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'Jenny' & 'Mike': Romance & Threesomes

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This is the fourth chapter in the 'Jenny' & 'Mike' series. If you haven't read the earlier chapters, then you may do so by clicking on my profile and reading them. They are listed in the following order:

  1. 'Jenny' & 'Mike': Date Night
  2. 'Jenny' & 'Mike': A Day Out
  3. 'Jenny' & 'Mike': Fantasy Sunday

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CHARACTERS:

James Winchester / Jenny

Michelle Winchester / Mike

NOTE: This story is written from James' POV

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It was close to 10 a.m. and I was still in bed with Michelle sleeping peacefully next to me. Last night had taken quite a bit out of me. Having been used and fucked by two cocks was a huge turn-on. 'Mike' and 'Carlos' had given me quite a workout! I received the fucking of a lifetime. Sex with Michelle had always been great, but having a third person added a totally different edge. The only thing I regretted was that Michelle didn't cum. Although Michelle had had a great time too, it had all been about my pleasure. I was determined to show my gratitude.

I snuggled up to her where she was still sleeping with her back to me. I moved closer, and planted a gentle kiss on her shoulder.

"Mmmmmm. It's early," she groaned, objecting slightly.

I paid no heed and continued my kissing, my lips now moving up to her nape. Half awake now, Michelle turned around to face me. I smiled and gave her a gentle kiss on her lips.

I ran my hand up on the side of her leg, rubbing and caressing her. I pushed her onto her back and got on top of her. I knew I had her attention when I saw the longing in her eyes.

I kissed her again, this time more deeply, making my intentions abundantly clear. Michelle snaked her arms around my back, running her hands over my bare back and pulling me in close.

I moved my hands up between her legs. She let out a moan as my hand made contact. My fingers continued to tease her as our sensual kiss continued.

I moved my hand into her boxer shorts and began teasing her clit. She gasped as my fingers made contact with her sensitive little button. I broke our kiss, and looked into her eyes.

Michelle pulled away and sat up a little to take off her tank top and release her breasts. Her action forced me to release her pussy. God I loved her tits. I sat up too and leaned in closer so that I could cup them in my hands. She moaned as I played with her nipples, pinching them slightly to cause a little pain.

After a little while of this gentle teasing, I positioned myself on top of her again and we began kissing again. I continued to squeeze her breasts, loving how hard her nipples were becoming. She was clearly getting turned on.

I took her right nipple into my mouth and gave it a few licks. Her moans grew louder. I turned my attention to the left one, eliciting more moans. I continued sucking her hard nipples while my hand returned to her pussy. This time she opened her legs, spreading them a little wider giving me better access to her wet snatch.

She sighed as I spread her lips, and slowly inserted a finger. I pushed it in to the hilt, loving the way she clenched around it. I began to massage her clit with my thumb, all the while fucking her with my finger. Michelle was panting rapidly by now. I released the nipple I was sucking on, and started kissing her neck. I pulled my finger out of her pussy and ran my fingers up her belly towards the nipples my mouth had just released. I squeezed her breasts and pinched her nipples as I slowly planted kisses from her neck to her breasts, all the way down her abdomen, finally reaching her pussy lips.

She ran her hands through my hair. Her eyes darkened with desire—she knew what was coming. My tongue flicked her clit gently, just once. She shuddered at the contact; I had her just where I wanted her. I began to lick her clit harder and faster. I let go of her breasts, and inserted two fingers inside her love tunnel. Her moaning grew even louder. She spread her arms out wide on the bed, and grabbed the sheets tightly. I continued to pleasure her—my tongue on her clit, and my fingers in her cunt. Within just a few minutes she let out a loud groan and soaked my hands with her pussy juices.

I have always loved how responsive she is during any form of sexual activity. I lapped up her juices enthusiastically with her shuddering each time my tongue touched her sensitive lips and clit.

Her hands relaxed and released the sheets as her orgasm neared its end. But I was not done with her yet. I grabbed her thighs forcing them wider, and latched onto her pussy with my mouth again. I licked her box with the same fervor as before. She arched her back, writhing and gasping. She was thrashing around so wildly I had to increase my grip on her thighs to keep her down. Her breathing became more rapid as yet another orgasm hit her. This time she let out a scream, louder than the first groan, her whole body shaking with her release.

I let go of her legs and gave her pussy a few final licks, before straightening up and sitting up in bed next to her. She finally opened her eyes, but still hadn't caught her breath.

I grinned at her, before moving in for a deep and passionate kiss. I knew she could smell and taste herself on me. It was hot and really kinky.

"What was that for?" she asked with a huge smile.

"I kinda felt bad that yesterday was all about me. I wanted to make up for it."

"Hell of a way to wake up," she said, still grinning. "I could get used to it."

She pulled me back towards her for another kiss. She eventually broke the kiss to look up at me lovingly.

"We have to get up," she said, stroking my cheek.

"We can stay in bed for a little longer," I said, with a mischievous grin.

"Have you forgotten that we have a guest coming over today?"

Things were so hazy after the fucking I got last night that I had completely forgotten that Carmen would be spending the day with us.

We had wanted her to come home with us last night already, but she'd declined.

"I forgot about that," I admitted, grinning.

"Yes, you did," Michelle said, giggling.

"Last night was so much fun," I said, grinning from ear to ear.

"I know! I was there, remember? You know, doing the fucking..." she said, breaking out into laughter.

"You know what I mean. Until now, it has always been just you and I. We have invited a third person into our sex play, now. I..."

"Shh! Babe, I love you. I love everything about you, but I want us to explore every part of this new path we've embarked upon. I don't want us to shut the door we've just opened. But I do want you to be comfortable."

"You mean us..." I began.

"Yeah, we're in this together. I love to be the one on top. I love to be the one in control. I found that out very early on in this journey. I would love for us to explore this a little more."

"More?" I asked.

"Well, until recently, we only ever had sex in the bedroom, or in the comfort and privacy of our own home. We've had sex in a public place now. Like you said, it used to be just you and I. Last night we had a threesome. We role-played with another person. Having a playmate might be a good thing," Michelle said, taking my hand.

I sat up straighter, silent. Inviting Carmen to be our playmate was fine, but what if Michelle began to experiment with her? I mean, I had always thought of two women having sex with each other as a major turn on, but what if Michelle decides she likes it better? Or worse, what if Michelle decided to introduce another man?

"What's wrong?" Michelle asked now, seeing how thoughtful I'd become.

I didn't know how to explain how I felt. I struggled to find the words.

Michelle got onto her knees on the mattress next to me. She reached for me and held my face between her palms, looking into my eyes.

"What's wrong?"

"Do... do you want to experiment with her?" I asked, searching her eyes for a clue.

She gave me a funny look, eyebrow raised. Then she burst out laughing.

"Is that what's worrying you? That she'll steal me away?" she asked, doing her best to contain her amusement.

"No... I don't know... I... I guess I'm just... worried that..." I stammered.

"That what?"

"... that you might like women better and might not want me anymore..." I said in a rush.

"Why would you think that?" she asked, quieter now.

"I don't know. You like it when I dress up as 'Jenny'. You even like to fuck me when I am 'Jenny'. I guess I thought maybe you liked it because you might prefer women," I confessed.

"You're forgetting that I like to dress up as a guy and have sex with you while you're dressed as 'Jenny'. Plus, I love you. Yes, I like to fuck 'Jenny', but that's only because you are 'Jenny'," she said, holding my hand and stroking my shoulders gently.

"What if you decide to... to bring a man into bed with us?" I asked.

"Do you want that?" she asked, clearly surprised.

"No. I don't. I mean, this is as far as I know I can go. But..." she stopped me again, with a shake of her head.

"Babe, you are mine and I am yours. I would never push you into doing something you didn't want to do. I have always known that pegging is as far as this is going. Which is why I have never brought up bringing another man into the equation."

"So... you don't want to experiment with another woman or another man?"

"Honestly, I tried experimenting with women in college a few times, and I did enjoy it. But I am with you. I don't need anyone else. You are all the woman I need. And all the man I could ever want. I found the best of both worlds in you, babe." She leaned in, pressing her forehead against mine.

I admit that I felt relieved. I now knew that even though we were trying something new, she still wanted me, and that I was enough for her. I pulled her in for a tight hug.

"I love you," I said, as I pulled away to look deep into her eyes.

"I love you too, babe," she whispered, gently.

Half an hour later, I was downstairs brewing coffee while Michelle took a little nap. When she walked into the kitchen, she looked pretty dejected. What had happened to the loved-up girl I'd left upstairs?

"What going on?"

"I just spoke to Carmen. She can't get out of her shift at the shop. Someone might be able to stand-in for her from about 1 p.m. She'll call us to let us know whether she'll be able to get away."

She put her phone down on the table, and sat down. Her disappointment was obvious.

"It's okay, babe. As you said, she might still be able to join us. And if she can't, well, there's still 'Mike' and 'Jenny'," I said with a wink, trying to cheer her up.

"Yeah... I guess," she said, not sounding any less disappointed than before.

"So, what do you want to do now that since Carmen isn't going to meet us until later?" I asked as we sat down to a breakfast of French toast.

"I don't know. I had kind of thought that the three of us could hang out here and get to know each other better. Or maybe we could go out for a picnic or something," she said, nibbling on her toast.

"That's a good idea. We could even go alone -- just you and I."

"Yeah?" she asked, appearing to be coming around to the possibly of Carmen not being able to join us as planned.

"It could be fun."

She smiled as she looked up at me. "You seem very excited by the idea!"

"I am! The weather's great and what could be better than spending some time in nature? Where should we go?" I mused aloud.

"How about Green Grove?" she suggested, pushing her empty plate to the middle of the table, and leaning on her folded arms.

Green Grove was a national park about an hour or so away from where we lived. It was a beautiful place for camping, picnics and barbeques. It catered to families, couples and individuals who wanted to spend some quiet time in the outdoors.

"That settles it," I said, as I got up to clear the table.

At 11:30 a.m., after a quick shared shower, we hit the road with our picnic basket. 'Mike' looked very outdoorsy in a pair of green chinos, a white t-shirt and hiking boots. I had watched hungrily when Michelle strapped on the eight-inch cock, which was now tucked inside 'Mike's' boxers. For 'Jenny' I had chosen a pink summer dress, a white sweater and some comfortable slippers. The matching pink cotton bra and panties I wore underneath felt lovely and cool on my skin.

We laughed and talked for the entire relaxing drive to Green Grove. We found an ideal picnic spot near the lake. One of the two nearby picnic tables was occupied by a family of five. We got out of the car and headed for the second one.

"I had hoped to find a nice private spot somewhere around here," 'Mike' said quietly as walked towards the picnic table.

I was quite taken by surprise when he suddenly grabbed my hand and led me further along a path, though some trees until we found a trail. After about fifteen minutes of gentle strolling, we came across a secluded spot, still quite near the lake.

"This looks much better," 'Mike' said with a sly grin. "Nice and green, peaceful and secluded."

We opened the blanket and spread it out under a nearby tree and not too far from the water's edge.

"It really is such a beautiful day," I said, settling on the blanket and starting to unpack our lunch.

"It is, isn't it?" said 'Mike', opening the cheese and ham sandwiches we had packed, and putting them on a plastic plate. I opened the sparkling apple juice and plastic glasses, and poured each of us a refreshing glass.

It had been quite a while since we had been on a picnic, and we spent a long while just eating in silence and enjoying the surroundings. "This really was a good idea, you know," I said as I packed away the plastic plates and glasses. I scooted next to 'Mike' and leaned my head on his shoulder. Right on cue, he placed his arm around my waist pulling me nearer. We sat listening to the birds and admired the calm lake surrounded by the blue-green trees, bushes and grass surrounding it.

"Thank you," I said, quietly after a few minutes.

"For what?" 'Mike' asked, turning towards me.

"For all this," I replied.

"Well, if I'm not going to take care of my princess, then who will?"

He bent down towards me and gave me a quick kiss.

"How about some of the apples I packed?" I asked, reaching for the green globes and the pocket knife we had packed. I settled back and started cutting pieces and feeding them to 'Mike'.

"Mmm, these are nice," he said, smiling. "You should have some too."

I popped a piece in my mouth, and spat it out almost immediately. "It's pretty tart, you know! How are you managing to eat it?"

'Mike' chuckled at the face I was making.

"Maybe you're just too sweet for them?" he retorted, giving me a naughty smile.

I couldn't hide my blush. "Am I, now?"

"I think you're too sweet," he said, smiling.

His compliment had me feeling quite shy. I self-consciously pushed a lock of my hair behind my ear.

"You really don't like it?" 'Mike' asked.

I shook my head and he immediately grabbed it from my hand and tossed it into the small plastic bag we had brought along for any debris left over from our picnic. The pocket knife also went back into the basket. "There. All gone," he said with a grin before pulling me nearer.

"You look so pretty today," he said, running his hand through my hair.

He gave me that look that always made me weak in the knees. Soon he was caressing my face while I looked dreamily into his eyes. His hand made its way up towards my chest to squeeze my tit.

"Umm, maybe we shouldn't do this here," I said, a little nervously.

"You're getting shy on me after everything we did last night?" he asked, grinning.

"No... it's just... what if someone walks by?" I stammered.

"Don't worry, no one will come. We're not going to be disturbed," he said, resuming fondling my breast.

His attention relaxed me and in no time we were making out like teenagers. 'Mike' ran his hands up under my dress to caress my thighs. He gradually moved his hands upwards. By this time my erection had filled my panties. As soon as he reached my crotch he could tell the effect he was having on me. He wasted no time, and started massaging my cock through my panties.

"God, you're so fucking sexy," he whispered.

He got on his knees behind me, and began to grope my tits with both of his hands. I was sorry that he was no longer paying attention to what was between my legs, but enjoyed the sensation of having my tits man-handled in that way.

As things got more heated, 'Mike' turned me around so that I was facing him. He began unbuttoning my sweater. His hands were roaming over my body, while he planted gentle kisses on my shoulders and neck. His hands once again found their way to my hemline. He pulled it up slowly. Soon my thighs and panty-covered cock were completely exposed. He pulled my cock out of my panties and began to gently stroke it, all the while continuing to shower me with kisses.

I began to moan and whimper as he continued teasing me. 'Mike' taking control in this way, made me feel like a real woman, a woman who wanted to please her man. Finally, I heard him unzipping his chinos. I watched as he pulled out his cock and began stroking it.

"I'm so hard for you, baby," he said, getting upon onto his feet, but not taking his hand off his cock.

I got on my knees now too, my face directly in front of his crotch and his stiff cock. I leaned forward and gave it a quick lick.

"Take it in your mouth sweetie," he directed.

I didn't need to be told twice. I placed my hands on his hips and pulled him nearer. I took his cock into my mouth and began working it in and out of my mouth. I licked the head for a while before running my tongue all along the length of the shaft.

He took my chin in his hand as I sucked him off.

"Baby, you look so good with my cock in your mouth."

I looked up into his eyes and continued to suck his dick. He grabbed my head and slowly began to fuck my mouth. Being used in the outdoors like that felt amazing.

I was taken by surprise when 'Mike' pulled his cock out of my mouth. He winked at me and reached for his backpack, which was lying next to the picnic basket. I knew what came next. I bent over on my hands and knees. I watched him take a bottle of lube out of the backpack, and apply a few drops to his cock. He kept stroking it.

"You've come prepared," I observed, drily.

"Always," he said, giving me that now familiar mischievous grin. "Take your panties off."

I stayed on my knees and slowly slipped my panties over my ass and thighs. When it got to my knees I maneuvered it over first one knee and then the other. Then, with a few more quick movements, I slipped it off completely. With my ass completely bare now, I smiled up at 'Mike' playfully, and reached for his cock. I loved how slick it felt as my hand moved up and down on it.

"Lay down on your side, naughty girl," he ordered.

I hiked up my dress, and lay down as instructed. I let out a short shriek when he applied a good amount of lube to my asshole. I moaned as I felt him inserting a finger into my ass.

"Does that feel good, baby?"

"Ohhh... yes very good."

"Do you want my cock inside you?" he asked, in a strained whisper.

"Yes, baby. I just don't want us to get caught," I pleaded. I was very turned on, but my desire to be fucked hadn't drowned out my fear of getting caught.

"Don't worry. We will be really quiet, okay?" he said softly, his urgency growing.

I could only nod in agreement because his fingers were doing wonderful things to my asshole. After a short while, he lay down next to me and aimed his cock at my waiting hole.

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