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Cabin Party Part 2As we lay on the bed, silence came to our little group after Debbie announced her plan. I'll admit, my fingers kept a soft dancing motion over Cindy's clit and moist pussy lips during the moment. Debbie and Greg lay together, I could not tell if his cock was still in her ass or not. Greg reached around and casually played with a nipple as Debbie grew more enthusiastic with her comments. "It's really great, I feel good doing this, and I know it won't make me pregnant, so it is a great way to play together without worry. I don't know about you, but worrying about the rubber breaking and getting pregnant takes all the fun out of fucking."
Cindy didn't say much, but I could tell from the way her body was responding to my foreplay that things were going to happen. Cindy was drunk enough, that I think liquid courage was talking, along with a lowering of her inhibition from my previous exploration of her lovely ass crack.
Debbie smiled at me and said "I've watched, and you know what you are doing when it comes to making a girl feel horny, so this will be easy."
Cindy quietly said, "Will it hurt?" and Debbie answered, not if it is done right and you are really close to cumming. Debbie moved from Greg and came to the edge of our bed. She came up close to Cindy's face, gently touched it and said, "he's making you hot right now isn't he?" I kept up the play under her panties, moving along her pussy lips, sliding them apart. It was really getting wet in there. Debbie directed Cindy to flip over on her back, and have me take a position between her legs. I just about came when Debbie took hold of Cindy's panties and told her to lift her ass up. Debbie pulled the panties off for me, and that was one of the most sexy things I had ever seen.
Debbie then took charge of me. "Get your tounge to work, explore her, love her, make it gentle and soft as you lick the front." I did as directed, enjoying the sensations I was getting from Cindy as I flicked her pussy lips and clit with my tounge. This went on for a few minutes and Debbie spoke again. "Gently open her cheeks with your fingers, swirl the tip of your tounge all around her asshole in a soft circle."
Oh, how I had been wanting to do this to a woman. I had seen it on an 8mm movie reel that we had set up at a friends house one time. His dad had 8mm pornos and when they were out, he would invite us over to watch. Some of the guys had said it was gross to see anal, but I was enthralled. To now have a woman teacher, talking Cindy and I through it was wonderful. Cindy seemed to be getting in the mood, and relaxing. I think having someone take charge of her like Debbie was doing was having an effect on her.
Debbie whispered, "get your fingers on her mound, open her pussy up, lick her from the front, all the way to the back, and keep doing it softly, but quick." I followed the instructions to the letter, watching as Cindy started to tweak her own nipples and arch her back, allowing me to race my tounge down to her ass. I was in heaven! This was wonderful, and Cindy seemed to twitch and squirm when my tounge circled her anal opening.
I noticed that Debbie had walked to the corner, but Greg was still there. He had moved up onto the bed, and was watching with a smile. Debbie came back from the corner of the room with her purse.
She extracted a bottle of baby oil. As I kept up with my tounge, she started to drip baby oil on the very top of Cindy's pubic mound, letting the drips slowing cover the entire area. Debbie said, "hold out your hand." As I did so, she squirted the baby oil onto it.
"Now, move your tounge up onto her clit. concentrate on it while using your fingers and the baby oil to take over the soft circles around her ass." I pushed my index finger in towards the tight, brown opening and started to spread the oil about. Cindy moaned with pleasure and raised her ass up off the bed again. "This is so hot and nasty" she cried out. Encouraged, I applied more pressure with my finger. Debbie said, "that's it, let her relax and take the tip of your finger in her hole." It was amazing, the brown puckered area just started to open, allowing just the tip go inside, but then it clamped down, putting pressure on my finger.
Debbie said "move your mouth out of the way." As I pulled back, she squirted baby oil right on Cindy's ass and my fingertip that was now trapped. "Now, get back onto her clit, suck it, lick it, make her front part feel like it is going to explode!" I sucked and pulled her clit and some of her pussy lips into my mouth, licking hard, using suction to hold them inside between my lips.
I moved my finger so slowly, and it started to ease it's way inside further. It seemed warmer and hotter than a pussy, and much tighter. I couldn't wait for my dick to be in there, but Debbie was in charge, and I would wait for her instructions.
Cindy was really hot, her muscles were having spasms, it seemed. Her legs were twitching.
Debbie told me to get up. She spread baby oil on her hand, reached for my dick, and gave my already rock hard dick a few strokes to apply the baby oil. Debbie then told me to keep up playine with Cindy's front with my hand, and press the head of my cock up to her butt. "Now, slowly wiggle it up and down the ass hole, keep up the massage that I had you doing with your finger. Don't push it in! Go in circles with your dick around her butt hole."
Debbie looked at Cindy, and said to her, "ease your butt down onto him as he plays with you, it will go right in."
Cindy looked up at me and said" Don't hurt me!" Debbie told her, "you move into him, he will stay still, you take him in as slow as you want, but you get hotter and hotter for him to fuck your butt baby."
Soon, I had the same sensation on the tip of my cock as I had on my finger. It was wonderful. The night ended up with a couple of sessions of anal sex once I recovered.
A hot shower and lots of cuddling followed. Thanks to Debbie and a really drunk girlfriend not afraid to try something new, I got my first experience with anal.
End of Story