We had been together for about a month. The sex was fabulous and only getting better. We had learned things about each other that the other didn't even know. For example, I knew that her ass was very sensitive and that she wanted it to be touched.
She'd only idly wondered about anal sex before, until that first time I teased her ass while I was going down on her. She pulled away at first, but then relaxed and didn't withdraw the second time. I had waited until she was close to orgasm before touching her ass, so any additional stimulation was bound to feel good. I had been sliding two fingers inside her, but then wetted one in my mouth and shifted it back to press against her ass again. She pushed back against me and I slid it into her virgin ass. She moaned out loud and shoved her clit hard against my face. I fucked both of her holes with my fingers while she fucked my face with her clit. It was boisterous and great fun.
When it was over and she was laying back recovering, she looked at me and said, "Damn! I'm glad you didn't ask me before you did that! I might have said no!" I just grinned at her; it was all part of my wicked plan. She admitted afterward that I had given her the most powerful oral orgasm ever. From that day, she thought frequently about having my hard cock in her ass.
The next time we were together, I was taking her from behind and really enjoying the view of her ass and her back. She was really into it and grinding against me, so I knew this was a good time for my next step: I wetted my thumb and slowly slid it into her ass while I continued stroking into her. She gasped and arched her back, but then pushed back against me and rode both my cock and my thumb. She rarely came through penetration, but this was one of those times. She shoved herself back and forth so hard that I was merely holding myself still and absorbing her thrusts for a change. She cried out loudly while she came, as loud as I had ever heard her. Her response and vigorous movements excited me and I followed her into climax. We shook against each other and then collapsed together onto the bed.
"Oh my God, " she said, "I would never have guessed that could feel so good."
We got dressed and went out and acted civilized, pretending that we cared about something other than having sex with each other. We generally tried to leave the house at least once during the weekend in those early steamy weekends we spent naked together. The whole time we were out, I thought about what I would do to her that night and how to make sure she enjoyed it.
As I led her to the car to go home, I put my hand on her ass and gave it a squeeze. She looked significantly at me, then said, "You are such an ass man." I just laughed--she had me pegged.
We went through the door and headed straight for her bed; there was no need to discuss our destination. Our clothes came off quickly and she laid back and spread her legs wide, inviting me. She had begun getting wet on the drive home, knowing what was coming, so I put my tongue on her and tasted her wetness. I teased her for a while, taking her close to orgasm several times then bringing her back down, before I rolled her to her knees.
I began licking her clit again from below and brought her right up to the edge, then licked further upward to stroke my tongue across her ass. She almost jumped out of her skin, then settled back and pushed her ass back against my tongue. I fingered her clit while I slid my thumb inside her and continued to lick her ass, more aggressively this time. She reached behind herself and spread her ass cheeks for me, moaning loudly and tossing her head.
"Oh GOD I want you!" she cried out.
"Say it." I had never fucked with her mind before, but I could not resist this time.
"Please, " she said.
"Please fuck me in my ass!" she cried. That was music to my ears.
I stacked two pillows under her to prop up her hips and told her to relax her legs. One of my hands caressed her body, especially her lower back and cheeks, moving occasionally to her clit and swollen lips. I lubed two fingers of my other hand generously and started with just one, gently moving it into her ass and sliding it in and out. Shortly after, the second joined it. I took my time, allowing her body to become accustomed to, and to enjoy, the sensation of my fingers inside her. My other hand continually massaged her cheeks and lower back as my fingers moved slightly faster and deeper. I spread my fingers wider apart and twisted them, stretching her and stimulating as many of the aroused nerve endings as I could.
"I had no idea how good that could feel, " she breathed.
"Are you relaxed, baby?"
"As relaxed as I can be when I'm so turned on. I really want you inside me."
I smiled and shifted to my knees, bringing the head of my cock to her ass. I lubed myself liberally, stroking my cock a bit as I did so. I pressed gently against her, my hands spreading her as wide as possible. She stiffened slightly as I entered her and I stopped moving and massaged her again. I rubbed my hand all over her back and kissed her, talking softly to her the whole time. As she relaxed I naturally slid further into her without any effort.
It took me several minutes to move completely into her. Damn, she was tight around me! I lay on top of her, stroking her hair away from her neck and shoulders and kissing her. She turned her head enough for us to kiss very deeply for a minute, bonded together in a new and intimate way.
"How does that feel, sweetheart?"
"It's amazing. I think it's going to feel really good in a minute, just go slow."
I lifted myself off of her and began slowly and shallowly stroking into her. She immediately started moaning and I knew they were moans of pure pleasure. Quicker than I had expected, she was up on her knees and pressing her ass back into me, meeting my hips. I reached around her and placed two fingers around her clit, moving it side to side as she liked to do to her herself. "Oh GOD that's it! That's it! Fuck my ass!" she cried.
I was still trying to be gentle with her when she became insistent and started to shove herself into me harder and harder. Now I just relaxed and enjoyed myself, sure that she was enjoying it as well. She had a generous, beautiful ass. I had always enjoyed looking at it, but now seeing it around my cock was a treat for me. I put my hands on her sexy buttocks and rode her ass for a while, thoroughly into the moment.
She began tossing her head and hair about, almost grunting as my cock slammed home into her ass. She was clearly approaching an orgasm, which was a very welcome surprise. I kept up exactly what I was doing and held off my own--this took some doing because watching her and feeling her virgin ass squeeze so tightly around my cock had me so very excited. She was normally very expressive in her climax, but this time was amazing. The orgasm took her by surprise and she screamed out loud, screaming almost in a wave as she came for what seemed a long time. This was too much for me and I released myself inside her in hot spurts, grabbing her hips in my hands and yanking her body against me. We thrashed about against each other, nearly delirious as we climaxed together. This was the first time I experienced strong aftershocks from my orgasm.
I fell forward on top of her and we lay together, completely spent. Her throat and shoulders were flushed and her breathing was ragged. I stayed inside her for several minutes as we relaxed and I held her. I could feel my pulse in my cock because it was squeezed so tightly inside her and my pulse was so strong. As she recovered, we kissed deeply and intimately before I finally removed myself from her as gently as possible.
She became a fan of anal sex that day, saying that it was the most intimate experience she could imagine; I was grateful many times afterward that I had invested the effort to do it properly.
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