[M/FF] The Wager [Part 8] [Chastity] [BDSM] [18]

With her hands on my little penis, I quickly rose to the occasion.
Looking over at Jill, I saw that she was receiving the same treatment.
What shocked the hell out of me was the moment the butler removed his clothes.
When he dropped his boxers, Jill let out a gasp that caused me to scan downward.
Everyone has heard the expression “Hung like a horse”, well this is the horse that everyone talked about.
Even flaccid, his cock had to be ten inches long, and thick as hell.
Taking Jill’s hand, he placed it upon his cock.
Jill looked almost afraid to touch this monster, yet as the seconds ticked by, she began stroking his cock.
As it rose to the occasion, Jill’s face underwent a transformation, from fear, and uncertainty, to joy, and anticipation.

Once this monster had reached it’s full potential, Jill dropped to her knees.
While the minutes ticked by, Jill began inspecting her prize, lifting his balls, to feel their weight, and heft.
When her attention focused on the cock in front of her, Jill ran her tongue along the crown, causing it to twitch in response.
Looking back towards me, Jill smiled, and winked.
Turning back, Jill opened her mouth, and took the tip between her lips.
Try as she might, Jill could get no more than the first couple on inches in her mouth.

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Categorized as Erotica Tagged

[M/F] The Wager [Part 7] [BDSM] [Chastity] [18]

When she was on the verge of her next climax, I pulled away, and moved forward to line my penis up with the gates of heaven.
What followed wasn’t making love, it was nothing more than raw unbridled fucking.
To those around us, what they heard was the wet squishing sound of our bodied covered in sweat, as our hips slapped against each other, along with the sound of my penis slipping through Jill’s soaking wet pussy.

“Jill, I’m cumming, cum with me, cum with me NOW!” I yelled.
Jill climaxed first, followed by my orgasm seconds later.
Stabbing my penis deeper into her body as my balls emptied themselves deep into Jill’s body.

Falling away from Jill, I rolled onto my back, it was then that Jill leaned over my worn out body, and began kissing me with an ardor, I wouldn’t believe possible.
Returning the kiss, I decided that I was falling in love.
As we lay there Mistress came forward, and took the two of us in hand.
Leading us to a side room, we were told to crawl into the bed, and rest for a bit, that she would return to collect us in about an hour.

[M/F] The Wager [Part 6] [Chastity] [BDSM]

“Thomas, please undress so we may conclude the fitting.”
Standing naked in my living room with Miss Lisa fussing about in the bag, along with a couple of other bags she had brought, one of which had a beautiful pair of dress shoes.
Unzipping the garment bag, Miss Lisa first removed a pair of basic white boxers.
Placing my hand on her shoulder for support, she knelt down and slid first my right leg followed by the
left into my new boxers.
Next came the starched white shirt, followed by the pants.
Shirt buttoned up, pants pulled up, she produced a pair of suspenders from the bag, and adjusted them to fit properly.
Strapping on the cummerbund, she reminded me that the proper way to wear this was with the pleats in the up position.
As a reminder she told me they were nicknamed “Crumb catchers” in order that you can remember it’s correct way to wear them.

Stepping over to the full length mirror attached to the back of the door, I was stunned at the transformation.
Hello, my name is “Bond James Bond”.
Fuck, I looked good, dressed in this classic English style tuxedo, I looked like a gentleman of royal decent.

[M/F] The Wager [Part 5] [Chastity] [BDSM] [18]

When I returned to the living room, Mistress had me stand in front of her.
Taking my body in her hands, she pulled my balls through the ring of my chastity cage, followed by sliding the cage onto my penis, and locking it in place.

“OK little man, I have a task for you.
Tomorrow at eleven am, you are to got to this address, and ask for Mr Green.
We are going to a party on Saturday evening, and you are going to be fitted for a proper tuxedo.
You are not to worry about the cost, it is all paid for.
Do not be late, Mr Green will report back to me on how the fitting went, along with your demeanor.
I want you to understand, your behavior is a reflection on me, do not disappoint me.
Now you need to get dressed, and head home, I will call you tomorrow afternoon, with details for the party.”

The next morning I stood in front of the shop I was asked to visit.
It was a nondescript shop front, the only indication of what type of business was conducted inside was a sign that read “Costumier”, below that a smaller sign read “Seville Rd England”.
Upon entering, a small brass bell above the door tinkled as the door hit it as I opened the door.

[M/F] The Wager [Part 3] [BDSM] [Chastity] [18]

“My boy, maybe I should have been clearer in my intentions.
You are to wear this cage until I decide to remove it.
Now since you are new to all of this, I will see you tomorrow at three pm.
So be here tomorrow, and we will talk about what is going to be expected of you from here on out, is that understood?
Now get dressed, and ready for the rest of your day.”

Once dressed, I was ushered out of the penthouse, and into the elevator.
As the door closed, Mistress blew me a kiss, and a wink.
Standing in the elevator, everything that had happened in the last few hours, began running through my tiny brain.
First off, I accepted an invitation from a beautiful woman to join her at her place.
When I saw her play room, I blindly went along with what was going to happen to me.
OK, the fact that I am a horny boy, and if you told me the only way I was going to get laid that night was to wear a pair of pork chop panties, while trying to sandpaper a grizzly bears ass, I would have done it.

[M/F] The wager [Femdom] [Part 2] [18]

Halting the paddling for a moment, she began to lube up the little hole in my bottom.
The next thing I knew was her inserting something like a plug into my bottom.
What really blew my mind was when the plug began expanding inside my bottom.
With each pump the plug expanded more, and more, until I had felt fuller than I had ever felt before.
When my body began to cramp up, I used my safe-word, “Yellow” to tell her I couldn’t take any more of the plugs inflation., at which point she halted what she was doing.

“Tom, how are you doing?
I hope you are willing to continue our little drama, I have so many ideas percolating through my head right now, that it would be quite the shame to waste them.
If you are ready to continue, please let me know.”
I gave Mistress the go ahead, and that I had recovered from the intense feeling of having my bottom inflated with the butt plug.

[MF] The wager [BDSM] [18]

Hello, my name is Tom.
Lets start by me telling the world that I’m an idiot.
There it is, my big admission.

One reason for this self declaration is the bet I made with my best friend.
The bet was, could I meet a girl whom I could seduce, and convince to becoming my submissive, in one week or less.
The prize was nothing more than bragging rights.
We had a habit of making stupid wagers all the time.
Everything from when a pigeon would fly away, to how long it would take for a long freight train to pass the crossing we were stuck at.

Anyways, the first few nights after we set the wager, we began scoping out various hangouts, while I began flirting with girls that struck my fancy.
So far, I have gotten my face slapped a total of three times by three different girls, given five phone numbers that turned out to be fake, along with a lot of disgusted looks from others, and one enraged boyfriend who showed up out of nowhere, allowing me to discover just how fast my feet could take me in the other direction.

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Categorized as Erotica Tagged

[M/MF] The joys of delivering pizza [Part 4] [18]

It’s another Friday night, and the deliveries have been flying out the door at record speed.
At this rate, I’ll need to refill my gas tank a second time in two days.

The time is eleven forty, and I had only two more deliveries left on my run.
The second to last was to a nice older lady, who tipped me ten dollars for her food.
The next one was only three blocks away, and in a gated community.
Driving up to the closed gate, the guard called ahead to alert the home owners that I was on my way.
The house wasn’t large, in fact it was rather modest in size.

Ringing the doorbell, the man who opened the door was a rather handsome man somewhere in his forties, if I had to guess.
While I stood in the front room waiting for him to count out the cash, I kept hearing moaning from the room around the corner.
As he stood there he told whoever was in the other room that she was making far to much noise.
His rejoinder didn’t seem to have any effect on the other person.
In fact the sound level increased three fold.

The joys of delivering pizza [Part 3] [18]

After last weeks frat party, the last few days had been uneventful.
I had a couple of come-ons from people that I didn’t feel were going to go anywhere.
That however didn’t stop me from keeping my eyes open.

Being a Wed, there weren’t many orders going out.
This evening I had only one delivery stop to make.
When I arrived at the house, I was amazed at the sheer size of the estate, and estate it was.
This was the high end area of town, where people like me would never be able to afford a home like this.

Pulling into the huge circular driveway, I gathered my hot bag, and walked up to the door.
I discovered that there was no doorbell to be found, rather affixed to the door, was a massive brass door knocker in the shape of a giant hand.
Pulling back on the knocker, I let it drop, the resounding thud echoed throughout the house.
Somewhere from above a speaker asked me to wait a few moments.
Before I could wonder where the speaker was hidden, I could hear the door being unbolted.

The joys of delivering pizza [Part 2] [18]

So far, it’s been five days, and my delivery route has been uneventful since I was gifted a world class Bj, by that beautiful red headed lady.
Today is Friday, and the orders are coming in fast, and furious.
In my first hour, I had delivered five pizzas, and garnered fifty dollars in tips.
While there had been a couple of girls that hinted at a future dalliance, nothing special had happened.

By the time my last delivery was rolling around, I was ready to call it a night.
My final stop was a frat house near the local university.
For this drop off, I had six pizzas to deliver.
Approaching the front door, I could hear one hell of a party going on inside.
There wasn’t any need to ring the bell, because every few seconds the door flung open, and one or more drunken frat boys, or equally drunk girls would wander in, while some staggered out to crawl back to their dorm.