Cfnm Story Part IV – Home From Spring Break by Katrina
It was like an out-of-body experience, having a birds-eye view of fully naked Bobby masturbating in the sun for my smiling enjoyment. Any of my girlfriends would have given their left arm to see this. I couldn’t keep from grinning as I stood in the pool, to one side of him, almost eye level with his ball sack, as he leaned back and started to slowly jerk on his cock again. I had turned the radio off so I could concentrate on Bobby’s show. As I took in the view, I asked him if he could do it a little faster, jerk it a little faster for me baby, come on Bobby, that’s it.
He was obeying my commands and I was in hog heaven, knowing I was controlling him. Soon all you could hear was his hand slapping up against his swinging ball sack with the lotion on it. He was pumping it like there was no tomorrow now. His balls were swinging forward and backwards to the motion of his strokes. I could see from being so close to his dick that he was getting close.
His dark pink head was now engorged and looked like it was about ready to burst. Every once in awhile, he would look down and smile at me, checking to see if I was enjoying his show. (like what girl wouldn’t). I would just smile back and slowly nod my head up and down as to be telling him that he looks great pleasuring himself, and to just relax and let it go.
Then I did something that, to this day, I still can’t believe I did. I must of got caught up in the moment or something, because as I was standing in the pool, watching him masturbate, I reached around and started to grope his butt cheek and even run my fingers up and down his ass crack, still watching him jerk off. This sent him into overdrive, because he started breathing very deep and slowly rocking back and forth. With lotion on my fingers, I easily worked my middle finger in to his anus.
I had heard about this from other girls in college that a lot of guys love this when getting a hand or blow job. I could slip my lubricated finger in all the way to the second knuckle, and all he could do was writhe and moan, swaying back and forth, like he was fucking the air. Within about 90 seconds of me finger fucking his asshole, twisting it in as deep as I could and pulling it almost all of the way out, he then jerked his head back, and a stream of white cream shot out and landed in the pool at least 2 feet out. My jaw dropped as I thought to myself, good lord, what a load he had in him !
And it just kept spurting out, one after the other. I reached my other arm out in front of Bobby and caught a few squirts in my open hand, still keeping my middle finger on my other hand deep in his anus. Every time I shoved my finger in, another squirt would shoot out. I couldn’t believe the control I had over him.
After the last squirt shot out, I just shook my head in amazement and told him that that was incredible. I’ve never seen so much cum shoot out of a guy. He said it must have been from all of my teasing. I said it also might have something to do with where my finger still is. He blushed and said that it did feel awesome and that his ex-girlfriend used to do that to him too. I made a circular movement inside his anus with my finger and said, oh, so you’ve had other girls finger you too, huh?. Again, he just blushed, knowing I was still fingering and exploring his anus. I told him that my girlfriends had informed me how to finger a guy to give him stronger orgasms. He said that some guys don’t like it because they feel embarrassed about it afterwards. (idiots)
He suddenly sat on his butt and laid down on his back on the pool deck with his legs bent up and folded, like a women in the gyno position. I had to remove my finger when he did this, but I could tell he didn’t want me to stop fingering him. So I asked him if he wanted me to massage his prostate. He just grinned and said, well sure, but do you know how to do that ?. I grinned back at him and got up and moved to the other side and knelt down next to him.
But this time, I first stuck my index finger in his mouth to get it lubed. I held the back of his head while I pushed my finger in and out of his mouth. Then I looked deep into his eyes as I slid my wet finger in to his warm anus again. I could tell that even though he was finished cumming, the sensation was almost too much for him. He quivered as I slowly slide my feminine, little wet finger in and out of his anus.
I pushed my finger in as far as it would go, searching for his prostate. I moved it around, pushing it deeper and deeper, with him lying back moaning with his eyes closed. Again, I had to pinch myself. Here I was fingering one of the hottest guys in my high school class. I thought that maybe if I used two fingers instead of one, I might be able to reach it. So I moved in between his legs that were still wide open and slowly pushed the other finger in, allowing his anus muscle to slowly adapt to the wider intrusion. I could feel his anus muscle tightening, and then relaxing around my fingers. I think back now and remember how very warm and moist it was inside of him. How beautiful his little pink hole was, with little blonde fuzz that covered the back of his ball sack.
So now I had both my index and my middle finger deep inside of Bobby, and he continued to quiver as I pushed deeper and deeper. I noticed him groaning slightly with pleasure every time I pushed both fingers in to him. So I continued to double finger-fuck the boy for all he was worth. I was in a dream. It was almost more than I could take. After a few minutes, I told him that I wasn’t having any luck finding his prostate and that maybe he needed to get up on his hands and knees, with his ass in the air, so I can get a better angle at it
So he slowly rolled over face down, got on his hands and knees, sticking his ass in the air and putting his face on the pool deck. If anybody came home now, we would have obviously died of embarrassment. I positioned myself behind him and put oil back on my fingers again. I looked at the back of my house where I could see our reflection in the glass of the sliding glass door. I couldn’t believe it was me, fingering Bobby like a girl, with his sweet ass sticking up in the air. I put one of my hands on his ass cheeks to hold him steady. I told him to bear down, as I would probably be going deeper than any girl had gone before. He lowered his back, spread his legs even wider and said, “I’m yours, give it to me�.
I shoved my fingers in as fast as I could, hoping to at least touch his prostate, but still found nothing. He moaned out loud as my two fingers went in way deep in to his anus, all the way up to the last knuckle. I kept it in this deep, pushing them in as hard as I could. I even opened up my fingers and moved them around, trying to search for it, but no luck. With him in this position, I couldn’t help myself, so I used my other hand to caress his penis that hung down like a cow’s udder. And he giggled like a little girl when I tickled his empty ball sack.
When I pulled my fingers out, his anus remained slightly open about an inch in diameter, so I could peek in to Bobby’s body. He knew what I was doing back there too, as I looked into his opening. I couldn’t believe a guy would let a shy, college girl do these things to him, making him so vulnerable. I just stared in to his hole and shook my head in amazement. His ass cheeks flinched as I blew my breath in to it, seeing if I could make his hole twitch at me. ( I know, I know, quit teasing the poor boy )
Since he seemed to like it when I got aggressive, I slid my two fingers deep in to him again, and then I grabbed up his ball sack and made a little parcel package in my grip and gave it a tug. This caused him to tighten his anus muscle around my two fingers. I liked the feel of that, so I did it again. Repetitiously pulling back on his ball sack with one hand while I double finger-fucked his anus with the other hand. This action of me pulling his ball sack back at the same time shoving my fingers in to him as deep as they would go would cause him to tighten his sphincter muscle around my little fingers. I just thought this was simply awesome ! Pull and push, pull and push, I was loving it !
Part V to follow.
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