This happened a few years ago, but still tops any hookup I’ve had for most frustrating buildup. I had just moved to a new area, and hadn’t had sex for several months prior to this. Hope you all enjoy!
It was a Friday night and I was waiting for my friend to tell me where she was. I knew she was with her boyfriend. She tended to move fast in relationships, and the PDA was plentiful, which made hanging with them awkward. But I had no other plans and was determined to go out.
Finally, she texted: “Ok so I’m with Sam… but he has a friend with him. You aren’t going to like him. He’s kind of rude and not very smart.”
I believed her. Melissa usually had a good grasp on my preferences. I thought for a few minutes, considering whether it might be better to just call it a night than meet someone new I might hate.
“So…. should I not come?” I asked. Maybe she’d make the decision for me.
“No no, definitely join. Just ignore him, don’t worry about it.”
That settled it.
I Ubered over to the bar where they were, and saw Sam and Melissa instantly… all over each other. Great. I took a deep breath and mustered up a smile at Sam, gesturing at the bartender to get me many drinks. Just… tons.
“So… where’s this friend I’ll hate?” I asked Melissa, hoping he had left.
“He stepped out for a smoke, but I think he’ll be back. Also: he’ll probably try to hit on you.”
“Of course.”
I downed my drink, wondering how long I had to stay out to be polite.
Right on cue, a guy I assumed had to be the friend clapped Sam on the back and grinned at me. He had piercing blue eyes, was about average height, a trimmed beard, and a baseball cap on. Melissa was right, he seemed like a townie…definitely not my type. But, objectively very cute.
I averted my eyes, pretending I wasn’t fazed.
He extended his hand out towards me and drawled, “Hey- you must be Melissa’s friend. I’m Dylan.”
He had a semi-Southern accent that was characteristic of those who had lived in the area forever. Yeah, not into that either… but his hands were soft and warm, and he gripped my hand in his in a way that sent electric shocks through my body. I smiled politely, then decided to pay attention to the next drink I had just ordered… determined to heed Melissa’s warning. He didn’t get the hint. He sidled up next to me and looked me up and down in a predatory way that was decidedly lecherous, but that I didn’t hate.
“Hey hey- what’s your name again?” He asked, shouting over the bar’s ambient music.
“It’s Carlotta,” I said.
He scoffed. “Car-WHAT?”
I rolled my eyes. Over the years people had made endless fun of my name. My parents were of Brazilian descent (some say I remind them of a curvier Camila Alves) and they had named me Carlotta after my Aunt. But the non-Americanness of the name sometimes threw people off.
“Car-lot-ta” I spelled, over it already.
He laughed and poked Sam in the ribs. “What a name!” he exclaimed loudly.
Ok, yeah, he was rude. Any attraction I initially felt faded, and I decided I’d give it 15 more minutes and then make a run for it.
Sam and Melissa suggested we go to another bar that wasn’t so loud. I agreed readily, downing my second drink quickly. Dylan grunted his approval, never taking his eyes off me. I pretended I didn’t see.
On the way to the bar, Dylan continued to harangue me, making fun of my name and calling me uptight for not laughing at his jokes. I knew what he was doing, and wasn’t impressed. After the 10th time he laughed at my name, I got frustrated. I turned to him and said, “I hope the two brain cells you rub together at night keep you real warm.”
He howled and stepped back, clearly surprised at my retort. But it worked- he backed off a bit until we got to our destination.
We sat at a table away from the bar, so we could all talk. Melissa and Sam immediately started making out, oblivious to Dylan and my’s presence. Dylan and I made disgusted faces at each other, which he took as encouragement.
“So,” he started, sliding closer to me on the bench we shared. “You’d never go for someone like me?”
I was taken aback at his forwardness, and stammered, “Well… I mean, since I met you all you’ve done is made fun of me. Also Melissa told me I wouldn’t like you… so I kind of trusted her.”
He looked visibly insulted. “Oh really? Why?”
I wasn’t sure what to say. “I think she just wants to look out for me, that’s all.”
His mood soured, and he turned his attention to his phone. I felt bad. Clearly I had hit a nerve.
“Look,” I said. “Let’s forget about that. It might piss her off to see us getting along. So let’s start over. I’m Carlotta.”
He glanced at me, and smiled again, nodding. We spent the next hour chatting, and I found myself enjoying our conversation. He was really sweet, even if he peppered his more serious conversation with innuendos. I noticed he had a really long, expressive tongue. I imagined it against my clit, tending to it carefully and languidly. The hands I had previously admired were also in play, and every so often he caressed my arm, sending more of those tell-tale electric shocks up my body.
We continued chatting, and the conversation turned to dating.
Eventually, he told me about a girl he had been talking to on Facebook for weeks, who he had invited out but had made excuses about not being able to. I felt a flash of jealousy that surprised me. But on second thought it made sense- he was super cute and clearly a lot more kind and thoughtful than I had thought at first. Also, the way we were talking and flirting made me think we would click physically. Sometimes I have a nose for these things.
But clearly he thought he didn’t have a chance. As the night wore on, he agonized about the Facebook girl. It was clear he was attracted to me, though. He turned to me once when I was speaking and said, “Damn, you’re really pretty.”
I stopped mid-sentence and blushed deeply, trying to hide the fact that he surprised and aroused me. We flirted heavily, but he kept checking his phone, which I found annoying. After awhile, I decided to be bold and told him to forget about Facebook girl and see what happened with us. He hemmed and hawed.
“See I would, but I’ve been talking to her for weeks… So I think I just have to see it through. Besides, Melissa seems to think you’d hate me or whatever.”
I shook my head vigorously, telling him to forget about what she said. But talking to her for weeks… I guess I understood. If this seemed like a sure thing and all, and I was a risk. I understood the logic, but I was disappointed. Worst of all, he left without asking for my number, so I thought for sure it was over.
The next day, I found myself thinking of him, and wondered what he was up to and what had happened with that girl. Most of all, I thought about how I could get in contact with him again. Even if he wasn’t my usual type, I couldn’t deny that when we were talking and flirting, I got more turned on that I was prepared for. It had been a good few months since I had had sex, and I hadn’t met anyone I was attracted to recently. I thought of texting Melissa to ask about him, but pride got the better of me. Instead, I downloaded Tinder, hoping someone could ease my frustration.
I swiped through for the next few days, chatting to a few people but not really finding myself too interested in anyone. Suddenly, I saw a profile I recognized. My heart started pounding. I couldn’t believe it. It was Dylan.
I did an internal happy dance and almost hyperventilated at what fate clearly had in store for me. I paused for a moment, composed myself, and swiped right. It was a match.
He messaged me instantly: “Lollll seriously?” A flash of annoyance disrupted my decidedly X-rated thoughts.
“Uhhh yeah,” I said. “I thought you knew something was happening that night… but you ran off to see FB girl.”
“Oh, I really didn’t think you liked me. I’m really surprised we matched. But hey, I’m not complaining… really.”
Ok, we were back on track. I breathed a sigh of relief and let myself get giddy on adrenaline and lust. I suggested that we talk via text and gave him my number. We decided to see each other the next night at a bar after he got off from work. I could barely see straight, I was so aroused. I started the necessary preparations for what I thought was a sure thing- shaving, cleaning my place, drinking a little, touching myself more than a little throughout. I felt triumphant already even though nothing had happened yet.
The next day came, and I had decided to steel my nerves by having a glass of wine before I met him. We hadn’t made specific plans, but I wasn’t too worried. He texted somewhat casually at around 4 that day, checking in. I waited the requisite 30 minutes (yeah, I know…) and texted back, asking what his plan was for the day. He said he was going to meet a friend at a bar near his place. Oh.
“So…. is that an invitation or are you just going to meet your friend and call it a night?” I asked, confused.
“Lol an invitation. You are funny,” He responded.
Another flash of annoyance. What was so hard about this?
“Well, I thought we were meeting up…?” I said, trying to keep my cool.
“Yeah, I know- I just have a buddy with me and am not sure what to do with him, he wants to hang,” he replied.
I gripped my wine glass, grunting in frustration. Ditch the friend, dude!
We went back and forth like that for awhile, me trying to tell him that if he had other plans then that was cool, but I wasn’t going to wait around for him all night. He was apologetic, and said that he really wanted to hang, but it was clear he wasn’t making any decisions anytime soon. I finally broke down and called Melissa to vent.
“Look,” she said. “He clearly isn’t making a decision and that’s lame. Just forget about him.”
She didn’t understand. I was so turned on and frustrated, I almost cried.
Finally, perhaps interpreting my long text silence correctly, Dylan texted: “Hey, can my friend and I meet you at a bar near you?”
I let out a sigh of relief and gave him the address of the bar around the corner from me. Friend be damned, it was going to happen.
He showed up about an hour later, friend in tow. Part of me was surprised he really brought his friend, but, as he told me later, he really didn’t think anything would happen.
Dylan and I flirted heavily, so much so that his friend took a newspaper out and started reading it pointedly. I didn’t care, and continued to make eyes at Dylan. Finally, his friend went to the bathroom, and I asked Dylan if he wanted to hang out at my place. He looked surprised, and stammered a “Sure- but [Friend] drove me here. Would you be ok driving me back?” Yes! Didn’t he see that I was throwing myself at him?
He finally told his friend he’d be hanging with me, and we departed for my place. We laughed and joked the entire time to my apartment, and I worried that we would never actually make physical contact. But finally, once the door to my apartment clicked closed, he pressed me against it and kissed me deeply. I melted, wetness pooling in between my legs. He noticed, and started kissing his way down my throat towards my stomach, bunching up the fabric of the short dress I had decided to wear so he could have better access to my exposed flesh.
I moaned and bucked towards him, trying to guide his mouth to where I needed it most. He stood up suddenly and kissed me again, fingers on my underwear-covered labia. He gasped when he felt how wet I was, and moved the fabric aside, fingers circling my clit. My knees buckled and I saw stars, almost falling over. My hands immediately went to the considerable bugle he was sporting in his jeans, stroking him slowly.
He grunted, and said, “Damn, you are hot.”
I smiled and unbuckled his pants, shoving his hand from my underwear and kneeling in front of him. I salivated at the thought of giving him head, and grinned at him.
“I love blowjobs,” I said. And I really do. Something about the intimacy and the control, I love it. I’ve also been told I’m pretty talented in that department… I guess enthusiasm has a lot to do with it. His eyes widened and he took his dick out of his pants wordlessly, guiding it to my lips. It was about 6″, circumcised, perfectly ivory with a tuft of reddish-brown hair at the end. I took the head into my mouth and watched as his eyes rolled back in his head and he let out a loud groan. I smiled to myself devilishly, then sucked from base to tip, letting my tongue bathe the underside. His mouth fell open as he watched me, immobilized. I moved faster and faster, bobbing my head up and down, making sure to keep even suction. I used my hand to stroke him in time with my mouth, and he almost combusted right there.
“Stop, wait,” he said, gesturing for me to stand. “Let’s move.”
He guided me to the bed, kissing me hungrily. I let him undress me, and his mouth attached to my nipple, sucking hard and making me arch into his mouth. I felt feverish. He finally touched me again and I grinded into his palm as he used two fingers to enter me. His fingers curled up and touched my g-spot, and I thanked all the gods I don’t believe in for this fantastic moment. He was every bit as skilled as I thought he might be.
He stroked while sucking on my breast, and I could feel that an orgasm wasn’t far. I told him to go faster, and he finger-fucked me with all his might. I contracted against him and told him I was cumming, and he grunted in approval. I finally came- and I did hard, panting as I caught my breath.
I lay there for a second, enjoying the waves of pleasure. He grinned up at me, looking pleased with himself. He licked his fingers languidly, and I remembered how I admired his tongue that one night.
Somewhat shyly, I said, “Would you use your tongue on me too?”
He grinned wider, and pounced, spreading my legs with his hands and positioning himself in between. He blew warm air across my clit, and I jumped in surprise. He tried to tease me for a few minutes, kissing around my clit but never on it, until I whimpered and begged him to just “Do it already.”
He complied, flattening his tongue against my clit and lapping quickly. I almost screamed in delight, legs twitching against his face. He put two fingers inside me again and pumped slowly, sucking on my clit all the while. I bucked against him, and had orgasm #2 shortly after. Finally, I had enough torture and told him I wanted him inside me. I grabbed a condom, and he put it on as quickly as he could. He positioned himself above me, and I felt the head of his cock right at my entrance. Not wanting to wait, I slid down until I could feel him almost completely fill me. I winced a bit, forgetting I hadn’t done this in awhile. But soon, the discomfort gave way to pleasure as he gently rubbed my clit and started pumping in and out.
It was better than I had imagined. He pumped quickly, but not at jackhammer speed, rubbing my clit the entire time and whispering dirty things in my ear. He told me I felt so good and tight and warm and wet, and I could only babble and moan in agreement. He picked up the pace as I clawed his back, trying to get him further inside. The next orgasm hit me by surprise as he angled himself to hit my g-spot, and my walls fluttered against him. He told me he wasn’t going to last very long, and I told him that was totally fine- but I wanted to taste him. I told him to keep going until he was almost there.
It didn’t take him long, he pumped faster and faster until he exclaimed that he was close, and pulled out of me and took off the condom. I barely had a few seconds to spare before he came, and I was treated to a bit of semen on the side of my mouth before catching it in my throat and swallowing it all. It was salty and warm, and I was satisfied.
Feeling suddenly shy, I ducked into the sheets as I wiped my mouth. He looked at me, stunned, breathing heavily.
“Damn,” he said. “I am so glad you don’t hate me.”
I giggled and stroked his beard, kissing his cheek.
“I definitely don’t,” I said. “So… when can we do this again?”
Dylan and I ended up hooking up on and off over the next year. It fizzled once we decided we wouldn’t date, and he moved 30 minutes away. But I had some of my best times with him, and definitely miss the sex!
Source: reddit.com/r/gonewildstories/comments/7vbain/so_much_frustration_with_a_merciful_payoff_fm