He Won the Toss - My Turn Now

This is the continuation of "He Won the Toss" which was posted last week, a non fiction story about a trip to the nude beach early summer of 2024 and where it's gone from there. Please comment if you enjoyed the read.

So he won the condom toss last week and our meet was a blast. The Holiday Inn he chose for his day worked so well I booked the same room for my meet this Sunday.

My requests for him were similar, be cleaned out for a good ass fuck with a fresh change of clothes and not to forget his cock rings he enjoyed so much. I also asked him to shave around his asshole and anywhere else he wanted but his asshole needed to be smooth. I'd have my little bag of tricks waiting for him this time.

I greeted him at the door wearing jeans and a sport shirt. He was again in shorts and a fishing shirt which didn't hide his swollen cock.

I asked that he shower up using the scented soap I had brought. He asked if he could just use the room soap as he didn't want to go home smelling suspicious. I agreed but asked that he still clean around his backside really well.

I found it funny that although this 'outing' was to be all about me, he was the one that was going to be treated like the winner. I liked it then and I like it now. Giving enjoyment to another is much better than receiving and I was also ready to do some things for the first time. We sat down in opposite chairs stroking ourselves stopping on occasion. Knowing someone just a few feet away is watching you jerk off gets me hard fast. It wasn't long before we each had a raging hard-on.

I went to the door and got the collapsible luggage rack from the closet area and had him sit in it spreading his ass cheeks as he sat on the two nylon straps. I had a perfect view with complete access to his asshole, cock and balls. He was also about to find out how great a slow delicate prostate massage feels.

I gathered up a few pillows from the bed and a throw pillow so that my mouth was comfortably against his asshole. I then pushed my tongue into places I never thought it would be. His ass was shaved smooth as I kissed and licked the back of his balls occasionally penetrating him with my tongue. His moaning was nearly non stop and I loved hearing it.

As I was licking and sucking I asked for the bag on the desk next to him. Without missing a beat I had my fingertip vibrator on and was applying some lube. Using the massager I started into his entrance and once in, I very slowly I felt around finding his prostate. I ran the vibrator around both sides of it slowly rubbing. Then I pulled out, turned the vibrator on and went back in to finish the job I had started. Since my mouth was now unoccupied I slid my body up a little further sucking on his balls and licking the underside of his cock. Each time I saw him start to touch himself I would have him move his hands away.

I thought he was probably relaxed enough now for me to insert two fingers so I started alternating between vibrating his prostate with a finger or massaging it with two. He was feeling incredible. I backed away from his cock for a few minutes and watched the cum flowing from the tip and he hadn't had his orgasm yet. I was thrilled to see him dripping so I could lick it off as it came out. I began to massage his prostate a little harder and had him to the point that with every two or so rubs of his gland I would have another few drops of cum to taste.

I didn't want him to orgasm yet and I was far from being done. I asked him not to move as I got out from under the webbing then kneeled in front of him. My vibrator went back in his ass and his cock went in my mouth until I felt his shaved balls hit my chin. I was taunting him as to what I was going to do next. I was having so much fun hearing him moan I didn't want to stop.

I took his cock out of my mouth and my finger out of his ass and asked him to put on his cock ring. Did I want to cum in his ass or mouth. Where did I want to have him cum? I knew he liked to rim me so I bent over in front of him and let him have his fun. From behind he stroked my cock slowly as I reached into my bag of tricks and pulled out my butt plug asking him to lube it up and put it in me. He did but in the process he played with it in me for a few minutes. I finally decided enough was enough and couldn't hold back any longer.

He turned around and bent over with his legs spread as far as was comfortable. He was saying he wanted to be fucked hard. I shot some KY in his entrance and put my lubed cock against his asshole and pushed. It nearly went all the way and with the second push I was in as far as I could go. I just stood there for a minute to feel myself in his warm ass. It was great. I started fucking him and he'd move his ass around a little changing how my cock felt entirely. It only took a few of those moves until we both realized I was about to cum. I could feel him clinch his ass against my cock draining it entirely. We had barely stopped when I asked him to stand up and face me. In seconds I had a finger massaging his prostate again with my other hand cupping his balls as he fucked my mouth. He came with his cock in my throat. I could feel his asshole start to flinch as his cock began throbbing.

We were both done and exhausted.

He started off to the shower and I joined him. We made sure each other were spotless head to toe as we discussed where our next meet might be. I think we decided on the next one being an outdoor event. We just haven't decided where or when yet.