[assistantann] 🙅‍♀️ Jobs

[OldGreyGeek]

[assistantann] Extreme Fantasies 17

“Yes, she looks stunning but let’s get her raised up so we can really enjoy seeing her dance.” One of the bigger men said. The men each took hold of the cross and began to raise me up. Slowly, inch by agonizing inch I left the ground

“Don’t drop me guys,” I tried to joke, but really couldn't due to my increasing discomfort.

I felt my weight transfer from laying on the ground to my arms and the nails in my hands shot waves of pain as my body started to hang from them. I felt my bare back slide down on the splintery wood. I let out a groan as I realized how much discomfort I was about to experience for their entertainment and started to second guess my decision.

“Ok lift a little higher,” one of the men ordered, “almost there”. Up higher I went my body fully displayed as they placed the bottom of the cross into a hole that had been reinforced by cement just for this purpose.

“She looks absolutely wonderful,” one of the men commented as he looked up at my helpless body.

 

[tanuno]

Ohhhhh!!!!!!!!
I fell asleep!
You found the continuation!

 

[OldGreyGeek]

Ohhhhh!!!!!!!!
I fell asleep!
You found the continuation!

Yeah, this AnntheAssistant/AssistantAnn is weird and I like it.
Not so enamored with the AI. Don't know why it chose railroad spikes.

 

[OldGreyGeek]

[assistantann] Extreme Fantasies 18

I saw the men step back to, their eyes running up and down my body, to admire their handiwork, my body stretched and exposed for their enjoyment

My shoulders were starting to feel the strain as every muscle twitched under the constant pull of my own weight with a deep throbbing ache.

I soon realized that breathing wasn’t easy either while being displayed like this. I started to hope that they would just take a few pictures then let me down. One of the men stepped forward and in a low gruff voice asked, “Are you comfortable up there crux slut.”

I spat out “No I am in pain, are you planning to let me down soon?”

My hopes were dashed when he answered, “Of course not we plan to leave you up there at least all night.”

I looked over at Mark; he just shook his head, obviously planning to hold me to what I said in the car

 

[OldGreyGeek]

[assistantann] Ann Tries Modeling 7
“I know how to get her to struggle,” Mark said, “Rob, let me get a shot of you pulling the lever,”

“Really, I ah don’t know if I want to be in the picture,” Rob hesitated.

“Don’t worry I can just get your arms in the shot if you prefer,” Mark said. Rob walked over, reached out and pulled the lever. The saw roared to life, the blade moving faster and faster.

 

[OldGreyGeek]

[assistantann] Ann Tries Modeling 8
Ann screamed, “You said this thing didn’t work, what the hell is this!” She pulled on the ropes trying to get free.

“Oh yes, perfect, keep struggling just like that,” Mark coached as he took more pictures. “As lovely as Ann looks, my customers will want to see a bit more of her. Rob, take these scissors and cut her bra off. Don’t worry she signed the waiver for nudity.”

 

[OldGreyGeek]

[assistantann] Ann Tries Modeling 9
“No wait, turn the saw off please, I’ll do topless if you turn the saw off!” Ann protested, A couple of snips of the scissors and Ann’s breasts were exposed. Mark and Rob seemed to enjoy how they jiggled as Ann struggled with the ropes. “Ok you have your pictures, let me go you bastard!” Ann continued to complain.

 

[OldGreyGeek]

[assistantann] Ann Tries Modeling 10
Mark approached the bound up Ann with the scissors in his hand. Two snips and her thong was removed revealing her freshly shaved pussy. “You aaahh!” was as far as she got before the thong was stuffed into her mouth. “Mmmpphhhhhppph!” the protest continued.

 

[OldGreyGeek]

[assistantann] Ann Tries Modeling 11 & 12 (same text on both images)
Ann struggled and tried to get free of the ropes but they had been tied tight. “Good, Ann, keep struggling, that is what they like to see,” Mark coached as the saw cut through the log up between Ann’s knees. Rob’s eyes were fixed on Ann’s struggling body clad only in the thigh high stockings and garter belt.

 

[OldGreyGeek]

[assistantann] Ann Tries Modeling 13
The blade cutting the log between Ann’s thighs now and getting very close to her helpless body. Ann could feel the blade closer and closer to her exposed pussy. She tried to brace for the pain she knew was coming. The blade nearly touching her, it’s teeth about to bite into her flesh. She sucked in a deep breath and braced herself.

 

[OldGreyGeek]

[assistantann] Ann Tries Modeling 14
Then it went quiet.

“That was a great shot!” Mark said as the saw stopped. “You were great Ann that looked very real,” Mark said as he pulled Ann’s wet panties out of her mouth.

“You asshole! I thought you were going to cut me in half for real!” Ann yelled as they cut her free from the ropes and helped her off the log.

“That is what made the series so great,” Mark said, “If you are interested in making a lot more money I am sure my fans would love to see more of you,”

 

[OldGreyGeek]

[assistantann] Extreme Fantasies 19

My heart pounded as one of the men drew a long shiny blade into my view. The light caught the blade just right and a shot of fear raced through me. I prayed he wasn't going to use the sharp blade to stab me, then his voice cut the tension..."she is pretty up there, but way overdressed"

“What do you mean overdressed?” I managed to say between breaths, “I am barely covered by a tiny G-string.”

“I know,” he smiled, “you are wearing too much.” He smiled slyly as. I was paralyzed as he moved closer holding the blade deliberately for me to see. He slid the cold steel against the soft skin of my inner thigh. I felt the blade slide up my hip under the string of my G-string. With a quick flick of the wrist and the thin piece of fabric shredded.

He traced the blade across my stomach to my other hip and held it there just long enough to send shivers through my entire body. Then with another quick flip that string was gone too. The tiny triangle that was the only covering I had over my shaved and already wet pussy gave way, leaving me fully exposed.

A few quick tugs on the strips of cloth and the scraps of fabric pulled away from my most sensitive area. His eyes got dark as he held them up for everyone saying "her panties are soaked" as he held them up to his nose taking a deep sniff then placing them in his pocket.

I blushed at having my excitement from my predicament made known to them.

 

[tanuno]

[assistantann] Extreme Fantasies 20

My naked body was completely on display with my hands and feet painfully nailed in place I was unable to cover myself in any way. I could feel the cool air on my bare skin making my nipple hard as I hung from the cross. My legs were feeling tired and hurt from pushing myself up so I could breathe easier.

The men were watching me as I moved up and down to breathe and try to ease the discomfort of my predicament. I felt their stares like hot hands sliding over me. Faces tight with lust and something darker, something that drank in my struggling. One of them laughed low and mean...."look at her, she's really starting to suffer now.". Those words sank into me like another nail. I was both excited and scared me knowing I was the subject of their pleasure and enjoyment. I didn’t know how long they were going to leave me up there or even if they were going to let me down at all.

After a while they brought out a barbeque grill and started cooking steaks. I could smell the meat cooking and realized I was getting hungry as well.

 

[tanuno]

[assistantann] Extreme Fantasies 21

The light was beginning to fade as the men sat down to eat their steak and grilled vegetables. The aroma hung heavy in the air; my empty stomach twisted with hunger, yet no one offered me even a single bite.

Every muscle in my body throbbed with exhaustion. I tried to shift my weight—first forward, then backward—desperately seeking a position that might ease the relentless pain. The nails barely allowed me to move an inch; with every shift, agony shot through my hands and feet. I was trapped.

Then, I noticed something that made my blood run cold. The men weren’t just eating—they were watching me. Their eyes tracked my slightest movement, and their conversation was occasionally punctuated by hushed laughter. Whenever I shifted, driven by the pain from the nails, someone would pause with a fork halfway to his mouth, watching me as if waiting for something to happen. A sharp pang of pain forced a soft moan from my lips, triggering an unexpected reaction.

“The bitch is really dancing for us now,” one of them said with sadistic glee.

“This is way better than the stripper we hired last year!” another exclaimed. “And that bitch was hot.”

“She’s not even half as pretty or sexy as this ‘snuff-film’ bitch we’ve got this year. Look at the way she moves. This beats any pole dancer,” another added.

I felt humiliated and used. I was in excruciating pain, and these men were reveling in it. At the same time, I couldn’t help but feel a flicker of sexual arousal, knowing that they were deriving pleasure from my body.

 

[tanuno]

[assistantann] Poker Loss 1 + VIDEO
He got home late from poker night with some new friends, I asked him "How did you do honey?"

He said, "I lost big".

I asked, "How much did you loose?" hoping it wasn't a huge amount.

He said, "They really don't play for money but for some kind of forfit. Oh and we to have to host the monthly barbeque next weekend." That didn't bother me I love barbeques.

The afternoon of the barbeque he found me getting ready in the bedroom. He told me the the forfit involved a slutty outfit that the guys picked out. I was amused and asked "so what do you have to wear today"

He said that the outfit wasn't for him but was for me.

I gasped when I saw how skimpy the little swimsuit was that they expected me to wear. the little black one peice with shiny rinestones didn't have much material and even less in the back.

"Why do I have to go to the barbeque in this slutty outfit when you are the one that lost?" I protested.

He explained, "That is what the rules are"

​

 

[tanuno]

[assistantann] Poker Loss 2 + VIDEO (02 videos)
I reluctantly put the flimsy swimsuit on the bed then pulled my top off and slid my shorts down my legs. I saw him watching my naked body and began to wonder if he didn't throw the game just to see me wearing something so slutty outside. I picked up the swimsuit and steped into it pulling it up onto my body, It fit perfectly but didn't cover much.

"My tits will fall out of this, and it doesn't cover my ass," I protested.

 

[tanuno]

[assistantann] Poker Loss 3 + VIDEO

"You look great!" he say with wide eyes, "Shall we go make an appearance?"

I tried to give him a smile feeling very naked. "I am sure I will be making more of an appearance than you will be," I said as I walked out of the room. "But sure lets do this"

​

 

[tanuno]

[assistantann] Poker Loss 4 + VIDEO

As I walked into the living room I was surprised at the scene out the patio door. Several people had gathered for a party, but the shocking part was the cross that was set up in the middle of the yard. I know I looked worried when I said, "I suppose that cross is part of the bet as well isn't it"

he said, "Yes, I'm sorry it is"

I just sighed and said, "And it looks like everyone is here"

​

 

[tanuno]

[assistantann] Poker Loss 5 + VIDEO (02 videos)

"Are you ready?" he asked me.

"No, but I they are waiting" I nervously replied

He opened the patio door and anounced "Here she is," with what seemed to me with too much excitment.

He held my hand as we walked towards the cross. "I can't believe that you are going to tie me to that cross in front of everyone." I said

"We aren't going to tie you to the cross" he said

I felt a moment of releif and let out a "Whew"

What he said next shocked me, "We are going to nail you to it"

My heart skipped a beat and "Oh fuck" was all I could manage to say

 

[tanuno]

[assistantann] Poker Loss 6 + VIDEO (02 videos)

My legs felt wobbly from fear and nerves when two men lifted me up and placed my back against the wood of the cross. Every eye was on my nearly naked body. Someone produced a hammer and some nails, "Oh Shit," I thought out loud when I saw them. the first nail was placed against the palm of my left hand then the hammer drove it through my flesh and into the wood, the searing pain made me scream, which the party goes seemed to enjoy. then my other hand was nailed into place. The nails driven through my feet hurt the worse yet. The men were enjoying their work.