6. Danny
After that first time, Jeff couldn’t get enough of my ass. He wanted to fuck me every chance he got, although we had to wait for a few days after the first time, because my hole was too sore to withstand another such assault. Even my parents noticed I was walking funny and winced whenever I sat down, so I had to make up some lame excuse about hurting my back in the gym.
“What’s with the sudden interest in working out?” my Dad remarked, being that ‘going to the gym’ was my alibi for all the time I spent at Jeff’s. If I didn’t start looking like The Rock soon, he’d get suspicious for real.
But I was too happy to care. I went back to sucking Jeff’s cock the very next day, both of us biding our time until the main course was on the menu again. As soon as I felt sufficiently recovered, I told Jeff I was ready to be fucked again. He wanted to wait a few more days, considerate as he was, but I insisted—the look of pure lust in his eyes at the prospect of fucking my ass again was plain as day.
This time he was very gentle; after a lengthy fingering session, he fucked me slowly for almost an hour, crouching behind me, only picking up his pace at the very end. By the time he came, my ass was so accustomed to his cock that it felt like it was made to hold him inside, my sphincter stretched for him, my rectum reshaped to his cock’s image. There was no pain anymore, no discomfort. Only the absolute, heavenly pleasure.
For the next two weeks, Jeff kept fucking me in every position he could think of: spread across the kitchen table, sideways on the couch in his living room, standing up and nailing me against the wall, soaped up in the shower, sitting in his armchair while I was riding him, lying on top of me in his bed—you name it, we did it. A single day couldn’t pass without his cock shoved inside me, often more than once. His virility and stamina put even my own libido to shame. And the best of all, he didn’t even need to hold back anymore; he could be as rough and wild as he wanted. In fact, the harder he fucked me, the more I loved it.
The only thing that would make it even more perfect would be if he bred me raw, but he insisted on using condoms. After commenting once that I missed his cum, since he always finished inside my ass these days, he compromised by pulling out before the climax, tossing the condom aside, shoving his cock in my mouth, and shooting his load down my throat like he used to in the beginning. I think he got off on the image of his cock going from my ass straight to my mouth, and that became the new standard afterward.
There was one other thing, though. It started bothering me a little that he always fucked me with his eyes closed. Usually, he preferred positions where we didn’t face each other, but on those rare occasions when we did, I studied his flushed, sweat-covered face, loving the look of pure bliss on it. But he kept his eyes shut for as long as he could help it, determined to avoid the truth of whose hole he was fucking.
On the other hand, he started cuddling with me after sex instead of sending me home as soon as he came. We began spending more and more time together not fucking, simply cuddling on his couch in front of the TV, sharing meals, or lounging in his large bed wrapped in each others arms, just talking between our lovemaking sessions. It was so easy to talk to him; even though he was much older, he never once talked down on me or acted condescending. His maturity and experience gave him a warmth, empathy, and patience I’d never found in guys my age.
He asked about my time at Princeton, my plans for the future, my hobbies and stuff, showing an interest in me that honestly took me by surprise. He also opened up a little, sharing bits and pieces from his own life, which is how we discovered we had more in common than we thought—I was majoring in Architecture and Engineering, and he was running a successful Architectural firm here in Stamford. He even offered to set me up with some internship positions after I graduate.
Yeah, if it isn’t obvious enough, I’m just gonna come out and say it: I was falling in love with Jeff. I’d been falling in love with him since the first moment I tasted his fat cock, but now I was completely head over heels. Rationally, I knew it could never be and he didn’t feel the same way about me. But I quashed that thought, repressing the truth so as not to get depressed. I didn’t want to spoil what we had, and if I confessed my feelings for him, it could mean the end of our little clandestine affair. And the thought of losing him scared me shitless.
I had no right nor reason to complain. I always knew what I was getting into, and the rules of our deal were simple—it was only sex; nothing more, nothing less. He already gave me more than what we’d originally bargained for, fucking me with more passion, diligence, and attention than any boyfriend I ever had. If I could ask for one more thing, that would be for him to kiss me; just once, to meld his lips with mine, to shove his tongue in my mouth and let me taste him that way.
Was it possible? Could it happen? We were already pushing the limits of our agreement, and despite being grateful, I was also becoming increasingly greedy. And it seemed that Jeff was opening up for more and more kinky stuff that he didn’t think he’d like at first but was now curious to try. He truly shocked me one time when I felt his tongue on my hole. He was behind me, preparing me for his cock, when all of a sudden, his mouth replaced his fingers, and his tongue started lapping at the puckered flesh. My body shook in ecstasy as I whimpered for him to keep going, and he did, he rimmed me until I was close to cumming. Then he rammed his cock inside, hitting my prostate, and I came like a fucking geyser.
So I kept my hopes up, knowing that one of these days something had to give. And then it did. Just not the way I was imagining it.
It happened one sunny August afternoon, when Jeff fucked me on the couch in his living room. I was on my back, legs on his broad shoulders, while he pressed on top of me, his cock buried deep inside my hole, pistoning in and out. We were nearing the climax, lost in the heat of passion, blind to everything but the friction of our bodies. His eyes flew open, locking with mine, and he saw the look of joy and surrender on my face. I licked my lips, moaning his name. He lowered his face closer to mine, his hot breath on my cheeks, his beard tickling my chin, his lips almost brushing mine…
“Oh, for fuck’s sake, Dad!” a voice behind us pierced through our daze. At that point, I was cumming so hard I could barely register it.