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Jack's Little Bitch

Learning to be a girlfriend
Steph had been gone for about one week out of her two week visit to her Mom. She'd asked me to pick up the mail and water the plants while she was away, because her boyfriend, Jack, was also going to be away for the month on a business trip abroad.

“Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.”

Steph was right inasmuch as I could be trusted to look after the place whilst both she and Jack were away, but sadly I couldn’t trust myself to keep away from her things. Steph was particularly girly, and had an enormous collection of clothing of all kinds, as well as loads of accessories, make-up, and even wigs from her former stint as an amateur actress.

At twenty-two years old I was what one could consider a skinny guy, though not at all bony. I looked rather androgynous really, which helped me inasmuch as I enjoyed dressing up as a girl for private pleasure. I say private pleasure because I had never plucked up the courage to go out in public. In fact, I had never even told anyone about my cross-dressing. I also say private because the act of dressing up as a girl invariably resulted in sexual pleasure through masturbation. Ever since I was a young boy I had cherished the look and feel of soft feminine underwear adorned with pretty bows hugging tightly at my cock.


I stood there in Steph and Jack’s single-bedroom apartment, looking out through the window at the courtyard, breathing heavily. I'd known ever since I’d accepted to take care of the place that I wouldn’t be able to resist. So far I had managed to limit myself to sneaking a look in Steph's underwear drawer and only briefly opening the wardrobe to see her collection of dresses. That was three days ago.

I turned around and looked down at the bed. My cock was already quivering at the thought of wearing her delicately embroidered yellow summer dress, with its frilly white hemline. I told myself that I needed to remember exactly where I had found it, and made a mental note.

I pulled the curtains shut and then stripped my clothes off before slipping the dress over my head and smoothing it down over my thighs. The back zip was a bit tricky at first, but once I had managed to pull it up, the fit was almost perfect; except for the fact I had no breasts. I thought that Steph was probably more or less the same size as me - except for my slightly taller height - but I hadn’t expected the dress to feel so natural on me. My shaft shot straight up, causing an annoying disturbance to the image before me as I looked at myself in the full-length mirror. I felt conflicted by seeing myself as a girl with an unwanted protrusion, and yet that protrusion was also giving me great pleasure. I knew there was only one way to make it go away.

Taking great care not to disturb anything, I reached into her lingerie drawer and took out a beautiful pair of silky white ruffled panties and matching ruffled bra, as well as a few pairs of silk stockings to pad the breasts. Quickly, I unzipped the dress, slipped into the underwear and put the dress back on. It fit perfectly now, my fake tits amply filling the breast pockets. In a frenzy, I rushed over to Steph's wardrobe and pulled out a curly blond shoulder-length wig from one of the boxes, and put it on.

The excitement was building; my cock was dribbling pre-cum into Steph’s pretty little panties as it tried desperately to fight its way free.

Seconds later, the girl in the mirror was smiling back at me. I knew her well. She had given me much pleasure over the years. I looked her in the eyes while grasping tightly at my throbbing rod through the silky material. She was the most exciting girl I had ever known. I watched her writhing about while I rubbed my swollen shaft, glancing at her delicate curves and admiring her femininity. She reached up and grabbed her left breast, rubbing it seductively. I could sense her every move, the softness of her delicate mound being teased beneath my wanton hand. I watched in awe as she squeezed and rubbed her titties, taunting me. I wanted her so badly.

I leaned in to the mirror to kiss her, desperate to connect. We had made love many times before, and yet we had never felt the warmth of each other’s bodies. She loved to tease, and I loved to watch her. She had a way of showing off just enough of herself to get me totally excited, like turning around and lifting her dress, just enough to show off the beautiful curves of her tight little butt, or to stand facing me and show me the tops of her milky white thighs.
I especially liked it when she wore stockings and a garter belt beneath her dress or her skirt. She was a real mistress, knowing just when to turn it on and off.

I stroked vigorously at the head of my shaft as she pulled away from my vain attempts to kiss her. She played with her breasts, stroking herself, running her hand down her stomach and across her thighs, lifting her dress, and then returning to touch her breasts. She did this a few times, until finally she raised her dress enough for me to see her bulging cock encased in frilly white panties, the head of her shaft popped out over the top, and the tip spurting a steady stream of sticky white cum in my direction. I gasped as I watched, my balls pulsating deeply and quickly draining.


The following morning I lay in bed, remembering the events of the previous day. Even though I’d had to take Steph’s dress and panties home to clean them, and the fact that I felt somewhat ashamed of having violated her privacy, I wanted more. The sense of pleasure outweighed the guilt, as I discovered later that evening.


I stood in front of the mirror, putting the final touches on my makeup. The lash curlers had worked out better than expected, and despite my nervous hands, I had accomplished a delightfully vampish look, complete with sultry ruby red lips. I smiled and admired my alter-ego, the girl who was me, with her long dark curly hair (a wig), wearing her black velvet mini-dress and thigh-high stockings. It would be almost a week before Steph came home, and I needed to take advantage of that. Several more evenings of fun lay ahead.

I went to the bedroom and flopped down on the bed in front of the television, imagining what it would be like to be Steph. I ran my fingers up and down the stockings, feeling the thread. My leg tingled in a sensual way, and I wondered if Steph would feel the same way if I stroked her legs like that. I pushed my hand further between my thighs and rubbed my inner leg. The sensation of the stocking material caused my shaft to stiffen, some pre-cum dribbling from the head. “Of course she wouldn’t feel exactly the same, but possibly similar, at least in her mind.” I said to myself.
I felt contented with idea that she possibly felt the same as me, and I was not at all inclined to jerk-off again. “It’s so unladylike!” I thought to myself.

As I lay there, oblivious to the TV programme playing on low volume and feeling contented with my evenings accomplishments, I drifted into a deep sleep.


At the sound of a key in the front door, I leapt up and ran into the bathroom, closing the door behind me.

“Fuck!” I yelled internally.

I looked at my watch and realized that I had only been asleep for about an hour. I was lucky that I’d heard anything at all. I summoned a few brain cells, reassuring myself that Steph was only due back by next Friday at the earliest. Then it suddenly dawned on me that she hadn’t been very specific about Jack’s dates. She had said that he would be away for a month, but I hadn’t registered quite from when. I rationalized that she wouldn’t have asked me to take care of the place if he was expected to be home at any time soon, but obviously something had gone wrong.

“Steph?” Jack called out, “Are you there?”

I stood behind the bathroom door, holding the handle firmly upwards for a few moments to prevent him from coming in, but there was no key to the lock. The effort was futile; I knew that I would be discovered within seconds and that I didn’t stand a chance to hide anywhere. I wondered how I had managed to be so stupid.
I felt scared, sinking down to the floor, sitting despondently and holding my arms around my knees, my head buried between my legs in shame.


It took Jack a good five minutes to stop laughing. At first – and for a few seconds - he’d looked at me quizzically, but after realizing who I was he’d burst into a series of huge guffaws, bending over double and trying to catch his breath between raucous episodes. Eventually, h e stumbled out of the bathroom and tumbled onto the couch, exhausted.

I stood up and walked out of the bathroom, still fully-dressed in Steph’s clothes, waiting for my fate. Flashes of Jack telling everyone he knew, Steph knew, we all knew, posting public pictures of me on the internet, murdering me, or perhaps simply punching me in the face came to mind. I would have gladly been beaten up if that mean the end of my exposure.

“I guess I should call you Steph?” Jack said, still trying to contain his merriment, “or is it Mandy, Candy or Wendy, perhaps?”

“I’m really sorry!” I replied sheepishly, “I had no idea that you would be home so soon.”

“Neither did I”, said Jack, “And I certainly wasn’t expecting see this!”

“I feel really embarrassed,” I continued, “I’ll get changed now, if you don’t mind?”

Jack sat there on the couch, staring at me intensely, eying me up. His eyes roved over me and my body, from head to toe. He seemed to be judging me, appraising me for some purpose.

“Listen Mark,” he said, finally “I’ve just spent three weeks on some pretty serious business and now I come home to find this going on in my own home.”

“I’m really sorry!” I started up again, “I…”

Jack interrupted me.

“Nobody’s saying anything, OK?” he continued, patting the bedcovers beside him. “Come and sit down here and we’ll talk about it.”

The way he beckoned me to sit next to him, the power of his command, and the gentle way in which he was managing the situation made me want to follow him. I walked over to the couch and sat beside him, whereupon he immediately put his hand on my upper thigh. The feeling of his strong masculine hand grasping my leg through the thin stockings caused a shot of pre-cum to dribble forth.

I sat there in silence, my head bowed, waiting for him to speak. Clearly I had screwed up in many ways. I was just hoping that he would have a bit of compassion, and tht he would let me off lightly.

“I don’t know why you want to wear those girly clothes,” he started, “and I don’t rightfully care, but if they make you feel good, then I’m not complaining.”

He pushed his hand up between my upper thighs and grasped my balls in his hand. Then, he looked me straight in the eye and said, “Do you understand what I’m saying?”

“I think so,” I gasped, hoping he wasn’t going to hurt me.

“You’re damned right, you understand”, he said, unzipping the front of his jeans.

He pushed my head down into his crotch, his cock springing forth out of his underpants.

“Come on you little bitch, suck me off!”

He thrust the tip of his burning rod straight into my mouth while grabbing the back of my hair, and then went on to pump his member in and out of my mouth like I was his personal whore. I had never taken dick before, and I was obviously shocked at what was happening, but it felt so right, like something I had been missing for years.
Within seconds I was lapping at his cock like a pro, teasing the length of his shaft with my tongue and sucking dearly at his knob until he was about to come. I wanted to feel the thrust of his hard cock between my lips, and his jet of cum flowing into my throat.

Jack pushed me over on the couch and pinned me down on my stomach, his hand firmly across my back.

“I’m going to fuck you in the ass, you little cum hungry whore!” he growled at me.

I lay there face-down while he grabbed the back of my silky panties and tore them off in one swift motion, the ripping sound filling the air with a sense of violation. I was totally exposed.

Next, there was a sensation of coldness dribbling between my butt cheeks as Jack poured lubricant on me, followed by the warm sensation of his hands sliding between my thighs from behind me.

“I’m a virgin.” I squealed, hoping that he would go easy on me, but also hoping that the feeling of his fleshy meat inside me would feel as good as I imagined it would be to have a man inside me.

Jack didn’t pay any attention to my concerns. Instead, he prodded the thick throbbing head of his cock against my tight little butthole with the intent to penetrate. He flicked back and forth, jabbing at the opening to force an entry, the glistening product he’s applied only slightly easing the passage. Finally I eased up, and he slid inside me, his thighs pressing hard against my buttocks.

It felt good to feel the length of him deep within my body, as though he belonged there. He moved back and forth rhythmically, pumping me with his meaty shaft, determined to squirt his load.

“Oh my God, you’re a fucking virgin whore!” he yelled at me, "You're so fucking tight!"

I lifted my ass in the air, spread my buttocks as wide as I could, and begged him to deliver.

“Please come inside me!” I wailed, practically crying. I so much wanted to be a girl, my dress hitched up around my waist, my face stuck into the pillow, my rear quarters just begging to be drilled. I felt vulnerable and wanton for Jack's hot cock.

Obligingly, he thrust forward and pumped my ass with his thick creamy sticky cum, groaning loudly while he grabbed me around the waist, pulling me down onto the couch next to him.


For the next several minutes we didn’t say anything.

Finally, Jack put his arm around me and looked me in the eye.

“You’re a really cool chick. We should do this again some time.”

Needless to say, that wasn’t the end of our adventures.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © © 2018 Lars Kaiden. All rights reserved.

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