates in her final purge.

Have you ever been the ‘new kid’ in school, feeling alone and in need of a friend? I find Michelle and Michelle finds Joanie. It was a summer of discovery that I’d never forget.

Previously

Mom remarried and we moved to sunny and warm Southern California. I was the new kid in town again and was desperate to make friends and become accepted by my peers. While searching for friends I met Michelle.

Chapter 3 - Some boys do!

Throughout elementary school I had acquaintances but never had a close friend or buddy.

In junior high school, during the early 1960s, I found a friend who was more involved with his feminine side than I was. Mike also was an only child. He was a year older than me. We were the same height. His single mom was raising him by herself and worked 10 hours a day trying to make ends meet. As a result Mike was left unsupervised most of the time and he had found unique ways to occupy his time. He could be called a ‘latch-key kid’. Since Mike lived only two blocks from me he and I became buddies. It turned out we had at least one thing in common. We spent a lot of time together.

I happily discovered that I was no longer alone with my ‘weird desires and thoughts’! I watched as Mike applied lipstick, painted his nails, dressed in his mother’s clothes and wore her shoes. With my very willing participation I let him paint my lips with his mother’s lipstick (“Cherries in the Snow”). Since Mike’s nails were painted (and looked pretty) I let him shape and paint my nails too. The polish matched my lipstick. This day was a very big step in my life; it impacted my life forever.

I was cleaning my finger nails before going home when Mike suggested that I leave the polish on my toes. “We’ll be The Pretty Nails Club” he quipped. “Just keep your socks on around your parents.” Mike was a gentle soul and would become a mentor to me in more ways than I could have ever imagined.

The next day I returned to Mike’s house or Michelle as she called herself when in femme mode. She was already wearing tan colored pantyhose, a laced trimmed yellow bra, lipstick and nothing else. No panties allowed me to see her flaccid cock. She had several bracelets on her right wrist. I was clearly intrigued by what I saw. All her nails were a bright red again. “Wow, your legs look so nice” I said. I was talking about legs but was staring at her penis. Michele noticed my staring and smiled. “Yes, legs and dicks do look nice with hose and they feel even better to the touch. Nylons with heels make legs look even nicer. Care to try a pair?” she asked.

Without hesitation I enthusiastically said “Oh, yes that would be great!” Michelle said “I’ll show you the proper way to put on stockings. Remember that you can’t just tug them up your legs. There’s a method you need to follow. First you must roll them up in a special way before you begin to put them on or else you’ll rip them. Before we begin you need to slip into some proper panties and a bra. You should never wear hose without panties.” Michelle handed me the lingerie she wanted me to wear. They were bright red.

As I was shedding my jeans, t-shirt and boys underwear Michelle tossed me a tube of his mother’s lipstick and told me to put some on. I did. Oddly enough the red color matched my borrowed lingerie. I was struggling with my bra when Michelle came over, adjusted the straps and hooked me up. Stepping away she playfully snapped my bra strap. “You can do the same for me someday. Remember you hook my bra and I’ll hook yours. That’s what friend’s do.” she quipped.

Standing in only panties and bra, as instructed, Michelle looked at my feet and commented “I’m glad you left your toe nail polish on since it matches your panties and lipstick”. I’m not sure why but I was glad that she had noticed. “Let’s go into my bedroom so we can get you into some pantyhose”.

I had watched my mother put on her stockings many times before. I knew how it was done yet I said nothing. I willing went into Michelle’s bedroom.

Michelle had me sit down on the edge of her bed. Michelle sat down next to me; she held a pair of sheer black pantyhose that she had rolled up in a special way. Extending my left leg and pointing my toe as she requested, Michelle leaned over and positioned one leg of the hose on my left foot. She began rolling the nylon up my leg to just below my knee. “You got to do a little at a time. Don’t be in a hurry if you want to have pretty smooth legs. Now extend your right foot”. Michelle repeated the process and stopped when this hose was in the same place as it was on my left foot. “Carefully stand up, turn around and face me” she instructed. Michelle remained seated.

I stood and made a hobble turn hop and was standing facing Michelle. “Come closer” she beckoned. Her voice sounded different; almost sultry. I was standing between her legs and my panty encased pelvis was level with her face. The nylons were bunched around my ankles. Michelle blew a prolonged but steady stream of air directly onto my panty hidden crotch. I felt her warm breath and my penis began to involuntarily swell, my mouth became dry and I felt lightheaded for an unknown reason that my young brain didn’t fully understand. Michelle stared straight ahead. She blew again. Without looking up, and while staring at my panties, Michelle softly said “Here comes the fun part. You need to slowly and evenly pull your hose up each leg like this”. Following her own instructions Michelle bent over and expertly rolled the hose the rest of the way up my legs. Black nylons contrasting with red lingerie are a beautiful sight.

Looking up and into to my eyes Michelle said “A proper girl needs to smooth out her hose. Wrinkles aren’t lady like.” While maintaining eye contact Michelle used both hands to slide and smooth the wrinkles from each leg. She began at my ankles and drew her hands upward. Her hands were so gentle. It felt great to have someone caress my legs.

The feel of the nylons combined with her touch had my knees quivering. Michelle stood up and we were belly button to belly button. She smiled at me charmingly and said “You need to make sure that the rest of your pantyhose are smooth; not just your legs”. Using an open palm she began to slowly stroke my crotch in slow repeated upward movements as if she was petting a cat. It felt so good that my breathing became more rapid and my knees became weaker.

“Look how I’m smoothing your nylons. See how much better they look now? It feels nice for me to smooth your nylons doesn’t it?” I broke eye contact and looked down. I was barely able to gasp out an agreement. I nodded my head and demurely said “Yes, my nylons look much nicer and yes, smoothing them feels incredible.” I was panting with pleasure by now. Michelle stopped her stroking but left her hand on my well defined lump. I was in heaven.

Speaking softly Michelle pointed out that it appeared that her nylons weren’t smooth all over either. I took the bait and reciprocated with the same smoothing and stroking of her nylon covered crotch. I could feel the heat and firmness of her cock through her panty hose. My penis twitched. So did Michelle’s. It felt delightfully naughty. I let my hand linger on her bulge enjoying a new experience; my first cock. She pressed my hand more firmly to her penis. On purpose Michelle made her dick throb making sure that I felt it.

Without stopping her ministrations on my boy bulge Michelle leaned forward and kissed me. I could taste her lipstick. She gently caressed the length of my cock several times from the outside of my pantyhose. I made my dick throb for her. It was all so very pleasant. My penis was beginning to protrude above my hose. As I reciprocated her kiss Michelle pulled my pantyhose and panties forward enough to be able to run her thumb tip around and around the pee hole of my raging hard-on. It was yet another first for me. It appeared I was leaking something. I was naïve about preseminal fluid. Whatever it was it made Michelle’s rubbing of my cock head more slippery and more erotic.

Reaching deeper into my panties Michelle grabbed and hefted my ball sack. She briefly and gently massaged my balls. Releasing my balls Michelle encircled my dick with her warm hand and gripped it snuggly. Using her thumb again Michelle began doing what she knew would give me the most pleasure. Her snug grip was warm and affectionate. By reflex I reached into her panties and grasped her cock. Whatever Michelle would do I would reciprocate. I found her wetness. She gasped and leaned a bit closer. We continued to make out.

Michelle then grasped my penis like you would hold a coke bottle and began to slowly and gently stroke my shaft up and down being sure to spread my wetness along my shaft. Her stroking felt nicer. I returned the favor. We may have been standing there for hours for all I knew. What I did know is that I didn’t want the moment or the slippery sensations to stop. It was a new and beautiful thing.

Michelle broke our kissing and pulled me onto her bed. I didn’t resist. Sitting on her bed she kissed me again but this time she inserted a little of her tongue into my mouth. Her tongue probed. My body quivered and I tongued her back. Our tongues entwined. I thought the day couldn’t get any better as I was experiencing yet another, incredible, first. I squirmed a little and she gently laid me back as she straddled me. Lying on top of me she ground her nylon covered crotch into my nylon covered crotch. The slow humping and rubbing made my dick harder than it had ever been before. I experienced lust and desires that I never knew existed. Both of us wearing pantyhose made it all the more erotic. In retrospect I think that made me Michelle’s ‘bottom’.

Michelle stopped kissing my lips and lifted my bra for ease of access. Her mouth and tongue moved to my nipples. She sucked, nibbled and kissed each of my nipples into a delightful hardness. I loved it then and I still love it today!

Next - Chapter 4: Michelle straddles me (Not work place safe)

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