A Night 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
James19999
James19999
342 Followers

Finally, she pulled her face back from mine and looked down at me. Her brown hair had fallen out of the bun and was now hanging in my face. She had a devious grin as she continued to rock her hips back and forth. I exhaled sharply in pleasure, my dick rubbing against her groin, only a few layers of cloth separating us.

"Hold on a moment." She said, stopping and looking down at me.

"What is it?" I desperately wanted her to continue.

"I just remembered something." She climbed off me and stood up, leaving me lying on the bed and looking up at her. The panic that had given way to excitement when she had first kissed me on the couch started to resurface. I sat up and watched her walk to her dresser, worried but unable to take my eyes off her swaying hips and powerful, rounded glutes.

"What did you remember?" I finally managed to ask.

"You were sneaking out to see a guy, right?" She didn't turn around when she said it, and was fishing through her dresser.

"Oh, crap, I should probably tell him I'm not coming."

"Not what I was getting at," she said, turning around. She leaned back against it and bit her lip suggestively, a drawer open right next to her. "Just... what were you going to do when you met up?"

"You know." I said, wondering what game she was playing.

"I'm not sure I do. Why don't you tell me?"

"You know, I was hoping we'd... have sex." I admitted. Her grin grew wider.

"With a guy? What kind of sex?"

My ears and cheeks burned hot with humiliation, and I couldn't bring myself to look at her.

"You snuck out of your parents' house dressed up like a schoolgirl to meet a guy from a dating app. What did you want him to do with you?"

"I wanted him to fuck me."

"Well," she replied, "I'd hate to disappoint you." I could hear a jingling and something scratching on wood. I looked up to see Mrs. Johnson holding a black six-inch strapon in her hand. My heart was pounding as I watched her slide her panties down and begin wrapping the harness of the strapon around her waist. Her green eyes once again stared right into mine as she started lubricating the strapon.

"Take off those panties for me." she commanded. I obeyed, sliding the panties down from under the skirt and down to my ankles. I unhooked them from my ankles and dropped them to the floor. Mrs. Johnson walked back to the bed and looked down at me.

"Good girl. Now, lie down on your stomach for me."

I obeyed again, turning around and lying down, my face buried in the pillow. I felt that comforting weight of hers as she climbed on top of me and hiked my skirt up. The tip of the strapon teased my buttocks as she leaned down onto me. I felt her lips brush my ear, and a sudden pain as the tip penetrated me.

I gasped in shock.

"Shh, it's okay. I'll be gentle for your first time." She slowly eased it into me, and while the initial shock was still there, the pain didn't get much worse. Soon, I felt her hips pressed to my butt, and I knew it must have been all the way in.

"See? I wouldn't hurt you." She whispered, then kissed my ear. I felt her slowly pull out again and slowly thrust back in over the course of several seconds. I could feel it stretching me, and the force of the thrust ground my erection into the soft comforter below. There was another slow thrust, and I let out a breath.

Mrs. Johnson did another couple slow thrusts, and I found myself moaning in pleasure. A warmth spread through my body as she found the right rhythm, and soon I forgot the pain as she gently stroked in and out. She giggled at the sound of my moan.

It couldn't have been more than a minute, but I could already feel my dick beginning to tremble. I shuddered and my whole body spasmed, and with a gasp and a moan I could feel myself ejaculating. The orgasm rocked through my entire body, and I found myself trembling with the warm afterglow under Mrs. Johnson's muscular body.

She giggled again and rolled off me.

"You liked that, didn't you?"

I looked over at her and nodded, still too shocked to speak. After a moment lying there face down on her bed, I could feel the stickiness around my dick and realized I needed to clean up. I rolled over, put my feet on the floor, and stood up. It felt a bit odd walking after being pegged, and I must have been a little bowlegged as I made my way to the master bathroom.

I saw myself in the mirror, my blouse, skirt, and thigh highs still on, though my hair was disheveled and hanging in my face, and the knot at the bottom of the blouse had come undone, leaving it hanging more shapelessly than before. Mrs. Johnson entered the bathroom behind me, still wearing the strapon and grinning broadly.

"Thank you." I said, looking at her in the mirror.

"Mhmm." She said. "I selflessly agreed to fuck the prettiest boy I know."

I smiled at the compliment and started to turn around, but she put her hands on my hips, keeping me pointed toward the mirror.

"Bend over." She commanded. "I'm not done with you yet."

I paused for a moment and then obeyed, grabbing the counter in front of me with my hands and bending over. Now that I was bent over, my butt was perfectly level with the strapon. Her hands grasped my waist tightly as she slowly inserted it into me again. In the mirror, I could see her concentrating, her eyes squeezed shut.

Being penetrated again didn't have the same thrill after I had just orgasmed, and I could feel the pressure in my elbows as I held myself in place while she thrust into me. But I stared at her face in the mirror, and was fascinated to watch her look of intense focus slowly give way to pleasure. Her eyes were still closed, but her serious expression became a grin, and her exhales became moans. Her thrusts became stronger and harder, and I could see the look of pure ecstasy on her face as the thrusting made the strapon's base rub against her. Finally, she let out a loud, sharp moan, and, eyelids fluttering, she pulled out of me and leaned back against the wall, grinning.

Mrs. Johnson had a thin sheen of sweat on her statuesque body, but that and her satisfied smile gave her a radiant glow. I turned around and sat on the bathroom counter, looking at her. Panting, she finally opened her eyes and looked at me, the intensity of earlier replaced with contentment.

"Wow." She said.

"Wow." I repeated.

I made my way over to the toilet and grabbed some toilet paper to finally clean myself up. She unhooked the strapon and watched me for a moment, then set it down and walked back out to the bed. After I finished cleaning up, I stepped out of the bathroom. Mrs. Johnson motioned for me to come over. I sat on her lap, enjoying feeling her muscular legs beneath me. She wrapped her arm around my waist and pulled me in close, looking up at me.

"From now on, the only place you go when you sneak out of your parents' house is right here. Understood?"

"Yes ma'am." I said playfully. Mrs. Johnson reached onto her nightstand and grabbed her phone.

"Put your number in here. You're going to be sneaking out a lot."

I smiled at her, and obeyed once again.

James19999
James19999
342 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
11 Comments
AnonymousAnonymous4 months ago

that is it - Mr. James19999 - you a MAESTRO Literotica storytelling composer

now please turn out more masterpieces

AnonymousAnonymous4 months ago

Please add on to this!

AnonymousAnonymous7 months ago

Please make another part of this story pretty please

Fran_cdFran_cd9 months ago

Most young crossdressers dream of something like that happening. I know I did. Thanks for the hot story!

AnonymousAnonymousover 1 year ago

Turned a crossdresser gay. Not automatic and not good

Show More
Share this Story

Similar Stories

The Femboy and the Tomboy A shy college student meets the girl of his dreams.in Transgender & Crossdressers
Soft and Hard Chris gets more than he bargained for at the gym.in Transgender & Crossdressers
Study Group Surprise James explores his feminine side with his crush's roommate.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
More Stories