John to Jane, Becoming a Bi Cuck

Chapter 1

I had just turned 24, and life was going great with my fiancé, Stephanie, a 23 year old blonde so stunning she should be a model instead of a teacher. She was 5'8" with huge, perky tits and a huge ass, and legs for miles. I, on the other hand am a little on the slight side. I'm 5'6" and skinny.

We were happily engaged, and set to be married in less than a year when things started to get awkward one afternoon.

"Babe, I was thinking a lot of our wedding and our future life together, and I think there's something we should talk about," Stephanie said nervously after a long sip of coffee.

"Uhhh, sure, yeah, what's up?," I responded. We had been through plenty of pre-marriage jitters and I thought this would another simple non-issue.

"We have sex a lot, and I do enjoy it..." she began then paused for a moment. "But, I've only ever been with you, and I've never actually orgasmed from sex before...and, well...I'm afraid that once we get married I'll never have the chance to, and I don't want to go my whole life without orgasming from a cock...." She quickly said the last bit, clearly nervous about how I would respond.

"I, uh...I'm not sure I understand. I thought our sex was great...what exactly are you getting at?" I slowly said, shaking slightly as I was beginning to have guesses as to what she wanted.

She brushed her hair off her face, slowly looked up to meet my eyes, and said "I just want to be fucked by a massive dick for once. Just one time! Then we can get married and go on with our lives and I'll know that I haven't missed out on anything."

I slowly looked down at the table, let out a big sigh, and excused myself, telling Stephanie I needed to think about things.

I went into the bathroom, sat down on the toilet, and just sat there in silence for about 15 minutes. My thoughts we're all over the place and I was beginning to panic when she knocked at the door.

"John, I'll be in the bedroom waiting for you when you're ready to talk again...

Then, after another 30 or so minutes I got up and walked to the bedroom to find my fiancé putting on makeup, and dressed in a short, black leather skirt and crop top.

"I am going to go out this evening, John. I am going to go out, and I want to be fucked after. I can go out alone, and live my life, and get what I need so we can move on. Or...you can come with me, and we'll do the same thing we do every Friday night, followed by lackluster missionary sex where you cum in minutes and I masturbate afterward....it's up to you, but just know that I would prefer you give me your blessing to go out alone." She said as she applied her lipstick, a bright red.

Feeling defeated, I said "Fine. Just go. Do what you want, but just know that I may or may not be here when you get back. I'm also going to have to think about this and process it."

She jumped to her feet, ran over to me and gave me a big hug, pressing her tots into me. "Thank you! Thank you! I promise I only love you and could only ever love you, and I can't wait to see you tonight, and marry you and live my life with you, thank you!" She excitedly shouted.

The next hour was a blur. I poured myself a drink, turned on the football game, and got comfy, just trying to forget about things. Around halftime, Stephanie walked out of bedroom looking like an absolute dime. She came over, kissed my cheek, whispered that she loved me and then walked out the front door, leaving me all alone to think.

Chapter 2

I hardly slept that night. Thoughts of my beautiful fiancé being railed by a stranger from a bar kept me up nervous until around 4am.

I finally awoke around 10am, and rolled over to see the other half of the bed empty, so I walked to the kitchen to make myself a coffee.

Around noon I heard the front door open, and looked over to see Stephanie walking in, but she wasn't alone. Behind her was a hulk of a man. A tall, muscular, handsome, chiseled man followed her in.

"Good morning John. Before you say anything, just listen. This is Jemarcus. We had a great night together, and afterwards he had an idea that could really help our marriage."

I took a breath and opened my mouth to talk and she cut me off. "No, wait. Please. He fucked me so much better than you ever have, and he thought that maybe, just maybe, he could show you how to pleasure me the way that I need to be pleasured. You'll never have a cock as big as his, but he may be able to show you how to make me orgasm. Isn't that something you want to learn to do?"

"No way!" I shouted. "No way do I want to have another man show me how to fuck my fiancé. That's humiliating!"

Then Jemarcus spoke up. "John, look, the humiliating part is already over. I brought your wife to orgasm 4 times last night. If you can't learn to do that, she'll only crave other men more than she already does. It's in your best interest to figure this out."

"Fine. Whatever. Fuck this! This can't get any worse!!" I shouted at Jemarcus, then I turned to Stephanie. "Fine. Have him show me, but this is the last straw. If this goes bad, I don't know if I'll be able to stay with you..."

Just like the previous night, she jumped up, hugging me and thanking me, then slowly led me back to the bedroom, followed by Jemarcus.

When we got there, Stephanie directed me to sit in the chair, and Jemarcus patted me on the shoulder and said "take lots of mental notes, little man," as he pushed Stephanie down onto her knees.

Licking her lips, Stephanie reached out her hands excitedly and pulled out the biggest dick I had ever seen. The rumors about black ducks being bigger were clearly true. Jemarcus' cock was 7 inches, and still growing.

Without any hesitation, Stephanie let out a quick, soft giggle then engulfed the massive cock in her mouth. Bobbing up and down with a ferocity that I had never seen from her before. She seemed entirely entranced.

I started to look away, and Jemarcus reached over, grabbing my shoulder and shouted "Watch, you fucking sissy! Watch me fuck your woman, and pray you can learn to do the same! If you take your eyes off her again, you'll regret it!"

A shiver ran up my spine, after being threatened by this man, and I once again turned to watch Stephanie swallow his cock.

After a few minutes of this, he directed her to stand, and he shoved her down, face first onto the bed and ripped off her skirt. He wasted no time at all, pushing his entire, full 9 inches into her puffy pussy, as the love of my life let out a moan unlike anything I'd ever heard from her before.

"Yeeeeeesss Jemarcus! Oh my god, fuck me!"

"Wait! Jemarcus, you don't have a condom on!" I shouted in a panic.

The words were barely out of my mouth, when the back of Jemarcus' hand smacked me in the face, knocking me off the chair and onto the ground.

"This will be my fifth load in your woman. This won't make any difference after the first four, now shut the fuck up and watch, you fucking sissy!" He shouted at me. Tears welled in my eyes, as I looked up from the ground at Stephanie, my fiancé, the love of my life, my high school sweetheart, being impaled by a 9 inch black cock.

I got back in my seat just as he flipped her over onto her back.

"Now stand up, sissy! Stand up and come over here.

Not wanting to be smacked again, I walked over and stood over my moaning fiancé.

"Get to the side of her and start eating her out. Do it while I fuck her. Learn that multiple spots must be pleasured at once. Do it now, and don't make me ask again!"

I moved onto the bed, and as I climbed up I was, for the first time, aware of how horny I was. I was as horny as I had ever been, and despite the situation, was excited to eat my fiancé's pussy.

I quickly got in position and began to pleasure her, and only after around 30 seconds realized that I was only inches away from another man's cock. I had never seen another man's cock in person before, let alone been this close to one.

As I was thinking about that, Stephanie began to scream and convulse. "Oh my

God! Yes! Yes!" She screamed, as she shook so hard that both Jemarcus and I had to adjust ourselves. While adjusting, his cock slipped out, smacking me in the face, which I assumed to be an accident, before he once again impaled her.

Right in the middle of Stephanie's seemingly endless orgasm, Jemarcus shouted "oh yeah, I'm gonna cum!" And he shot the biggest load I had ever seen deep inside her pussy. There was so much there that it slid back out like a waterfall as her pussy throbbed from the orgasm.

"Oh yeah...ohhhh yeah, that's how it's done!" Jemarcus exclaimed. "I hope you took notes, you fucking sissy cuck."

Without a word, I walked out of the room. To say that my life would never be the same would be an understatement.

Chapter 3

Three weeks had passed, and I'd watched Jemarcus fuck Stephanie at least once a day, and sometimes three times a day. After the first week, he said it would better if he moved in, so that he could teach me more. It was humiliating at first, but it quickly became routine.

I would wake up, and, at Jemarcus's request, would make coffee for all three of us before watching him ravage my fiancé.

After the end of the third week, Stephanie announced that she would need to go on a business trip, but that she would be back in 3 days, and that Jemarcus would be in charge while she was gone. I thought it was very weird that she would go out of her way to say that he was in charge, and also weird that he would still stay here, but whatever. At least I didn't have to watch her get fucked by him for a few days.

She left, and immediately he turned to me, a wicked look in his eyes.

"John, I think you've done fine at the first part of your training. You have watched plenty. However, to truly understand how to pleasure a woman, you need to walk a mile in her shoes. Put these on." He said as he handed me a pair of Stephanie's high heels.

"Uh, sure. Fucking weirdo. Walking around in heels won't teach me anything, but at least you're not fucking Stephanie today."

I put on the shoes, and even though they fit perfectly, due to my small size, they were very difficult to walk around in.

Around 2pm I was starting to get the hang of it, when Jemarcus walked into the room with me and handed me a skirt, panties and crop top.

"Go in the bathroom, shave every inch of your body and put these on." He said firmly.

"Man, come on, don't be ridiculous, this isn't going to teach me anyth-" I began, when he swiftly kicked me right in the crotch, forcing me onto my knees.

"Shave. Put these on. Then meet me in the bedroom and I'll show you more about pleasuring Stephanie. Do it now, or you'll regret it." He said, then stepped back to watch my reaction.

I stood up, tears streaming down my face in pain, snatched the clothes from him and stormed away to the bathroom.

After slowly shaving my body, I was amazed at how nice the smooth skin felt. It was even better than feeling Stephanie's freshly shaven skin. Then, if I thought that was great, slipping into Stephanie underwear, skirt and shirt was miles better. Why weren't men's clothes this soft and comfortable?

After getting fully dressed, I looked in the mirror and saw a short girl looking back at me. A girl who looked nervous, but also kind of cute.

I left the bathroom and walked to the bedroom to see Jemarcus laying on the bed in his underwear.

"Come stand in front of me, sissy," he demanded of me.

After weeks of humiliation, I didn't even hesitate. I stood in front of Jemarcus immediately.

"Now turn around and bend over. Let me see your ass." I did so, slowly.

"Oh, yeah. Good stuff," he said as he came to stand behind me, playing his hands on my thighs, sending a shiver up my spine. "Now this is an ass I can work with."

"Now, bend over on the bed."

I did so, and he came behind me slowly ran his hands up the back of my thighs, lifting my skirt.

"Good. Now, I'm going to show you what it feels like to be a woman. Then you'll truly know how to please Stephanie and I."

Woah, I thought...Stephanie and him? Why would I need to learn to pleasure him, too? Show me what it feels like to be a woman?

"Jemarcus, I'm sorry, but this is too much. I need to go," I said as I started to stand up, but he grabbed the back of my neck, pushing me face first onto the bed, causing me to stumble in my heels. Then SMACK!

SMACK! SMACK! SMACK!

Jemarcus repeatedly spanked me, causing me to yelp in pain.

"Please, please stop!" I begged.

SMACK! SMACK!

I began to sob.

"Please! I'll do anything, please just stop!"

There was a pause, and I didn't hear anything. Then, my skirt was pulled down, and panties pulled to the side, as something cold was poured onto my ass crack.

I sobbed as he slowly pushed a finger, then two, then three into my ass. It was some of the worst pain I've ever felt.

Then, to my surprise, it started to feel good. I began to push back against him, and after a minute of that, despite my efforts, a small moan escaped my lips.

"Good. You're ready," he said firmly.

I heard his pants fall to the ground behind me, and felt the tip of his enormous cock on my ass.

"This will only hurt at first, but then you will love it, just like Stephanie does." He said.

There was another pause, then he plunged his cock deep into me, causing me to scream in pain. I thought he had gone all the way in at first, but to my surprise he kept going deeper, and deeper, and deeper, filling my insides with his warm, thick cock.

He began to push in and out, and as he grew harder, so did I. Pressed against the the bed, my small dick rubbed into the blanket in rhythm with his thrusts.

"Oh, yeah! You're so tight! Much tighter than Stephanie!" He shouted in between grunts.

I could feel everything. Everything pulse of his cock with his heartbeat. His firm hand pressed into the back of my head, then pulling at my hair. His other hand, form on my right ass cheek. His balls slapping against mine. My small dick, rubbing, and rubbing, and rubbing against the bed. His cock pressing into my prostate over and over.

"I'm gonna cum in you now, you fucking sissy. I'm gonna cum in you then you'll be mine forever." He slowly muttered, a few words at a time in between thrusts.

"Beg for it!!" He shouted out of nowhere.

"What?" I asked, after a few seconds. It was hard to speak with all the sensations.

"Beg for it! Beg me to cum in you!"

"Please, please come in me, Jemarcus!"

What was I saying!? This had gone too far, but I couldn't stop now. If this felt half as good as the rest of the sex, he was right. I needed it. I needed to beg for it.

"Please!! Please fill me!" I moaned back.

"Beg me, and call me master, or you'll never get it!" He shouted, as he spanked me, driving me and my hard, small cock further into the bed.

"Please, master, I'm begging you! Please cum in me!" I shouted desperately. I needed it! I needed it so badly.

Then, pulling my hair harder than before, bending me backwards he thrusted deep into me, groaning and moaning as he released what felt like a gallon of cum, filling me to the brim.

The excitement was too much. Feeling the cum fill me up, I blew my load all over the bed.

I laid there for a moment, then he rolled me over.

"Clean me up. Now."

Caught up in the ecstasy of the biggest organs of my life, I didn't hesitate. I licked and slurped his massive cock until it was sparkling clean.

"Good. Now, smile for the camera, sissy," he laughed as he pointed to the bedroom door where I saw Stephanie standing, rubbing her pussy and pointing a video camera at me.

"What? No, I...you can't just film people like that?? What the hell, Stephanie?" I asked, confused.

Walking over to me, Stephanie said "don't worry Jane, that is what we'll be calling you now...this is going to be a good life for you. Especially with this video for blackmail. I don't think Jemarcus and I will have to worry about anything, and you'll get to pleasure us whenever we want. Wow, this is going to be great, isn't it Jemarcus?" Stephanie said with huge smile on her face.

"Oh yeah it is. Now, Stephanie, help Jane cleaned up. She'll be needing more practice tonight."

To be continued...