My VideoChat Error Ch 10

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Trip Pt I Shauna is forced to have anal orgasm.
6.2k words
4.72
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Part 10 of the 32 part series

Updated 06/07/2023
Created 03/25/2016
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Monday morning arrived, and Denise and I would embarking on our trip to our new clients city. We met at the office to pick up files and our laptops. Denise also brought her bag in so that we could load up my lingerie and toys without anyone being the wiser.

I logged in to get final pre-trip instructions from Naughty at 8:59 am.

"Put on your white lingerie set. Do it now," began Naughty.

I will stop at a gas station and take this off once we are on the road, I told myself.

I then did as I was told....

"Give yourself an enema. Do it now."

I put my man-clothes over top of my lingerie clad body and went to the bathroom.

When I returned Denise came into my office with her bag. Naughty of course had further instructions for us.

"Denise, kiss Shauna passionately as you undress her, then lube Shauna up and put her butt plug in. Do it now."

Denise smiled seductively as she approached me. She then embraced me and began a passionate kiss. My lips parted willingly as soon as I felt her tongue. As our tongues entertained themselves and our lips were lovingly playing, she was unbuttoning my shirt and unbuckling my pants. All too soon it was over and as we broke our embrace, I stood there only clad in white lingerie.

Denise applied some lube to her fingers. Then she bent me over and spread my legs a little and applied the lube to my asshole. Instead of working a finger or two in as she usually did, she just rubbed the butt plug a bit at the entrance to coat it and then pressed it slowly in and out till it was fully embedded in my ass. She only needed to pump it in a couple of times to get it in. It went in with only a little resistance.

My ass was getting used to being plugged. A man's ass should be a one way exit only I thought, dismayed that the plug went in so easily.

Denise pulled me to my feet and with a smile said "Naughty said its my turn." She then handed me her egg.

I took Denise in my arms and began a passionate kiss as I hiked up her skirt a little and reached for her panties. They were wet, like they often seemed when we played. I rubbed her clit a little, feeling a bit naughty myself. That brought an audible moan from my hot secretary. Then I slid her egg into her love canal and pushed it up. I brought my fingers to her nose so she could smell them. As she opened her mouth for them I stuck them in mine and licked them clean.

"Hey!" she said as She giggled a little.

We turned to the screen and got further instructions for our trip. I put my man clothes on and we took our stuff to my car. Once we had that loaded we added the clothing and lingerie purchased on Thursday and stored in her trunk.

As soon as we were ready to leave we both set each others vibrator to the first setting, as we had been instructed. Second setting was to come an hour from now till we got to our hotel. Naughty had anticipated my thoughts of changing and at random times he/she would text us and Denise would have to take a picture of me, showing my lingerie while driving.

Beyond that Denise and I had very interesting conversation throughout the trip. We both found out so much about the other and discovered that we had more in common than we realized before.

At the hotel our rooms turned out to be adjoining. Hers was a room with one king size bed, a recliner, a small table and a desk. Naughty told her that she would not be sleeping there.

My room was a suite. There was a living room space with a couch, an easy chair and a table, a kitchenette and a separate bedroom with one king sized bed.

Even though my company paid for the rooms, they had been booked by Denise and to my chagrin, vetted by Naughty. He/she had specified rooms like these, with a connecting door. We were also told that he/she had arranged for cameras with mics to be installed in every room, even the bathroom, by someone. Not permanent of course, but here till we leave, so that he/she could record our evening activities. Those had not been revealed yet. Naughty indicated that they worked very well in low light conditions and had a high resolution. Every detail of our carnal activities in my room or hers would be recorded. We had also been reminded to show progress.

As per our instructions, we took my lingerie out of our bags and laid them out in specific drawers of the dresser in my room. My work clothes were hung up beside my Alice outfit and my blouse and skirt. Denise's clothes were also hung up and put in the dresser in my room, not hers.

As she was my girlfriend now or as some might call her, my mistress, albeit forced by Naughty, we were to dine and sleep together as lovers would.

As we opened the specified drawer to lay out our sex toys, we noticed that there already were several dildos etc in there. Denise gasped at the sight of the very large toys. I sighed in dismay.

My phone pinged, I had a text message.

It was from Naughty.

"I see you finally found my gifts for my favourite erotic couple. New toys for you both to enjoy. Shauna, I want you to take the big black vibrating dildo and pleasure Denise on the bed. Make it wet with your saliva first. Do so until I text you again. Keep the phone within reach."

We both were surprised by the turn of events. We returned to the open dresser drawer. There were several large dildos. Much larger than my own penis, more the size of Mikes big black cock.

I picked up what had to be the big black dildo and we moved to the bed.

My jacket and shoes were already off, so I took off my tie before I began to get onto the bed.

My phone pinged again.

"Denise, take off the rest of her man-clothes. Keep your blouse and dress on though. Do it now."

We were used to undressing each other erotically by now. We embraced each other and began to kiss passionately. I realized suddenly that Naughty had not specified passionately. We just did it naturally on our own. Was this just expected progress or something more?

Our lips were locked and our tongues exploring. Even though I am married and this is a forced situation, I always enjoy kissing my hot secretary. It shouldn't but it felt so right.

As my buttons were already undone, we worked my shirt off, tongues still playing. Soon my belt buckle was undone and my pants were off. When my socks came off I was standing there in front of Denise, clad only in white lingerie.

My penis was stirring though from the intimacy we shared and her hotness.

We got back on the bed, maintaining physical contact the entire way. Once there, I motioned for Denise to hike her skirt up. It wound up bunched around her waist. Then I hooked my fingers into the sides of her panties and pulled them past her garters and off her completely.

"Suck on that cock for me, suck on that big black monster Shauna," Denise said seductively.

I held the dildo with both my hands and took the head of it in my mouth. I both sucked and slobbered all over it as I slid it in and out of my mouth. I moaned as I did so.

"That's fucking hot Shauna," Denise said huskily. She turned up my vibrator back to the second setting.

I gasped as I was not expecting that.

I looked up at Denise and saw a naughty grin on her face.

I did the same for her and turned up her vibrating egg.

She moaned and squirmed a little. Her right hand moved to her clit and the left to her right nipple. Her top three or so buttons were undone, undoubtably while I was sucking on the dildo.

I then proceeded to lick up and down the shaft of the big black dildo, and added a few more soft moans.

"Put that bad boy in me Shauna," Denise said with some lust in her voice.

I took the head of the big black dildo back in my mouth and bobbed up and down on it.

"Give me that cock Shauna."

I could see that she was frigging herself faster now and that her other nipple was getting some attention too.

"Do you mean this cock?" I asked with a playful voice, still licking as I spoke.

"I need that big black cock! Give it to me now Shauna!" Denise exclaimed excitedly.

I moved in as she spread legs while I pulled the cock from my mouth. I then reached in and pulled the still vibrating egg from her quim. As I began to rub the head of the dildo at the entrance to her pussy, she suddenly grabbed it and shoved it in.

She gasped and then moaned. She must have shoved it 5 inches in. I grabbed the base, turned the vibration on and began thrusting it in and out of her.

Denise moaned in pleasure and began to buck her hips. She really wanted it badly.

Soon I had almost the entire length of it buried in her pussy. I thrust in unison with her hips.

"Kiss me now, I need to kiss you!" She exclaimed frantically.

I repositioned and my lips were on hers.

She kissed me with more passion than ever. Then suddenly she cried out.

"I'm cumming, I'm cumming!"

Her body spasmed and tensed up. I could tell it was intense.

When it subsided she motioned for me to stop the vibration and to move up and cuddle her in my arms, which I did but I left the dildo buried in her.

She kissed me softly on my lips and then looked into my eyes. A softness had replaced the lust in her eyes. They were truly beautiful, more so than I had ever realized.

"Thank you, I needed that, more than you can imagine. The egg and all the erotic stuff put me over the top. On the weekend my boyfriend seemed to argue with me repeatedly. It all started while he was fingering my clit on Friday. I had just blown him and swallowed every drop like he likes. Then just as I was building up to an orgasm, he suddenly wanted to talk about how I shouldn't be going on this trip. Do you know why?"

"Why?" I asked as I snuggled her in closer to me.

"Because I wouldn't be at his place to cook and do dishes. Not because he would truly miss me, but because he would have to do that himself. My orgasm never happened."

"What, when you are at his place? He doesn't do those duties for you at the very least?" I asked kind of in shock. It seemed a no brainier to me to do my share around the house and when I had my own place I did all of it.

"No. He always claims I do things better. And plays that card. I do it because I love him. It was a rough weekend."

My phone pinged again.

We both looked at each other and then I grabbed the phone. Somehow we got caught up in the moment and forgot about the situation. My hardon had died. I honestly forgot that I was in lingerie, and I forgot about Naughty. Wow.

"Touching. Honestly it was. Now back to business. Shauna, assume the position. Denise take the cock out of your pussy and fuck Shauna's ass. Don't touch her little penis. Do it now."

Little penis? I thought as I got up and on my knees. I know my penis is not anywhere near as big as Mikes monster. But little penis?

My thoughts were interrupted by feeling Denise pull my panties down to my knees an then pull the butt plug out. She shut it off, then pulled the dildo out of her pussy and put the head at the entrance of my ass.

"Ask me to fuck your ass Shauna," Denise said mischievously.

"Fuck my ass Shauna," I replied with a grin.

"No silly, say it like you mean it and ask ME to fuck your ass," she retorted in mock anger.

"Fuck my ass. Fuck my ass with that big black cock!" I stated firmly.

"If you insist," she said with a giggle as she pushed the large head of the dildo in just past my anal sphincter.

I gasped. It was as large as Mike's cock. Larger than my butt plug. Did I just think my butt plug? Yes. Larger than my penis. A piece of plasticky latex was more my than-

My thoughts were cut short as Denise pulled it almost back out and then pushed it back in again. This time much deeper.

I gasped.

It made me feel so full and like I had to go. I was so glad that I relubed my butt plug fairly generously at our last bathroom break as we drove over here. Or it would definitely have hurt.

Denise took it slow but began to pump the very large black dildo in and out of my ass.

"This is so hot Shauna."

All I could do was moan uncontrollably as she thrust it back in and deeper, and picked up the pace.

"Mmmm, I see that your penis is rock hard, that along with your moans say it all," Denise said seductively.

I felt humiliated. Why do I keep getting hard when I am dressed in lingerie and have a -

I gasped loudly at that moment. Denise had slightly re-angled the dildo and found my prostate. That really felt good.

Again as she thrust she stroked it.

Again I gasped.

My penis seemed to grow bigger. This felt so good. I could not deny that.

She kept it up and I began to pant.

"I think we have found your G-spot Shauna," she said huskily.

Just as I began to build, yes build to an orgasm, without my penis being touched, she stopped and re-angled.

"Ughhhhh," I moaned, "don't stop now."

I had to say that. It felt really good.

"Fuck me Denise, I need to cum."

She held the dildo still. I tried to push back on it and fuck it myself. That did feel kind of good, but did not hit the prostrate.

"Naughty's orders. He/she texted, you are not to cum. Not now."

She pulled it out and I looked back.

"Sorry," she said and hung her head. "I wanted to pleasure you like you did me."

I really wanted to cum, but thought better of crossing Naughty.

After my hardon had subsided we got dressed and headed for dinner. My butt plug was put back but not turned on. Part of me wanted it on setting three. That might do it. It was on setting one.

Immediately I tried to dismiss that thought. I glad I did not cum from that dildo, I told myself. A man does not cum from his ass. Denise will stroke me later, or blow me, like she did back in the beginning, and I will cum.

Those disparate thoughts went through my head all throughout our dinner as Denise made nice small talk with me.

Several times she put her hand on mine and looked into my eyes. And then told me she would see to it that it, it being an orgasm, happened for me before it was time to sleep. She knew how it felt to be denied.

It felt like we were really bonding. Like we were really getting close.

When we got back Naughty texted us more details about tonight. Mainly that we were to sleep together in the same bed, showing lots of intimacy. Also that I was to sleep in my frilly pink camisole, panties and slip.

Then he/she wanted only Denise to read about our sex acts for the rest of the night. We were to get our instructions and follow them, ad-libbing as needed. Naughty warned us that we should not need more details, and if we had to be interrupted by too many texts, we were not complying and...

That threat was not elaborated, but it was clear. We were to show progress or be outed. Our compliance was expected.

Denise then spent awhile texting back and forth with Naughty. I hoped that Denise understood clearly and that I would climax. I felt so horny.

When they finished, Denise locked her phone and smiled at me. She told me to put on my white lace gloves and heels and to wait in the bedroom till she called for me. I was to practice walking in my heels till then.

She then left our room with her purse and told me she would be back shortly. While she was gone I did as I was bid, namely I practiced walking in my heels, dressed only in hot lacy lingerie.

After about 20 minutes I heard the door open. Denise let me know that she was back but that I was to stay until called upon.

I was hoping to be done pacing in my heels, yes my heels, but alas no. I decided to keep practicing since the cameras could be on.

After another 10 minutes I heard Denise talking to someone at the door. I froze. Was someone going to be visiting us tonight? The other voice was definitely male. She specified adding the lacy elbow length gloves and practicing my walk. Was I going to be entertains a man tonight? Would I be kneeling in front of him decked out only in lingerie and worshipping his big black cock? Would I be swallowing a massive load of his gooey spunk? Would I be on all fours on our bed while he mercilessly pounded my ass with his massive piece of manhood? Was this why Naughty said I was not allowed to cum earlier? Was I saving myself for 'my man'?

I felt scared and humiliated already. I knew it, I was going to be submitting to the big fat cock of a stranger. I would be forcing him to give me his seed and them thanking him for it. Part of me felt excited at the prospect of climaxing. Part of me revolted.

Then they stopped talking and the door closed.

Then Denise called me.

My heart leapt into my throat.

I hesitated.

She called again.

I had to go. Now or now.

I took a deep breath, opened the door, and did my best to walk nicely through it in my heels.

To my surprise there was no one but Denise there. She was sitting on the couch, with a warm friendly smile on her luscious red lips.

My surprise must have been obvious.

"Show me how well you walk and come sit down beside me Shauna," she said as she patted the spot right beside her". "Naughty was very happy with our progress today and he/she ordered us some expensive champaign!" She paused seemingly to smile warmly at me.

"I said that maybe you would prefer beer, but Naughty insisted it be something we could drink out of wine glasses, like real ladies do." On the coffee table in front of her was an ice bucket with a bottle on ice, and two tall wine glasses were right beside.

"Now come over here and sit with me," she insisted cheerfully again patting the spot right next to her.

I did my best to walk nicely in my heels over to her. Only stumbling a little.

"Good job," she encouraged me as I took the spot she was indicating right beside her. We were sitting as close as two intimate lovers would.

Denise told me to turn her egg to setting one and I felt her do the same for me shortly thereafter. We had been on two for the past 10 minutes. I felt so aroused.

She leaned over and began kissing me very intimately. I returned her amorous attentions, not sure how much of it was her and how much was directed by Naughty.

As we broke our tongue lock she whispered loudly "you are such an intimate kisser, I like that." She then dragged her lips open-mouthed lightly across mine again.

"Naughty has the whole evening planned, might as well sit back and enjoy it. Just for us two. No one else."

I sighed in relief, my fears would not be realized. Not tonight at least.

Soon we were drinking champaign like women and watching porn, as directed by Naughty. We were also in constant intimate contact with one another. Besides kissing, there was a lot of soft caresses that were shared. Denise insisted that we play a lot with each others nipples and the area around them. Mine were surprisingly more sensitive than I thought; no one had ever spent that much time softly working my nipples over. Denise took some time to fondle my penis and balls a bit too, but not enough to bring me to orgasm. Her touch was very tender.

The first video we watched had several hot looking, big breasted women engaged in the usual sex acts with men with large cocks. They sucked on them, took them in their pussies and in their asses.

Several of the anal scenes had the men pistoning in and out of the women and deeply too. Now that I was taking cocks anally, not by choice, but taking them nonetheless, I watched those scenes more intently. I understood what it was like. The vibrating butt plug in my ass was arousing me more now..

I was also was surprised at how easily these women opened up their asses for these large cocks and how deeply they took them. They seemed just as able to take a large cock deep in their ass as in their pussies. I wondered if I was going to have that much anal sex that it would seem as natural for me as for them.

Every time a woman took a big cock in her mouth it reminded me of how it felt. I tasted cum every time they got a facial. My ass twitched every time a woman was fucked. The video had me reliving my recent forced sexual exploits.

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