Nervous girlfriend shares first time anal experience

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. After a few minutes I told him I was ready. He pulled the butt-plug in and dipped his tip into my hole stretching it significantly wider than the butt-plug had. I yelped from the pain asking if it was in. He assured me it was just the tip but he would go slow. I continued to whimper the pain consistently getting less bearable and my eyes watering uncontrollably until I cried for him to stop. He pulled out immediately and we stopped. I apologized and explained to him that I didn't think I could do it. I put my robe on and went to wash my face, my mascara had run from the tears and I looked like a racoon. For the next few months I kind of gave up. I'm just a tiny girl with a tiny asshole. Anal just wasn't for me. One night, while staying at Sam's I couldn't keep myself off of him, I climbed on top of him and I wanted him to get a good view of my ass bouncing up and down on top of his dick. I sat in reverse cowgirl and worked his cock to give him as much pleasure as I possibly could. He slapped my ass with an open palm. I moaned, as much as I love it when he's a sensitive caring lover, I love it even more when he is aggressive taking what he wants and maybe even hurting me a little in the process... in a good way of course. I want it. I crave it. This time he did something a little different though. He didn't give me another good slap, instead I suddenly felt a pop and this thumb circled around the inside of my ass. I was now riding both his throbbing cock and his thumb. My breathing became shallower until I let loud a series of loud cries while my body released itself with pleasure. After that, anal was on my mind again, and this time I was going to do it right so that not only could I give Sam the pleasure that he deserved from my tight hole while getting another intense orgasm for myself. I wanted it bad. So I googled positions and what I could do to make it better. I told Sam what I wanted and used it as dirty talk while we had a quicky before going to sleep that night and an excited glimmer sparked in his eye. After we finished I told him it wasn't just talk, I was serious and exactly what I wanted to him. The next evening we went to dinner with some friends knowing full well what we would be doing that evening. It was hard to focus because I was so turned on by the taboo (in my mind) thing that we were going to do, but I had a couple drinks to ease my mind and hopefully loosen me up a little. After we left dinner we stopped at the adult store on our way home, a little buzzed I flirted with him while we looked at the walls of toys and helpers on the walls and shelves. We made fun comments about the products and tickled each other as we joked. I loved shopping with him in this store. We got to the anal play section and looked at the different sets of trainers settling on a set of 3 different sizes their tips tapering from small to larger, the largest one being about 1.5 inches at the base. I grabbed a douche, I was familiar with it vaginally, but I'd never bought a re-usable one before, and we also purchased some more numbing cream called tushy-tamer as we were going to his place not mine that night. When we got home I excused myself to the shower with a bottle of room temperature water and the douche and ran myself a warm shower. I put my hair up as not to get it wet and filled the douche to the brim. I squeezed lubrication on the nozzle and inserted it into my anus letting the water fill my cavity. I squatted in the shower and waited for my body to naturally expel the water. It felt like my backdoor was spitting. I repeated this as directed until the water was clear, and honestly until I felt clean enough to do it. Already I was feeling more confident going into my next sexual encounter with anal. I took some of the Tushy-Tamer and rubbed it both around and as deep inside my anus as I could. I wanted to give it a chance to work before it was time. I sauntered into the room lit by a dull lamp wearing only my nightgown. Sam greeted me by slipping his hand under the lace and cupping my plump breast. He squeezed it so my nipples protruded out further before pushing the fabric to the side. He began sucking on my nipples. I love sucking his cock so I sat down on the side of the bed and slipped his boxers down to reveal it standing upright. I put one hand around it before taking it entirely in my mouth. I hit the back of my throat hard over and over again so it felt like it was about to bruise. He pushed me further onto the bed and I lay on back pulling my knees up higher to reveal my anus. He took his thumb and rubbed inside my soaking wet cunt while he reached over to the nightstand where the three anal trained were lined up by size, waiting to be inside me. He went to grab the first one and I stopped him. It wasn't much bigger than his thumb or my first butt-plug, I was sure that I would be able to take that one no problem and I guided his hand to the larger one. He looked at my like he was asking if I was sure and I nodded. He smirked took his thumb out of my pussy to grab the lube and started lathering the medium sizes trainer up. He gently put it against my hole and slid it in slowly. It only hurt for a second and it was in. He then saddled up between my legs and grabbed his hard cock. He slapped it against my pelvic region in anticipation before putting inside my warm pussy. He whispered about how badly he wanted his cock inside my tight little ass while pumping inside my pussy. He didn't cum. Instead after a few minutes he slid out and I flipped over into doggy. He took the medium sized trainer out and I asked him to put a bit more of the Tushy-Tamer in before filling me up again. He complied. After a moment I felt the trainer insert back into my rectum. I cringed a little as it felt like it stretched more in this position but I took the entire thing. "That was the big one," he said. "Are you sure?" I asked. "Uh huh," he assured me "and I'm not much wider than this, so you'll be able to take me once you're ready." I let him work it allowing the muscles in my ass to adjust to the stretching from the movement before he pulled me down onto the bed in the spooning position. He handed me a blue vibrator with a nub for clitoral stimulation and I turned it on starting to work on myself with the largest trainer still inside me. He took it out, it making a popping down as it quickly exited me. It was barely a second before he thrust his cock into my slightly more gaping backdoor. The sensation was different than the trainers. It wasn't painful like the first time we tried but it was still uncomfortable like it was rejecting it. It felt my asshole was a cobra squeezing its prey. He moaned whispering how tight I was and started to pump. I cried between heavy breaths and my body couldn't decide between pain or pleasure. As he went faster I turned the vibrations up on my toy until I came first a hollow feelings in my pelvis creating rippling waves throughout my body as I loudly expressed my orgasm. Seconds later he began to cum. I could feel it more than in my pussy if cock feeling like a subtle hum inside me while it hot cum exploded inside me. He didn't pull out right away. Instead he held me as I contemplated how I had just lost my anal virginity and how I couldn't wait to try it again.

Amy

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