*-*-*

Pegging has been a topic that I have wanted to write about for a very long time. In my personal life, I have yet to do it. It has long been a fantasy that I felt has been left unfulfilled for a while. I have read a lot of stories on the topic and have loved most of what has been published on Literotica. So I thought it was time maybe I write a story of my own and see how readers respond.

NOTE: This is completely fictional and I am writing it from the male character's point of view.

NOTE: Thank you to Wayne for editing this story. A special thanks to silkstockings lover for input and some help in writing Rebecca's profile on the pegging site.

*-*-*

Hello readers. My name is Justin and I am 21 years old. I live in the fair city of Dubai and am just in my final year of university. I live alone right now, in my own private man-cave as I like to call it, much to the disappointment of my mother.

Like any hot-blooded guy, I watch porn. And I love jerking off to a nice hot chick getting drilled; pussy or ass doesn't matter as long as I can jerk off to it. Lately though, I have been getting a little too bored with all the content that is on the various porn sites I peruse. Today for instance, I am a little too frustrated since I haven't jerked off in a couple of days. So I'm at PornHub looking for some nice videos so that I can play with my little mister, but I don't see anything that particularly interests me. I kept going through the site for a while and then something caught my eye.

A video titled, "Wife Fucks Husband with big strapon".

I had to say that it got my attention. I knew there was some kinky shit out there on the internet, but I had never come across something like this. As usual, seeing something new, curiosity gets the best of me and I click on the link. It takes the video a few seconds to buffer and the video starts.

The video looked like it was taken by an amateur couple where from the get go, I see a man bent over the bed with his ass sticking in the air. A woman wearing a corset and stockings comes into view. I see a little something extra attached to her hips. As the view gets a little clearer, it's pretty clear that she's wearing a strapon and is going to fuck her husband. Both their faces can't be see in the video, but the woman has a smoking body.

"Are you ready bitch?" I hear the woman say.

As I hear this my cock twitches. The woman moves closer to the husband and rubs her plastic cock on his ass. She teases him for a few seconds and I can feel my cock begin to harden. Yes, I was getting hard. The woman then pushes her fake cock inside the husband's ass, moving her hips slowly and trying to get as much of the dildo in as she could. She then removed the cock from his ass and this time pushed into his butt with a little more length going on.

"Oh, fuck!" exclaims the man.

"Oh yea, look at that. Such a lovely view," I hear the woman say.

She then begins to pound the man slowly at first building up a rhythm. By this point my dick is in my hands and I am pumping it slowly as the woman slowly ass fucks the husband. The woman picks up speed and so do I.

"Play with your cock, while I fuck your ass!"

I begin to pump faster as the woman continues to fuck the husband in the video. I am getting close to orgasm and then I see the husband scream in ecstasy, signaling that he has cum. But the woman continues to fuck him until the man has been drained of the last drop of cum. As I watch, I reached boiling point and I felt my balls stir. Jets of cum fly out of my cock and land on my t-shirt as I continue to pump my dick, watching the action on the screen. Now spent, I turned off the video and went to bed.

*-*-*

Over the next couple of days, I kept thinking about the video that I saw. I began to get really curious and wondered if a lot of men really liked doing that with their female partners. I spent a lot of days in class thinking about it too. And then I started going online and reading up on it. Pegging, which is the official term for it, is something a lot of men out there love. Not that it shocked me, but rather it was something different. I mean hey, a lot of people are into bondage and other stuff. I've seen plenty of videos of guys tying up girls and then fucking the shit out of them. But this was different. This was complete role-reversal and the thought of it turned me on somehow.

So, as you can imagine, I spent the next couple of weeks watching a lot of pegging porn. I came across hundreds and hundreds of videos. A lot of it was professionally shot porn, but there were quite a lot of amateur videos of couples out there too. After watching a lot of the mechanical professional porn, I turned my sights towards amateur porn. Mostly because it felt more realistic and it was real couples who enjoyed that stuff, as compared to porn models who just do it for the money. I even watched the amateur stuff where the women had their men dressed in lingerie and fucking them like bitches in heat.

Day after day, I jerked off to that stuff. And each day my own curiosity about how it would feel to get fucked in the ass by a woman wearing a strapon increased as well. It got to a point where I really, really wanted to try it out. But most of the girls I knew would never do it to me. I have slept around with a few girls and have noticed that while a lot of them are into kinky shit, they mostly like it done to them. I have never come across a girl who likes to be in charge.

So I continued looking up the subject on the internet, while also trying to see if there was a way to find someone I could try this with. Surely there had to be websites out there that catered to this stuff. So I searched Google. Then I came across a website called PeggingDates. I opened the site and saw that this was definitely a site where you could meet women who are into the act of pegging.

I opened the registration page and saw that the first month on the site was free for new users. But after the first month I would have to pay to have my profile on the site. Regardless, I decided to try it and created a profile with the id curiousguy96. It asked me to upload a picture, which I was a bit hesitant on. So picked up a picture where you couldn't see my face completely. I was wearing sunglasses and beanie in it so my face kind of looked obscure. I filled out all the necessary information and began to look at the profiles of all the girls on the site.

I sent some women 'flirts' and some messages to women who looked hot. Then I came across a profile with the bigcockgal9. The profile picture on the browsing page showed a young brunette woman, probably mid to late 20's. The picture was hot. It was just her face with a 'come hither' expression with her tongue sticking out and licking her lips. I had an instant hard on.

Her profile showed that she was online! I opened her profile to read what she had written in the description section.

Kinky Beautiful Woman Looking for Guys to Peg.

I'm all woman, but I wear the Pants & the COCK in the bedroom. I like a man who isn't afraid to be on his knees sucking my dick before he gets on all fours and takes it like a bitch.

IS THAT YOU?

ARE YOU READY TO GET FUCKED?

NEWBIES ALSO WELCOME.

Unlike any of the other profiles, she had a couple of pictures in her gallery. I instantly clicked on it to see what pictures she had. Once I opened the link, I saw her sporting a pair of sunglasses, wearing a black t-shirt that read LET'S TRY ANAL and a big black strapon cock.











If I was hard earlier, then now my dick practically wanted to burst out of my pants. It was the last picture that I saw that was the sexiest of them all.



She was absolutely stunning. And that smile of hers, as she showed off that big black strapon, told me everything I needed to know. This was the girl I wanted to take my anal cherry.

I immediately sent her a private message introducing myself and telling her that I was interested.

Hi,

I'm Justin. Just saw your profile and your pictures. You're hot!

I'm a newbie and I am looking to have my first pegging experience.

If you're interested, I would love to hear from you.

I was a bit nervous about being so forward, but I quickly hit the send button and waited for a while to see if I got a reply.

I must have waited for atleast 30 minutes but I didn't receive a reply. Thinking that maybe she checked out my profile and wasn't interested. I felt a little disheartened and logged off and went to bed.

*-*-*

In the morning, I turned on my computer to check my emails. After that I logged into PeggingDate to see if I had any replies. I was a little disappointed to see only 1 message, but was pleasantly surprised who it was from when I opened my inbox. It was the same girl that I had messaged last night.

Hey,

I love newbies and turning them into complete strapon sluts!

Do you have any other pictures I can see? They don't need to be nude, unless you want to send me nudes. ;)

Anyway, get back to me whenever you can and let's talk.

Xoxo Rebecca.

She wrote back to me. I was so excited about it. That I immediately wrote back.

Hi Rebecca.

Thanks for getting back to me. I thought maybe you wouldn't be interested.

Anyway, I am attaching a picture of me.

Justin.

I attached a recent picture of me and sent it to her. I went back to facebooking and a couple of minutes later heard a ding noise on my computer. It wasn't on facebook and the only other page I had left open was PeggingDate.

As soon as I opened the page, I saw an instant IM on the chat feature. It was from Rebecca.

Rebecca: You're cute!

I instantly replied back.

Justin: Thanks.

Rebecca: How old are you?

Justin: 21

Rebecca: You're younger than me. I like it.

Justin: How old are you?

Rebecca: I'm 28. Is that ok?

Justin: Yes!

Rebecca: LOL!

Rebecca: What do you do?

Justin: I'm attending university.

Rebecca: Ooooohh. College boy. Nice.

Justin: What about you?

Rebecca: I run my own business.

Justin: That's nice.

Rebecca: So you have never taken it up your ass ever?

Justin: No.

Rebecca: So why do you want to do it?

Justin: I've seen the porno's. And it's turned into a fantasy.

Rebecca: Is that the only reason you want to do it?

Justin: I don't know.

Rebecca: You don't know?

I began to get a little intimated. Honestly I didn't know what to say. I sat there trying to think of an appropriate response to such a question. Was it just because I was horny? Or was it because I wanted to experiment?

Justin: I guess I want to see what it's like for the roles to be reversed and be on the receiving end. I want to see if it feels good. To experiment.

Rebecca: Good answer!

Justin: Have you done it with a lot of guys?

Rebecca: LOL. Wouldn't you like to know.

Justin: Actually I would. : - )

Rebecca: I have a few bitches.

Justin: Wow.

Rebecca: I love to hear them squeal as I ream their ass.

Justin: Double WOW.

Rebecca: LOL. I bet you're hard right now.

Justin: Yes!

Rebecca: Do you want to be my ass slut?

Justin: Yes!

Rebecca: Yeah? Do you want me to slap my cock on your face and force it down your throat?

Justin: Yes!

Rebecca: Do you want to take my dick like a good whore and be my little bitch boy?

Justin: YES!

Rebecca: Good.

Justin: : - )

Rebecca: What are you doing on Sunday afternoon?

Justin: Nothing really.

Rebecca: Good. Be online Sunday morning at 10am.

Justin: Ok.

She didn't reply after that. She had probably logged off and I would only be able to talk to her next on Sunday. I logged off myself, turned on one of my favorite pegging videos and jacked off.

*-*-*

It's Sunday morning and it felt like an eternity has passed. I logged in at exactly 10am, but there was no message from Rebecca. I felt a little disappointed but stayed online just in case. Just as soon as I logged into Facebook, my daily ritual, I heard the familiar ding on my computer. I checked and saw that there was a message from Rebecca.

Rebecca: Hey.

Justin: Hi.

Rebecca: I thought you wouldn't be here and that I'd scared you off. LOL.

Justin: No. Infact I logged in exactly at 10am.

Rebecca: Good boy.

Justin: : - )

Rebecca: Do you still want to get fucked?

Justin: Is the sky blue.

Rebecca: Good. Are you free at 3pm?

Justin: Yes. Why?

Rebecca: Do you have a car?

Justin: No. I usually take a bus or a cab. Why?

Rebecca: How soon can you get to the Dubai Investment Park area?

Justin: You want to meet? Today?

Rebecca: Don't you want to get fucked?

Justin: I do.

Rebecca: Good. So...how soon can you get to the DIP area?

Justin: If I come by cab then it shouldn't take longer than 10-15 minutes.

Rebecca: Good. Download the PeggingDate app on your phone. IM me when you're entering the area. I'll give you the address.

Justin: Ok.

Rebecca: What's wrong?

Justin: I didn't know we'd meet so soon.

Rebecca: It's ok to be nervous. I'll take good care of you.

Justin: Ok.

Rebecca: Are you having second thoughts?

Justin: No. Just as I said earlier. Seems too fast and too good to be true.

Rebecca: I'll be away for the next couple of weeks and I'm horny.

Justin: ok.

Rebecca: Are you sure?

Justin: Yes.

Rebecca: Good boy. See you later.

And she logged off. Wow. That was so fast. I can't believe that I started talking to her a couple of days back, that too just once and my fantasy was about to come true.

*-*-*

It was almost 3pm and I was in a cab entering the Dubai Investment Park area. Once I got there, I turned on the chat app I had downloaded earlier and sent Rebecca a message.

Justin: Hey. I've just entered DIP.

I waited for a couple of seconds and Rebecca replied.

Rebecca: Good.

Justin: : - )

Rebecca: There is an apartment complex called Terrace Apartments near the Courtyard Marriot Hotel. The driver should know it. Get off there. Come to block B. Ring the buzzer at the door for 501 when you're there.

I gave the driver the location and we arrived there shortly. I paid the cabbie and walked to block B of the building. I was a bundle of nerves, but somehow I managed to press the buzzer for apartment 501.

The buzzer hissed and I heard a female voice.

Yes?

Hi. It's Justin.

Come on up.

The buzzer buzzed again and I heard the door unlock. I became even more nervous as I walked into the lobby and waited for the elevator. I got upstairs and found myself in front of Rebecca's apartment. I waited for what seemed like an eternity and then I heard the clicking of heels approaching on the other side of the door and my heart began to beat faster than it ever had.

The door opened but there was no one behind it. I walked inside and heard the door behind me close. I turned around and my jaw dropped as I saw Rebecca, in a robe which was left open showing off her magnificent breasts and a black strapon dangling between her legs. She had a devious grin on her face.

"Hey there slut boy."

"Ummm....hi..." was all I could muster to say as I continued to stare at the beast of a dick that hung at her pelvis.

"Like what you see?"

"Uh....th-th-that's a big dick...."

She must have sensed that I was pretty nervous, because she moved closer to me putting her hands on my crotch, as the dildo rubbed against my pants. She leaned into me and whispered in my ears, "Don't worry slut, I'll take good care of you."

She caught hold of my hand and led me into a spacious living room. Her apartment was huge. As I walked in, I saw a huge couch set in the shape of a U that was built in the middle of the living room attached into the wall. It could easily seat anywhere from 8-12 people, with a coffee table in the middle. Right across from the couches I saw a big TV on the wall with an entertainment system.

I turned to face her and saw that she was stroking her strapon.

"Come here," she said.

I moved closer to her. She grabbed me and we began to kiss. She was a really good kisser and she moved her body into me as her lips mashed with mine. I could feel her dildo rub into my thigh again as our kiss lingered.

"Do you want to touch it?" she cooed.

"Y-y-y-yes."

She just smiled and took my hand and put it on her cock and leaned into me and kissed me again. It was a strange feeling to be stroking a fake dick. The dildo was made of a rubbery silicon material and although it wasn't a real dick, Rebecca moaned as we kissed.
"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.

*-*-*