Falling for David and Meeting Shari

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He smiled back. "Yes," he said.

"But maybe it's not a fair comparison," I said. "Maybe if you had got naked with him too . . ."

"Well," he said, "he's undoubtedly more experienced than you."

"Hey, I did research!"

"But he has actual hands-on experience. You can ask him for advice. Or just watch him in action."

"Hah!" I said. "I see where this is going. A competition between me and Steve to see who can make you hornier."

"Well, as you would say, there's no downside to that. Not for me, anyway."

We lay in each other's arms, looking at each other, smiling and kissing.

"I want to see you naked," he said. He sat up and undid my robe. I was hard already, but felt my cock grow harder still as he folded back my robe and I was naked for him.

"I love your cock," he said. He took it in his hand and started to stroke it. "Tell me what you'd like me to do to you," he said. "I want to give you as much pleasure as you gave me."

"I want your hand on my cock, just like that, stroking me," I said. "And I want you to kiss me as you do it."

He leant over me and kissed me, a long series of deep kisses, broken only by my moans as each stroke of his hand sent a spark of excitement racing through my body. I ran my hands over his body and took his cock in my hand. It was hard again, and holding it my hand cause my excitement to grew yet further. I sensed I was going to cum soon. David noticed that too.

"I want you to cum in my mouth," he said. "Will you do that for me?"

"Yes," I said.

He kissed me again, then moved down to my cock. He took it in his mouth, and the caress of his tongue and the movement of his hand at once brought on my orgasm, spasm after spasm, releasing long streams of cum, shooting deep into his mouth.

He held my cock in his mouth until its hardness began to wane, then he sat up and looked at me with a grin on his face.

"You look adorable," I said.

"Do I have cum on my face?" he asked.

I pulled him down towards me and kissed him and licked the cum from his face. He lay on my shoulder. We were silent for a while, just holding each other close. Then we started talking. We talked like we had always done. About nothing much. It felt just as it did before we told each other that were in love. But, now and again, we caught each other's eyes and smiled and kissed.

"So when did you first start to think of me as other than a friend?" I asked.

"One night you were at my house and I fell asleep next to you on the bed. When I woke up, you were looking at me and smiling. And at that moment I wanted nothing more than for you to kiss me."

"I wish I had done so."

"And from that point on I realized that I was falling for you. And I started thinking about us as lovers, imagining what we might do."

"What did you imagine?"

"Lots of stuff. Lots of fantasies."

"Tell me the best."

"Hmm," he said. "I'm not sure you're ready for that one."

I put my hands on his waist. "Tell me or I'll tickle you."

"Go ahead," he said. "That will make me even more horny."

I put my hand on his cock and again felt its hardness. I moved up against him so our cocks were touching. I held them both in my hand and stroked them gently.

"Tell me," I said.

"You sure?"

"Yes."

"It's very kinky."

"Even better. Tell me."

"I imagine that you come to my bedroom late one night. I'm dressed in a short skirt and a white blouse. My hair is tucked behind my ears and I have some make up on. I imagine that you put me on my knees on the edge of the bed and lift up my skirt and fuck me. That's it."

I was silent for a moment.

"Wow!" I said.

"Wow what?" he asked in a quiet voice.

"Wow that's so amazing!" I said.

"Amazing good or amazing weird?"

"Amazingly kinky. Amazingly wonderful," I said. I kissed him on the lips, gently. "Have you ever dressed up like that?"

"Yes," he said quietly. "I sometimes dress in my sister's clothes. The fantasies are much more intense when I dress up."

"You must look so pretty."

"You're not shocked?"

"Yes, totally, but in a wonderful way. I love it that you're so kinky. I love it that you told me your fantasy. I want to make it come true."

"Really?" he asked. "I can dress as a girl and you'll fuck me?"

I stroked our cocks more firmly.

"Yes sweetie. The idea of you being both my boyfriend and my girlfriend is incredibly exciting."

He smiled at me. I guessed what the smile meant.

"You brought some clothes with you, didn't you?"

He nodded.

"And you're going to go put them on, aren't you?"

Another nod.

"And I'm going to fuck your cute girly ass, aren't I?"

He nodded again and jumped out of bed. He took his backpack and went into the bathroom.

He came back a few minutes later, transformed. In place of the cute boy there was a cute girl, her long blond hair clasped back behind her ears, her eyes and lips accentuated by light make-up, and wearing a short tartan skirt and a white blouse. She stood at the end of the bed, inviting my gaze. "Hi," she said. "I'm Shari, David's feminine alter ego."

"Incredible," I said. "Just when I thought you couldn't get even cuter you turn into Shari!"

"You're not the only one who did research," she said. "I had to watch so many You-Tube videos to learn how to put on make-up!"

She reached for my hand and helped me off the bed. I stood in front of her and she held my hard cock in her hand.

I undid the buttons of her blouse and held her hard nipples between my fingers.

"When you were sucking my nipples," she said, "I was imagining that I had little boobs and you were sucking on them. Is that kinky, or what?"

"Wonderfully so," I said.

"But now I want you to fuck me," she said. "To fuck me hard. I don't want you to care about my pleasure. Just your own. I want you to use me. You understand?"

I nodded.

"I'm going to kneel on the edge of the bed in front of those mirrors," she said, pointing to the full-length mirrors on the closet doors beside the bed. "You're going to stand behind me and fuck me while I watch you in the mirrors."

She knelt on the edge of the bed. I stood behind her and guided my cock to her ass. I hesitated, fearing I would cause her pain.

"Fuck me!" she said. "Fuck me now!"

I pushed into her.

"Deeper," she said.

I pushed deeper into her. "Deeper still," she said. I pushed deep into her, then started fucking her, long slow strokes in and out, my hands on her hips pulling her against me as I pushed into her and relaxing my hold as I withdrew.

"Yes," she said, "like that! Fuck me like I'm your girlfriend."

My orgasm built quickly. "I'm going to cum soon," I said.

"Cum then. Cum deep in me," she said. "And say my name as you cum."

I came in her, so hard, my orgasm crashing over me with an irresistible force. I moaned her name as I came. "Shari, Shari, Shari." My words were met by her long moan of pleasure.

I stood behind her as our orgasms subsided. I saw her face in the mirror smiling at me.

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

"Shari is amazing" I said.

I was lying on in the bed holding David in my arms. After we fucked, Shari undressed, and we showered together.

"She amazes me," he said. "When I'm her, it feels like there's nothing I won't do. Do you think I'm schizoid?"

"No," I said. "I think you're just channeling your deep down sluttiness."

"It's true. Shari is a total slut."

"Yes," I said. "She's going to have lots of fun."

He looked at me with a smile. "So who do you love more? David or Shari?"

I laughed. "You think I can't spot a trick question? I love them both, equally."

"Me too," he said. "Sometimes I'll just want to be David and have you make love to me slowly, and gently, and tenderly. Other times I'll want to be Shari and have you fuck me hard and use me for your own pleasure."

"I'm so lucky to have met you both," I said.

"We're so lucky to have found each other," he said.

That night we fell asleep in each other's arms. We woke up early, and made love slowly and gently, in a half-asleep, half-awake state, then fell back to sleep together.

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

When we checked out, there was a different woman at the desk than the one who had checked us in.

"I hope your stay was enjoyable," she said.

"Very enjoyable," I said.

As we walked away from the desk, I took Shari's hand in mine. We took a cab to her house. In the back seat of the cab her skirt lifted up to expose her hard cock.

"The driver might see," I said.

She shrugged her shoulders.

Her parents and sister were out when we arrived, as she had known they would be. She took my hand and led me to her bedroom. "Fuck me," she said. She knelt on the edge of her bed and I fucked her, calling out her name as I came.

I lay beside her and she held me in her arms.

"Is Steve going to meet Shari?" I asked.

"Of course," she said. "Shari is a slut, remember. She can't possibly resist his huge cock."

She kissed me gently.

"And I want you to play with my nipples and kiss me as he fucks me. Will you do that for me, baby?"

"Yes," I said. "I'd like that. Very, very, much."

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5 Comments
AnonymousAnonymous3 months ago

Very hot…. Would love to have a mature Shari to fall in love with and get married….become just a normal couple…

AnonymousAnonymous8 months ago

Don't like the whole swinging aspect but otherwise a good start.

AnonymousAnonymous9 months ago

How can I talk to other cross dressers?

KatiwantsKatiwants9 months ago

Mmmmmmmmm mmmmmmmmm such a wonderful story!! 😍😍😍💋

TeriLeighTeriLeigh9 months ago

Ooo, Shari is in for a real good time if she goes all the way with Steve.

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