Pegging Tales: Justin's First Time

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

"Take your pants off, underwear too," she commanded.

I slowly unbuttoned my pants and then kicked off my shoes. Stepping out of the pants, I then stripped off my underwear. I was about to take my shirt off, when I heard her say, "You can leave that on for the time being."

I stood there nervous about what was going to happen next.

"Kneel."

I got in my knees and gulped as she moved her hand on the shaft of the fake penis and slowly began to stroke it.

"Open your mouth and stick your tongue out," she commanded and I did as she asked.

She began to gently smack her strapon cock on my tongue and then began to smack it on my face.

"Suck my dick!" she ordered.

I grabbed her strapon and slowly took the head into my mouth and then began to suck on it. I sucked on it slowly. It felt weird in my mouth, but that weirdness went away in a couple of minutes and I was really beginning to get into it.

"Ummm...good boy...are you sure you haven't sucked cock before?"

I simply shook my head sideways while her big black cock was still inside my mouth.

"I find that hard to believe."

I just continued sucking on her fake phallus and she began to get into it herself.

"Yes, that's it keep sucking my cock like that slut," she encouraged.

I grabbed her cock and began to take it into my mouth. I immediately tried to take the entire cock, but that was not possible because of my gag reflex. I nearly choked on the beast and released it from my mouth.

I began to stroke her phallus like it was a real cock. Rebecca moaned and leaned back onto the arm rest of the couch.

"Yeah, jerk my cock! You like it don't you?"

I simply just nodded again. She pulled my t-shirt off me and then motioned me to get onto the couch. I sat on the couch as she thrust the cock closer to my lips.

"Get that dick back in your mouth!"

"Yeah baby, that's it. Keep sucking on my big dick!"

I grabbed her fake phallus and really started getting into it, sucking on it with my drool all over making my face and her cock shine with my spit. She pulled the cock out of my mouth, grabbed my arm helping me up and pushed me against the wall next to the entertainment system, with my face against the wall.

She removed her robe and spat on her hand and began to rub it all over my ass hole. She licked her fingers and lubed it with her spit and reached down to my rosebud giving it a slight tickle. She rubbed her finger all over my hole and then slowly began to put some pressure on it. I felt her finger slowly enter my ass.

It hurt, but she tried to be gentle. Finally her finger was completely in and she began to finger fuck my ass slowly. It didn't hurt much after a few seconds, instead I felt pleasure as she tickled the inside of my ass. She then boldly stuck another finger in there, eliciting a gasp from me and began to really drive her fingers in deep.

"You like that baby?"

"Yeahhhhhh..." I grunted.

"Yeah....well you'll love what's coming next!" she proclaimed.

I felt an empty feeling in my but, as she removed her fingers and positioned herself behind me.

"Arch your back and stick your ass out for me baby," she guided me.

I did as I was told and arched my back, sticking my ass out for her. She moved in and began to rub her cock all over my virgin rosebud.

"Ooohhh...took at that tight little ass begging to get fucked. You want to get fucked, don't you?"

"Yes."

"Say it!"

"I want to get fucked in my ass."

"Good boy," she said. She then spat on her hand once more and began to rub it on my asshole. I then felt the tip of her cock against my ass and she gave it a hard push. It didn't go in.

"Breathe. Relax your muscles. If you don't relax it's going to hurt!" she said.

I tried to relax myself as much as I could and took deep breaths. She began to push against my ass a little harder this time and my ass slowly gave way and the head of her cock entered my tight hole.

"FUCK!!!" I screamed.

She pushed in a little further as I winced in pain. It really hurt and my ass felt like it was on fire. She held on to my hips and stayed there. She leaned on me, her breasts mashed against my back and kissed my neck. She put her left arm around my stomach, while her other hand reached around for my cock and slowly began to stroke it. She leaned into my ear, I felt her warm breath as she whispered, "I just love a nice ripe tight ass."

She then pulled her cock out, with only the head still inside me, and pushed the dildo in a little deeper. She did this a few more times, as I continued to wince in pain. She pushed one more time and buried her cock inside me completely down to the hilt. She stood still, letting me get used to her cock as her arms held me firmly in place.

She kissed my neck once again and then slowly began to pump into me. The pain had now gone and all I felt was pleasure. Her cock was buried in deep inside me and I could feel it hit my prostate. I began to moan and grunt as she began her slow assault.

"Oh yea, take my cock! Oh fuck yeah!"

She let go of my cock and held onto my hips and slowly began to build up a rhythm. I was in heaven. It was even better than I thought it would be. Now I knew how all those men felt while they took their girlfriends or wives didlo's up their asses.

She smacked my ass and began moving faster.

"You like my dick in your ass?"

"Oh fuck, I love it!"

"Yeah...say it!"

"I love your cock in my ass."

"Louder!"

"I LOVE YOUR FUCKING COCK IN MY ASS!"

"Good little bitch boy."

She pulled her cock out and pulled me behind the sofa. It had this big block attached at the back which I guess served like a show stand or something. She bent me over again, my ass sticking out even more this time. Instead of being gentle, this time she drove the entire cock inside me in one go.

I yelped as she held on to my hips and rocked her hips back and forth.

"You take it up your man pussy like such a pro!"

Her thrusts became harder and faster. I leaned down further as I felt her hard strokes rub against my prostate.

I grabbed onto the back of the couch hard as each deep thrust drove me to new heights of pleasure. Man this felt really really good. I grabbed her hand as she thrust into me.

"How does it feel to be on the receiving end, bitch boy?"

"I love it. Please fuck me more!"

"That's what I like to hear!"

She removed her cock from my ass once again and flipped me over and thrust inside me once again.

"Ohhhh fuck!"

Hearing me moan in ecstasy, she began to ram in harder and faster.

She grabbed my cock and began to jerk me off, I could feel my orgasm begin to rise as she continued her violent assault. All it took was a few more thrusts and some jerking off and my orgasm hit me hard. Cum began to fly out and landed on my chest. She didn't stop fucking and jerking me off until I released the last of my cum.

Once I was spent, my cock went limp as she released it and withdrew from my ass. I felt emptiness inside as she drew her cock out.

"Damn, that was hot!" she said.

"I can't believe I came so hard! I have never cum like that ever," I replied.

She flashed me that devious smile once again.

"Good. Can you stay the night?" she asked.

I didn't have to think twice. "Yes."

Her grin got bigger as she said, "We're going to have a long, long night!"

THE END.

*-*-*

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
19 Comments
AnonymousAnonymousabout 1 year ago

Loved it!

Newtothisstuff75Newtothisstuff75almost 5 years ago

That's sgreat story I read it to my wife as she stroked my butt as I'm wearing our first strap on with my hard cock forced into the hollow inside I'm going to fuck her pyssu with it then she is going to put it on and make me suck it like a good little cock sucking slut then she is going to lye me on on my back pull my legs up and fuck my asshole for the first time I'm wearing a collar and we are both fully shaved

We are going to cum hard, if i cum on my belly she us going to smear it all over her cock and make me clean it up

Can't wat

ramperampealmost 6 years ago
have tried

It feels nice when you are relaxed and turned on. The dildo should better be small than big for first timer. Hope you find some company for pegging.

charliebillcharliebillover 6 years ago
Try this?

I’ve tried many things in sex, but never this. As long as it’s a woman on the other end of that “cock”, (only), could be interesting!

tazz317tazz317about 7 years ago
EXPERIMENTATION IS GOOD FOR THE SOUL AND LIBIDO

but what do you do for kama-sutra 2. TK U MLJ LV NV

Show More
Share this Story

Similar Stories

Tamed by Meg Megan introduces me to the pleasures of being penetrated.in Anal
Her Presents She had a number of surprises for him.in Fetish
Easy First Date Girl uses strapon to peg a boy.in Anal
Strap-On Roommate Two guys are done by women with strap-ons.in Fetish
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
More Stories