Ella Unleashed

A/N: This branch started with Isaac quitting the game that Emma had made for him and deliberately picking the option where she has sex with Trent. I viewed this as an option where Isaac admits that the darker elements of his cuckolding fantasy turn him on. This branch starts with ‘Ella Unleashed’ and will definitely delve much deeper into the darker aspects of the cuckold lifestyle. If this is not your cup of tea, you might be best served to stick with one of the other branches. You have been warned, I created this branch to give me a chance to get much more intense. Those looking for a sweet Emma should look elsewhere.

I sat up in bed in a panic, having just woken up in the middle of the night. Something was wrong. I looked around the room and noticed a dark figure by the side of the bed.

“What the …” I said, startled to have someone in my room in the middle of the night.

“Relax, Isaac,” I heard Emma’s voice say, “it’s just me.”

“Fuck,” I said, “you scared me, waking me up in the dark like that.”

She reached over and turned on the lamp on the nightstand next to my bed.

Shit!

She was a mess. Her hair was disheveled in the ****, her makeup was smeared, her skirt was askew, her blouse untucked with half the buttons undone. I could tell by the nipples poking out against the fabric that she was braless. And there was a very obvious smell of sex emanating from her.

She roughly pulled the sheet down off the bed.

“Lose the shorts,” she said to me, nodding in the direction of my boxer briefs. I saw the look in her eyes. It was best I not challenge her, unless I wanted things to end up even worse for me. This was Ella paying me a visit and she looked much hungrier than I had ever seen her.

I pulled my underwear off and tossed them onto the floor. I finally had a chance to glance at the clock on the nightstand. 2:36. She’d been with Trent for a very long time.

I looked at her clearly well-fucked look and felt myself getting very hard, very quickly. Ella noticed.

“You like seeing your girlfriend after she’s been repeatedly fucked by your friend, Isaac? I see that you’re getting hard just thinking about it.”

“Yes,” I said. There was no point trying to deny it. She already knew it was true. I had intentionally chosen to send her to my friend, and intentionally chosen a path where she would have sex with everyone in my D&D group before I was ever allowed to make love to Emma.

"So tell me what this makes you, Isaac," she insisted, "getting incredibly turned on knowing that your girlfriend just fucked one of your friends, and is coming to you to show you her well fucked pussy."

"A ..." I hesitated, "ummm..."

"Just admit it, Isaac," she said, "you've been hiding from your true nature for too long now. Let's just get to the truth, once and for all. The truth will set you free."

"It makes me a ... a ... cuckold."

"Mmmmm," she purred with a smile, "and more importantly, it makes you my cuckold. I am really going to enjoy cuckolding you, Isaac."

She reached into the drawer in my nightstand and pulled out the tube of KY I kept stashed in there, and handed it to me.

"I think you know what I want you to do," she said. "Stroke it while I tell you all about fucking your friend. Show me how much it turns you on to hear all about Trent fucking your girlfriend."

I began to stroke my rock hard erection, as she had asked, while she undid the three buttons of her blouse that were still done up and took off her shirt to show me her tits. Then she unzipped her skirt and let it fall to the floor so that she was naked right in front of me.

She climbed up onto the bed, standing so that she was straddling me, her feet on either side of my head, then she grabbed the headboard and squatted down, lowering her pussy down until it was right in front of my face. It was gaping open, having clearly been well and truly fucked.

"Look at this pussy, Isaac," she said to me. "The pussy you can't have. A pussy that has already been fucked by Mike and Trent, and that both Ben and Owen are going to fuck. Your friends are all going to plunder this pussy, Isaac, but you are not going to get it yet, and you know why? Because you are a cuckold, and we both know it. Mike knows it, Trent now knows it. Ben and Owen will both get to know it as well. You used to play D&D with these guys. You were the dungeon master, leading them and guiding them through quest after quest. And now they'll all know you're a cuckold and that they can fuck your girlfriend's sweet little pussy whenever they want."

"Oh god," I groaned.

"Yeah," she said, "you just love knowing that, don't you, Isaac. You just love stroking your cock, staring straight into a pussy that Trent just fucked, over and over again, don't you?"

I assumed the question was rhetorical. When I didn't answer, she got after me.

"Answer my question, Isaac."

"Yes," I said simply.

"Not good enough," she said. "Be more specific. Tell me exactly what you love about this, Isaac."

Oh god!

"I ... I love looking up and seeing your pussy gaping open like that," I said, "knowing full well that it is gaping open because Trent has just been fucking it."

"Very good, my deeply perverted little cuckold," she said. "There is something I need to tell you, Isaac."

"What's that?"

"I had assumed that Trent was a sweet, innocent little virgin. He is so shy and quiet. I couldn't imagine that someone so shy would have ever have even kissed a girl before. But Trent isn't sweet, and he isn't innocent, and he definitely isn't little, and he most certainly isn't a virgin."

"What do you mean?" I asked as I looked up, watching her slowly insert one of her fingers into her obviously stretched out pussy, right in front of my face.

"Well," she said, "let's start with the virgin part, shall we? Turns out there is a cougar in his neighborhood. He wouldn't tell me who, even though I probably wouldn't have known who it was anyway. But it's someone whose husband travels a lot and who found a rather unhealthy fascination for a certain attractive young man in her neighborhood. It means that Trent is anything but inexperienced. She has taught him quite well, as it turns out."

She slipped the finger that had just been inside of her into my mouth.

“I’ve had sex with a lot of boys. But they were all boys without a lot of real experience in pleasing a woman. They all knew how to fuck, but that was about all. Trent has had a woman teach him exactly how to give her pleasure. Damn, Isaac. It was good. The best I’ve ever had. He would have made me cum over and over again even without the excitement of knowing what it was doing to you. With that excitement, he turned me into a quivering mass of Jello. Fuck … it was good. Who would have expected that?”

She moved so that she was kneeling, straddling my chest, and she pressed her gaping, wet pussy down onto my chest and began to rub it along my body as she slowly moved it down across my chest and abdomen.

“The next point,” she said to me, “he wasn’t at all little, Isaac. He’s not as long as Grant, of course, but I’d say he’s a bit longer than Mike. Of course that makes him quite a bit longer than you.”

She reached behind her and flicked my shaft with her forefinger.

“Of course, it isn’t very hard to be quite a bit longer than you, is it Isaac?”

I groaned, partly because of the sharpness of the flick of her finger, but mostly because of the sharpness of her words.

“But what sets him apart,” she continued, “is his thickness. Grant is both long and thick, but even Grant isn’t nearly as thick as Trent. God, Trent stretched me out like I’ve never been stretched before. It was quite an amazing feeling, Isaac. I think I fell in love with thick cocks tonight.”

I moaned again at the thought of that.

“You like hearing that, Isaac? I’ve been with two of your friends. They are both bigger than you. Trent may just have the best cock I’ve ever had. And he damn sure knew how to use it. And his fingers. And his mouth. You suppose you’re the smallest of all four of your friends?”

“Oh god,” I moaned as she said that.

She laughed as I moaned at the implication that I was, at least in regards to size, inferior to all my friends. I knew that some of my motivation behind these fantasies stemmed from an inherent feeling of inferiority. It seemed only natural for her to want to be with other guys if I was, in some way or another, not quite good enough.

“You are the smallest of any of the guys I’ve ever been with,” she said with a smile as her pussy slid lower and lower across my abdomen. “So I kind of suspect you’ll be the smallest of all your friends, Isaac. Is that why you want me to fuck them? You know I’ll like their cocks better than yours?”

At this point she leaned her face down and kissed me, pushing her tongue into my mouth. I could taste something very familiar in her mouth. It was somewhat salty and reminded me a little of bleach. I knew exactly what it was. I was tasting Trent's cum in her mouth. She saw that I noticed that flavor.

"Oh yeah," she said, "that's definitely Trent's cum you're tasting. He loved feeding me his cum."

Her pussy had reached my turgid shaft, I could feel it's warmth and wetness pressing along it's length. Just as she made contact there, however, she began moving back upwards, keeping her body pressed closely against me. With her hands she guided my mouth to her body, and I kissed and licked her neck and chest as she slowly ascended. When my mouth got to the top of her tits, I once again began to taste that same familiar flavor.

"He also really loved cumming all over my tits, Isaac, especially when I told him I was going to let you taste him on me."

Once again I groaned at her words.

"That's right, Isaac," she went on, "Trent knows you're a cuckold. He knows you get off on the idea of him being with me, and that I love torturing you with it. He knows that I was going to come visit you, well fucked and let you taste the fact that he came on my tits and in my mouth. He knows that means I am going to fuck him again, and again, and that I am going to tell you all about it when I do. I suspect he isn't going to be squeamish like Mike. I think he is going to really like making you watch him fuck me."

I loved having my mouth on her perfect tits, even though they tasted of cum. I greedily devoured her nipples with my mouth causing her to moan yet again.

"You see, Isaac," she said, "that's the last part of my surprise with Trent tonight. He wasn't at all sweet and shy and innocent once he knew I intended to fuck him. Apparently his cougar loves to be dominated, so she taught him how to take control. It was completely unexpected. He was in charge from the moment I let him touch the insides of my thighs, far up under my skirt, letting him discover with his fingers that you had failed to bring me my panties. It was a side of him I had never experienced before, and I loved every second of it. He made me submit to him, forcing me to give myself completely to his desires."

She had shifted her position to where she was once again straddling my face, her pussy inches away from my mouth.

"That's right, Isaac," she said, "Trent gave me a fucking unlike anything I was expecting. He made me cum on his fingers, and then on his mouth, and then on his cock, multiple times. God it was fantastic. And he knows damn well I will let him have it again, so you better get used to tasting this well fucked pussy."

With that she lowered that gaping pussy right onto my mouth. It was incredibly easy to slip my tongue way up inside of her since she was still gaping open from the fucking Trent had given her. I moaned into her sex as I licked her, enjoying this very intimate contact with her most sensitive places, but just as I was getting into it, she climbed off of me and stood and started getting dressed.

"You may very well have created a monster, Isaac," she said as she sat down on my chair that she had pulled over close to the bed. She reached across and took my shaft into her hand and began stroking me. "Now cum for me. Cum all over yourself while you think about how many times Trent is going to get to fuck me."

And I did, almost instantly, groaning loudly as my cock twitched violently, emptying the contents of my balls all over my stomach.

"God I am going to have fun with you, Isaac," she said as she stood and walked out of the room.

Was I really ready for this unleashed version of Ella that I had created? I was definitely beginning to question the sanity of my actions.