“A Night of Double Penetration”

I have been asked both about whether Cindy is into anal sex, and whether I have been involved in any double penetration with her. I initially wasn’t going to document the following event, simply because it involves our friend David and I have written about a couple of our times with him, but I will share this to satisfy those who requested.

It was a fun night for us all the way around. It began with Cindy, David and I going to see a trio of metal bands at a local venue. We were really enjoying the show and David had been very generous with buying drinks. I had to keep a fairly clear head as I was driving, however both he and Cindy were getting hammered. The following day was the start of a holiday weekend and the mood was right for fun.

Cindy, of course, had dressed to kill with a tight leather mini and a black tank top that, once stretched over her boobs, became very thin and in the lights from the stage; you could make out the shape of her tits. She had on a pair of stay-up thigh high stockings and her black dominatrix heels. I call them that because they had all sorts of buckles and zippers on them and looked like something a woman with a whip would have on.

I loved standing behind her as she moved her body to the music. It was always fun to have her shake her ass and rub it against the front of my pants. I was having a great time and started to get a little stiff. I know all the guys around us, and even the guys on stage were checking her out. At one point the singer for Armored Saint pointed to her and mimicked raising a shirt. She shook her head but he kept it up and she relented. She pulled the tank top up and flashed him and everyone around us.

I was really enjoying this and took the opportunity to reach around and grab a couple of handfuls. She pressed back into me, so I knew she enjoyed the attention as well. After the show we three piled into the car and headed for home. As you know, after a great concert everyone’s adrenaline is pumping making us all excited. David kept teasing Cindy about flashing but said that he was off to her side and behind her, so he didn’t get the chance to see them very well. He continued to mess with her until she finally got on her knees in the front seat and turned towards the back, raising her top again.

David and I started whooping and hollering and I reached out to pinch her nipple. He saw this and tried to do the same but she shrieked and pulled away. We continued on home, with me trying to get her to flash people on the way. It didn’t happen, but it kept the mood to an elevated sexual level.

When we got back to our place, I cranked up the music and we all continued our party. I was ready as I couldn’t drink too much earlier. Cindy had slumped down onto the couch and I could tell the drinks had really gotten to her. She had that glassy far off look to her. When she began to relax, she started to let her legs fall open some. David and I had a great view up her skirt and could see the tops of her stockings and the smooth creamy flesh above them. I told her that she was giving us a nice show and she smiled and parted her thighs even more before closing them.

I could tell she was in a playful mood and kept up the sexual banter, sometimes getting a mischievous smile from her in return and a little peek for both David and I. David decided to mess with her, so he jumped off his chair and sat down onto the floor about two feet in front of her. She just laughed and teased him with by opening and closing her legs a time or two. I grabbed us all another beer and then sat down next to her on the couch. She leaned over onto me and sort of slid down a little, surrendering to the alcohol I suppose.

We continued to talk and I began to rub her thigh with my hand. I watched as David’s eyes followed my fingers as they stroked up and down her thigh. Every so often I would pull it up further and mover her skirt up slightly. After several minutes I had her skirt up and over the tops of the stockings. She leaned in to me even more and I heard a moan escape from her lips. I asked her if those shoes she was wearing bothered her and maybe she wanted to take them off. She just said yeah, that would be great and started to lean over to take them off.

I pulled her back against me and told her to hold on. Then I told David to go ahead and pull them off for her. She sat back and stuck one leg out, putting the shoe right in front of him. He undid the buckles and removed the straps. He then pulled the shoe off her foot and began to rub her stocking clad feet a little.

“MMMMMM that feels good” she said, “now do the other one.” With that she switched feet and stuck the other out for him to pull off that shoe. While he was doing that, I slid my hand further up her leg until I was stroking her bare skin above the stocking tops. As David began to stroke her foot, she leaned back even more and started to sigh. I watched as David moved from her foot onto her calf and continued to massage it.

The further he moved up, the further I did as well. By the time he was past her knee, I had begun to stroke the outside of her panties. She slid down a little further and opened her legs wider. Basically she was giving us the green light to continue. He scooted closer so that he was kneeling between her legs. I could see his eyes focusing on my fingers as they danced across the front of her panties. I could feel the heat through them and in only a few more minutes, I could feel the dampness as well.

When I moved my hand up to the top of her panties and began to slip it inside, David then moved so that both of his hands were stroking her thighs all the way up to her bare skin. I looked over to him and told him my hand didn’t have very much room and could he help me out. He slid his hand up the outside of her legs until they were on her hips. When she felt that, she raised her hips up to make it easier for him. He then grasped both strings on her panties and began to pull them down.

As I continued to tickle her clit, he pulled them down below her knees and she lifted both feet to allow him to pull them completely off. He was now sitting a foot in front of her as my fingers began to dip inside of her. I know he could see them moisture clinging to them as I pulled them out. She began to slowly push back into my hand and small little moans were escaping her lips.

I made eye contact with David and nodded, then moved my hand up under her tank top. He wasted no time in leaning forward and touching his tongue to her wet pussy lips. She now started to moan even louder and in short order he had his face buried all the way into her crotch, licking her for all he was worth. With me stroking her nipples and him licking her pussy, it wasn’t very long before she began to shake and was ready to cum. She grabbed the back of his head and wrapped her legs around his back and pulled him in tight as her orgasm washed over her.

As she began to come down, David continued to lick her while I had her lean up so that I could remove her top. I went back to giving her nipples attention, but this time it was with my mouth. She grabbed me by the hair and I wondered if she had a handful of David’s as well. We soon had her on the verge of another powerful orgasm. This time when she came she screamed out and pushed us away from her body. She then reached over and began to undo my pants.

I told her to hold on a minute, and then stood up, pulled her up and as I took off my clothes, she undid her skirt and began to slide it down her legs. She looked at David and told him to get his pants off. When I was naked, I pulled her down onto the floor and had her straddle my cock. She reached back, grabbed it by the base and pointed it at her hole as she lowered herself onto me. David moved around to the side and she took his dick into her mouth. She licked and sucked on him like a woman possessed.

We continued like this for several minutes when she took him out of her mouth and looked up at him. “I want you both in me.” I love it when she gets so turned on like this. Typically she doesn’t let me have anal with her as I have a larger cock. David was closer to 5-1/5” inches so she enjoyed not only sucking on him, but also having him in her butt every so often. He stepped back around to her rear and began to get her ready.

As he was licking her and sliding a finger in and out of her, she was kissing me while I was asking her “Are you ready for us baby? Are you ready to have two cocks in you?” “ mmmm yeah baby, I want you both in me. I want to feel you filling me up real good.” My cock was getting so hard by this. I could feel his finger moving around inside of her while I stroked in and out.

David moved into position and placed his dick up against her little rosebud, as he was pressing in, it must have been very slippery, because before any of us knew what was happening, it had slipped down and as he pushed in, I felt it slip into her wet pussy along side of mine. We all stopped and she yelled out “Don’t stop, just fuck me.” He pushed in all the way.

Unless you have ever experienced a double pussy penetration, you have no idea just how incredible it feels. It immediately feels like someone has wrapped their hand tightly around your dick and beginning to squeeze. It took a little bit of work, but soon we had all fallen into a rhythm where he was stroking out and I was stroking in. She was going crazy and moaning and yelling how good it was.

“Oh God Yes……oh fuck…….so full……….so full………..mmmmmm……keep pumping me……….oh yes………..” she kept up talking as she was getting closer and closer to cumming. Her voice was getting higher and higher and soon she was screaming out that she was cumming. Both David and I continued our stroking and trying to stay inside as she was thrashing around. As she began to come down, David slipped his dick out of her and pressed it into her ass in one long stroke. This sent her over the edge again and she was soon babbling incoherently as she came again in less than a minute.

She collapsed onto my chest as we continued to poke in and out of her. I was ready to shoot and I grabbed her shoulders and pushed her down hard onto my cock. I could feel David’s cock through the thin wall separating her pussy and ass. I gave into the sensation and was soon filling her pussy full of a big load. David grabbed her hips and began to pound into her hard as my cock began to shrink. Just as I slipped out of her, he rammed in hard and bellowed out that he was cumming.

We all collapsed on the floor and caught our breath. Eventually I regained enough strength to pull out the sleeper sofa and we all climbed on. It was a little tight with the three of us, but at that point we didn’t care. I woke up once about 5:00 to take a piss and came back and had a nice slow screw with Cindy as she was semi dozing. At about 7:00 I woke up to her facing me grunting as David was fucking her from behind.

She looked into my eyes and said “He is in my ass…..mmmmmmmm”