Have You Ever Been Pegged?

Below is the story of how I met her, how I experienced it, moment by moment:

"Hi, I'm Maggie. Have you ever been pegged?" That's the way she started a conversation with me. The words were totally bizarre, especially coming from the smoking hot babe with mysterious eyes at the bar.

"Quite an icebreaker." I answered. Then we talked for the next couple hours and we really clicked. I loved her raunchy personality and she said she loved my strong shoulders.

When the night wore thin she complimented my arms and abs then asked me to stand up and spin around so she could see my buns.

Then she said it again: "Have you ever been pegged?"

She said it again when I was mid sip and I spewed my beer all over. "You're really asking? You mean when a ...does a guy...from behind, like a man... with a?"

She nodded seductively and I knew she was serious. Looking her up and down I grinned, "What's in it for me?"

Her answer was straight to the point and exactly what I needed to hear to convince me, "You let me do what I want to you, and then you can do whatever you want to me."

She had slim hips and a tight ass. Her boobs were just maybe surgically enhanced and that was fine with me. Her long bottle blond hair and influencer makeup pushed all my buttons.

I slammed my beer on the bar, "Let's go!"

"Not so fast buster. You spit beer on me. Now you go wait over there for me while I clean up."

Standing in the vestibule I barely had reservations about what we were about to do. Taking a dildo up the ass would be a small price to pay to get a piece of her. I wouldn't care if it were fifteen inches of thick black silicone monster cock.

Or maybe it would be rubber, hopefully not metal like the infamous Steely Dan. I didn't care, or at least I didn't think I cared.

Nights like this were what made this my favorite bar for a little side action. Much needed side action 'cause my girlfriend never gave blowjobs and never tried anything new.

When she came back she placed her bent arm in mine leading me to the parking lot. With a chirp her car announced that it was unlocked. "Get in," she said, "And you better buckle up. I'm wild."

In her apartment she went straight to the bathroom, leaving the door open. I heard the piss hitting the water and she yelled out to me, " I want you face down and ass up when I get out there."

I was already half undressed when she said it, so I literally dropped the rest of my clothes, and my phone, and assumed the position she commanded. My cock was rock hard and throbbing in anticipation of the night to come.

Looking back past and between my legs I watched her approach me. She was completely and magnificently nude. Her jugs were every bit as firm as I'd hoped and I gazed at them too long. Her nude legs were long and tanned - deeply tanned like she spent a lot of time in the booths. My heart throbbed in anticipation as well as my cock.

I couldn't quite get a good view of her strap-on. I only saw that it bounced and was blue. But then the reality of my situation started to give me some little trepidation - "So how big is it? More than ten?"

She laughed, "Oh no it's pretty harmless. You're gonna do fine, Champ!" She slapped my ass with a resounding whack. I hoped it didn't leave a lasting mark which I would have to explain to my girl. Or maybe a mark would be the reason I was waiting for to end it with her.

The crazy woman I allowed to bring me home climbed up on the bed behind me, running her long acrylic nails along my ribcage.

From the first moment her knees hit the mattress she was a talker: "Ohhh, You look so studly and hot with your bum lifted to welcome my invader." She seemed to get off on some power trip - penis envy?

When she crouched over me to bite my neck I felt the artificial tip of it graze my balls. My lover cooed, "You're so hot under me. I could kiss your sexy back all night."

I looked through my legs again and could just see the blue latex tip waiting for her to lift it to my virgin hole. I didn't know how long it was, but based on what I saw of the end, it wasn't too thick. Well not compared to the novelty ones I'd seen for sale in the dirty bookstore.

I laid my head on my arms and took a couple deep breaths to relax. I waited for the pain - instead she kissed me from my shoulder blades, all the way down my spine, and then all the way to my crinkly hole.

I heard a deep inhalation, "Mmm, Honey, you smell fresh and earthy."

I was embarrassed to have another human smell me *there*, but comforted that she wasn't offended.

It felt awkward to thank her, but that's what I did. I thanked her for complimenting my ass's odor.

I'd never been kissed there before and the feeling of a warm wet tongue drove me insane. She licked and swirled and even dabbed at my private orifice. I knew she was preparing me for anal just like I'd prepared sluts before. It didn't matter as I mewed, "Yes. Yes, do me back there."

She strangled my hanging nuts firmly, pulling harder than I thought I would like. But I did like it. I felt submissive and feminine allowing her to manhandle my package.

Then one finger snuck it's way from my balls to my asshole. Based on its thickness I think it was a thumb. "I can tell you like that." She said with a smile in her voice, "Are you sure you've never been pegged?"

Sitting back she rubbed that thumb roughly on my entrance while reaching for something. My fears were allayed when I heard the lid of a tube of lube click open. She continued her line of thought, "Well no matter. I'm gonna fuck you really good, Sweetheart."

Slicked up, her thumb went in me pretty easily. Two fingers took more work on her part and more patience on mine. By the time she was done, three fingers were buried up my ass and I'd gone past discomfort into a tense acceptance.

I kept my eyes closed, willing myself not to notice any details about the room in which I was being violated.

In contrast, Maggie's eyes were glued to my ever stretching ring. She growled lowly, "Seesh, the sight of your gaping opening makes my clit throb." I imagined her clit being stimulated by the other end of the dong.

Briefly she fondled my cock and balls again but I seemed to have lost my erection and I felt emasculated not to be hard.

Next both hands grabbed me roughly by the waist. If you can believe it, my first worry was whether or not she'd wiped her fingers beforehand.

My little dom squealed, "Hardly any guys let me do this. I'm gonna reward you big time if you're still up for it when I'm through with you."

Of course I'd be up for it. This was the hottest thing that's ever happened to me.

I felt the unknown sized rubbery phallus being lifted into place - ready to spear me. She again uncapped the lube, pouring streams of cold liquid on my defenseless backdoor and her menacing soldier. "Ready or not!" She chuckled.

The sensation of the fake material was unmistakable when it touched my rosebud. With one hand she pressed it against me and it started to go in agonizingly slowly until suddenly, while she was pulling on my hips, there was a pop.

That pop burned and hurt like a sunuvabitch. After my long stoic silence I broke the mood in a panic, "Stop! Don't move!"

But as quickly as it started the pain subsided. The damage was done. By now the tip of the dildo was wedged in me. My voice trailed off as I remembered my promised reward and her enticing body, "oh nevermind. You can keep doing it."

The vixen assured me she was taking it slow but it felt more like she was adding an extra foot every second.

When she finally and gleefully announced she was all the way in I felt her smooth pelvis grinding on my buns.

Enjoying the complete impalement of her unnatural cock up my chute, her soft legs were entwined with my hairy ones and she played a sexy game of footsie, caressing my toes with hers.

She practically sang, "Darling I love being here in you. I could stay like this all night. It's almost a shame to start the action." But saying that, she did start the action. My Megs pulled out slowly and re-entered me slowly again before increasing her tempo.

She fucked me with four or five long strokes before pulling completely out again. Sitting back on her haunches she gazed at my abused anus, "Incredible how it doesn't snap back to its original size!"

Worried that my ass was permanently deformed my body shook, "Never fear." She told me. "It will. Just not until you get up and walk around a bit."

I heard a loud snap, like surgical gloves being ripped off, then saw a condom flung onto the nightstand with a splatter. It sat there, a blue lump of latex in a puddle of mixed lube and ass juice. I pondered that it was my ass juice seeping into the woodwork.

The savage girl who begged me to let her peg me in exchange for an unlimited access to her fine body resumed assaulting my rectum, and I took it.

She plunged her male-like appendage into my depths with renewed vigor. Building to a crescendo she pounded my ass grunting and panting until finally she fell on my back in an exhausted climax.

The warmth of her tantalizing body on mine was a wonderful promise of what was about to be. Reaching under me without withdrawing, she massaged my timid organ back to life.

Eventually she fell out of me just like any man would once spent. She produced two wet washcloths, and with one, cleansed my forsaken shitter, then wrapped the other around her tool of destruction, cleaning it as well.

Rolling over she sighed, "I've got to thank you Big Boy. You've been the best fuck I've had in forever. You've earned your payment and now my body is yours to do as you like. Use any hole, pose me any which way, or run for the door. The choice is yours."

Confused, I rolled over too, being careful of my overexcited cock. At last I could totally take in the vision of her sublime perfectly female form.

Her breasts were huge, spectacular, and definitely not real. Her waist was thin. Her hips were straight. Her legs were long. Striped red and silver painted toes reminded me how unpredictably feral she was.

I couldn't see the harness but the strap-on lay there under the washcloth, against her pussy.

Her arms were splayed above her head and I saw that she'd shaved her pit hair into a design, really an impressive work of art. I had to see what she'd done with her bush. I expected more piercings to match the others on her wicked body.

Slowly I peeled the terry towel from my goddesses body to reveal a surprise.

There where I expected an artistically adorned pussy, instead I found a large soft manly dick. It was uncircumcised but very very humanly real.

There was no mistaking the moist flesh of a cock in post orgasmic glory. A little pearly drop still slipped from the end.

My bewilderment turmoiled around me, swirling in my mind and body. How could this be? This amazing Aphrodite posessed a real penis rather than the fake one she had reamed me with.

I was sure I'd seen it bounce plastically when she'd come out of the bathroom. I knew I'd felt the latex texture rub on my balls.

In agitated puzzlement I looked back to the nightstand. There the confounded blue rubber sat in a heap, mocking me.

I'd seen her fling it there. I'd known she took it off and subconsciously I must've known that it was the blue flash I'd glimpsed earlier.

The fog lifted, giving me the clarity to know I'd been fucked with a real live penis. By a real live man?

I glared back at the fleshy tube of man meat unable to pull my eyes away. It looked like mine. Thick but shrinking and returning to its pliable form.

I'd been injected by this cock! My fingers flew to my battered sore hole where I felt the gooey slime leaking out of me.

With a feeling of shock and betrayal I looked to her face, but her smile was so alluring and angelic I couldn't be upset.

Afraid of her answer I asked, "But you said you were going to peg me?"

She explained her deceptive thinking with a mischievous smile, "My names Margarite...or Maggie...or Meg...or Peggy. So I Pegged you."

Her smile faded briefly and she implored hopefully, "Do you want me still? Because if you do, my offer still stands. You can do anything you want to me. Any depraved desire you harbor and you can have it."

And I did have sick desires. Desires I'd never admitted to anyone before. Desires strong enough to forget how she'd tricked me. Long repressed urges I thought would never see the light of day. Dreams I knew that she of all people would not scorn.

Still holding the washcloth I finished washing her shrunken dick clean of all my filth, "Do you think you might rape my mouth too? I mean, can we pretend that you force me to suck your cock?"

Her face lit up, practically beaming, "I'd be happy to. I'll make you my plaything. Call you my slut."

I explained more, "Can I be your niece and you be my uncle? Can your voice sound like a man's again?"

I knew what distant trauma still haunted me but it didn't change the fact that this was what I wanted.

This womanly man I'd only known for a few hours grabbed my head roughly, forcing my face down to her crotch. My adult lips came into contact for the first time with a cock and balls.

Then rolling over on top of me she maneuvered the end into my resistant lips. And in a husky manly voice said, "Come on girl, if you make me happy and I'll buy you a treat."

I kept my eyes shut so as not to break the illusion as my mouth was forced to accept a cock. It plunged in and out, reaching the entrance to my throat a few times.

Gagging, I sputtered and objected, but I pulled the owners hips, driving it deeper still while I sucked madly.

It took a long time since it was this cock's second come, but finally I was rewarded with a mouthful of thick creamy spooge.

I swallowed it all, only coming up for air when no more nastiness dribbled out, "Man! That was the best. I'm so glad I came home with you."

Cradling my head, with her cock softening for the second time, but pressed luxuriously against my face, she replied, "You still haven't cum yet. How can I make you even happier?"

I stayed on my back. But pushed her down my body. I asked her if she would ride me. "I wanna see your perfect boobs when I fill your amazing ass with my seed."

I've fucked ass in the cowgirl position before. But to do it while a clammy hunk of dick jiggled about was going to be a new high.

She lubed her ass and my stiff cock then proceeded to impale herself on me. My pole eased itself up into her with much less trouble than hers had gone into me.

A minute later and she was bouncing up and down screaming profanities. I fondled her cock, then her balls and was pleased to feel it grow hard again.

Then I grabbed her melons squeezing them hard. I couldn't decide if I preferred touching her top or her bottom: it all turned me on so much.

In the end, when I came, I had one hand jerking her cock and the other twisting a pointy nipple.

I screamed too, bucking up wildly, deep into tight Hershey Highway, then let loose with a huge load. It flowed out leaving cummy streaks on my pole. She knew just how to milk my dick, neither getting too intense nor neglecting my orgasm.

She sat down on my cock letting me enjoy the afterglow before disengaging.

I held her close and we both shared how special the night was.

When I was getting dressed I got a text from my girlfriend: "By now you've figured out "she" isn't a she. Hope you got what you deserve."

Perplexed, I showed it to Maggie who asked what my girl looked like. After I described her she told me that my girl had paid her fifty dollars to talk to me. We both agreed that we were ecstatic that I had been tricked.

To get back at her we sent her a picture of Maggs posed seductively on her bed in hot lingerie with the caption, "Even with a cock she's hotter than your fat ass."

Next we sent a picture of me dressed in Maggies lingerie with the caption, "And she let's me try new things too."

I've met up with Maggie periodically when we've wanted a fun time and I learned to love being fucked by her cock or sucking her off when I wasn't busy using her hot body for my own pleasure.

Naturally my girl and I broke up. It was a stale dysfunctional relationship that should've ended long ago.

Author's note:

If you liked my story please give it a good rating. Add it to your favorites to read later if you want. Follow me and you'll see all my stuff.

I try but don't always succeed in creating a good story. Please add comments so I know what I'm doing well and what to improve on. If you want to talk I'll answer your friendly comments.

I often attempt to create tension in the main character's motives. In turn, this often means that characters in the story have flaws and might not even be nice to each other all the time.

I really appreciate polite comments!