First Time Drag Ch. 02

I've received wonderful comments from many of you. It's these comments, both those that appear below the story and those that are sent to me privately, that drive me to write more.

When I wrote "First Time in Drag", it was my intention to provide the reader with a quick gentle love story. The ending was to be a happy one, but final. To my surprise, many of the comments I received asked that I continue with the story. This will be my first 'extended' story.

Well, here goes.

------------------

We'd been together for almost one full year, maybe the happiest year of my life. Michael had expanded his feminine side, dressing up and wearing makeup more often than not. His hair had grown too, now almost at shoulder-length. Though twenty-one, he was still really just a boy, or maybe just a girl. I was in my early forties, Michael occasionally calling me 'daddy'.

Michael continued with his Computer Science classes doing very, very well. At my suggestion, Michael kept the feminine side of his life private, within our home. The stigma of exposing himself at school would just be too great among a bunch of college rowdies, possibly even causing him physical danger. I told Michael that in the future, if he desired to 'come out', I'd support him with all my power. Michael agreed with my thoughts, hugging and kissing me.

When Michael first moved in, he'd wear some clothes that an ex-girlfriend of mine had left. He was soon uncomfortable with that and wanted clothes and makeup of his own choosing. He and I would shop together at various up-scale stores, usually under the guise of buying something for a relative. Michael would choose most of the clothing and makeup, his taste was excellent and he was never extravagant. Our relationship was a happy one, filled with love and understanding; of course lust was a big part of things too.

One evening we were watching a film together, Michael curled beneath my arm wearing light makeup and a camisole, when he said, "I'd like to get a little nasty tonight if you don't mind, I really do enjoy making love with you, you're so gentle with me, especially with the big cock of yours, but sometimes a girl just wants to get fucked."

My mouth hung open for just a second then I burst out laughing. "I'd like that very much young lady," I said.

Michael then spent the next two hours, yes two hours, getting ready! He was a little too much like a woman at times, but it was a very small price to pay for what I received in return.

As Michael prepared the bedroom and himself, I had several glasses of a deep, woody California cabernet. The wine and the thoughts of what was to come both warmed me. I realized I was very, very aroused. The thought of Michael being a little slutty was exciting. From the bedroom I could hear Michael finally say, "I'm ready, come on in."

I entered the bedroom holding my glass of wine along with one for Michael. I placed the glasses on the dresser and looked at Michael, he was stunning; his clothing and makeup perfect. It'd always amazed me how Michael was able to dress up so well with none of that clownish over-the-top drag-queen look. Michael was dressed in short smooth dark-gray lingerie, not too much lace. His legs were encased in very dark sheer hose, the tops of the hose requiring no garters, free of any obvious support. He was wearing black suede pumps and a single platinum necklace, his only accessory.

His makeup was, as usual, perfect. He knew I liked him to wear a little too much eye shadow; dark-charcoal in color, along with that deep wine-colored lipstick I found so sensual, his lips outlined by a thin black line. His eyeliner and mascara were just right too. I could see just a touch of powder on his cheeks; he didn't require much there with his flawless skin and over-all tan.

The room was filled with candles and there was a presence of light incense; possibly vanilla, soft sensual music played. Michael approached me and put his arms around my neck, "Do you like?" he asked.

"Yes, very much."

"Tonight I want you to call me Michelle, I know it sounds stupid, but it's something I've been thinking about a lot. Is that OK?"

"Why yes ... Michelle."

He guided me to a nearby chair and sat on my lap; I was always surprised at how light he was. He encircled my neck with his arms, looked into my eyes and said, "I want to be your slave tonight. I want you to forget how much you love me and use me like someone you'd never met before, can you do that?"

I thought for the briefest of moments and answered, "Yes, now help me off with my shirt." I pushed him aside and stood up. Michael ... sorry, Michelle, helped me remove my faded polo shirt. I pushed him to his knees and said, "Now the pants."

Michelle undid my belt, then my pants. He slid the pants down my legs and helped me step out of them. "Do you want my cock?" I asked.

He looked up at me with that beautiful young made-up face and said, "Yes, use my mouth and throat any way you like."

His simple act of submission made me mad with lust. I said, "Suck it then, through my briefs."

He began to run his hands over my cotton-covered erect cock, kissing and sucking it, leaving smudges of lipstick on my briefs. He pulled my briefs down, the elastic cupping my balls. He began his assault on my cock, much different than any time before, much more nasty.

He licked, sucked and drooled, occasionally looking up at me. I was in ecstasy, never having been this aroused before. Michelle said, "I want to be your whore tonight, just use me."

I dropped the briefs, standing nude before 'her'. My cock was sticking straight out, filled with hot blood. Michelle sucked it for a while, smearing the cock-shaft with lipstick. I sat down and had her sit astride me. I could see that Michelle was wearing a tiny pair of black panties, her erection pushing against the fabric. I pushed her panties aside and began to stroke her long slender cock. I held mine against it and stroked both cocks together.

She then got on the bed, head in her hands, back arched, ass high. I approached her and caressed that phenomenal ass. Michelle's ass had always made me crazy. It was perfect, smooth, blemish-free and tan; her ass cheeks were 'dimpled' at the sides. I shoved her legs apart and smacked her hard on the ass. I'd never struck Michael before, but it seemed right to give one to Michelle.

Michelle groaned in lust so I gave her three more smacks, her ass now red with my handprints. I grabbed the straps of her panties and literally tore the panties from her body. Her young asshole was contracting and expanding in passion.

I reached for a bottle of lube and liberally applied some to my raging cock. Michelle breathed, "Use me."

I guided my cock to her dark orifice then pushed into my little slut. I pushed with long steady pressure, my cock soon fully buried in her 'pussy'. I could feel my balls slap against her thighs. I reached down and grabbed her by that thick luxurious straight dark hair. Michelle began to buck as I fucked her with long powerful strokes. She was moaning and breathing hard like I'd never heard her before. I soon arched my back and emptied my seed deep into her guts.

I fell to my back, my cock pulling free. Michelle spun around and licked my deflating cock with desire. Her actions caused me to twitch as she continued to clean her juices from my cock. She said, "Thank you daddy, thank you."

I rested for a few minutes, Michelle's mouth slowly sucking my now soft cock as she masturbated. I said, "Thank you baby, you're one amazing little girl."

"I want more please, turn over and I'll get you hard again."

I thought; 'she's pretty wild tonight'. She had me lie on my stomach and spread my legs. She got behind me and slowly licked my asshole. I could feel the bed vibrating as she masturbated. Soon her ministrations had the desired effect, my erection returning in full force.

Michelle licked and probed my asshole with her tongue. I'd got onto my hands and knees allowing her greater access. This was the first time she'd been the aggressor; it was always me guiding her.

My forty-year-old cock was soon at full strength when she said, "Be right back," and skipped to the bathroom. She'd gotten me hard and then abandoned me! She did quickly return, her makeup refreshed, however, in her hand was something I never expected to see, a large flexible black dildo. She handed the dildo to me and said, "I want you to use this on me tonight."

I was stunned, sort of. We'd never before played with 'toys'; where did she ever buy this thing? I said, "Are you sure, this may hurt."

"Yes, I tried it once before, I think I like it."

I said, "Get on those hands and knees then." She did as directed and I joined her at her side. I lubed up the dildo and spread her ass cheeks, placing the end at her hole. The dildo was much thicker than my cock and I wondered if she could accommodate that monster. I slowly eased the dildo into her pussy. I could feel her push against my pressure, seemingly wanting the dildo buried in her young hole. The dildo actually had a grip at its base and a 'hilt', much like that of a sword.

I started slowly, and then increased both length and speed of the strokes. Michelle responded with passion, crying out as I fucked her with that black intruder. Where did my little 'baby' get these ideas?

The fucking was soon too intense for Michelle and she arched up, head back, hands on her thighs. Hot cum sprang from her slender cock, the motions and pressure of the dildo causing her to ejaculate without any touching of her cock. She fell back into my arms as I eased the dildo from her abused young hole. I held her there, softly kissing this amazing young girl.

We rested for a bit, holding one another close. She got up and went to shower. I knew she valued her privacy following sex, so I let her have some time alone. I used a separate bathroom for my ablution and then returned to the bedroom. Michelle was waiting for me there, fresh, clean and beautiful. She ran to me and held me in her arms. "You're so good and kind, please never ever leave me."

I held her near, "I'll be with you always."