Our Trip to Italy

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

As my pain increases, and I am approaching the maximum pain that I think I can take, she will decrease the amount of torture slightly for a short time, as she carefully watches my reactions, waits for me to relax a bit, and then she will increase the torture again, and again, until I am ready to break and pass out.

The worst pain is my ball sack that feels like it is going to rip and drop my testicles out onto the floor, and thankfully after what feels like hours of torture this is the first to get released.

After she releases my balls, I look down and my balls are hanging low and are bright red.

The mistress then leaves me there for a few minutes and returns with a very cute petite Hispanic looking girl with very large natural tits and a nice round ass. Her hands are bound and she is blindfolded.

The mistress is slapping her with the crop and guiding her down to her knees in front of me. She grabs her head as she is slapping her ass with the crop and pushes her face to my limp cock and commands her to suck. And she replies with a;

"Yes mistress"

As she reaches up and takes my soft penis into her mouth, I look down to see that her nipples are red and swollen and her body looks abused, probably from the same types of torture I have been enduring myself.

With her warm mouth around my cock, it doesn't take long for me to get hard. She is up on her knees with her hands tied behind her back and while she is sucking me, I see the mistress is now adding more rope and binding her brown plump tits tight, making her chocolate areola's bulge as she is pulling the rope back even tighter.

Then she ties her elbows, pulling them together and then tying her down to the hooks on the stone floor, keeping her from getting any forward movement on my cock.

As I try to thrust forward the hooks in my ass pull me back stretching me even wider and causing discomfort and frustration.

The girl in front of me is trying her best to get as much of me into her mouth as she can, but her restraints are preventing her from getting any more than half of me in her mouth, but she is still pleasuring me nicely.

Just about the time I think that I am going to cum, the mistress pulls her back and slaps me on the head of my dick with the crop, and she does this over, and over, for probably an hour until the man in black, the one that took my wife away, enters the room.

I hear him say;

"I am ready to take her back to join is wife"

"How is his training coming along?

The mistress reply's;

"He's doing fine, just a little more and he will be ready.

He looks down at her, he reaches down and unhooks her from the floor, he pulls her by the arm and says to her;

"Are you ready to rejoin your companion?"

"Yes master"

"Have you been a good girl and done everything your mistress has told you to do?"

"Yes master"

The mistress starts by taking off my nipple clamps and lowering my arms, as the blood rushes back into my arms it feels like a thousand needles are pricking all over. She then unhooks my lower anal hook from the floor, but then, before she removes the hook pulling me upwards, she adds more tension to keep me gaped wide open.

Now she takes the thick lube that is like lard, and then she starts packing my ass, you know, like you would pack cheese into a pasta shell.

Then she releases the tension on the upper hook, and then she pops it out. That golf ball sized ball, pops out with ease.

She then pulls my arms back up and starts rubbing my whole body with oil, making my body slick all over.

She reaches around and starts rubbing my cock and balls until I am fully erect. She takes the nipple clamps and pinches my nipples again and tightens them until I start to moan in pain.

I get a good lashing with a whip and she demands;

"No more complaining or I will make you suffer."

After some time of her whipping me, and tormenting me, she lets my hands down, drags me over to the other end of the dungeon, where she has a very tall, dark skinned black woman, bent over the restraint table waiting for me.

I can see that her body and legs are all oiled up, they are glistening, she is the very darkest of black, she looks so hot, and she is looking very sexy to me all tied down.

This woman is wearing black, spiked high heels, and she has some very long, beautiful shapely legs.

Our mistress has her here, and she has left her tied down for who knows how long, she is face down with her ass up and ready, with her legs spread wide with a 4X4 leg spreader.

I can see that she has some very large breast, they are squeezing out as the are pressed tightly to the table, and she has a very pretty face, with very fine features.

Her face is turned to the side, pressed to the table, each of her wrist are bound, one at each corner.

The mistress walks me over behind her and releasing my hands tells me to step up on the leg spreader and tells me to start massaging this woman's back.

"Yes Mistress"

I start rubbing her back and the mistress starts rubbing my cock to get me nice and hard and then tells me to fuck as she takes me in her hand and guides me into her asshole.

As I am really starting to pump her good the mistress goes over to the wall and pulls down the biggest strap on dildo, the oh my god that's fucking big dildo and starts walking back to me with a step stool in tow.

She comes in behind me and steps up on the stool, she pushes my ass in, she is forcing my cock to move deep inside this sweet tight ass, and she just holds me there. With my cock buried deep, she lubes up the dildo and starts working it into my asshole, just a little at a time, but just the head.

She just pushes the head in about three quarters of the way, but that head is huge, and it is now hurting me a bit, so I clinch my cheeks together to keep her out.

The girl I'm fucking is getting restless; she is trying to wriggle me in deeper and starts squirming.

Meanwhile I am just hoping the mistress will back away, I don't want to get fucked in the ass.

The mistress whips me with a crop and demands that I relax, she tells me;

"Relax your ass! Let, me, in!"

As she pushes harder and keeps whipping me with the crop on my lower back.

"Yes mistress"

I take a couple of deep breaths and release my muscles only to have her shove it in me hard, making me scream in surprise. Now she has that huge head in and it has made it through my sphincter, but even with heavy pressure it won't go any further. She then pulls out and immediately pushes it back in, and now she is going in further each time.

The thick lube inside my rectum is paying off and she is getting in with more ease. This dildo is about as big around as a bottle of water and about ten inches long.

She keeps pumping me until I can feel her hitting my prostate, I can feel my cock draining deep inside this nice tight ass I am buried in.

The mistress grabs my hips, stands in place and starts pulling me back into her, back and forth so I'm fucking and getting fucked at the same time.

The harder I pump the girl on the table, the harder the mistress fucks my ass. I can feel the cum flowing through my cock throwing me into a state of constant orgasm.

After about fifteen minutes of this the mistress pulls out and pulls me back out of the woman on the table. She unties this girl from the table and orders her to stand up, she then tells me to take her place on the table.

When I switch places with her, I then realize that the woman I have been drilling has a cock the size of the strap on, this she-male is huge, she has been hiding her massive cock, it has been tucked up underneath her the whole time, it has been between the table and her and I was at a high angle looking down, so I couldn't tell. I just knew that her ass was clean shaved like mine and tight.

The mistress quickly gets me locked down and the girl says;

"Okay baby, it's my turn."

Then she comes around quickly, and slides her massive meat deep into me, and then starts pounding me hard and with this real cock, it's slides in really easy, she slides in and out so easy, pounding me so hard, but it is so smooth compared to the dildo, I am so surprised, this being my first time ever getting fucked in the ass. Wow!

I didn't know what to expect, but it feels good, and it would seem that I have gotten into a continuous orgasm, which is something I've always heard of, but never thought I would experience. How is this even possible?

I can feel my cock leaking, my body is quivering, I feel myself dripping more and more with cum, and this black beauty dumps her load in me deep, she pulls out and the mistress says;

"Your training is now complete; you are now ready."

"Yes mistress!"

"Ready for what?

I then hear footsteps entering the dungeon, a great many footsteps, like a crowd of people.

I raise my head up as much as I can and I see about fifty men coming over, the crowd is mixed with men and she-males and they all have extraordinarily large rock-hard penis's

Then I feel a pair of warm hands on my hips, a then a huge, warm, firm, and fat cock pushes in to me, and slowly starts fucking me deeper and deeper.

The restraints on my hands are given some slack, someone steps up and grabs my hand and puts their cock in it, and the same on the other side.

The voice of the mistress says;

"You need to jack them off!"

"Get those hands moving!"

She cracks the whip and I get a lashing on the small of my back and then on my hands.

She demands;

"Start jacking!"

I have my eyes closed but I start to work both of my hands and both cocks are huge and they are both dripping pre-cum down my wrist.

I get a slap on the face with another large cock, and then I feel the soft firm head of a big cock, dripping pre-cum on my lips.

Then I get another crack of the whip as the mistress demands for me to suck.

Meanwhile the man in my ass is pounding me hard, I keep getting the feeling of myself dripping cum every time he tags my prostate, and he does keep finding my P-spot over and over again.

Then I can feel someone getting underneath me, and as he starts to blow me; Now all of the sudden, the cock in my ass stiffens, and then I can feel wads of cum shooting deep inside me.

Again, I can barely process what's happening to me, it's so much!

After he finishes unloading into me, he pulls out to make way for an even bigger cock, this guy that takes his place starts pushing even deeper somehow, he goes deeper and deeper, until I can feel his pelvis slapping my cheeks and thighs.

The guy in my mouth starts blowing his load in my mouth, he is deep throating me so his cum is shooting into my sinus's and down my throat.

I cough him out a little, and then I gag before he pulls all the way out; Then two thick streams of cum, come shooting out my nostrils with force, and it starts running into my mouth and over my lips.

One of the she-males comes over and licks it off my lips before she pushes her cock deep down my throat, barely allowing me to catch my breath.

The mistress gives me another lashing;

"Keep those hands moving!"

After everyone has a turn on me, and now I have at least twenty loads in my ass, and the same or more in my stomach, the group pulls me off the table and moves me to another restraint apparatus.

The new spot is an all wood and leather bench, where laying in wait for me, is a she-male, with nice tits, laying on his-her back, the other guys lift me up and put me on this nice big cock, cowboy style, and then they push me down chest to chest and I feel another cock pushing in for a double penetration into my stretched sloppy asshole.

My ass is so stretched they both slide in with ease, and then more men are coming into the dungeon to join my gang bang.

The cocks just keep coming, and they keep Cumming and Cumming inside me and down my throat.

After hours, and hours, and who knows how many loads, I didn't even try to count, they take me down and put me on my knees for one last blow-bang, and a bukkake session and this gang bang is finally over.

The mistress tells me;

"Your desires have been for you and your friends to do this to a woman and we wanted you to experience just how it feels to be the center of attention and the receiver."

"How do you feel?"

"I feel used and abused, I came in ways I never knew were possible. I was in constant orgasm for hours and hours, and it was incredible! My mind was blown and so was everything else.

"This is something I didn't know I desired, but I did most definitely enjoy my day."

Then she says;

"It wasn't a day. You have been here for the last three days."

"I will take you to the river shower, the the waters of Styx will revive your body, and there you can rest.

After I wake up still laying under the raining waters, my body feels as if I wasn't practically fucked to death, and now I feel great, but I am missing my wife and the previous constant orgasms.

I say to myself;

"I wonder where my wife is and how her thing played out."

I call out;

"Lilith"

I turn around and I see her magically appear, she has her wings open but they don't look angelic, they look more demonic, they are bright red and black, and they curve around like a bat with sharp points at the tips, but they are still so very beautiful, and then they just disappear under her shoulders like they were never there.

She answers;

"Yes, my dear."

"Can you please take me to my wife"

She says;

"I would love to, we can go look in on her right now, you just need to follow me."

We exit the chamber and start walking down another long corridor in the cave tunnel system.

She directs me to a narrow opening in the cave wall, she then pulls a key from around her neck and unlocks a door

When we enter, we end up on a tightly wound, downward spiraling foot path.

As we descend, I can feel the heat rising again, but this time it's almost unbearable, like we are heading into a furnace.

I ask Lilith;

"Where are we going?

And she replies;

"To your wife of course, she is with my master in the final level, but don't fret, we will be there soon."

As we approach the last few steps it is so hot my whole body is dripping with sweat, and I can see a red glow and the smell of sulfur in the air.

We head towards the red glow and I can see what looks like hundreds of people intertwined together in a massive orgy.

The red glow is coming from a lava river that is separating us from the crowd.

Lilith puts her arms around me, she spreads her wings, picks me up and we fly over the river.

When we land on the other side, I can see my wife being suckled by some beautiful women, there is one on each of her breast.

She is having sex with a massive hulk of a man, he has muscles coming out of muscles, and he is underneath her, he appears to be fucking her in the ass.

I walk up to get a closer look and I can see that this man has two penises and is actually fucking both of her holes at the same time. I am shocked and when I come around to make eye contact with her, I can also see the face of the man. It's the same face of the devil pictured on her tattoo.

She looks up and sees me and says;

"I have been waiting for you;

"I want you to join us"

She spins around without getting up, she leans back on his chest and raises her legs and says;

"Please take my pussy" "I want you inside me"

Before I move in, Lilith holds my arm back and says:

"You have passed all of our test, and you are worthy, you can stay here forever, or you can choose to leave."

"If you choose to leave you may never find your way back here again, but you must choose together."

I nod in understanding and step up to the alter, I look at my wife, and then strait in the eyes, I give her a big wet kiss, and tell her that I have missed her.

Then I just put my big fat cock in her pussy and start to fuck the shit out of her.

Next, I can feel his second penis entering my asshole, and his long snake tongue is licking my balls.

He pushes his cock in so fucking deep that he goes all the way to my P-spot, and that pushes me to immediately cum deep inside of her, and then everything fades to black.

When I wake up the sun is shining, I look around and we are in our hotel, the air conditioner must be off because it is very hot in the room.

I get up and go take a piss and turn on the air conditioner, and when I am coming back to bed, my wife rolls over and says;

"What time is it?

"6:00 AM"

I start to tell her that I had this very wild and vivid dream, oh my god! it seemed so real.

She says with a smile and a little laugh;

"Hold that thought, it's my turn to pee now!

She jumps up, and then I slap her ass, she laughs and then I see her devil tattoo.

"Shit!

My mind is blown; this has been the best vacation ever.

The End

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 1 year ago

This is a very exciting sexual madness!

Share this Story

Similar Stories

Bill and Stacy A young couple’s awakening amidst vacation confusion.in Group Sex
Joni & Mitchell's Swinging Adventure Joni & Mitchell have a swinging adventure.in Erotic Couplings
Anna Succumbs to Neighbor's Cock With encouragement of husband, wife becomes more daring.in Loving Wives
Bad Neighbours Pt. 01 New neighbours change upset Abbie and Andy's marriage.in Loving Wives
The Dirty Old Neighbour Dirty old man wants his neighbours.in Exhibitionist & Voyeur
More Stories