The Headmaster’s Story

Chapter 2

Gary seemed to have a real need to hear me tell him that I loved him, and so I repeated those three word several times that morning. Strangely, although I didn’t know it until that morning, I also needed to hear myself make that declaration, because telling Gary that I loved him, seemed to bring on profound feelings of self-acceptance and real joy for me. And once I made those feelings known, I learned Gary needed more, much more. He didn’t just want to be loved by me, he wanted to move in with me, and for us to make a life together. Even though all of that was new to me, I knew I also wanted and needed that. But unlike Gary, I was concerned as to how such a move would be considered by the school board, my ex-wife, my daughter, and Gary’s mother, not to mention society in general.

Gary and I talked for hours that day, and so that was when I learned Gary still loved his mother, but he hadn’t trusted her since she, in his mind, had told the world about her giving him an enema, and how that caused him to develop a full-blown erection. I never knew exactly what Ann Hamlin had actually shared about Gary’s enema procedure with Kathrin and Margret, but as far as Gary was concerned, she had told everyone that having something pushed up his butt caused him to get sexually aroused. I don’t think any of Gary’s other classmates ever teased him about what Brice had revealed, but as far as Gary was concerned they all knew every juicy detail of how he reacted to enemas, and so in his mind he had reason to never trust his mother again.

Considering how Gary wanted to guard such information, I felt it was strange that he seemed to want to share every detail and feeling regarding that experience with me. And instead of telling him I felt that none of what he experienced was a big deal, nor that enemas often cause teenaged boys to develop erections, I told him that even though I couldn’t explain it, his sharing all of that with me made me fall even more deeply in love with him. You might think such an acknowledgment on my part could have been upsetting to Gary, but his reaction was just the opposite. He all but leapt off of my couch and into my arms while declaring, “I knew it. I knew you loved me. You can’t deny it now because now I know it for sure.” Then Gary kissed me for the first time. And that was when I said, “You don’t have to worry about me denying the fact that I love you, Gary, because I do, and I’ll never deny it. And it’s really quite liberating for me to finally be able to admit that to you.”

Gary looked in my eyes, and said, “Thanks, I really needed to hear that.” And then after a pause, he said in a much quieter voice, “But do you know what else I’d like to hear?”

“No, What?”

There was another pause, a much longer pause, so long in fact that I eventually asked, “So, what is it Gary?”

The pause continued, but finally Gary said, “Just forget I ever said that. It’s too dumb and embarrassing for me to tell you.”

I pulled his warm body to mine, and said, “Oh Gary, you can’t leave me hanging like this.”

“Yea, but I want you to like and respect me, and not think I’m weird or dumb.”

After more silence, I said, “You know, Gary, we both just admitted that we’re gay, and the thing is, there are no rules for being gay. Gays don’t have an accepted missionary position, or a set of rules to follow. So, if what you want to hear from me is about sex, then you need to tell me because I didn’t just say I loved you, I meant it, and so I’d like to please you every way I can. And even though I was too afraid to tell you any of this before, you need to know that I’ve loved you almost all of your life.”

The silence continued to hang over the room, but then Gary finally said, “I’d like to hear that you’d like to give me an enema.”

“You’re kidding.” I said, feeling immediately dumb for having made such a remark after just making a speech about how open I thought gay sex should be.

With very sad eyes Gary looked at me, and said, “No, I’m not kidding. I really want that”

Then, while still on auto pilot, I said, “But after hearing how upset you got when your mother gave you one, I thought an enema would be the last thing you’d ever want to have happen to you ever again.”

“See, I told you you’d think I was crazy.”

“Yea, well if you’re crazy, then so am I, because the truth is, I’d love to give you an enema, or maybe one every day from now on.”

Instead of responding verbally to that statement, Gary leaned in and kissed me. It was an open mouth tongue licking tongue kind of kiss. The kind of kiss I hadn’t experienced with Kathrin in years. It was the kind of kiss that brought us both to full erection. And when we parted from that kiss, Gary said, “You don’t have to do it if you don’t really want to, or if you think it’s dumb. It’s just that as humiliating and embarrassing as my mother’s enema was, it was also a turn-on, and so I know an enema from you would be an even bigger turn-on for me. I mean, with you I want to be turned on. And with you I’d want to get a boner. And with you, I’d want you to see it because you’d know you were the one who made it happen. It would mean everything to me if you liked my butt and you really liked turning me on by sticking things up it. I know that sounds crazy, but I even want to cum for you while you know you’re the one who is turning my asshole on.”

I kissed Gary just as passionately as he had just kissed me. And then I said, “Then I really want to do it. I really want to give your cute little fanny an enema every day from now on, and I want you to cum every time I do it.”

Gary smiled a smile of relief. Then while looking directly into my eyes, he said, “Good, because I’ve been dreaming that you somehow became my father, and that you love me even when I get boners from having things stuck up my butt. And ever since I talked to you about my fight with Brice, I’ve been dreaming of you giving me enemas every night before I fall asleep. I even dream that you love the fact that the enemas you give me make me get boners. And you love my boners so much that you want to suck me off while you’re making me hold my enemas up my butt.”

…

I didn’t know it at the time, but Gary had a suit case and some cardboard boxes in both the trunk and back seat of his car that contained his most important belongings. And so, it was only moments later that we were moving him into my apartment. Yet Gary’s moving into my apartment wasn’t the only adjustment I needed to make. Because when it came to being gay, like Gary, I knew I was a bottom. I don’t know why that made me uncomfortable, but for some reason I was trying to avoid that bit of knowledge about myself. Yet because of Gary’s little confession, I suddenly knew being a bottom was a big part of who I was. And so because I wasn’t quite ready to admit my own bottoming tendencies, I didn’t yet own any enema equipment even though I knew deep down inside that I liked having things in my asshole just as much as Gary. So after moving Gary in we set out to buy our first enema bag. As it turned out, we not only bought a standard red rubber fountain syringe, but Gary also insisted we buy an adult sized enema and douche bulb syringe that came with an enormous almost phallic sized curved douche nozzle. And then a jar of Vaseline, and a bottle of Dr. Bonner’s Almond scented enema soap.

After making all of those purchases, Gary and I had tacos and burritos for lunch. But that evening we ate dinner at Bennington’s, one of Portland’s finest restaurants as sort of a celebration of our coming together. Gary ate with the elegance and manners of a mature adult, but all I could think about while watching him eat, was that I was going to give him the sexiest enema of his life the instant we got back to our apartment. I didn’t mention any of that while we were at the restaurant, but once we were on the road back to our apartment, I said, “You know, I really think you ate way too much tonight. And because I don’t want you getting fat on me, I’m going to have to give you an enema as soon as we get back to the apartment.”

Gary didn’t say anything, but simply smiled a kittenish smile. So I added, “Actually, the truth is, I can’t wait to get my hands on that cute little fanny of yours. I mean it Gary, I’ve never wanted to do something as much as I want to give you an enema in all of my life.”

I thought I had said all that needed to be said, but when I parked my car in our apartment’s underground garage, instead of getting out, Gary smiled and asked, “Are you going to make me hold my enema up my butt for a real long time like my mom always did?”

“Do you want me to?”

“Yea, to me it wouldn’t be a proper enema if you didn’t. And if you’ll let me suck your cock while I’m holding it in, I bet I could hold it in for a real long time.”

I leaned into Gary, and we mutually kissed in that darkened parking garage for several minutes. And when we were finally able to part, Gary said, “Come on, Mr. Christoph, let’s get up to your apartment. I really do need an enema, and I need it right now.