My friend Amy took her first cock in the ass dry while she was camping. I always thought that I was sexually adventurous, a slut perhaps, but I was amazed when she told me. I loved getting my ass eaten out by my partners but I was convinced that my backdoor was too tight for any man to put it in me no matter how big his cock was.
Enter Sam. Sam and I developed an incredible relationship and he quickly took me from being promiscuous to taken. I was surprised I didn't miss being single, but it probably had something to do with the sexual chemistry that we shared.
One night, early in our relationship, we laid in bed talking about our past sexual encounters to try and get to know each other a little bit better. He told me about his experiences with Anal. He told me about one girl in particular who went crazy for it, they had hooked up a handful of times and it was almost exclusively anal. He told me based off of his experience with women that it would be a whole new kind of orgasm for me and that I too wouldn't be able to get enough. Just from talking I knew I wanted him to be the one to take my anal virginity. He was experienced enough to trust, plus the way he talked about it made me wet.
Well-endowed is a great description word for Sam's cock; Long and thick enough to challenge my deep throating skills and sometimes forced me into a gag. It occurred to me that this might be an inhibitor in this new sexual adventure through the backdoor. I never thought a cock being too big could be a problem.
My first anal adventures were solo. Mostly watching porn, trading in my usual lesbian girl on girl top picks for a combination of amateur, low production, and high production videos. I would get out my pink butter-fly kiss. My go to toy, being the first toy that I had ever purchased and have since bought multiple variations of would slip inside my satin pink cunt while I pressed play on the computer. I'd watch video after video. Although hot in their own way, a concern raised in my mind, every one of those girls assholes easily sliding open for girthy cocks viciously pumping in and out until both man and woman cum in loud sexy unison or the big hard cock pulling out for her to jump up and finish him off with her mouth. My ass most definitely could not do that, at least not yet. I already owned a butt-plug from my online shopping sprees; small for the most beginner of beginners. It sat in my toy chest untouched next to a tube of numbing cream. I took the cream and gently rubbed it on my anus before inserting the butt plug. It took a lot of effort, but I got it in with little to no pain and the first hint that this might be a pleasurable experience. That combined with my trusty butterfly-kiss putting pressure on my soft vaginal walls and fluttering against clit. I came harder than I had in a long time. If it was as easy as the videos made it look and as easy as this felt… then what had been stopping me all these years?
Finally the moment came to try it out with Sam. Logic had it that I should do it exactly how I had done alone, but slide out the butt plug and replace it with Sam's huge cock. We lit some candles and Sam reassured me how sexy I was. He started by eating me out, sliding down between my legs where I was freshly waxed he warmed me up by stroking my pussy with his talented tongue and sucking on my clit. He flipped me over and swirled his tongue around my ripe virgin asshole before putting on the numbing cream and inserting the small hard butt plug. It hurt more than I remembered it when I was alone. Sam grabbed my butterfly-kiss for me and let me start to play with myself while he worked my ass with the plug.