Chelsea Ch. 04

Story Info
Danny breaks up with Amanda.
2.7k words
4.62
33.4k
51
6
Story does not have any tags

Part 4 of the 5 part series

Updated 06/08/2023
Created 09/02/2016
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

Well, I decided to keep this going and I set it up for a 5th chapter too. Hopefully I'll have the next one out a lot faster this time around. If anyone is wondering about "Wild Devil" it will continue, but I've hit a bit of writers block with it...so it might be a while before you see the next chapter. I hope you enjoy this one though and look forward to chapter 5.

*

The next morning, I left Chelsea's house at around ten o'clock and walked the thirty minutes to my house. I could have taken the bus, but I needed the time to myself; I needed to clear my head.

I was about to call Amanda and officially put an end, to our relationship. It's not that I was having second thoughts or anything like that, I just didn't want to fight with her.

Unfortunately, I knew that this conversation would inevitably turn into another argument. I was trying to enjoy the few minutes of peace that I had, before I got home and called her. When I arrived at my house, I locked myself in my room and sat at the computer for a few minutes, tapping my foot on the floor anxiously; this is it, I thought to myself. I have to do this...it's for the best.

I called Amanda and raised the phone to my ear, listening as it rang three times before I heard her voice on the other end.

"Hello?"

"Hey," I said immediately. "What's up?"

"Nothing...."

I sighed, cleared my throat and forced myself to talk.

"Listen, we need to talk."

"Yeah, I guess we do."

We began our conversation, discussing everything that had happened with Amanda and her boss. She told me that it had been him, who made the first move and that he had been sexually harassing her for a while before it happened. Finally, the son of a bitch apparently threatened to fire her, unless she did whatever he wanted.

In a sense, I couldn't exactly blame her for everything that she had done, now that I was aware of that...on the other hand, she also admitted that she had enjoyed herself when she was with this guy. So with that in mind, there was no forgiving her; but there was no forgiving me, either.

We both agreed that since we had cheated on each other, and that it had happened more then once for each of us...it was best if we ended the relationship; a mutual agreement. That was a good thing and I was honestly surprised, that we weren't arguing.

There was one thing that Amanda demanded to know though, refusing to end the conversation, until I gave her an answer.

"Who did you sleep with?"

I really did not want to get into that with her, but she was persistent and had no intentions of letting the subject drop. I figured she did deserve to know, who was I to keep it from her after she had confessed everything to me.

"You don't know her," I said finally.

"I met her not too long ago, at one of those concerts down in the park. We hung out after the concert was over and it just...happened."

"Oh my god," Amanda replied, after a moment.

"Are you talking about that crossdresser?"

How the fuck did she...

"W-What?"

"Chris told me about her...or him...that he was hitting on you at the concert and that you all thought it was funny. You slept with him?"

Chris, if you remember, was one of my friends who had been with us the night that I first met Chelsea. I hadn't spoken to him since that night, actually. I was mildly annoyed with him now though, after finding out that he had told Amanda what went down that night; at least he hadn't told her I went home with Chelsea. Not that it mattered, now that she knew anyway.

"First of all," I said, my voice becoming a little aggressive.

"Chelsea is not a crossdresser; she's a transsexual. It's a woman as far as I'm concerned, so please...don't be so disrespectful."

"Wow," she said, with a bit of a laugh. "Look at you, defending her and all. You're into her or something, aren't you?"

"Yes! I wasn't at first, but...it just...I don't know."

There was silence on the other end of the line now and I sighed, rubbing my forehead for a moment.

"I'm gonna hang up now," I said finally. "I'm glad we could do this in a civilized manner and come to a mutual agreement."

"Me too," Amanda agreed. "I really am sorry for what I did."

"I know you are; and so am I, believe me. I never meant to do anything like that to you."

We said our goodbyes and hung up and I was relieved, to finally be done with this situation. I hooked my phone up to it's charger and decided it was time for a shower. The hot water soothed my muscles, and I leaned my head back and tried to relax a little. The events of the last two days played through my mind, over and over again, throughout the course of the day.

Around the middle of the day, Allie came downstairs to talk to me. I told her that I had slept with Chelsea again the night before and she didn't appear quite as surprised, as I thought she would. I told her that I had broken up with Amanda, to which she seemed satisfied.

"Clearly, you two weren't meant to be together," Allie said, trying to comfort me.

"You're so much better off, without her in your life."

"I know," I agreed. "We had a mutual understanding. I just wish that it hadn't ended on such bad terms."

"I can understand that. It was fucked up for her to cheat on you...with her boss of all fucking people. But I'm proud of you, because you acknowledged that you fucked up too."

"You know I'm the kind of guy who owns up to his mistakes."

"So, what happens next? With you and Chelsea, I mean..."

I decided not to use the exact words that Chelsea had used last night, since I knew my sister would just get a kick out of it and start making fun of me; couldn't let her know that I was now somebodies "bitch."

"I guess...we're together."

"Seriously?"

"Yeah," I laughed. Crazy, I know."

"So you're totally cool, with the fact that she's got a dick?"

I shrugged my shoulders and nodded my head. Allie laughed and gave me a pat on my back. "Well, as long as you're happy little brother. Although, there's still the fact that she's like half your age."

"So? Age is just a number, you know that."

Allie laughed and agreed with me, giving me her blessing and that was the end of our conversation on the matter. Just after Allie left my room, I heard what sounded like a motorcycle out front of our house. It got louder and louder, until I was pretty much positive, that it was parked right in front of the house.

I stepped out into my backyard and walked around the side of the house, opening up the gate and was surprised to find Chelsea. Sure enough, she was parked right alongside the building with a motorcycle. She smiled up at me as she got off the bike and removed her helmet, before stepping onto the front lawn.

"What the hell are you doing here?" I asked, surprised to see her.

"Just thought I'd drop by," she said, stepping up in front of me.

"I wanted to see how things went with Amanda."

"How did you know my address though?"

"I told you, my brother is in a biker gang; he knows people, who know people."

That bit made me a bit uneasy, but I laughed it off and Chelsea pulled me into her arms for a hug and a kiss on the lips. We stepped into the backyard and sat down at the patio table, as I begun telling her about what happened earlier with Amanda. We shared a few beers together, as we discussed everything.

"So, it's definitely over now?" She asked.

"Officially."

"Good," she grinned. "Now you're all mine."

"Oh, is that so?" I winked at her and Chelsea laughed.

"Why don't you come over here, and sit on mamma's lap."

I looked around nervously, and up at my parents bedroom window that overlooked the backyard. I didn't particularly want my neighbors...or my parents, for that matter...to see me sitting on some ladies lap.

"What's wrong," she asked. "Feeling shy, all of a sudden?"

"What? No, I'm fine."

I stood up, walked around the table and sat down in her lap, as she had requested. Chelsea smiled, taking a drag of her cigarette and blowing the smoke out. She put the cigarette out and pulled me closer to her, pressing her lips against mine and sliding her tongue into my mouth. I could feel her cock poking at my ass...she was hard as a rock already.

"Why don't we go inside," I suggested, with a grin.

"And what happens when we get in there?"

"You'll just have to come in and find out..."

I stood again and started walking towards the back door. Chelsea stood up and followed me, stepping into my room behind me and I shut the door and locked it. She looked around at everything in my room and smiled.

"Nice place," she complimented.

"Make yourself at home."

Chelsea took that to heart apparently. As I turned away from the back door, after locking it up, I found her already stripping out of her clothes. I couldn't help but laugh as she pulled her shirt over her head and threw it to the floor, revealing that she had been wearing no bra. She followed with her pants and then laid down in my bed, now wearing nothing but her panties.

"Comfortable?"

"Very much," she replied. "Why don't you join me?"

I pulled my shirt over my head, removing my shorts and climbing into bed with Chelsea.

We laid beside each other and she leaned in, kissing me on the lips again. As we started making out, my cock immediately rose to full attention; so did Chelsea's.

"So, what exactly happens now that we're in here?" She asked.

I kissed her again and slid my hand into her panties, wrapping my fingers around her cock and started stroking. Chelsea moaned as I worked her cock, still happily making out with her as I did. I moved on to her lap again and leaned forward, resuming our make out session, only now I was dry humping her at the same time.

I could feel her cock poking my ass through my boxers and god, I wanted it so badly. We stopped kissing and I moved down, sucking on her tits for a moment, as I slid her panties down her legs and removed them for her.

With her cock out in the open now, I started kissing my way down her well toned tummy. I passed her waist line and started licking the tip of her cock.

My tongue swirled around the head for a few moments, teasing her and Chelsea groaned.

"You fucking tease," she said softly, to which I laughed.

I slowly moved my tongue from the back of the head, all the way down the length of her shaft, until I reached her balls. At that point, I wrapped my fingers around her cock again and started sucking on her balls and stroking her at the same time.

Suddenly, the power shifted between the two of us.

Chelsea was having no more of this teasing. She grabbed me by the arms and pulled me forward, sliding out from underneath of me and throwing me onto my back. Sitting on my chest, she smiled down at me and grabbed her cock with one hand and started slapping me in the face with it.

"You want this cock, you little slut?"

"Mm, fuck yeah."

"Tell Mamma, you want her big fat cock in your mouth."

"Please mamma...I want your cock!"

She slid forward and shoved her dick right between my lips and into my throat. I gagged, jumping a little and squirming around underneath of her for a few seconds.

My gag reflex eased up and I was able to take her thick member, without any further trouble. Chelsea grabbed my head with both hands and proceeded to start fucking my mouth. I could feel her warm balls, pressing against my chin and my eyes were watering and spit leaking out of the corners of my mouth as she skull fucked me.

"Oh god...Danny...I'm gonna cum..."

Not even a split second after she said that, she pulled her cock from my mouth and began jerking it furiously. I gasped for air and laid there, staring up at her as she stroked herself right in front of me. Then, that one eyed monster swelled up and erupted like a volcano, spraying a very impressive amount of cum all over my face.

Three shots landed on my lips, and I stuck my tongue out to taste the delicious cum. The next two shots fell upon the bridge of my nose. I barely managed to close my eyes in time, as the final shot splashed across my left eye and almost blinded me. I could feel her shaking on top of me and hear her panting, as she slowly started coming back down again.

"That was so good," she sighed, still slowly stroking her cock.

"You really got me good," I laughed.

"What...the...fuck?"

We both jumped in surprise, Chelsea rolling off of my chest and I grabbed the blankets, using them to wipe the cum from my face so that I could open my eyes. There, standing in the doorway of my room, was none other then Allie. She looked absolutely stunned at what she had just seen, her eyes wide with total shock.

"Holy...fuck!"

Great, I thought to myself in embarrassment. My big sister had just watched me get sprayed in the face with cum; this was probably the most humiliating moment of my fucking life.

"I...um..."

"I was going to say dinner is ready," Allie said softly. "But...I'll just...leave you two alone?"

Without another word, she stepped back and pulled the door shut with her. We heard Allie charging up the stairs from the basement and I sighed, falling back against the mattress.

"God damn it," I groaned.

"Well, she sure got a shock there."

"No shit," I laughed.

"I guess it's a good thing, she already knows that you and I have been fucking. She just didn't expect to walk in on it."

"She'll survive."

We laughed about it after a few moments, before getting out of bed and cleaning up some. I would have loved to have fooled around some more, but Chelsea had to get going. We got dressed and I walked her back outside to her bike.

"By the way," she said, reaching for her helmet.

"My brother is having a cook out at his place next weekend...you interested in coming with me?"

"Yeah, sounds like fun to me!"

"Great," she smiled. "Bring your sister too; maybe we'll find a nice biker guy for her to hang out with."

We exchanged a brief kiss, before she put on her helmet, mounted her bike and drove off down the street.

Once her bike was out of sight, I turned and made my way back towards the house. I found Allie sitting out front on the step, smoking a cigarette and smiling up at me, sarcastically.

"Don't say a word," I said, as I sat down beside her.

"Oh...I'm not saying anything...though next time, you might want to remember to lock your bedroom door before you give your girlfriend a blowjob; man that sounds strange."

She chuckled and I blushed furiously, burying my face in my hands and sighing.

"I'm never going to live this down, am I?"

"Probably not."

"Sometimes, I wish I were the older sibling."

"I know," Allie laughed, offering me a cigarette.

Fortunately, my sister said nothing else for the remainder of the night, regarding what she had walked in on. I was relieved that she didn't seem as interested in making fun of me, as she said she was originally.

I wondered where exactly life would take me next, as far as things between me and Chelsea were concerned.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
6 Comments
smoothed273smoothed27312 months ago

🥰🥰🥰💖💖💖💋💋💋✌

AnonymousAnonymousover 4 years ago
so hot

his sister walking in on them

GrrrreatImaginationGrrrreatImaginationover 5 years ago
Hot! but now....

I giggle all the time when I see all those wild-assed commas. I read someone's comment on another story...I giggle just thinking about it...they said you should just rip the comma key off your keyboard, lol! Ever since then, I can't help noticing that you really do go nuts with commas.

Seriously hot story series. I was glad that you ditched the blackmail angle. It let us like both of them... you kinda did the same thing with him and Amanda. Kind of a quirky happy ending that way.

Anyway, I've liked a bunch of your stories over the years. Thanks for sharing it all with us.

barbarosanybarbarosanyabout 7 years ago
Take your time -- we can wait!

I read your note on the biography page - and wanted to tell you that you should definitely let Wild Devil sit till you're ready to work on it again. It's a great start and I'm eager to find out what happens next, but you're right to let it sit and 'stew' until it's ready to serve. Thanks for all your stories, man! Looking forward to seeing where you go with this new version of "CHELSEA."

addyftwaddyftwabout 7 years ago
Just Your Average Wisky Story...

...so it deserves 5 stars. All your stories are amazing! Keep up the awesomeness!

Show More
Share this Story

READ MORE OF THIS SERIES

Chelsea Ch. 03 Previous Part
Chelsea Series Info

Similar Stories

"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
"What Does She See in Him?" Ch. 02 After being away for weeks, Laura rewards Andy.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
The Wedding He needed a date to his sister's wedding.in Transgender & Crossdressers
More Stories