Summer Reunion

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"I want to peg you."

"Wait, what?" I asked, mouth wide with shock.

"I want to take a strapon and fuck you in the ass."

"I know what it means! I just..." The thoughts swam in my head as I tried to think of an answer.

"Why did you come here?"

"You invited me! I thought we were going to have drinks and..."

"And what?" It was like her eyes were boring into me. Her hand cupped my chin, not letting me turn away this time. My hands were resting on her thighs, feeling her hard muscles tensed. When I didn't answer, Emily spoke.

"You came here because you wanted to fuck, didn't you?"

"I... yes."

"So then," she said, leaning down, pinning my torso under hers, and her lips brushing my ears, "let's fuck."

I gulped. She nipped at my ear, and I could feel her trembling with anticipation on top of me. I realized I was trembling underneath her too. She savored the moment a little longer, then climbed off me to sit on the edge of the bed. I leaned up as well, and she looked over her shoulder at me, eyes piercing through me. I averted my eyes once again, but could see her smiling with my peripheral vision.

"Come on." She said, grabbing my hand. She stood up, pulling me off the bed and onto my feet. Wrapping her toned arm around my shoulder, she walked me over to the dresser.

"Help me with my shorts." she ordered, giving me a gentle push down with the hand on my shoulder. I found myself kneeling at her feet, eyes level with her abs. Trembling, I unbuttoned her denim shorts and slid them down her thighs.

Emily turned and opened a drawer of the dresser. She pulled a couple of things out, which I took a closer look at. One was a black six-inch strapon. The other was a bottle of some kind of clear liquid.

"Are you going to rape me?" I asked.

"No. You're going to consent."

I felt the panties tightening at the front and realized I was getting hard again. My heart was racing fast; I couldn't believe what I was hearing. And I couldn't believe that underneath my fear, some part of me was excited for it.

When I looked back up, Emily had slid her own panties off and was putting on the strapon. I knelt at her feet and watched her. The way she was trembling with excitement, she struggled to fasten the harness. Finally, she managed to get it secured, and she reached out, grabbed my hair, and dragged me up to my feet. I was pinned between her hard body and the hard wood of the dresser, with the hard rubber of the strapon between my legs.

"Wait!" I said, breathing almost as heavily as she was.

"For what?" she asked, eyes gazing into mine somehow even more intensely than before.

"I-"

She leaned in and kissed me hard on the lips before I could say anything. I felt her press something into my hand, and when she pulled her lips away and I looked down, I saw it was the bottle of lube.

"You have twenty seconds before I go in."

I looked at her, startled, and then processed what she said. Now I probably only had eighteen seconds, and the expression on her face was deadly serious. I hurriedly unscrewed the cap and started lubing up the strapon, which wasn't easy the way she was grinding her hips against me.

Her hands reached behind my thighs and she abruptly lifted me onto the dresser, stepping in between my legs and placing my ankles on her shoulders. I wriggled helplessly, trying to get into a comfortable position as she angled to lift my tailbone up to expose my butt.

My struggling only seemed to turn her on more. She reached down and grabbed the waistband on the panties, tearing them clean off.

"Wait!" I said again.

She didn't. I gasped sharply as she slid the tip of the strapon into me. Her hands slid down my thighs and onto my waist, holding me in place as she pushed in. I gasped even more loudly as it went the rest of the way in, her hips resting against my buttocks.

Emily's mouth opened in a moan as the base of the strapon rubbed against her. She pulled it most of the way out and shoved it back in.

"Works way better when you don't cum before you even get it in." she said smugly, starting a slow but firm rhythm. Her hips rocked back and forth as she thrust in and out of me. I gritted my teeth, trying not to shout as she stretched me out. Her thrusts drove my back along the hard wood of the dresser.

After the first minute or so of Emily's thrusting, I began to feel a warmth spreading through my body. The pain from the penetration and from being ground onto the wood of the dresser was still there, but it wasn't the only sensation. I involuntarily moaned, and Emily looked down at me savagely.

"I knew you'd like it!" she hissed triumphantly.

"Oh!" I moaned again, tilting my head back.

"This is how it's done, you little slut!" she said with an especially sharp thrust. I moaned, and she moaned even louder. She was thrusting hard and fast now, and the strapon inside me, Emily's hard body against the undersides of my thighs, and the wood under my back became my whole world. I don't know how long we were there like that, her pounding me and me taking it, but I soon felt my whole body spasm. I shook uncontrollably, and a wave of pleasure spread from my pelvis to the rest of my body. There was another hot splash, this time inside the skirt, and I realized I had had another orgasm.

I looked up and saw Emily looking down at me, breathing heavily, a bead of sweat on the side of her face, and smiling contentedly. She slowly pulled out of me, walked back over to the bed, and sat down, panting.

After a moment, I felt my back aching. The dresser really was uncomfortable. I slid forward and planted my feet on the carpet of the bedroom floor, then stood up. Emily looked over at me.

"Thanks. I needed that." she said, all the hunger and intensity and fury gone from her eyes, replaced with contentment. I almost sat down next to her on the bed, but now I was feeling a sharp pain in my butt from the punishment I had just taken. I knelt down next to her and rested my head on the edge of the bed, my forehead resting against her thigh. She reached down and ran a hand through my hair. We sat there catching our breath for a minute before Emily spoke again.

"Are you okay? Sorry if I got a little rough there. I don't know what came over me."

"I'm - I'm fine." I stammered, pretty sure I was telling the truth.

"You're just so... just so..." Now it was her turn to lose her train of thought. I looked up at her, waiting for her to finish.

"We've got the rest of the summer, right?" she asked, still panting.

"Yeah." I answered with a smile. She smiled back.

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AnonymousAnonymousalmost 2 years ago

I wasn’t expecting that but, when she wanted to peg him I was like what the fuckkkkk?, I was expecting her to pull out a dick lol, nonetheless great story.

sissyboi69Aricsissyboi69Aricabout 2 years ago

I love stories like this, please write more about your summer

AnonymousAnonymousover 2 years ago

Freely given and non-coerced consent is sexy. Don’t underestimate that.

KandiKoxKandiKoxover 2 years ago

Another awesome effort - thank you! It would be great to know how much further Hayden is prepared to take his feminisation, but also to learn more about Emily and her background. If she has a strapon handy, this is clearly something she’s done before - but maybe previously only with girlfriends?

AnonymousAnonymousover 2 years ago

Well done!

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