Executive Assistant Ch 04 Cam Show

Ashleigh was back in her college dorm and took a long shower. She was able to clean herself up but no amount of showering could get rid of the shame. Try as she might, she couldn't stop replaying in her head how she was forced to make out with her sister along with the other perverted actions. (God, why did this happen? I wish I could just wake up and leave this nightmare behind me. At least Mia and I didn't fuck each other. So it's not really incest, right? Just making out and kissing her breasts. Argh, am I really trying to find a silver lining in this? So stupid, damn it all.)

Ashleigh didn't get any sleep that night and the next day went by excruciatingly slow for her. She kept waiting for Mia to call even though it was a conversation she did not want to have. Around noon, Ashleigh mustered up enough courage to call her sister instead.

Ash: "Hey, Mia, how are you doing?"

Mia: "Sorry, Ash. I don't think I can talk much today. I have a terrible hangover."

Ash: "I feel awful, too. But I think we really need to talk about this."

Mia: "Here we go again. Are you going to scold me for partying and having fun?"

Ash: "I wouldn't call what happened yesterday 'fun'."

Mia: "How would you know what happened? Don't tell me you were spying on me."

Ash: "Uhm... wait. What exactly happened yesterday?"

Mia: "Fine, I'll tell you. I was having fun with my friends at a party and we got wasted, though it was earlier than usual. Then, some guys showed up and took me with them. I think we went to a frat party; there were mostly guys there. I don't know, I don't remember much after that. I noticed some cum stains this morning, so I must have fucked someone there."

Ash: "That's all you remember?"

Mia: "Yes, now will you please leave me alone? I need to go throw up again."

Ash: "Sure, take care of yourself, Mia."

Ashleigh felt a huge sense of relief. She knew she would still live with the guilt for the rest of her life. But at least her sister didn't have to deal with the trauma thanks to her blissful ignorance. Ashleigh was also furious at Tim for putting her in that situation but now she just wanted to move on and not deal with the event any more.

Life went mostly back to normal for Ashleigh with school and work. Thankfully, there were no more "business conferences". The main change was that she also had to pleasure a businesswoman on occasion after her encounter with Lauren opened that avenue for Tim. Summer eventually came and Ashleigh had completed her first year of college. She took one course during the summer semester so she had something to focus on besides work. While working with Tim in the office one day, he brought up a new business opportunity.

Tim: "So, I've been thinking. You're in high demand with my clients but they don't always have opportunity to meet with you. Now that it's summer, many of them are also on vacations with their families."

Ash: "Uhm... where are you going with this?"

Tim: "Good question. I have set up a private streaming server. We'll schedule a special live broadcast where you can play with yourself and have clients from around the world enjoy the show."

Ash: "Are you serious? This is too fucked up even by your standards."

Tim: "I thought you would be more appreciative. It means you don't have to physically interact with anyone while still letting them get off."

Ash: "Yeah, but it's the internet. Anyone could end up seeing me."

Tim: "Like I said, it's a private server. Only approved clients will get access to the show."

Ash: "Still, they could record it and then share or upload somewhere else."

Tim: "No, don't worry. It's a one-time live broadcast event. There is no option to download or record on this platform."

Ash: "I don't know. It's the internet, nothing is ever safe there. This is asking too much, I can't do it."

Tim: "I have already invested too much money and time into this. It needs to happen, Ashleigh."

Ash: "Well, you should've thought of that before."

Tim: "You're going to do this. Or would you rather I get Mia to do it instead?"

Ash: "What?! No, you can't. She wouldn't!"

Tim: "A little alcohol and encouragement can go a long way, especially with your sister."

Ash: "No, please. You can't do that to her."

Tim: "Okay, then I think we have a deal. I will send you the details once everything is ready and expect you to put on a good show for the clients. Oh and be sure to follow whatever requests they ask of you."

The following week, a package arrived for Ashleigh at her dorm room. Fortunately, she had the room to herself for the summer. The package contained a laptop that had everything setup to perform the broadcast. There was also another smaller package inside with a note to open it only once she was fully naked during the broadcast. Ashleigh was not looking forward to whatever surprise was waiting in there for her. She sat the laptop on a chair next to her bed and fiddled with different angles and camera settings to see what would look best.

Ashleigh was nervous as the time for the live broadcast drew near the following weekend. She had trouble picking out what outfit to wear and decided to go with a short skirt and blouse combination. It could double as both sexy businesswoman and naughty schoolgirl getup, she figured. Then, it was finally 6pm and Ashleigh opened up the laptop after taking a deep breath. There were already a dozen people waiting in the chat room with more joining every few seconds. (I can't believe I'm really gonna do this. There's almost 20 people online already. Fuck it, here I go.)

Ash: "Hello guys... and maybe some ladies. It's Ashleigh, your executive assistant and college student. How may I help you?"

Ashleigh was caught off guard when the first chat message came in asking her to lick her feet. She did not remember any client with a foot fetish but proceeded with the request after regaining her composure. She was already barefoot, so she moved her right leg up and brought her foot near her mouth. As she didn't have any experience with this, she followed the request literally and began licking her sole.

Ash: "Do you like this? Is this what you wanted?"

"Oh yeah, baby. Now suck on those pretty toes!!" the same person responded.

Ashleigh did as instructed. She was quite flexible so she didn't have trouble to perform the act. But it was a weird experience to taste her own skin and especially her feet.

"Alright, enough of this kinky stuff." read one comment.

"Yeah, let's get the main event started. Strip down for us!" said another person.

This was more in line with what Ashleigh had expected. She brought her leg down and went back to her original seated position on the bed. She flipped her long blonde hair back and began slowly unbuttoning her blouse while keeping eye contact with the camera as much as possible. Once all buttons were undone, she took the blouse off and threw it to the side. Ashleigh turned around and went down into 'doggie' position. With her back side towards the camera, she lifted up her skirt to show off her ass. She obliged the chat requests by slapping her ass a few times from this same position. After that, she lay down on her back and lifted her legs up to take off the skirt.

Ashleigh was now down to her bra and panties. As she expected, there were requests coming in for her to get naked next. Instead, she moved her hands over her body and stuck her tongue out seductively to tease the audience. She knew she couldn't prolong this forever, so Ashleigh finally began to take off her bra. She slowly took off one strap at a time and as she was about to reveal her nipples, she turned around quickly before removing the bra completely. With her top off now, she covered her chest with her hands and turned back towards the camera. After a little more of this teasing, she finally let go of her hands to the delight of the voyeurs.

For the next part, Ashleigh got off her bed and stood closer to the laptop. She touched herself and danced around in a sexy manner while slowly teasing the removal of her panties. The horny viewers were loving the strip tease but couldn't wait to see her pussy. Ashleigh turned around so her firm ass was in direct view of the camera and dropped her panties to the ground. She used her hands to cover her genitalia and turned back towards the laptop to continue the teasing. New chat messages quickly followed asking her to move her hands aside. Ashleigh would do so but not as they had imagined. She moved even closer towards the laptop so only her thighs were visible on the live stream.

Ash: "Here you go. I have moved my hands and am fully naked in front of you all now."

"No, that's not what we meant."

"Move back, dear, so we can see your full body."

"Enough of the teasing, show your pussy!"

Ashleigh couldn't delay the inevitable any further. She hopped back onto her bed and spread her legs to show her pussy at last. The ensuing chat messages showered Ashleigh with praise and some asked her to keep going.

"The tease is finally over, thank you."

"You really are gorgeous from head to toe."

"Keep going. Start playing with yourself, baby."

Ash: "Hold that thought for now. I have a surprise for you all."

Ashleigh had the smaller package placed nearby on her desk. She came back after grabbing it and wondered what was inside along with the rest of the people watching her. Her eyes widened as she finally realized what was inside -- a tan-colored, penis-shaped dildo complete with "balls" at the base. Once it became visible on the live stream, the chat got flooded with requests for Ashleigh to suck on the dildo and insert it inside of her. She wasn't quite ready for the latter, so she brought the dildo up to her mouth and began licking it. (This feels and tastes so weird, but the creeps seem to like it. I guess I'll just keep going and pretend I'm going down on the real thing.) After licking the shaft and around the tip for a while, Ashleigh put the dildo into her mouth and began sucking on it seductively. It was only about 6 inches long, so she managed to take it all the way "balls deep" without gagging.

Some of the viewers expressed that they had cum while others were eager to do the same and waiting on Ashleigh to fuck herself with the dildo. She hoped this would be the last set of requests and proceeded to perform as instructed. She brought the dildo down to her pussy and rubbed her labia with it before finally sticking it in. The phallic dildo kept falling out as she tried to ride it on her bed. Ashleigh changed strategy and used her hands to thrust it in and out instead. The chat messages became more vulgar and additional requests asked her to rub her pussy with her free hand, to pinch her nipples and to stick her tongue out. Once again, Ashleigh followed the requests and improvised further by moaning out loud and faking an orgasm. She was finally able to exhale and end the sexual simulation as no further requests appeared in the chat.

Ash: "Hope you all enjoyed the show and were satisfied. Thanks all, take care."

MrBBL: "Not so fast, I have some more requests for you."

Ash: "Uhm... I'm sorry, I've done everything already. It's too late now, the show is over."

MrBBL: "No, it's not. You are supposed to satisfy everyone and I haven't cum yet."

Ash: "Alright then, what would you like to see?"

MrBBL: "Turn around and let me see that pussy and ass from behind."

MrBBL: "That's good, now arch your back up further and use your hands to spread your ass cheeks."

MrBBL: "What a nice, tight asshole. Now run fingers over your pussy and asshole."

MrBBL: "Good. Now stick a finger inside your ass!"

Ashleigh stopped and turned back around to face the camera. She was already unhappy that she needed to continue but the newest comment was the last straw for her.

Ash: "Look, I've done more than enough and also did your additional requests. I won't go any further."

MrBBL: "You need to be a good obedient slut and continue as long as it takes."

Ash: "Please, stop. I can't finger my asshole. That's just gross."

MrBBL: "OK. Then use the dildo and fuck your ass with it."

Ash: "What?! No, that's... even worse. I've never done anal."

MrBBL: "Do it, you fucking slut! I won't be satisfied until I see your tight ass stuffed."

Ash: "Please, no! I can't, I... I don't know how. Doesn't it hurt? I don't have any lube."

MrBBL: "You must have some oil or lotion around. Hurry up and find something."

Ash: "There's this...no. Please, don't make me do this."

MrBBL: "DO IT SLUT OR YOU WILL REGRET IT!!!!!"

Ashleigh remembered she had a coconut oil cream in one of her drawers. Even though she was only reading prompts from a computer screen, she still felt intimidated by the person with username "MrBBL". She realized she couldn't talk him out of his demands and knew she'd get in trouble if not all the clients were satisfied. After grabbing the cream, Ashleigh came back and sat up on her bed again. She put an excessive amount of the cream over the dildo to be safe and spread her legs apart. She placed the toy near her anus but was nervous and unsure how to continue.

MrBBL: "Take a deep breath, then exhale."

MrBBL: "Relax and push out to widen your hole."

MrBBL: "Keep pushing and insert it in."

Ashleigh was struggling and flinched as the tip entered her tight hole. It felt like her innards were getting torn apart as she finally penetrated her anus. Inch by inch, she kept pushing more of the fake cock into her asshole. The chat messages encouraged her to keep going and eventually Ashleigh managed to insert most of the dildo up her ass. Her next instruction was to fuck her ass by moving the dildo in and out. She slowly started pulling the toy out until only an inch was left in before pushing it back in again. As her anal muscles became more relaxed and she got used to this new sensation, Ashleigh was able to pick up the pace.

MrBBL: "Good. Now, take it out and spread your cheeks apart."

MrBBL: "Love that beautiful gape."

MrBBL: "Keep shoving it in and taking it out until I've cum."

About a minute later, "MrBBL" responded that he had ejaculated and Ashleigh was relieved the ordeal was finally over. However, the rest of the audience had become hornier and wanted to take the anal experience a step further.

"Now do A2M!"

Ash: "Excuse me?"

"Ass to mouth. Take the dildo out and put it into your mouth."

Ash: "What?! That's beyond gross. Why would I do that?"

"You can't have anal without a2m."

"Yeah, c'mon you slut. Finish the job."

Ash: "I can't believe what you're asking. What more do you want?"

"Don't ruin the great show by not ending it on a high note."

"This will be the last request, promise."

Ash: "You better be telling the truth. Fuck, I can't believe this. Let me get it cleaned up first."

"No, no cleaning!"

"No! Put it directly into your mouth."

Ash: "Oh my god, you guys are sick!"

Ashleigh reluctantly brought the dildo up to her mouth. She grimaced, closed her eyes and took it out as quickly as she had put it in. She was grossed out as soon as it touched her tongue. But to her dismay, the voyeurs were not satisfied. The chat messages demanded her to perform the act "like she means it." Ashleigh shook her head in disbelief but continued. She took turns fucking her ass with the dildo again and then raising it up to her mouth to go down on it. She sucked and licked the dildo like she was giving a blowjob, ignoring the fact that it had just been inside her ass.

"Fuck, that's a good slut."

"I can't believe she's actually doing it!"

"Is there anything this slut won't do?"

"Were you there at the big gathering? She even made out with her sister."

"We should get them both on and do another live stream."

Ashleigh had enough of the comments and slammed the laptop lid shut. She was angry at how far the event had escalated and the sexual boundaries she was forced to cross. She immediately went to take a long shower to clean herself up.