STORY TIME: First Anal Experience

NOTE: to skip to the part of the actual anal sex, go to the 7th section down lmao 😂

Ok so my boyfriend was over this past Thursday night, which has become a regular thing this semester. The sex has been amazing lately, but the last time we’d had sex (Monday earlier that week) I bled all over him unexpectedly, as my period wasnt supposed to come for another few days at least. I felt really bad but he handled it like a total champ. Unfortunately, my period has been super irregular lately and my bleeding has been totally start-and-stop. Because of this, Id stuck to giving head most of the week just in case.

By Thursday night I hadnt bled at all in over 24 hours, so I was READY to get it in lmao. As foreplay, he rubbed and played with my butt forever, spanking me hard and then kissing my cheeks gently afterwards 🤤😍 He finally pulled me over to straddle his face, 69 style, except all the focus was on me 😏💦💦 The oral was incredible, as usual, and he added in the ace he’s been using lately, a finger in the booty 🤭 He refers to it as my ‘instant orgasm button’ 😅

After all that, he stripped down, stood at the edge of the bed and pulled me right to the edge and started sex as usual. It felt amazing, put a minute or so after we got going I started bleeding like crazy again!! He’s not a fan of the period sex, so we stopped and cleaned up (🙄🙄) and I finished him off orally. It was still a great night, but I was getting super annoyed with this quasi-period.

Fast forward a few hours and weve been sleeping and spooning, him in basketball shorts and a tshirt and me in just underwear, topless. We both stirred around 5 AM to adjust sleeping position and I somehow woke up outrageously horny 😳🙈 I told him how horny I was and to just play with my nipples, but we got hot and heavy fast and before I knew it his hand was in my panties, fingering my clit. I was squirming and moaning like crazy, and he pulled out his ace yet again (finger in the bootyhole) and I started coming like crazy and couldnt stop!!

When I was totally exhausted from the multiple orgasms, I laid my head on his chest and said ‘yeah theres no way were not gonna try anal, i enjoy the butt play too much’ and he replied ‘eventually or tonight?’ I almost fell off the bed!! Tonight?!?? I laughed and asked if he was serious about trying it now....he said he didnt expect it or ‘need’ to get off, but was definitely unopposed. At this point my mind was racing....it sounded totally crazy but I was definitely considering it 😯🤔😅

I reached around to tease him a little and he was absolutely rock hard, which made me horny all over again!! I mentioned that I did have a small bottle of lube hidden under the bed, a free sample Id gotten with a sex toy. Before I knew it, I had hopped out of bed at 5:30 in the morning to grab the lube and a condom!! I couldnt believe I was actually going to try anal on a total whim, so spontaneously, but I gave him the essentials and got on my knees, face down ass up, on the bed 🙈🙈🙈

He lubed me up, asked if I was sure and ready, and I braced myself for entry, grabbing the wooden edge of the bed, my face buried in my pillows. He went slow and gentle, eased himself in, and holy fuck was it one hell of a sensation!! I dont remember feeling any pain, just a bit of a forcing open and then a total, blissful fullness. After checking up on my again, he started to pump in and out slowly, a firm grip on my hips for stability and to guide me along with his rhythm.

After a minute of two or getting started, he asked if he could ditch the condom 😮😮 I told him that was his call, considering he knows where hes going lmao 😅😂 He pulled out, took it off and tossed it aside, and fuck the reentry was SO overwhelming in the best way 😍😍 We got going again and he asked permission to cum inside me. I gave him the green light and he went a few final pumps before pushing deep into me, leaning his weight over my back and coming in my asshole 🙊

When he pulled out, I think I was honestly in shock at what we’d just done!! He got up to grab some napkins and cleaned me up like the gentleman he is 💕 Laying in bed afterwards, he put some music on and we were both quiet, marveling at the step we’d just taken, both sexually and in our relationship overall. I sat up and looked at him, and he was starting to tear up!! I began to get emotional as well, and we just cuddled and giggled and held one another in awe. The feeling of closeness and trust and vulnerability was like nothing Ive ever experienced. The depth of our love and connection was palpable.

Overall, my first experience with anal was surprisingly spontaneous, but well prepped, and though I do/did enjoy the sensation of fullness that anal play and sex provide, the emotional aspect was everything and more. I didnt even really process the level of trust and comfort I have with him until thinking about it afterwards, how we were able to do something so vulnerable and scary in such a natural, exciting, mutually connected way. As someone who gets a lot out of butt play, the anal sex itself was pretty fucking awesome, but the emotional depth of the act that came from doing it the right way with the right person was the most amazing experience ☺️☺️💕