The rest of the weekend we had spent mainly cuddled on the couch alternating between movies, Cowboy Bebop, Samurai Champloo, and Avatar the Last Airbender. Dan was kind enough to prepare lunch for me. I was hesitant to go much further that weekend.
We would continue with the oral play, but I held back. It wasn’t that I didn’t want to, but more I didn’t really know how to go about asking for what I wanted. I would overanalyze this for weeks before finally committing to make my move. Eventually.
Dan and I lived in a town that has been written about enough times already that I won’t be able to come close to the descriptions that other authors have already covered. We’ll just say the town is Derry Maine, complete with the Paul Bunyan statue, The author’s house itself, and Mount Hope Cemetery. It’s the quietest little big city you could ask for. Just enough activity to always leave you wanting to do something more.
A few weeks had passed and the build-up was starting to hurt. I would have to relieve myself nightly thinking about the forbidden things I wanted to do. So far, I knew I was bi but hadn’t given in to my desires up until this point. Everything was new. My only experience so far had been with my ex.
Ugh, my ex. We were just out of our relationship again. I didn’t like thinking about her, but she would find her way into nearly every waking thought or dream I had. Even when I was with Dan, I still would think of her and feel guilty. With every kiss, I would remember how she tasted, and I would start to feel that familiar self-hatred rise that had been ever-present in my life for as far back as I could remember. This self-hatred walked hand in hand with my depression and anxiety.
I looked over at Dan who was now engrossed in the game he was playing.
“Hey, I wanted to ask you a question.”
“You know, you don’t need my permission, ask away,” He replied.
“Well… My dad lives about twenty-five minutes away. You know that Sleepytown?”
“Yeah…”
“Well, I usually head up to his house every summer off and on for a few weeks. I was planning on going up this Friday for ten days and I was hoping you would come with me?”
I waited patiently for his answer. I could tell he had already decided as soon as I said it. However. he loved to torture me.
“That sounds like it could be a really good time. I’d love to go. What about your dad though?”
“Oh… well, I’m not really ‘out’ with anyone. Except for you of course. So, I was hoping. I mean I know it’s stupid to ask but… Could you just...?”
“Pretend to be straight. Got it. I don’t mind. I get it. We’ll just be ‘best friends’ this weekend and I’ll cool it with the. Stuff.”
“Well I mean,” and I muttered quietly, “your eyeliner is kind of cute.”
“Hey, don’t be gay now,” he winked and gently punched my shoulder.
I had packed to leave for my Dad’s house. Dan was permitted to stay the night, as my dad would be coming through early in the morning when he got out of work. My grandparents had set up a cot for Dan that we didn’t use at all. I liked sleeping with him. He was warm and listening to his heartbeat would give me the sleep that insomnia had robbed me of.
We drove the twenty-five minutes from Derry to Sleepytown. We passed by Dysart’s and the trash mountain; my father would always try to fight the stench by turning off the AC. It didn’t help. We pulled off at the exit and drove through the town. The small shopping center was off to the left, and a car dealership that made no sense for a town this small was on the right. The town had two stoplights, and only one of them was turned on. Most people ignored it because there were also only two police officers that worked for the town, the sheriff’s department providing additional assistance when needed.
We pulled into the driveway and picked out bags out of the trunk. I brought Dan upstairs to the bedroom we would be sharing. In the guest room, they had a queen-sized bed and a full-sized bed across from each other. We looked at each other and smiled knowing that the full-sized, much like the cot, would go unused.
I felt free. Liberated. For the first time, I was allowing myself to explore a side of me that I had always suppressed. I was happier than I had felt in a long time. I grabbed Dan from behind pulling him into a hug. I was slightly taller than he was and leaned down to kiss his neck. He just let out a low soft breath that made me pull him tighter.
After taking way too much time ‘unpacking’ we headed downstairs. I told my dad I was going to give Dan a tour around the town as an excuse to just get out of the house and be alone together. Almost no one goes out of the house in Sleepytown unless they absolutely must. You may see cars at the Cianbro facility, or in the grocery store, or a rare car may drive by, but other than people who MUST be out it is a ghost town. The town seemed to have this perpetual thick layer of white clouds above even during the summer so that it really gave the effect that there was some sort of enchantment over this place and time would behave funkily. Ten days would feel like an entire summer.
We walked to the train tracks, following them away from the main street and to a pathway off to the side of the tracks. Following this led to a bridge where we paused to hold hands and just talk. Here I looked down because I was embarrassed about what I wanted to talk about.
“I… I’ve wanted to talk about something for a while, but you know how I am and I just…” My face was already red, and I felt like I was going to just explode. Dan squeezed my hand tightly.
“It’s okay, take your time.”
“I wanted to ask you for sex!” I quickly blurted out. I didn’t know how to ask or what to say. This was all new territory and I was figuring everything out all over again.
Dan just looked at me and laughed.
“Come here, dummy,” he said as he leaned over to me.
I kissed him on the bridge, pushing my tongue into his mouth and exploring every corner of it.
My Dad would be leaving for work the next night, not to return for a few days, and my stepmother worked overnights every night. They both slept all day when they were home because of the strain of their long hours, and it seemed nothing could wake them.
We walked around the rest of the town and I showed you the library, the train car that the historical society was repairing, the theater that was a movie theater that showed movies on a stage theater with a projector. A theater on a theater. We walked around for hours returning to the house that night.
My family gathered around everyone smoking, playing card games for pennies, and talking about everything. Often there would be three conversations going and you would be the participant in two of them at the same time. Dan decided to test the limits, reaching into his pocket and pulling out a pack of Marlboro’s.
“Dan,” I whisper-yelled, hoping he would get the message. I don’t know why I worried, my sister had smoked since she was fifteen and no one said shit to her. Although she also ruled the house with an iron fist because crazy bitch gone do what a crazy bitch gone do.
Dan lit the cigarette anyways, his smoke joining the mist of everyone else’s. No one even batted an eyelash to this, my anxiety getting the better of me thinking there would be yelling or lectures on smoking. Having strong religious convictions pressed upon you from the time you are two can leave you with the pressure that Catholics can often relate to. This added to your standard anxiety just made me squirm at almost everything.
The night passed and my dad left for work. The house was dead, and Dan and I were alone. We both had our feet up on the kitchen table, watching re-runs of family guy on TBS. We looked over at each other and I knew this was the time. I walked over to him and grabbed his hand, gently but urgently walking him to our bedroom.
I locked the door behind us and turned around to see Dan was already laying out across the bed with his arms over his head. I walked over and crawled on top, pushing his arms over his head and forcing a kiss on him. He feigned fighting back as I began to hold his arms with one hand, the other reaching into his pants, feeling his stiff hot cock growing. I jerked him off at this odd angle with my hands in his pants, holding him up while I kissed away at his neck.
He finally got the strength and ‘broke free’ from my grasp, pulling my shirt off my in such a quick move that for a moment I thought he had just ripped it. I smiled and reciprocated, tearing his shirt off him like he was an Indy 500 driver and he was on fire and I was going to save him.
I leaned back onto my butt and started to grind against him slowly. I looked at him and he knew where I wanted to take this, but he knew how shy I was, so he just went along wordlessly giving me whatever I wanted.
He reached his hands to my pants and undid my button with one hand while simultaneously pulling down my zipper with the other. He was amazing at this. He gently tugged, pulling my shorts down to just below my hairline. He ran his hand palm down up my belly and to my chest resting it there, with one hand tucking into my lowered pants and just pulling me in tune to my grinding.
I reached down and undid his pants as well. I lifted myself up enough to get my pants up. I was trying to make it look good but ended up looking like Bambi trying to walk on the ice. He suppressed a giggle, but I knew he was suppressing it. I ignored it, eventually being successful in removing my pants. He yanked his pants off while I straddled him, kicking them off with his feet once they were by his knees. He did this with a speed that I still could not believe. It was like he was the Harry Houdini of fucking and clothing escape was his specialty.
We were now down to our boxers, our erections pressing through our shorts and rubbing against each other as we kept grinding. I placed my hand on his and he placed his hand on me and slowly jerked it off through his boxers. He guided me to stand on my knees, lowering his body through my legs and pulling my boxers down, fitting my cock into his mouth as he sucked on it slowly, building heat in his mouth that surrounded me like fire.
He looked up at me and let my cock just slowly fall out of his mouth, a small amount of saliva still attached to the head like something you only ever see in porn and you know they had to film like a hundred takes to get it just right. I shuddered at this; the eye contact he was giving me had been irresistible. I repositioned myself so that our hips were aligned again, and he leaned up to kiss me.
“I never noticed your eyes had two different colors before. They’re so beautiful.”
I blushed. I was self-conscious about this, but in my eyes, there were these big splotches of amber set in contrast against the steel blue.
“Thanks,” I nearly whispered back.
I placed my hand on his chest and started grinding against him. I have had sex before but not like this. This was all new, but I knew I wanted it. I didn’t know how to ask so I just started grinding up a little higher. Finally, I could feel his cock rubbing between my ass cheeks through our boxers. He understood what it was that I couldn’t ask for.
He leaned up and kissed my neck, kissing down to my chest. He reached out and grabbed my hand putting it on his boxers, placing his hand on mine. I leaned over so that we were laying sideways and we pulled them down together, now naked in front of each other. He leaned over, grabbing at my wrists this time and placing them firmly against the headboard. HE kept kissing as I kept getting redder. His hips started positioning themselves, and I lifted my lower back in kind.
The head of his cock was now rubbing against me. It felt like all sound had vanished except for our breathing, and my heart which was now pounding in my head. It beat steady but with a hard tempo that threatened heart failure. It pressed and I let out a soft gasp. Slowly it worked itself in, taking time and being as gentle as I had hoped he would.
I had fingered myself in the shower before and had been able to locate the prostate, so I was familiar with the concept, but this was way different than a finger. The size of his cock felt impossible. It was like a magician pulling out a long string from his coat sleeve, when would it end??
Finally, he had gotten all the way in and paused, allowing me to adjust. I relaxed as much as I could. The next thing I noticed after the fact that everything felt so much bigger was that I could feel the difference in heat between the parts of our body that were connected. I could feel his heartbeat grow faster and faster and was thinking about how he must be feeling my love heat in the same way. He could say the word and his wish would be my command.
Once I had adjusted, I looked at Dan and gave a little head bobbing nod. He started to pull out and push back in gently. I could feel it rubbing dangerously close to my prostate. This was a feeling so much better than what I had ever felt in my shower experiments.
I started to breathe heavily, not playing it up in any way or putting on a show, but genuinely in the moment and attuned to his body. He reached down and grabbed me, stroking in time to the gently bucking of his hips. Dan would lean in and kiss me everywhere that he could reach, and I leaned up, grabbing the back of his head and just held it to my chest as I breathed heavily into his ear.
I could feel a subtle change to his rhythm and understood what this change was. He was starting to push deeper and harder now, but at a slightly slower pace. With a few more deep thrusts he hit my prostate like a freight train, and I was pushed over the edge, my insides spasming uncontrollably and my cock emptying over my stomach. This made Dan push even harder, and with one last push, he started to cum.
I had no frame of reference for this feeling. It was like a warm liquid filling me, but it was more than that. It felt white-hot in my insides, and I felt like the warmth was taking over my whole body and making it glow. I let out little gasps with each splash of cum that shot its way into me.