Pegging Tales: Justin's First Time

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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.

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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.

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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.

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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.

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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.

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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.