Online Mistress Ch. 04: Charity

Story Info
The rocky road to charity.
4.6k words
4.46
3.4k
3
0

Part 3 of the 5 part series

Updated 10/19/2024
Created 10/14/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

The long wait for Charity

'Hello slave, you're a clever guy, so you probably figured some things out already on your own. But let me give you the full picture anyway. I'm a business woman, the owner of the Bikes & Dykes club, actually. As a person, I am pansexual and don't fit into what society calls normal relationships. Many people have that to a certain degree. Some a bit more, some a bit less. I was born with an extreme version of that.

Rather than hating it, I decided to take advantage of it, and I opened this bar twenty years ago. The bar requires membership and is for adults only. This has worked out very well, and I enjoy creating a place for people that don't really fit in. So, let's just say that your average prom queen suburban straight couple is not my demographic.

Given that it is a closed membership club, I can organize whatever I want. You've had a taste of the things I enjoy, and there is a lot more of that behind the closed doors of Bikes & Dykes. Have a look on the website, and you'll see a charity event announced for next Saturday evening. Charity events bring in good money, I donate the money to a local cause which keeps my goodwill with the neighborhood. We need to raise 20 K$.

You will participate in that event. The 'GayMasters & StraightSluts' is very popular, you'll imagine that forcing their dicks on straight guys is a major gay fantasy. I am good at turning fantasies into reality, as you noticed. The visitors pay for your sexual services by straight guys. That makes you technically a whore. Which is exactly what you want. We talked about it. It's the only way to make the role reversal really work. However, unlike a proper whore, you don't get paid, as the money goes to charity. Since prostitution is illegal, this little loophole allows me to do this, and the charity angle has tax benefits as well. Some local authorities enjoy my services as well, so we all benefit. Even you, as we saw your dick straining the chastity device several times on your ride home.

We know we've given you some surprises, and you handled them well. For Saturday, you get full transparency. Mistress Tigress will reach out to you as she coordinates the Charity events. Clean and dry your panties, you'll need them again today. If you think this is all too much and really goes too far. Too bad. You can decide not to show up, that is fine. However, your chastity cage is made out of pretty much unbreakable material. So, the decision is yours. If you make 500$ we will take if off for you. And oh, do check the website of my bar. I love new visitors. And have a look in the shoebox, slave...'

The shoebox. I forgot about that already. I pick it up from my hall and open it. Inside, there's a pair of army boots type shoes. They are pink, with a slight heel. Next to it there is a pink collar that says 'Charity Slut' in sparkly little letters. Near the clasp the strap is thicker with a small switch. If I click it, the sparkly little letters start blinking. OMFG, what have I gotten myself into. I feel my dick strain in the chastity. There are also four leather cuffs. Pink.

My computer beeps, and there is a new message. Sender says: 'Mistress Tigress -- Charity Events Coordinator.' I open it.

'Hello fucktoy, hope you enjoyed the surprises and challenges that we have put you through. We enjoyed it! This email helps you with the preparations for Saturday evening's Charity Event. Have a look on the website first, see the link below, and then read the rest of this email.'

I click the link and my browser opens a very well-designed website of the Bikes & Dykes bar. Damn, it looks slick! This is an expensive website, that is very clearly visible from the beautiful simplicity, perfect look & feel. I learned that about 500 people can visit on a busy evening, that the bar is a sanctity for everything and everybody non-vanilla and/or non-straight up to 300 miles away. There is a cheap hotel next door, which makes it easy to crash. The charity event is featured prominently.

I quickly browse through the 'who are we' section. I learn that the bar was started about 20 years ago as a hangout for female bikers. This of course attracted a certain number of lesbians, hence the name of the bar. From there it developed into a hangout for the sexually non-conformists. They make everything in house from bondage furniture to the website to photography. Mistress Stephanie is the owner/CEO of the bar and there is a team of about 20 co-owners that also have shares in the bar and form the management team. Great setup.

I browse through the management team and come across Mistress Stephanie of course. She is posing in a beautiful black cape that she has wrapped all around her, a crown on her head and as title: Chief Eccentricity Officer. I see Mistress Tigress, she poses in business attire including black-rimmed designer glasses, clipboard in one hand and small whip in the other. Chief Horny Resources Officer. And there is Mistress Panther. She poses in an outfit that is part handyman and part BDSM Mistress. She leans over the electric chair that I know all too well, holding a diamond-studded (fake, I assume) power drill. Chief Torture Officer. The others I don't know but all have goofy titles that clearly ridicule corporate function titles.

I click 'virtual tour' and a pop-up opens with beautiful photographs of the bar, a dance floor -- with poles of course -- rooms with bondage furniture, chains, racks, crosses, the works. There is a large lounging area, a studded wooden closed door that says 'meat rack', even a small church including an elaborate wooden pulpit as you may see in medieval churches. Luxurious bathrooms are included as well, with joint shower areas. The lighting of the photos, the way they have been edited, the way they blend over in each other is one of the finest things I have ever seen on a website.

There is a member login. Of course there is. I click it and find out that it is discreet about membership costs and that it is invite only. There is a beautiful photo scroll of 'different' people that look happy and cheerful in casual, classy surroundings. That must be the interior of the Bikes & Dykes bar. It is definitely not the average environment, so much is clear. I see an endless number of extravagant hairstyles, piercings, tattoos, out-of-the-ordinary outfits, from punk to gothic to bdsm to military to almost nothing.

The photos have been edited to make certain things stand out, to increase the atmosphere. All the visual aspects are extremely tasteful and creative. Designing the website is their side business, but they would give any corporate IT company a run for their money.

I click on the charity event. I have to confirm I am over 21. Then I land on a non-member preview. The screen is filled with squares in various matching tints of grey with question marks on them. The RSVP mentions: 313 people going, 863 interested. The agenda reads: 7:30 pm doors open. 8 -- 8:30 pm meat rack, 8:45 pm event starts. At the bottom: 'I'm new.'

I click on 'I'm new.' Your first time visiting the charity event? You're in for a treat, this is how it goes! You are welcome from 7:30. First 50 participants receive a 'meat rack package' containing a small paddle and three clamps with a green little bell. Until 8 pm, you are free to mingle, get acquainted and explore the space. Have a drink at the bar, have a dance on the floor, have a kiss wherever you want. At 8 sharp, the studded doors to the meat rack open, and that's what you came for! You are free to explore, grope, probe, slap the meat. That's what the meat wants. If you are one of the first 50, use the paddle. Often. And if you see something you like more than everything else, clamp it. You have 30 minutes to decide which meat you want more off, and at 8:45 they'll be installed at their stations. That's it. Enjoy! Keep moving when you inspect the meat, feel free to make multiple rounds. Think of it as our own Sixteenth chapel visit. there will be time later when they are at their stations. Please be generous with your charity donations, they play a big role in keeping this great place open and at peace with our neighbors.

The description for new comers continues. After the meatrack, the charity whores will be brought to their stations and will be available for your sexual needs at 8:45 pm. If you want to use one of the charity whores, you need to pay 100$ in cash to their pimp. We learned that the exchange of cash in front of the charity whores is a good reminder of their position. If you use less than 100$ worth of their services, there are three options. You can choose to have your money back, or you can leave the remainder with us. Up to you whether we use it for the charity event, or that it goes in the tip jar.

I open the 'meat rack' and I see 20 different 'charity whores.' I am one of them, and for each whore the station where they will offer their sexual services to contribute to the charity goal is described. Anal Station, Waxing Station, Spanking Station, Service Whores, Fucking Machine, Deep throat training, Blowjob Machines, and several more. Surprising, one of the charity whores is a real girl. I click on the pictures and she is gorgeous. That the number of the likes is through the roof is no surprise.

She'll be on the waxing station. The waxing station looks like a human-size fish grill basket where she will be tied spread eagled and can be rotated for access to every inch of her body. Candles can be bought for ten bucks. And again, the website is beautiful. My mouse pointer hoovers over the Anal Station and a picture gallery appears automatically.

I see a well-built guy in several poses. Tied up, showing off his abs, with a plug in his ass, being fucked by Mistress Stephanie, enjoying a dildo under the shower. The pictures have comments and likes. There are up to 10 maybe 15 comments, most of them very explicit. But the likes go in the hundreds! I close this and move to the Blowjob Machines.

A flashing pop-up appears that says 'First Timer!' The background of the pop-up is a nicely edited photo of. ME!? Sucking Mistress Stephanie's strapon. There are 109 likes in the bottom right corner. There are 36 'interested.' I shake and click. Many pictures appear of the sessions at the house. They are beautifully lighted, in black and white and actually very erotic. The background is me sucking the dick on the footstool in the first date. Also this picture has been edited beautifully in black and white. My hard-on is clearly visible. I am not recognizable, thank god. At the bottom left: Meat Rack Spot: FT6. Pimp: Mistress Panther. Click to send message. In my chastity, my dick tries to get hard. Again.

The pictures also have dozens of likes. 'Price List.' I see. I click. 'Blowjob and control of machine 10$/minute. Cum allowed. Condom mandatory.' 'Control of sybian: 20$ surcharge', 'nipple clamps: 10$ surcharge', 'control of ballslapper: 10$ surcharge', 'spectate to first cum swallowing with Mistresses Tigress and Panther. 10$.' Charity target: 500$. Totally confused I go back to the email. I see a button 'video.' I hover. It opens a video of three seconds of me sucking the dick on the footstool, then it says 'full video -- members only.' Viewed 158 times.

Back to the email from Mistress Tigress.

'Scan the QR code with your phone, it will give you access to your Panties Gallery. Every day you will take a sexy picture of yourself in the panties of that day and upload it. Our webteam will replace the question marks with the pictures. This generates a lot of traffic and adds to the revenue of the event. We leave the creativity to yourself, but make sure the panties are clearly readable.

For logistics, we expect you at the usual location at 7:00 PM with usual preparations. Make sure you have eaten. Wear the last pair of panties, bring the shoebox with content and your personal buttplug.

During the charity event you need to earn 500$. If you achieve that, you will suck our cocks and the chastity will come off. We need to be at the event at 7:30 pm to get you set up at the meat rack. This is a meet & greet, or better said meet & grope where the visitors can inspect the slaves before they are at their various stations. You'll be tied similarly to the inspection earlier today. There will be oversight, but our clientele is generally very well-behaved.'

'With the 2nd QR code, you get access to the contract that you need to sign in order to legally participate. We know contracts are boring, but signing a contract that you are our whore for the evening may be an exciting experience for you. Anyway, we need it before tomorrow noon.'

I scan the QR-code and the contract opens on my phone screen. Since I have a legal background, this has my special interest. After 30 minutes, I come indeed to the conclusion that they found a legal loophole that allows what can absolutely be considered as sexual slavery and prostitution to be legal for charity purposes. I sigh, sign and send it over.

I go to the bathroom, pick up the panties, and rinse them out with soap and handwarm water. I put them over the radiator to dry them quickly. And I know it's useless, but I take of my bathrobe and investigate the chastity device. It seems to be made out of space-age titanium whatever, that I probably can't even scratch.

I take my phone, scan the QR code and an app is downloaded. My info is all in there, and I get an overview of likes on my photos, interested visitors and a picture of the blowjob machine. It seems I will be seated on a sybian, and what looks like a bridle will be attached to a fucking machine so my head can be moved back and forth.

There is an 'upload photo' button which asks for access to my camera. I check the panties and they are dry. So, here goes nothing. I drop my bathrobe, put on the panties and try to take a selfie of my ass. After 20 efforts I have nothing that I like. I decide to try via the timer, and after 10 takes, I have something that I like. I hit upload. Then I go back to my computer to explore more of the Bikes and Dykes bar. When I scan the agenda, I see all kinds of parties with nonvanilla non-straight sexual themes. I go back to the Charity Event.

Several of the question marks are now gently blinking. When I hover over them, they turn into pictures of asses with panties on that read Charity Event on the back. They have been photoshopped artfully, blurry at the edges, in your face and vibrant where the attention should be. The likes and interests are also shown in real life, as I am over a yellow pair of panties for the Anal Station where the likes are increasing from 15 to 63 in about 20 seconds.

Then my phone blinks to tell me that my picture is now on the website. Another question mark comes to life and the lousy 'selfie' that I took is now a hot picture of my ass in the pink panties advertising the Charity Event. Blowjob Machine first timer is blinking as well. The likes come in very quickly and within 20 seconds I count 37. I'll have to do this daily then. Another message appears on my inbox.

'Mistress Tigress -- Charity Event Coordinator.' I open it.

'Congratulations, slave, your first panties upload was successful. Be sure to do this every day. Skipping a day earns you 30 minutes on the spanking station. This is an automated message, do not reply.'

Another message comes in, from Mistress Stephanie this time. 'Good decision, slut. I will reward you. Check the website.'

I go back to the website of the Bikes & Dykes bar and open the Charity Event. One question mark is drawing a lot of attention, as the question mark is alternating with 'Mistress Stephanie's favorite.' In my phone app, I can see that the likes and interests are increasing a lot. Oh my God what have I gotten myself into. It is 4 pm now. I had the chastity on for 3 hours, and it's driving me completely crazy. I want to jerk so bad. So bad. But I can't.

I need to pee, and go to the bathroom. Standing before the toilet I realized I needed to sit down. It's a strange experience, somehow the pee felt extra warm running through my dick, but it works.

After dinner, I checked the website again. What I mean: I spent hours on the website, checking out all the slaves, their pictures, counting their likes, studying their panties shots. My numbers of likes were good, very good even. Probably it helped that Mistress Stephanie made me a favorite. But, as I am a competitive guy, I decided to give them a run for their money.

Tomorrow's panties read 'GayMasters.' I made a plan for my panties shot... I'd do it in my bedroom. I experience a bad night of sleep, due to the chastity cage interfering with my usual night boners and masturbation cold turkey. I checked my phone for likes before I went to the toilet for my morning piss. There were a lot of new likes, interested, and the RSVP for the event was over 500. There is a waiting list now.

Sunday. After my morning piss, I setup my phone on to make the shot I want. I put on the panties that say 'GayMasters' on the backside. I put the phone in position, choose a 10 seconds timer and go down on all fours. I pull the panties down with my hands and stretch them a bit so the text is readable and ass, part of my sack and the chastity cage are clearly visible as is. As I can't support myself with my hands this way, my shoulders are down on the ground. After a few attempts, I have something where the text is readable and I am satisfied with my position. I hit upload.

Tomorrow I will top this and I already know how. After breakfast I check my phone again; 103 likes in 5 minutes. Wow. I decide to work out every day and go easy on my calories, maybe shed a few pounds before Saturday evening. I can't believe I am now fully committed to being the most popular slut on a gay charity event. But hormones don't lie.

I put on my gym attire, decide for wider trainers than usual, and drive to the gym. During the workout, I hardly noticed the chastity device. I decided to shower at home, for obvious reasons. With a cup of coffee and wearing my bathrobe I sit down at my computer to give in to my new addiction. There are many comments on my panties pictures, and the number of likes and interested are continuously increasing. The app beeps. 'Your charity goal has been updated.' I go to my profile information in my app and see the goal set at 1000$. My computer beeps; a message from Mistress Panther.

'You're too popular for your own good, slut. Since you are so eager to be the most popular slut in town I increased your target. Your jaw is going to hurt for a week. Enjoy the week, slut.'

Somehow, I manage to go through the rest of the day, a lot of time is spent on the website and the app.

Monday. After another bad night I get ready to make the next picture. "StraighSluts" say the panties. I take the buttplug modelled after my own erection, take some lube and work it into my asshole. Then I make the exact same picture as yesterday, and hit upload when I have a satisfying version. Then I go to work and don't have the most productive working day I ever had...

I realize that Mistress Stephanie is right, the perfect role reversal is almost impossible with a female dominant as they simply lack a dick. Also, my mind kept going to the panties pictures. My panties for tomorrow spell: October 11th, 7:30 pm. What picture can I make to play with that?

Then I had an idea. There's this house shop close-by, that sells household items including cheesy doormats. I went there after work and found 'Party Time' including a popping champagne bottle. Just about right. The lady behind the counter was nice, early 30's. Curly brunette, beautiful figure, cleavage despite the shop uniform, beautiful eyes, a very playful facial expression. On top of all that, she is very talkative. She looked at the item, which was totally out of line with what I was expected to buy and she didn't hide it. "Planning a party?" she asked me, very teasingly.

12