The Headmaster’s Story

Chapter 3

Gary was all cozy and snuggly on our walk up to my apartment. That was an amazing experience for me, as I couldn’t remember Kathrin ever desiring to be so sensuously close to me, nor so innocently cute. Actually, when I really think about it, I think Kathrin may have been that cute and cuddly back when we were in high school, but that was so long ago I can’t say for sure.

Gary and I walked arm in arm from my car to the elevator, and then kissed passionately on the non-stop ride to the 4th floor. But once the elevator doors opened, we walked the rest of the way to my apartment like a father and son, a situation that wasn’t to last, because once we were in the sanctity of my apartment, Gary was all over me, and I him. I eventually pinned him down on the couch, and said, “Stop squirming. I want to feel your tummy.” But instead of putting my hand to his warm tummy while he purposefully pushed it out until it was pregnantly taunt, I put my open mouth to his belly so I could make an obnoxious fart sound against it. He giggled like a baby while I smiled and said, “Just as I thought. Your tummy is way too stuffed. I’m going to have to give you a really big enema or you’ll surely be sick by morning.”

Gary suddenly got serious while saying, “Thanks for loving me. You have no idea how much you mean to me.”

I kissed him again, and he just looked at me. Finally, he said, “You know I’ve been dreaming of this almost all of my life. I hope you know I’ll let you do anything you want to me as long as I know you love me. You could even spank my bare ass, and I’ll still love you. In fact, I’ve dreamt of you doing that too.”

That brought an involuntary smile to my face as I said, “Now why would I ever want to spank your cute little bottom?”

Gary smiled, and without hesitation said, “Because sometimes I’m a brat. My mom used to spank my bare ass all of the time, but then one day she just stopped.”

“So, are you telling me you actually want me to spank you?”

“Only if you think I need it, and you think I’ve been bad. But then I get to spank your bare fanny too if I think you’ve been bad.”

I couldn’t help it. I took Gary in another hug and kissed him again. And while doing so I pushed my hand down his stomach, into his trousers. Then I worked my hand under his underpants so I could take his penis and testis in my grasp. He moaned softly, the kind of moan that told me he was in ecstasy. So, while continuing to kiss him I massaged his penis until it was fully erect. That was the first time I ever touched another man’s or boy’s penis, and it was instantly addicting. I then unzipped his trousers and lowered them to his thighs. Then I slowly lowered his underpants to reveal a band of white boy flesh circling his body at his hips, all to reveal a perfectly circumcised erection protruding from his pubis. I immediately wanted to take it in my mouth, but instead I worked to slip his trousers and underpants all the way down his legs, and then completely off.

Gary was on his back, and was then nude from the waist down with his penis rigidly pointing up his belly. It seemed so truly magnificent that I could no longer resist taking it in my mouth. And even though that was another first for me, I began sucking on it as if it was the most natural thing I could do. Gary closed his eyes and moaned softly as I let my hand roam freely over his stomach and chest while I played my tongue all over his cock, something I continued until Gary raised his knees to his chest, an act that presented me with the cutest little pink asshole I had ever seen. I pulled away, and while my eyes were laser focused on Gary’s anus, I said, “It looks to me like you want your enema right now?”

Gary smiled a little boy smile, as he said, “I love everything you’re doing to me. But like I said, I’ve been waiting for this enema for as long as I can remember.”

I’ll admit that the idea of giving a cute boy an enema was intriguing, but because I had never actually given an enema to anyone other than myself, I decided to start off slow. So, after telling Gary to get completely undressed, and into my bed, I went to the kitchen and filled a mixing bowl with warm water. And then after retrieving the bulb syringe and Vaseline that we had just purchased, I took them, and the bowl of warm water into my bedroom.

Gary was all eyes when I entered the room, and so watched my every move as I put the bowl and syringe on my night stand. And he continued to watch me as I slowly pulled the covers from his slight body while realizing that nothing could have been more beautiful than Gary as he laid nude before me. Even though Gary had turned 18 by that time, I couldn’t help thinking of him as a much younger boy, to the point I couldn’t help wishing I had spent my whole life with him, and couldn’t help wondering what it must have been like to be with him as he submitted to his earlier childhood enemas.

I smiled at Gary, hoping my smile would convey the love I was feeling for him as I put my hands to his body. While speaking no words, I repositioned him so he was laying on his left side facing away from me with his legs jackknifed so his knees were almost to his chest, a position that left his naked buttocks looking so cute, and his anus so available. I couldn’t help smoothing my open hand over the soft white rounds of his buttocks before I raised his right butt cheek and actually touched his anus for the first time. It drew up as if it were puckering to kiss the pad of my finger, so I let my finger tip linger on the clenched muscle as I subtly worked his anus with slow sensuous movements. Without realizing it, I had closed my eyes, and when I opened them, I saw Gary pulling his legs up even tighter to his chest, so I asked, “Are you sure you’re ready for this?”

Gary answered in a soft breathy voice without hesitation, “I’ve never been more ready for something in all of my life.”

Remembering my own childhood enemas, and the feelings and sensations they evoked, not to mention the unwanted boners, I said, “Good, because now I really have to do this. So just relax while I lube your anus, and stay relaxed because I’m going to stick my finger all the way up your bottom so you’ll be able to take this huge nozzle all the way to its hilt.

An impish smile came over Gary’s face as he asked, “Are you going to stick your finger up my butt to grease me up? Or are you going to stick your finger up my butt because you want to turn me on?”

I thought for a second, and then answered, “Both.” But after thinking for another second, I added, “But mainly because I really just want to do it. It’s just something I have to do. I want to feel the inside of the boy I love, and I want him to feel my finger loving him from inside his body.”

I massaged Gary’s soft white butt cheeks, kind of pinching his butt globs as I watched how those pinches distorted his anus for a few seconds before I actually began to spread Vaseline over the tightly clutched closure. It was all so sensuous that it totally hardened my dick before I began to slowly work my index finger through his anus and up into his rectum. Gary’s anus and rectum seemed to come alive as they sensuously gripped my finger as if he were trying to show me the same love I was feeling for him. I couldn’t help working my finger in his rectum for some time before I finally withdrew and inserted the enema bulb’s huge white douche nozzle, twisting and turning it as I worked it further and further through Gary’s sensuous anus and rectum. Only when the flanged neck of the enema’s bulb was seated against his anus did I begin to slowly squeeze the bulb until it was flat. And then I folded the collapsed bulb over on itself and squeezed it some more. Gary was moaning in ecstasy, so I slowly withdrew the nozzle and refilled the bulb from my bowl of warm soapy water. Gary turned onto his belly to receive the next two injections, and remained in that position until I finally left the bulb in the bowl and reinserted my finger. Gary was jacking on his cock with earnest while flexing his butt cheeks up tight on my fist while his rectum seemed to all but suck my finger even further up his behind.

And then it happened. Gary climaxed, pumping his boy cum out in great spurts all over my bedsheet while his rectum and prostate seemed to go wild with strong muscular contractions that seemed to telegraph his ecstasy through my finger and up into my whole body so I could share in the splendor he was experiencing.

I had always thought Gary was cute and boyishly handsome, but he was ten times that at that moment. I couldn’t begin to explain how I felt about him, because I felt a love and need for him that was more powerful than anything I had ever felt before. I was so taken by how the walls of his rectum seemed to contract and harden as his prostate began to spasmodically pump his boy jiz out, all while his rectum seemed to convey a most erotic love to my inserted finger. I couldn’t stop working my finger within the convulsive clutches of his rectum until he finally came to rest. And the moment that happened I collapsed on him and began kissing all over his neck and back.

Gary eventually turned back to face me while saying, “Brice and his buddies at school would never have teased me if they knew how wonderful a good enema could feel.”

I kissed Gary’s lips, and then asked, “So, did I do it right for you?”

“Yea, it was perfect. But now I really have to poop this out.”

I smiled at Gary, and then kissed him again, a long tongue sucking kiss that lasted until Gary fought to get away so he could make a run for the bathroom.

…

Because school was out for the summer I had a lot of time I could spend with Gary. Time that we spent loving each other in Gary’s wonderful ways. It was a time for me to learn how to enjoy being me, rather than me trying to learn how to fit into some heterosexual role, or into Portland’s gay community. It was a time we spent making absolutely wonderful love to each other while being our real selves. And it was a time for us to learn how to please each other for the rest of our lives.

Gary, against my advice, told his mother that he was gay, that he had always been gay, and that he loved me. He even went so far as to tell Ann he had always wished that I had actually been his father. At first Ann was very upset with me, and seemed to blame me for Gary being gay. But when Gary told her she had better learn to love me as much as he loved me, or she would never see him again, Ann seemed to immediately understand, because she and I have been good friends ever since.

I’ll admit it took a while for thing to calm down with Kathrin and Megan. Actually Megan had the most adjustment to make as she had always hoped she and Gary would someday be a couple, and that it would be her who would get to feel and experience being loved by Gary Hamlin. Yet, before that summer ended things were pretty much back to normal for all of us. As for the Paulsons, they became all but invisible to us. Brice moved away to attend Louisiana State University, while Gary went on to attend Portland’s Lewis and Clark University. And because I was then paying for all of Gary’s student expenses, and half of Megan’s, I finally decided to do as Kathrin had always wanted, which was to look for a better paying job.

Fortunately, my job search couldn’t have been more perfectly timed, as a private British foundation had purchased a vast estate two years before with the intention of opening a residential, British style, all boys’ preparatory school to serve the sons of Portland’s wealthier set. Construction of classroom buildings, dorms, and utility structures had just been completed, and the estate’s stately stone mansion had been remodeled so that its basement and first floor were ready to serve as the school’s administration offices, leaving its second story for its Headmaster’s private quarters.

Even though I felt their general offering and salary would have been perfect for me, I didn’t really feel like I had much of a chance to land the headmaster position. As you might imagine, the headmaster position was such that it warranted a thorough background check. The board of directors not only looked into my previous employment, but into my relationship with my ex-wife, my daughter, and even our neighbors. As a result, I all but gave up on the idea of landing the headmaster position. Yet, after everything was said and done, I seemed to be the exact kind of person they felt would attract the more liberal wealthier parents they wanted to serve, and so I was offered the headmaster position while openly proclaiming to be gay. They were even open to the idea that I would be moving into the headmaster’s quarters with a gay lover whom they knew I intended to marry.

Six years have passed, and Gary and I are not only husband and husband, but Gary is teaching history at the New Bedford School for Boys while I continue to serve as New Bedford’s Headmaster. Even though Kathrin has not yet re-married, she, Megan, and Gary’s mother are all very happy for us, while Gary and I continue to make each other happy in ways that we know none of our family members would ever understand.

The End