My VideoChat Error Ch 28

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

I continued to cuddle with him and snoozed for a bit, allowing myself to enjoy the feeling.

Just like Denise said to.

After a while I started to feel my garter belt, stockings and bra on. I must've passed out before getting undressed. I remembered lying down while I was thinking about things.

I realized then that I should go to the bathroom soon and and properly doll myself up so that I would be ready to be fucked again by Jason. I figured that If I wanted to truly arouse him as much as possible, I should offer him a hot looking girlfriend and a nice clean ass to use for his pleasure. And perhaps he would give me some pleasure.

Again.

I shuddered at that thought.

When I finally extricated myself from his arms and got up part of me felt sad as it had felt nice being cuddled.

A chill went down my spine that woke me up more.

I could not feel like that.

I must be getting myself too much into the role of Shauna.

That's it I convinced myself and I felt more at ease again,

In the bathroom I tried only to focus on the task at hand. I had to become the hot little number called Shauna, not a pale imitation of her.

I had to admit to myself that even if part of me did like Shauna and wanted to listen to Denise about enjoying it for now, part of me still wanted to return to just being Shaun.

Part of me felt, I could not describe it, flattered? honoured? more open? after talking to Mandi and Kayla. They seemed so accepting of me as Shauna, believing that I had accepted the femininity in me.

It was almost like they were on board with Denise even though it was obvious that they did not know how far things had progressed for me since they each last saw me. And they didn't know Denise any more than they knew me.

It did feel good to be accepted. They did not just accept me though. They seemed supportive of me as Shauna. That made me feel both good and odd inside. They knew I had a penis in my panties but did not treat me any different than the other girls. They even told me I was one of the girls now. They would be great friends for someone who really was switching.

Or.

Was that Naughty speaking? Mandi was Michelle's handler at the party. She did say she still was a handler of Michelle for the wife. What really was the connection there? Did she work for the wife? Did she work for Naughty? With Naughty? She did seem to know Mike Brown well. Too well in fact.

Did she compliment me to push Naughty's agenda forward and feign innocence to my situation? Or instead did she work for Naughty but was not in the know about the details about me as Naughty kept that on a need to know basis? Or was she truly an outsider to the Naughty regime and just there to be a handler for Michelle to free up the wife so she could indulge herself freely?

Lots to ponder.

It will be interesting to see what Denise thought.

I realized I was thinking more and doing less. I hurried up and finished my toiletries and became a good looking Shauna again.

When I got out of the bathroom Jason was already up and sitting naked on the couch. His body looked so truly masculine.

"I thought you would never get out of there," he chuckled lightly. "Boy you women sure take awhile in the bathroom," he added as he chuckled some more.

I immediately looked at his semi-flaccid member. It was big even when not erect.

I felt a tingling in my groin.

"Man are you something to look at when you doll yourself all up like that," he said complimentarily.

That made me feel a twinge of femininity inside.

He approached me, took me in his arms and coerced me into several passionate kisses.

Instinctively I took his cock in my hand and stroked it lightly.

"Those were great good morning kisses. I would always want to wake up if I was greeted like that in the morning, every morning," Jason said.

I could feel that his member was growing in my hand.

"Mmm that feels so nice," he uttered.

"I love the feel of your cock. Its so big and manly," I stated erotically.

He kissed me some more as I stroked his cock between us. As usual it felt so thick in my hand and so masculine as it hardened.

My own penis was growing in its confinement.

"If you would excuse me for a few minutes I do need to use the bathroom and when I get back we can play some more before we have to leave. I so want to give you more of my love," Jason said while looking excitedly into my eyes.

When Jason got out of the bathroom he sat down beside me still completely naked.

He turned a bit to better face me.

"I have something to ask you but am feeling a bit nervous. Well more than just a bit. Even though we have given our bodies to each other again and again, oddly enough I feel like a school boy about to ask a girl on a first date," Jason explained without his usual confidence.

I wondered what it was? He felt close enough to put my hand on his groin, to feel me up, to bend me over and make love to my ass. What could be so hard to ask?

"What is it?" I asked as openly and as femininely as I could. "We know each other intimately, so I don't know what could be hard to ask about. Please tell me," I said softly as I caressed his near shoulder lightly with my hand.

I wasn't sure if I should feel nervous or excited.

"Well, there is this concert, and well, um," Jason started and paused.

My inner concerns dissipated. He wanted to ask me out to go to a concert. He did seem like an innocent school boy!

"And," I added to convince him it was ok to continue. I did not understand why it would be this hard to ask me to a concert.

"Ok, I should just say it. I have never been good at asking girls out. You probably noticed that on our first meeting," Jason said with a light, but still slightly nervous chuckle.

He did not seem like the suave woman's man many men try to be. I giggled lightly.

That seemed to lighten the mood a bit.

But just a bit.

"Two weekends from now, about a five hour drive from here there is a concert by that band you and I were talking about the other day. That great 80's band. It would mean going up on Friday night and coming back Sunday, likely late in the afternoon. Would you go away for a weekend with me Shauna?"

I could see in part why he was nervous. It wasn't just a concert. It was a weekend getaway. As a couple. I would be Shauna the entire weekend. I would live as Shauna for two days. No breaks. No Shaun. And be his devoted, eager girlfriend. And very much in public.

I was a bit shocked. I stared at him not knowing what to say.

He still looked hopeful.

"That would be a big step for us," I replied, recovering from my shock.

"It would mean so much to me to spend the weekend with you. Just you and me," Jason said as he looked into my eyes.

Our relationship would be moving fast, but it would be the kind of progress Naughty would want to see.

Naughty.

Yes Naughty.

Crap.

That would be the weekend of Naughty's monthly party. I was sure I would be expected to be there and perform as Shauna.

Again.

I could not tell Jason that.

I could not tell him about the party.

Ever.

"Well, I would like to, but I think my wife might have plans for us," I replied not sure how to say it.

I could see him deflate a little. Well more than a little.

"But, I wasn't really listening to her that closely. Sometimes she goes on and on and on about us doing some things together," I giggled a little bit.

"Yeah, I know the feeling," he said with a slight chuckle.

"No its ok, I know its kind of a big thing and maybe its too soon for us to be travelling together. I understand," Jason said acceptingly and sounding a bit rejected.

"No, I am excited by the idea," I continued realizing I had to sound more enthusiastic about his proposal. "I just need to get the ok from my wife or I will truly be in the doghouse. I really would like to go, honestly," I added.

I slid my other hand up over his chest to his neck and drew him into a wet kiss with lots of tongue.

I needed to initiate this kiss.

And sensuously.

He readily responded.

"But-" he began pulling back a little.

"You are not trying to back out on me now after just asking me out?" I said with my head tilted a bit towards him and my eyes looking into his playfully.

"No, I am certainly not," he chuckled lightly.

I lowered my hand to his crotch.

I began stroking his cock while looking mischievously into his eyes.

"Let me see what magic I can work and I will get back to you on it, 'kay?" I stated with a sincere smile.

I had often wondered how I would get out of Naughty's party. This just might be the ticket. Naughty might want me to be cementing my relationship with Jason rather than being a 'cum bucket slut' for his/her party patrons.

"Sure babe," he said sounding much better and continued kissing me.

It did not take long for his cock to get rock hard. I slipped to my knees in front of him and looked up into his eyes pleadingly.

"You sure do love my cock Shauna," he chuckled and spread his legs so that I could get better access to his cock and balls.

I kept stroking him while I lightly licked the head of his cock.

He gasped right away and let out a little moan.

I licked and stroked while looking up into his eyes.

The submissive feelings I felt I am sure he could see in mine.

"I want to pleasure your cock with my ass," I said erotically.

I needed to show him that I wanted him as much as he wanted me. For him and for the cameras of course.

I got up and wiggled my ass in front of him.

He caressed my right cheek then my left.

"So nice and smooth. So nice," he commented.

Then he pulled my butt plug out. I handed him some lube one of us had dropped on the table. He liberally applied some to my ass and to his shaft.

I placed my left hand back to lean on and showed my ass to my lover as I reached back with my right and grabbed his manhood.

I gasped as I lowered myself onto his cock.

I shuddered a bit inside as I knew that I was the one initiating. I was taking his cock in my ass and would be fucking myself with it.

He also gasped at the tightness of my hole.

I leaned on both of my arms as I pressed myself down on his cock.

All the way to his balls.

Jason let out a deeper moan.

I shifted my hands onto his knees and began riding up and down on his stiff cock.

My ass seemed so tight at first.

It was as if I could feel every nerve ending there.

It felt so alive.

I felt so in control.

Part of me liked that.

I angled myself so that my prostrate was stroked the most.

I breathed harder as I pleasured myself on his cock.

Part of me tried to deny that was what I was doing.

As I Ioosened up I began to ride him faster.

My caged penis bobbed up and down too.

Soon I was bouncing up and down on his thick rod.

"That feels so great Shauna," he said as he continued to moan loudly.

Part of me felt frantic all of a sudden.

I had hit the right spot.

I had to be fucked harder.

Faster.

I rode his cock more enthusiastically.

Part of me just had to.

I wondered if this was how Emma had felt riding Jon's cock the other day.

"Oh fuck that feels good," Jason exclaimed.

"Uh, huh," I muttered as I continued to ride his thick cock.

I felt it begin. A great feeling inside me.

"Uhhhhhnnnn!" I exclaimed as I felt a powerful anal orgasm overtake me.

I ground harder as I rode him.

The feeling continued.

"Thats so hot!" Jason exclaimed

Jason's cock began to pulse as he exploded in my ass.

I kept riding him for a bit but slowed down.

He wrapped his arms around me and I fell back onto his muscular chest.

Spent.

Thoroughly spent.

"That was amazing Shauna," Jason said as he kissed the side of my neck. "Simply amazing."

He cuddled me from behind again.

It felt good just sitting there. His semi-flaccid cock still buried in my ass while being held in his muscular arms.

We should get up and clean things up a bit Shauna, Jason said.

We soaked up the evidence of our carnal act from the couch. As much as we could that is, and got ourselves ready to head out.

Soon we were arriving at Denise's place. Perfect timing as I had just finished the breakfast Jason bought me at a drive-thru. I could see that Denise was waiting for me inside the entrance to her place. She waved when she saw us. I kissed my boyfriend as we said our goodbyes and went to meet my waiting girlfriend.

The oddness of that made me chuckle a bit. Only I could wind up in this situation.

After Denise greeted me with her own warm kisses, we went to her apartment. She seemed very bubbly today.

Denise closed the door and spun on the heels of her casual shoes to face me. Her light sundress twirled a bit with her joyous movement. She bubbled with enthusiasm and eagerly kissed me.

"I missed you so much," she said and kissed me some more.

I was surprised to see that the bodyguards were gone. I looked at where they usually sat with a quizzical look on my face.

"Oh, them. I let them go. I figured we would be spending the afternoon together again and it would be weird for them just to sit here," Denise stated joyously.

She took me by the hand and led me to the couch.

"I have so many ideas for what we could do together today!" Denise said enthusiastically.

"You sure seem happy today," I commented with a smile.

"Well it is the weekend you know buster," she began. "And yes I am happy. I am going to have you all to myself this afternoon. Whether we go out as girlfriends or as boyfriend and girlfriend, just being with you is all that matters," Denise said and placed her hand on my knee.

I looked down and saw her perfectly manicured, red nailed hand on my white stocking covered knee.

I had forgotten that I was still all done up as Shauna.

How could I forget that?

That bothered me. But it still could not dampen the mood Denise was putting me in.

I reached down and she took my hand in hers. I looked up at her and saw such a happy smile.

"You are so amazing. After all this, you can be filled with such joy. And I might add, your enthusiasm is so infectious! Who could be down around you?" I smiled as I spoke.

I realized I needed to do something to keep her happy. We both had been through so much and Denise more so recently.

"Tell me, what would we do if we went out as girls?" I asked my girlfriend. She needed something special for her and she seemed to want us to do that so much.

Oddly enough.

Maybe.

Just maybe I could do that.

For her of course.

"Really? Oh, I'm so excited!" My girlfriend stated as her face truly lit up. She seemed even more joyful.

"Well," I began.

"Oh we would go out to lunch at a trendy place for a change and all dressed up. Shopping. We would definitely go shopping. And-"

Ding!

It was my phone.

We both looked at it.

It was my wife Emma. She wanted me to call her as soon as I got a chance.

"Let me call Emma and get her ok. Then we can talk about 'Both' possible dates," I said feeling a bit overwhelmed at the thought of going out to eat and shop as Shauna.

In public.

During the day.

On a sunny Saturday.

"Ok, ok," Denise slumped back and curbed her enthusiasm a bit.

"Good morning Emma," I began into my phone. "I'm glad you texted me. I was going to call you soon anyways. I was thinking of spending the afternoon keeping Denise company and-"

"No, I'm sorry, that won't work dear. Jacques and his wife are coming over for dinner and to spend the evening with us. I want you to be with me and there is lots for you to do to get ready."

My jaw dropped open.


Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
30 Comments
AnonymousAnonymousover 1 year ago

It's such beautiful writing. It's obviously very erotic (and causes havoc in my panties) but I also love the sense of nuance and ambivalence you convey in Shauna's feelings about her emerging and shifting gender and sexual identities. Please keep writing!

Natasha xx

NaughtyOne88NaughtyOne88over 3 years agoAuthor
Ch 29 is away!

Ch 29 has been sent for posting.

Naughty

johsunjohsunover 3 years ago

I'm with one of the previous posters who said they hope that Shaun(a) and Emma get back together and get rid of Naughty.

God a feeling though that it isn't going to work out that way. I think Shaun as a normal guy is going to be long gone. Maybe he and Emma can get along with him 'en femme' and being pegged by Emma. I thought that the one scene so far was hot, even though S was really surprised. I would love another scene of them together like that where he gets into it from the first.

I still wonder if Emma is 'in' on the whole thing, or is just another victim. The idea that they are watched all the time, that N can listen in on their - or at least Shaun(a)'s - phone, and can track him and Emma, means that they have no privacy and no way to really talk. It would drive me insane, or at least drive me to some desperate measure.

And I'm still not sure that Denise isn't in with N as well.

NaughtyOne88NaughtyOne88over 3 years agoAuthor
Ch 29

Hopefully doing final edits tonight! Sorry to keep you all waiting! I hope to post it later tonight and then it goes to site approval which can take several days.

I will post once it is posted.

Naughty

AnonymousAnonymousover 3 years ago
Reference request

Hi fellow readers,

Shaun/a refers to Jacques as the boyfriend (lover) of Emma at the start of ch28 (among other places). Can anybody help me where this comes from? Where (chapter, page) is Jacques introduced as the _boyfriend_(lover) of Emma? He probably is but I can not find where this occurs in the story anymore ( most likely because I browsed to many times back and forth through the story...)

Hope one of you can help me out, thanks.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Better Life through Chastity A young man is forced into chastity by his loving girlfriend.in Transgender & Crossdressers
Mom's Big Black Hobby Ch. 01 Harvey comes home from college to surprise his mother.in Incest/Taboo
Last Friday: First Sissy Experience A couple has a night with sissy chastity and a black cock.in Transgender & Crossdressers
Humiliated Sissy Husband A wimp of a husband is forced to be a sissy by his wife.in Transgender & Crossdressers
Neighbourhood Terror to Sissy Pt. 01 A story about a neighbour who wants some payback.in NonConsent/Reluctance
More Stories