Soon, he completely drained my balls. My cock slipped out of his lips. I collapsed back on the bed and proudly declared. “Holy fuck!”
Jake laughed and said. “Not bad for a man at my age.”
I joined in and chuckled. “You fuck like a spring chicken.”
“I think I’m more like a lusty goat,” he replied with a smile. Then, he leaned in to give me a kiss. I tasted the tangy flavor of semen on his lips. I found it to be to my liking. “Now that I’ve lubed you up, it’s your turn to suck me.”
He punctuated his statement by sitting on the edge of the bed and spreading his legs. I immediately knew that he wanted me to suck him off. I may have been frightened at the proposition of fucking Jake but I had finally come around to it.
Without hesitation, I moved between my landlord’s legs. It helped that I had picked up a thing or two from the blowjob he had given me. I got a good look at Jake’s cock. It was much bigger and thicker than mine. It was practically a small maypole made of flesh.
Despite my inexperience, I remembered Jake’s motions and began by gripping the base of his shaft. I took down the foreskin of his cock and unsheathed its bulbous head. I brought my face closer and closer to his erection. I could already smell the musty aroma of his privates. It was almost too overwhelming.
Whatever hesitation I felt was gone, I leaned forward and swallowed his cock. I immediately tasted the salty tang of his skin. Jake groaned with approval as he instructed me. “Yes that’s it… take it slow. It’s a marathon, not a sprint.”
Heeding his words, I slowed down and tried to take it one step at a time. Well, I had to take his cock in one inch at a time first. His shaft seemed endlessly long. I focused on teasing the sensitive skin of its head. I knew I hit the jugular when Jake let out a lengthy moan. “Oh… you’re doing great…”
I listened as he directed my actions. It was quite an educational experience. I was learning more about how a cock worked from Jake than I did from my high school biology class. I was getting better at it by the second. Soon, I felt the rumblings of a climax brew in his balls. It prompted me to swallow more of his massive phallus.
Seeing that I was taking charge, Jake decided to relax and let me do the work. Indeed, I had gotten a hang of what to do. I knew where and when to suck him. I concentrated on teasing the soft underbelly of his cock. There were a number of sweet spots I could hit there with my tongue. I couldn’t swallow the entire length of his prick but I could still bring him to orgasm.
The taste and smell of his cock was intoxicating. Unlike me, Jake wasn’t going to go off anytime soon. The man was a veteran when it came to sexual encounters with men. He didn’t have my virginal eagerness. If our roles were reversed, then I would’ve already blown my load and gone soft by now. It would take quite a bit of my skill to get him to go off.
Not that I wanted him to climax just yet.
Thankfully, Jake had similar thoughts. He took my mouth off his raging erection with a sense of urgency. With desire in his eyes, he stated. “Sarah, I need to fuck you!”
My mouth had lit the flame in him and stoked it. Now, my ass was going to finish the job. “With pleasure.”
Chapter 5
Not sure about how to begin, I mounted the bed and waited for Jake to take charge. The man had probably fucked countless guys like me. The only question was whether or not his cock would fit inside my virginal asshole.
After my blowjob, his prick was as big as a small tree branch. Even a woman’s pussy would have difficulty taking that colossal cock inside. After lubing it up with my saliva, I still knew it would be a very tight fit.
Before I can even begin to comprehend a strategy, the doorbell rang and interrupted my thoughts.
“Sorry, business calls,” Jake laughed, almost looking apologetic. For a second, I forgot that he was supposed to be a mild-mannered landlord. Hell, I forgot that I was fucking him to get out of paying rent. “I’ll be back in a minute. Don’t go anywhere.”
Like an obedient child, I sat on the bed and watched Jake put on a large robe. He looked like he was just about to take a shower instead of fuck another man. When he heard the doorbell ring again, he rushed out of the room.
I suddenly felt conscious about my nudity. I had exposed both my body and soul to Jake. I was doing things with him that I never thought I was capable of. I wanted to cover myself up with bedsheets but there was little point to it. Jake would be back at any minute.
I tried to eavesdrop on what was going on outside. However, he was too far away. I couldn’t make out a single word or identify the other speaker.
Letting curiosity get the better of me, I left the bedroom and tiptoed towards the entrance. Hiding behind a doorway, I heard the voice of another man. It sounded oddly familiar.
I inched closer so that I could get a better view of the conversation. I saw Jake standing at the doorway speaking to another man. He blocked the identity of whoever was on the other side but I recognized the voice. I leaned in to identify the speaker.
My heart skipped a beat when I saw that it was Craig.
“I’m afraid it’s not a good time for our usual… conversations,” Jake said. I guessed that Craig was one of his lovers. I wondered how long this had been going on. I was also curious to know if Jake had asked Craig to send me his way. “I’m currently busy with another appointment.”
Craig smiled. “Who is it? Anthony? Mark?”
Jake chuckled. “I have many tenants to attend to. I’ll let you know when there is an opening.”
The two bid each other farewell as I headed back to the bedroom. My mind was reeling at the revelation. Jake was fucking a number of his male tenants.
It explained why the rents were so low. Jake wasn’t here for money. He was using his affordable housing to create a harem. I probably wasn’t the first man to be in his debt.
It also explained why so many of the apartment suites belonged to young male bachelors. They were the perfect target for Jake. Men like me had more money than sense. We also didn’t have families and would be interested in a special arrangement with their generous landlord.
The sound of Jake entering the bedroom broke me out of my thoughts. “Hope I didn’t keep you waiting for too long, Sarah.”
I decided to play it cool while probe him for more information. “I didn’t mind. Was it another tenant?”
He climbed back onto the bed. “Yes, but not for the type of business I usually conduct.”
I wondered if he was grooming me to be another one of his pets. In all honesty, I wouldn’t mind if it meant I didn’t have to pay for rent. Besides, I was enjoying being dressed up like a woman. “Anyone I would know?”
He laughed. “Maybe. He’s one of my other… girls.”
I giggled playfully. “I thought I was your special girl.”
“You are special,” Jake replied. “I spent a very long time preparing for today.”
He must have been planning on ensnaring me the moment I applied for his apartment complex. It explained why he had been so forgiving over my missed rent checks. Jake wanted me when I was at my most desperate. Most landlords would have kicked a guy like me out after seeing how much I had fucked up. “I see…”
Jake slid out of his robe. “Now, let’s get back to business.”
I nodded and put the various questions I had in the back of my head. I could worry about Jake’s master plan later. Now, I wanted to concentrate on the ass fucking I was about to receive.
Jake shared my thoughts as he rummaged through a drawer. “Since you’re new at this, I’ll lube you up first. Don’t worry, you’ll love it once you get used to it.”
He took out a small battle of lubrication. My landlord applied it to his massive erection. Then, he went on to lube my asshole with a finger. I felt a shiver down my spine as he probed. It felt strange having just a finger inside of me. I couldn’t imagine what it would be like to have his massive cock in me.
I didn’t have to wait long to find out.
With a hand grasping the base of his erection, Jake entered my tight nether orifice. I gritted my teeth as a bolt of pain pierced me. My lover was in his element as he thrust forth. “Damn you’re tight!”
My ass cheeks clamped down on his prick like a mousetrap. I let out a shrill yelp. “Ah…!”
It didn’t deter Jake from entering deeper into me. The head of his cock probed and stretched me. I groaned as she explored my asshole. I didn’t how he was able to shove that pillar of meat deeper into me.
Once he got used to the pressure, Jake began fucking me with a steady rhythm. My eyes nearly rolled back into my sockets from the pleasure I was feeling. Whatever pain I felt faded away as I started to enjoy getting ass fucked.
My landlord was surprisingly slow and methodical. I knew that he was no stranger to fucking guys but he was acting like a real pro. I felt as if everything was under control with a cock battering my ass.
After agreeing to the deal, I wasn’t expecting my body to love a good ass-reaming. I spread my legs wide and invited his cock to penetrate me further. I wanted him.
Jake may have been old enough to be my father but he fucked like a young bachelor. Time and age hadn’t slowed him down one bit. He was a much better fuck than any of the girls I had been with. My body felt like it riding an escalator up to heaven.
“Fuck me, Jake!” I chanted, grinding my erection against the bed. I felt his balls slap against my ass whenever we fucked. “Fuck my ass raw! Fuck me harder!”
While my lover had complete control over his movements, there was no grace to what I was doing. I felt like a prey animal who had been caught by a predator. We were beasts of the wild coupling together. My unrefined instincts guided me as I submitted to my ass pounding.
On the other hand, Jake hadn’t even broken a sweat. The man had a bottomless appetite for my ass. I could only imagine what he was experiencing. If the look on his face was any indication, then he was having just as good of a time.
Together, we rocked back and forth. It was a rhythm as natural to me as my heartbeat. We worked together as one. Our movements blended together perfectly.
The toll of our lovemaking made its mark on me. My breathing grew ragged and sweat dripped down my body. I felt like I was toeing the edge of a precipice. One small push and I would fall into the abyss.
Jake’s hand gripped my shoulders as he railed me. His body pinned me down with its weight. I couldn’t move even if wanted to. I was just fine letting his flesh and warmth engulf me. I felt the heat of his muscles from each passing motions. I sensed the delight whenever he let out a groan. From the quivering in his prick, I knew he wasn’t far from an orgasm.
I wasn’t far behind either.
Jake pounded me into submission. He ground his hips against me as he probed deeper. I didn’t want it to end but the excitement was too overwhelming. I felt his cock stir inside of me.
It turned out that I was the first one to achieve climax. I let out a cry of passion as an explosive force rocked my shaft. “Ah… I’m coming, Jake!”
My flesh tingled with a strange electric sensation. My eyes saw bright spots as if I had looked straight into the flash of a camera. Jake joined in on the moaning and pressed his body against mine. “Come for me!”
The man broke out into a sprint.
Together, our mutual orgasm wracked our bodies with bliss. I was at Jake’s complete mercy as his cock erupted inside of me. I felt the warm splash of semen deep within my ass. It felt like my body was being crushed by a phantom force. I regained my breath and yelled. “Oh my fucking God!”
Down below, I felt the bedsheets grow wet and sticky with my climax. I wanted to move off the dampness but Jake had me pinned down. The man furiously pumped his cock in and out of me. His shaft still sprayed its precious cargo inside my ass. By now, he had splattered every inch of my asshole.
It was an absolute typhoon of sexual pleasure that drowned my body. I never wanted it to end. I saw a flash of bright light as I endured one languid thrust after another. However, the novelty of the encounter and Jake’s skill meant that I was completely drained of energy.
His prick sprayed a milky stream of semen against the walls of my ass. For an easy-going landlord, he knew how to fuck like a porn star. Soon, the blast of hot come subsided. I had milked his balls dry.
Slowly, our explosive climax began to fade. I felt fatigued as if I had swam across an entire lake. Jake looked completely spent as well. His seemly endless thrusts had finally come to an end. He rested his head over mine and planted soft kisses upon my neck. We were both utterly spent. Our bodies automatically snuggled together as we gathered our breath.
My landlord tenderly stroked my hair before planting a kiss on my face. “Sarah… Seth, you were amazing.”
I giggled as I basked in the aftermath of my orgasm. “Your cock is amazing.”
“My door is always open,” Jake said with a smile. More to his point, his bed would always have a spot for me. It was a tantalizing idea. For now, I was content to savor our sexual encounter. “You’ll never have to pay rent again.”
“I’ll keep that in mind,” I said, kissing him back. “See you around.”
An hour later, I went back to my apartment suite.
I was finally debt free.
After a good sex session, I was content to shower and relax. I never felt happier since I had arrived at this apartment complex. I had a spring in my step and I couldn’t help but go outside for a walk.
Everything about the place seemed brighter and better than I remembered it. I no longer sulked like the broke tenant I used to be. I took a round across the perimeter and ran into a familiar face.
It was Craig.
“Hey, Seth,” he said cheerfully. There was an all too knowing smile on his face. “It looks like you came to an understanding with Jake. I told you that he was a very flexible man.”
I returned his smile. “Well, I was the one being flexible… if you know what I mean.”
“I’d like to see it firsthand,” Craig replied. My cock stirred at the thought of a threesome. “How about you join me when I go see Jake during my next… appointment?”
I didn’t hesitate. “Count me in.”
Chapter 1
I heard the waves crash against the rocks as I strolled along the countryside. In the distance, families frolicked in the cool ocean water. The bright Hawaiian sun shone brightly with nary a cloud in the sky.
I had spent months planning this vacation. My friends were surprised that I had taken some time off. It was a bit of a surprise to me as well. Then again, I was just as methodical at planning a trip as I was at doing work.
You see, I had always been a workaholic. I was paid a generous six digit figure but my boss always said he got more work out of me than he paid me for. I didn’t even mind working from home during the night. Tearing myself from my desk and work phone was a herculean task in itself.
With my boss’s encouragement, I decided to make use of those vacation days I had stacked up over the past year. If I didn’t know any better, then I’d have to say that he wanted me out of the office. I couldn’t blame him since I had been gloomy over the past few weeks. My boss and coworkers wanted me, senior executive Alan Brown, out of their hair for a few weeks.
In any case, I didn’t have to pay much for the trip. Over the years, I had built up quite a number of frequent flyer miles and hotel credits over the years. Nothing beat an all-expenses paid trip to Hawaii.
So why wasn’t I happy?
The answer had nothing to do with the setting. Indeed, the sun illuminated everything with its yellow honey warmth. Most men would be content sunning themselves on the beach and feasting on freshly made poke and other seafood dishes.
Instead, I was coming from a recent breakup. It wasn’t like I was madly in love with the girl I had left. We actually had a number of fights because of how I had spent so much time working. I was never around for her.
It made me realize I had put work above every
thing else in my life. Sure, it paid big bucks but most of my peers had a family to come back to. I wondered if I could ever have a normal, loving relationship. It put a damper on my vacation on this beautiful island.
Well, archipelago if you wanted to get technical.
I didn’t care much about socializing and enjoying the night life here. I wasn’t eager to jump straight into another relationship just yet. I could never find the right girl or establish a comfortable romantic rhythm with them. The Hawaiian atmosphere hadn’t put me in a mood for intimacy. Besides, I would have to leave in a few weeks anyway.
I spent most of my days hiking. Other times, I went snorkeling or learned about the islands’ ecology. Engaging in a physical activity kept my mind off of my dismal romantic life.
The Trans Ultra Collection Vol 3 Page 24