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.

*-*-*

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.

I giggled and pulled away from him. If we got too carried away, we would never leave!

“So, I was thinking. You didn’t do any shopping for yourself yesterday, so maybe we should hit the shops again today?” he suggested.

“Most of the stores don’t have my sizes,” I reminded him.

“Well, I did a bit of investigating and I think we should check out a store close to the Valley which might just have what you’re looking for.”

“That sounds good to me.” Though to be honest, I didn’t have much hope.

“After, we can head out to Capri and finally grab some lunch,” she said as we locked up and headed out to the car.

The shop was called Curves, and certainly sounded promising. But for a shop assistant who was busily tapping away at the computer behind a counter, the store was practically empty.

‘Mike’ and I had a look around. There were so many clothing options in many different styles. They had everything from cute little tops, jeans and skirts, to formal office wear. The store mostly catered for plus-sized women, but not everything looked big size-wise. It wasn’t long before I found some things that were in the style I preferred. A white knee-length stretch lace dress with coral lining in particular caught my eye. It looked more classy than skimpy.

“I bet you’d look nice in that,” said 'Mike’, whose eye had clearly caught the same dress.

“Should I try it on?”

“We should definitely set it aside for trying on. But let’s add some less casual outfits too.”

“What did you have in mind?” I asked, curious about where her mind was heading.

“Maybe something smart for an evening out. Like for dinner… or a night out at a club.”

“A club?”

“Yeah why not? I can tell that you’re more comfortable about going out in public. I thought that we should go to a nice club sometime. We could have some good fun there, you know,” he said, smiling reassuringly.

“I am more comfortable now, yes. It’s great going out for a nice quiet date at a good restaurant or maybe going to the movies. But clubbing? Why do you want to go clubbing?” I asked.

“Come on, babe. I would love to take you dancing.” He moved in close to me, wrapping his hands around my waist, “I’d like to show off my sexy little kitten, you know.”

“Sexy little kitten, huh?” I couldn’t stifle a laugh at that expression!

“What’s so funny?”

“Who would want to look at me?” I asked shyly. Although, over the years, I had learnt a lot about dressing up and working with make-up, I still thought of myself as a bit unattractive as a woman. Dressing up as ‘Jenny’ was great and knowing that Michelle wanted me as ‘Jenny’ made me fall in love with her all over again every time I’m in character. So, my self-confidence was still not at a point where I felt I could dress up and go to a club where everyone would be sizing everyone else up, looking for hook-ups.

“What are you talking about?” he said, grabbing me. “You look great dressed up—beautiful and striking. Plus, there are so many clubs here in the Valley where people would simply not bat an eye! Remember this part of our lives is about exploration and, most importantly, fun!!”

I looked at him and feigned a smile.

“Please? For me?” he wheedled. He knew that line always got to me. He knew how important making her happy was to me. That line, with that sweet and innocent smile, turned me to putty.

“Okay, okay. You win,” I said, hands held up in the air. “Let’s look around for a suitable outfit. But nothing too revealing, okay?”

His eyes twinkled as he drew me in for a hug and kissed me. He reminded me of a kid who had just been told that he’d be taken to a candy store and could choose whatever treat he wanted! We immediately headed for the more formal section, and began sifting through some club-appropriate garments. I made some selections, and headed for the changing rooms. ‘Mike’ was on a mission and stayed behind, still sifting through the dresses.

The lace dress fit me perfectly and was definitely a keeper. Unfortunately, the other outfits left me a little cold. A red dress that I really liked on its hanger seemed kind of tight on me. Another white and beige dress also didn’t make the grade. ’Mike’ was waiting for me, as I made my way outside the changing room.

“What is all this?” I asked, looking at him standing there with an armful of dresses.

“Try them on, I think you’d look great in practically all of them,” he said, taking the dresses I rejected from me, and shoving his into my arms.

I inspected his choices. Most were really short, and looked like they would barely reach my knees. A couple were much more sophisticated and classy, and would probably end just below my knees. They wouldn’t raise any eyebrows when we were out an about. I preferred to keep a low profile and her choice of dresses would definitely make me stand out in a crowd. I handed the ones that looked too revealing back to him. “No. No. No. No and no,” I said decisively as I rejected each one.

“That’s more than half the stuff I got out for you!” he exclaimed incredulously.

“They are definitely too short and revealing,” I replied businesslike. I would not budge. “But these ones,” I said, nodding towards the ones I had selected, “tick all my boxes. They’re very sexy, and classy.”

“But… but you’d look so sexy in these…” she said, trying to convince me.

“No buts!” I replied coolly as I made my back into the changing room.

I had picked out four dresses from the lot ‘Mike’ had chosen for me to try on. Two were a really good fit and looked fabulous on me. Because it was always so tricky to get outfits for ‘Jenny’ it seemed sensible to get all the dresses I had found looked lovely on me.

Capri was a quaint little place not too far from Curves. The atmosphere was homey, and at that time of the day it was not too busy and crowded. The charming young waiter who greeted us at the door, showed us to a table more or less in the middle of the restaurant.

“I’m Justin and I will be your server today,” he said as he seated us and handed us our menus. “Just let me know whenever you are ready to place your order. In the meantime, may I take your drinks order?”

“I’ll have a lemon iced tea, please,” I said, hoping they’d have it available.

“I’ll have the same,” said ‘Mike’.

After he left our table to get drinks, we studied the menu. I eventually opted for the mushroom risotto, and ‘Mike’ for the chicken fungi.

We sipped our drinks and began chatting about the usual sorts of stuff. The waiter brought our lunch, which looked and smelled absolutely delicious.

“Oh my God, you have to try this risotto,” I said, savoring the first bite.

Michelle leaned over and took a bite from my plate, “You’re right! This could be the best risotto I’ve ever had. Good choice, babe!”

“Your chicken fungi doesn’t look too bad either.”

“It’s lovely actually,” he said, heaping a good-sized serving onto his fork and leaning over to feed it to me.

“Tender.

And the sauce is just creamy enough. Not too rich. Excellent!” I said, taking a sip of the lemon iced-tea we had ordered.

The lovely atmosphere and the delicious food made for a very chilled afternoon. ‘Mike’ and I were just chatting away when I saw a young and rather masculine-looking woman walking in our direction. Her blonde hair was cut short and looked shaggy. Her somewhat masculine but still very lean figure was dressed in a black AC/DC t-shirt and tight fitting black denim jeans. She flashed me a smile as she neared our table.

“Hey,” she said softly, as she brushed me lightly as she passed. I smiled and nodded in her direction, and couldn’t stop myself turning slightly to watch her move towards a table a little behind me.

“What was that?” asked ‘Mike’, grinning slightly. If I didn’t know any better, I could sense a hint of jealousy in his voice.

“What was what?” I said, looking up at him questioningly.

“That ,” she emphasized nodding slightly in the direction the girl had gone. “That ‘hey’, and that smile.”

“What? I was just being nice.”

“You were checking her out,” he said, grinning. He took a bite of the chicken, but didn’t take his eyes off me.

“I was not!”

“You were. You’re getting all defensive because you got caught.” He couldn’t even conceal his amusement now.

“Whatever.”

We ate in silence for a while. Eventually he looked up at me, all smiles. “Why don’t you go talk to her?”

“What?”

“Yeah, go over and talk to her,” he said, putting his fork down and peering into my eyes. I could have sworn he was daring me to go and talk to the girl.

I couldn’t believe it.

“Don’t be such a girl,” he teased. “Besides, maybe we could sandwich you between us,” he said, breaking into soft laughter again.

“What?” ‘Mike’ never ceases to amaze me. “No!”

“Oh come on! Don’t tell me you’re never thought about a little two-on-one action,” he said, lowering his voice suggestively and leaning over to get closer to me.

I continued eating in silence, pretending to be totally ignoring her. But, of course I have thought about it. About ‘Mike’ and some other woman humping me into eternity. I’ve thought about it on many occasions. But Michelle was more than enough woman for me, and I have never seriously considered getting another woman to join us in bed.

“Come on now, I know you’ve thought about it,” ‘Mike’ said now. Clearly he was not going to let this go.

“Maybe,” I admitted, leaning back into my chair and fixing him with a stare.

“I knew it!”

“And now you want to let the rest of the patrons in this restaurant know too?” I retorted drily, eyebrow raised.

He moved his empty plate aside and leaned in closer across the small round table. “I bet you would look sexy with a cock in your mouth while you take one in your ass,” he whispered, his eyes not leaving mine.

“Could we drop this, please?” I asked, feeling uncomfortable and a little annoyed.

“No. I think we should talk about it now,” he said, with a teasing twinkle in his eye. I knew that look—this conversation was exciting ‘Mike’.

“This is hardly the place,” I said, looking around to see if anyone might be listening to this sordid conversation.

“It’s as good a place as any,” ‘Mike’ replied. He sounded almost demanding. Clearly he was not going to let this go at all.

“No!” I replied, being equally insistent.

“Okay. But at least tell me what you’ve thought about,” he asked, changing tact.

“Fine,” I said, surrendering. “I sometimes fantasize about me with you and another woman dressed like that.”

“Well, that’s a bit vague. Your fantasy must be more detailed. Come on. It’s me,” he said with an encouraging wink.

“Well obviously she is feminine like Michelle, but good at pretending to be masculine when the situation demands it,” I explained, moving my plate to the side too and leaning on my elbows, looking at ‘Mike’. I could almost see his imagination churning away.

“Okay. I’m just playing around with an idea, so don’t become all alarmed now,” he said looking straight at me. “Would Carmen fit the description?”

I was silent for a while, trying to figure out who she was talking about. Then the penny dropped.

“That girl from the adult store we visited yesterday?” I asked, incredulous.

“You remember her!”

“Well, we just met her yesterday. Why did you think of her all of a sudden?” Like Michelle, ‘Mike’ never just has an idea. I was a little suspicious.

“Just like that” Clearly he was not going to give anything away.

“Well, it’s just a fantasy,” I said. “I certainly don’t expect you to invite anyone else into our bed. We’re doing fine by ourselves.”

“I know, babe,” he said, softly squeezing my hand.

“Speaking of fantasies, what have you got planned for tonight?” I asked now, eager to change the topic.

“You’ll just have to wait and see,” he teased, stroking my palm with his thumb and not breaking eye contact.

“Well, that’s not fair. I told you about this threesome thing. The least you can do is to tell me what you have planned for tonight?”

“Okay,” he replied, looking at me warily. “Don’t freak out but I kind of want you to dress up like a hooker for me,” he said in a rush, before taking a sip of his drink and looking up at me, waiting for my response.

“You want me to do what?” I gasped, shocked.

“I want you to dress up like a hooker for me. We can role-play it. I’ll pick you up on a street corner and…”

“Whoa, whoa, whoa,” I said, raising my hands and gesturing for him to stop.” What is this about me standing on a street corner so that you can pick me up like I’m a hooker?” Yes, we were quite adventurous, but this was starting to scare me. I’d be the one standing on that street corner!

“I mean, I’ll drop you off at a street corner, drive around the block, and pick you up there again. It’ll be a role-play, like this morning. You enjoyed that.”

I was speechless. What he suggested sounded risky, not to mention dangerous. What happened that morning happened in the safety of our home. What we’re talking about now was something else.

“It could be really hot, babe.”

“I don’t think so.” I sat back and looked him in the eye.

“Please. Please, please, please!” he begged, all puppy-dog eyes again. But I won’t be so easily convinced this time.

“I don’t think so.”

“Oh, okay,” he said, disappointment clear on his face.

The topic had dealt our pleasurable outing a fatal blow. We sat quietly for the remainder of the meal, and drove home in silence. Hell, we hardly spoke for the remainder of the day. Back at home, Michelle crashed on the couch in front of the TV, and stayed there for most of the afternoon. I took care of some office work first, and then some chores around the house while she barely moved from the couch. The silence became deafening. We even had dinner in virtual silence.

After I had cleared the dinner table, Michelle immediately headed back to the living room. This was just too much. I couldn’t allow it to go on for any longer. I headed to the living room, and sat down next to her.

“So, can I atleast see this outfit?” I asked gingerly, testing the waters.

“What’s the point, you won’t do it,” she said sulkily, flipping through the channels.

“I’ll do it,” I finally said, dejectedly. Her face lit up immediately. She stared at me incredulously, grinning from ear to ear.

“You will?”

“I will, but I want to see what you want me to wear.”

“It’s upstairs.” Her excitement was palpable.

“Well, let’s go see it.”

She leaned over and kissed me on the cheek before taking my hand and leading me up the stairs.

In the bedroom, I opened the bag she handed to me. Well this would be a first. I had never before worn a halter top, much less a golden one. A tiny leopard print mini skirt, a shiny thick black belt, black fishnet stockings and a pair of rather sleazy high heel sandals completed the costume.

“This skirt seems fitting, but far shorter and skimpier than anything I’ve ever worn in public,” I said rather sternly, as I settled on the bed the garments spread out before me.

“Babe, we did your surprise thing this morning,” she reminded me gently. “Now it’s my turn. Besides, we agreed that we would fulfill each other’s fantasies. I stuck to my end of the bargain.”

“I know. But bear in mind that we played in the safety of our home this morning,” I reminded her. “Plus, to be fair and given its nature, we should have discussed the pros and cons of your fantasy before you settled on it so firmly.”

Her face dropped again.

“Okay, if you don’t want to do it, it’s fine,” she said, sulking again.

She was obviously manipulating me emotionally. I never know what to do when she is like this. What she was suggesting was risqué at best and downright dangerous at worst. What if other men approached me while she was driving around the block! What about the cops!

“Honey, I just think that it is way too risky to stand on a street corner dressed like that and pretending to be a hooker. What if the cops come and things get out of hand?” I asked, hoping that she would be reasonable.

“I had thought about it. And the area I have in mind is pretty safe. But if you’d rather not, we can forget about it.” More sulking.

“Okay. Fine, I’ll do it,” I sighed, relenting. I couldn’t stand the idea of her sulking like this for God knows how long.

“You will?” The smile was back now, and the sulking over.

“Yes, but only if we go to a safe place, and only if I don’t have to stand there for more than a few minutes.”

“Don’t worry. Everything will be okay. I won’t do anything that places you at risk. You should know that.”

“Okay.” I was still incredibly nervous about the whole thing.

She moved to stand between my legs where I sat on the bed. She bent down to give me a kiss.

“So… shall we get ready?” She couldn’t even conceal her excitement.

An hour later I looked like a cheap and slutty whore. Michelle did my make-up this time, and she wasn’t aiming for subtlety. I hardly recognized myself, when I looked at what she had done. The scarlet lips said it all. I was a whore.

“Slutty.” she said almost to herself, as she looked me up and down.

“You’re enjoying this a little too much, aren’t you?” I asked, frowning a little.

“Oh babe, I’m just teasing,” she said, wrapping her arms around me comfortingly.

It was 11 P.M. by the time we headed out to the car.

‘Mike’ was wearing a plain white T-shirt with blue denim cut-off jeans and a leather jacket. Before she got dressed, Michelle had strapped on her new Joque harness before attaching the new 9-inch Outlaw dildo to it. The size made me nervous, but judging by the wicked grin she had on her face when she strapped it on, excited her very much. ‘Mike’ was going commando tonight.

We were heading towards the Valley again. ‘Mike’ took an exit to a neighborhood of townhouses. It looked pretty quiet and peaceful. He brought the car to a halt and parked near an old convenience store which, at 11:30 p.m. was closed.

“Stay here while a take a look around outside, okay? I’ll be right back,” he said, getting out of the car.

Once ‘Mike’ had returned and gotten back into the car, I took a deep breath, unlocked the car door and stepped out onto the sidewalk. He lowered the passenger window, and peered at me. “Don’t be nervous. It’s late and I don’t think anybody will spot you. You will be fine. Just remember, stay in character no matter what, okay?”

I nodded, and crossed the road slowly, still looking around carefully, in case someone else was out at this time of the night. I selected a spot that wasn’t as well-lit as some of the other parts of the road. I felt a little safer in the shadows. My mind was racing and I felt my heart beating like a drum inside my chest

‘Mike’ drove off, and I was left all alone. I was nervous as hell, but must admit that there was a small part of me that was beginning to feel excited. I have fantasized about being used by ‘Mike’ like I was a whore, but had never told Michelle about it. Now these fantasies were about to come alive.

After checking my watch for the third time, I realized that fifteen minutes had gone by. The car was nowhere in sight. Worry was starting to creep in, and I pulled out my phone to text ‘Mike’. He replied saying that he had taken a wrong turn and gotten a bit lost. He promised to be back soon. Another fifteen minutes went by before I finally spotted the car. “Thank God!” I thought.

I straightened up, feeling somewhat safer and somewhat more confident. I started walking towards the car, strutting sexily. I walked over to the driver’s side and peered into the tinted windows. I rapped on the driver’s window. ‘Mike’ rolled down the window and smiled at me.

“Hey sugar, you looking for a date?” I asked in a sexy voice.

“Yeah. Sure, how much?” he asked, grinning.

“Depends.”

“On?”

“On what you would like tonight, baby.”

He reached over to the console and lowered the window behind him.

“Well, how much would it cost to entertain two of us?” he asked with a grin.

I froze. I peered through the window at the seat behind her. Carmen, the girl from the sex store we visited the day before, smiled up at me. She winked. I was completely taken by surprise. I didn’t know how to react. I looked at ‘Mike’, wanting some sort of explanation. He just smiled.

“Go along with it,” he said, hoping to reassure me.

So this was why the threesome and Carmen came up earlier that day. He had been thinking about this all along.

Although I was taken by surprise, the thought of a threesome with the two of them was really exciting. I took a closer look at Carmen. Like Michelle she was dressed like a man. She had on a tight black tank top over which she wore an open red shirt. Even though she was seated and it was quite dark, I imagined that her black jeans were skintight.

“So? Are you game?” ‘Mike’ asked .

I wasn’t sure whether ‘Mike’ was talking to ‘Jenny’ the whore, or to James.

I straightened up and decided to just roll with it. Hell, I had fantasized about this a bunch of times and clearly Michelle seemed to want to do it as well. So I held my head high and added a touch of attitude to my persona. “Since there are two of you, it’ll be $200.”

“Make it $150 and you can get in,” ‘Mike’ answered somewhat impatiently.

I raised an eyebrow, pretending that I wasn’t interested.

“Come on baby, my friend just got into town and I promised him a good time.”

Carmen moved a little closer to the window. “Yeah sugar, come on. We’ll show you a good time.”

“Okay, but I want to get paid first,” I said, all business-like.

‘Mike’ handed me the money, and I slipped it into my purse. I walked around the car and got in next to Carmen. As we drove off, Carmen moved a little closer.

We stopped at a traffic light and I saw ‘Mike’ peering at me in the rearview mirror. “I’m Mike and this is my friend Carlos.”

“Nice to meet you,” I said smiling at ‘Carlos’

“Damn ‘Mike’, you picked up a good one.”

I smiled and ‘Carlos’ moved even closer to me. He put an arm around me, and started to caress my thigh with the other. I ran my hands up his thigh, moving it all the way to his crotch. The bulge in his pants took my breath away. I looked in the rearview mirror. ‘Mike’ was smiling.

“Say, why don’t you guys get this party started, while I drive?” he said, peering at us in the mirror.

I looked over at ‘Carlos’. He looked at me questioningly. Damn, he was sexy. I certainly did want to get the party started. I moved in even closer.

I was enthralled as I watched ‘Carlos’ unzip his pants and pull out his big black cock. It looked very familiar, very similar to the one I knew ‘Mike’ had hidden away in his pants. ‘Carlos’ smiled at me and began stroking himself.

“You can take it in your mouth, sweetie,” he said, after a while.

I took his cock in my hand. I felt its weight and closed my fingers around it. I leaned over towards his crotch and took the head into my mouth. I began sucking on it, sucking on a complete stranger’s cock. This was only the second cock I had ever blown.

“That’s nice, honey,” he sighed, starting to caress my shoulder encouragingly. I loved that he loved what I was doing and sucked him even deeper, almost gagging.

“That’s it baby girl, suck his big dick,” said ‘Mike’, clearly enjoying the show.

I continued to stroke and lick his lovely big black cock. I traced my tongue all the way from the base to the head.

“You do it like a pro, sweetie,” said ‘Carlos’, laughing softly. I could only mumble a ‘thank you’ as I continued to earn the money they’d paid me.

“So, where should we take her ‘Mike’?” asked ‘Carlos’ after a while, his hand stroking my hair absent-mindedly.

“I know this little motel not too far from here. We can get a room and continue the party there.”

Their talk was getting me excited. My cock was hard inside my panties

We had been driving around for what seemed like quite a while, but could really only have been ten minutes, when ‘Mike’ finally parked the car.

“We’re here,” he said, as he got out of the car. For the first time I saw the small fanny pack he had with him.

I straightened up, and looked out of the window. The motel looked cheap and sleazy, the kind of place guys took hookers to. ‘Carlos’ still had his cock out and was stroking it. He smiled at me wickedly. After a few seconds he got out of the car too. His cock was still out! I couldn’t take my eyes off it as he reached his hand into the car to help me out.

The area around the motel was dark, which added to the sleazy atmosphere. ‘Carlos’ pulled me closer as the three of us walked towards reception. He grabbed my ass as ‘Mike’ approached the desk.

The place looked deserted. It was definitely not clean either. The young man at the desk looked like he was in his early twenties.

“Could we get a room, please?” asked ‘Mike’.

The young man looked at us, and got up. ‘Carlos’ immediately pulled me close, and began kissing me. He hiked up my skirt a little, to caress my ass, while grabbing one of my hands and putting it on his still-exposed cock.

“Stroke my dick, baby. Keep it hard,” he whispered in my ear.

I returned his kiss and began to stroke his big cock. He pulled away after a few seconds but continued to grope me while I continued to jerk him off. The poor boy’s jaw had dropped. ‘Mike’ turned around to see what it was that had caught his attention. He grinned at us before turning back to the blushing young man.

“Sorry, my friends are a little horny,” he said, without batting an eye. “So? The room? Please.”

“It’ll be $20,” the young man stuttered.

‘Mike’ paid and was handed a key. The young man kept his eyes on ‘Carlos’ and I throughout the entire transaction.

‘Mike’ came over to us, smiling and slapped my ass. “Let’s go, baby girl.”

We didn’t even reach the room. Halfway there, ‘Mike’ grabbed me and pinned me against the wall. I couldn’t believe it. Right there in the filthy hall! He unzipped his fly, and freed the beast I had been thinking about earlier.

“Why don’t you give my cock some attention now, baby,” he said, pushing me to my knees on the filthy carpet.

I began to stroke him. After a while I finally took his cock into my mouth. I kept sucking on it feeling like a true whore. ‘Carlos’ couldn’t keep his eyes off the scene. Soon he began to stroke his cock too.

“That’s it, baby,” said ‘Mike’, encouraging both of us it seemed.

‘Carlos’ moved closer to me and began to gently slap my face with his dick.

“She’s a real fucking slut, this one,” he said, laughing.

“I like sluts who do as they’re told,” said ‘Mike’. He pulled out of my mouth, and began to smack his dick across my face too. All I could do was stay on my knees, helplessly taking what they were giving me.

“Let’s see how far you can take it, baby,” said ‘Mike’, grabbing my head and forcing his cock into my mouth. Soon I began to choke on his dick. Eventually, he released me so I could come up for air.

“Dude, I’m so fucking horny. Let’s just go to the room and fuck the shit out of her,” said ‘Carlos’.

‘Mike’ pulled me to my feet and we started moving again. As soon as we were in the room I was pushed to my knees once again. Soon their cocks were poking at my face again. I began to suck and stroke ‘Carlos’ while ‘Mike’ jerked his own dick.

“Oh fuck yeah, you like that, baby,” ‘Carlos’ moaned as I plied my trade.

“Come on now, don’t be hogging my friend’s dick. I need some attention here too, baby,” said ‘Mike’ moving closer to me.

I switched to his cock, while jerking ‘Carlos’ with my hand. I was servicing them like a hooker who was good at her job. Soon I was moaning too.

“Looks like she’s really hungry for it,” said ‘Carlos’, laughing.

“Yeah, baby, take that cock down your throat. Jerk it, baby,” ‘Mike’ shouted.

In no time I was alternating between sucking ‘Carlos’ and ‘Mike’. Every time I took ‘Carlos’ in my mouth she force-fucked my mouth in the same way ‘Mike’ had earlier.

“So, who wants a go first?” I asked after a while, smiling mischieviously.

“Someone is eager for cock,” said ‘Mike’. “I think I’ll let my buddy here go first.”

They pulled me up to my feet, walked me to the bed and pushed me down on my back. I watched as they stripped down to their binders and strap-ons. ‘Mike’ got onto the bed next to me and pushed his cock into my mouth, while ‘Carlos’ hiked up my skirt and pulled my panties down.

“Lube’s in here,” said ‘Mike’ throwing the fanny pack towards ‘Carlos’. In a flash he had found the lube and was applying it to my asshole. He started with just one finger and then slowly introduced a second and then a third. I had never taken three fingers before and it felt somewhat uncomfortable. Their cocks were quite huge and I needed some good foreplay to stretch me out before I took those monsters.

“You ready for me, baby?” asked ‘Carlos’ after a while.

I nodded.

He lifted my leg onto his shoulder and aimed his cock towards my hole. He pressed a little harder as my ass slowly gave way. The head went inside and he slowly began to insert his entire cock. I winced in pain—the cock was the largest I had ever had. ‘Carlos’ continued to push. ‘Mike’ held me in place, still fucking my throat. I felt the entire length of the cock entering my hole. ‘Carlos’ slowly pulled out and pushed in again a few times, helping me to get used to the length and girth. Once his whole length was inside me, he stayed in place for a few minutes. Then he began to fuck me.

‘Mike’ continued his assault on my mouth. I was gagging on his cock while ‘Carlos’ worked my ass over.

“Fuckkk… oh my God!” I screamed as the sensations took over.

“Yeah, that’s it slut, take my cock,” grunted ‘Carlos’.

“Do you like that, baby? That big dick inside you?” asked ‘Mike’.

“Yes! Yes! I love it!” I almost screamed my reply.

“My turn now,” said ‘Mike’ as he flipped me over. I could hear the cock flopping out of my ass. I got on my hands and knees as ‘Mike’ lubed up his cock and pushed it inside me. ‘Carlos’ didn’t waste any time, and soon his cock was in my mouth. I had never tried ass-to-mouth before. This certainly was a night of firsts! His cock tasted a little musky. But I had been paid, and I that meant I had to keep blowing him.

‘Mike’ grabbed my hips and began to pound into me really hard. Soon he was also spanking me.

“Ohhh… fuck... fuck… fuck…” I moaned, grabbing hold of the cock in my mouth, and jerking it off wildly.

“That’s it. Take it bitch. Take my big dick,” grunted ‘Mike’.

“Oh fuck yeah, baby, you like that? Yeah!” moaned ‘Carlos’.

“She does, doesn’t she? She can’t get enough,” said ‘Mike’.

“Is that right, slut? Can’t get enough of cock, can ya?” asked ‘Carlos’.

“I want more…” I managed to say, mouth and ass still filled to the max.

“Yeah, that’s right, suck that cock, baby girl,” said ‘Carlos’.

I was in heaven! Here I was, dressed like a hooker, in a cheap sleazy motel, getting fucked like a cock loving bitch and it was glorious!

“Time to ride some dick,” said ‘Carlos’.

‘Mike’ pulled out of me as I got on top of ‘Carlos’ who was on his back on the bed. I guided his cock into my hole and began to ride him. ‘Mike’ stood up and shoved his cock into my mouth. I began to suck on him, sucking my ass juices of his cock. ‘Carlos’ started to smack my ass as I rode him enthusiastically while ‘Mike’ slapped his dick on my face.

I was enjoying everything they were throwing at me. ‘Carlos’ once again began to jerk me off. Huge waves of pleasure were coursing through my body. I loved being dominated in this way.

“I want you to ride my cock now, baby girl,” said ‘Mike’.

They swapped places. This time I was atop 'Mike’. ‘Carlos’ jerked his cock off in front of my face, as ‘Mike’ began to stroke me, his movements faster and faster. He could tell I was nearing my orgasm.

“Fuck! I’m cumming!” I screamed.

I began to spray cum all over ‘Mike’ and the bed. I felt like I was cumming for an eternity all the while riding ‘Mike’. When I was spent, I collapsed on top of him.

After quite a few minutes, I looked around and saw both Michelle and Carmen grinning at me. Carmen was the first to speak.

“Fuck, that was so hot!” she said, grinning from ear to ear.

“Oh my God! It was!” I said, sweeping sweat off my brow.

“Did you like getting fucked by two cocks?” asked Michelle.

“Oh my God, you have no idea!”

Michelle laughed, “I knew you’d like it.”

“But how did you manage to plan all this?” I asked.

“Well, when I went in to buy your costume, I got talking to Carmen. She said she had pegged guys before and she was game for a threesome!

“How could I not be up for it? It was so hot to hear that you might dress up like a hooker, I just couldn’t say no!” quipped Carmen.

“So, this was all preplanned?”

“Yeah, but you enjoyed it, didn’t you?” asked Michelle.

“I enjoyed all of it!”

“Good. So maybe you wouldn’t mind if Carmen spent the day with us tomorrow?” asked Michelle.

I smiled, thinking of all of the possibilities the next day could bring.

*-*-*
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.

*-*-*

CHARACTERS:

James Winchester / Jenny

Michelle Winchester / Mike

Carmen 

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

*-*-*
I hope you enjoyed this part. I have finished writing another chapter as well, but I am still trying to make it a little better and I will hopefully release it soon. Please do comment or write to me if you liked this story at .

Alternatively, I have a new story series plan for ‘Jenny’ with Michelle and I need some people as a soundboard to see if that particular storyline sounds interesting. I would love to hear thoughts from readers who are into this genre and can give some feedback on this new story idea that I have. You can email me for the same at .

Until then happy reading and happy fapping!