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My first time, was with a guy

Young guy realises he has a twink side
As he lay on his bed I told him: ‘I think, I’m ready to give it a try’. I got up and walked near to his bed.

‘Good, do come over to my bed, and sit next to me. Okay, I will show you what I do and how I can open up to accept a finger easily. You can do it too with some practice. Remember if you ever get the chance to have anal sex with one of the ladies here at college, you have to start with her just as I am going to show you now. Otherwise you will cause her pain and that will be it, you will have lost your chance to do this with her.’

I was glad to hear him talking about doing this with a woman, as that seemed to make this all more normal in my mind. I was nervous sitting on his bed and apprehensive about what we were about to do together. I got butterflies in my stomach and kind of sweaty. I decided to go ahead and see what happens, figuring that I can always say I want to stop and not go any further.

In a blink of the eye he pulled down his shorts and briefs to his ankles. Then with a flick of his foot, they sailed across the room nearly landing on my bed. He parted open his legs as he drew up is feet nearly to his hips. He was spread so that his knees were now nearly touching the bed. I looked down between his legs as he lay on his back. The way he was positioned I had just the slightest view up his anal opening under his ball sack. His had the strongest urge to touch and examine his uncircumcised cock. I decided to ignore that impulse.

With one hand he pulled his balls up and slid his butt down and out, allowing me a clear view of his opening. He had little hair there and not really much on his scrotum either. I glanced again at his cock, which now had half of a drop of pre-come showing in the fine slit of his gland. His foreskin was beginning to withdraw as he harden and grew.

‘Open my bedside drawer and get out my bottle of Astroglide. Open up the top tip and hand it to me, please.’

I found the little plastic bottle, opened it and handed it to him. He lubricated his middle finger, dropped his hand down and after he had let out a long deep breath, he slid in the wet finger slowly into his dark opening as he breathed in. He paused, exhaled deeply, another pause… then as he inhaled, and he presses it home, more and more. He repeated this slow deliberate process, as his finger seemed to slip in effortlessly past his knuckles right up to the hilt. It was amazing in my mind that I was watching this and that he did not seem to be staining at all do it.

I asked, ‘Does it hurt?’

‘Nope, not in the least, in fact it feels good.’

I said that I got it, and started to get off of his bed.

‘Hey, where do you think you’re going? Do you want to learn how to do this or not? Put some lube on your finger, come nearer and press you fingertip gently on my anus.’

I felt very nervous now. I put a few drops of the slippery liquid on my index finger, kind of crawled up between his legs on my knees. I looked down to his opening as he withdrew his finger. I knew that time had come; yet I had never touched a man in a sexual way before. And I sure had not touched a guy with his pant off… I hadn’t touched anyone, but me, sexually.

Looked like that was going to change right now, so without thinking about it further, I pressed my finger over his bum-hole. I was kind of shocked as I touched it. Silence filled the room. All I could hear was our breathing, which seems to be rapid and excited. ‘Okay, I’m ready for you to press in. I’m going to take a deep breath in, let it out and then breathe in again. Then, as I breathe that last time, I want you to press in slowly and gently. You will feel me loosen and then open, when you feel that press in a little and you will feel the inter sphincter, stop there and wait for me to do the breathing cycle again. Got it?’

‘Yes’, I said weakly.

Just as he had said, I felt his outer sphincter loosen and open with my pressure against him. Then my finger entered him maybe an inch or so. And then with another breath, he further widened his second hole opening and my seemed to just glide in. It was as though he was pulling my finger in, as I gently pushed in until my second knuckle was inside.

‘Press it in all the way’, he whispered to me.

I did until the entire length of my finger in his anal canal. He moaned. He felt warm, tight and smooth inside. I felt shaky and had to concentrate to hold my arm and hand still or I would have betrayed my nervous excitement. I could not speak.

‘I want you to now press the tip of my finger forward and up towards my cock, then slide it back and up in the direction of my naval to see if you are able to feel the prostrate gland.

As I did so, he moaned again, only louder this time. I was sure I had felt it and from his reaction I must have hit it.

‘Yes, you have it, press back and forth on my button.’ He urged. Again as I did so, he moaned again and then again with each pass of my finger over his gland.

I stopped moving it for a second and he quickly implored me to keep massaging him. Slide you finger in and out of me while you rub over it… With one of his hands he gave his cock long hard strokes, and with the other he pulled up and out on his nuts stretching his ball sack tightly. I thought that doing so would hurt and I kind of winced.

He quickly came with huge globs of white cum shooting out of his prick. I sat there amazed with my finger still in him, feeling his anus tighten rhythmically with the spurts of his climax. His ejaculate oozed out of his cock and down over his fist. I started at his cock.

I started to move my finger, and he said: ‘Be careful not to press on my prostate as you pull out, it is very sensitive now’.

I carefully and slowly pulled out of him. As I did so, it felt as though he was hanging onto me. I was frozen in place not knowing what to do next. With several wads of Kleenex he cleaned up the mess he had made. His come was all over his thighs, stomach and chest. He sure came allot.

He said: ‘Wow that really felt great! You should try it. Are you ready to give it a go?’

I didn’t feel up for that and begged off, saying: ‘I think that I’ve had experienced enough for one day.’

I wanted to go to my bed and masturbate, as my cock had been rigid for a long time and my balls begged for release.

‘Come on, you must want to come. How about it? Would you like to slip your cock into me? I am all-loose, opened up and ready for that. You did a great job of getting me off. It’s my turn to return the favor.’

I did not know what to say… I wanted to do it and at the same time I was kind of scared and worried about doing all of this with a guy. He let the silence settle in for a while.

Then he said, ‘Come on take off your clothes, I want you to do it, I really do. Please let’s do it together, now.’ My resistance stared to fade and apparently he sensed that because he reached over and handed me the Astroglide. I took it and knew that with that I was agreeing to proceed.
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