The Benefits of a Girlfriend Ch. 08

"That would be cool," I replied. Figuring it was my turn to ask something, I thought for a moment and decided to go ahead with the question that was weighing heaviest on my mind. "So the thing with Mindy where she picked me. That was cool and all but it seemed a bit too coincidental. Did you arrange that with her beforehand?"

"Why don't you ask her?"

"I tried to. But she called me a loser and told me not to talk to her." I expected him to laugh at this.

"That's not cool. I'll have a chat with her about that. I can't expect her to respect you as a man, but she needs to respect you as a person."

He effectively dodged my question, but left me satisfied with his response, nevertheless.

After dinner, the guys decided to set up a beer pong tournament downstairs on the pool table. Fortunately, one of them had a tarp and thought to use it. Once I had cleaned up, I went downstairs to watch.

Mindy spotted me and walked over to me, "I'm sorry for what I said earlier when I called you a loser."

"It's okay," I smiled. "I am a loser, at least when it comes to sex."

"Right," she replied. "I didn't mean... I'm not sorry for calling you a loser. That's what you are. I'm sorry for telling you not to talk to me. That was just mean."

"Oh, okay," I nodded. "Thanks."

"So, Adam said you wanted to know if he told me to pick you as the only guy I didn't want to blow. And he told me to be completely honest with you. So, I will. I didn't know anything about you or Kristy or anything.

Adam and I are lab partners in biology. I've been obsessed with him from the first time I saw him. I figured a guy like that would never fuck me, but I thought there was a chance he'd let me give him head. So, I asked him a couple of weeks ago. At the time, he just said maybe later and I thought he was rejecting me.

Then, on Friday during class, Adam gave me this address. He told me if I showed up this afternoon willing to suck his friends' dicks, he'd let me suck his.

And, then you saw what happened from there. He didn't tell me anything about anything else before today."

"So, if he didn't tell you, how did you know to pick me?"

"I didn't know I was supposed to pick you. I just picked you."

"That seems incredibly coincidental."

"No, not a coincidence. The others guys are all at least kind of hot. You're not."

"So what? I'm the ugliest guy here?"

"I didn't say that. I said you're not hot."

"Isn't that the same thing?"

"Not at all," she laughed. "Ugliness refers to your face. There are people who are both ugly and hot. There are also people who aren't ugly and aren't hot, like you. Hotness is a combination of things, not just one thing. It's the total package."

"What specific things do you notice about a guy when deciding whether or not he's hot?"

"It depends on the guy. What, do you want to know how your score or something? How I evaluated you? Why I picked you."

I nodded eagerly, "I do."

"Do you really want me to say mean things? I can't be honest and hold back at the same time. Wait, do you get some twisted pleasure from girls putting you down?"

I sighed, "I do. I'm sorry. I don't want to creep you out."

"It's okay. If you like it, then I won't hold back. I'd rather turn you on by telling you what I think of you than giving you a bj or something. That's for sure. It's weird, but it's also kind of fun.

So, the first thing I see when I look at you is the hair or, actually, the spot where hair used to be. That's the characteristic that identifies you and makes you stand out. There are some sexy bald guys out there, but that look doesn't help you. Not at your age.

I couldn't believe it when Adam told me you just turned 20! I had you somewhere between a 35-year-old with a baby face and a 25-year-old who went bald early.

So, right away, I figured you were either a middle-aged loser trying to hang out with college kids or you were a loser in his mid-twenties with less than the best genes.

Then I saw the way you carry yourself. The way you stand. The way you looked at me. I could instantly tell you had no self-confidence. And if you're not confident, girls can tell. When you know you're a loser, you give off a loser vibe to warn girls that you're a loser.

And then I think there's something about your scent. Not that I can smell you. But, like pheromones or something. When I first stood near you, my pussy clamped shut and I could feel it getting dry. It's happening again right now as we speak.

And last, I've always had good gaydar. I know when a guy plays for the other team. That's my team. And I love hanging out with all of my teammates. I consider myself a bit of a fag hag."

"I'm not gay," I objected.

"Call it what you like, but I could tell you're meant to swing for the softball team. I know for a fact you don't bat for the baseball team."

"What are you talking about? I never played baseball or softball."

"It's a euphemism. Softball teams are usually made up of girls and girls usually fuck boys. So, if you swing for the softball team, that means you fuck boys.

Baseball teams are usually made up of boys and boys usually fuck girls. So, if you bat for the baseball team, that means you fuck girls.

I can understand why you would be confused, though. Maybe I should say you catch for the softball team, 'cause you don't use YOUR bat to fuck boys or girls."

"I'm going to use my bat to fuck Kristy's butt tonight," I retorted irritated.

"Oh really? You never get head. You never fuck pussy. But, you're going to fuck a butt." She rolled her eyes, "Sounds totally straight to me."

Adam interjected, "Hey Mindy, wanna be on my beer pong team."

"Sure!" she changed the of her voice to something far softer and far sweeter than she used on me.

"You guys have fun," I said. "And thank you so much for your honesty, Mindy. It means the world to me."

She laughed, "No problem. Anytime."

When Mindy left with Adam, I thought about her analogy and realized that lately, I had actually been playing catcher for Kristy's bat. It amused me to think of how Mindy would react to knowing about Kristy pegging me.

About a half hour later, Kristy came down all cheery-eyed and announced, "Michael, I have great news!"

Somebody turned off the music, and everything quieted to a hush.

With her as a center of attention, Kristy proceeded, "First off, Violet is coming back tonight. She has a show at 8:00 but said she should be able to make it here by 10: 00. She won't be dancing or anything.

She liked seeing me blow-banged so much that she was disappointed that she had to miss my pussy gangbang. So, she doesn't want to miss what happens with my butt.

The other thing really isn't news. It's more like a very special secret surprise. Do you remember when I originally agreed to let you take my anal virginity? You remember how I said yours would be the only prick I let inside my butt for a month or so until my hole was trained enough to take Adam's cock?"

I nodded.

"Well, after that I did some research and even experimented by taking someone else's anal virginity. And I found out that if you do it right, take it slowly, and use plenty of lube, it doesn't take that long at all to stretch out a butthole.

I now know for a fact that you can take a virgin anus from being able to accommodate a finger to a prick your size to a cock the size of Adam's all in the same day. I realized several weeks ago that there's no need to waste a month or even a week training my hole with your prick.

But I kept that secret because I wanted to save it for today. You know, like a present. So I'm happy to finally reveal that tonight will be your first and LAST opportunity to feel my butthole with your prick. Isn't that a wonderful gift?"

All I could do was glare at her with my eyes glazed with a mix of sadness, anger, and resentment. It was especially hard knowing I was the one she "experimented" on. And I thought if I hadn't been such a sissy, eagerly receiving the Adam-sized dildo when she pegged me with it, the original plan would still be in effect.

"I thought you'd like it, but I didn't know you'd be speechless," she giggled and patted my head. "And I've got even more good news for you. After you've had a chance with my butt, the rest of the guys from smallest to biggest are going to also get a chance to fuck my butt.

Then, just as I did with my mouth and pussy, I will give Adam exclusive rights to my butt. And he'll take me bareback to celebrate. Aren't you excited to have your useless prick permanently cut off from all forms of penetration much earlier than we had originally planned?"

My facial expression didn't change so she placed her hands on my shoulders and stared into my eyes. "Even though you love it, I know being a cuckold is hard. But, we both know it's what you were born for. And you're really good at it. You are without a doubt the best cuckold a girl could have. I love you."

When she followed this by pulling me in for a passionate French kiss, I couldn't stay upset with her. I had agreed to all of this whether I liked each individual thing or not.

Around nine, Kristy and I went into the bathroom. She put on a pair of gloves and removed my chastity device. Then I worshipped her ass with my tongue. After about ten minutes, she had me load her up with an enema. Surprisingly, even after nearly two days without food, it still required three flushings to completely empty her out.

I worshipped her hole again once she was cleaned out. And as I did, I noticed that no matter what I did or thought, I couldn't even begin to get hard. As my limpness persisted, it started to worry me.

Violet showed up with cupcakes and a "special" cake just for me. Then, Kristy and I went back to the bathroom for one more flushing.

I knelt down in the middle of the main room and Kristy bent over in front of me so her ass was in my face. I started to stroke myself while licking and gently probing Kristy's ass with my finger. When I realized my prick still wasn't working, I leaned up and whispered in her ear, "He's sleeping and won't wake up. Will you hurt me?"

She turned around and stood over me looking down at me smugly.

"Michael," she started. "Didn't you love being denied a lap dance by Violet and then watching all the real men playing with her tits?

Don't you love knowing that each of these men has a big yummy cock worthy of a blow job from your girlfriend, while every girl on Earth knows your nasty little prick will never be worthy of head?

Didn't you love being rejected by Mindy and then watching her suck every other cock here?

Don't you love knowing that each of these men has a big tasty ballsack full of hot delicious cream that your girlfriend loves to taste on her tongue, while your tiny little sissy marbles only produce rancid scum that no girl will go near?

Don't you love knowing that each of their rock-hard man-sized cocks got to fuck my pussy on YOUR birthday, while your limp little pussyfree pee-pee only got to watch?

Don't you love knowing that the feminine energy from the yin around your neck, the sissy tube around your weak little prick, and the hair loss pills I asked you to take have all made you completely impotent, just like I had hoped?"

After seeing the smirk on her face and the glint in her eyes, I closed my eyes and bowed my head. Then I shook my head as I realized this had been her plan all along.

"Michael," she continued, "Don't worry. Your inability to get it up hasn't disappointed me one bit. It's done the opposite. In fact, I want you to always be limp in sexual situations.

Staying soft lets a woman know that you know and your little peen knows what she knows. Your prick is unfit for penetration. It's not as big as a man's penis and it doesn't function like a man's penis.

Your prick is supposed to bow when in the presence of a woman, but especially when there's a superior cock standing proud and ready to service her."

Just then, Yori stepped forward and she took his semi-erect cock into her mouth. I watched her lips intently hoping this denial might cause some sign of life down below.

Then after he was rock hard, she withdrew his cock from her mouth, and announced to the room, "Okay, since my boyfriend has proven he's not man enough to get it up, to take my anal virginity, I'm going to need all the REAL men in the room to help me truly and permanently put him in his place as the asskisser we all know him to be."

Violet walked over and handed me a sheet of paper.

I read it to myself:

Thank you all for your generous contributions to Kristy's birthday present of making me her forever sexless witting cuckold.

In the past, each of you fucked Kristy properly before we started dating. Her having those experiences for comparison significantly decreased my sexual value before she ever saw me naked.

Today, you all received a birthday lap dance from Violet, a birthday blowjob from Kristy, birthday head from Mindy, and birthday sex from Kristy's pussy. And you've all already had at least two satisfying ejaculations as a result.

I, on the other hand, have never had a lap dance, never gotten a blowjob, never experienced even a moment of head, and am pussyfree. I haven't ejaculated in three months and if Kristy's plan to keep me impotent succeeds, I may never ejaculate again.

Despite my perpetual sexual frustration and the pain and humiliation it brings, I would not trade places with any one of you. While each of you deserves far better than the life of a wittol, I don't personally possess the mental or physical prerequisites to live the life of a man.

As such, I respect and admire each and every one of you. And I will forever be grateful for everything you all have done to make this day and my relationship with Kristy possible.

I now invite you, as better men than I could ever hope to be, to usurp me once more and collectively take Kristy's anal virginity.

Before each of you enter Kristy's butt I will ask your individual permission to show my appreciation to you and to demonstrate my inferiority to you by kissing your superior ass.

After I finished reading, I looked at Kristy. "Stand up and read it out loud," she ordered.

I hesitated dreading the idea of kissing even one guy's ass, especially in front of a roomful of people. I knew that would make things awkward at work and school.

"Do you disagree with anything written there?" she asked agitatedly.

I thought it over. If I did disagree with these statements, I would be disagreeing with her. I would be insulting all the thought and planning she put into this day. I would be rejecting the cuckold life she had envisioned for me. And, I would be humiliating her in a roomful of people. She didn't consent to that. I did.

So I stood up and prefaced the speech with, "Although I did not write the words I am about to read, I fully agree with all of them..."

As I spoke I noticed Yori and Kristy making out. Then both Mindy and Violet undressed and stood on either side of Kristy. They rubbed Yori's arms, shoulders, chest, back, and ass while he kissed Kristy.

Then he massaged all three of their breasts and sucked each nipple. Mindy and Violet leaned in and returned the favor sucking both of his nipples at the same time.

Then they both dropped to their knees and took turns sucking his cock and his balls.

Nobody was watching me as I read the speech. I wasn't sure if they were even listening. But I enjoyed reading it even more as I assumed that every male in the room would be treated to a two-girl oral threesome. I just chalked that up as another in a long list of pleasurable sexual experiences I wasn't worthy to receive.

After I finished reading, Kristy bent over in front of Yori, propping herself up with a chair. Mindy and Violet took my upper arms and guided me to the spot just behind Yori. Then, in unison, they pressed down on my shoulders guiding me to my knees. Again, in unison, they instructed, "Thank him."

Nervously, I fumbled my words, "Thank you Yori for being better than me and doing all the fun sex stuff. Can I kiss your ass to say thanks?"

Yori and all three ladies laughed before he answered, "You can smooch my cheeks like you did Violet's and Mindy's. None of that French kissing stuff you did with Kristy's. I don't swing that way."

Mindy giggled and lightly slapped my back. I figured she was once again making assumptions about my sexuality. And that was a little irritating because I had no interest in "swinging that way" either. A quick peck on each cheek was bad enough.

"Scooch back a little," Violet instructed me after I had proven I was an equal opportunity ass kisser. I slid back so I was about a yard away from him. Then Violet whispered in my ear, "Kristy wants you to stay in this position the rest of the night. Since you're not man enough to fuck her butthole, she doesn't want you watching her hole being fucked. Instead, you can watch the ass of the man doing the fucking."

Mindy leaned in and whispered in the other ear, "The boys get to watch from the baseball team's bench. You get to watch from the softball team's bench. Enjoy the view!"

I watched Yori's ass more jealous of what his eyes were seeing than what his cock was feeling. He went slowly at first easing his dick into her delicious hole. Then I watched his ass flex as he gradually picked up speed until he was rapidly pounding her butt. Once I heard them both moaning, he didn't last long.

Then, Yori switched places with Tony who was stripped naked and getting fluffed by Mindy and Violet. Mindy carefully removed Yori's condom and placed it on the end table next to her. Then she cleaned his cock with her mouth.

Tony was now positioned with his ass just inches from my face. I thanked him using similar words to what I said to Yori and then kissed his ass cheeks. Tony stepped forward and took his turn ramming Kristy's hole.

When it was Adam's turn and after I "thanked him", Kristy offered him exclusive rights to her anus. And just as he had done for her mouth and her pussy, he made a rule excluding me from ever penetrating that hole.

After Adam came inside her, Mindy held up a single serving container with angel food cake and said, "This is Mike's birthday cake. As you can see, it doesn't have any icing on it. But we're going to fix that."

She placed the cake on the floor between Kristy's legs. Kristy squatted over it and coaxed globs of Adam's jizz out of her ass and onto the cake as she mocked, "Michael, you might have thought getting a piece of ass would be a piece of cake. But instead, your piece of cake is going to taste like a piece of ass."

That caused a good amount of laughter.

Then Adam proclaimed, "I am so glad I'm not a cuck. If any of you are like me and you don't want to see what's about to happen, you can join me for some beer pong."

Brett disagreed, "I don't know about the rest of you, but I dig those challenge videos where people have to eat gross stuff. Sure, it's nasty, but it entertains and amuses me."

Mindy held up the cake, "You think it's nasty now? I still have a lot more icing to do."

"I know," laughed Brett as he pointed at the condom-covered end table, "It's going to be so gross!"

Yori, Chuck, Sam, Dave, Marco, Jermaine, Melvin, and Brett stuck around. Tony, Anwar, Todd, and Adam went downstairs.

Mindy finished icing the cake with the contents of the eleven condoms sitting on the end table. Then, Kristy placed a candle on it and everyone sang happy birthday.

I had gotten used to the unpleasant taste of cum, but consuming it mixed with lube and poured over a piece of spongy cake almost made me vomit.

A couple of the guys watching also gagged.

The other guys and the three ladies watching me struggle just laughed.

When I finished, Mindy yelled, "See. I knew you played softball."