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My VideoChat Error Ch 25

Story Info
Shaun(a) eats creampies, ponders matters & has a date with gf.
10.9k words
4.64
15.9k
12

Part 25 of the 32 part series

Updated 06/07/2023
Created 03/25/2016
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I had a sex filled weekend.

A man should feel proud of himself.

However, I did not do the fucking.

I got fucked.

I did not get sucked.

I did the sucking.

There was lots of cum.

Lots of cum.

But it was other men's.

I got to swallow it.

Er, had to swallow it.

Real men's cum.

Dolled up as a woman.

Lingerie.

Makeup.

Even earrings in my pierced ears.

And a caged penis to boot.

Forced by Naughty.

For the past couple months now.

Lots of thoughts occupied my mind since the weekend's events. Lots of them brought about various feelings within me. Lots of them made my penis stir.

The thoughts that predominated in my mind since Sunday revolved around my new 'Marital Sex'. I thought about it last night. Then again today when I awoke it was my foremost thought. In the shower, at breakfast and as I drove to work. It was all I could seem to think about.

I thought about how our roles had reversed. We normally had sex about once a month. Missionary position. I would fuck my wife for between 5 and 15 minutes. We both usually orgasmed. Me for sure.

Last night, I was the one on my back, legs spread. Emma was the one who mounted me. She had a cock, a strap-on cock, a replica of Mike Brown's. It was much larger than my penis.

I lay there all dolled up as a woman, with lingerie, my wig and makeup as she fucked me.

Slowly.

Sensuously.

My wife made me moan.

She looked into my eyes most of the time.

Her eyes twinkled.

And she smiled.

I tried not to enjoy it. But I could not ignore her slow assault on my prostrate. She sawed in and out of me for a long time. Each thrust stroked my prostrate just enough. So long that her breathing had become laboured. Her amazing, large breasts were coated in sweat. She fucked me for much longer than I had ever had fucked her.

Feelings of arousal slowly built up in me. I am sure she could see it on my face.

Those feelings came unbidden.

I could not stop my penis from becoming as hard and erect as it could in its chastity cage. It filled it completely and strained to get out. It extended up from my groin as if it was on display for both of us to witness.

My penis kept betraying my state of arousal.

Every time my wife glanced at my throbbing member, she smiled even more.

I tried to suppress the orgasm she was forcing me to have.

I could not control how her cock made my prostrate feel.

Eventually I could not take it anymore.

I needed to be given release.

Anally.

By my wife's 'cock'.

Yet my impending orgasm would not come.

She made me ask for it. She made me ask her to fuck me faster. To push me over the edge.

I felt as though I was begging my wife to fuck my ass.

The orgasm she gave me was intense. My release so truly powerful.

That I could not deny.

Part of me wondered if I ever had that good an orgasm with her when I did the fucking.

That I cannot allow myself to think about.

Part of me does not want to feel so aroused that I orgasm by being fucked as a woman. It makes me feel so submissive. So emasculated. Having my wife take me while I was all done up as a woman elevated those feelings. Having a powerful anal orgasm enhanced them even more.

I did not have a choice to not be fucked by my wife though. I had to wear lingerie. I had to have earrings. I had to wear makeup and a wig. I am being forcibly feminized. I am still being blackmailed by Naughty.

A person whom I apparently know and who definitely seems to know me. Blackmailed because I had hurt this person somehow. What exactly I had done they would not tell me.

Yet.

I still need to figure out who this person is and why so that I can find a way to end this.

Monday almost 9 am.

As I approached my office my hot brunette secretary Denise flashed me her wonderful smile.

Always impeccably attired, today she wore a light blue blouse, tight, navy blue skirt, navy blue stockings and dark blue heels. Thick dark blue bangle bracelets adorned her wrists, bright red polish coated her pointy nails.

Her face was just as perfect with her dark blue eyeshadow, curled lashes, light red blush and bright red lipstick.

Oh, and her amazing blue eyes.

"Hello Shaun," she said with a sparkle in her eye.

She was also my girlfriend. Forced but still my girlfriend. The one aspect of my blackmail that I have truly enjoyed was Denise.

"Hello Denise," I replied with a warm smile as I headed into my office.

Before I could sit down Denise had followed me in and closed the door. I turned and found her pressing her shapely body into mine and her luscious, soft, red lipstick coated lips onto mine. It was amazing. A gorgeous woman like her, a true ten, with a great personality and she wanted me.

Me.

Yes me.

She was forced into this relationship by Naughty as well but like me, she has grown to be close to me and truly has become more than my mistress but rather be my actual girlfriend.

A real one.

I loved both her and my wife.

It's complicated.

Kissing Denise always brought up a feeling of joy inside me. A feeling of hope. A feeling of happiness. With all that has happened to me I allowed myself to be lost in those feelings as we shared warm, loving kisses.

I needed hope.

I needed happiness.

After a few minutes we broke our embrace.

"So tell me what happened after our last texts on Saturday night. You were kinda vague on Sunday."

"Well, I had a good sleep Saturday night," I stated.

"Sl-e-e-p," Denise repeated slowly, surprised by my answer.

"Yes. Sleep. Emma came home and did not wake me. She did not make me eat her out. Odd. Instead she cuddled and I was able to sleep in 'till late Sunday morning," I explained.

"Second best part of the weekend," I said with a smile.

"And the first?" Denise asked tilting her head a bit towards me and looking me straight in the eye.

"Spending time with you of course," I said after a brief but dramatic pause.

"Right answer," Denise said playfully and grinned in response.

"Lots happened though," I offered.

"Lots."

"Now I am to dress femininely all the time at home. In fact, whenever I am not at work. And I thought it was bad when it was just lingerie under my man clothes," I explained.

"Speaking of which," Denise said with a naughty tone to her voice, "What lingerie are you wearing today?"

My Lingerie. Yes my lingerie. I had almost forgotten it was below my business suit as I was always wearing some. Now I could feel every piece of lacy, feminine finery that was on me. From the lacy red bra, to the lacy red garter belt, to the sheer red stockings and to my pinky-red panties.

"Lacy red."

"Mmmmm, I love red. It's so hot," purred Denise. "But how does that work since you have a family?" she asked before I could comment on her non-comment.

"Nick and Natalie dropped by and took the kids to her parents' cabin. For the summer."

"Oh my," Denise gasped unexpectedly.

"Yes. Nick also took my wife upstairs and had sex with her," I added looking down.

Another gasp from Denise.

"With you and Natalie there?" She asked incredulously.

"Yes. And his wife did not seem too happy about it."

"Well, what woman would be if your husband was fucking your sister instead of you and pretty much in front of you," Denise commented as she shook her head.

"Natalie even said aloud that Miranda would not be too happy, as if to dissuade him."

"Really? She mentioned Miranda? So she is somehow part of this too?"

"Yeah, I wonder if Natalie is also being blackmailed. She was also wearing a chastity belt. She whispered that we would talk another time. She could be the key to unravelling the mystery surrounding Naughty. I hope that this is not just a wild goose chase," I said with guarded excitement.

"Really? She is also in chastity?" Denise said unabashedly wide eyed.

"Yes," I replied.

"I wonder who put the chastity belt on her? Was it her husband Nick? Naughty? Or maybe even Emma? What did she do? Is she being punished as well? How is your sister-in-law connected to all of this?" Denise pondered out loud.

"I don't know," I replied as I shook my head. "I have been mulling it around in my mind ever since. Maybe its unrelated? Not sure," I added.

"Hey, why don't you contact Natalie now and arrange a time? Find out what she knows. If nothing, then nothing ventured, nothing gained. Maybe she is just as much in the dark as we are," Denise quipped enthusiastically.

"You're right. I will right now. I need to be careful though, Nick might be monitoring her," I said with some excitement. "Nick does do surveillance work etc. as you know," I added.

"Hey Nat, thanks again for picking up the kids and taking them to the cabin for us." I typed with Denise looking over my shoulder.

After a few moments Natalie replied.

"No problem. It was our pleasure. Nice to spend time with my sister's and your kids."

"With you guys popping in and out, and the movie playing, none of us really got a chance to chat. We should get together again sometime soon," I typed.

There was a long pause.

Was she going to reply?

"It's always refreshing when the adults in the family can have lunch together away from all the kids. Just like in the old days! I will let you know sometime soon when that could work." Natalie replied.

Denise sighed and moved back to my side,

"Ok, guess it was nothing gained. You won't be able to talk openly with her if all four of you get together," Denise stated.

"No. She actually said lots with so little," I replied excitedly.

"Huh?"

"I think she put a secret message in there, one that only I would understand," I added.

"Really?" Denise stated quizzically.

"A few years ago, Natalie and I were planning a big surprise party for Emma. We met a couple of times. Each time she had Nick take Emma and all the kids to various 'kid' things, like the circus etc. Emma bought the story that Natalie needed a break from kid things. Emma and Nick always were more enthusiastic about kid things as it was anyways. Natalie and I laughed each time about how it allowed the 'adults' in the family, meaning her and I, to have lunch together and talk about life besides planning the party. Each time she told me that it was a refreshing break," I relayed.

"So, now what?"

"I guess we have to wait for Natalie to contact me."

Just then my phone dinged.

We both looked at each other expectantly.

It was Naughty.

"Take off your man clothes and log into the video chat. Do it now," Naughty commanded.

Denise helped me out of my business clothes and folded them neatly on the corner of my desk.

I sat there clad only in my feminine finery — red lace — bra, panties, garter belt and stockings. All picked out by my wife Emma this morning. Denise stood behind my chair as usual. Naughty would be able to see us but we would not be able to see him/her. Naughty never gave us a video feed.

We waited.

And waited.

10 minutes.

No Naughty.

15 minutes.

Then someone logged in.

And we were getting a video feed!

To my surprise Miranda was on the screen. The first time we ever saw anyone in the chat. Was she—

"Something came up that Naughty has to attend to right now. I am here instead," Miranda began.

The hot blonde was sitting behind a desk apparently in an office. Miranda was wearing a classy white blouse that barely seemed to contain her more than ample cleavage. Her makeup was exquisitely done. She also wore expensive diamond earrings. Her amazing blue eyes, accentuated expertly with eye shadow and curled lashes, looked right at me. As she spoke her luscious looking red lips moved sensuously.

Seeing her brought me back to last Wednesday. She had so erotically and dominantly made me eat her out. She had stood commandingly above me while I knelt before her and worshipped her naked, cum filled pussy.

Much like when a man gets his cock sucked.

When a woman submits to a man.

Only she was the man.

And I was the woman.

I felt so submissive around her.

She had a way about her. She was in control. Everyone else was expected to obey her. And did.

I could smell her dominating womanhood as if I were kneeling before her right now.

I felt a wave of submissiveness wash over me.

My penis stirred in its cage.

My heart beat faster.

No.

I could not think like that. This was Miranda. If she was not Naughty herself, she was certainly Naughty's right hand. Several times now she had spoken with the authority of and authorization of Naughty.

She was part of why I was in this predicament.

Still my penis was filling my chastity device.

My arousal I could not quell.

"I have a lot to do too, so I will get right to the point," the hot blonde continued.

"You were great on Friday night Shauna. You were eager and willing. You really seemed to satisfy your boyfriend's carnal desires with your ass and your mouth. Keep up what you are doing. Your training is coming along well," she added.

Again she was referring my training.

"And on Sunday when Nick went and well, was Nick, you took it in stride. You were a good husband and took care of your wife's needs afterwards. It was also your first time having your new marital sex, so your hesitation can be understood. Be more eager and willing from now on. Crave Emma's cock as much as you crave Jason's. You will be getting a lot more sex with your wife now than you ever did before." Miranda stated.

Crave Emma's cock?

My mind again flashed back to yesterday. My wife was naked. I was dressed all in lacy white lingerie, complete with makeup and my wig. I was Shauna once again. I lay there on my back, my legs spread as my wife was slowly fucking my ass with a big, long, thick strap-on. A replica of Mike Brown's cock. My wife looked me right in the eye as she thrust in and out of my ass. She made me ask to get fucked faster. I finally gave in to my physical arousal.

That was totally embarrassing.

My wife smiled as she gave me an anal orgasm.

My breathing picked up.

My penis so felt the walls of its restraining device.

I tried to shut the thoughts out.

I was getting horny again.

But, more sex like this with Emma?

I should have expected it, but still was taken aback.

I remained silent.

"You also willingly dressed appropriately at home after your family left. In addition you did as Emma asked in all other ways without hesitation." Miranda added.

I felt so feminine done up entirely as a woman for the entire evening. Over top of my lacy lingerie and stockings, I had worn a blouse and skirt. The wig and makeup remained on 'till bed time. That was supposed to be my new normal at home now.

I was all done up as a woman and I was caged and plugged.

I felt so submissive.

"You have earned a choice," Miranda stated breaking my train of thought.

"Huh?" I stated at the unexpected turn of events.

Being feminine and submissive gets me a reward?

I hesitated, truly not understanding.

"I have earned a, a choice?" I said in disbelief, finally finding my voice.

"Yes. Your good behaviour and acceptance of your training have pleased Naughty a lot," Miranda stated.

She opened her red painted lips but hesitated and drew in a breath before continuing.

For effect.

"For now you can decide whether you wear a butt plug when you sleep, or not. Your choice," Miranda announced.

I sighed a little in relief. I did not have to wear a butt plug at night anymore? That seemingly small thing raised my spirits a lot. I could not have imagined how good that felt to hear those unexpected words.

"Thank-you," I found myself saying with sincerity.

I had grown accustomed to having a butt plug in me, but being able to choose whether or not I used one felt good.

"But," Miranda continued with a naughty gleam in her eye, "If you falter, you can expect to have that reward rescinded. Keep up being a good and eager Shauna. Keep up being a good husband. Don't hesitate to do as you are told."

Miranda paused and looked right at me.

"Submit to your boyfriend, submit to your wife, submit to me. And to anyone else you are told to submit to," Miranda added.

She paused and still smiled as she looked at me. Not just a friendly smile but also a mischievous one.

"When are you seeing your boyfriend again?" She asked changing to a more conspiratorial tone.

"Tomorrow night. We are going out to see a movie," I replied more gleefully than I had wanted to.

Being given a choice by Naughty.

Thats why.

It had to be.

"Good. Keep him satisfied, keep draining his large balls," Miranda said still smiling.

"Naughty will be in touch. Have a good day," Miranda concluded the video chat and signed off.

She seemed kind of hurried.

"You still did not tell me everything about Sunday. Apparently you left out your new 'Marital sex'?" Denise said with her head tilted to the side and her succulent, red lips parted in mock shock.

I looked back at her feeling bad that I had not gotten to that part yet.

"Now I am more intrigued. So Emma let you out of your cage and you —" Denise continued not waiting for me.

"No. It was not like that at all. I only wish she could let my penis out of this contraption," I began and paused to take a breath.

My penis was twitching in its cage.

Good thing no one could see it.

Denise continued just standing there looking expectantly at me. A bit of a grin was forming at the corners of her mouth and her eyes began to twinkle a bit.

"Well, I did not get to fuck Emma. Emma did the fucking. She used a strap-on, a clone of Mike Brown's cock apparently, she mounted me and took me missionary style. All the time she looked into my eyes and made me beg to be fucked hard, beg for anal release," I said looking down.

My penis was filling up its tube again.

"And did you?" Denise asked expectantly.

I hesitated.

I felt so ashamed. Our new husband-wife sex involved Emma fucking my ass. Not me fucking her.

I looked down to the ground.

"Yes. I could not help myself" I finally uttered.

Denise rubbed my shoulders and kissed me gently on the cheek.

I could not stop thinking back to my 'deflowering' by my wife. It had been on my mind ever since. It was the first time she ever fucked me. It felt so submissive to be wearing lingerie, makeup, earrings and a wig. And to be in the traditional missionary position with my legs spread. Like a woman. I could see her put the clone of Mike Brown's cock in my ass, I could feel it sliding in and out of me. I could feel her bottom out with it.

I remembered how agonizingly slow she did me.

How powerful my release was when it came.

After I had asked her to give me an orgasm.

More shame filled me as I thought about getting laid by my wife as the 'woman' and unwillingly taking pleasure from it.

My penis ached in its cage.

It shouldn't at these thoughts but it did.

"How did Emma react?" Denise asked unexpectedly.

I hesitated.

Her tits looked so amazing as they bounced while she fucked me. Her areoles so puffy, her nipples so erect. She seemed truly turned on by fucking 'Shauna'.

"My wife was aroused, very aroused," I began. "I could see the excitement on her face. Her nipples were erect and her chest flushed," I added.

"Funny thing is though, Emma seemed to want to pleasure me. She seemed to want me to enjoy myself. As Shauna though, not as Shaun. She kept telling me that I had to ask her to go faster and that she knew I wanted her to. It made me feel as though I had to beg for release. But maybe she only wanted me to openly desire that she give me release with her 'cock'," I added.

"Why did she think I wanted to? If she really thought that," I asked almost rhetorically.

Had she wanted me to give into the feelings that part of me has felt? So that I could better enjoy being fucked as a woman? Why would my wife want that?



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