First-Date Sex (The Best Sex I’ve Ever Had) [FM]

So, it looks like I’m back again. I took a long break from this site- and this account, especially- mainly because I ended up spending a little too much of my time on here. But I’m back again to share another experience that I just had over this past weekend. Since I don’t have anyone in my life right now that I can talk to about sex, I figured I’d come spill everything to the internet. Lol.

So, recently, I started getting back into the dating scene. I went through a rough break-up about a year ago, but for the most part I’ve been pretty happily single. A couple weeks ago, though, I decided that it was probably time for me to “get back out there,” and just see what happens. After almost a year of my love life being practically non-existent, I ended up with 3 dates this past weekend. I’ll only be talking about one of those, though, and it was with a guy that we’ll call “Brandon.”

Brandon and I found each other a couple weeks ago on a dating app, and hit it off pretty well. We officially met for the first time this past Sunday afternoon, when he came to pick me up for a date. We had exchanged a few pictures up until that point, but of course it’s never the same as seeing each other in person. He’s a little bit taller than me, with the perfect amount of beard scruff, and green eyes (which I’ve always had a thing for).

He drove me out to his place, which is just a couple towns over from where I live. It’s a nice drive, and we were bantering with each other the whole way there. We had talked beforehand about the possibility of smoking some weed together, so we had a little on the drive. (Yes, I know weed’s probably not the best thing to do on a first date- if for no other reason than it makes having coherent conversations a little more difficult.)

By the time we made it to his place, we were both feeling pretty good about each other; I learned more about him from that 30-minute drive than I did from a week of texting. He showed me around his house, which thankfully looked like it actually belonged to an adult- his place wasn’t spotless, or anything, but it was relatively clean; no trash or dirty clothes scattered across the floors; no huge pile of dirty dishes in the sink, etc. I can’t stress enough just how sexy this is to me. (My last relationship was with a guy who almost never even did his own laundry; instead, he’d take it to his parents’ house and have his mom do it for him. ? Seriously, don’t do that, guys- no one likes dating a man-child.)

Anyway, after showing me around the rest of his place, we ended up in his bedroom, where he showed me some of his (admittedly nerdy) collections; I’m a pretty big nerd myself, though, so if anything, that was just another turn-on. Not surprisingly, we ended up laying down on his bed, and of course, after chatting for a couple more minutes, we started making out.

Brandon kissed with a confidence that made it clear he knew exactly what he was doing- I found out pretty quickly that *every* sexual thing he does is like that. He doesn’t have to stop and ask for validation about his “technique,” because he **knows** that he’s good. That level of sexual expertise, combined with his sweet and nerdy demeanor outside of the bedroom, makes him one of the sexiest guys I’ve probably ever met.

As we kissed, his beard scratched against my skin, sending goosebumps everywhere when he lowered his mouth to my neck and chest. A shudder ran through me at the friction, and I grabbed a fistful of his shirt in response. He climbed on top of me, kissing me harder and pressing his hips into mine so that I could feel his cock growing hard under his jeans. I sighed and pressed back up into him, making him groan softly.

A few minutes later, we somehow ended up with most of our clothes off- I was still wearing my t-shirt and underwear, but he was down to his boxers. I hadn’t planned on going this far with him so soon; it’s not my usual style to do much more than kiss on a first date- maybe make out, but never to the point where clothes start coming off. For whatever reason, though, I just felt so comfortable around Brandon, and his confidence made everything feel so natural and right.

Gently taking my earlobe between his teeth, he gave it a little nip, and my breathing hitched. He continued moving his lips down my neck, and I squirmed under his weight, rocking my hips against him. There were just a couple of thin layers that were still separating us, and I could feel the fullness of his erection grinding against me.

Brandon pulled away slightly and looked straight into my eyes as he trailed his hand down my stomach and under my panties. We both let out a ragged breath as his fingers made contact with my pussy. “God, you’re wet,” he groaned, dipping his fingers between my lips and spreading the wetness up to my clit. I gasped, and my whole body went stiff for a moment; it’d been so long since anyone touched me like that, and it almost felt too good.

Confident as ever, he covered my mouth with his and began slowly rubbing circles against me, increasing the pressure of his fingers. Other guys have seen that reaction from me when they ventured between my legs, but they took my body stiffening to mean that they’d done something wrong (not that I blame them). Not Brandon, though- he seemed to know my body completely, and instinctively understood exactly how to make me feel good; I’ve honestly never experienced anything like it.

My legs began to shake as he continued working my clit, gradually increasing his speed and pressure until I was desperate for him to be inside me. I couldn’t speak, though, and didn’t have the presence of mind to do much more than grasp at his shoulders and keep my gasps and moans from turning into shouts.

“That’s right,” he encouraged. “Cum for me, baby.” His words, and the way that he growled them out, sent me over the edge, and I came for him right on cue. I covered my mouth with my hand and whimpered loudly as my body shook with the tremors of my climax. I opened my eyes to see that he was looking straight at me, studying my expressions as I came against his hand.

I collapsed back against the bed as my breathing gradually returned to normal, and the aftershocks of my orgasm eventually subsided. When I opened my eyes again, Brandon was still looking at me, and he gave a little smirk before leaning down and kissing me. He trailed his lips down my neck and chest, down my torso, and stopped just above my underwear, planting a soft kiss against my hip. I watched him, thinking, *There’s no way he actually means to go down on me after all that.* But the look in his eyes told me that’s *exactly* what he meant.

By this point, my mind had cleared a bit, and I realized what had just happened. *This is our first date,* I reminded myself. *If I let him go down on me, there’s no way that we just **won’t** have sex.* I’d never slept with someone- or even close to it- so soon after meeting them. I honestly think that if you’re wanting to potentially enter into a long-term relationship with somebody, sleeping with them immediately is probably not the best way to go. Ugh, but why was resisting that so much harder with him?

Brandon began pulling off my panties, and I stared at him almost in a daze. I’ve never had a guy go down on me, much less have them do so without me asking. *He’s seriously gonna do this,* I realized, feeling my body thrill with excitement at the thought. But as much as I wanted to feel his mouth on me, I reached down and stopped him. “No,” I whispered, shaking my head with a small smile. He raised his eyebrow questioningly, but I gave another small shake of my head. “Okay,” he said, stretching back out to lay beside me. “No problem.” He gave me a sweet smile, taking me in his arms and placing gentle kisses across my face. I felt myself start to relax.

After a few minutes, he asked if I was ready to go get something to eat. I hesitated; I didn’t like the fact that he had done so much for my pleasure, only for me to do nothing for him in return. At that moment, though, I was almost afraid of touching him in that way; I didn’t trust myself not to go further with him than I thought I should. So, I agreed that I was getting hungry, feeling a little guilty. I was sure I was coming across as selfish, but I resolved to make it up to him, somehow, later that night.

So, we got dressed and went to get some Chinese takeout. His roommate came home while we were gone, so when we got back we all hung out, watched a movie, and smoked a little more. By the time that was over, it was getting late, and Brandon asked me if I wanted him to take me home; he added that he’d love for me to stay over if I wanted, and spend the night cuddling and sleeping next to each other. I wasn’t naive enough to think that’s all that we would do, but seeing as how I basically have no self-control (ha), I agreed to stay over. Plus, I still wanted to return the favor to him from earlier.

Saying goodnight to his roommate, Brandon and I headed back to his room. We shared a few flirty glances and shy giggles as we started to undress for bed. He stripped down to his boxers, and I just had on my shirt and underwear again- I decided to go ahead and take my bra off, as well, since sleeping in it is never really an option to me. I crawled into bed after him, and he wrapped his arms around me and pulled me close.

Brandon spent several long minutes kissing my forehead and running his hand along my side; from my ribcage, all the way down to the back of my thigh, he dragged his palm, stopping to squeeze every once in a while at my waist, hip, or thigh. I could feel myself getting wet for him again, and almost involuntarily, I started rocking against him. He grabbed my leg and hooked it over his hip, bringing our pelvises closer. I rolled my hips so that my pussy brushed against his hardening cock, and he grabbed my ass and pressed me even closer. I sucked in a breath and he kissed me, teasing my tongue with his.

After a few more minutes of this, he rolled on top of me, sinking to rest between my thighs; the feeling of his weight settling over me made me moan in satisfaction. As he ground his cock between my legs, Brandon pulled down the low collar of my shirt and took my breast into his mouth. I shuddered as he flicked his tongue against my nipple, igniting my desire for more. Pulling his face back up to mine, I kissed him hard, wrapping my legs around his waist and using my feet against his ass to drive him harder into me.

He broke away with a gasp and sat up on his knees. Removing my underwear, he rolled me on to my side, and had me bring my knees toward my chest. I knew exactly what was about to happen: we were going to have sex on our first date, but I just didn’t care anymore. I wanted him inside me too badly to make him stop. Up until this point, I hadn’t really gotten a good look at his cock, but I knew from what I’d felt under his clothes that he was definitely above average.

Brandon lined himself up, and pushed inside of me with one sure stroke. My eyes widened, and I let out a rough moan. He was bigger than I’d thought- I’d find out later that he was at least 8.5-9 inches, well above the length of the guys I’ve been with in the past. I’d always imagined it might hurt a little to be with a bigger guy, but this didn’t hurt at all.

As Brandon drove his thick cock into me, it felt like he was hitting something deep inside that reverberated throughout the rest of my body- like a clanging bell whose echoes can almost be felt as they travel through the air. I don’t really know how to describe it, except that it felt amazing, and was unlike anything I’ve experienced before.

Brandon pulled away, and teased, “Let me get it from the back.” A bolt of electricity seemed to shoot through me at that, and I rolled onto my stomach, lifting my ass and spreading my legs for him. For several reasons, my last boyfriend couldn’t do doggy style- or most positions, actually (pretty much only missionary and cowgirl). So, my body was thrumming with anticipation for something more exciting.

Brandon smacked my ass before thrusting all the way inside me. I was expecting it to be a little harder for him from this angle- I’d usually tense up to the point where it was painful or even impossible for a guy to enter me from behind, but not with Brandon. I felt so comfortable with him, and it all seemed completely natural and effortless. I think his confidence made me more confident, as well.

He grabbed my hips and drove himself deeper, making my head spin. I worked my ass back against him in time with his thrusts, thoroughly enjoying the sound of our skin slapping together. My moans were coming regularly now, interrupted by choked gasps and exclamations like “yes,” “baby,” and “so good.”

Almost too soon, he pulled away again- abruptly, this time. He stood up from the bed and grabbed me behind my knees, pulling me to the edge of the mattress. Taking my ankles, Brandon rested them on his shoulders, leaned forward, and slid into me again. I cried out at the sensation and gripped his arms frantically, but he took my wrists and pinned them down by my head, interlacing his fingers with mine. I practically growled at him, the pleasure was so intense. He was being so rough and gentle at the same time; he was completely dominating me, but only to make me feel so damn good.

“Fuck,” I gasped, my eyes widening up at him as he looked directly into my eyes, pumping into me even harder and deeper. He let out a harsh breath, and groaned, “God, you’re so tight and wet.” He slammed into me, making my eyes roll back. “That perfect little pussy feels so fucking good.” That was the end, for me.

At his words, my body convulsed; I moaned loudly, said something I don’t even remember, and came hard around his cock. I just barely heard him say, “Oh, my God” under his breath, and I opened my eyes to find him- yet again- studying my face. The eye contact only intensified my orgasm, and I struggled to keep my eyes open and focused on him as my body quaked.

When I started to come down, I saw that he was sweating, and I knew he hadn’t cum yet. Before I could offer, he asked if I wanted to get on top and ride him; I was exhausted, but I wasn’t about to stop until he’d finished. I gladly nodded my assent, and went to straddle him as he laid himself down.

I didn’t waste any time before sliding down onto his shaft, taking the entirety of his cock inside me. This all felt like the longest sex session of my entire life, but in reality, it must have only taken around 10-15 minutes. Regardless, he had been doing all the work so far, and I wanted to show him that I was more than willing to do my share. Despite having just been thoroughly fucked, my energy rallied, and now it was his turn.

Brandon brought me down toward him, so that our bodies were flush against each other. I kissed him, gently rocking my hips to tease his throbbing cock. He speared his tongue inside my mouth, and I caught it between my lips, sucking lightly in time with the rhythm of my movements. He groaned and I pulled away, sitting up on top of him.

“You’re so sexy,” he murmured, squeezing my thighs. “And so soft.” He placed his hands in mine, and ran my fingers across his calluses. “I’m so used to feeling these, all rough and hard. But you,” he continued, using one hand to grab my ass and the other to snake under my shirt and cup my breast, “you’re soft and smooth all over.”
I stifled a whimper as I listened to him. It had been so long since anyone spoke to me like that, and I wasn’t sure if anyone had ever done it so sweetly. Unable to come up with a coherent response, I tightened my muscles around his cock, making him gasp softly in surprise.

Leaning back, I placed my hands on his legs for support, and rolled my hips. I heard him sigh, and his hands moved back to my thighs, speeding up my pace. “Oh,” I breathed, letting my head drop back to expose my throat. One of his hands moved from my thigh to press against my clit, and I cried out, moving faster.

After a minute or two, though, Brandon pulled me down to him again, pressing me against his chest. I changed the motion of my hips from rocking to bouncing, and we moaned in unison. Reaching a hand up, he grabbed my neck and gave it a light squeeze; I bit down hard on my bottom lip. Again, it was as if he knew exactly what I would like, and when I would like it most.

A whimper escaped my throat, and a fresh surge of energy filled me up. I bounced harder on his cock; by this time, he was thrusting up from underneath me, and our bodies were moving in perfect unison. It felt like we were designed to please each other, and that thought spurred me on to my next orgasm.

My pussy clenched around his cock, and my hips came down hard against him. Our bodies had been entangled in a kind of graceful dance, but as my climax shot through me, my movements became less fluid, though more insistent.

A couple moments after I peaked, Brandon did the same- he let out a curse through clenched teeth, and gave a long, low moan. I pressed my forehead against his, riding him to his orgasm; finally, with one last loud grunt, he spilled himself inside me, and fell back, breathing heavily.

I pressed one last kiss to his lips as I moved off of him; the feeling of his long cock sliding out of me caused a shudder to ripple through my entire body. We lay next to each other for a while, too exhausted to speak. When he’d somewhat recovered, Brandon turned his head towards me and said, “So… that was some pretty damn good sex. You kind of just rocked my world.” He gave me a smirk, and I laughed. I was honest, and told him that I couldn’t even think straight enough to return the compliment- but yes, it was very, *very* good.

So good, in fact, that we did it two more times that night, and another in the morning before he finally took me home. A few days have passed since we saw each other, and I’m starting to think that I got very lucky with this guy.

The stereotype (or, “rule”) tells women that if they sleep with a guy on the first date, he’ll lose all interest and respect for them. And maybe that’s even true most of the time, but it doesn’t seem to be the case with Brandon. If anything, he seems *more* interested in me now, and not even just sexually. I’m thinking that I just might have found an exception to the rule, here; I guess time will have to tell.

Source: reddit.com/r/gonewildstories/comments/97xkg8/firstdate_sex_the_best_sex_ive_ever_had_fm