Jim and I had just shared an out of our minds 69 and were recovering when he had said he wanted me to fuck his ass.
This was music to my ears. I have fucked a lot of women in the ass and while some were much better than others one thing that always separated a "favor" ass fucking was the woman asking for it, and even better enjoying it. Some did it as a favor for eating or fucking them so good but it wasn't their idea.
In our correspondences we had discussed everything we could imagine to do to, for and with each other.
We talked about kissing and both were quite unsure, but we were doing that with no discomfort. We were actually doing it right then.
We are on our sides kissing passionately while feeling and stroking each others cocks. I was really getting into sucking his tongue while stroking his hardening cock. Being larger than me it was a new and exciting experience. I could feel him spreading his legs and pushing his cock towards me.
In our letters Jim had spoke of his reluctance to explore anything anal and I told him how hot it was for me. I always like to drift down to a woman's anus after making her cum once or more by eating her. There is something so forbidden, nasty but intimate about having my tongue in someone's ass hole while watching the expression on their face. To have them orgasm like Jim had done was so rewarding knowing I just shared something with another person for their first time. To complete the act by them asking for my cock in their ass is just perfect.
I have caressed Jim's ass with my finger tips and eaten him to orgasm and was so happy when he could put all his inhibitions away and ask for me to fuck him.
"Say it, say it again. Tell me what you want me to do with you. I almost came just hearing it." Was all I could say.
Pushing my crotch to his, our cocks now overlapping onto each others, I began a fucking motion between us.
Jim looked at me and said " Please fuck me, you have opened my ass to such new pleasures, complete me and fuck me."
I kissed him hotly forcing my tongue into his mouth and tried to eat him up. He sucks my tongue like he just sucked my cock.
I roll him over onto his stomach and start to caress his ass with both hands, spreading him open for my inspection. Putting my knees between his legs I spread him open. He spreads his legs even wider showing me how much he wants this.
I see him flexing his anus, it opens and closes invitingly. It is a darker color than his cheeks and almost the same as his ball sack which is pulled up tight to him. There are a few hairs around his anus and a fine line runs up between his cheeks. I think maybe he will let me shave this. I would let him do it for me. His cock is hard and points almost straight down and is bobbing up and down.
I have always loved this view, someone bent over spreading their ass cheeks open for me to see their ass hole. But this time there is a ball sack and hard cock under it not an open pussy.
I move forward kissing him right on the ass hole. I think he is so ready we don't need the usual preliminaries. I have just eaten him haven't I?
As I am spreading his cheeks and eating his ass, he moans and squirms.
Wetting my index finger I touch it to his anus and feel him flinch but almost immediately he opens himself up to my touch.
I am caressing him with a purpose but wait for him to set the pace. I tell him this. I say " Jim we will go at your speed, so relax. Hand me that Astroglide in the nightstand."
Jim gives me the lube and watches as I run a thick line down the length of my cock. I tell him: "don't worry this is for you.' as I show him my hand and it is covered with lube.
As I am spreading the lube all over my cock and stroking it I tell him: "Spread your ass open for me. Show me where you want my cock."
He does just that and there is his ass hole opening and closing, begging for my attention.
I run my wet fingers between his cheeks and let each dip slightly into his opening. With each pass I dip farther into his anus. Getting past the first ring is easy but I feel his inner ring tight and tell him to relax this will be like nothing he has ever experienced before.
I feel the first joint of my index finger in his ass, held by his ass hole but stopped by his inner ring. He relaxes and he pushes back and before I realize it I am into him up to the middle of my finger. He moans louder and deeper than before.
I know what he is feeling, having had a few fingers and some toys in my ass. But this is all new to both of us and I really want it to be perfect so don't move until I feel him relax some more allowing most of my finger in him.
I squirt some more lube on my finger as I pull it almost out of him. He says not to stop but I let him know what I am doing.
I can now finger fuck his ass and we are both getting into it. His anus holds me so tightly but yet he is opening to my touch.
I ask; " Are you ready for more?' He sighs: "Oh yea give me another."
I put a different finger in him insuring that it is wet enough for him. Removing this finger I put the two together and run some more lube over them. I see one of our towels on the bed and ask him to put it under himself hoping to collect some of this mess. I have found that the best anal sex is always pretty messy but so worth it.
I now touch both fingers to his ass hole and with little effort can push both slowly into him.
He moans; " This is unbelievable, I didn't imagine it would be so good."
I ask him if he is ready for another finger as I am now fucking him comfortably with the two.
He says; " No lets go for your cock, I want to feel your cock in me.'