Not Yet, but Getting Closer (A)

(A) – This story contains anal play. 

Part 1: Not for Us, at Least for Now

After our unexpected first attempt at anal intercourse, Ruby and I began to discuss something that we had considered taboo up until this point. We never were really into the anal thing before, but now we started to dance around the subject.

I think at some level, I had been interested in this for a while. It only became a conscious thought and spoken desire on that night we first tried, but there were signs before. Sometimes as we engaged in foreplay, I would just naturally bring my penis towards her anus. She never complained, but sometimes playfully asked, “What you trying?” or “Do you enjoy doing that?”

Often I would admit, “Yes, it turns me on.” But thereafter we would indulge in normal sex episodes, and nothing more would come of that anal curiosity.

But at some point, that changed.

One evening, a little while after our first attempt, Ruby actually suggested something surprising. She said if I wanted to, she would allow me to try to take her anal virginity. She had read about it in the time since our first attempt, and although it could be still be painful for her on the second try, she was willing to try it again.

I thought about it, and finally gave her the thumbs up. We decided to try that night.

She asked me to grab some baby oil and lube her thoroughly, then we could give it a try.

We got everything ready, but we soon discovered that the baby oil wasn’t the right kind of lube for this particular adventure. With my very large and excited erection, and her tiny, virgin ass, all these factors made penetration impossible.

We decided to change lubes, but couldn’t find the one we bought for our previous anal play night, so we had to stop our play and go get more.

Ruby got out of bed and, like our last sexy errand, she slipped on only a short dress which would expose her lower half if a light breeze blew the wrong way!

She said, “Let’s go! The lady at the drug store can give us some advice.”

I knew that Ruby and the drug store lady were friends, but if Ruby was going to her for advice on how to open up her ass for me, then apparently their conversations had gone farther than I thought!

I dressed as well, then we drove off.

We decided to stop for coffee, and as I got out of the car at the coffee shop, Ruby got out too and followed.

“What are you doing?” I asked.

“I… want coffee?” She said hesitantly, confused why I seemed confused.

“But you’re nearly naked!” I looked pointedly at her barely-clothed lower half.

Realizing what I meant, she smirked at me. “No one cares. Besides,” she said as she gestured to her beautiful body, “all this belongs to you. If others want a view, they’re welcome to it, because they aren’t getting anything else.”

I just smiled.

I must say, she probably attracted a lot of attention. After getting our coffee, we headed to the drug store. Ruby went in alone to have a “more private conversation” with her friend. After a few minutes of seeking advice and making a purchase, Ruby came back out with a pack of condoms and a container of olive oil, which was apparently the recommended lubricant. We drove home eagerly, ready to start playing again.

We made it home, bolted inside, stripped off, and were back on the bed in barely a minute.

We put down a towel to minimize the mess of the oil. Then Ruby knelt on the towel and presented her gorgeous ass to me so I could begin preparing her. I drizzled some oil into her crack, savoring the erotic view. I spread the oil with my fingers, then slowly inserted one into her ass. It went slowly, but she slowly loosened up and began breathing and moving sensually, enjoying the play.

I rolled a condom onto my very-ready erection, then rested it against her well-lubricated ass. I checked that she was ready, then began pressing in.

She winced as my cock stretched her open further than my fingers had.

I was gentle, moving back and forth slowly. We made a little progress, but I still couldn’t get the whole head of my cock into her tight, virgin opening.

We tried for a couple more minutes, until she finally yelped, “Ow, ow, stop, it’s too painful.”

We were both still so horny, but we could tell that I wasn’t going to get into her ass tonight, so we switched to something tried-and-true.

I pulled back from her ass, removed the condom, and shoved my cock into her vagina instead. Immediately, we both groaned in satisfaction at finally joining our bodies. It wasn’t the anal intercourse we’d hoped for, but it was still beautiful. As worked-up as we both were from attempting anal sex, we both climbed to the peak almost instantly.

“I’m about to cum,” I told her.

“Cum on my face!” She demanded.

I knew of her desire for this. She’d told me before that she wanted “a mess on her face,” but the sudden demand sent me over the edge.

In the last few seconds before I came, she pulled away from me, spun around, and stroked me firmly while she mashed her clit with her other hand.

That was all the encouragement I needed. I instantly squirted all over her cheeks, nose, lips and chin. She moaned as I covered her, and she began to orgasm too.

Both breathing hard, we kissed and shared some of the “mess” I’d made on her face. We hugged and cuddled close, not fully cleaning up the mess we’d made on her face, which had also spread to other places.

Before we fell asleep, she whispered, “Give it time. Soon you’ll have my beauty hole!”

We hadn’t succeeded at anal intercourse yet, but we were getting closer, and we still had an amazing time of lovemaking.

And she was right. Soon, we would succeed. And when we did, our sex life would become a whole new ball game!