Jay Taught Me

The day I really learned to fuck a love anus.

I had made a couple of hookups, before meeting Jay, but they were mostly, cuddle, kiss, and blowjob sessions. If I was lucky, I might get a 69 out of it.

So, Jay wasn't my first male sex encounter, but he sure was the most interesting. He was well educated and somewhat debonair. He had a soft approach to sex that I have tried to adopt, and it really works very well. In fact, that day, he got my virgin asshole.

Jay was a senior man, like me, early 60's, stocky, but not fat. He kept a beard but it was short and well-trimmed. His hair was more salt than pepper. He was average height, always well dressed and clean.

He was a widower and I was welcomed at his home. The bedroom he had shared with his wife was off limits. We always played in the guest bedroom. He kept a stash of toys, lubes, and poppers, if needed. But, aside from the lubes, we never used them.

The first time we hooked up, he taught me the soft way to approach fucking a love anus. After the usual foreplay - the hug & kisses and exploring caresses; after the 69 blowjobs, he began. As he worked on me, he talked in his soft low voice.

As I lay on my back, he was lying between my legs, and he was sucking softly on my dick. He moved his arms to hook my legs at the knee and started to bend them back.

"If I push too far," he said, "Let me know. I don't want to hurt your back" He licked his way down my dick to my balls. Just using his mouth, he manipulated my balls sack, so he sucked, a little bit on each ball. Then he moved on.

"The secret to a pleasurable fuck," he said, "For both the fucker and the fuckee is to start softly. I could just lick around your asshole and lube it a little and began to thrust. You would probably be receptive and after a bit, even start to enjoy it. But, I want to make sure you enjoy every step of it from the beginning."

With that, he began to lick around my anus, and as he did, he talked. "The anus is full of nerves, but they are very defensive nerves." He had my anus well lubed with his saliva, and was just tickling it with his tongue. "If I just started to thrust," he said, "The nerves would cause the anus to close against the intrusion. Now you may well know how to loosen up so the entry is not painful, but it's better if we make those nerves happy."

He started to put pressure on my hole with the tip of his tongue, making little jabs at it, as well as doing a little more rimming. Before I knew it, his tongue was slipping past the first ring, and he began to thrust a little harder. He pulled back a little and said "Just like that, I've caressed the nerves and soothed them and soften them. Now I can move in."

He leaned in and, with a couple of licks around, his tongue speared into my anus, reaching almost to the second ring. He tongue-fucked me for a bit, leaving me moaning, before pulling back to breathe.

"Now the nerves are happy," he said in his low voice, chuckling. "Look out asshole - here come's my finger." He leaned back in and I felt him licking around. At the same time I felt his finger slide in past my anus and slowly move up through the second ring. He pulled it back and started probing until he found my g-spot. He began to gently caress the prostate, causing my cock to harden slightly and me to moan.

"Many folks," he said, "rub the prostate thinking it will give the man pleasure. Unfortunately, they are rubbing too hard and it actually causes pain and discomfort. One must caress the gland, lightly and gently. As you can feel, that causes the greatest sensation." He was right I had never felt such a sensation. A doctor, probing your prostate, is a bludgeon, compared to what Jay was doing. A bead of pre-cum began forming at the end of my cock. I heard Jay's low voice saying, "Now to go for the stretch."

His finger slid slowly out of my asshole and started to slide in again, but this time there was the thickness of two fingers. The asshole accommodated the two fingers quite easily and Jay used the two of them to play with my love button. He then started to fuck in and out with his fingers increasing the tempo as he worked. "Now, I can add another finger but that is about the same diameter as my cock, so let's go for it". As he said that, I, unconsciously, clamped down on his fingers. He chuckled and said, as he continued to stroke some more, "I thought that might happen. While your love anus is ready, your mind said, Whoa!" As he stroked I was loosening up again.

Then he pulled his fingers out to the tip. I felt a re-arrangement and then felt the thickness of his cock head probing my asshole. The head popped in easily, before I could react. "Push against it", he said, "Try to push it out like a big dump." I reacted to that and felt his cock slide in all the way. His ball sack bounced off my ass. I felt like I was being stuffed, but he started pulling it out slowly. He pulled out till the ring of his cock was just inside my asshole, then started pushing again.

The nerves around my asshole were going wild. The feeling of his cock head and the veins of his hard on sliding across my prostate were making my own cock bounce. He started a slow fucking motion seeming to drive deeper with every thrust. As he increased the tempo I clamped down a little. I wanted my asshole to provide him as much pleasure as he was giving me.

"Oh Yeah!" he said, "I like when you tighten up like that. My cock was dripping precum, constantly, now. Jay's tempo was increasing, and I found myself pushing back at him, with every thrust. "Wait", he said, as he pulled out of me, and my asshole felt empty. He lifted my legs high, pulling my ass off the bed. He jammed a pillow under my ass and I felt his cockhead back at my asshole. This time he slid in easily and started a quick thrusting fuck.

His hands came down to my cock, using my precum as lube, he started to jack me off in time to his fucking strokes. We were both soon moaning with pleasure as the sensations from his hand job had my asshole tightening & loosening as my climax was building. "Oh God, Jay!" I cried, and he laughed and cried "Oh yeah, Man, Me too!"

My balls finally let loose on of the strongest orgasms I've experienced in years. Not long after I started shooting, Jay jammed his cock in as far as it would go and I could actually feel the throbbing pulses of his cock shooting cum into my ass.

After he was done, he kept up a slow stroke as his cock softened. He let it fall from my asshole and fell forward on me. We enjoyed some passionate kisses, as we held and caressed each other. Our bodies were sliding together in the cum I shot all over my stomach.

As we lay together, coming down from our excitement, he asked "So, was it worth it?" I almost giggled like a girl. "Oh, yeah, that was awesome." I said.

"And now you know how my virginity was taken." he said. "The next time, it will be your turn to practice what you learned today on me."

"When will that be?" I asked.

"Well", he said, "Unless you're in a hurry to leave, I suggest we try the shower, in the bathroom, clean out and we'll see what pops up." We both jumped off the bed and headed for the bathroom.

He actually made me practice a couple more times that afternoon, just to make sure I got it right.

NOTE: Jay & I were both certified disease free. Make sure the anus you want to practice on is too, If you can't be sure, use a condom.