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Who knew it could be so good?

"I'd never taken a cock in my ass before"

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Author's Notes

"If this excites you drop me a DM to let me know!"

One of things I have always been able to do well is to make women orgasm well and often repeatedly. After my marriage ended and I got back into the dating scene I found that it had changed dramatically. Tinder and Bumble and other dating apps were the place to meet women, and there were plenty of them looking to meet but I discovered that most guys had terrible profiles making mine stand out. So I was really enjoying living in a new city dating many different women, and the other thing that I discovered was that in the main their attitudes to sex had changed significantly thanks to it seemed all of thee having read 50 shades of gray.

I couldn't tell you the number of times I heard the phrase ``I'm not vanilla', occasionally they even had it on their profiles, so for those ladies on about the third or fourth date I would start to include a bit of ass play, a bit of lube, a bit of sliding the tip of my cock backwards and forwards over their butt hole and always it would relax and let me in, and then slowly I'd work myself all the way in and then gently build up the rhythym.

For most I don't think they'd ever actually had anal before but there were a few who were well seasoned and the one thing I couldn't get over was when I got it right they absolutely loved it, they would lose control and be making the most unreal amount of noise, shaking and coming and moaning and demanding more. I was fascinated with how good it was for them, and how intense their orgasms were. I experimented a lot with combining anal with vibrators on their clits, in their vaginas, it was a lot of fun but I had to admit to myself that I was a little envious of their intense orgasms.

I've never really been attracted to men at all and I didn't think that I could touch one or be touched by a guy sexually and enjoy it. The old Kiwi fear of being called out gay I guess, but one night I was at a sex party lying on my back going 69 with a woman and she was alternating between sucking me and stroking me with her hand. Next thing I know she's asking me, how do I like that? The thing was I was still being sucked and when I looked around her it was a guy doing it, he was doing it extremely well and I was not far off coming. Next thing I knew there was a well lubed finger working its way into my ass and stroking the back of my prostate. Holy fuck the sensation was incredible. It built and built and it was such an amazing experience because I still had these lovely legs either side of my face, and her clit on my tongue, and her vagina right there in front of me, her body on mine and her smell all around but I lost all control and came really really hard in his mouth and then just lay there shaking in a full body orgasm for what seemed like minutes after.

So I didn't think of myself as bi for a second after that. Yes, I'd come in a guys mouth and had him finger my ass but it was kind of out of my control. But it did get me wondering about what would it be like with a cock in there instead of a finger. Would it be as good for me as it was for all those ladies I'd done it to? The question played on my mind. There were mornings where I would wake up horny and start to stroke myself, thinking about different women, doing different things with them, and occasionally the thought of feeling a cock being slowly worked into my ass. And I'd usually come right then.
So I thought about it a lot. I decided that I wanted to try it, even just once to see what it was really like.

I went back to the dating apps. Searching for gay men just seemed wrong. I looked at the cross dressers and the trans people. I even hooked up with a couple of those but obviously I was the man and nobody wanted to fuck me. Finding a cock in a pair of panties under a slinky dress was quite fun though and I did manage to suck a few cocks and enjoy it.
Eventually I contacted a few guys. We talked, we discussed likes and fantasies, but I never quite went there.

Then one Sunday morning just before Christmas I woke up with a day ahead with nothing to do. And I was horny, so fucking horny. I lay there in bed stroking my cock thinking about different women, getting close to coming and then backing off, doing it again, over and over, and then my thoughts as usual would stray to feeling a cock about to enter me, but this time I didn't come.


I spent the morning mucking around but I couldn't get the thought out of my mind, so early afternoon I messaged one of the guys I had been chatting to and asked if he felt like catching up. He came back really quickly, said yes, so I jumped in the shower and then headed for his place. I got there, we met at the door, we shook hands which seemed slightly odd, and then went inside. I'd told him previously that my preference was to go straight to the bedroom so that's what we did.

We undressed and he was already hard. We reached out for each others cocks and started stroking. His was smaller than mine and he made quite a fuss of mine, then pushed me back onto the bed and started to suck my cock. I was a bit tense and nervous up until that point but there's nothing quite like lying back on a bed on a warm afternoon getting some really skilled head to relax you so I just went with it. It was great, he was playing with my balls, and the base of my shaft, and soon he put his fingertip on my asshole, worked it around for a few minutes and then put it in to about the first knuckle. The whole experience was just getting better, I wasn't giving him any attention at all, just lay there enjoying it.


Next he reaches to the bedside cabinet and gets some lube. He lubes his fingers and my ass, a lot of lube. I think it was 2 fingers went in quite easily, so he pulled them out and lubed his cock while I watched. Then he rolled me onto my side, came in behind me, put the tip of his cock up to my hole, and reached around aand started stroking my cock. This was getting exciting.

Gradually in time with his stroking he started to enter me, back and forth, a little further in each time. It was intense, really intense but it felt amazing. A few miniutes and he was fully in and sliding back and forward, stroking my cock. The feeling was incredible, just so fucking good. I was losing control of my breathing, it was all in time with his cock, and noisy. He was fucking me slowly for what seemed like ages but may have been only 10 or 15 minutes, I had no way of knowing. Then he pulled out and lay on his back, telling me to get on top of him.

He guided his cock into me again and this time I was upright on top of him and I was controlling how fast and hard I was getting this cock, while he was still stroking me. I started to get the feeling of coming but it was a long way off. It was familiar but different, building up slowly and more intensley. I don't know if it was his hand on my cock, or his cock on my prostate that was making it happen, but I could feel this mammoth orgasm building. I was trying to hold it back, holding back really hard knowing that if he came I could just let go and I would come too, but he didn't, and I couldn't hold it any more so I let it go. It was amazing, just fucking amazing, easily the best orgasm I've ever had. All I could do was just lie on the bed after for several minutes while he cleaned up the mess I'd left all over him.


Then we showered, had a cup of tea and I left. I think about that experience often, but I haven't been back. I've thought about it but I think that sex for me still needs to involve a woman to bring all of the feminine energy, the softness and beauty of a womans body. And kissing, kissing is magic but there's no way I could kiss a guy.


So where do I go now? I think the ultimate would be to find a male/ female couple where he is bi, and have a threesome where I have my cock inside her, and he has his cock in my ass, and we all have a really great time. I can't wait....

Published 
Written by Aldous64

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