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More Adventures With John

"Pushing My Boundaries"

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Author's Notes

"Based on real events with some fantasies. Names have been changed. This is the follow up to "My Gay Awakening With John""

The following day at work, I was in a semi daze thinking about John's thick cock and how hard he had been. I swear I could still taste his salty cum in my mouth. It was a reminder that I needed to search for something to enable me to take him deep as he had requested.

After some food, I got the laptop out and searched to find dildos for sale. There were so many different types! I opted for a nice looking six inch one, having decided that it would be John who would be the first to penetrate me any further. I ended up with a raging hard on and masturbated until my man juice spurted.

A few days later, and the package arrived - as promised in a plain looking box. Luckily, I was on a day off so had plenty of time to pleasure myself. I opened the parcel and took my new toy into my bedroom where I quickly got naked. It goes without saying that I was rock hard in anticipation. I placed the dildo upright on my bed, and slid my ass over it until I could feel the tip pushing against my hole. I lowered myself down, just as I had done with John's cock and felt my sphincter muscle relax. The dildo slid in slowly, but it was much more painful than the real thing. I stopped for a while until the pain subsided before attempting to go deeper. I had to stop again - I had only just got about half way in and my erection had disappeared.

I thought I had done something wrong, but a quick internet search for "anal training" showed two things: One; I needed some lubrication (John's cock had been in my mouth before he entered me). Two; I should start smaller and work up. I revisited the site I had purchased the dildo from and placed a bigger order. A set of butt plugs, an anal cleaning kit and some lube. Let the practice begin!

The butt plugs were great with that initial lovely feeling of the widest part stretching me. and I found that it was a good way to prepare for something else. The dildo was awesome with the different feeling of being filled and stretched at the same time.

Three weeks or so later, and the much anticipated phone call came at last - it was John! He wanted to see me again so I quickly gave directions to my flat. It seemed a long wait, but about thirty minutes later there was a knock at the door. I went and opened said door and saw him again. He looked so handsome, tousled blondish hair, smart green polo shirt and jeans. Exchanging greeting, I led him into the hallway and as soon as I had turned around from closing the door, he was kissing me deeply and our tongues lashed together. His hands clasped my buttocks tightly. I couldn't help but caress the front of his jeans and felt that lovely semi hard bulge that I remembered.

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I led him into the bedroom with our clothes leaving a trail in our wake. He sat on the bed with his superb 8" cock fully erect and my mouth watered at once at the thought of tasting him. I knelt down and took his bulbous head into my willing mouth - such a sweet, salty taste that I loved.

I got to work, licking the full length of his cock from base to tip before taking him into my mouth again. John's hands were on the back of my head, and pushed me down so that I took even more of him into my throat. Since I had practised deep throat with my dildo, I welcomed him further down until my lips were close to the base of his thick shaft. It wasn't long before I felt the little twitch that meant he was about to cum. I pulled back a little just in time for the first spurt of cum to hit the back of my throat, soon followed by more. I swallowed as much as I could, but by the time he was spent, I felt some of his cum dribbling down my chin.

I stood up, went to the bedside table to get the lube I had bought and applied some to my ass hole. I got back onto the bed, and spread some lube onto my hands and rubbed it onto John's cock. It wasn't long before he was hard again and I was able to mount him. He slid into my willing ass so nicely and I felt his thickness spreading my cavity wide. It wasn't long before he was at the same depth as the dildo I had been practising with, and with a little effort I pushed past that to his full length. I came almost immediately - such an intense orgasm and my first ever hands free. My cum covered his chest in white blobs - he looked incredibly sexy.

I sat on the full length of his incredible cock relishing the feeling of being so full inside and my ass cavity stretched wide. I sensed him start to move his hips down into the mattress in little movements as he began to fuck me slowly. I willingly moved with him - testing to see how far I could move up and down on his shaft. We soon swapped positions so that I was on my knees again as he buried himself into me from behind. He took his time, sometimes long and deep, some shorter hard bursts. Soon enough, John thrust himself all the way in, grunted and came into his special place deep inside me.

We had a quick shower and he stayed the night - another first for me. In the morning, we had a joint cock sucking session with cum swap kissing to follow. After we had showered, John got dressed and told me to shave all my bodily hair before our next meeting. As he walked out of the door, I wondered what he had in store for our next meeting.

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Written by alwayscurious
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