The Bet

Chapter 1

What on earth was Charles thinking? I was only giving him some good-hearted teasing, and then he challenged me with this bet. And the result seems to be pretty obvious. No offense to Charles, but there is no way he could win. There had to be some trick, and Charles was always the clever one. And the worst part is, there is no walking back from this. Some statements or challenges cannot be undone. And given the nature of the bet, it would inevitably change the way they looked at one another.

I remember how we first met, when I rescued him from that bully in front of the school. That was our first year of high school. I remember diving in just because it wasn't right for a guy to pound on someone nearly half his size. Yet, truth be told, winning that fight didn't hurt my reputation.

Yet more importantly, Charles had become my best friend. And it was unlikely I could have made it through high school without all the help I received from him.

And now that we were attending the same college, we have kept up our friendship. I have a room at the dorm, but Charles managed to get a small basement apartment off campus. His place was a bit of a dump, but I still envied him his independence.

I got an idea of how he may be using his independence last weekend. I had just popped by to ask if he wanted to join some friends at the bar to watch the game. And while I was waiting for him to change, I found some porn with shemales and crossdressers on his computer.

I couldn't resist kidding him. "I think you would look hot in lingerie... Would you like to have a real man's cock inside you? ... I bet you jerk off, thinking about giving a blowjob."

He was flustered and embarrassed, his face beet red. He denied everything of course, but that simply encouraged me to tease him more.

I wasn't serious any way. He could watch whatever porn he liked. Lord knows I've watched my share, including shemale porn, and I thought the shemale in his video was hot.

"You don't think I'm a real man?" He asked in what seemed to be an accusatory tone.

I was still kidding around since I had never thought of him this way. "I just want to know, when you watch these. Do you imagine yourself on your knees wearing lingerie? Or are you the man getting a blow job?"

He was starting to calm down, and had a serious tone. "So you think a real man deserves to be serviced by a femboi?"

I wasn't nearly as serious, laughing as I responded. "Well... yeah."

"So if I can show you that I'm a better man than you. Will you give me a blowjob?"

"Huh. What are you talking about. There is no way I'm doing that." I was now startled by how serious he seemed to be.

"Afraid that you're not a real man?"

"Hell no."

"So you'll agree to a challenge. The one who proves to be more manly, gets his cock sucked by the loser."

This was proving to be one of those childish dares that one doesn't back out of because they don't want to look weak. "No offense Charles, but if the criteria is manliness, than I'm going to win. You're still a virgin, and have hardly dated anyone. How can you claim to be more of a man than me?"

"So, if you're the real man, you expect to get your cock sucked."

"Damn right."

"In that case, how should we measure who is the real man? I've got more money than you. Or I could challenge you to any academic test you would like."

"Please," I responded dismissively. "We both know you're smarter than me. Yet there are plenty of smart girls. That hardly makes you a better man. It should be a test of strength, like a wrestling match, or a race. Something like that."

"Something we both know you would win."

I could only shrug. He was right, but how else could I show my manly strength?

We both paused for a moment. I still have trouble believing what he suggested next.

"Well we can decide it based on what defines us as men. We can measure our dicks."

I laughed at first. Then I realized he was serious. "So you want us to just whip our dicks out and measure ourselves."

"Not tonight. We should allow some time to get hard, and for the winner to enjoy a nice blowjob. But essentially, yes."

We agreed to have the bet on Friday evening, back here at Charles place. And then we proceeded to meet up with the other guys at the bar. It was difficult to pretend as if it was a regular Saturday evening, but neither of us said a word about this once we left his apartment. In fact, the whole week was rather strange.

I have been dreading what game Charles is trying to play, giving himself a week to prepare. Sure there are those pumps and other devices which claim to increase penis size. Yet how much can be done in a week, and how much can it really accomplish? Not to brag, but I'm quite confident in my penis size. The anticipation was driving me crazy.

Over the course of the week, I found myself occasionally glancing at Charles crotch area trying to gauge the size of his cock. There was no noticeable bulge which would suggest he was packing a cock disproportionately large for his body size. Occasionally I would find him doing the same thing, and he would only smile. The whole thing was freaking me out. What was he up to?

The only thing I knew for certain was that I didn't ever want to suck a cock. Yet I refused to back out of this bet.

And now hear I am arriving at Charles place, Friday evening at the appointed hour. I knock on the door.

Chapter 2

An attractive woman answered the door. This didn't make any sense. It was a small basement apartment, so there would generally be no one else here. And Charles didn't have any sisters, or any close female friends which might explain a woman being in his apartment.

"Come in Dave," she said politely, and directed me to the sofa.

She really looked hot, but also familiar. I was already on edge before I knocked on the door, so perhaps I wasn't thinking straight. The one part of me that did know what it wanted was my cock. Seeing this beautiful young woman in a sexy dress, heels, and her makeup done up nice for an evening out, my cock responded instinctively and was straining against my pants. Perhaps this was for the best as I wanted to be fully erect for the bet. Yet it was embarrassing at this moment.

She offered me a beer, which I declined, and then sat next to me on the sofa. Her hand rested on my thigh and she looked me in the eyes. "You're trying to figure out what's going on, aren't you?"

I would have preferred to respond in a cool collected manner, but I simply nodded.

"It's me Charles."

It took me a moment to register what she was saying. How could she be Charles? I was scrutinizing her carefully her face and her body. And she remained still allowing me to check her out. And staring at that face, and in particular those eyes, I accepted the truth.

"Wow, I wouldn't have recognized you if you didn't say anything. You look so... uhm... hot." Was it appropriate to call your buddy hot? Under the circumstances, I didn't know how else to describe him. Charles was a hot chick.

"Thank you, I can't tell you how much that means to me." She had a coquettish smile. Yes, I was still thinking of the person next to me as 'she', even though I knew it was Charles .

Sensing no resistance, she leaned in and kissed me passionately.

I welcomed it, especially as her body leaned into mine. Her hand on my thigh moved up to my crotch, and was stroking my cock through my jeans.

She sat back and looked into my eyes while continuing to rub my cock through the jeans. It was so hard it was becoming uncomfortable to keep it in my pants.

"So, you like the new me." It was a statement and a question.

My bulging hard-on had already answered. I simply had to answer truthfully. "Hell yes!"

She then knelt down in front of me. "It seems to me, that I owe you a blowjob."

I didn't quite know what she was referring to, but who would object to receiving a blowjob.

Sensing my confusion, she elaborated. "Our bet. I think we have established who the real man is in our relationship. Or would you like to make it official by measuring?"

"Yeah... right, the bet. Can you explain what that was all about?"

"Well honey." She was undoing my belt, and unzipping my fly as she spoke. "...there was never any doubt who was going to win this bet."

She now had my dick in her hand and was gently stroking it. "I have seen your cock before. In the showers, or simply the bulge in your underwear as you changed. In fact, I have had to be careful not to be caught staring at it. Trust me, there is no comparison between yours and my small penis."

"Then why enter a bet you would lose?"

"Because there is no loser here. I have fantasized about sucking your cock for so long, that this makes me the winner." She paused to lick the tip of my cock.

"And I didn't plan this. But I wanted to show that you are an alpha male, and that you have the right to demand servicing from me, and to fuck me. Having sex with me will in no way diminish your masculinity. It will reinforce it."

I now understood everything. Charles had wanted a relationship for some time, but was afraid I would reject him because it was gay.

I simply smiled, assuring Charles that everything was good between us. "So I can fuck you as well Charlotte?"

"Charlotte?..." she considered the name and shrugged. "Yeah, I like it." Then leaned forward and kissed me. And in a sultry voice responded, "And yes, you can fuck me."

She then lowered her head, and took my cock into her mouth. She almost managed to take all of me at once, but her gag reflex stopped her initially. She was using saliva to lubricate my cock, and her tongue was rubbing along the bottom of my penis. It was truly amazing the way she was taking me nearly all the way in and still using her tongue to lick along the length of my cock. I couldn't help moaning, which encouraged her to go further.

She was determined to take me all the way in. And with a few more strokes of her lips bobbing up and down on my member, she achieved success. She managed to get past her gag reflex and fully take me deep into her throat. I couldn't believe it when I felt her lips touching my balls. No girl had ever managed to deep throat me. And the contractions of her throat as she struggled to keep me buried deep within her was amazing. All I could do was lean back and moan with delight.

I have never cum from a blowjob. It was always great foreplay for the fucking to come. Yet for the first time, I believe I was getting close. Yet as I watched her kneeling before me with her head buried in my lap, I really got to fantasizing about her body. And in particular that ass. Oh man, I really wanted to pound that ass.

Mind you, that aroused me further, bringing me closer to the edge of climax. I placed my hand gently against her chin, and directed her to stop. "OK, that's good baby."

She was clearly disappointed. "Did I do something wrong?"

"No baby, not at all. That was the most amazing blowjob I've ever had." I patted her head affectionately. "Yet now I really want to try out that ass of yours. Let's go to the bed."

She giggled with delight, and practically skipped to what passed for a bedroom in this studio apartment.

Standing next to the bed, she embraced me and leaned in for a kiss. We continued kissing as I reached up to unfasten her dress. She continued to kiss me passionately as I slipped her dress straps over her shoulder. Her skin was so soft and smooth, it was enticing simply to run my hand along her body.

The dress was past both her shoulders, and she lowered her arms to allow it to fall to the ground. She was now embracing me, bodies pressed together, wearing only a matching bra and panties. It felt so good to just hold her and feel her soft skin against me.

My pants were still undone, so a gentle unzip of my fly and a push dropped them to the floor. She was then unbuttoning my shirt. Button by button, Charlotte moved her delicate hand down my chest.

She released herself from the kiss, and gently took my shirt off. And she was clearly admiring my body for a moment as I stood completely naked.

We began kissing once more. Yet this time she began lo lower herself, kissing bit by bit down my chest. Her hands caressed me as she proceeded downward until she was grabbing my ass.

Something was retrieved from a side drawer. It was apparently a condom which she placed on me with a gentle touch.

Charlotte once again took my cock into her mouth. I simply stood there enjoying Charlotte's skilled felatio.

Yet it did not take long for my arousal to near its peak once more. Once more, I put a stop to it by pulling back.

She looked at me with the cutest puppy dog eyes, silently begging for her treat.

I ran my fingers through her hair. "Don't worry sweetie, you will taste my cum in due time. But right now, I want that ass."

She lay back and lifted up her backside. Our hands met at the hem of her panties, but she promptly put her hands to the side. This allowed me to take off her panties with one slow but steady pull. I decided to leave the padded bra on to help maintain Charlotte's femininity.

With my erect penis now between Charlotte's naked thighs, I decided to place my cock next to hers.

With an amused smile I said, "It's official, with a puny dick like this you are definitely no man." His dick was not even half the size of mine. Even hard, it was embarrassingly small. "Women want to have a real man's dick inside of them."

Charlotte only nodded, wanting that real dick inside of her.

"Turn over baby, and give me that ass."

Instantly Charlotte turned over and was on all fours with her ass raised, and legs spread.

I knelt on the bed behind her and began to run my hand along that ass. Such a perfect tight ass. How did I never notice Charles had such a nice ass? I should have been pounding this years ago.

Charlotte arched her head back to kiss me. "I prepared myself earlier, so I'm ready for you."

"You prepared yourself, huh." I imagined Charlotte thrusting her fingers into that ass, and lubing herself up. All for something that could have been simply me walking out the door immediately. I'm glad I didn't.

"I have fantasized about this for so long." She was practically moaning in anticipation.

I placed the head of my cock against her buttonhole, and then gently pushed. It yielded.

My cock entered a few inches, then I paused, and then all the way in. Charlotte groaned. It has hard to tell if it was a groan of pain or pleasure, maybe both.

For me, it was all pleasure. Her ass muscles gripped my cock, and the tightness allowed me to simply enjoy holding my cock buried deep inside.

After a moment to settle, I began slow but deliberate thrusts. Her whimpering and gasps enticed me to thrust even harder.

Only once before has a girl allowed me to take her up the ass. I loved it then, even if she didn't. But now, this was a whole new level. I could fuck this ass forever.

My pace was increasing with every thrust. I was now pounding into that tight ass with reckless abandon.

Whatever pain Charlotte may have felt had disappeared. She was now crying out with pure lust. "Oh yes, fuck me! Fuck me! Harder! Oh God yess!" When she wasn't crying out, she was moaning. One could only imagine what the neighbours upstairs were thinking, if they were home.

I grabbed her hair and pulled back. The benefit and mystery of Charles growing out his hair was only now apparent.

"That's it, take it bitch," I growled in her ear.

I grabbed her hips and increased my intensity once more. Her whimpering, cries, and gasps had become one long moan of desire. "Ohhhhh Goooood Yessss!"

Her little penis shot its load onto the bed. And I couldn't help laughing with glee as my bitch boi came from being fucked in the ass, and his/her penis was never even touched.

The excitement built into my thrusts, and my body started to tense up. Holding Charlotte's thighs tightly, I buried my cock deep inside her.

I groaned heavily and then shot my load, rutting inside her.

Charlotte bore my weight as I collapsed onto her. My dick was still in her ass, and I left it there while my erection dissipated. Charlotte lay there content in my arms, and her ass was still warm and comfortable.

We were both remaining still so we could catch our breathes.

I then slowly pulled out, and rolled off to my side. I was staring at that beautiful body, so smooth and glistening with sweat before me.

I placed my hand on her back, and gently caressed her. "That was amazing. I can't believe we never did that before."

Charlotte smiled. Her hair was a mess, and she was lost in the moment. She leaned over and kissed me. "Thank you for making me a woman."

I simply returned the kiss. Truer words were never spoken. While Charlotte had lost her virginity, as either a man or a woman, there was much more to that statement.

I could no longer look at Charles the same way again. And it was clear that Charlotte and I were just beginning what I hope will be a long and intimate relationship.

THE END