Getting ready for anal first time

Whenever Dani and I agreed on an idea the path from planning to execution was swift. Anal sex was no exception. For a while we continued to practice, or to be more specific, my ass kept getting fucked by progressively larger dildos. Often Emily wore the strapon and Dani was just a spectator. But my sister was not always available, so my girlfriend fucked my ass just as often. It turned out that with proper preparation and lubrication my anus could accommodate really impressive sizes. When we moved to large sized dildos I started using anal plugs. I would insert one into my anus some time before the pegging. Even the small-sized ones helped to prepare my ass significantly. My ‘boyfriends’ were all hung, but I was confident that I could comfortably take them all; not necessarily at once though. We also kept inviting the boys for blowjobs. Dani loved to watch as I sucked cocks and swallowed the cum, I loved doing it. The sex the two of us had afterwards was always incredibly pleasurable. You could say we had the most unique kind of foreplay.

At least once a week, usually more often, one of the four men: Max, Eric, Ricky or Brad, joined us for the unusual threesome. We did not mention the anal sex to any of them until my training was complete. We did not want anything to ruin my first time with a man. Unsurprisingly our first choice was Max, my sister’s boyfriend. Emily commented that she had been waiting for that moment, but remained silent, because neither of us mentioned the subject either. She was always present, whenever I sucked Max’s cock, so obviously she would witness him fuck my ass too. For this occasion I inserted a moderately sized anal plug into my ass a whole hour earlier. I wanted Max to be able to go in smoothly.

“You know, little sis,” Emily told me, “I’m glad that you turned into such a slut.”

I grinned in response and she continued:

“And a brave slut at that. I would never let Max fuck my ass, he’s too big for me. He already stopped asking, but I know he’s a bit disappointed. You’ll be the little butt-slut for the both of us. Just don’t use up his entire stamina. I need him for myself too.”

“Don’t worry, sis,” I replied with a broad smile, “we have other boyfriends too.”

“Four in total,” Dani added, “such harem should be enough to satisfy my slutty girlfriend,” she said, hugging me.

I enjoyed anal sex in itself, but the experience was the more pleasant the more feminine I looked and felt. For that reason I did not want to be completely naked and wanted to wear at least some sexy lingerie. A pair of sheer white stockings and a lace bra in a matching colour did the trick.