My First Time - Anal Sex

I had been chatting with a married bi guy, Dan, on a popular Australian site (I was put on to him by a cum buddy, Rob), we eventually exchanged mobile numbers and began chatting on a chat app. Having a lot in common including the difficulty of finding a place to meet and have a bit of fun, we decide to meet in the car for a chat.

I drove to the local parkway, parked, locked my car and hopped in Dan's car, an SUV. He was an older guy with a good personality and a sexual deviant side. We talked about what we liked and how we could get together more, Dan knew I was an anal virgin, and as a top wanted to pop my cherry.

Dan suggested we go for a drive as the carpark was a bit conspicuous, he drove to a quiet spot on the side of the road out of town, and we continue chatting as he pulled his cock out, stroking it, I reached over and had a play, then leaning over taking his cock in my mouth, this I was relatively new too, but already loved doing. Between sucking Dan's cock and his vigorous stroking, he soon ejaculated a hot creamy load, something I was to later taste and swallow on many occasions. In the back of my mind, I wish I had at least tasted his cum if not swallowed it.

Dan cleaned up, then came around to the passenger door, I already had my cock out and had been stroking. Dan opened the door, leaned in taking my cock into his mouth, hungrily sucking my cock, pausing only for a couple of passing cars. I tell him I'm about to cum, he looks up, winks and continues sucking even more vigorously until I unload in his mouth, he drains every drop from me, then looks at me grinning as he licks his lips. As Dan drives me back to my car, he lets me know his house is free some days of the week, and he would love to take my arse cherry. So we organise to take one of those opportunities soon, for Dan to introduce me to the world of male anal sex as a bottom.

Finally, the planets align, one Monday morning, I'm available and Dan's house is free. We decide to meet at his place between 9 am and 12 pm. After some internet searching I have worked out what I need to do, to ensure I'm ready for my first anal sex experience (Some great sites on the internet to help a novice adventurer). I shower and prepare for Dan to take my arse cherry. Even though my nerves and butterflies are pinging higher than ever, this is something I have wanted for a long time, so I'm resolute in making it happen.

After texting Dan, I head over, parking out front; as I get to the front door Dan is waiting to let me in, he closes the door leading me to a room with a desk and some office chairs. he pulls me close massaging my cock through my pants, kissing me, something I had never done with a guy, but the excitement and sexual tension draws me in and I reciprocate deep tongue sucking and kissing.

Dan starts to undress, and so do the same, as he sits on a chair starting some guy-on-guy porn on the computer, I kneel in front of his chair, between his legs, and begin to lick his cock all over before taking the head of his cock into my mouth, while I massage his balls. This is the first time Dan tells me he likes his cock bitten/chewed along the shaft, I oblige but far more gently than I later find he likes, but wow, something very new to me, so I am very cautious.

Dan let me know what he liked, so I took his guidance sucking his cock and licking his balls. He then asks if I want my virgin hole fucked, and I nod enthusiastically. He puts his hand on the back of my head prompting me to keep sucking and licking his cock, he then leans down and starts rubbing my hole. I realise his fingers are covered in lubricant, as he presses on my hole until his finger is inside me, then he slowly inserted a second finger, his fingers stretching my hole, finger fucking me. I am mesmerised by this feeling as well as his cock being in my mouth at the same time. He withdraws his fingers and prompts me to get up.

Dan tells me to kneel on the office chair facing the back of the chair and spread my butt cheeks. Dan stands behind me, applying more lube to my hole, then stoking his cock with lube, fingering me with one then two fingers again, I think this feels great but I'm about to find this is nothing compared to what is to come.

Dan positions himself behind me, and I feel his cock pressing on my lubed and fingered hole, he pushes his cock into me, this feels amazing, but I am very soon to find out this is only the head of his cock pushing against my inner sphincter, and I feel a sensation I could never have imagined as his cock forces its way past my inner sphincter, his cock feels amazing inside me. He alternates between fucking me and stroking his cock and fingering me, soon fucking me more intensely. My mind is just thinking

how I never want this feeling to stop. He knows I want him to cum inside me, so he soon unloads deep inside me, with two deep hard thrusts as he explodes inside me, then he pulls out, his cum still spurting on my arse and legs, and I realise what an impressive load I'm experiencing. I get up seeing a tasty rope of cum on the towel on the chair, I resist the urge to suck it out of the towel.

As I get dressed I tell Dan how amazing it was and I really want to do this again soon, I'm immediately hooked on being fucked, especially if I trust the guy enough to be fucked raw, skin on skin.

I leave Dan's house, heading to the main street of town, I decide to have a coffee at a local cafe, sitting there knowing I have another man's cum deep in my arse. Sitting here knowing my arse has been bred and I'm full of cum. Doing this becomes a ritual, each time Dan fucks me. I walk around town then go home determined to keep his cum in me as long as possible.

I enjoy being fucked by Dan several times between some awesome sessions sucking his cock and swallowing his tasty big load in his SUV.