Jen’s University Chronicles Part 12-First Time in the Bum [F/F]

Hey guys, Jen here! Sorry for the delay in writing…the rush towards finals is completely real and you know, school over sex stories. Butttt tonight you get a good one…the first thing to go up my butt ;) we both had a lot of fun with the Ask us Anything post last night and I’ve pinned it to the top of our page, so if you have anything you want answered, that’ll stay up forevaaa! Lol seriously, as always, hit me up in the comments, DMs, the AMA post, anything. We’re always happy to chat or reply! Hope you enjoy tonight! ♡Jen

We find ourselves coming down the wire towards the end of our very first semester of college, Nick and I were kinda sorta dating/more like fuck buddies and I was still learning and growing with Emily. I asked Nick what he wanted for Christmas since we were in the awkward are we dating or just fucking idk and he was like “I don’t need a present, I want your butt”….okay, save me some money, let me think about that one. I’d obviously had him do the whole “thumb putting pressure on my hole” while we did doggy before, but I’d never actually put anything in there before. Again, let me think on that one and I’ll get back to you…you might just get some shaving kit or something, you might get my butt…we’ll see.

That night Emily and I were hanging out and I was contemplating it while half heartedly playing video games, and I just blurted out “Em, have you done anal”…cue awkward silence, weird looks and then a “no, dosen’t that just hurt?” Yeah girl, that’s what I’d always heard, I’m asking if you knew from experience. Since neither of us knew, we hit the Google and skipping through all the porn, actually found some videos on how to safely/comfortably have anal sex. After watching a few of them, Emily hesitantly asked me if I had wanted her to help me try it, assuming correctly that Nick wanted to try buttstuff and I was nervous about it. No, I hadn’t considered asking you because that might be a little weird, but if you’re not opposed to it, then please?

Emily had way fewer reservations about sticking something in my butt than I did, but she eventually convinced me that the best way to just to anal sex with Nick would be to try some things with the comfort/no pressure situation of doing it with her. I was still super hesitant about it, but agreed to let her try a finger to see if it was something I’d consider.

In the most unsexy way ever, I rolled out of bed and took off my pajama pants and sleepy undies, leaving my oversized tshirt on and pulled the bottle of lube out I’d my nightstand and grabbed a spare towel from the bathroom. I nervously kneeled down on my bed with my butt presented to Emily as she stood behind me, lightly dragging her fingers across my wide-spread buttcheeks. I reached back between my legs with one hand and slowly rubbed my clit, doing just enough to help me relax a bit, waiting for Emily to take the lead in this new found territory.

I squeaked as I felt a cold drop of lube plop squarely on my puckered little butthole. I clenched down tight at the shock, but began to slowly relax as Emily rubbed the lube all around my hole with her index finger as I slowly began to open as she pressed in to the first knuckle. She asked me how I was doing and began to tease in and out, pressing lube up inside me, preparing me for what was to come. As I began to relax, the muscles of my tight anal sphincter gradually loosening to allow her full finger inside me, my breathing picked up and I was waiting for the point where this sudden feeling of fullness would switch to the hurt I was coming to expect. Her single finger inside me left a distinct full feeling that made me thing there was no way I could take a penis.

She reached her other hand between my legs, rubbing my clit as she added more lube to my butt as she slowly added a second finger deep inside my butt that caused me to squirm but added to the growing intensity of feeling full. As I relaxed enough to take her fingers, Em began to pump them in and out of my butt in a slow, steady rhythm as I relaxed to the point that she was freely moving in and out of me without a nervous clench. I was now open far enough that when Emily pulled her fingers out of me to add more lube, my hole stayed slightly gaped, open to receive something more. My arousal began to grow as I got used to the sensations pulsing through my stretched hole combined with Emily’s gentle play with my clit and I was softly beginning to moan with pleasure in addition to the slight sighs of discomfort from the new found stretch.

Emily pulled her fingers out of me, leaving me stretched but empty as she went to my dresser and retrieved to 7-inch blue dildo that I’d recently played with in front of Nick. No way. No fucking way is that going to fit. I almost cried at the thought of trying to stretch to take it but I stayed bent forward and Emily rubbed my back, telling me to relax as she rubbed lube up and down the length of the toy, giving it a pseudo hand job as I rubbed my clit with an urgency, trying to convince my body that it wanted this. She poured more lube directly onto my butthole, massaging it inside of me with 2 fingers as I took a sharp breath in when she pressed the head of the silicone cock against my second entrance.

She rubbed the small of my back before grasping my hip with one hand, pulling my hips back onto the cock in her other hand, my hole stretching to take the head as I moaned that i was so full. I deliberately focused on relaxing each ring of muscle in my butt as the cock pressed in and in and in, in what felt like a seemingly never ending dick that kept filling me more than I’d ever felt before. I felt the balls of the toy finally press against me, signaling that I was now truly full. It was a feeling of pressure that I’d never experienced and I had no idea whether or not I could enjoy this or if I would get stuck on “full”.

Emily slowly started to back the toy out, before returning it to its position with the balls against my outer lips. Again and again, slowly, she pressed it in and out, in and out, penetrating my hole as Em rubbed my clit, balancing the strange fullness with the pleasure of the beautiful woman touching my sensitive nub. She slowly picked up the pace and the pressure in my butt increased as I began to understand that for me, anal sex would be almost like mutual masturbation, with me getting myself off playing with my clit as my partner used my tight entry to fulfill their own pleasure and gain release. I felt genuinely erotic, almost like I was performing for Emily as I brought my hand to my it, rubbing myself towards my own release as Emily continued to pump the toy into me in what would have been a pace to gain my partner’s release.

I finally came with my own fingers, my vagina clenching down in sweet release as my butt clenched tight around the toy in a manner that would have certainly drawn cum from a partner deep inside me. I was sweaty and out of breath and utterly spent as Emily removed the 7 inches of blue silicone from my butt. My butt took a minute or 2 to finally clench back tight as a fairly large about of lube leaked out off my butt and onto the towel I now sat on as I talked to Emily about what just happened. We both agreed that anal was more like masturbation for both partners while using my butt for his release, but could see how erotic it could be if it was done slowly and gently, taking care to avoid the hurt that never came as Emily had truly taken care of me. I went to the shower to clean up and Emily had kindly pulled out a heating pad for me to sit on for awhile afterwards while we continued to chat before bed.

Overall I’d decided that I was willing to try anal with Nick, on the grounds that he treated me as gently as Emily. Emily meanwhile thanked me for letting me try this with her. It was apparently quite the turn on for her to get to use toys on me and I tucked away that tidbit of information away for future reference before kissing her good night and thanking her for not being weird about wanting to try something new.

I’m sorry for the lack of like Uber passionate fun today, this was another of those “learning moment stories” vs a pure sex thing and I promise there’s more to come involving this hole in the near future. I hope you all have a great night! As always, the comments and chat are always open!! ♡Jen

Source: reddit.com/r/eroticliterature/comments/r6x8ol/jens_university_chronicles_part_12first_time_in