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My Gay Fantasy Is Fulfilled

"I needed to turn fantasy into reality."

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I needed to find out if a man could pleasure me

My name is Andy and I am in my late thirties. I am of medium build and enjoy taking myself to a fantasy world, when I masturbate. This story is about how I brought one of my fantasies to life.

I have had a gay fantasy, which I have used during masturbation for several years. One evening after a couple of drinks I felt incredibly horny, so I Googled a gay chat room I know, which allows you to cam the person you are chatting with.

I started a conversation with a guy, called Greg, who lives relatively local to me. We initially shared information about our fantasies. I told him that I fantasised about masturbating with another man and receiving a full body massage. He told me he fantasised about dominating another man. We got each other very horny. After an hours chat, I suggested turning on our cameras so we could see each other’s erect cock. Within seconds Greg’s hard, erect penis appeared on my screen. Greg was in his late twenties and had a good body. He and I watched each other masturbate. I watched him cum first, squirting three times into the towel he had laid on the floor. Soon after I gave Greg the same show, as I ejaculated onto my t-shirt which I had on the floor in front of me.

Greg then said, ‘This would be fun to do in person.’

I had to agree.

We arranged to meet on Friday night, in a pub next to a golf course we had both played in the past. We agreed to meet at 7.30 in the pub and take it from there.

Friday came and I dressed in a pair of chinos and a light blue shirt. I put on some cologne and headed for the pub. I was very nervous and my body was tingling. When I entered the bar, Greg was already sat at a table with a pint of beer. I acknowledged him and went to the bar to get myself a drink. I then joined Greg at the table.

Conversation was light and friendly; we discussed how we knew about the pub, what we thought of the golf course next door and other trivial things. We had a second drink as our chat continued. By 9 it was dark outside and we seemed to be getting on well, sharing several mutual interests.

‘Would like to go for a walk outside?’ Greg asked.

‘Yes,' I replied.

We headed down a path that led onto the golf course. Now we were alone our conversation became more sexual. We found a bench and sat down next to each other. Greg put his hand on my thigh and started to stroke it gently. After a few strokes he deliberately let his hand brush against my groin, which allowed him to detect my erect penis. He moved his hand away and then back again, this time lingering longer to see what my reaction would be. He was fully aware that I had not been with another man before. As he stroked my mound, he leaned across and kissed me on the lips. This took me by surprise initially, but after a moment or two I began to enjoy it. I pulled Greg close to me and we kissed again.

I said to Greg, ‘I didn’t really want to do this outside, as it seems a bit seedy.’

He suggested we go back to his place, where he would give me the sensual massage, I had described to him previously.

Greg lived within walking distance of the pub, so it only took twenty minutes to get to his flat. During the walk I was going through events in my mind, wondering if I should make excuses to opt out. I decided that I needed to experience this and tonight seemed as good a time as any.

Greg was bi and had been with men before. He did not act camp and certainly didn’t have a gay ascent (straight guys will know what I mean). He was about 5’11’’, an inch or so taller than me, with short brown hair and eyes, not too dissimilar to myself. He had a medium build, his bum looked nice in his jeans and I felt myself being turned on by him.

On entering Greg’s flat, he offered me a whiskey, which I accepted . As he gave me the glass, he kissed me again. My cock began to stir in my pants and a bulge was very noticeable for Greg to see. Greg pulled away from the kiss, looked down and stroked my groin. As we kissed again, he pressed his groin into my thigh, so I could feel his hardness.

Greg turned on his computer and some porn appeared on his large TV screen. The porn was my favourite, MMF bi threesome, which I had told Greg I liked while we were online.

Greg and I watched the action for a about fifteen minutes, not really saying much, as we stroked each other through our clothes.

Greg said, ‘I'm sorry but I am going to have to remove these jeans to give my cock some room.’

He stood up, undid his fly and pulled his jeans off, revealing a pair of blue boxers with a very big bulge in them and a damp spot of pre-cum.

He sat next to me, took my hand and guided it toward his erect penis. I gently rubbed it through the material of his boxers.

‘Are you ready for that massage yet?’ He asked. 

I said, ‘Yes,' with a tremble in my voice. 

He disappeared for a moment and returned with two large white towels. He opened one and laid it out on the floor, in front of the fireplace. He then lit the candles in the room and asked me to remove my clothes.

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I stripped to my briefs and stood there looking at Greg. He looked me up and down with a huge grin on his face. Then walked towards me and we kissed again.

‘Lie down on your front and I will massage your back first, to relieve the tension in your shoulders,’ he said.

I lay on the towel face down and he poured some oil onto my back. Greg started to massage the oil into my body. He initially worked on my shoulders, which helped me to relax. I started to moan in appreciation of the work he was doing. Then he started to work down to the small of my back and run his hands along the waistband of my briefs.

After a few laps of the small of my back, his hand drifted underneath the waistband of my briefs, which caused me to moan with pleasure again. With each circular motion of his hands, he moved deeper into my underwear.

I raised my hips off the ground, allowing Greg to apply enough downward pressure to uncover my buttocks and pull my briefs down over my knees and eventually discard them.

Now my arse was completely at Greg’s mercy. He applied some more oil to his hands and then began smearing it over my buttocks. Initially he flirted with my crack, until eventually his hand slipped easily in-between them, to gain access to may anus. He circled my anus with his fingertips and then applied enough pressure to its dimple, to enable a finger to disappear inside me. I received his finger with a pleasurable groan. He then moved his finger in and out slowly, but with each inward stroke he went deeper.

After several strokes Greg said, ‘Roll on to your back.’ 

As I laid on my back, my penis pointed up, towards my chin. Greg poured oil on my belly and started to massage me again, in large circles. Eventually the diameter of his circles allowed him to reach my cock. He took my cock in his oiled hand and rubbed the length of my shaft slowly. I was now in a state of total ecstasy. I looked at Greg and smiled. He leaned forward and kissed me.

Greg was still wearing his boxers, so I hooked a finger into the waistband, indicating to him that I would like him to take them off. He removed his t-shirt first and then stood up and pulled down his boxers, keeping eye contact with me the whole time. As he pulled down his boxers his penis stood proudly to attention.

‘What do you think?’ he asked me.

‘Very nice,’ I replied.

Greg knelt down beside me and continued to massage my erect cock. He cupped my balls, kneading them gently, and then went in search of my anus. I bent my knees towards my chest, parted my thighs and lifted my buttocks to give him better access to my anus. He pushed a finger into me and soon afterwards made it two. My arse is very tight, which Greg noticed, as he tried to insert a third finger. I was aware that when he thought the time was right, his fingers would be replaced by his erect cock.

Greg knew that I wanted him to wear a condom. As I lay there in ecstasy, with my eyes closed, I could hear him tear open a condom wrapper. I opened my eyes to watch him roll it onto his erection. I turned onto my stomach and knelt on all fours. This parted my buttocks. After a quick finger, I could feel his erection pressing at my opening. I then felt a pleasant cold sensation, as he poured lube onto my ring. Then he took hold of my hips, pulling them back towards him, as he pushed forward. I felt his length entering me. It was a wonderful feeling.

Greg started to stroke his penis in and out of my arse slowly and I was enjoying every stroke. After a few minutes his pace began to increase and I knew he was getting closer to orgasm. As his orgasm got closer his strokes got deeper and harder, which felt good. Then with a loud groan he shot his first load. The next two thrusts were deeper and harder as he emptied is balls.

He left his penis inside me for a moment, as his orgasm subsided, eventually withdrawing. As he withdrew, I turned to look at him, noticing the condom was full of his cum. We both smiled at each other and he leaned forward to kiss me. He removed the condom and lay next to me.

He said gently, ‘Are you OK?’

I said, ‘I'm fine.’ I kissed him.

As we kissed he stroked my penis to hardness. As my penis hardened, his strokes got longer and faster. After the pleasure of being entered, it was not long until I reached the point of no return. His kisses moved down my body, until I could feel his breathing on my cock. I then felt a warm sensation as he took my cock into his mouth. I began to push my cock in and out of my mouth. I could feel my cum beginning to leave my balls.

I said to Greg, ‘I'm cuming,' as I didn’t know if he wanted me to cum in his mouth.

When I told him this, he sucked deeper and harder. I let out a loud groan and shot my load into his mouth. I felt three good squirts of my cum fill this mouth and he took each one with relish.

When Greg was sure my balls were empty, he laid back next to me and we kissed. I could taste my cum in his mouth. He put his arm across my chest and one leg over mine and we lay still, in the dimmed light, enjoying the afterglow of our orgasms.

I knew that I would want some more before the night was over.

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Written by likekissingthighs
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