Daniel Cashes In His Chip

Daniel Cashes in His Chips

"What's it like getting fucked?" Asked Daniel at one of our regular Wednesday post-work meetings.

The two of us were sitting at the usually crowded Mitre Tavern in Melbourne's CBD. I took a sip of Kilkenny Ale and considered my response.

"Speaking from my own experience, it's not unpleasant," I replied, recalling my previous experience, which was six or so years ago.

"You don't like it?" Asked my surprised friend.

"It's not that I don't like it," I responded, "Taking a dick in my arse doesn't get me off like it does for other men and women."

"Oh," Answered a bemused Daniel, "But some men get off on it?"

"Those guys I've fucked have come hard," I said, "But I don't get the same intensity as they did."

"When was the last you took cock up your butt?"

I gave Daniel a brief synopsis of my relationship with the young student Thomas back in Western Australia. While I tended to be a top and Thomas was a committed bottom, we regularly switched for variety.

"He sounds like an awesome lover," Daniel smiled, "What happened between you two?"

"We were only casual fuck buddies," I replied, growing hard thinking about his supple body and insatiable appetite, "And he found himself a hot young stud to fall in love with."

"Disappointed?" Asked Daniel with growing interest.

"Not really," I replied, draining my glass, "He was the last man before we met."

"That was purely happenstance," He said before rising from the table, taking the glasses back to the bar and ordering another round.

Daniel was quite the random find. Bored and frustrated one stormy Saturday evening, I visited a sex shop in the city to jerk off to some porn vids. Not finding satisfaction with the hetero genre, I paid admission to the gay cinema, and while the on-screen action was equally uninspiring, I had caught Daniel's gaze.

I had not considered sexual encounters with men since Thomas and I went our separate ways, but there was something to Daniel that tickled my fancy. Physically he was attractive, well-dressed, educated, and well-to-do. He was curious about his bisexual proclivities despite being in a happy marriage. Given his wife was bisexual and frequently indulged, that passion openly led Daniel to explore his interests. While his wife was open about her extra-marital activities, Daniel was yet to disclose his own experiences with me, which bugged his conscience.

The two of us had settled into a comfortable routine of weekly Wednesday post-work catchups that resulted in some alleyway action and fortnightly Saturday evening sessions at the sex shop where we initially met. Daniel was hesitant, and our sexual activities were confined to heavy bouts of mutual oral pleasure. Mostly, he would suck my cock and swallow my come, interspersed with growing confidence at rimming my arsehole to heighten my orgasm. Occasionally, I would return the favour, but Daniel seemed not to want to progress with anal penetration. The fact that he was broaching the subject offered hope.

"Here you go," Daniel said, placing two refilled pint glasses on the table, "Cheers."

We took hearty sips from our glasses, and I waited for him to restart the conversation.

"So," He said nervously, "Does it hurt?"

"Does what hurt?"

"Getting fucked anally."

I took a second before replying and compiled all the responses to the same question I've asked from those partners that took my cock up their butts, both male and female, and combined it with my own experience.

"As long as you don't slam it in there unannounced and use a bit of care and lubrication, it's a pleasurable experience."

"But you didn't like it!"

"I did not say that," I replied sternly, "It's not unpleasant, but being fuck up the arse doesn't bring me off in the way it has for the others."

"So, others -- men - orgasm from anal penetration?"

"They have," I confirmed and related the story of Lyndon and his university pals that engaged in gay sex whenever they were unsuccessful in scoring pussy. When I fucked their arses, their cocks would frequently ejaculate without any masturbation. I was jealous of their ability to squirt come just from having their shitters ploughed. For me, I jerked my cock to orgasm as my rectum was filling with hot man seed because the act of penetration alone did not do it for me.

"Interesting," Said Daniel, whose crotch was clearly bulging.

"Why do you ask?"

"Been thinking about it more and more."

"Thinking about what?" I fished.

"About being fucked in the arse," Daniel replied, blushing, "Being fucked by you."

"And?"

"And," He exhaled, "I'd like to try it."

My cock was raging now at the thought of Daniel going all in. I anticipated his next question by asking myself if I wanted him to do my arsehole.

"If you want to," I replied.

"Mm," Smiled Daniel, "Yours would be my first arsehole."

"Your wife doesn't let you smash in her backdoor?"

"Nah," Laughed Daniel at my crudeness, "Says my cock is too big."

"Well, she's not wrong," I confirmed.

"I know she likes anal, though," Daniel said, "Because she has a butt plug in her vast collection of toys."

"Been snooping, eh?"

"She's not shy about her collection," Daniel laughed, "That's how I knew about that sex shop."

"Your wife shops there?" I chuckled.

"Yep, knows the manager on a first-name basis." Daniel said, "Although she does not know about the secrets upstairs."

He was referring to the porno cinemas where we met several months ago and later had fun.

"Well, if you do fuck my arse," I said, bringing the conversation back anal sex, "You'd part with a kind of virginity."

Daniel let out a neigh of laughter and said that he never considered it as such.

Winter had given way to Spring, and the nights were lengthening. The following weekend was the onset of daylight saving, and this event threatened the viability of our Wednesday trysts. There was more daylight, but the warmer weather meant more people were walking the streets, increasing the risk of getting caught

in flagrante delicto

!

It was frustrating because Daniel had yet to confess to his wife his extra-marital interests, so our time together was limited. As his wife played regularly with other women, I don't see how she would object, but Daniel remained hesitant. Our situation was further complicated by geographic distance because we lived on opposite sides of the city.

If he would tell her, then maybe Daniel and I would have more time to play together.

"Well, I'd better get back home," Sighed Daniel and draining his pint of Kilkenny, "Although I'd kill to blow your cock."

"I'd like that, but it's too risky at our usual spot."

Indeed, it was. Last week, a drunk couple stumbled down the alley just as Daniel's mouth was about to bring me off. While the shadows were creeping, there was just enough light to be spotted, and the couple laughed at me as I scrambled to pull up my slacks. They did not see Daniel and so assumed a woman was fellating me.

"Lucky woman," The guy snickered as they stumbled away.

That the scare robbed me of wood and orgasm, but it was a cautionary note to be careful having sex in public.

Daniel and I slowly made our way to the train station, constantly looking for some suitable spot, but there was nothing, and, frustrated, we said our goodbyes and went home.

****

"I'm ready," Texted Daniel the following Saturday.

"Ready for what?"

"For your awesome cock to brutalise my backdoor," Replied Daniel.

"At the sex shop?" I asked with indifference to that seedy venue.

"Yes," He text, "What do I need to prepare?"

"Make sure you are 'clean'" I tapped and gave him the necessary enema instructions.

"Oh, yes," He replied, "My wife has one of those enema bottles."

"It's the last thing you do before leaving the house," I said, "I'll bring the lubrication."

We met for our usual pre-play drinks in the dark recesses of the Exford Hotel, a short stroll from the sex shop. Daniel was very nervous, and when questioned if he wanted to proceed, he answered in the affirmative. My nerves were on edge at the prospect of buggering Daniel's sensitive hole.

"What's convinced you?" I asked after swallowing my pint of VB.

"I...I...," He stammered, "I used my wife's butt plug the other day...."

"And?"

"Wh... When I switched it on, I...."

"Yes?" I was rock hard at this juicy revelation.

"I...shot the biggest load ever," He said with amazement, "And collapsed on the bed with an incredible orgasmic feeling!"

"Did it hurt, inserting the plug?"

"There was momentary irritation and resistance," He said, "But once it was in, I felt electrified."

I wonder why I do not get the same reaction, I asked myself. To me, the feeling is dulled like the object is "something in my butt", as a former female partner once said.

"Did you come naturally, or did you wank off?"

"I wanked off," Daniel confirmed, "I waited and waited, enjoying the sensation until I felt I was exploding, then I grabbed my cock and boom!"

"How big is your wife's butt plug?"

"See for yourself," Daniel whipped out his phone and scrolled to a photo of a slim, ridged pink toy.

"My cock's bigger than that."

"I know, but you'll open me up and apply plenty of lube?"

Daniel was angling for a rim job that I was happy to perform, and then I will use my fingers to relax his hole before I do what must be done.

"Great," Beamed Daniel, "Ready when you are!"

After finishing my drink, we made our way down Little Bourke Street. With the admission fee paid, we locked ourselves in one of the foetid rooms and began furiously undressing. The warmth of the evening brought the stench from the restaurants below into the room, which, mixed with the room's manly odour, created an unpleasant environment.

However, neither of us cared as we freed our raging pre-cum oozing boners. I was freshly shaven and eagerly anticipating Daniel's sloppy mouth roaming across my parts.

"You're throbbing," I noted as we simultaneously stroked each other's shafts.

"And you're leaking," Observed Daniel scraping a fingernail across my Jap's Eye, "Let me taste it."

Daniel eased me into the creaky wooden chair in the middle of the room. I spread my legs, and he knelt between them, grabbed my quivering spear by its base, opened his mouth and swallowed me whole.

"Oh, fuck yes!" I moaned, throwing my head back in ecstasy.

Daniel generously and methodically sucked on my cock, lapped my rapidly tightening ball sack and taint, edging closer to my tight pucker.

"Turn over," Daniel ordered, his face covered in saliva.

I stood up, turned around and bent over the chair. Daniel roughly spread my arse cheeks, exposing my O-ring. Before gathering my breath from his earlier oral attention, Daniel's tongue stabbed at my hole, eliciting an audible gasp of pleasure. As his tongue cleaned my hole, his hand grabbed my cock and wanked it gently.

"You like that?" Asked Jason as he playfully slapped an arse cheek.

"Fucking love it!" I moaned as I felt his tongue rasped across my sensitive hole.

Daniel's tongue and hand action quickly brought me to the verge of climax. I briefly considered letting him go but stopped Daniel before I blew my stack since I wanted to take his arsehole in the limited time we had together.

"Your turn."

After spending some time throating Daniel's cock, tonguing his balls and rimming his virgin arse, he begged me to finger him. As expected, his hole put up much resistance to my digital probing.

"Shit!" He hissed as his pipe yielded to my intrusion.

The interior of his butt was volcanic and confined. Each penetration, made easier from the copious levels of saliva applied, loosened the muscle, but each time caused Daniel to hiss through grated teeth.

"Keep going," He urged when I asked if I should stop.

As I fingered his butt hole, I decided that relaxation would be gained by additional oral action. So, I attempted, clumsily at first, to nuzzle his hidden balls before readjusting my position to be underneath him and able to suck on his cock. He made my task easier by pointing his cock vertically down towards my salivating mouth.

As expected, throating his cock and tonguing his hairy nut sack relaxed Daniel's O-ring. Soon, two fingers were effortlessly gliding in and out. I hesitantly added a third.

"Do it!" He hissed, "Do it till it hurts."

I forced a third finger inside his dirt chute, and a second later, his cock spasmed violently, and I felt the back of my throat assaulted with ropes of hot white man seed. I was not prepared for his sudden ejaculation, and I naturally gagged, coughed and spluttered. I tried to swallow, but there was too much sperm. The last spurts landed on my chin and throat.

"Whoa there, sailor!" I coughed when his cock ceased twitching, "Some notice would be good."

"Sorry, but that came out of nowhere."

"Yes, and straight down my throat!"

I was not angry or upset with Daniel, just surprised that he came so suddenly and voluminously. My mouth was dry from drinking so much seed that I took a swig of water when Daniel collapsed on the chair to regain his breath.

"Man, that was unbelievable," Breathed Daniel, his chest heaving under pressure, "I cannot wait for you to fuck me."

"You still up for that?" I asked, noting the thin film of sweat that reflected against the light from the street.

"Give me a minute," He replied, accepting the bottled water from me, "How do you want me?"

I glanced at his crotch and saw his cock had not lost any wood despite that tremendous orgasm. I directed Daniel to the stained mattress in the corner and got him into the doggy position. I retrieved the tube of lubricant from my bag and began generously coating my shaft and his loosened anus.

"That feels really good," Daniel moaned, his head tilted and pressed against the mattress.

"You ready?" I asked when the tube was empty.

"Fuck me, fuck me hard," He panted expectantly, "Fuck me till you come."

"Here it comes," I said, nerves taut as I pressed my angry head against Daniel's pucker.

"Oh, yeah," He moaned in a long, drawn-out sigh as I eased my meat inside his virgin bottom.

"Fuck, that's tight!" I hissed as the walls of his volcanic anus pressed against my shaft.

"Of course, it's tight," Daniel growled, "It's never been fucked before!"

"Butt plug," I reminded him.

"Doesn't count!"

"I'm in," I said, "Balls deep."

"Feels great!"

I ground away at Daniel's pucker slowly at first, but when he began rocking his hips and pushing back against my pelvis, I knew it was time to take him harder. The excess lubrication and Daniel's relaxed state allowed me to mine the depths of his shitter with savage determination.

"Fuck, that's deep!"

For his part, Daniel was moaning and venting unintelligible words as I brutally sodomised him. I reversed cowboyed him from doggy by sitting on the chair, side saddled him, pile drove his anus and took him missionary on the floor. His was a fabulous arsehole, and the harder I fucked him, the more Daniel moaned with pleasure, reassuring me all the way that he was enjoying himself.

"I'm getting that feeling again," Daniel suddenly moaned.

"What feeling?"

"The need to come!" He replied, "Are you close?"

I was not because I was deliberately holding off since his O-ring felt so good strangling my greasy cock, but I guessed he wanted us to orgasm together, and I was okay with that.

"Good," He panted, "Come inside me!"

I positioned Daniel against the window to the street, three floors up, forced his head outside and rammed my cock back inside his arsehole. He took hold of his mammoth shaft and pumped it with furious purpose as my hips slammed against his cheeks.

"Here it comes!" I hissed as my legs shook, and the bolt of electricity travelled up my spasming shaft, "Fuck!"

I was unaware of my environment for ten or twenty seconds as my brain scrambled and my nerves sizzled. Suddenly Daniel shook violently as his orgasm followed mine, his seed falling to the floor. I held Daniel firm in my grip until he ceased spasming.

After what seemed an age, I eased my dying cock from Daniel's brutalised pucker with a satisfying 'pop', but alas, there was no gape. We were spent and dripping in sweat from the exertion and balmy evening's air.

"That was amazing," Said Daniel breaking the silence between us, "Better than I ever imagined."

"Awesome!" I agreed.

"We should do it again," Snorted Daniel reaching for his shirt and thereby signalling that the night's activities were at an end.

"I'm available anytime!" I said, hinting at his wife.

The hint was not taken, and we began dressing in silence. We said our goodbyes on Swanston Street and departed in opposite directions for home, both thoroughly satisfied and with promises for a second round soon.