How I Lost My Anal Virginity

You could say I’m a conservative kind of girl, I don’t smoke, or dance close to anybody, and I don’t do things or wear anything that might look too sexy or sensual. After being raised in a very conservative home, anything sexual-related was still taboo when I left.

Eventually, I truly got to understand my taste and the things I liked once I started living in my own house, and I discovered this side of me that truly liked being dominated in bed. There were things I was very curious about but too ashamed to explore and one of those things was anal sex.

After seeing several women in a couple of porn videos achieving anal orgasms, even squirting, while being pounded through the back door, I began to wonder if it truly felt as great as it looked, and the more I thought about it, the more it excited me. But like I said, being raised in a conservative way really left me with a very large degree of shyness, and I wanted that to change.

While I drowned in my shyness, hiding my greatest desire from Josh, my boyfriend, I did my research and I could say that I know everything there is to know about anal sex, you have to be very relaxed so it doesn’t hurt when you’re penetrated, lube is mandatory or it won’t work, and you have to be clean if you know what I mean, I even secretly bought one of those enemas you can fill with water to clean up the ass, just in case it ever happened.

My desire was so great that Josh knew something was going on, he caught me in our bedroom staring at the enema, and when I realized he walked in I quickly hid it under the pillow.

“Beth, what are you doing?” he said frowning, he had seen me hiding something.

“Nothing,” I said, smiling nervously.

“You’ve been acting weird for a while now, what’s going on?” he said sitting by my side.

I wanted to explain it all to him but I was so embarrassed, I didn’t want him to think I was a slut or something. After stuttering a bit, he slid his hand beneath the pillow and pulled the enema out.

“What’s this?” he asked and I blushed so badly, that I felt my cheeks starting to burn

“It’s an… enema,” I finally said, Josh remained silent and then I continued, “I’ve been curious about anal sex, I just didn’t know how to tell you that I wanted to… you know! this is so embarrassing baby!”

Suddenly he looked very relieved, “Oh fuck! I thought you were cheating on me!”

“What?! No! I love you, baby, I would never cheat on you,” I said right away.

He then wrapped me in his arms and held me against his chest, “baby, you know you can tell me anything, always! There are no secrets between us.”

I felt so ashamed but excited at the same time, “I’m sorry.”

He kissed me so gently and so reassuringly and without warning our kiss became passionate, feeling his tongue against mine gently massaging it was pushing the right buttons. I moaned into his mouth and then he looked at me, “So… how about you go into the bathroom with this and we explore that thing you’re so curious about?”

Never in the time that we’ve been together had he said anything to me that got me incredibly horny as it did at that moment. I practically ran inside the bathroom, got rid of my clothes, and filled the enema with warm water. I cleaned the insides of my back door with it, and feeling the warm water running inside of me felt very nice.

Once I was ready, I put on my underwear and I stepped out of the bathroom and found Josh already in bed, wearing only his trunks and waiting for me. He placed his hand in the empty space next to him and made a gesture to me, I slowly walked towards him, I felt so nervous and excited at the same time that adrenaline started running through my veins.

Once in bed we started kissing each other, I felt the weight of his body over me, warming me up as our tongues tangled and massaged each other. Josh started caressing me and touching me without going to the obvious places right away, which only made me feel more anxious. Suddenly he turned me and I straddled his face, we started doing a 69, he licked me as I pulled out his delicious cock from his trunks.

Then I felt his tongue moving slowly inside my slit completely blowing me away, just knowing that his cock was going to be inside my ass very soon had me already wet. Josh licked me and tasted me like never before, his cock felt so hard beneath my fingers and against my tongue, we remained fixed in this position for a while, making each other feel good and getting carried away.

“I wanna be inside you now,” he said right after I gagged on his hard cock, I think it drove him to the edge because I felt it twitch inside my mouth. Josh moved from beneath me and I remained in a doggy-style position, then he got off from the bed and stood behind me.

The fact that I couldn’t see what was going on made me anxious. Then I heard him taking the lube from our bedside table and the cold slippery liquid sliding down my tiny asshole and slit. I gasped when I felt him spreading the lube with his cock, teasing my ass, and then penetrating it with his fingers, preparing me.

I tried to stay as relaxed as I could as I began to enjoy his fingers inside me, then he stopped, “Are you ready?” he asked me and I nodded. Then I felt his head pushing against my ass, there was some pressure but it didn’t hurt, it felt very nice. “Oh fuck,” he grunted and then he started moving, I gasped feeling his cock stretching my ass as it went inside slowly.

Josh spanked me as he moved, going in and out of me, his pelvis slapped against my buttocks and I never felt so turned on in my life, I knew I wouldn’t last long having him fucking my ass. He kept a steady rhythm, the sensation was so different, so good.

I moaned loudly as he gripped my hips and started pounding me faster, he pushed me against his pelvis, getting it all inside, taking me to an edge I never went to before. Before I knew it, I was already moaning my orgasm out, my whole body quaked beneath his cock, I never felt my pussy so wet. Then Josh released his orgasm inside my ass, moaning and grunting so loudly. I’m pretty sure he enjoyed it as much as I did.

We did it again that day, and the day after, and now anal sex has become a regular thing in our lives, and I must say, I can never get enough from it.

Authors note: I love anal, it’s one of my favorite ways to enjoy sex and I know some people are still wary of it. There’s nothing to be worried about, take your time and enjoy, just as the protagonist did in this erotic story. Do you like anal sex? – Tamsin 🍑

I'm Tamsin (also known as Tammy), I'm the writer of all of these erotic stories. I write what turns me on and it used to be just for my personal use, but I decided to release it publically. I hope you enjoy and if you do remember to leave a comment and if you want more become a private member. If you want to know more about me, this is my personal page.

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