Regret, sort of Pt 1

I sometimes think back to the woman who broke me, the one who lead me to do some of the worst things I’ve ever done. The one who was so much fun. I had had a bad sex life until I was about 25, full of awkwardness, bad communication, assumptions, taking verbal abuse, you name it. I was starting to use social media to meet women and had no idea what I was about to get myself into.

I was chatting with two or three women at once and anxious to meet up. One in particular we had great chemistry before even meeting. We had phone sex one night about a week before meeting, which she told me she rarely had. Even more rare is that she came. Knowing that her body orgasmed with my verbal help made me feel so good. But we hadn’t even met yet, so I was open to dates with other women.

I thought I was going to have a hot and heavy date with this other woman who agreed to just flat out come for dinner at my house. Oh boy, I was nervous. I had high hopes that we would end up in bed with her giving me filthy orders in Spanish (that language does things to me).

Naturally we ended up eating awkwardly, and I’m not talking about oral. Her online flirtiness was replaced with a slightly standoffish attitude during our little episode in my apartment, and it wasn’t playful banter or anything charming. The realization that our attraction totally fizzled out once we were in each other’s presence was like a mist over whatever the hell I made that night. I ended up eating something far better later. Spoilers.

When we finished eating she invited me to go to some club or whatever. I had no interest. Like, less than no interest, not even in seeing her again. I just wanted to be left alone. I had every plan to beat my dick like it owed me a buck 30 and go to bed early. Before I got that far, I went online and noticed my phone sex partner. Let’s call her L. I told L what had happened and she didn’t seem impressed. Not because I had gone out with someone else but because she thought we’d have had a much better time. Something came over me. Even though it was almost midnight, I figured what the hell and I invited her to my place.

To my nervous surprise, she accepted. Went to pick her up and genuinely thought she was going to just hang around my place. I mean, my expectations were low already, I figured it would be par for the course. Well…

Seeing her in person was something. I had thought my type all these years was short and curvy. She was tall, thin, had a pretty face and a smile that did evil things to me. Her teeth weren’t perfect, her canines were a bit long and jutted out. For some reason, it made her smile so sexy to me. Maybe it was because it was unique. I made her laugh a lot and that smile of hers just gave me the most evil urges. Urges she was happy to indulge, it turns out.

We were on my couch watching some dumb comedy and at one point she just sort of readjusted herself, sprawling out so that her head was in my lap. I’m not the suavest guy in the world, but I somehow managed to contain myself despite the back of her head resting atop my still-soft penis. At one point, I just started running my fingers through her hair, still ignoring my urges. I have no game in general so I flat out say what’s on my mind. I tell her I would love to kiss her. She looked up at me and, while scanning my face and making a vague gesture to her mouth. I brought my face down to hers.

Our lips touched, and everything became a blur. I opened my mouth slightly and started licking at her lips, and she readily opened her mouth and let my tongue explore. Our tongues locked and swirled, gently at first but then more insistent. Her eyes were soft and chocolate brown, and I loved seeing them up close. I danced my fingers across her chin and cheek as I greedily tried to suck as much of her saliva off her tongue as humanly possible. She reached up and put her arms around my neck while I started to do the same to her. I enjoyed the feeling of our rough clothes rustling together, her black hoodie against my shirt.

My cock must have been digging into the back of her head at this point and she readjusted herself on the couch so we were sitting side by side. We kept making out hard, her arms around my head while I fumbled for the zipper of her hoodie. Revealing her tshirt underneath. At one point I touched her skin between her shirt and pants and that sent my erection into orbit. Hearing her soft little moans and the wet sound of our mouths, it was almost too much for me to take. But we couldn’t stop. I wanted more, so I started kissing down her chin and up her neck, sometimes licking, sometimes sucking. Maybe a quick nibble here or there. I tried to get my mouth under the neckhole of her tshirt while I rubbed her back. She gasped every time my lips made contact with her neck, and I felt her shudder harder and harder as I licked a trail of quick tongue strokes up from the base of her neck to her earlobe. When my lips got to her ear, I didn’t say anything. I just breathed gently, my cock throbbing with every sweet sound that escaped from her lips.

I don’t know how we got there but we were in my bedroom pretty quick. I undressed her, I always love undressing my partner and kissing the parts of her body I just exposed. At that point, I wanted nothing more than to eat her pussy and finger her. My ex was not into oral either as a giver or receiver, and I was aching. I wanted to worship L’s pussy, and she wanted me to. Her hoodie off, I got temporarily sidelined by her breasts. They were 34 B, an absolutely delicious mouthful. But the color. She had fairly pale skin, definitely caucasian. But she had dark brown nipples. I don’t know why but that drove (and still drives) me crazy. I kissed her breasts and sucked them into my mouth, making sure to suck and nibble the top, the sides, and the bottom before going after her nipple, flicking it in circles that got closer and closer to their tips, one after the other.

I couldn’t hold back anymore. I needed to worship. I took her panties off and was delighted by what I saw. Her labia were thin, her clit a dark pink. She lied down on the bed with her head away from the wall. As much as I wanted to stampede to her pussy, I also wanted to kiss her again. I climbed on top of her and slid my tongue into her mouth again, but after a hot ten seconds started kissing my way down her front. I could still taste my saliva on her breasts as I kissed my way down to her belly. I gave her belly some soft, gentle kisses. I began to notice a smell. It was… divine. It made me light headed. It made me an addict and I hadn’t even tasted her yet.

I kissed further, along the flare of her hips. Her inner thighs. I found the source of that divine smell. I gave her labia a full, deep kiss, gently at first, her lips and mine perpendicular with my nose grazing her clit. I had had so little experience with oral but I just… knew to keep it simple and follow my intuition. I knew at least I needed something. I needed to plunge my tongue inside her and get as much of her delicious taste as my tongue could handle. So I did. I opened my mouth as far as I could, careful to not press my teeth against anything sensitive, and I pressed it along her inner walls. I swept my tongue along her inner entrance while placing my fingers on either side of her labia. I gently pressed my fingers along her labia to pull them wider apart. I started licking her up and down, long licks. Slow licks. Up and down, down and up, teasing her clit. Circling her clit, grazing it again, then down back into her sacred, overflowing depths. I started sliding my tongue around her clit while sliding one finger of my right hand into her. I added a second, then a third. L was grinding her hips as if she was trying to swallow my hand whole, and before I knew it she was cumming on my fingers and tongue. She moaned and breathed hard, which was unlike any orgasm I had witnessed before, and she twitched. I took it all in and felt so good that I had helped her get there.

I had never had a lover who liked to taste herself, so when L licked herself off my face when she regained her composure, I’m not sure I could have been more turned on. I was wrong. She started undressing me and revealed my penis. She stared for a second and I was confused. I was also feeling very self-conscious because I used to feel weird and guilty over getting oral. She helped me get over it. I didn’t even have to ask her where I had been used to begging for lacklustre head. She wrapped her fingers around my cock, she stroked. She took the head into her mouth and licked around before taking it into her throat as deep as she could. She started bobbing up and down. At one point she told me something like I couldn’t hurt her, meaning that I could be rough. I was used to vanilla, I was used to dull selfishness, so to have her basically say that she was ok with me fucking her face was hot and slightly scandalous. She sucked my head and shaft so hard, and I put my hand on the back of her head. I felt bad at first but she never slowed down for a second.

I was enjoying it, but I was about to do something I never felt I was allowed to do before: enjoy myself. I warned her after a few minutes that I was going to cum. My previous lovers had treated cum like it was toxic waste, so I felt a weird mixture of fear and horniness at that moment, unsure of what to do next. So she showed me. She didn’t change her pace. Not to brag or anything but I haven’t got a tiny nub between my legs. Yet she managed to get more than 3/4ths of it into her mouth. I couldn’t believe what was happening. And then, my cock exploded onto the roof of her mouth, my hand gently but firmly on the back of her head. I had not felt an orgasm like that in my life ever. I felt so good from the orgasm itself, but the kinkiness, the validation of my desire, it made me swoon.

I know we cuddled right after that but oh my god did we fuck. We had sex five times overnight, the last orgasm making my dick and balls feel like I’d been punched in the gut. She was multiorgasmic, which is just the hottest thing ever. She lost count of how many times she came. By the time 8 AM rolled around, we had taken a break and were sitting naked in my kitchen. I was on the floor and even though every single muscle in my body was sore, I was still running my fingers along her inner thighs and asking her on my knees if she wanted to go another round. She said she just couldn’t. I was secretly relieved. There would be other times, and other far more naughty activities.

Source: reddit.com/r/sexystories/comments/ehtua8/regret_sort_of_pt_1