Meeting Jenna

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"This time I want to fuck you on your knees."

Her body writhed. "Are you always this dominant?" she said.

"No, not always. Sometimes I'm far more dominant than this."

"Oh God'," she said, with a tremble. "Just tell me what to do."

I grinned. I wasn't going to go very hard on her. It would be irresponsible, but fucking her on her hands and knees would be a nice, gentle start for today.

"OK, get on your hands and knees," I said, "and face yourself toward the foot of the bed."

With extreme difficulty, she crawled up. Her muscles were still shaking, but she hauled herself into position. Her face looked down toward the sheets.

"Look up," I said, and she complied.

She expelled a little gasp as she realized she was looking straight into the large mirror on my wardrobe door.

"I want you to watch your face as you get fucked," I said with a grin.

I positioned myself behind her, with my cock raging. I grabbed the lube and squirted another load into my hands. Then I worked it around her little anus. In the mirror, I could see her eyes roll back into her head. I slid my lubed finger inside her, giving her the thick, fresh coating she'd need to take another pounding. Her ass opened up quicker this time, eagerly accepting my finger.

Once she was done, I coated my cock for extra slickness.

Satisfied we were both ready, I wiped my fingers on a tissue and looked at her prostrate body. I couldn't help but reach under her and knead her tits with my hand, then trace my fingers along her stomach until I could wrap them around her hard, throbbing dick. She moaned as I gave her the tiniest of little jerks.

"Fuck me," she panted.

I was going to do just as she asked, and this time I was going to fully enjoy myself. She was going to get an asshole full of spunk.

I drew myself up behind her and gripped the base of my cock. Gently, I began to slap the head against her pucker. She whimpered.

"Are you ready?" I said.

"Yes!" she said, then lowered her face all the way down to the sheets, and reached around with her hands, spreading her butt cheeks. "Please!"

I grinned, then slowly pushed my dick inside her. Bit by bit, she took it. I watched her face in the mirror, as it screwed up in pleasure tinged with pain. As I pressed myself inside her, a throb of pleasure surged along my cock. God, she felt good. I eased myself in and out of her, groaning as her warmth enveloped my shaft over and over.

She was tight, but as I continued to thrust, she began to loosen. Little whimpers left her lips every time I sank myself into her, all the way to my balls.

I began to pick up the pace, thrusting faster and harder. Jenna started to moan loudly. In the mirror, I saw her bite down onto the sheets.

It was time.

In a roar of pleasure, I started to pound her full pace, full strength.

"Fu . . . uuuu . . . ckkk!" Jenna moaned, her voice juddering. Fresh tears leaked from her eyes, and drool spilled from her mouth.

Surge after glorious surge of pleasure flooded along my shaft.

"You like this?" I growled.

"Yea . . . hhh."

I raised one of my hands and slapped it down onto her ass. I watched the impact ripple through her.

"Oh . . . God," she moaned.

"You like that!"

Her head nodded as her face burrowed into the sheets.

"Look up at me!" I ordered. "Look at my eyes in the mirror"

Her head tilted up, but her teeth still gripped the sheets.

I unleashed again, this time on her other cheek. She wailed. Her pupils wide and crazy. Then I spanked her again, and again. Her ass began to glow pink.

I kept spanking her as I thrust. The surges of pleasure running up and down my shaft were almost too much to handle.

"You like being dominated?" I rasped.

Her head nodded, her eyes locked onto mine.

"Are you gonna cum?"

Her head nodded again.

Her back began to arch. Her groans deep and rhythmic. Her ass started to tighten.

Then she spurted. Big ropes of cum ejected from the head of her cock all over the sheets. She screamed in pleasure.

It was too much for me. Watching this beautiful girl cum, watching her blow her load, watching her teeth clamp down onto the sheets-it forced me over the edge. Suddenly, a big rush of cum surged along my dick and expelled itself deep in Jenna's ass. Each of my thrusts was joined by a fresh pulse of sperm and a powerful wave of sexual gratification.

"Fuck," I moaned, as I slowed my pace. "Fuck, fuck, fuck."

Slowly, I pulled out of her, watching her anus pulse over and over. Little globs of semen squeezed out of her with each contraction.

She collapsed onto the sheets, her body jumping and twitching. A damp puddle of tears and drool coated the sheets near her face, joined, almost certainly, by a large sticky trail of spunk under where she lay.

"James, oh God, James," she whimpered.

"You're wonderful, Jenna," I said, soothingly and ran my hand through her hair. She didn't move, but her eyes quivered open and she looked over at me.

I lay next to her.

"Come here," I said, opening my arms for her.

Her sexually broken body struggled to do anything but tremble, so I carefully slid my arms under her and drew her close for a hug.

"Th . . . ank . . . you," she managed as I held her close.

As I embraced her, my hands soothed across her delicious skin. She nuzzled my neck as I stroked her. I became lost in calm, wonderful post-orgasmic bliss. Time lost its meaning. I didn't look at my clock and I didn't want to. Our bodies fitted together so well, I felt we could have lain like that forever. As the minutes, or perhaps hours, passed, I noticed Jenna had begun to sleep. I kissed her lightly on the cheek, and soon after my eyelids began to sink. I entered my own state of beautiful slumber.

* * * *

Hi everyone,

That's it for now - I hope that you enjoyed the story!

If you liked it, or even if you didn't, please send me a message or leave a comment. It's what authors thrive on and what keeps us writing. I choose publish my stories rather than keep them to myself, because I like to use my words to inspire feelings and emotions in others. Without feedback authors cannot know how well that has happened, or even if it has happened at all.

I have been writing for a few years in a number of different genres. I cannot begin to describe how motivating it has been to hear from readers who have enjoyed my work - and how helpful it has been to receive honest and constructive criticism.

Yours faithfully,

Alex

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
63 Comments
not1foryounot1foryou4 months ago

Lovely story of match-making turned into brazen lust with some gentle kink!

marciekitmarciekit7 months ago

I know I'm late to the party but you are a masterful author. I imagine you have some experience given your details and their accuracy. It was very balanced in terms of background compared to actual sex. I loved this work

JynnyJynny11 months ago

So happy I ran across your touching story of love and lust. I know from experience that no one with any character & heart "EVER" wishes to deceive another, especially when it comes to being who we know we really are. Jenna was sure of herself in who she was yet was very protective in showing it....until she met James. Well done ALEX, well done...Jynny ( a woman in a mans body)

rlh100rlh10012 months ago

What a wonderful and caring story. A first experience as a trans person must be very stressful. Your story made it a beautiful experience and hot too.

AnonymousAnonymousabout 1 year ago

Thanks for a great storey. I could almost feel the chemistry working. I am sorry to say that there are far too few stories of this kind with this subject matter, but this is one of the best I have read.

Show More
Share this Story

Similar Stories

My Adorably Hung Summer Roommate Darren meets Danielle, a petite redhead w/ something extra.in Transgender & Crossdressers
The Happiest of Endings A massage with a big, hard surprise.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
She Has a What?! Teaching his roommate how to use her assets.in Transgender & Crossdressers
Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
More Stories