Truly Dirty Double Penetration Stories: My Filthy First Time

After over a decade of working in the sex industry, I’ve amassed quite the collection of downright filthy double penetration stories. But few can compare to my filthy first time.

It took place at a German brothel I was working at. Divided into several small, apartment-style rooms, we would be picked by the punters before discussing the prices and services.

It had been a particularly slow week for us in the lead-up to Christmas. People were naturally spending their money on Christmas presents rather than paid-for pussy.

As we sat around on the red velvet chairs sipping coffee, chatting, and browsing through our phones, the Madame of the bordello, Sonya, made a very indecent proposal.

“My tits bounced wildly, my mouth had formed an O-shape, and the room was filled with the slap of skin-on-skin, the farting sounds of rough anal, manly grunts, and feminine squeals.”

She had just received a phone call from two English-speaking tourists. They wanted a double penetration experience with a busty girl later that evening.

“So, who wants to take the job?” Sonya asked us bluntly whilst dismissing the small-breasted girls who volunteered.

I’d been fucked in the ass more times than I could count, but I’d never tried double penetration. I had the big tits to match their desires.

Plus, I needed the money. Double penetration sex paid very well, and christmas wasn’t the time to be picky about clients. How hard can DP be? I thought.

“I’ll take it, Sonya,” I said bravely, much to the distaste of the smaller-breasted girls who’d be turned down.

“Good girl. I’ll go and confirm with them.” Sonya said in her classic no-nonsense German tone. “In the meantime, douche yourself and prepare. DP can be a rough job”.

Note: Sadly, no photos were taken of this double penetration story. But to keep you entertained, I’ve included some amateur DP sex pics from my friends. Enjoy!

The DP Duo Arrives

After shaving, douching, and picking my slutty outfit and with little else to do in the bordello, I spent the rest of the afternoon watching classic DP porn for inspiration.

To prepare myself, I’d slid a large metal plug inside. As I watched the hardcore double penetration porn, I couldn’t help but move it around to stretch my asshole in anticipation.

Before long, the aggressive buzz of the brothel door rang through the halls. The DP duo had arrived. I will admit, that the fear of the unknown was making me nervous.

I listened at the door as Sonya welcomed them inside. I checked my makeup and outfit in the mirror, confirmed I looked seriously fuckable, and went to meet them.

Interracial double penetration sex stories

“Well, hello, boys!” I said with a dirty grin whilst greeting them with a hug. “I believe you’ve got two early-Christmas presents that you want to drop down my chimney?”

The men laughed loudly, and I could tell they’d had a bit of Dutch courage before coming here. Their names were Dean and Mark, two British tourists visiting Berlin for the week.

“Have fun!” Sonya called after us as I led the men to my erotic boudoir. Once inside, I got the payment out of the way, covered the rules, and asked about any requests they had.

“We want the proper pornstar experience,” Dean said boldly.

Without saying a word, I leaned in and stuck my tongue down his friend’s throat whilst making loud porn moans.

“Like that, baby?” I asked with spit all over my mouth. Both of them were now rubbing their cocks through their pants. “Get naked and show me your cocks!” I shouted.

The First Of My Many Double Penetration Stories Begins

Time is money, and I waste no time in getting to work on the two erect fucksticks in front of me. I switch between the guys, making the loud porn noises that they asked for.

Suddenly, Mark pulls away and rudely prys my stocking-clad legs apart to reveal my meaty pussy that’s already glazed with a layer of wetness.

“Oh, mate! You’re one dirty fucker!” Dean laughed as Mark buried his face in my prostitute pussy. He sucked like labia and clit as hard as I was sucking his friend’s cock.

I moaned like a whore into Dean’s veiny meat as Mark’s tongue slid in my love-hole and yanked on the butt plug still lodged in my ass.

But I squealed with delight when he slid the plug out, switched things up, and started riming my smooth asshole.

“This guy is fucking hungry, right?!” I said breathlessly as a few ropes of spit dripped down onto my plump tits.”Leave something for your friend to suck on!” I laughed.

But there was enough of my sleazy flesh to go around. Dean slid his cock out of my mouth and ravaged my tits with his mouth.

The feeling of two strong men’s tongues worshipping my body was orgasmic. It gradually wiped away any apprehension of double penetration.

“Have you ever been fucked by two guys at once before?” Mark asked me with his voice muffled inside my pussy.

“No, you two are the first,” I said before kissing Mark and shoving my tongue down his throat. “I was nervous at first, but now I can’t fucking wait!”

“Fucking love it!” Mark shouted, “I can’t believe we’re taking your DP virginity. Don’t worry; we’ve done this many times. You’re in good hands!”

Spitroast Warm Up

The men had booked for an hour and knew how to use their time. As I slapped a layer of lube on my asshole and pussy, the guys requested I get into the Doggy Position.

Mark took the back whilst Dean took my mouth. I went to work on his cock and slurped up the pre-cum leaking from its tip. Behind me, Mark cock to work.

I felt his cock slide balls-deep into my pussy as my throat devoured the cock t the front of me. As I was penned between these two horny guys, Mark began fingering my asshole.

The plug had done its job, and Mark could easily slide three, then four, fingers inside me and massage the tip of his cock through my vaginal wall.

“Oh, mate! You need to feel this ass of hers. It’s like fucking silk!” Mark said excitedly as I roared in sexual ecstasy. “Fuck this; I’m going in!”

My pussy was left neglected as Mark’s freshly-lubed dick glided along the soft walls of my ass. I released that deep, guttural moan that comes with any cock going in your ass.

After a few slow strokes, Mark used my asshole like it was a pussy. I gripped the shaft of Dean’s dick for support as his balls smashed against my wet pussy.

“How is it?” Dean asked casually with his hands resting on the back of his head whilst his cock was serviced.

“Fucking immense, mate! Not too tight, not too loose,” Mark said, discussing my body like it was an inanimate object. “I can feel her pussy leaking down my balls.”

“Oh yeah? Shit, I have to try this,” Dean said as he pulled his cock out of my mouth and looked me in the eye. “You’re leaking, huh? You’re loving this, aren’t you, slut?”

“Yes! Yes! I was born to serve cock boys,” I shouted, causing deepthroat spit to leak onto the red mattress below, “please fill my holes and make me your whore, I’m begging you!”

DP Tranforms Me Into a Silent, Squirting Mess

Mark slid out of my ass with a satisfying pop before lying down in the middle of the bed that I’d been fucked on countless times before whilst Dean moved behind me.

In reverse cowgirl, I slid my gaped asshole down onto Dean’s glistening dick and felt his balls’ hair touch my lower labia. My pussy was facing Mark’s quivering cock.

“Fuckkkkk me! I don’t know how long I will last here, bro!” Dean said from beneath me whilst reaching around and grabbing my tits. “Possibly the best ass I’ve ever had!”

“Incredible, isn’t it, mate? I don’t think I’ve ever seen a twat that inviting,” Mark said as he lined up his dick with my glistening pussy.

This is it, I thought; I’m about to experience my first double penetration. I was shaking with lust and excitement. Then, I felt Mark’s second pair of balls meet Dean’s.

The feeling of fullness that comes with double penetration is hard to explain. You feel as though you have three bodies. As the guys settled into me, they started moving.

Their combined movement felt like a steam train leaving the station. The momentum gradually built until I had two cocks smashing into me in the blink of an eye.

The momentum of a traction engine ravaged my holes. I wanted to squeal like a whore, but I couldn’t. The experience, the feeling, and the pleasure were simply overwhelming.

The guy’s heads were parallel with each side of my face. They reeled off their own sordid dirty talk in each ear, making my pussy leak and squelch under the cock inside.

  • “You’re like a human pin cushion, you little whore! Packed full of so much man meat you can’t even speak.”
  • “Look at those big, plump tits bouncing around. You were built for this!”
  • “You’ll never be satisfied by one man again; you’ll constantly need two, three, eventually even ten cocks just to have an orgasm, you slut!”

Initially unable to speak, I felt a violent orgasm building in my lower stomach. With the men unaware, their cocks ploughed into me regardless.

My pussy erupted in female ejaculate. It hit Mark’s stomach and dribbled down onto Dean’s cock below. The wet, slapping noise was unforgettable.

As the wet sensation hit the guys and the almost urine-like smell of female squirt filled the air, Mark looked down at my leaking pussy and then at my rolling eyes.

“Silent sex can be incredibly hot when all you focus on is your breathing and his breathing, and the sounds that your bodies make as they move as one.”

— Desiree Dean

“Fucking hell, Dean, she’s doing an exorcist impersonation here!” Mark shouted. The humiliation of these men mocking my orgasms increased the pleasure.

The hot breath of two men was like a double massage on my ravaged body. I lost count of the number of orgasms I had, both with a squirt and without.

As the men switched holes throughout, I regained my voice and returned their dirty talk tenfold, both in English and my native language.

  • “I want you to breed both of my holes at once, make my asshole pregnant!”
  • “Fuck my holes so hard that I can never have a normal boyfriend again. I want you to make my pussy a true whore’s pussy!”
  • “Fuck my ass so hard that I can taste the tip of your cock in my mouth!”

I had nowhere to go. I was truly trapped between these strong guys as they ruthlessly plunged in and out of my holes like I was a cheap toy for their pleasure.

The Most Beautifully Humiliating Moment Of My Slutty Career

Sonya, the German brothel Madame, was a love/hate character, not someone to be messed with. But she took care of the girls and gave respect where respect was due.

During longer sessions, she would discreetly pop her head into the room to ensure everything ran smoothly and the girls were safe. This DP session was no exception.

Sonya.

Sonya knew me as a woman who was feisty, able to stand up for herself, and quite dominant. The sight she saw when she opened the door changed everything.

I made eye contact with Sonya over Mark’s shoulder and watched as her gaze dropped from to my defiled holes filled with the cocks of men I’d met less than an hour earlier.

My tits bounced wildly, my mouth had formed an O-shape, and the room was filled with the slap of skin-on-skin, the farting sounds of rough anal, manly grunts, and feminine squeals.

“As the men pumped their cocks, I could feel juices from my pussy and leftover lube seeping from my ass onto the carpet below.”

Sonya smirked at the sight and flashed an ok symbol at me to confirm I was happy. Instead, I licked my upper lip, rolled my head back, and roared like a harlot.

That was all the confirmation she needed, and the door discreetly closed behind her. On a quiet day like today, every girl in the brothel could hear me being defiled.

Truthfully, this just turned me on even more. I felt like my first double penetration experience had lasted two minutes, but a knock on the door told me otherwise.

Sonya, or one of the girls, knocked to tell us we had ten minutes left. I could have let these guys use my holes simultaneously all day. But sadly, sex work is sex work.

The men heard the knock as much as I did and slowly pulled out of me. Now, I had two sets of cum-filled balls that I had to empty.

The Initiation of a DP Whore Is Complete

“How was that?” Dean asked me with a dirty grin.

“I can’t even… Words can’t describe.” I said dazedly before slowly lying back and spreading my holes, “how do my ass and pussy look?”

“Put it this way, love; you won’t be sitting straight for a few weeks!” Dean laughed. “I’ve proper gaped you open; I feel sorry for the next block who comes after us!”

My ass felt wider than it had ever felt before. With the men still pumping their cocks and their time running out, I dropped to my knees and pushed out my breedable tits.

“Finish what you’ve started and spunk all over my tits!” I instructed the men.

I sucked their cocks to lube them up with a layer of spit before rubbing my tender pussy intensely. I could smell the juices of my pussy ingrained in their pubic hair.

As the men pumped their cocks, I could feel juices from my pussy and leftover lube seeping from my ass onto the carpet below.

The first cock to erupt was Dean’s. Layer upon layer of hot, sticky spunk blasted across my mouth and tits. I was triggered when I got the first taste of cum.

“Ah, ahh, ahhh! Fuck! I’m gonna cum, you filthy little slut!” Mark roared.

After he sprayed his first rope of thick cum on me, I slammed my mouth over his cock until his pubic hair was level with my top lip.

His meat convulsed and pumped rope after rope of salty, white liquid straight down my throat and into my stomach while I gagged audaciously.

“Fucking, mind-blowing!” Dean said to me whilst throwing a fifty Euro note on my cum-drenched tits. “You earned that, darling. That was unforgettable!”

More True Sex Stories

I left the men to shower and get dressed whilst I headed for the girls’ showers. Walking past all of the other working girls with a fifty Euro tip and a layer of cum was beautiful.

Looking at myself in the mirror, I saw my hair was stuck to my sticky face, my makeup was ruined, and my body was covered in sweat, cum, and marks from rough sex.

My mouth tasted of spunk, stale beer from the tongues of both men and the musky scent of two cocks. I’d never been prouder.

The impromptu bukkake was an official initiation to becoming a double penetration whore. Since that winter’s day, I’ve amassed many more double penetration experiences.

With many more double penetration stories still to come. So stay tuned!

Monika Jung
After over a decade in the adult industry, there isn't much debauchery Monika hasn't seen. These days, she is a well-travelled and highly respected consultant of all things erotic. From advising sex workers to reviewing gangbang events, this busty German seductress will lead you by the hand into some of the most incredible corners of global sex.

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