The Most Sensuous of All Pt. 04

It was the moment of truth. Naomi was pinned face down on her bed with a large, soft dildo firmly wedged deep in her pussy as I straddled her rear end. The dildo was called Mr. Softee; it was obscenely large, just at the limit of what she could take, with ridged veins, and an outrageously large head, but in a slightly firm, but soft and comfortable phallus. She started squirming and moaning around this huge dildo as I reached for the KY jelly. It had been warming up in a bowl of hot water beside the bedside. I grabbed the KY and dried my hands off with the towel we kept with our "anal kit". Naomi issued another moan as she heard the click of the cap of the KY.

With panting breath I gently applied the KY to her rectum, slowly working a finger in and then replaced it with my thumb. I could feel the ridges of the dildo in her pussy. Then I pulled my thumb out and slathered my rigid cock with KY jelly as I taunted Naomi telling her that she was about to be truly and fully stuffed with cock. She whimpered and asked that I be gentle since she was not sure she could handle it. Of course, I needed no such advice since I was (almost!) always slow and gentle (thus my name).

Then I guided the glistening head of my cock, purple and throbbing to the entrance of her ass. I applied gentle pressure, going back and forth ever so slowly, working it in a few millimeters more each time. She was tight and stretched already from the dildo, but my cock head kept creeping in deeper and deeper. Eventually with a groan from both of us, the big head of my cock slowly slid past her ring. I was in! Amazing feeling. I held still for a breathless minute letting her get used to my size. It took all my self-control to ignore my cock which was urging me to drive it all the way in, but once I got the OK from Naomi I started to go slowly back and forth, giving her more and more cock until I was as deep as I could go. Then I pulled out a half inch and waited.

Here I was fully embedded in her tight ass but I needed let her get used to this double penetration. When I got the OK from her, I started to gently fuck her up the ass. I could feel the ridges of the dildo in her pussy.

Once she was used to that, brought to new heights of eroticism by giving her an outrageous double fuck. As I pushed my cock up her ass, I pulled the dildo partially out. As I pulled my cock out of her ass, I pushed the dildo in. In this way I maximized the friction for both of us. She was going wild, moaning and clutching the sheets and squirming. But things got even hotter when I reached around and fiddled her big clit while I was doing this. I must have been very athletic back then to manage all this at once, but I did. So back and forth with my cock and the dildo while going up and down on her clit. In a short while we both had incredible orgasms (hers first), the best orgasm of her life, me too. After she came she quickly pulled out the dildo in a rare example of sexual guilt--this was back before dildos went mainstream.

I was on a lunch break from work. I quickly washed up as best I could and returned to work smelling of pussy juice, cum, and KY jelly. I walked around in a daze and the women at work seemed unusually flirty. Could they tell that I just had the best sex of my life? I think that they felt it subconsciously. Of course, there is no way that I would chase another women because I was smitten by Naomi, totally satiated, and it was inconceivable to me that any other woman could match her.

We were to repeat this double fuck a number of times. I asked a lot whether I should get "all the gear", but many times she said no and it was just plain old-fashion ass fucking (hard to complain about that, eh?). It is difficult to believe that she would refuse anything sexual, but it added spice and variety to our love life because I never quite knew what was coming as I will describe in subsequent postings on this subject. Yes, seems incredible that two people could come up with new variations of anal sex after what we had done, but she and I were very creative.