(A) – This story contains anal intercourse.
(L) – This story contains strong language.
Part 1: Not for Us, at Least for Now
Part 2: Not Yet, but Getting Closer
Our second anal episode ended when we found we just didn’t have the know how to make it work.
Despite the failure to achieve anal intercourse, Ruby was content. To her, anal sex was not the be-all-end-all for sex, and our sex life was still great! Our variety of positional play in sex was still able to keep things plenty exiting.
For several months we refrained from trying anal play again, but Ruby, as always, wanted to satisfy my desires. She took the initiative herself and, without informing me, went through various literature on anal sex. She read about how to prepare her anus to make anal penetration more comfortable. She read about the sensations she could achieve and how to clean up properly both before and after an anal episode.
This was all unknown to me, but by some strange chance, I happened to read many of there same things. I found various material, books, and even videos online that gave advice on the subject. Virtually all of the sources had the same vital piece of advice: get your anus stretched and learn to relax those inner muscles.
As I read about this, Ruby actually did it. She kept a butt plug inserted much of the day, and every week she changed to a bigger size. In a period of four months, she had her anus accustomed to being stretched open quite a bit, and that gave her a big boost in preparedness for anal play. She also practiced breathing and relaxation. All of this I remained unaware of, and only came to know when she indicated she was ready.
That indication came when we went on holiday on a sea liner. On this vacation, we had agreed that anything goes.
The first night we had the most beautiful lovemaking. We did it in the shower, on the bed, and even on the low cupboards in our cabin!
She sat on the edge of the cupboards, fully exposing her pussy. I knelt in front of her and sucked and licked her to orgasm, as her head tilted backwards in pleasure. After her orgasms, we changed roles. I was erect again and pointing upright as I sat and she gave me a mythically amazing suck—something that is not unusual for her, because she’s very good at it! It wasn’t long and my second load of the night filled her mouth, which she devoured hungrily.
The second night we went for a special dinner. As we got ready, Ruby dressed up in a most provocative way. She wore a short, semi-sheer yellow dress which exposed almost everything. Underneath, she wore open crotch-panties, which partially exposed her shaved, completely smooth vulva. She looked incredible!
We somehow made it to dinner and through the meal without fooling around too much, but things began to heat up. We ended up finding our way to a show in the auditorium, but little of our focus was there. In the dim light, we had some cover that we took full advantage of. I fondled her wetness under her short skirt, while she used her hand to reach into my pants and play around with my hardness.
We were both hot and couldn’t wait till we reached the cabin. We departed the show at the end, but before we went to the cabin we allowed ourselves to be distracted, and we spent a few minutes in the lounge, where a disco was in full swing. We sat, chatted, and watched the other vacationers dance. One handsome looking guy sat down across us and we started a conversation. He politely asked Ruby for a dance, and we both agreed—on the condition that it was short. We had important business to get to very soon—private business.
Not long after, she was back from the dance floor, and we went directly back to the cabin. Something had set off the spark in Ruby, and the heat that had been building between us all evening was threating to get out of control. The instant we arrived back at our cabin, she ran to the bathroom. In a few minutes returned to the bedroom “starkers”—completely naked.
She ripped my clothing off and started sucking my cock. My fingers found their way to her pussy and it was already soaked and slippery. As I moved my hand and caressed her ass, I found her crack and anus was slippery with the familiar olive oil we had used previously for anal play. She had lubed her ass with so much that it was dripping.
As she felt my hand make its arousing discovery, Ruby climbed onto all fours on the bed, gripped a pillow tightly, then demanded loudly and firmly, “Fuck my ass!”
Without saying another word, she lifted her ass upwards and presented her self for the taking. I guessed this attempt might end like the others, but we were both so aroused that, with little hesitation, I obliged her request. I knelt behind her in doggy style and eased myself into her forbidden entrance.
To my surprise, it glided in very easily! Initially she did wriggle in pain, a little, but as I went I deeper and in, then began to thrust gently, she clearly began to enjoy it. Her exclamations were not of pain, but pleasure. She seemed to enjoy it so much that she just wanted more. I pushed and pulled, and soon felt her having the signature muscle spasms of orgasm.
“I’m about to cum!” I screamed.
She reluctantly made us slow down, and said, “I’m not ready to take semen in my ass. Pullout and spray it on my back.”
I thrust a few more times inside her amazing ass, then pulled out just before I ejaculated. Spurt after spurt drenched her all over, coating her back and gorgeous ass. Exhausted, we dropped flat to the bed. I lay on her back for a few moments, careful not to squish her too hard into the bed. Our sex-heated bodies were warm against each other, and the mess of cum between us was a sticky, wonderful mess.
Later, I asked why she didn’t want me to ejaculate inside, and she explained that since I didn’t have a condom, it would have leaked back out, and she wasn’t sure how to deal with that yet. We discussed this new kind of sex, and decided it wouldn’t be something we do all the time, but once in a while. My Ruby sure did her homework, and I am glad for it!
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