Gabby's Bar was pretty noisy, yet after we got our pints, Caleb leaned over the table so that he could whisper, as if he feared someone might overhear. One of his black curls slipped over his left eye, and his cheeks flushed a gorgeous blush.
"You're making me gay. I can't come over to your place anymore."
Wow! Why do I keep finding men who blame me that they want to fuck?
Now I understood why he wanted to meet at the pub and not at my apartment. Both times he'd been there had resulted in some very gay sex, and he was a guy who was super religious, meaning homophobic, leading I'm guessing to self-loathing. It was a familiar pattern.
I chose not to argue. I didn't point out that we met through a gay dating app. He signed up for that before he met me, so he can't claim to have had no gay thoughts before our first hook up.
Yet, I knew there was no point in arguing with someone who is so deep in the closet. Instead, I just apologized for nothing and changed the conversation to talk about our college basketball team's chances in the state wide games. Since he was on the team that worked. We chatted awkwardly for half an hour, giving me time to finish my beer politely and get the hell out of there.
"So I'll see you around?" he asked before we parted ways on the sidewalk where it passed under the stone arch that bordered campus. He would turn into the quad to go to his dorm, while I'd walk half a mile off campus to my apartment.
"Sure," I said. "See you around."
Truth is I'm tired of guys who can't admit they love me, so fuck him. When I got home, I started trolling the gay dating app again, hoping to find some cute guy closer to thirty like me who embraced being gay. I was totally caught off guard an hour later when Caleb messaged me through the app. He must've viewed my profile and saw that I was on line.
You looking for someone else?
Wow. He even used punctuation to be clear. How to respond to that comment?
Yup figured I should find someone who's gay and all
oh right I understand
I figured that was that, but over the next couple of weeks he still messaged me, usually through the app, I guess because he felt safer there since it was thumb print protected and discreet. He surprised me by sending a pic in just his basketball shorts after practice, his pale chest glowing red from exertion, his curling locks plastered with sweat to his forehead. He had to know I'd masturbate to that picture. Did that turn him on?
I upped the ante, setting my phone up and using a timer so I could get a full shot of me lounging naked on my couch reading a book, one leg up to carefully hide my junk. I received a heart in reply for that shot. I'd half expected him to block me since this could be defined in his mind as me trying to turn him gay, but it was a gay dating app for fuck's sake. He was still on the app!
It was Monday evening when his next message pinged, and it stunned me. He must've been holding the phone under his chin, naked, because it was a dick pic, his flat stomach in the frame, his finger and thumb around the base of his nice cock to point it straight out, the head a bit skinnier than the rest, but still a good seven inches. I wanted that in my ass again. The picture was captioned:
Sorry I've been such a dick
I sure as hell put a heart on that. I even found a boner emoji. An hour later he stunned me with the opposite:
Just that I don't want to be gay
Oh fuck's sake, I was fed up with his baggage. I didn't respond.
But a thought did take hold, a fantasy. How long could he go without hooking up with me before he popped? I'm guessing after he sent the dick pick, he blew his load, thus the
don't want to be gay
comment an hour later when the pressure was off. But it would build again, and I wanted to be ready.
Friday, I visited a big box lumber/hardware store. The couple who lived in the top floor apartment of this house had left for the weekend, so I didn't need to worry about them being disturbed by the noise of power tools in the basement. I was lucky our landlord stored them here, and he had once said I was free to use them if I needed to help a friend build a deck or something. I'm sure he never imagined what I wanted to build.
Saturday morning Caleb popped. He sent me a smoking hot shot of him in just his basketball shorts, the picture taken in the mirror of his bathroom in his dorm, the phone blocking his face. There was no way he was wearing a jock underneath or even underwear, because the shorts tented prominently, a wet spot of precum at the top of the pole. There was no comment or caption with the shot.
It took me half an hour to decide how to respond. Let him stew for a bit, maybe even wondering if I'd hooked up through the app last night and was now snuggling with my lover in bed. If he's not gay he couldn't be jealous, right? Finally, I put a heart and a boner on the picture. Then I set the lure.
I deserve to be punished for trying to make you gay
My heart pounded while I waited for his response, and I got painfully hard. I shucked my jeans and stood naked, enjoying texting nude.
??????
That was a pretty neutral way of asking what I meant. Given that he'd once asked me to "flog" him to punish him for having gay thoughts, I figured he must have some clue as to what I was suggesting. I sent an order rather than an ask.
My place 7 pm The front door will be unlocked Come in Lock it behind you You'll find me in the basement
I followed up by turning to my front hall mirror, holding my phone in front of my face like he did and taking a profile head to toe shot of my lithe, naked body, my erection with its fat head very prominent. I sent the pic and held my breath.
OK
Fuck! What did that mean? Was he going to show? Did he know what I was suggesting?
The day passed quickly as I refined my toy: sanding, duct taping pillows onto the bench, nervously assuming the position to test for fit and comfort. Except when doing word work, I spent the day naked, the heat turned high, a boner often popping up. Outside a light snow fell, a reminder that winter was in full swing.
After dinner, I showered before heading to the basement to light candles. I wanted no other illumination. This was my medieval setting. I surveyed my handiwork, caressing the wood to check for splinters. A traditional pillory like the puritans used forced the prisoner to stand with his head and wrists in the holes so that crowds could throw crap at them, but I needed my device to give Caleb the best access to my body for sex. That meant setting it up so that I was bent over on my knees.
When it was almost time, I knelt on the foam camping mat and leaned forward into my pillory. I rested my chest on the bench with the pillows duct taped to it, making sure I was comfortable. It fit from my belly button to my nipples, so my weight was evenly distributed. My erection had lots of room to point forward. I didn't want that crushed or obstructed. I lowered my head and wrist into the half holes that I'd cut in the lower board, checking for fit. Yup. I had designed it well. My neck and wrists were comfortable, exactly where I wanted them with no strain.
Now the hard part. I reached up to the board with the complementary half holes with my left hand. It was on a hinge, so I gently swung it down, and the last second before it dropped into place, I slipped my left wrist into the slot. I was an awkward maneuver, forcing me to try and guide the upper board down with the back of my wrist. It fell a little faster as I lost control, but when it smacked down, I was properly in place: my head and wrists trapped in the wooden holes. The holes didn't fit tightly, but I definitely couldn't pull my hands out and of course my head couldn't pull out through the hole for my neck.
This was perfect. All Caleb had to do to make me completely helpless was to put down the hasp on my left and put a padlock on it so that the upper and lower boards of the pillory became like one board with the three holes for my wrists and neck. I knew a second of thrill before I noticed a horrible mistake.
When the top board bumped into the bottom board the hasp must've fallen, swinging forward on its hinge to fall over the loop. Even though there was no padlock on the loop, I was stuck. I tried bumping up with my wrists and neck, hoping I could jiggle the hasp off its loop, but it was firmly in place. I made a note to rotate the hasp 180 degrees so that it had to be lifted up to be put in place and the padlock would be needed to keep it from falling open. Easy design fix if I ever got free.
Fuck! What if Caleb didn't show? He'd only messaged "
OK
." Now I wondered what that meant. Again, I slammed my wrists and neck into the upper board, still hoping I could jiggle the hasp free of the loop but it held stubbornly in place. Why did my craftmanship have to be so good that the loop lined up so perfectly with the hasp?
My erection melted. In fact, my penis by the feel shrank in fear. If Caleb didn't show, I'd be stuck like this all night, waiting for the couple who lived in the upstairs apartment of this house to get home from their cabin up north. Then I'd have to scream for help. They'd have to get the landlord or the police to get into my apartment on the ground floor so that they could get down to the basement. How to explain that I was naked and trapped because I was playing a game and it went wrong? My cheeks already burned with the humiliation.
The sound of the front door opening was sweet music.
"Jamie?" Caleb called out from upstairs.
"I'm down here!" I shouted with relief. The worst-case scenario now was that he'd be appalled by my nudity, by my submission, and would want to leave. I'd just have to beg him to lift the hasp before he bailed.
The steps creaked as he descended. I'd arranged the pillory so that the first thing he'd see as he turned into the unfinished basement was my bare ass. His breath drew in sharply.
