This is the second part of my story posted here, and the last part of what happened that night. Just as a recap, I’m Mike, about 5’11” and 130lbs on a good day. Dark brown hair that’s usually in a fauxhawk-esque poof, hazel eyes, and big lips. I know it’s cliché for this subreddit, but I’m a little under 6.5”, and I curve up some. Thea was a girl I met online (OKCupid, if you care). She was 5’ 8”, with C or D cup boobs. Dark, frizzy hair, gorgeous face, and wore glasses.
Thea and I loaded our blankets up into the back of my car. We were still slightly on our high from banging each other, and we didn’t want the night to end so early. I looked around on my phone at the map, looking for a place that would be out of the way, but I wasn’t familiar with that part of town, so I asked her to navigate. As we drove, we talked about things that turned us on. She was very into bondage and discipline, whereas I had been in a very tame relationship previously. I told her I’d try anything once, and she quickly agreed that so would she. We were quiet for a moment, and then she asked if we could try anal. I had lube, so I told her as soon as we found a place to park I would be happy to oblige.
We drove for maybe 15-20m, and eventually found a secluded neighborhood without a lot of streetlights or traffic. I parked on the side of the road, and we climbed over the console onto our makeshift floor in the back seat of the SUV. We made out for a few minutes, me finger-fucking her and her stroking my penis. She pulled away and grinned at me, then got onto all fours, sticking her ass in the air. “I want you to try and fuck my ass” is all she said to me, so I pulled out the lube and put a generous helping on my fingers. I’d never tried this before, but from the amount of…erm…research I’d done, I knew to use lots and lots of lube for her first time.
I spread the lube all around her smoothly shaved asshole, then slid one lubed finger into her puckered hole. She shifted a little, but didn’t say anything. I worked that finger in and out a few times, and then added a second. She looked back at me, breathing a little quicker, “Put three fingers in me please!” I wasn’t about to argue, and I stuck my third finger into her and pumped her slowly with my fingers. She seemed to be enjoying it, so I lubed up my dick with my free hand and used my fingers as a guide. I pulled my hand away, instead focusing on her clit now, and pressed my head against her asshole. Nothing seemed to be happening, so I pressed a little harder. Very slowly, I added more pressure, fingering her all the while.
Two things happened at once; my head popped into her asshole and sheathed itself maybe ¼ of its full length, and she screamed out and pulled away faster than I thought she could. My dick got pulled along with her body for a moment before I pulled it out, and her ass was so tight I wanted to go right back in. She was panting, reaching back with one hand keeping my dick away from her. “No no, stop, just wait a minute, oww…” I sat back on my heels and waited for her to recover some, trying to maintain my boner. She looked back sheepishly at me. “Maybe we should try it again another day, yeah..? That really fucking hurt.” I nodded and grinned, apologizing. I knew she craved pain as a fetish, but I didn’t want to go past her limits.
She felt around, then handed me my belt. “I want you to spank me. HARD.” Take another thing off the list of things I haven’t tried. I smacked her asscheek with the leather end folded over, but she stopped me and flipped it over to the metal buckle. “I want you to spank me hard, Miikee!” SMACKjingle I hit the side of her ass, and she moaned like nothing I’ve heard. I’m not particularly into the SM side of BDSM, but hearing her moan like that turned me on so much. SMACKjingle I hit her again and again, alternating sides every now and then to keep her guessing. SMACKjingle Every time I hit her, she rocked back and forth, keeping a nearly constant moan. After a little while of making her cheeks bright red, I put the belt down and positioned myself behind her. I was so hard right now, and my dick was actually bouncing up and down a little from how hard it was throbbing (guys, you know how I mean).
I grabbed a handful of hair, my other hand guiding my dick into her pussy, and I started railing her again. My legs slapped into her already tender ass, and she was holding onto anything available to give me something to push against her pussy. I was stupid enough to not have put a condom on, so right before I came I pulled out and came all over her back. She collapsed on the ground, orgasming hard and panting. I laid back, panting just as hard and basking in my afterglow. It was late by now, and I drove her back to her place. We kissed goodbye, and I drove home hoping to god my flatmates weren’t awake so I could make a quick exit to the shower.
We’re meeting again tomorrow night, and we’ve talked a lot about what we’re going to do. Like I said, she’s very into bondage, and she can take being a dom or a sub. I have access to a leather belt, a few cloth belts with metal ring clasps, rope, lube, and an assortment of blankets. We’re gonna be mostly in “public” (on a secluded beach at night), but reddit, what is your favorite domination/pain sex act to do? We’re trying anal again, but I want to get her worked up before I stick my dick in her. Leave me a PM or a comment, and be looking for an update within the next week!
Source: reddit.com/r/gonewildstories/comments/32f5ux/my20m_first_time_with_a_thick_girl20f_part_ii