Sometimes a person will do something for me and I'm just amazed at how generous they can be. This happened to me last week when, after months of posting on a web board that I was looking for someone to provide Greek for me, my friend gave me a call and said, "Have you found your Greek provider yet? If not, well, you could probably talk me into it."
Before I get ahead of myself; when I'm referring to Greek here, that doesn't mean that I'm looking for a descendant of Greece. Rather, it's a shorthand parlance for anal sex. Certain things like "Greek" kind of make sense if you think about the historically held notion of philosophers as buggerers. Likewise with "French" loaning itself to oral sex. Yet, things like "Russian" (rubbing one's penis between a girl's boobs) and "Asian" (analingus) just leave me flummoxed.
I don't know what kind of things trigger a mood / catch a fancy but I had been of the mind that I wanted to bugger a woman again. I hadn't done it in years and enjoyed it greatly. I'm sure that some would say that doing this is a "power trip" and others would claim that anal sex is only pleasurable to men (either as givers or receivers) but I would counter that I've known many women that enjoy receiving anal sex -- either due to the implied power exchange or to the actual physical sensations.
Neither of these things seemed to be motivating my friend. Rather, she simply knew that I was wanting this, couldn't find anyone willing, and hoped to fulfill a desire. If that's not altruism, I don't know what it.
Fastidious to the point of being slightly obsessive, I was amazed that my friend would allow anything near her anus much less inside of it. The more messages I got from my friend as the week progressed before we met up, the more resolved she seemed. She had started off by saying that I could put a finger inside of her and see how that felt before moving into larger objects. Then the figure changed to a dildo. Finally, she told me that she was able, willing, and ready to take me inside of her. "This is something I want to try again. It's been years since I've done it and I know that you'll be nice about it."
Yes, I was gentle. She was nervous as heck when I arrived. "Now, how are you going to go about this? Are we going to do it first? Last?" I assured her that it really wasn't all that important and that if she was so nervous we could forgo any anal play -- "Oh, no! We're doing this. I'm set on it. I just want to know if you're going to do anything first. I want to get ready for it," she assured me. The logistics were giving her fits. She was so nervous about the anal sex being messy and wanted to be able to jump right into the shower afterwards. I couldn't help but chuckle.
As it happened, we kissed and cuddled for a while before we stripped and she allowed me between her legs to lick her to climax until she couldn't take it anymore. Afterwards she moved to the edge of the bed where she bade me to allow her to get me even harder with her mouth. It didn't take long until she was rolling a condom over my fully-erect member and slick up the rubber with some lube.
She looked up at me, into my eyes, and I could see that she was still nervous. I put my hand on her cheek and said, "If you want to not do this, I'll understand. This isn't a 'make or break' for me. I like doing anything and everything with you."
She stood up, putting her arms over my shoulders, and kissed me deeply. "This is something I have to do. I want to see if I can still do it and I trust that you'll go slow and will stop if I can't handle it."
"You have my word," I said before she turned around and got on all fours at the edge of the bed. One of my greatest fears is going into the "wrong hole" when I'm entering a woman so it was interesting to take aim and try to get into this orifice on purpose after so many years. I slid my finger in, first, judging just how much pressure I had to use to open her anus. She moaned and lowered her front half so that her weight went to her shoulders.
I pushed deeper with my finger, sliding in slowly before pulling out. I wasn't sure how long she was going to allow me access to her ass before she started to feel too self-conscious so I replaced my finger with my cock, aimed at her anus. Using the same amount of pressure, I pushed into her, opening her wider over the head of my cock. She moaned again, breathier this time. I waited, allowing her to get used to the sensation. Wordlessly, she nodded and I continued; moving deeper inside of her.
It was so unusual, being inside of her bottom. I thought back to the last time that I had done such a thing and that was a mistake. The last time I had anal sex, I had started to worry that I was taking too long to cum, and that going too long would hurt my partner. This planted the seed in my head that the same thing was going to happen again. However, looking down at her, I realized that she would have the courtesy to tell me if she needed or wanted me to stop and that I could fuck her for as long as I needed without having to worry. This put new steam in my stroke as I began doing more than just slowly moving in and out of her and, rather, began to fuck her.
"Oh, yes," she said into the comforter. Seeing the look of pleasure on her face and feeling her ass tightening around my cock. I put my hands around her waist and began pulling her against me as I pushed into her. I could feel the vibration as she fingered her pussy beneath me, her hand between her legs as I fucked her harder. Unbelievably, she started to cum again and as she reached her orgasm the pressure on my cock triggered my own orgasm. I threw myself into her, over and over again as I exploded inside of her ass.
I slowed and stopped, my cock still spasming as we both caught our breaths. "Is it okay?" she asked. "Is it all right for you to pull out?" She was concerned about anything that might be on the condom as I pulled out of her.
"Don't worry. It'll be fine. I'll slide out slowly." I did and grabbed a tissue to hide any "evidence" from her. I didn't want her to feel bad about anything. I disposed of that as she got up.
"It's okay if we cuddle some more in a few, right? I need to take a shower."
This sounded so much like something that I would say that I had to laugh out loud. "Of course. Do what you need to do to make yourself feel okay and I'll meet you right here," I said, patting the bed.
A few minutes later, we were laying next to one another. She was smoking a cigarette and I was nuzzled against her shoulder. Before I had a chance to thank her, she said, "Thank you. I'm glad we could do that. It really meant a lot to me. I won't be doing that all the time but that's something we can add to our repertoire. I'd like to have you do that to me again sometime... soon." I smiled and returned her gratitude, happy that she made this desire a reality.