The rest of the weekend passed by quickly and before I knew it, I was back in the office sorting through contracts, attending meetings with clients, and attending meetings with the staff and Jason. Jason acted no different around me and, really, why would he? My body, however, reacted differently. I was following Jason’s instructions and wasn't jerking off. Because of that and because my hormones were as confused as me, I was like a pubescent teen again. Popping erections at the most inconvenient times, especially when sex was the furthest from my mind.
Thursday rolled around and I was in the break room heating up my lunch when Jason came in. He quickly moved up behind me, rubbed my ass and nuzzled my ear. And then, just as quickly, he left, without a word. Thankfully the break room was empty as my cock had immediately hardened and was tenting my slacks. I quickly sat down and began eating my lunch, willing my erection to go away. I went home that night and began researching how to deal with anal sex for the first time. My research didn’t do much to alleviate my nervousness and apprehension but, I at least had a little bit of knowledge now, as far as what to expect.
Saturday arrived. It had been a sleepless night, not because of nerves so much but I had had a series of erotic dreams that left me panting and sweating each time I woke up. They also left me with wet shorts from the pre-cum I would leak out. First order of the day would be to air out my bedroom and put on fresh sheets. That taken care of, I made coffee, scrambled a couple eggs and sat on my balcony while I ate and mentally prepared myself for Jason’s visit.
The day passed quickly and at three o’clock I hopped in the shower and cleaned off. Once out and dried off, I unlocked the door to my condo and went to my bedroom and waited. Right at four o’clock, I heard the door open and Jason called out to let me know he had arrived. I rolled over, ass up, head on my pillow, eyes closed and practicing my deep breathing.
Jason moaned as he entered my bedroom and started removing his clothes. I felt him get on the bed, move behind me and lay across my back, his head next to mine, the smell of his cologne filling my nostrils. He begins to nibble my ear, and I moan in spite of myself.
“You been saving your load for me Ethan?”Jason asks, his hands moving under me, finding my nipples and rubbing them. I moan and nod yes. “Good boy”, Jason replies. He then begins kissing and nipping at the nape of my neck. I can feel his hardness snaking its way between my legs, the shaft of his cock beginning to tap against my balls with his pulse. I moan and shudder as my own cock hardens.
“I'm going to make you feel so good Ethan. You're going to love being filled with my cock. Are you nervous Ethan?”Jason asked as he moved down my back, his tongue tracing circles along my spine.
“Yes and not looking forward to the pain”, I respond, moaning as his hand grips my cock, rubbing my pre-cum over the head and down the shaft. Jason’s mouth is now at the top of the crack of my ass, his tongue beginning to slide in.
“I'll go slow Ethan. I want you to enjoy this and you will by the time we are done. Fuck, your ass is so beautiful. I love how your cheeks naturally part, showing me your virgin hole”, Jason pants as he swipes my cockhead with a finger and rubs the pre-cum into my hole. I jerk at his initial touch, my hole twitching at the unfamiliar feeling.
Jason reaches between my legs and pulls my cock back towards him, his mouth engulfing the head of my cock, his tongue running circles over the head, lapping up my steady flow of pre-cum. I moan and pant and shudder, already on the precipice of orgasm. Jason releases my cock head, and starts licking and sucking on my balls.
“Oh god Jason! What are you doing to me?”, I cry out, “Feels so fucking good!” He then begins licking and nibbling my balls, up my taint and stopping just before he gets to my hole. I buck and grind my hips on his tongue. My cock jerks, pre-cum streams out, soaking the bedspread below me.
“Yeah, that's it Ethan. Let yourself go, enjoy this.”, Jason pants before he starts eating my hole out. His tongue circles around the outer rim of my hole several times before he swipes it across, causing me to cry out in delight and buck my hips back on his tongue. He does that a few more times before he sticks the tip of his tongue in my hole and semi penetrates me.
“Oh fuck! Holy shit, mmmm…”, I cry out as the tip of his tongue enters me. This feeling is incredible and my senses are overloaded with the pleasure of it all. I pant, moan and writhe and Jason continues to tongue fuck my hole. He then spits on my hole and starts rubbing that in with his index finger, slipping it in slowly, waiting for my reaction.
“Damn it Jason, what are you doing to me? I, I, oh fuck. Yes, yes, finger me, eat me, oh fuck”, I pant and moan.
I buck and grind and fuck myself on Jason’s finger. He removes his finger, spits again then slides two fingers inside me and starts fucking my hole with them. Twisting them, sliding them in and out, preparing me for his cock. I shudder and shake as I continue to grind and buck on his fingers. Never in my life could I have known I would react like this. Never in my life would I have guessed that this part of my body could be stimulated like this and feel so good.
Jason removes his fingers, sits up and reaches for the lube bottle that I had placed on the nightstand. I hear the cap pop open, snap shut and feel the cold wetness against my hole as Jason begins to lube my hole up. He then moves up and lays on my back again, his mouth at my ear, the head of his cock at my entrance. The time has come and I instantly tense up.
“Relax Ethan, just relax. Breathe for me, come on. Deep, calm, breaths, in and out”, Jason softly says in my ear. Nipping my ear lobe as I feel the head of his cock start to part the ring of my hole. My ass clenches shut, barring his entrance. Jason patiently waits, gently applying more pressure, distracting me by toying with my nipples and kissing my neck and ears.
“That's it Ethan, just relax, let me in. Gonna make you feel so good Ethan. Just open your hole, let me in. Just relax.”, Jason whispers.
As soon as he says that, the ring to my ass relaxes and the head of his cock slides in and with it, the most intense pain I have ever felt. I immediately try to crawl out from beneath him, telling him to take it out, it hurts too much. Jason keeps a firm hold on me, the head of his cock staying buried inside me, regardless of how much I’m fighting to get away. Jason manages to slowly slide a little more of his cock inside me. The pain begins to subside, slowly replaced by a burning, tingling, tickling sensation. Before I know it, Jason has the full length of his cock buried inside me and he’s gently rocking his hips side to side. My cock, which was rock hard, has deflated through all of this. But as pain begins to be replaced by pleasure, it starts to slowly plump up again.
“Feel that Ethan? I’m all the way inside you now. Oh baby, you feel so good. Your walls are like satin wrapped around my cock. Yeah, oh you feel so good. Doing great Ethan, just keep breathing, keep relaxed.”, Jason coos as he sits up and slowly begins sliding his cock out.
Jason slides his cock back until just the head is inside me, he then slowly slides back in. His cock head gliding over my prostate, making me moan and buck as it does. Jason smiles to himself as he knows he's found my pleasure center and he starts moving his hips faster, grinding them, focusing on hitting my prostate.
My half hard cock instantly springs to life and I begin bucking my hips back on his cock as he slides in me. I cry out, moan, pant and curse as Jason continues to increase the pace of his fucking me.
“Jason, oh fuck. Feels so good! Fuck me! Fuck me hard Jason!”, I shout.
“That's it Ethan, take it! Take my cock! Do you like this? Yeah? Like me slamming your hole with my cock?”, Jason says as he continues to pound my ass with his cock. I moan, buck, writhe and pant as I continue to beg him to fuck my ass. Jason and I begin this dance of moving together, pushing and pulling as he rides my ass for what feels like an eternity. We moan and pant and cry out as each of us rush toward our orgasm. I am amazed at how good this all feels and how good it continues to get as Jason finds new techniques to grind and pound his cock in to me.
“Get on your back, I want to see your face when you cum”, Jason says as he pulls his cock out of me and I flip over on my back. Jason drapes my legs over his shoulder and slides his rock hard cock back in my wet hole. This position gives me a completely different feeling of his cock as he slides it back into me. I moan and cry out as I feel his cock start its constant stimulation of my prostate in this position.
“I want to see you cum Ethan. Want to see that cock shoot!”, Jason growls as he starts fucking me again, hard and fast.
“Yeah Jason, oh fuck. Mmm… you feel so good inside me. Make me cum Jason, gotta cum!”I pant and moan.
My cock is streaming pre-cum, making a puddle on my stomach. I rub my hand through it, lubing up my cock and starting to jerk off. Jason bats my hand away from my cock.
“I want to see that cock shoot hands free. Ethan, I’m, I’m, getting close. Cum with me! Shoot it! Let yourself go!”Jason pants.
I nod and moan as he continues to fuck me. Soon, I begin to feel an odd sensation. A pressure, like you get when you have to urinate, begins to build inside me. It then starts to move to my balls and surround the base of my cock, My cock gets even harder and begins flexing and bobbing up and down.
“Jason, I, I think I'm going to cum”, I say.
“Let it go Ethan, cum for me! Gonna fill you up with my load Ethan, gonna…. Oh fuck, oh fuck, here it comes!”Jason screams as he slams into me and begins filling me up with his cum.
I cry out as the first rope of cum shoots out of my cock and lands on my chin. Two more ropes shoot out and splatter my chest. I can't speak or breathe as my orgasm hits and takes hold of me. I have never come this hard and the amount of cum now flowing out of my cock, coats my pubic area and begins to run down the crack of my ass.
Jason watches me buck and shudder, my eyes rolled in the back of my head, as my orgasm crashes over me and ebbs, his cock still in me, still twitching every now and then. I finally begin to come down and he pulls his cock out of me, his cum dribbling out of my ass. He lays down next to me, both of us panting and sweating profusely.
“That was mind blowing”, I say, my breath beginning to return to normal. “Whats next?”, I ask, as I run my fingers through the cum on my chest, rubbing it into my skin.
“Mmm… you did great Ethan! You need a few days after this to sort through it, and you will sort through it. Then we'll discuss what's next.”, Jason replied, matter of factly.
I nodded, closed my eyes and drifted off to post orgasmic sleep. I woke up, glanced at the clock to see it was midnight. I was still in the same position on top of the bedspread, my cum now having dried to a crust. Jason was gone and there was a pleasant ache in my ass. I turned on the bedside lamp, grabbed my bathrobe and headed to the living room. Jason had locked the door on his way out. Hungry, I made a sandwich and sat down to eat it.
“Fucking amazing. Welcome to the world of enjoying cock Ethan.”, I said, my cock beginning to rise.
