First Time Anal

It all started when I was 25. Working in a bar in Sydney, great place to be at that age and great people to work with. We all got on well together and I became friends with one guy who had similar tastes to me, good food, good wine and good cognac. It is amazing how quickly you learn about the good things from working in a bar.

On our days off we would often dine out at some of Sydney's best restaurants. One day he asked if he could cook me a dinner, he boasted that he was not a bad cook. He said it would be cheaper than eating out and he would cook my favourite meal (which happens to be Chateaubriand, or really any fillet steak as long as it had béarnaise sauce with it.). I, of course, accepted. Love a free meal, so the date was set for the upcoming Sunday.

I arrived at the agreed time with a good cab sav under my arm and was greeted with a Chivas Regal on the rocks, (another of my favourites). We sat and chatted, another scotch, while he checked the food, another scotch and it was time for dinner. Without going into boring details, the soup was excellent and the steak fantastic, all washed down with a fair bit of red wine. After, we sat with coffee and cognac and talked more.

Time seemed to fly and I noticed it was getting late, so I said I better be going. He said it would not be a good idea for me to drive considering the amount of alcohol we had consumed, why don't I stay here for the night. I must admit that I was really looking forward to my own bed but he was right about the booze I had consumed.

"So where will I sleep?" I said

"I have a king size bed and I promise I won't bite." He replied.

So after a bit of to-ing and fro-ing, I decided to accept.

We went into the bedroom, stripped down to our underwear and climbed into bed. I thanked him for an excellent meal and the lights were turned out. As is usually the case, I was now wide awake and restless. I started on my side and then on my back, trying not to disturb him laying next to me.

Laying there in the dark silence, I thought I felt something touch my leg, just on the side of my naked upper thigh. Must have imagined it. Then I felt it again, I hadn't imagined it. This time the finger stayed there, resting lightly on my skin. I didn't know what to do, should I turn over on my side, was it accidental, he could be asleep and his hand just landed there, my mind was going a million miles an hour, so I just stayed still.

My heart was thumping, I was sure he would be able to hear it, then his finger started lightly circling the side of my thigh. Around and around, then two fingers. The feeling was unbelievable and I could feel my cock beginning to grow. He then moved up my naked flesh and over the top to start stroking my inner thigh. He slowly moved up until his finger grazed the material covering my balls. My cock was now rock hard, I have never experienced it being so hard, if I was standing up, it would have been flat agains my stomach. He stroked my balls gently and slowly moved his whole hand up and over my cock. His hand moved up and down over it,

I am sure I was trembling, I had never experienced such a sensational turn on in my life. I then felt the hand move up over my stomach lightly caressing it until it moved down, fingers slipped under the waistband and until there was a hand on my naked, raging hard cock. It involuntarily twitched at the touch as it felt so good. Fingers wrapped around it moving slowly up and down, he then hooked the waistband down under my balls for a better access.

I had forgotten how good it feels to have another male's hand on my cock, not since school days, and it felt so good, so wrong but so right and natural, a feeling you don't get from a woman's touch. He then pulled my pants all the way down and off.

"Wait a minute". He said

With that he got out of bed grabbed something from the dressing table and returned. Before he got back on the bed he removed his shorts also. I then felt something cool on my cock, then his hand. it was slippery and the hand on my cock glided with ease. The feeling was even better than before. I didn't think that could be possible.

He said: "Do you want some? Hold out your hand".

I did and felt the oil dripping onto it. He then return his hand to my cock, stroking, sliding up and down. I reached down with my oiled hand and found his cock. Wrapping my fingers around it, I too started to stroke. It was bigger than mine, about 7" with a small head compared to the thickness. It was thick, thicker than mine and felt wonderful under my touch. I stroked the circumcised head then down as he worked on mine. I am getting hard now remembering the feeling, it was indescribable.

Next he poured some of the oil over my stomach and rubbed it around, then put his leg over my body and climbed on top. He began humping me, cock on slippery cock, cock on stomach skin, the feeling of slippery flesh on flesh was unbelievable. Feeling his cock sliding up and down my stomach, up and down on my cock with my cock on his and his oiled stomach. I knew I wouldn't last long, so I told him.

"Me neither, but don't hold back". He said.

With that it took me about 3 or 4 more passes of his body over mine for me to let go, deep from my balls cum pumped out of my cock, a throbbing I had never experienced before, joining the oil to make a gooey even more slippery mess. I just lay there totally exhausted and let him ride me, I entwined my legs with his as he was picking up the pace so I knew it would not be long. Two more strokes and he grunts and grunts, I feel his cock throb against my stomach and a new warm wetness on my skin. He then collapsed on top of me and I couldn't help wriggle a bit to get more of the wet, warm slippery sensation on my skin.

After that night we were so normal and natural about it as if was a totally normal occurrence. We still had girl friends but we also had time together. If he was at my place or me at his and the feeling struck him, he would reach over and place his hand on my cock and say:

"Hows he been behaving?"

Then he would start stroking me. He was always the instigator. This would lead to me stroking him and in no time we are both naked enjoying the feeling of each other's bodies.

One night after we had enjoyed a nice restaurant meal and were back at my place having some post dinner drinks, he reached for my cock as usual and as usual we ended up naked on the couch. After a bit of play and stroke he leaned down and took my hard cock in his mouth. It felt so warm, wet and hot. Again nothing like when a woman takes my cock in her mouth. Hard to explain the difference but it feels oh so much better. After a short while he lifted his head.

"Please suck my cock Michael."

Which I did. I had never sucked a cock before, I don't know why not as it was so pleasurable having this soft yet hard piece of another man in my mouth. There was no way I could take it all, but I managed as much as I could and used my tongue to explore the intricacies of his beautiful penis. Bobbing up and down the pleasure was heightened by him doing it to me. Our second meal for the night.

He was caressing my balls while sucking and a finger grazed the skin between my balls and hole. I didn't realise how sensitive that area is. His finger moved down and reached my little puckered hole, running over and around it. His finger disappeared for a while then returned, it felt wet and slippery. As he was caressing my asshole I could feel it relax and enjoyed the sensation.

Then the finger slipped in, just a bit but enough for me to know the finger was inside me, just a finger nails depth. It didn't feel unpleasant, in fact it felt good. He worked it around a bit and then in and out, each time I could feel the finger going deeper with each push. The finger disappeared again, then returned even wetter resulting in the finger entering and going in easier than before. I realised he was using his saliva. Then I felt a second finger attempting to join the first. It did and I now had two fingers working gently in and out of my ass. He then turned to me.

"Michael, I want to fuck you."

Now I have a very sensitive ass, I have had dildos and plugs in it and it really increased the intensity of my climax, it felt so good and seemed to produce more cum. But I have never had anything in there 7 inches long and the girth of his cock. Also I could control the fucking whereas now I was supposed to put that control in the hands of someone else. But I really wanted to try a real cock, if dildos felt good, imagine how the real thing would feel. Plus the alcohol was enough to overcome my inhibitions.

"I'm willing to try it if you go easy and use plenty of lube, I'll get it for you."

After returning from the bathroom and handing him the lube, I took my position on hands and knees in doggy position. Don't know why I didn't ask how he wanted me, but just assumed that position. He put lube on his fingers and started to work on my hole. Firstly around it and rubbing a finger across it until it slipped in easily, not far at first, just working the lube on, around and just in the entrance. Well it felt good so far, I was really enjoying it. He would have applied 3 or 4, the last two concentrating more inside. Then nothing, I was imagining he was applying it to his cock.

The next think I felt was this soft yet hard pressure at the opening to my hole. Well here we go, I thought. Surprisingly the head popped in easily as he rested it just inside. Then he started to push, he reached a few inches inside when his cock seemed to reach a brick wall, the more he pushed the more I thought I would be split in two. After trying a few times.

"I can't take, it must be too big for me."

"It's alright just relax baby, you will be able to take it, just relax."

He called me 'baby' and then it hit me. Here was I on my hands and knees offering my hole to a man, I all of a sudden felt cheap, I was his baby, his tart, slut or whore, my ass was there for his pleasure to use. I asked him to try some more lube, heaps this time and we will try again. He did and some more on his cock, then it was at my opening again, head easy in, then the brick wall.

"Relax baby."

"I'm trying, I really want it in me.

Then he reached underneath me and started caressing under my balls and the skin between my balls and hole, softly, so softy. All the time he was rocking his cock back and forward in me, each time forward he was entering a little more. His caressing felt so good and I seemed to be feeling fuller in my canal. Then he stopped, I could feel his pubic hair on the cheeks of my ass. Reaching between my leg I felt upwards and there was no room between his pubes and my ass.

All 7 inches was totally in me. It felt so good, I felt full and fulfilled. Then the rocking started back and forward as he was working my ass, no pain only full pleasure. The way a mans pubic region is concave and a mans ass is convex makes them both a perfect fit, before the rocking it was a perfect join of his front against my rear, with his cock connecting us. It seemed so wrong but felt so right.

His rocking continued and his strokes longer, each one past my prostate and heightened my pleasure, I noticed though that my cock was limp, although the feeling was like a raging hard on. The tempo picked up, all you could hear was both of us grunting and the slap of his thighs against my ass. Faster, faster, deeper, deeper, if that was possible.

"You feel so good baby so tight, so hot"

"Fuck me, fuck me hard, use me." I said.

I couldn't believe that was coming out of my mouth. He was now holding my hips and slamming me onto his cock. The constant rubbing of my prostate was starting to stir things in my balls, I knew I wouldn't be able to hang on much longer, but I wanted to, I wanted the feeling to go on forever. I told him I was about to cum.

"Cum for me baby, cum, I want to feel that on my cock, I won't be far behind you."

I felt it rising, rising and then exploding, cum shooting everywhere, on my stomach on the carpet on my legs and his, heightened by the feeling of my asshole gripping his cock in cum pulses. I nearly passed out from the pleasure, a pleasure I have never felt before. I could feel his grip on my hips tighten and the pace pick up and knew he was not far away. Then he started groaning and grunting and with three long thrusts into me he stopped, as deep as he could go, tight up against my ass and was still. All I could hear was him grunt, grunt, grunt, but what I could feel was a pulsing in my whole anal canal as his cock spewed cum deep inside me. It was weird as it felt hot and wet even though it was the same temperature as my body, but it felt like I was being pumped full of a hot wet, liquid. It felt so good.

He collapsed on my back and stayed there, breathing heavily in my ear and kissing it.

"Thank you baby, that was fantastic, I have wanted to do that since we first met" he said.

"The pleasure is mine."

I am now complete, I have offered myself to a man and he has used me, fucked me for his pleasure, it is the sluttyness of it all that makes me feel so satisfied, I guess I need a man to control and take control of me. The worst part was to come, his cock was shrinking and slid and popped out of my ass, cum stated dribbling down my thighs and I felt as if my ass was gaping and been well and truly fucked. I would have liked his cock to stay in me forever, but we can't always have what we want, or can we??