The Hole Ch. 01-03

"Oh, I don't know about that," I said, denying what was obvious but too embarrassing to admit.

She got that devilish look in her eyes. "Really wimp? You don't like it when I tell you you have a fucking tiny little penis? You don't get turned on when I tell you it's the size of my pinky?" She reached down and grabbed my hardening dick, and she smiled. "Exactly what I thought."

I couldn't deny it any longer. What else was I to do but ask the obvious? "So now what?"

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Before I tell you what happened next, I think it's important I give more context. After all, another thing He has taught us is the paradox of truth: "The search for absolute truth is imperative, and it is also impossible." This means that our human minds can only try to wrap themselves around all that is both outside and inside of ourselves, but we are severely limited.

How did I get here? Whatever answer I give is only going to include a small sliver of my experiences, and therefore a tiny iota of the right answer. The right answer is everything that has ever happened. That's how we all end up where we end up.

But we don't have time for that, and while my duty is to give you the history of my place in The Cult, I regret I can only give you a facsimile rather than the real thing. I'm limited by time, by language, and by my own mind.

I'll admit, much of what I'm about to say is already in the recorded History from my first Interview. Nonetheless, I feel I owe this chapter of History a bit more context for those without the time to listen to every Interview, at least so this written chapter of History makes sense.

For starters, I'm an American male, born and raised in a typical suburb, playing and watching sports with my dad. Therefore I have the same hangups many guys do. I'm not tall enough. I'm not strong enough. I'm not tough enough. Etc.

Add to this, that beyond our sports bond, my father was never any good at things men are "supposed" to be good at. He couldn't fix anything or build anything. He wasn't good with his hands, so he never taught me any such things, and I definitely inherited this gene.

None of this ever bothered me on a visceral or conscious level. It was all just insecurities rippling through me. It was until I dated Lauren in college that it all came roaring up to the fore.

Lauren represented everything I wanted in a girl. She was feminine in voice and body, but she was that cool girl who could hang with the boys. She wasn't the hottest girl in our friend group, but she looked really good in a t shirt and jeans, and I loved her long curly brown locks. Best of all, she liked to write poetry and so did I. We decided to take a poetry class together, and we spent a lot of time sharing. In the process we got close, and eventually we hooked up.

Before we knew it, our sophomore year was over, and we were an item. That summer we decided to rent a little place near campus with two of my guy friends and one of her girl friends. It wasn't long before things started to unravel.

It started when we decided to go for a drive up the coast. We got in her car, a Mercedes her dad had gifted her. We stopped for gas and she asked me to fill it up while she went in to get some water. I put regular in without thinking. It required premium. When she came out and realized what I'd done she went ballistic. Lauren had a temper. She asked me what kind of a man puts the wrong gas in a car?

The rest of the day was spent getting towed and hanging out while the mechanic fixed it. When we showed up there and he came out to ask what the problem was, she said, and I quote, "My idiot boyfriend put regular in a Mercedes." The guy looked at me and raised his eyebrows. I think he felt sorry for me. Anyway, I swear she flirted with him the rest of the time we were there, and I just sat there moping. It was a rough day.

We got past that and things were good again, for about two weeks. That's when she bought a bike rack for her car and asked me to put it on. I didn't want to let on that I had no idea how, and I figured with focus I could follow the directions and get it done. About two incredibly frustrating hours later I came in and admitted I just couldn't figure it out. I know, it's pathetic, she didn't need to tell me. But she did anyway. "Fucking pathetic."

That's all she said before going upstairs and asking Will, my friend and roommate since freshman year, if he could do it. I think he felt bad for me, but he said no problem. He and Lauren went out there while I stayed inside and watched out the window. Fifteen minutes later he was done and she gave him a huge hug and kiss on the cheek.

We were having sex pretty much daily that summer, but I noticed after these two incidents, we didn't for at least a week. I chalked it up to fighting. I gave her shit for giving me shit both times, and I made her apologize for saying shitty things to me. Eventually she did, and we started sleeping together again.

But then the third incident happened. About three weeks later her father and brother came to the house to visit. It was the first time I met them, and I could tell it was important to Lauren that I made a good impression on them. "They've very provincial, masculine types, so please try to up your game," she warned me.

They showed up and we greeted them in the driveway. Two big guys looking very similar got out of the Mustang, one just looking about twenty years older than the other. I walked up to them resolutely, looked them in the eye and shook their hands. Immediately I noticed Lauren became cold with me. I didn't know the issue, but I wasn't going to pursue it then and there.

We all went out for lunch, and I held my own by keeping the discussion focused on sports, something I know quite well. Lauren's mood seemed to brighten. After this, they dropped me off and took her to town. When they returned to drop her off, I came out to say goodbye to them. I told them it was great to meet them and I shook their hands again. I thought I'd done a good job. But when they pulled away and I turned to Lauren, she was walking in a huff inside the house.

She went to the bedroom and didn't want to let me in. Finally she did and I asked her what the hell was wrong. In anger she shouted, "You shake hands like a fucking pussy. They have no respect for you."

This started a fight. I told her if that's how they judge a person then I don't give a shit what they think. She told me my lack of masculinity didn't end outside of the bedroom. Then she told me she's disgusted by me and there's no way she'd ever let me inside her again. Suffice to say, that was that.

Or so I thought. We still both lived in that house for the summer, but we barely spoke, and it was awkward for everyone else. Everyone except Will apparently. Yup, you guessed it. They were secretly fucking, apparently ever since he'd put that rack on her car. He told me this the next school year and apologized profusely. We remained friends and Lauren found a new friend group.

She made quite an impression on me though. She was my second girlfriend and the second one to cheat on me. Two for two. A huge blow to my male ego that I've never really overcome. It didn't help that having been roommates I'd seen Will's dick and of course it was twice the size of mine.

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The other thing you'll need to know is that I was madly in love with Abby. I still am. I've always been a romantic. I've had huge crushes on random girls since I was probably ten years old. I'd see a beautiful girl and project my dreams onto her. Rarely did I ever work up the courage to talk to these girls, even if they were in my school, and so they remained fantasies. I just desperately wanted to be in love.

Then I had girlfriends. I idealized both of them. For the first few months I thought Jane and Lauren were the perfect girls, everything I'd ever dreamed of. Then reality hit and it hit hard. It didn't stop me from dreaming though. So after college I dated and dated, and other than one that lasted about four months but never really felt like "The One" for either of us, I met Abby and just about lost my mind for her.

Yes, then reality set in, and we had all of the problems in bed, but other than that, we remained strong. We always made each other laugh. We enjoyed similar things, like going for hikes and watching classic movies. We made good food together. It was pretty much everything I'd hoped for, and her looks and sex appeal were beyond what I'd ever hoped for. She was "The One" for me, at least until I realized that notion was a silly one to begin with.

This is all to say, that for the many months when sex wasn't regular I felt incredibly anxious. I simply can't escape the fact that as a man I believe deep down that it is my duty to keep my girl sexually pleased, to fully satiate her appetite, to give her regular orgasms, etc.

To not only not do so, but to have her eventually tell me this directly tapped into my deepest insecurities. This is not to mention the energy it took to try to dominate Abby. It was an act, and acting takes a lot out of you. Pretending is difficult. So I was feeling tired and disconnected, guilty and anxious nearly all the time. I was convinced she'd leave me if I didn't up my game, and I just couldn't let this one slip away. I was willing to do whatever I had to do to be sure she wanted to stay.

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And that brings us back to our conversation.

"So now what?" I asked.

"Now we stop pretending you can be something you're not," she replied.

"But where does that leave us, sex wise?"

"Well, we're just going to have to reverse roles."

"But I thought you need someone to dominate you."

"I do, but I think I think I have both sides to me. I don't know why, but I do enjoy humiliating you."

"But what about your other need?"

"I don't know. Let's not worry about that. Let's just enjoy these roles, ok?"

"Ok. Yes, ma'am."

"Good boy."

And we both laughed and then went out for breakfast.

-----

I wish I could say we both fell easily into these roles and our problems were solved. Of course it wasn't so easy. This was entirely my fault. Abby seemed completely at ease switching from kind, caring girlfriend outside of the bedroom, to wicked princess inside of it. I, on the other hand, went back and forth from getting rock hard whenever she gave me that look of hers, to feeling like a loser of a man right after I'd cum.

For the rest of the day I'd fret that she was going to leave more for a better man, mostly to myself, but sometimes out loud. I couldn't help it. I only now know, with His wisdom, that this is how I'm wired. It's difficult for almost any man to overcome his belief that he needs to be the Alpha in his woman's life, and this is a sad thing considering most men simply don't have it in them to ever assume that role.

Lucky for me, Abby no longer needed to be turned on by my masculinity, so I was able to admit my fears of her leaving without turning her off. "Sure, I find it repulsive," she once said with my hard dick held between two fingers, "but what else is to be expected from a little worm of a man after all?"

Abby had never enjoyed having her pussy eaten. She chalked it up to some shame from her upbringing. But since I was no longer even attempting to give her orgasms with my penis, she started sitting on my face and grinding to get herself off. She'd do this while filing her nails, or while scrolling through her phone. It was amazing for me. She tasted so good, and admittedly I'd always been pretty good at cunnilingus. I guess it's like unathletic basketball players becoming great at shooting three pointers.

Between this and the handjobs she'd always end up giving me to finish me off, things were going pretty well. About once every two weeks she'd even let me inside of her, saying we needed that to stay connected, and we'd make out while doing so. I know it wasn't mind blowing sex, but it felt good, and we both seemed happy.

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But then I'd get insecure again and again. I'd say that while I was horny the harsh things she'd say were amazing, but afterwards I thought she thought I was less of a man. She'd tell me that it was all play, and it had nothing to do with how much of a man I was. She'd calm me down by telling me I'm more of a man for being vulnerable enough to let her say such things and to be turned on by it, that I was an amazing boyfriend, and that she'd never leave me.

Yet, of course eventually she did start to get tired of having to console me, and the intervals between our sexual experiences started to grow again. This only made things worse, and it all came to a head when I caught her fingering herself while watching another James Deen video. I accused her of being secretive, and she had to hide this side of her for fear that it'd set me off on another tailspin. I realized she was right, and I told her I'm sorry I can't dominate her, and I'm sorry I'm so insecure, and I'm so afraid to lose her. That last one broke through, and she held me until we fell asleep.

-----

I wish I could say we talked the next morning and got things all sorted out. What happened next was simply beyond our control. We woke up the next morning and Abby shrieked when she looked at her phone. It was a text from her sister, from whom she hadn't heard for years. "Call me right away," it said. "It's about dad."

Abby's father had died of a heart attack. She was devastated. It was made much worse by the fact that she was expressly told by her mother, via her sister, that she was not to come to the funeral because after all, it was her fault her father died of a broken heart. Some crazy shit, but some real shit nonetheless.

For the next week, Abby's therapist made plenty of time for her. The rest of the time her friend Heather and I consoled her and tried to keep her calm. The whole time she'd be very quiet and then she'd get angry and sad and she'd cry hysterically. About a week later the crying stopped, and she said she didn't want to talk about any of it any more ever. So we let her be, and she returned to work and so did I.

This was a mistake. It was quiet, but a rage was boiling inside of her. I should have known. She seemed different. Distant. Emotionless. She spent most of her time in the bedroom with the blinds and the door closed. She started drinking more. We'd always enjoyed a glass of wine after dinner together, but she was now drinking at least a bottle if not more, often alone. We didn't have any sex during this time, and I didn't even bring it up for fear of causing more trouble.

This whole thing had me really upset, but I was holding it all in too. I didn't know what to do, and my anxiety was higher than ever. I started having the feeling she was going to leave at any minute, and I started to look for signs when I could. I became obsessed with worry, and I started canceling my tutoring appointments, and suddenly I couldn't really afford my half of the rent.

This pissed Abby off, but she barely said a word. At least until I came home one day and found her in the bedroom so I could tell her my asshole boss just fired me.

"I don't blame him," she said. "You're useless anyway."

"What the fuck, Abby?"

"You're useless. You're not even a man. That's just the truth. Sorry."

"Jesus, Abby. That's so fucking hurtful."

"What can I say? The truth hurts."

Before I said anything horrible to her I walked out of the room and slammed the door. I slept on the couch that night.

-----

In the morning I woke up and remembered our fight. I wished it was a bad dream, but of course it wasn't. That was verified when she walked over to me on the couch and laid on top of me. She looked me in the eyes and told me how sorry she was, and that hurt people hurt people. I asked her if she meant what she'd said. She told me, "Of course not, but we are definitely in trouble. We need help. We really need help." I said I agreed.

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Chapter Two

I won't bore you with too many of the details of the back and forth over the next two weeks or so, but I'll give you a summary. In essence, we were now both in a deep hole. Abby was still reeling from the death of her father and her exile. I felt terribly for her, but also angry, and I indeed felt useless without a job or any money to contribute. We both felt sad about our relationship.

We knew we still loved each other, but we admitted that our sexual incompatibility could make us more friends than romantic partners. We were truly lost, totally vulnerable, like we were floating in space, holding hands that were slowly slipping away. In other words, our defenses were down, and both of us were open to pretty much anything that could save us.

In the middle of that Abby brought up the idea of non monogamy. Admittedly I'd always only thought that was for weirdos, but when she explained what her therapist had told her it actually made sense. She told me it's insane that we expect our partners to fulfill every need, and that with openness and trust it was possible to get certain needs met outside of the relationship, and that this not only wouldn't harm the primary relationship, but it would actually strengthen it.

Up until this point of my life I would have likely rejected the idea out of hand, but in my state I was open. There was just one problem, I told Abby. I didn't want to fuck anyone else. Then she proceeded to tell me her therapist said there are all kinds of arrangements, and that ours could be a version of what she called cuckolding.

"So let me get this right," I said with only a hint of sarcasm. "You'll be fucking other guys while I'm home jerking off, but never the reverse?"

"That's right. Somehow it's fitting, isn't it?" Then she did the usual check up. Of course I was already hard.

"Aw, you want to be my little cucky?"

"Maybe."

"Stay right there." She came back with her laptop open and pressed play. It was a video of James Deen dominating a hot brunette who looked enough like Abby to make me do a double-take. Abby took out my hard dick and stroked it while we watched.

"Maybe sometime you can even have a live porn show starring me," she said, and only seconds later I blew a bigger load than usual.

Over our next few conversations it became clear that Abby had been considering this for a while. She'd even hatched a plan to make it happen in case I ever agreed. Her therapist had told her fetlife.com was a place we could find a community. So we signed up and made a profile together. For privacy we didn't want to put any pictures of ourselves, so we put a still of that porn actress who looked like Abby and said she looked like this. We described ourselves as a couple deeply in love looking for non monogamy. I wasn't ready to call myself a cuckold, so we left that out of it. We kept it brief.

Then we wrote an ad.

"We are a couple in love, but life events have thrown us for a loop and we've decided to spread our wings. We are looking for a community to help us explore non monogamy, as well as power exchange."

Now don't get me wrong. I wasn't fully into all of this yet. I did some of my usual hemming and hawing, but overall less than usual. The thing is, I'd never really thought about my girl fucking someone else before. With Jane and Lauren I never allowed myself to even picture it. It was too painful to go there. Now I found myself masturbating several times per day, sometimes watching videos like the ones Abby so enjoyed, but sometimes imaging Jane and Lauren getting fucked while I had to watch.

The fantasy hit me like a sudden storm. It was powerful. It made me cum quick and bigger than usual. It hit something deep inside of me, and made me feel both incredibly humiliated and turned on at the same time. It almost felt therapeutic in a way. Abby was clearly onto something, and so I kept rolling with it.