A First for Him

I am easily intimidated, especially when I feel like I don't know what to expect. I only enjoy new things if I am with someone I trust completely, with them the vulnerability of trying something for the first time can be romantic and downright sexy. With a stranger or even a new relationship, new things make me uncomfortable, nervous, even afraid. I need to know they'll listen to me if I am not enjoying it, you know?

Although, I have to confess ... I get off on being the more experienced one in a situation. It's why I've always valued being someone's first. Their first kiss, their first lover, all the firsts. The level of enjoyment does depend on the person, of course, but I have found the vast majority of my inexperienced partners to be eager to please, and more importantly, ready to listen to instruction.

Anyway, on this particular occasion was his first anal sex. I was introduced to anal many years ago by my first long term boyfriend, and I have enjoyed it with a few other partners. I've not done it for a long time though, and never with someone with a larger than average dick, so it was with some trepidation that I oh-so-elegantly proposed to my current lover, "Do you want to fuck me in the arse tonight?"

I've known for a while that he's never done it, but has wanted to tick it off his bucket list. I have been planning on offering for a while, but life is busy and plans always get shifted, and this is definitely not a spur of the moment kind of event, so I asked him in the morning, and he agreed.

I quietly made plans and preparations. It was exciting to think about it all day, by evening I was so turned on, just at the thought. After dinner I showered and didn't bother dressing, just threw on a soft lounge robe before he came over.

We hung out on the couch for a while, watched a bit of netflix and had a cuddle. Gradually a cuddle became a bit more handsy. He stroked my hair and I snuggled into his lap, running my hands over his sides, and his thighs. I could feel his cock harden in his jeans, so I undid his fly to release it. I love his cock, and I love the little noise he makes, without fail, the first time I take it into my mouth. He's got a long, girthy dick, really wide. It's gorgeous. I definitely can't take the whole length in my mouth, but I make a good effort, and make up the difference with my hands.

I moved to kneel in front of him and he took off his pants completely and sat on the couch. He held my hair back as I slowly and gently licked his shaft from base to tip. Softly I took the head into my mouth, swirling my tongue around it, then flicking across the tip. He groaned, and tightened his grip on my hair. Happy to oblige his unspoken request, I leaned forward, letting his cock slide deeply into my mouth. Stroking the base of his shaft with my hand, I sucked on his cock, taking it deeper and deeper. He started pushing the back of my head down, enjoying fucking my face. I suck his cock until I'm short of breath. When I can't go on any longer I suggest we move to bed.

My robe seemed to vanish on the journey from couch to bedroom. It was a cold night though so we snuggled up under the blankets. I took a moment to talk about what was ahead. I made sure there were condoms and lube within arms reach. We agreed that I would set the pace, and I didn't mention it at the time, but I still had my doubts that it would go smoothly, simply because of his size.

We didn't jump straight to anal though. First we got back to making out, kissing like teenagers, warming the bed and ourselves up again. I love the way he kisses me, like he's tasting me, always wanting more. He lay on his back and I was above him. He squeezed and sucked my heavy breasts, flicking my nipple with his tongue and biting them just enough to make me gasp. I straddled him, wanting so badly to have him inside of me. I like to pause when his dick is juuuust touching my pussy, so he can feel how wet and ready I am, and I just look at him. Sometimes I make him wait, only the tip of his cock inside of me, barely moving, hardly even breathing while the suspense builds. I always expect him to grab my hips and pull me onto him, but he never does, it's a little disappointing, I would love that. Instead, he waits me out, and I watch his face as I ease myself down onto his cock, as I think he is watching me, too. His dick always hits me deeper than I expect, and the shock of it against my cervix sends a thrill up my spine. I lift me hips, gently thrusting myself onto him while we kiss each other on the face, on the mouth, the neck, it doesn't matter, our lips are everywhere while I fuck him. Gradually my climax builds, and I can focus only on moving my hips, grinding against him while he was so deep inside me. One hand pulling my hair back, he tells me to come for him, and he bites me on the neck. Finally, with a deep, loud, moan, I came, and it was amazing. He held me deep and fucked me hard while I quake, my pussy dripping.

When I recovered I climbed off him, and knelt to his side. I couldn't resist licking his cock, I love how it tastes covered in... well, me. After a quick lick I turned to kiss him so he could taste it too.

He had sneakily grabbed the bottle of lube, and while I was on my knees beside him, sucking his dick, he reached behind me and started fingering me. I gasped as he ran a digit over my asshole. I don't know how he does it, but he manages to thrust fingers into my pussy while also rubbing my anus, it was a fantastic feeling. He even managed to get a finger onto my clit as well, all with one hand. It's magic, probably, or feels like it anyway. Must be the long fingers. He uses a little lube and gradually slips a finger or thumb into my arse. At this point I've given up on giving him head, as I am too distracted, so I am just draped across him, my butt in the air. I certainly didn't notice how cold the air was anymore.

He had his thumb in my arse, at least two fingers in my pussy, and he started thrusting into me at a slow pace. Ín time he managed to get a finger onto my clit as well, and every touch to that sensitive nerve bundle made my legs twitch and shudder. I felt like a puppet, with no control at all, and I loved it. He kept it up until I came again, moaning against his side and clutching at him. I told him I was ready to be fucked in the arse, if he was. I sat up to give my knees a rest while he sorted out the condom.

I knelt in front of him and leaned forward on my elbows. He took the time to generously lube up my ass and his dick, and I was so excited by the anticipation that I reached back to play with myself, rubbing circles on my clit while he played with my asshole. He rubbed the tip of his dick against it, then he lined it up, ready. I told him told hold still (Well, I may have gasped "Hold the fuck still and dont fucking move," but I can't be sure.) and I gradually eased myself back onto him. My worry was for nothing, as after a bit of pressure his cock slipped into my arse like it was made for it. I loved the intense feeling of my tight arsehole stretching over his big dick, and I almost couldn't believe it was that easy. I moaned a loud "YES," giving him permission to fuck me. He held onto my hips and started to fuck my arse, Keeping it slow, thrusting all the way in and out. I could tell he was leaning back and looking at his dick in my arse, and I wished I could see it too. I fingered my pussy, and I could feel the wide girth of him from inside my vagina.

I worked harder and faster on my clit, really wanting to get off while he was inside my arse. He fucked me harder, pushing his hands down my back as I cried out, "Fuck me oh god fuck yes!" It didn't take many more thrusts for me to climax, bucking against him and feeling moisture from my pussy drip down my hand. We slowed down after that, I was getting a little sore. I knew he would have loved to come inside my arse, but also that he was unlikely to do so while wearing a condom. So he took it off and it was finally time for me to get off my tired knees, lie on my back and get fucked.

Fucked I did get. He started slow, and kissed me while sliding into my drenched pussy, but soon he was fucking me hard and fast and I knew he didn't have long left. I held him tight, digging my fingernails into his back, and begged him, "Please, please come inside me, I want you to come in me." Fuck I LOVE when he pounds me that hard, like he's out of control. Soon he came, his body clenched and shook and he collapsed on top of me.

I am never sure what I should do for him in that instant, whether to continue grinding against him until he's completely finished, or if he wants to be stroked or kissed while he is essentially immobilised. I must remember to ask him before next time. In any case, I love the heaviness of him after he comes, like he has completely relaxed, all tension gone. I feel like we react completely opposite post coitus, he just about passes out, while I am energised and awake, like I've had two shots of good coffee. I am also overwhelmed by affection, so after we clean up and put on cozy pajamas I just wanted to snuggle against his side like a happy limpet, while he reads a book for a bit before we go to sleep.

Well I hope he enjoyed his first anal sex. I definitely had a damn good time. Were you counting? I got off at least 3 times. I asked him if it lived up to expectations, but he hadn't known what to expect, apparently. That's one way to avoid disappointment, haha.

I don't know if we've got many other firsts to try together, but I'm sure we'll think of something.