This is an original story (M/M, anal sex) based on a real situation and real people from my past. Sadly, the sex is wishful thinking and pure fiction.
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A Room With A View
I married my high school sweetheart the summer after we graduated. She wife worked at the local mall on days and swing shift, and frequently on weekends. I was working a lot of low-skill jobs on nightshift.
We hardly ever saw each other. I was usually getting home around the time she was heading out, and by the time she got home, we'd have something to eat, watch a little TV and then I'd go to work.
We weren't having much sex before we got married and it didn't get any better after. We either had no time or she was too tired, but I also think she just wasn't into it.
I, on the other hand, felt desperate. I had the house to myself most of the time, so I could at least whack off as much as I wanted, but it was a poor substitute, and it was starting to mess with my sleep.
I finally worked long enough to qualify for medical insurance, but first I had to get a physical. I went to a local non-emergency clinic and went through the normal checks. I wasn't really expecting the hernia and prostate exams, but I tried act like they were no big deal.
I stood passively and coughed on command, while the doctor fondled my balls, and I realized it was the first time in over a month that someone else had touched my privates. It was really clinical, and I got through it without a problem. But then he had me lie on my side and he stuck a lubed finger up my ass. My dick shot up hard as a 2x4. It freaked me out the doctor just ignored it, finishing up his task, pulling out his finger, and sending me on my way.
I didn't know what to make of my reaction to the prostate exam. It made me wonder if I would react like that again and I decided to try my own fingers, but I couldn't get the angle or depth I needed. I found a hairbrush in the bathroom that had a handle that was about the right shape. It was the same length as my finger but a little bit thicker. Once I got it inside my butt, I realized that the thickness made it even better.
I jacked off with that brush handle up my ass, and I had a great cum. It became a regular part of my masturbation sessions, and it added some variety, but it still wasn't as satisfying as having real sex.
Short on sleep and short on sex, I was starting to get cranky and short tempered. I would try to talk to her about it, but it always ended up with us having an argument. I eventually stopped bringing it up, and I even found excuses to take my time getting home in the morning, just so she would be gone by the time I got there, and we wouldn't get into a fight.
We lived close to the airport, and there were hotels close by, most with coffee shops. To kill time, and treat myself, at least once or twice a week I would stop somewhere for breakfast.
The parking at one of the coffee shops was on the back, uphill side of the hotel. This put the parking grade above the ground floor, so when you pulled into a spot, you were looking down at the windows of first floor rooms. I didn't think much of it because it was early in the morning and the rooms were always dark and the shades were always closed.
Then, one morning, I pulled into a parking spot and realized I could see clearly inside the room directly in front of me. It looked unoccupied. The bed was neatly made, and I didn't see any luggage, but then I saw movement off to the side. I waited to get out of my car, not wanting to have my lights come on and startle whoever was down there.
A second later, a man walked into the room, probably coming from the bathroom. He stretched out on the bed, and that's when I realized he was buck naked. Still not sure what to expect, but now more than a little curious, I stayed in my car and watched.
The guy was about my age, well built, otherwise pretty average, but I saw right away that he had a really nice cock. It wasn't huge, but it looked like it was probably bigger than mine, and really nicely shaped. In a passing thought, I wondered how much different it would feel than my hairbrush, and when my conscious brain registered what I was thinking, my hands started to shake.
It was the mid-70s, and I knew a few people who were gay, but there was still a stigma attached to that. I had never even considered it as an option for me. So, imagining taking another guy's dick up my ass, and realizing that the fantasy was making my own dick hard, was totally unsettling. Despite that, or because of it, I couldn't look away.
I watched as the dude started masturbating, right there, in full view. I wondered if he even realized someone could see inside the room while he was jacking off... or if that was the whole point. So, I watched.
He never looked up at the window and he didn't take very long. I knew, from my own experience, that he was probably just trying to get off, stroking to a quick finish. I watched until he shot his load and then got off the bed, grabbing a towel and wiping down. A short time later, he stepped out of sight in the same direction he had first appeared, and I assumed he had gone back into the bathroom.
I started my car, backed out, and drove home, not even stopping for breakfast. As I pulled into my driveway, it was just in time to wave to my wife, as she was backing out on her way to work.
I went straight to my bedroom, stripped naked, and using my hairbrush, I jerked off to the most intense orgasm in ages. The whole time, I was picturing the guy at the hotel.
I was shaken by that experience, and it took me a week to stop stressing about it. But I couldn't stop thinking about it. If anything, it became an obsession. I masturbated almost daily, running through various scenarios for how that scene night have gone different, if I had confronted him in the hotel room.
I was telling myself that he had left the shades open because he was hoping someone like me would see him and do something about it. It was farfetched, but for a couple weeks, I stopped at that hotel every morning, parking in the exact same spot, but without a repeat of the previous show. I didn't even get breakfast. I would just wait in my car until I'd have to give up and leave. I finally assumed that the guy had been a guest and he was likely long gone.
Resigned to my old routine, I decided to legitimately stop for some breakfast. I pulled into the lot, taking one last look for a lighted room, but I only saw dark, shaded windows.
Inside, the coffee shop was almost empty. Early birds were already gone, and late sleepers weren't up yet. The waitress, a friendly middle-aged woman named Lois, poured my coffee, and left me to peruse the menu. I took a sip and looked around before checking the menu, seeing someone that almost made me do a spit take.
Coming out of the kitchen and stopping at the counter to talk to Lois, was the young man I had seen in the hotel room. The two exchanged greetings, and while he was standing there, I checked out the name tag that revealed he was Chad, Night Manager.
"Are you heading home?" I heard her say.
"Nope," Chad answered. "I have to cover swing shift tonight so I'm using one of the empties to catch some sleep."
"You better get to it then," she instructed.
He smiled. "It usually takes me awhile to fall asleep, especially right after shift."
"Well, you can watch some TV or something." She offered, trying to be helpful.
"Or something..." He chuckled and smiled again. Then he stopped to talk to the cook for a second.
Suddenly it made sense why I had not seen him again in the same room, even though he was still around, and he hadn't stopped his morning activity. He relocated depending on where there was an empty hotel room.
"Do you know what you want, honey?" The waitress woke me out of my stupor.
I looked up quickly. "Actually... I need to change my plans. I realized I need to be somewhere else. How much do I owe you."
"Well, you barely touched your coffee, dear, so don't worry about it."
"Thanks!" I said, still dropping a couple dollars on the counter.
By this time, the night manager had walked out of the coffee shop, and it took me a second or two to figure out which direction he had gone. I spotted the sign for the elevators and ran in that direction.
I slowed down as I approached, seeing Chad standing at the landing, waiting. He saw me approach and he smiled.
"Good morning," he offered.
I returned the greeting as the door opened and we both stepped inside. I then waited until I saw him punch a floor button.
"Where are you getting off?"
"Wh... what's that?"
He laughed. "What floor do you need?"
I probably turned two shades redder as I blushed. "Sorry... um... six." I answered, picking the floor he had selected.
"Well, that's convenient," he noted. "No extra stops!"
We both got off on the sixth floor and he headed left. I nervously considered what to do next, and decided to turn right, walking slowly down the hall while still trying to see where he was going.
He stopped at a room and went inside. I just stood there, trying to decide what I should do next. What if I did confront him? What would I say? What would he do about it? For all I knew, he would freak out and kick my ass, maybe even call the cops. Just because I got horny seeing him jack off didn't mean he was interested in trying something with me. Hell, I didn't even know if I had the nerve to try the "something" I was thinking about.
In for a penny, in for a pound. I steeled myself and made up my mind to follow through, but by then enough time had passed that I wasn't sure I wouldn't just be interrupting him in the middle of getting off. I wasn't sure if that would that work for me or just piss him off. Too late to worry about it, I was knocking on the door.
I could hear the creak of the bed and I knew he had at least gotten that far. A few seconds later the door cracked open, and he peeked out.
He looked confused when he saw me but then I saw some recognition. "You're the guy from the elevator? What can I do for you? Are you lost?"
I swallowed. "Not really... I was just... I..."
He looked past me, looking both ways down the hall. This revealed enough of him to show he was naked at least from the waist up.
"Are you okay?" He asked. "Is there a problem?"
"Umm... This is going to sound crazy but... I was here a few weeks ago and I was going to stop at the coffee shop, but I got distracted... by something I saw in one of the rooms."
"I don't understand," he said, clearly confused. "If you saw something inappropriate you should probably report it at the front desk. I'm off shift right now."
I chuckled. "I don't think you want me to report this," I explained. "I saw someone masturbating in one of the first-floor rooms. The shades were open. It was in clear sight."
"Oh! I'm so sorry that happened." He was still in night manager mode. "You can still report it, but I'm sure that guest is long gone by now."
"It wasn't a guest."
"It wasn't..." He paused. Then the light went on. "Oh damn! I am so sorry. It was dark out and the windows are like mirrors at night. I didn't even think about the shades being open..."
"No... no..." I interrupted. "Don't worry. It didn't bother me... well... not like that."
"Why... why are you here then?"
Time to commit. "For some reason, I couldn't stop thinking about it. It was... actually pretty hot... I guess. I just..."
"Are you gay?"
The question surprised me, but it shouldn't have. "No! I mean... not really." I had to think about it before I could clearly answer. "I never thought I might be until I saw... that. Now... I guess I'm not sure."
"So... I'll ask again. Why are you here... now?"
"I... I wonder if you... would want to fuck me."
I had already prepared myself for a negative reaction and I was ready to run off if I needed to.
"You want me to fuck you?"
"I think so... I mean... I do but I've never actually done it before..."
"Oh wow!" His reaction still seemed unclear, but he smiled. And then he opened the door all the way. He was completely naked.
He had one of those naturally athletic bodies. He was fit but it didn't look like he had to work at it. For some reason that was more attractive to me than if he looked gym built. I thought seeing him up close might put me off. It didn't. It also didn't take long for me to shift focus to his cock. It wasn't hard but the way it hung I could tell that it recently had been. It was slightly bigger and maybe even nicer than I remembered.
"You better come in," he said, stepping aside.
"Um... sure," I answered, stepping past him, into the room.
Now that I was in there, I was a lot less certain that I should be.
"You really never did this before?" He asked.
I shook my head. "No! Never even considered it. I mean, I'm married. It's just... we haven't been doing it... and I got curious after something happened to me... well... Let's just say I got curious."
"Guys staying at the hotel hit on me sometimes, and I've even thought about it, but... it always happens when I'm working. I sometimes think about it when I jerk off."
"So, you haven't done this either?"
"No, never."
I blushed, knowing how odd it was that I had confronted him this way, but he was still smiling. "Are we really going to do it?"
"If I heard you right, you are asking me... to fuck you. Are you even sure you can?" He asked, and added, "Or, that you'll like it?"
"Awhile back something happened that made me try... practicing... and I liked it."
He shrugged. "As long as you're sure. But I think we both should be naked to do this."
I blushed again, and then started stripping off clothing, revealing that my blush had been full body. Once naked, we stood facing.
"How do you want me to do it?" He asked, confusing me.
"Um... I want you to put your... dick... um..."
He laughed. "No, I got that part. Do you want to start on top? On the bottom?"
"Oh! I didn't even think about that," I laughed too. "What if we spoon just to start."
"Sure. That's cool."
We climbed into the bed. I rolled to my side facing the window, noticing the shades were open. For a second I felt panic, but then I remembered that we were on the sixth floor. I suppose someone at the neighboring hotel might get a good view, but I could live with that.
Chad took a second to lube his cock. He had the jar of Vaseline that he probably used to masturbate. Watching him stroke the greasy lube on his shaft, made me shiver. At the same time, it made me as horny as I had been in ages.
Climbing in behind me, Chad gave me one more chance to back out. "Are you still sure about this?"
"Fuck no!" I laughed, "But if we get this close and don't do it I'll go crazy."
"No argument," he grunted, moving in close and butting the knob of his dick against my tight butt pucker. "I don't really know what I'm doing, so let me know if I'm doing it right."
"You never tried anal with a girl?"
"Dude, I've never had... sex... before. This is literally my first time."
This guy clearly worked too much. No one who looked like him should still be a virgin.
"So, I'm your first?"
"Yeah," he sighed. "Is that bad?"
I thought for a second. "No. No, it's not bad. It's actually kind of cool... I just don't want to disappoint you. Is it okay for you if your first time is with me?"
"Dude! We haven't even done anything, and this is already the best day of my life."
I chuckled. "Well, we better do it then... just go slow."
He grunted agreement and settled into position. His cock spread my butt cheeks apart, but he didn't push right in. He just stayed like that, with his knob pressed against me. That was enough to let me relax until he slipped in slightly.
With that progress, Chad started shifting his hips so his cock would poke and then withdraw. Nothing happened fast, but I could tell that he was starting to go deeper.
When his cockhead popped through the tight ring of muscle, it was more surprising than painful. I felt a moment of panic, but Chad stopped pushing and held still again. He was noticeably bigger than the hairbrush handle, but it just made me more excited.
It was just the knob, but his cock was actually inside me. I took a moment to appreciate that. Then I pushed back and took a couple more inches of shaft inside me.
I knew it would be different than the brush handle, but having his cock in my ass didn't feel at all like I expected. When we started my dick had gone soft, probably from nerves, but as he started to move through my bowels, I first felt full like I had to take a giant dump, except it kept changing direction, like a slow pump that was quickly inflating my cock back to full erection.
"Are you doing okay?"
It took me a second to make my mouth work again, but the answer was clear. "Oh... god yeah! This is..." And that was all I could get out.
Chad grunted, finally hitting bottom. "Yeah... it definitely is!"
Chad wrapped his arms around me, like he was afraid I would try to escape, but I wouldn't have left for anything. His pace kept increasing and then, suddenly, quicker than I had expected, he slammed into me and held me close, and I felt his cock pulse with his orgasm.
"You came?" I asked, torn between being pleased that fucking me had made that happen, but also short of being totally satisfied by the experience.
"Yeah! Fuck... fuck..." He was still shaking. "I told you it's my first time. I couldn't help it. I'm sorry."
"It's okay," I tried to assure him.
"Can we keep going?"
"What?"
"Can I keep going?" He asked again. "I don't want to stop."
I realized that despite cumming, he was still hard, and moving again slowly. It felt amazing, but I decided I wanted more control.
"Let me get on top."
"Sure," Chad answered, pulling back so his cock slipped from my hole. I immediately missed it and needed it inside me again.
Chad rolled to his back, and I climbed on top, lowering myself onto him. The length of the drop was an intense and thrilling surprise to me, and by the time I landed it felt like he had gone even deeper that before.
"Oh jeez!" I gasped.
"You okay," he asked as his hands gripped my hips, preventing me from moving.
I smiled down at him. "How come I didn't know it would feel like this?"
He smiled back. "I hope that's a good thing?"
"If you let me loose, I can show you," I growled, really needing to feel him moving inside me. "Screw that sperm and eggs crap they told us in health class. They need to start teaching this shit."
He relaxed his grip but didn't completely let go. "I wish! There'd be a lot fewer teen pregnancies this way."
I lifted slowly and then dropped down hard. Then I lifted quickly and dropped slowly. It all worked, so I went to town, riding that shaft with everything I had. My hips became a blur as I fucked myself on Chad's ample staff. His knob would rub across my prostate, and I would feel a tremor run up my spine on each stroke. It was life changing!
I was racing closer and closer to the finish, not wanting it to happen too soon, but like Chad earlier, I knew I wouldn't be able to stop myself. Luckily, Chad intervened. His grip tightened on my hips, and gradually slowed me to a stop. By this time, I was gasping from the exertion.
"Damn, man!" He sighed. "I don't want to cum yet. I'm not sure I've got more than two in me. Please, slow down... slow down..."
I took the forced pause to catch my wind. "Sorry," I gasped between ragged breaths.
"Don't apologize!" He corrected. "This is so fucking amazing... I want to make it last."
"Yeah... me too..." Then I thought about why he was using the hotel room. "Don't you need to get some sleep at some point?"
"Trust me. When we're done here I'll sleep like a baby, but there is no way I am going to rush this. I may never get to do it again."
I didn't even have to think about it. "Oh... we can do this anytime you want."
We had both had some time to regain our bearings and we were finally ready to go. This time Chad decided to take control. He rolled over, taking me with him, and without ever pulling out he managed to get me on my back, with my legs spread wide.
Sounding nothing like the fresh-faced virgin he had started as, "Now you get to find out what it feels like to get fucked."
I shivered in anticipation, and then again, as his dick began its piston pattern inside my ass. I couldn't figure out if Chad was just a natural, or if it was just that his dick and my ass were a perfect fit, but it was as if everything he did felt perfect. I felt like I was balanced on the edge of cumming almost from the start, and the slightest shift in balance was going to throw me over the side.
His first orgasm now in the distant past, Chad was able to fuck me hard and fast, and then slowly, and then hard again, never breaking contact and seemingly with unlimited endurance. I, on the other hand, was a quivering mess. My hands crawled across his body spastically, feeling the flexing and knotting of his muscles as he lifted and fell, pounding his battering ram into me.
Then, with a soft cry, Chad's pace suddenly changed, and he plunged ball deep, holding against me tightly. That was the shift I had been waiting for, and my entire body suddenly clenched tight, my first blast of cum belching out across my stomach, and the second blast shooting clear past my head.
Almost immediately, I felt the soft pulse of his cock shooting into me again. Then Chad pulled back and resumed stroking into me fiercely, working to get the most out of his orgasm. Each plunge of his cock caused another convulsive discharge from my own and it felt like I kept cumming for as long as he was moving inside me.
By the time we both stopped, I was spray painted with the buckshot spatter of my spooge, and Chad's sperm filled me until it was dripping past the plug of his cock.
He dropped against me like a heavy blanket, and we just lay there, both needing the time to catch our breath.
"Thank you so much!" Chad finally gasped.
I could feel his cock softening inside me, and I knew I would need it there, hard, again. "No... thank you," I answered. "You could have chased me off, and this... would have never happened."
He nodded. "Yeah... I wasn't sure what to do when you showed up. I think I made the right choice."
"Definitely."
Reluctantly, Chad lifted off me and his softened cock, slipped wetly from my battered hole. I felt a slight twinge of pain as my sphincter fought to close up, but I would have gladly taken him again, if he wanted.
We showered together, having some fun washing each other down. Then I got dressed to go home, while he got the bed ready for sleep.
"So... you said we could do this anytime I want." He reminded me, as I started to step out of the room. "Did you mean that?"
I grinned. "To be honest, I was worried I would have to stake the place out to make sure we did this again."
He grinned back. "No need to stake it out. I definitely want to do it again. Just so you know... I can hold a room anytime I want to. I'm just..."
"What?"
"I'm just not sure you'll want to do it as much as I do."
Turning out the light before leaving and closing the door, I said, "I guess we can find out tomorrow."