'Jenny' & 'Mike': Fantasy Sunday

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More gender reversal pegging with fantasy play.
9.6k words
4.7
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Part 3 of the 4 part series

Updated 08/30/2017
Created 07/20/2016
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This is the third chapter in the 'Jenny' & 'Mike' series. If you haven't read the first two chapters 'Jenny' & 'Mike': Date Night and 'Jenny' & 'Mike': A Day Out, then please do check them out. As already stated, my interest in pegging was the starting point of this series. It has since developed into more of an exploration of 'Gender Play' with our happy couple enjoying reversing their gender roles.

NOTE: I would like to thank CJ_ED, Lord Dark Star, Mistress Joanna, shygirlwhore and Minnie & John for editing my story.

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CHARACTERS:

James Winchester / Jenny

Michelle Winchester / Mike

Carmen

NOTE: This installment is told from Michelle and James's points of view.

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MICHELLE'S POV

The alarm was buzzing, and I couldn't understand why. We never set it to go off on Sundays. I tried to open my eyes as best as I could. It was only 9 a.m.! I reached over and tried to shut the darn thing off. After a couple of failed attempts, I finally found my target. The awful noise stopped. I turned around realized that James was no longer in the bed with me.

"James?"

No answer. I got out of bed and headed for the bathroom, certain he'd be in the shower. I was surprised to find it empty. "James?" I called out again. Still no answer.

I put on my slippers and headed downstairs. Maybe he was preparing breakfast. I could do with a cup of coffee, I thought to myself.

I was still daydreaming of the cup of coffee I would soon be having, when I stopped in my tracks. James was certainly not in the kitchen. 'Jenny' was.

"Oh, Good morning Mr. Winchester," she said, turning from the kitchen counter where she was brewing the coffee that was on my mind a few moments earlier.

My jaw dropped as I got a good look at her. She was dressed in a maid's uniform consisting of a black shirt with sheer sleeves and a black ruffled petticoat over which she wore a white pinafore with black polka dots. Her legs were covered in thigh-high fishnet stockings held up by garters. The stocking-tops were clearly visible under the short hem of the dress. On her feet, she wore highly impractical four-inch pink patent leather heels. I could not help but appreciate the ruffled white French maid's headpiece with the jaunty pink bow on top. Such attention to detail!

"Mr. Winchester?" she asked me again, rousing me out of my daze.

"Uhm... sorry. Yes?" I managed finally.

"I'm Jenny, the new maid. Your wife has gone out for a bit to run some urgent errands. She'll be back in a few hours."

"My wife?" I asked, confused.

"Yes sir. Your wife. Mrs. Winchester," she replied, a devious smile creeping up on her face.

"Oh... Oh... yes. Okay," I managed, my sleep sodden mind finally catching on to what was happening. James was in character. He had certainly been quick to act on the role-play idea we had discussed the day before. A slow smile spread across my face as I began to look 'Jenny' up and down.

"Mrs. Winchester asked me to give you this note when you came down," she said, stepping closer and handing me the note.

I took it, all the while eyeing her up and down.

Dear Mike,

Enjoy some breakfast. Take a shower. Stay in character until the end and enjoy!

Xoxo

Jenny

"Did she say when she'll be back?" I asked, finally getting into character too.

"She didn't say, but she did tell me to serve you breakfast and take care of a few things around the house," our 'new maid' responded.

"Okay," I replied, taking a seat at the table.

While 'Jenny' prepared my breakfast as instructed, I continued to leer at her from where I was seated at the table. Her uniform left nothing to the imagination! This was going to be fun!

"So, how long have you been working for my wife?"

"It's been a week now, Mr. Winchester."

Mr. Winchester! She was going all out and I loved it!

"Why have I never seen you before?"

"I usually come in the mornings around 9 a.m., sir."

"Right after I leave, huh? And what time do you usually leave?"

"Usually around 2 p.m., sir."

"So you leave before I come home then."

"Yes, Mr. Winchester."

"Do you always dress like this?" I asked with a raised eyebrow and a nod towards her outfit.

"In uniform? Yes, sir. I had nothing else to wear today, so I had to wear this one, Mr. Winchester," she said, with a coy smile. "I am usually dressed a little more conservatively."

"Well, you look very nice today. Very sexy," I said, openly leering at her now.

While we were talking she had been busy preparing a plate of blueberry pancakes which she now placed before me with a fork and napkin.

"These look delicious." I was famished and couldn't wait to take a bite.

"Thank you, Mr. Winchester. Will you be needing anything else?"

"Not for now. Thank you Jenny."

"Then I'll start with the chores around the house. Please let me know if you should need anything."

"Oh, I will," I replied with a naughty grin.

I wolfed down my breakfast, and then headed upstairs for a shower. I knew I was going to get some of that precious ass soon.

I didn't waste any time in the shower. Soon I was standing in front of the full-length mirror in my dressing room, putting on my white tank binder to create the illusion of a flat chest. Next, I put on the Joque harness that still had the eight-inch Bandit dildo attached to it. The bigger dildo would have to wait until later. I selected a blue dress shirt, beige trousers and a pair of brown leather loafers. Lastly, I drew my hair back in a tight pony tail.

Downstairs in the living room, 'Jenny' was busy with James's usual chores. I sat down on the couch, grabbed the TV remote control and began flipping through channels. Soon 'Jenny' began tidying the area around the television. When she was directly in front of me, facing the television, she bent over giving me a full view of her stockings, garters and thong-covered ass. If I had a real cock, that sight would definitely have left me rock-hard.

Still bent-over, she turned her head slightly to give me a cheeky smile as she continued dusting around the television set. She was clearly treating me to her own show. I began to squirm in my seat. It seemed her activities were designed to put her ass on display rather than ensuring that the living room was left spotless. With an innocent expression on her face, she straightened up and walked over towards the couches. Her little show had left me quite breathless.

"So, Jenny, where are you from?" I asked, trying to start up a conversation despite all hot and bothered after the little tease's sexy show.

"Oh, I'm originally from France, Mr. Winchester. I recently came here in the hope of finding some work."

"And do you like it here so far?"

"Oh, I like it very much so far, sir."

"Do you live alone?"

"No, sir. I live with a friend."

"A boyfriend?"

"No, Mr. Winchester. I share a place with another girl."

"You're so pretty, how come you don't have a boyfriend?"

"My work keeps me very busy, Mr. Winchester. My social life is kind of non-existent right now."

"That's too bad. I hope you're getting paid well for all the hours you're spending at work."

"The pay is okay, sir."

"Just 'okay'? Doesn't Mrs. Winchester pay you enough?"

"She is a nice person, sir, and I do get paid very well. Only, I get paid at the end of every week but I need some money quite urgently today. I was hoping she could pay me today. I just hope she will be back on time so that we can discuss the possibility of that."

"What if I could help you with that?" I asked, grinning.

"You could?"

"I would. But you would have to do something for me in return."

"What do you mean?"

I got up and walked up to her, getting really close. I could tell her breathing was becoming erratic.

"What are you doing, Mr. Winchester?" she asked, appearing a little scared.

I began to touch and caress her body. She shivered. In anticipation?

"What does it look like I'm doing?" I asked, grinning. I pulled her closer to me. She gasped. I looked into her uncertain eyes as I pulled her head closer and planted one on her lips, while running my hands over her stocking-clad thighs. We kissed for a few seconds. She whimpered, and then pushed me away.

"Mr. Winchester! I can't do this!" she said, after pushing me away and trying in vain to pull her much too short dress over her thighs.

"Of course you can, sweetheart. You give me what I want, and I'll make sure you get what you want. And I could tell that you were starting to enjoy yourself. Don't fight it." I pulled her in for another kiss and this time her lips parted almost immediately. She began moaning into my mouth as our kiss deepened, but then she pulled away again.

"But...but...Mrs. Winchester...." she said sounding a little uncertain, maybe even frightened. She pushed against my shoulders, trying to get out of my embrace.

"She doesn't need to know about this," I said grabbing her ass and pushing her hard against the hard-on in my pants.

"Y-y-you promise to help me?" she asked, looking into my eyes almost pleadingly.

"Of course," I said, caressing her ass more firmly.

"O-o-okay," she said, still shivering.

"Good, let's go upstairs. I think we'll be much more comfortable there."

I kept my hand on her ass, caressing it as we walked up the stairs towards the bedroom I shared with 'Mrs Winchester'. In the bedroom, I pulled her into me roughly, and started kissing her with much more force than I had a few minutes earlier. She resisted a bit at first, but slowly relaxed as our kiss grew more passionate. Just as I could feel that she was returning my kiss, I turned her around and held her tightly with her back against me and began kissing her neck, all the while running my hands over her silky stocking-clad things and towards her crotch. By the time I reached her thong I could tell she was very turned on. I slipped my hands inside them and began stroking her cock slowly.

She started moaning and whimpering almost immediately. I was beginning to get turned on by how responsive and vulnerable she was to my touch and caress. I lifted the back of her pinafore and pressed her almost bare bottom against my own hard-on.

"Can you feel that? You have me so fucking hard," I whispered into her ear. "I suspect that you were teasing me deliberately when we were downstairs."

"I wasn't, sir."

"You're a little liar. But do you know what? Your body doesn't lie," I whispered , grabbing her neck more firmly.

She shuddered as I continued to play with her cock, teasing her a little longer. When I finally let her go, I turned her around, and pushed her onto the bed. She watched me approach her with lust in her eyes. When I reached where she was lying on the bed, I shoved my crotch in her face.

"You know what to do," I whispered, grinning at her wickedly.

She didn't need any further invitation. She reached up, unbuckled my belt and began pushing my pants down to my ankles. I slipped off my shoes to make her job a little easier, and watched while she slipped first my left, and then my right leg out of my pants. I loved what she looked like as she finally settled back onto the bed, her face inches away from my eight-inch bulge, which was still covered by my boxers. She began stroking her hand over its boxer-covered length gently.

"Don't be a tease now," I whispered, gently goading her.

She looked up at me shyly as she pulled my boxers down to my knees. My cock sprang up and smacked her in the face.

I loved the look of surprise in her eyes.

"It...it...it's so big!"

"It's all for you. Now take it in your mouth," I said, tilting my hips foward and pushing my cock towards her lips.

She looked up at me as she grabbed a hold of it, slipped the tip between her bright pink lipstick-covered lips, and gave it a sneaky lick. Finally, she took the head between her lips, sucking and licking it. I thought I'd die of excitement, when she licked her tongue all the way to the base and then back up the shaft before focusing her attention on the head. She teased me like this for a few minutes, before taking my entire length in her mouth.

"That's it, slut! Suck my big hard cock."

She moaned in answer, and wrapped her hand around my cock, pumping it with her hand while her mouth was still sucking on it furiously. I pulled my cock out of her mouth. I loved her lipstick-smeared lips, and the traces it left on my cock.

"You like sucking on my cock?" I asked, grabbing her head.

"Yes, sir," she replied eagerly. I forced my cock into her mouth again, and held her head in place for a few seconds, my cock deep in her throat. Just as she began gasping for air, I released her.

"You like sucking big dicks, slut?"

"Yes sir."

"I can tell that you do. I bet you do this with all your other employers' husbands too."

I pulled her down onto my cock, forcing her to deep-throat me again. This time, I held her in place for a little longer. She tried to breathe but the effort only resulted in her mouth becoming messy with her own saliva.

I hurriedly removed my boxers, which were still crumpled around my thighs and knelt beside her on the bed. I grabbed her head again, and pushed my cock into her mouth once more. She reached behind me to stroke my ass as I face-fucked her. Her eyes were glued on mine as I worked my cock in and out her mouth. I could tell that she loved being treated like a whore.

After a few minutes of rough face-fucking, I decided that she had had enough. We needed to get down to the real action. I pulled out of her mouth and roughly turned her around so that she was on her knees with her ass towards me. I lifted her petticoat and pulled her panties down. I loved the sight of them around her thighs. I reached over to the nightstand and grabbed some lube from one of the drawers. She moaned softly as I squeezed a generous amount along the crack of her ass. She was about to get the best fuck of her life and I didn't want to go in raw. I slathered my cock in lube too, and then aimed it at her asshole. She whimpered as she felt the tip touch her hole, and groaned as I gently pushed the head inside.

I leaned closer, pressing my chest against her back, careful not to push all the way into her just yet.

"Time to get fucked like the slut you are!"

She moaned as I pushed my entire length inside her. I placed my hands on her hips and held her in place.

"Guess I over-estimated my size, eh? Seeing how easily you're taking it, it clearly isn't the biggest you've had," I said with a laugh.

I began to pump into her slowly. Soon she was moaning in pleasure as I continued to move my cock in and out of her tight ass. I moved faster and faster, spurred on by how much she seemed to be enjoying what I was doing.

"Ahh... yesss," she moaned, pressing her face into the duvet.

I pushed her onto her stomach. The more she moaned and yelped the harder I fucked her.

"Tell me how much you love my cock you fucking slut!"

"Ohh goddd.....I love your cock, Mr. Winchester," she replied, clenching the duvet tightly with her fists.

I pulled out of her ass.

"Get on your back and get those panties off," I ordered, slapping her ass.

I watched as she did as she was told. I loved the sight of her pulling her panties off. I moved closer and lifted her legs up in the air, giving me a clear view of her asshole. A clear view and access of course. I once again aimed for her sphincter, and again pushed my entire length into her in one go. I grinned as she reached for her hard cock and began to jerk off as I fucked her. She was in complete ecstasy.

"This position is getting a bit boring for my taste. I'm paying you, remember? Time for you to get to work too," I said pulling out of her, before lying down on my back. I didn't have to explain what was expected of her. As soon as I was on my back, she was on top of me, guiding my cock into her well-used asshole with a hungry moan.

"Ooohhhhhh."

I grabbed her ass as she began to bounce up and down on my cock. I smacked both cheeks simultaneously and then grabbed hold of them roughly.

"Ride my cock, slut! Come on! Show me how well you can take that dick!"

She began to jerk off again, all the while riding me. I started to thrust into her, pumping my hips up and down.

"Oh fuck! I'm cumming!" she screamed, as her body quivered.

Thick spurts of cum were spewing from her cock. I began to fuck her like a man possessed, and only stopped when she was finally completely spent. She lifted herself off me, and fell onto the bed.

Sprawled on my back, I heard the heavy breathing of someone who had just been fucked really hard. Finally James opened his eyes, and turned his head towards me. He broke into a smile.

"Oh. My. God!" he said, still trying to catch his breath.

"I take it you enjoyed that?"

"I loved it!"

"I'm happy to hear that. At one point I thought I was being a little too rough. But when I started to shove my cock into your mouth, your eyes told me a different story," I said, stroking his cheek.

"I loved the way you took charge," he said, resting his cheek on my hand.

I grinned and moved over to lie with my chest over his so I could look at him. We began making out passionately, my big dildo rubbing against his spent and flaccid cock.

"So, what do you want to do now?" I asked, after letting go of his bottom lip, which I had been nibbling on.

"I don't know about you, but I am kind of famished and a little tired," he said, stifling a yawn.

"That does not surprise me—you worked up quite an appetite!" I said, grinning. "Do you want to stay in or shall we go out?"

"It would be nice to give Capri, in the Valley a try."

"Then we'd better get ready," I said, jumping off the bed and starting to unbutton my shirt. "I don't need to shower. I think I'll just change into something a little more comfortable. Are you changing?" I asked mock-innocently.

"I think that might be best," he replied, deadpan.

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JAMES's POV

That definitely bagged a place in the top five sexual encounters I've had with Michelle. Just thinking about the whole thing got me hard again, but we're going out, so I guess that will have to wait. And I was starving, and quite looking forward to our date at Capri. Plus, I felt super sexy in the stretch denim skirt with the lace trim which I had paired with a short-sleeved red cotton top. This might seem like a boring choice. But underneath, I was hiding a black silk bra and panty set. Before rushing downstairs to meet 'Mike', I quickly slipped on the black leather three-inch strappy heels I loved wearing with this outfit.

'Mike' was looking very handsome, sitting on the couch absent-mindedly playing with his phone. Like me, he had opted for a casual and relaxed look—a black T-shirt and knee length cargo shorts, with black leather loafers.

"You look gorgeous, babe," he said, getting up after hearing me coming down the stairs.

"Thank you, you're not looking too bad yourself," I said, running my hands from his flat chest—Michelle always wore the binder in character—towards his crotch. I pulled him in for a little kiss to which he responded by squeezing my butt.

"Wasn't that fuck enough for you?" I teased.

"Baby, you look so sexy dressed like that. You must know that it makes me ache for you."

"Yeah? Are you telling me that I light your fire?" I teased, reaching down between our bodies to rub at his crotch.

"You're sooo baaaddd," she said, laughing softly as she leaned in for another kiss.