Cindy’s First Time – first time anal

Cindy was sleeping fast while I undressed and got drunk in bed, trying not to wake her up. She had planned a romantic evening together, but, being on call, I ended up working well after midnight on this Friday. I knew I had to do something special to catch up with him the next night, but all I really wanted to do was sleep. I closed my eyes and drifted quickly.

At one point during the night, I woke up. I turned around to snuggle up to Cindy, who was lying on her side with her back to me. I could smell his silky nightgown. Without seeing him, I knew it was the red that barely covered his. She was naked underneath, which started to light me up.

As my cock began to get hard, I started slowly pushing against her ass. After a few minutes of that, I was hard rock. Cindy was starting to wake up and slowly pushing back. I reached my hand around and cuped his chest. I could feel her nipple hard through the silky fabric. She let out a little moan just as I felt her hand come back to catch my dick. Her hand found her way into the front of my boxers, and I helped her by pulling them down just enough for spring my free cock.

I backed away Cindy to give her room to stroke my cock, and my hands wandered her sinuous figure as we continued to lie on our sides. I ended up working his nightgown around his hips. It’s normally when Cindy roll on her back and make me ride her missionary style.

Instead, she worked my dick’s head up and down between her firm ass cheeks. She was taddling me, that’s for sure. In the ten years we have been together, Cindy had not been receptive to trying intercourse. We’ve had a few play a few times, but nothing more than a bit of external stimulation and digital penetration on each other.

My pre-cum was plentiful and, conveniently, a good lubricant. Cindy continued to caress my cock while rubbing my head up and down between her ass cheeks. She began to work in a circular motion, eventually settling on her little tight pleater. She arched her back, pushing her against me. I pushed back and felt the tip of my dick slip partially in Cindy was gently panting and letting go of my dick. I pulled his hips towards me and felt the head of my cock erase the tight ring of his sphincter muscle. She was still gasping, so I pulled out. It made Cindy shudder, just the way you do when you have a sudden thrill.

I grabbed the lubricant tube from the nightclub behind me. I squeezed a few in my hand, and stroked my dick a little. Cindy had rolled on her back, and I moved more kneeling between her legs as they opened up and wide. She started rolling her clit/face with her fingers and told me to keep going. I moved in, rubbing my dick against his tight little hole. I gave a little boost and I could feel my cock forcing it to open. I felt my head clear his sphincter again and slipped into deeper. She was very tight and warm.

I started slowly and built some steam that Cindy could tolerate. She was working her clitoris with her little chrome ball that I received all my length inside her, pulling all the way back before diving again.

Cindy started to cumming hard, which pushed me over the edge. I felt my balls tighten, and my dick got more congested. I slowed down my pace, but eventually passed the point of no return. I pushed a little further and started pulling my load up Cindy’s. I pumped until my dick slipped, followed by a lot of cum. I was just a little shocked to have taken Cindy’s cherry. I never thought she would give that up. After our shower, we went back to bed. I was asleep in no time.

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Cindy’s first time