Pegging Fantasy Weekend Pt. 01

Story Info
She makes my first time memorable.
1.9k words
4.4
44.9k
40
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

It started as a fantasy, one I would have never imagined I would enjoy, but has been a curiosity for some time. It began with pictures, then research, then videos. Now, it had happened, and I would never be satisfied without it. As I was driving home from the airport, shifting in my seat, I smiled as I thought back on how this unforgettable weekend all started...

My erection was growing from the video of a sexy woman strap-on fucking a guy. Her sexy curves, glistening with sweat as she drove her hips back and forth into his ass. The rhythm accentuating how absolutely beautiful she looks. The look on her face, one of pure and confident pleasure, is what I want to be able to give a woman. The guy seems lost in his own pleasure, probably from the pressure on his prostate. Next, I decided just to search for pictures of girls with strap-ons, and stumbled upon a bunch of profiles (on an unnamed social networking service). It made sense to start a profile and look around, since the initial search brought up a nice amount of content. That's how the fantasy of being fucked by a girl turned into a reality.

As I scrolled down the various blogs, a picture started to get me excited from the start, an amazing set of tits with erect nipples followed by a toned stomach ending with red sweatpants. Her body is perfect and I start to envision exploring her body with my tongue. Then comes another picture, same build-up, but this one see is grabbing in her pants. Now a group of pictures follows, showing her bringing the strap-on she is wearing out and playing with it. These photos would be in my head for days.

After searching through her blog, I see that she has meet and pegged users on this site before, and even posted looking for someone. It's a longshot and I wouldn't expect a reply, but knew she could be worth it. She lives in a different state, but I offered to bring her to NY and get a hotel room in her name, so she could take my anal cherry. To sweeten the deal, I see that she is a hockey fan so I offer to get tickets to MSG for a game, and pick the weekend her team is in town. Realistically, I never anticipate that I would get a response.

When I got the notification that I had a reply, I got a little excited. It came while I was at work, so I had to wait to check the message, since this is NSFW. As I left work, I immediately checked the message in my car... She said "Yes" and to send her my number, which I did immediately. A couple minutes later, as I walked in my apartment, I received a text with a picture. It was a photo of her with her strap-on and a look that said "Come here". Next, she called and we hit it off right away. There was something in her voice that made me feel comfortable with her, and I assume the reverse was true, as she wanted to talk about the arrangements.

As I stood in the airport, holding a sign with her name, as instructed, I started to get a nervous excitement. I noticed the sweatpants first, bright red made her stand-out of the crowd, and I could not believe how beautiful the woman walking towards me was. Lost in her beauty, it wasn't until she game me a hug, that I regained my wits. I took her bags and we started to walk to the car. We stopped for her to go to the restroom and were off.

While driving, we talked for a little until she grabbed my right hand and places it on her knee and slowly brings it up. That's when I felt the strap-on she had on. She leaned into my ear and whispered in a voice that gave me goosebumps, "I can't wait to bend you over and fuck you."

Moving through the hotel lobby with an erection, we quickly made it to the room. When we get inside, she tells me to undress and wait on my knees at the edge of the bed as she gets ready. As instructed, I wait till she returns, it feels like hours but was only minutes. She comes out and gets on the bed in front of me. I am utterly consumed by how sexy the woman in front of me is, standing naked except for her strap-on.

She positions herself in front of me at the edge of the bed and spreads her luscious legs wide, exposing her perfect pussy and ass. Her pussy is glistening.

"That was a long flight and I need my attention" she says. "Let's start by you getting to work."

Unable to hide my excitement and without pause, I slide my tongue from her asshole up to her clit, then start to slide my tongue in and out of her pussy to get her juices flowing. Then I moved up to her clit and draw her into my mouth, sucking on her clit. She grabs my head pulls it harder into her pussy, her body grinding into my face. The strap-on resting against my forehead. She lets loose an orgasm, but I do not stop sucking her clit, until she tells me to tongue her ass. I happily slide down and flick my tongue into her ass, then drive my tongue in and out of her until she is cumming again.

"Mmmmmm, good boy. Now you have earned your reward and I'll start gentle."

"Bend over the bed." she says devilishly.

"Thank You Miss" I say.

She comes up to me and spreads lube up and down her girlcock in my face.

She positions herself behind me and rests the tip of her cock against the opening of my virgin ass. "Are you ready to pop your cherry? After this I will own you forever."

"Yes Miss, I am ready"

She positions herself behind me. "Are you sure this is you are a virgin?"

As I start to respond, she plunges the head of her cock into my ass. Stretching my ass open for the first time.

"Not anymore." she says, while sliding the first inch of her 6 inch cock into me. Thankfully, she gives me a minute to adjust, and slowly inserts more and more of her cock. The initial pain is starting to be replaced by pleasure. She asks if I am OK. I tell her I am and she slides the cock out and in all the way to the balls.

"Good Boy, taking my cock. Let's see how much you can take."

Before I am able to process that last comment, she start to drive her hips back and forth, pushing her cock in and out of my ass, slowly gaining speed. She grabs my hips with both hands and thrusts her girlcock deep into my ass, leans in and says:

"We are going to keep going until I make you cum just with my cock."

"Anything you'd like, Miss. Please Fuck Me!"

"Oh! He likes it! Did I find a new butt slut?" she says as she thrusts harder and faster into my ass.

"Yes Miss, I am your butt slut."

She continues to pound my ass for what felt like an hour. It felt so good, I could not believe it. She told me to flip over so she could see me cum. Excited to be able to see her incredible body as she drives her cock into me, I quickly turn onto my back.

She gets in position and drives into my ass, thrusting her hips up to my ass. Driving me to the brink of exploding.

"I'm going to cum" I say and she starts to fuck me even harder, leading to the best orgasm I have ever had, but she does not stop fucking me, yet. My body is shaking from the rippling orgasm rushing through me. Finally, she slows down, and withdraws her cock. She begins licking up my cum, until it is all in her mouth, then leans in and kisses me with a mouthful of my own cum. The first time I have tasted my own cum, and I would do it again for this goddess.

As I lay there in bliss, she goes to her bag and pulls out a couple things. When she gets back to the bed, she leans in and gives me a deep kiss, then whispers into my ear, "We're not done yet, my toy. That was just the warm-up. Be a good boy and flip over for your Miss."

The size of her new girlcock catches me by surprise. It was so sexy, my cock started to come to life. The look in her eyes made me want to do anything for her, and I quickly flipped on my stomach. She put restraints on, which tied me to the bed, face-down and spread-eagle. She lines up between my legs, with her girlcock between my cheeks. She leans over me, pressing her breasts against my back, I feel her perfectly hard nipples against me as she says, "That first one was for you. This one is for me. If you take it like a good slut I will reward you next, but if not..."

"I will be a good slut, Miss. I would do anything to please you."

"Thanks what I like to hear, slut."

She leans back and lines up her 8 inch cock, thicker than the last, and pushes her way in. The tip pops its way into my ass, stretching my ass. I bite the bed in front of me as she drives the rest of her cock all the way into my ass. Holding it there. She leans back over me, resting her weight on my back. The feel of her skin and touch, relaxes me. She starts to kiss my neck and play with my ears as she grinds her hips back and forth. Each thrust causing me to moan. One makes me scream out and she stops.

"Don't make a sound, remember?" she says as she raises back to her knees. "I'll show you a taste of what happens when you don't listen."

She slides out of my ass, then drives her hard rubber cock deep into my ass. It takes the wind out of me, but she draws almost all the way back out and drives her hips as hard as she can, pounding my ass. She stops and asks which did I prefer?

"Whichever makes you happy Miss. Fuck me any way you like. I am yours."

"I like that, slut." she says and begins pounding into my ass, harder and harder. The pleasure it was giving me physically and to hear her grunt as she pounds my ass was unmeasurable. My cock started to grow. I could hear her get close to having an orgasm from the pounding she was giving me, which only turned me on more.

"You're going to make me cum, slut." she moans, driving into my ass until the orgasm hits causing her to shake with her cock inside me. This motion, brings me over the line and I cum with her.

She removes the restraints and asks me to turn onto my back. Still trying to regain myself, it takes a second for me to notice that she has moved over me and lowers her glistening pussy down to my mouth. "Get cleaning" She says.

Eagerly, I lick her pussy until she is fully satisfied. The taste of her overtakes me, and I will never forget it.

She kisses me deeply and tells me how much she is looking forward to tomorrow, then we fall asleep in each other's arms.

Too be continued...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
FindingnewexperienceFindingnewexperiencealmost 7 years agoAuthor
Part 2 in development

Stay Tuned

akeyesxakeyesxalmost 7 years ago
Waiting for more...

Both he and I are waiting for more of this story. And if it was me that was he...I'd be waiting with great anticipation. Did you write a Part 2? We'll see.

legsfeettoeslegsfeettoesalmost 7 years ago
Looking forward to it

Susan, I'm waiting for you!

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
The Best Present: Pegging my Man A wife discovers her husband is curious about pegging and….in Fetish
Exploring Sexuality: A Pegging Husband is pegged by sister-in-law with wife's permission.in Anal
Easy First Date Girl uses strapon to peg a boy.in Anal
More Stories