Roger, Over and Out

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

Eventually, Roger bent down to kiss me once more, his beautiful face filling my world. "Fuck me with your beautiful cock, Ishmael. Can you feel how tight I am for you? Can you feel how perfect you've made this first time for me?"

I nodded, suddenly choked up and unable to speak. I felt a tear roll down my cheek, and Roger kissed it away. "Time for you to come in me, Ishmael. Don't worry about me, I've already come so hard tonight. Right now, this is for you." He kissed me again. "You want to get on top?"

We carefully rolled over, my cock slipping out in the process. Roger opened his thighs, and I covered his body with mine, pushing back inside with only minimal fumbling. He gasped at the new penetration, and I felt his soft breasts and hard nipples shudder against me as we embraced. His voice was getting louder with each word, no doubt informing our entire dorm floor of our fucking, but I didn't care one bit. "Go for it, Ishmael. Fuck me. Pound me, I want you to destroy my tight virgin pussy!" I was soul-deep in an endless well of lust, and I did my level best to do everything Roger begged for with each new thrust.

This was heaven. I was already primed to blow, so after only a couple of minutes of hard thrusting in this position, I was rapidly reaching the point of no return. "Roger, almost there, gonna...oh god..."

Roger's soft thighs wrapped around me, trying to pull me in deeper on each stroke, and I lifted my body up just enough so I could see his face, after pushing my long hair out of my eyes. His voice was quivering with need, his eyes staring deep into mine. "Come for me, Ishmael, come in my pussy, please, I need it, I need you..." Those last words pushed me over the edge, and I felt my body spasm as sparks burst inside my eyes. I heard myself practically scream in joy, and I can only hope that my "O" face afforded me at least a little dignity.

I felt Roger's tightness squeeze around me in time with his heartbeat, and I carefully pulled out, taking care to make sure the condom stayed on. With knees wobbling like a child's toy, I staggered to my feet and slipped off the latex, dropping it in my trash basket. I grabbed a washcloth from my shower basket, wiped the mess off my lowering rod, and then wordlessly climbed back into bed with Roger.

Roger greeted me with a kiss, throwing his arms around me. "Ishmael, I believe this is the start of something beautiful."

I reveled in his soft curves cuddled up against me, and I turned to face him in my bed. "God, yes. Stay with me tonight."

He giggled, nipping at my ear again. "You couldn't pry me out of your arms with the jaws of life tonight. I'm staying right here."

We quietly kissed and caressed a little more, before sleep eventually pulled me down into its embrace.

---

Hours later, my senses registered something wonderful -- I had a warm mouth sucking my cock, and I was as hard as steel. I opened my eyes, and Roger's beautiful wet pussy was right in my face, his knees to either side of my head as he buried my length down his throat. I did the only sensible thing, and lifted my head off the pillow to wrap my mouth around his clit.

"Oh FUCK!" Roger let my cock fall from his lips as I tasted his delicious pussy for the first time. "Good morning, Ishmael."

I murmured a vague response, my mouth too full of soft wet flesh to respond properly.

"Welcome... ahh.... to the first day of the rest of your life, Ishmael. I promised you a lovely wakeup, and I keep my promises."

I responded by slipping a finger into the deep wetness before me, and then taking that finger out and slowly pressing it against his ass. I relinquished my mouthgrip on his clit long enough to respond. "So do I, roomie. So do I."

Roger gasped, hungrily licking across my balls as I invaded him. "You do that, Ishmael. God yes, don't stop, that's much better than my plug...mmm. But don't forget..." He paused just long enough to engulf my cock for a quick deep-throat treat, and then came up for air once more. "...After you make me come on your face, you owe me a coke."

THE END

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
13 Comments
AnonymousAnonymousover 1 year ago

I may not understand genderfluid, but I do understand sex between a male and female! Good story, now give us rest of Jen, etc.

Hottdreams80720Hottdreams80720about 2 years ago

Selected your story at random. Great story that made me want more from you. Love the FTM twist and the artful enlightening way you portrayed Roger. Thank you, Mike

BambiBimbetteBambiBimbettealmost 4 years ago
Spectacular story

So not what I was anticipating. A romance more than anything else. Our potentially star crossed lovers meeting and slowly learning each other’s secret. The lead characters are different than what we run into here and that made the story all the better. This is an interesting story idea that was well executed. You should be a very proud author.

AnonymousAnonymousalmost 4 years ago

This story is absolutely beautiful

bhojobhojoalmost 4 years ago

Very sweet and well written.

Show More
Share this Story

Similar Stories

Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
Lily An accident leads to a very pleasant surprise.in Transgender & Crossdressers
Something Better Unexpected love is the best cure for a broken heart.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
More Stories