A young man gets a big surprise after a girl at the beach offers him his first anal sex
By: Date: 2024.03.05. Categories: Sex Stories Tags: , , ,

I couldn’t believe what she had just told me! This was so HOT! How lucky could a guy get! At least that was kind of my thinking as the petite bikini clad brunette just ahead of me led me through the dunes of swaying beach grass. The trail was now passing through a thicket of tangled and stunted evergreens and was now so narrow we had to go single file. This I didn’t mind at all since I loved just watching the motion of the girl’s poorly concealed butt cheeks as she walked. And soon I’d have the opportunity to do far more with that lovely bottom than look at it!

We met in the afternoon when Deb had asked me to help her spread some sunscreen on her back which of course I accepted. The feel of her soft young skin was amazing and we had started chatting. She was very easy to talk with and our conversation rambled all over the place. I don’t how it got there but somehow we got on the topic of sex. For me it was literally a “stimulating” discussion and my efforts at hiding the bulge in my speedo were failing especially when anal sex came up. “Would you like to try it? Would you like to have anal sex? “Hell yeah!” I said with probably too much obvious enthusiasm. “Get your stuff and follow me, I’m staying at a relative’s beach house, we can do it there. I promise you’ll have butt sex within the hour but you have to trust me and do what I tell you.” she said cheerfully. I agreed and could hardly move fast enough!

A few minutes later we entered the bedroom of an older but still cozy beach house of average size. We wasted no time getting out of our swimsuits and were now naked. She was really cute and I could hardly wait. Then she suddenly excused herself and said she would be right back and zipped out the bedroom door. She returned a couple minutes later with a big tube that said KY on it and a, BLINDFOLD?! “Remember, I promised you anal but you have to do everything I tell you.” And with that she tied it securely over my eyes. “This girl is kinky! I like it! I thought to myself. She guided me onto the bed and had me lie down on my back. Nothing happened for what seemed an agonizing minute or two then I felt the mattress respond to the weight and motion of her body climbing onto the bed.

Warm hands caressed my body starting with my limbs and working toward my torso. A tongue flicked against my nipple till it stood erect then repeated this with the other. A finger, with the lightness of a feather, traced my groin to my crotch and started massaging my balls and penis. It squeezed the soft bulb of the tip and grasped the shaft gently but firmly. Eventually the hand was replaced by what had to be her mouth! It went deep into the throat as it sucked and worked my cock with ever increasing intensity. Deb’s voice said, ”Bring your legs back to your chest, you’ll love this.” I did as she said, I mean why not, everything had felt fantastic to this point so my trust was complete even though I felt rather vulnerable in this position.

Something lightly flicked against my balls again then traveled lower and lower down my perineum. She wasn’t going THERE, was she?! YES! She was! The tongue started flicking against my butt hole circling patiently in tighter and tighter circles as it spiraled sensually toward the center. With each orbit it felt better to me. Then it licked me hard in the very citadel of my privates. Mentally I was taking notes so I could pleasure her this way.

“Want more?” she asked. “God yes!” I burst. Then what must have been a finger entered me! Yeah! THERE!. It was a very strange but powerful erotic sensation as it was moved within me. Before long another joined the first and for the next few minutes pleasured my behind like nothing ever had! I could hardly wait to fuck this girl!

“You have two big surprises coming. You’ll be getting them soon!” Deb teased. “Just relax as much as you can, here comes the first one.” I was so lost in my lust and the sensations I was feeling I wasn’t thinking clearly. Then something far bigger than a finger started pressing against my anus! What was she doing! It must have been some kind of big toy or I thought. Whatever it was, it was making progress and was bordering on being painful. Without the slightest warning the intruder suddenly stormed the threshold of my resisting flesh and slid with sensual ease into the far reaches of my rectum! It felt AMAZING! So concentrated had I been on this erotic and exciting pleasure I only slowly became aware that my ankles were now resting on something big and warm.

Then I heard Deb’s voice again, “You like that DON”T YOU?!” It was like my brain had just switched off its higher functions and I was now in primal mode so all I could do was grunt “YES!” The thing was moving back and forth in me now and feeling fantastic as Deb said, “Great, time for your next surprise, ready?” If the coming surprise involved even more pleasure I thought I might die! But I said yes anyway. I was still on my back with my legs up when suddenly the blindfold was removed. Total shock swept over me! Instead of the delicate, feminine features of Deb’s face I saw the rugged squarish, very masculine face of a, a, MAN!!! “WHAT THE HELL!!!” I burst. “Just relax, you just said you liked it!” deb reminded me. I couldn’t believe this was actually happening!

As though being jolted out of a lust filled trance my eyes began to wander about the room trying to fit all this into some kind of context. Looking to my left was just what I was looking for. The vanity at the wall had a large mirror that presented a perfect side view of my mostly smooth, smallish body with my legs over the shoulders of a bigger, older guy who was stretched out above me in kind of a push-up position pumping his big cock in and out of butt! I wasn’t gay! Not even in the least! So, why was I LOVING THIS?!

“I love being in your ass! You’re a great fuck! Let’s try a different way.” the guy told me in a deep voice. He put me on my hands and knees with my legs bent a little and quickly entered me again. “It is SO HOT watching you guys FUCK!” Deb gushed. Then she moved closer, grabbed my wobbling, erect cock, and started masturbating it. The guy started thrusting in me even harder and soon announced he was cumming. His hands gripped my haunches firmly, his dick pulsed within me, and I felt his semen squirt forcefully into my bowels! With Deb’s hand still cranking on my dick it was just too much and the load from my penis shot across the bed! It was the most powerful orgasm I’d ever had!

As we cleaned up Deb said “This is Rob, my oldest cousin. He loves fucking guys so I thought I’d help him with that. You have to be more care about not assuming things. When I promised you anal sex I never said it would be with me or that you would be doing the penetrating! I’ve been careful to nail down the details ever since and I still love anal sex, giving, getting, guy or girl!

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