The Education of a Cuckold

by Alex Hathaway

  I made a point of staying out for hours, hoping they would be gone when I got back. I ended up having breakfast in town, and I spent two hours in a used bookstore, the kind you almost never see anymore where there is always another nook to explore and some dusty hardcover that you fancy might have the keys to your life somewhere in its yellowed pages.

  I got back to my dorm room around lunchtime. Unfortunately, one final indignity awaited me. Taped on the door was a photo of our two erect cocks. I couldn’t even remember a camera! Was there a camera? I guess when you’re stoned, certain details escape you. In the back of my mind a repressed image of Lisa holding a Polaroid camera up close to our cocks came rushing back to me. And Zach did have a Polaroid camera. We used it once to take a picture of a friend of ours who had passed out in our room. We courteously wrote the word “SHIT” on his forehead before taking the picture. And now … Shit!

  You couldn’t see the faces in the camera—that would have been enough to get them kicked out of school, or at least out of the dorms. But the size difference between the two dicks was incredible, if anything, even worse than it had been in real life. You could barely see mine sticking out; meanwhile Zach’s thick dick took up the whole frame, almost attacking the camera. You could see his silver wristwatch easily held around his cock, jutting into the frame. Had they put a wristwatch around his cock? I looked around before ripping the picture off the door. There was a voicemail on my machine from Alisha.

  “Hi Jason. I stopped by to see you earlier, to talk with you about your housing request. Come by my office to … discuss.”

  I found myself wondering … Did she know? Had she seen the picture? In a way it made me excited. I made my way down to her office right away.

  Alisha looked at me in a very curious way when I sat down.

  “So, I didn’t think we’d be able to find you a spot,” she said, going for the drama even though she had already decided to move me. “But … I realize you do need to make this move, don’t you?”

  She seemed to be challenging me to admit that I had a serious roommate problem.

  “Yes, I do.”

  “What I did,” Alisha said, “is open up another place in a four bedroom house. There’s a spot in the basement that’s pretty nice, but has not been fire approved. We were going to wait until the fall, but I’ve called the fire marshal and I think we should be able to get his approval.”

  “Okay.”

  “It’s a good house, two guys, two girls … quiet, seniors. A cat. Never heard anything crazy going on there.” Alisha seemed to look up with the emphasis on the word crazy. It had occurred to me while she was talking that if she had fucked Zach she would likely know about his silver watch, in which case, she would probably know exactly who was in that picture with him. But surely she hadn’t fucked Zach … surely?

  “Sorry we couldn’t get you in with the Deadheads,” Alisha said. “I tried, but they have a very popular house.”

  “That’s okay,” I said shyly, feeling that mixture of shame and excitement I’ve come to know so well.

  “And for the record,” Alisha said, “you should never let anyone intimidate you. I’m letting you move so you can get into a better living situation. But you should never let anyone feel they’ve gotten the best of you.”

  I wasn’t sure where she was going with this, but I really wanted her to continue.

  “We can’t change how we came into the world, but that doesn’t mean you settle for less,” Alisha said. “You keep fighting.”

  Alisha looked direct into my eyes. I knew then she knew exactly what we were talking about. She had definitely seen the photograph. And she knew who was who.

  Then there was a flicker of a smile. “Someone has a … serious advantage over you in one area, you gotta beat them in another. Got it?”

  I started to flush. Wow, she was just about to come out and say it. But we were in her office. Her assistant was in the next room with an open door. The moment passed.

  “If you have any … problems, you come talk to me, okay?” She gave me a big hug.

  I have thought about that meeting with Alisha many times in the years since. I know that she really cared for me and could tell I was in over my head in that situation. She got me out of there and into a better place. Maybe she realized I was turned on, and maybe she was too. But she realized I needed something different. I was too young to absorb that assault on my ego without losing heart.

  Chapter 7

  The folks I lived with in that new house became some of my best friends, not just in college, but in life. I owe Alisha a debt for that. It was as if she sensed what I needed. She wasn’t out to tease me or humiliate me. She wanted me to go out and claim my life. I think she realized I was too young and fragile for the full truth of certain things.

  But in the back of my mind I have been haunted by other things she said as well. About having a serious advantage in one area. I always wondered where that conversational road would have led. You may find this hard to believe, but in the collection of erotic encounters I’ve had, nothing turns me on more in retrospect than this one, which was not erotic at all, except for the secrets reflected in Alisha’s eyes and the use of the word “serious.” I loved that she wasn’t giving me the usual politically correct “size doesn’t matter” BS and admitting that Zach’s advantage over me was not just an advantage, but a serious one. Wow! Of course in my fantasies, she says “huge” instead of serious.

  And of course if the fantasy goes further … she closes the door to her office, asking me to show her my cock, to see if it is as small as it is in the picture. She jacks me off while telling me about how Zach is so big and so good in bed that she had to have him more than once, despite the professional risk. All the while remaining completely clothed in her professional attire, her white blouse and her conservative wool skirt, as she talks with me about what it will be like growing into adulthood with my size. It’s such a sexy scene because in my mind, she is both supportive and honest. Something I did not find for a long time.

  As for Alisha and Zach, you may think I am just assuming he fucked every girl on campus, but there was a very persistent rumor that he had fucked Alisha a number of times. I heard it from a couple of people, and years later Lisa would swear Alexis told me the same thing. At any rate it doesn’t matter now, but it does fuel that particular fantasy knowing it might have come close to reality.

  So I entered a different time in my youth, where I tried to make something of my life and worry less about girls. It was a time of hitting the school books and hanging out with supportive friends. I finally realized that who I surrounded myself with mattered. And what I directed my energy toward mattered too. I could ether feel sorry for myself, or I could start kicking ass and make myself a man.

  I decided to become a teacher, and I worked hard at it. I did internships at local schools, got involved in community teaching projects, and figured out what classes I would need to take before graduating to get state certified. After a long day, instead of coming home to some guy having sex with a girl I craved, I would come home to a Scrabble game, or sometimes even Magic: the Gathering. And my life felt right.

  I learned something very interesting about women along the way. I found out that when I stopped chasing them around and focused on accomplishing good things, they were drawn to me instead. This revelation didn’t rid me of the performance anxiety I sometimes felt in the bedroom, but it did rid me of my “dating anxiety.”

  “Do good shit, make a name for yourself and the girls will come to you,” was how my friend and housemate Greg put it to me during one of our great late-night talks. He was right, and it was working.

  As for the bedroom, I’d be lying if I said I had a ton of sex the next few years, but I did okay. I focused on eating pussy. Girls at my college were really into oral sex, maybe because their high school boyfriends were hopeless at it. It seemed like something I could master. I even went online and read up on techniques. I figured out exactly when to
work directly on the clit with my tongue and when to pull back and work it indirectly when the clit became too sensitive. I got pretty darn good at it, maybe even got a bit of a positive reputation. I realized how much women liked to feel like you want to devour them down there. Passion and technique weren’t such a bad combination.

  The year went by quickly: graduating from college was a triumph for me. I even spoke as the class valedictorian. I said some idealistic things about us changing the world I no longer truly believe—turns out the world is a lot tougher to change than I realized then. But the words rang true at the time and my classmates liked that I threw down the word “bullshit” not once, but twice, much to the consternation of our school administrators.

  After the speech there were high fives and an impromptu road trip all the way out to the Grand Canyon. I managed to squander a couple of months in the glorious style of youth before my final New Hampshire teacher certification course kicked in. It was crazy to think I’d soon be teaching writing and literature to junior high school students, but there wasn’t any graduate school requirements beyond the state certification. I was in.

  Chapter 8

  As you can imagine, my first year in the classroom was tough. The toughest part, however, was outside the classroom.

  I thought it would be cool to have my own place for the first time and live in a small town off the grid. I moved west into rural life and fell into a social hole. The rental prices were cheap and I could live like a king even on teachers’ wages out there, but it was no longer easy to meet girls.

  I began to drive into the city on weekends to go “clubbing,” and there my old dating anxieties kicked in hard. The club life was maybe my worst self-esteem decision ever. Clubs were great for groups of guys; cocky sexual predators seemed to rule the day. I would try to flirt with girls at the bar, but it felt forced. They would let me buy them drinks sometimes, but then I’d catch them in a slow grind with big beefy guys.

  The whole thing tore away at me. I was once again confused about my sexual place in the world. I seemed to have a soft spot for the kinds of über-confident women who wouldn’t give me the time of day. A couple of my fellow teachers seemed to like me, but they were bland. Some of the hot-tongued women at the club just drove me crazy. One of them, Angela, took a liking to me after I picked up her bar tab and got her and a friend into a cab when they were drunk. I even called her the next day to remind her where she had parked her car.

  Things changed between Angela and me after a couple of bump-and-grind sessions on the dance floor. The sexual energy between us faded and it did not even occur to me to think she was “sizing me up” by grinding her ass against me. I was terrified of the modern-woman-as-sexual-consumer, and perhaps with good reason. But I did know that once the sexual chemistry changed, for whatever reason, I was impotent to rekindle it.

  Several years went by. I loved the classroom but started to despair for myself outside of it. I finally admitted that clubbing was a bad way to go. Besides, I was staying up way too late on the weekends and when you’re a teacher, dragging ass on Monday is the worst. You can’t just fake it in front of unruly kids and suck down coffee like you can with an office job. I was done with the clubs. I was never going to be a player, even if my dance moves weren’t bad. There was a freedom to dancing your heart out by yourself on the floor, and I even got some admiring stares, but in today’s clubs, it’s about the bump-and-grind.

  Chapter 9

  When you think back to turning points in your life, how many did you see coming? At the time I met Kristen, I was twenty-six. Perhaps young by relationship standards, I felt like I had grown up a lot. Teaching had a lot to do with it - a few years of high school teaching had imposed some discipline on my schedule. Partying into the night and taking roll-call at the crack of dawn don't mix.

  I had been out of the club scene for about a year - not that the club scene in Savannah, Georgia was anything too crazy. Savannah's music cafes were more my style, and I could hit those early. I even tried my hand at a few open mikes with my trusty acoustic and not-so-trusty vocal work. My dating life still wasn’t great, but it had improved after leaving the clubs in favor of volunteering for local projects, taking community college classes, and so on. I was pretty busy with work anyhow … or so I told myself.

  Once again it was so much easier to meet women in those informal settings. I had starting dating casually again, even had a couple of short relationships with women I met during that time. I wouldn’t say that the sex was mind-blowing, but I blamed that partially on my own lack of attraction to the women I was dating. I hadn’t found the right girl. I was forcing myself to keep an open mind, maybe to a fault. That was about to change.

  At the time I met Kristen, summer was ending and so were my summer music classes. Teaching was still going well, if you accept "intense" as the definition of "well." I did at the time. I wasn't ready to call teaching my career, but I liked the summers off and the curve balls of the classroom. I was still in that youthful idealism phase where teaching in public schools for questionable pay had an allure to it. And it wasn't just being a hero. Some of the kinds I worked with really were at a crossroads between dropping out and finding a voice or a passion or some kind of way into college. That feeling of being at a fateful crossroads - it reminded me of so many of my friends. On good days, it seemed like I could maybe make a difference. The bad days were, well, enough to keep my mind open to occupational alternatives.

  I thought high school students might disrespect me due to my youth, but they seemed to like the fact that I listened to their music and got most of their jokes. Plus when it came to literature and writing classes, I knew my shit. Or at least far more than they did. But there wasn't a lot to offer me socially on the job, aside from some crusty lessons-in-life from balding teachers warning me of the perils of the profession in a teacher's lounge with busted sofas. I needed to something else. I thought maybe massage would be a good skill to add to my bedroom repertoire, so that fall I signed up for a massage class. With the school day almost ending by 5 p.m., an evening class would fit right into my schedule. And I won’t lie; a big part of it was the flyer.

  The girl in the flyer, Kristen, was faded from the photocopy but even with the poor quality photo on dark red paper, her natural beauty leapt off the page. I could see that utter confidence I am a sucker for, but also something else: her eyes. There was a magical combination of wickedness and kindness. She didn’t look like a beauty queen but some kind of earth mother creation born out of sun, sand, and sculpted by the elements.

  Even though Kristen was older than me, I felt a connection to her from the get-go. I think she felt it too. The first time she handed me a mat for our first class, there was something. And her eyes … yes, the flyer had not let me down.

  It’s always great when a friendship naturally flows. So it was with Kristen. I think it was only the second class where a bunch of us were standing around, drinking water from the cooler when Kristen suggested we all go out for coffee. Two hours later, the five of us were down to two. I could sense that Kristen had a boyfriend, and she had to be a good five years older than me besides—eight years older, as it turns out.

  It was the way we could talk about things. Coffee became a weekly ritual, with her and I lingering on after the rest of the group dispersed. It was maybe the third coffee when she told me about her sister dying of breast cancer two years earlier. In turn I told her about a friend of mine who had killed himself his first year in college. It wasn’t like we were therapy buddies, though. Just that we trusted each other from the start. We could just as easily dissolve into bouts of laughter, as she did when she learned I had memorized the names of all the Duran Duran band members. Or when I found out she actually liked watching Doctor Who.

  The fourth week of the coffee socials, she surprised me.

  “Let’s get a real drink tonight!”

  With her I was always up for anything, so when the coffee pals left, it was the two of us walkin
g to a smoky neighborhood bar on a weeknight. There was nothing sexier than watching her smoke a cigarette on the bar’s fenced-in patio. Something about a yoga and massage expert taking an unapologetic drag … it worked. The hard part was pretending to be just her friend when I wanted so much more. But I could tell that hitting on her would just put me in a category with so many other guys. Her body was just unfair. If you watch Jennifer Garner in Daredevil you get some idea of what I was dealing with. Muscular but still feminine, brave and strong but still flirty. Kristen could be intimidating … wheat grass and vodka shots with us. Kristen could make people get along so easily, trick them into drinking the most bizarre concoctions just to be a part of her world. Then we were alone again, sitting at the darkened end of the bar as the bartender stocked glasses on the other.

  “So … do you have a girlfriend?”

  I shouldn’t have been surprised by the question.

  “No…” I said. I meant to say, “Is that an invitation?” but I chickened out. Dammit I had lost confidence again.

  “Can I ask … why not?”

  I hesitated.

  “I mean, you’re a really fun guy, you’re cute…”

  Cute wasn’t totally what I was looking for, but …

  “You have a good job, you give a shit about the world … did I say you have a good job?”

  We had just been talking about her history dating guys without jobs or careers to speak of, and how awkward it gets when a massage therapist has to pick up the bill. Thus her “you have a good job” joke.

  “I have trouble meeting girls outside of school,” I said, grasping at straws. “That’s really why I took this class.”

  “Well, I’m going to introduce you to some of my friends if you’re not careful,” Kristen said.

  And she did. Not right away, but over time, at parties, at concerts. Sometimes she would even show up with a guy, but I noticed with some relief it was not always the same one. I guess that turned me on a bit also, how free she seemed to feel to be with one person or another. No one had it over on her. I started trying to work up the nerve to ask her out. If she was going to show up with different guys, maybe a younger guy wasn’t out of the question. I had been single for a while again, and was kind of lost. I felt like she could rope me in, teach me some things, maybe put me on a good track again. I was a little scared by the longing I felt around her and her mysterious elusiveness. I guess I was concerned I wouldn’t be able to “make her mine,” but maybe that was the point. Maybe what mattered was that I could make her feel good, the way she made me feel around her.