[MF] The First Woman to Ever Deepthroat Me

I realize that most of my stories make me sound like a all I have any interest in is fucking as many women as possible, and while it is true that I have a sky high libido and would like nothing more than to fuck all the time, *forever*, the truth is that on a daily basis I want what most people want, which is compansionship and a person to talk to.

That said, I have actually had a few long-term relationships in my life, and they have all been amazing. The first ended depressingly, with me being cheated on. The third resulted in some of the happiest days of my life. This is the story of my second long-term relationship, which began bizarrely and somehow just kept going.

I met a young woman at a club. She made fun of my shirt so I bought her a drink. It was an awful shirt, to be fair. I hate clubs and have no concept of how to dress for them. I wouldn’t have even been there if it hadn’t been for my friend Clubby, who would live her life in an endless dance hall if such a thing were possible. She liked to drag me along when she was trying a new place so that she could run to me and pretend I was her boyfriend if the vibe was all wrong amongst the club patrons. In exchange she usually bought me a few drinks but truthfully I would have done it for free because about half the time she managed to introduce me to somebody fun.

This particular evening was one of those nights. She brought the woman over and introduced me as her friend. After telling me how shitty my shirt was and me agreeing with her, we had some drinks and got to know each other as best as you can in a loud club environment, which is to say, hardly at all and we mostly danced. My new partner spent most of our dance time grinding her sizable ass into my crotch, so I was having a pretty decent time.

This young woman, who I will call Basic Betty (and before folks get upset, she professed to me about six or seven years later that during her college years she was “supremely basic in every single way” so it’s not like she didn’t realize), chose a slower song to grab my hands and wrap them around her, ass pressed firmly into my crotch, and turn her head slightly to whisper-shout into my ear, “Clubby says you have a big dick.”

I blinked. It was hard for me to to tell when Clubby was being a good wingman or messing with me so I just replied, “Well, I guess Clubby would know.” Which was true. Clubby and I had fucked once or twice, but we never really clicked. Our rhythms were off, I suppose. I got along well with her but we weren’t really compatible in the bedroom.

“Are you guys together?” Betty asked.

“No,” I replied, keeping it simple.

“Do you have a car?” she asked.

“I do, but I drove Clubby here. I’m her ride.” This was entirely true and I was grateful for it. I can definitely let my dick do the thinking for me in a lot of scenarios but taking a random stranger home from the club is really not one where I’d prefer The Commish take the lead on my thought process. Still, Betty was very attractive – not my usual, she was blonde and a little bit petite, but she was fun – and it was easy to see myself having an occasional good time with her.

I sensed the disappointment rolling off her when she realized I wasn’t taking her home so I followed up with, “I’d like to see you again, if that’s okay. If you’ll take it, I want to leave my number with you. No expectations, if I hear from you, great. And I’m not leaving until my friend finishes doing whatever it is she’s doing, so we can talk some more if you want.”

Betty made a “hmmm” face and then took my hand and led me to the second floor. I didn’t realize it when I entered, but the club’s second floor was a lot quieter and had more of a “chill out” vibe with many sofas and loungers. The loud music from below wasn’t quite as overpowering. Betty informed me that her friend was up there and I could hang out with them if I wanted. “Sure,” I said.

I found out quickly that the friend did not want to be at the club at all, which is something I can relate to. She spent quite a lot of time complaining about the entire club atmosphere. Not the *entire* time, but enough that she was sounding a bit like a broken record. I pointed out to her that if you don’t want to have a good time, there’s absolutely nothing that can make you happy, but if you embrace a litle optimism, the odds of you finding something fun in your outing are vastly improved. Those were definitely not the exact words I used. I think I said something more along the lines of, “If you set out to have a shitty time then it won’t even matter if the club owner craps a gold brick on your table and offers to pay all your student loans on top of that.”

I’m not always the most eloquent.

Regardless, Betty’s friend, who I will call Bittersweet, did manage to loosen up a bit, though she still seemed resolutely not a fan of mine. That’s fine. I don’t need her to be my buddy and in fact I can’t blame her in the slightest for not wanting to support a guy like me being in her friends’ life. I knew within ten minutes of talking to Betty that I wasn’t going to be in a relationship with her. I knew within fifteen minutes that I would probably fuck her.

Women who are reading this – your friends are going to hook up with guys like me on occasion. Sometimes they need that. Most of the time you should not be trustful of it. I’ll probably get shot by other men for saying this, but cock block away. Because for every guy like me who doesn’t take himself very seriously, there’s a few more who I will readily admit are assholes. The fact is, if your friend wants to fuck a guy like me, there’s not a lot you can do to stop her short of tying her up. But I’m not going to blame you for taking all those measures.

Case in point, I actually liked Bittersweet. She was actively trying to keep me from having sex, but she was a sass master, very opinionated, and loud. Those traits tend to make me want to be friends. I *like* women who know what they’re about.

Betty, on the other hand, was clearly becoming more aggravated as we all hung out together. Bittersweet was keeping her from doing what she wanted to do, and she was very clearly jealous of my attempts to get to know her friend. I’m very much postulating here, but I suspect I’m not the first dude she’s tried to pick up at a club, and I suspect that most of the guys she picks up are rude to her cock blocking friends, or simply ignore them. The moment Bittersweet left to visit the ladies room (after becoming exasperated with her friend, who refused to go with her), Betty climbed on top of me and stuck her tongue down my throat.

Such a subtle game she plays.

Not that I was complaining. Her instant bump and grind in my lap had me rock hard in seconds and when she finally came off my face for air she simply said, “If you get me out of here right now I’ll suck your cock.”

That’s a pretty lucrative offer, and there was a very significant part of me that weighed the idea of tracking down Clubby and forking over all the cash in my wallet so she could get a taxi or something to take her home, but ultimately friendship won out. “I can’t,” I said succinctly. “I’m the only ride my friend has and we’re pretty far from where we live.”

Betty made one last attempt, continuing to grind on me while leaning forward to whisper in my ear, “I’m really…*really* good at sucking cock.”

I internally punched myself in the face as I said, “I believe you, and I really want to test out your skills, but I seriously can’t leave my friend. We live like an hour away from here.”

She stopped and looked at me. I can’t quite describe the look on her face. It was like a mix of shock, lust, and anger. Again, I’m going to postulate here, but I’m pretty sure at the time I met Betty she wasn’t used to being turned down. To be fair, I didn’t *want* to turn her down. I wasn’t playing some game with her – she offered up a blowjob completely on her own which is, as I’m sure most dudes will agree, *the best* and my favorite, like every birthday party rolled into one with a kazoo parade.

“Okay,” she said, and I could feel that hard resentment in her voice. “Fine.”

She then sulked the rest of the evening until I left, but I noticed she didn’t say no when I gave her my number and told her what nights I was free the following week.

Clubby gave me shit the entire ride home when she found out I’d turned down a blowjob. I assumed she’d find the act adorable and chivalrous. I probably should have known better. I recall her exact words were, “Shit, I would have dropped your ass like a bad habit for some head. You’re an idiot.”

I agreed with her and told her she was free to give me head whenever she liked, which she astonishingly appeared to consider for a brief second before saying, “No, I don’t feel like busting out my tweezers for your micro penis.”

“Yeah, well when you find it, you’re going to have your world rocked.”

“Uh-huh.”

“Best three minutes of your life, girl.”

She laughed and we had a fun car ride home from there, and she gave me a kiss on the cheek when I dropped her off and admitted it was sweet that I didn’t abandon her, so Clubby is a big, big tough guy liar. Jot that down.

It was a solid week before I heard from Betty again, but it was worth the wait, because the text message string literally went like this –

Betty: Hey, it’s Betty. What you doin?
Me: Studying at my apartment.
Betty: *picture of her vagina*

Needless to say, I scheduled a date with her the following evening. The date part was uneventful, boilerplate stuff. We didn’t have a great deal in common. The accompanying sex part was pretty nice, to say the least. Betty’s proclamations of her blowjob prowess turned out to be a little exaggerated (*teeth*, holy fuck, too much), but what she didn’t tell me about is her amazing muscle control. There was one point that she was riding me slowly and she just settled down on top of me, taking as much of me inside her as she could, and then started tightening around me in an almost wave-like motion. It felt like she was fucking me without moving at all. I saw the straining concentration on her face and distinctly remember wondering just how many kegels she does a day. I loved it so much that I flipped her over and immediately began fucking her with nice long strokes while she gently massaged her clit.

She came on my cock multiple times, so just for the record, that kegel muscle control really pays off. Her cum spasms were so powerful she nearly pushed me out of her vagina every single time. I was literally battling with her vagina just to stay inside, like the weirdest fucking joust tournament you can imagine. I think if she wanted to, she could have snapped my dick off like a twig. Translate those vaginal muscles to the rest of her body and I was fucking the She-Hulk. It was a delight. I also suspected it was a one-off, because when we were finally done, she seemed to immediately lose interest in me. She cleaned up and began tidying up her apartment, and any time she looked over at me I could sense the surprise in her eyes, silently asking, “You’re still here?”

This doesn’t offend me. I have definitely had sex with women who want me out of their lives after they cum. Maybe I would get a call from Betty in a few months, or maybe I’d never hear from her again. There is something to be said about being *used* by a beautiful woman. I’m not saying I get off on it, but I’m not *not* saying that, either.

If it seems like I skimmed quite a lot on that particular sexcapade, you’re totally right. Betty isn’t the focus on this one. BOOM. Twisted again.

Less than a week after I hook up with Betty, my phone triggers again with a number I don’t recognize. It turns out to be Bittersweet. She claims she wants to see my college because she’s considering going back to school. I recognize this is bullshit but play along with it and schedule a time to give her a tour.

The tour turns into drinks at my apartment, which turns into ordering a pizza, which then turns into talking on my couch while the TV droned at a very low volume in the background. She was a great conversationalist, crazy smart. I could actively see in her eyes that she was analyzing me and figuring me out as we talked, which was good at sending a pleasant shiver up my spine. The conversation was pleasant and casual at first, but over time dipped into interesting territory.

Bittersweet: You guys have a shitty Asian population here, I’m not going to make any friends if I enroll.
Me: No way, the anime club will love you. Inappropriately.
Bittersweet: Oh, god, no.
Me: *in my best Hank Hill impersonation* So, are ya Chah-neez er Japa-neez?
Bittersweet: *laughing* Fuck you, man. I’m not going to be some white guy’s special Asian girlfriend.
Me: How about just some guy’s girlfriend, period?
Bittersweet: (coy) Maybe. Who’s asking?
Me: (feeling a bit uncomfortable) Hey, uh…I don’t know if you talked to your friend Betty, but-
Bittersweet: Oh, I know you guys fucked.
Me: Oh. Okay. And thaaaatt’ssssss…coooool?
Bittersweet: Yeah, Betty is a bitch. Like, she’s my friend, but she’s still a bitch. I don’t have a problem fucking guys that she’s fucked.
Me: Huh.
Bittersweet: Is it a problem for you? She’s not going to call you again.
Me: I see.
Bittersweet: Are you disappointed?
Me: Oh, no. Not really, I didn’t think she would. I’m just kind of trying to wrap my head around what’s happening here.
Bittersweet: I like you. I’m kind of mad that Betty fucked you first, but whatever.
Me: I’m sorry, I need to clarify, or just…are we going to have sex?
Bittersweet: Yes.
Me: Tonight?
Bittersweet: Dude do you think I drove all the way down here to look at empty classrooms with you? I thought you were in college.
Me: Look, I’m going to be real with you right now – I have no idea what to do. I have seriously never been in this situation in my life.
Bittersweet: Okay, look. You’re being weird. This is not complicated. Betty told me about you guys hooking up, I called her a bitch for fucking you after I told her I wanted to hook up with you, she went on with her life and now I’m here. She was jealous that you liked me more at the club so she had to like…get in, put her mark on you, whatever. Like I said, she’s a bitch.
Me: Well, to be fair, she did see me first.
Bittersweet: (punches me in the arm)
Me: Wait, is that why she offered to blow me when you went to the bathroom?
Bittersweet: Oh my god, that whore. I had *just* told her I liked you when I went to the bathroom. I was trying to get her to go with me so I could talk to her about it.
Me: You might be the most well-adjusted woman who has ever agreed to have sex with me.

If I seem uncharacteristically incredulous in that conversation, it’s because I was. I came to found out that Bittersweet was furious when she found out that Betty had fucked me, and then *made Betty give her all the details of said fucking.* I now realize that is very standard behavior for those two, but at the time, I found it weird as shit, and like most things that seem weird as shit, I didn’t trust it.

Bittersweet definitely came across as a weirdo, but she was also sweet, and I was undeniably attracted to her in something greater than my usual lust. This is probably why, as soon as we started kissing on my couch, I whispered in her ear that I wanted to taste her, causing her to immediately start kicking off her jeans under my body in violent, spastic motions, which in turn caused me to say, “Wow, ok.”

She was excitable, to say the least. After watching her comically writhe around trying to get her too-tight jeans off, I finally attempted to assist her and got kicked in the face.

“Oh, shit!” she exclaimed as I in turn clutched my face and went, “It’s cool, wait, no, I’m bleeding, sorry.”

It wasn’t that bad, but my nose was bleeding, though it didn’t look any worse for wear. Bittersweet got up and tried to run to my paper towels, trailing her jeans behind her on one foot because they were still stuck. She tripped a couple times and finally just threw the roll of paper towels at me.

I sat on the couch with my head tilted back and she sat next to me on her knees to examine the damage while apologizing profusely. We sat in silence for a moment before she finally asked, “Are you still going to eat me out?”

I turned to look at her sitting there in her t-shirt, and my eyes wandered down to her tight black panties.

“Yes.”

“Okay. That’s great. Just whenever you’re ready.” I remember her nervously fidgeting next to me, drumming her fingers on her thighs and making a sort of beatbox sound with her mouth that I’d come to know very well. Bittersweet had A.D.D. but I didn’t know that at the time. In hindsight, that knowledge brought most of her actions into a pretty clear light. She wasn’t good with the waiting as she finally asked if I wanted a handjob in the meantime.

I raised an eyebrow at her and acquiesced, because at that point I could already see the makings of a decent story to tell later on. “Dear Penthouse, there I was, getting a handie from an eccentric hot chick that made me bleed just moments before…”

To her credit, Bittersweet was crazy good at handjobs, just one of her skills, as I would soon come to find out. She helped me get my own jeans off and smiled appreciatively at the bulge in my boxer briefs. Looking up at me as she rested her hand on my cock, she simply said, “Big.”

I couldn’t tell if it was a statement, a question, or some Tourette’s-esque compulsive exclamation.

“Thanks,” I responded, feeling awkward.

Prying my underwear off, she licked her hand from base to fingertips several times before wrapping it tightly around me and jerking me off with an expert motion I mostly saw in pornography, her wrist twisting slightly at the head on each upstroke. It felt amazing, and became more amazing when she made herself more comfortable, laying on her stomach with her knees bent and her feet in the air so she could fit on my couch, staring intently at my cock as she stroked it at a regular, brisk pace. The view of her in a t-shirt and panties, lazily hanging out while jacking me off got me more than a little excited. I’m a little embarrassed to say that she probably only jerked me off for three or four minutes before I realized if she kept doing it I was going to cum.

I grabbed her hand to stop her and she looked confused. Not wanting to admit how close I came in such a short amount of time, I simply said, “I’m ready now.”

I wasn’t totally ready. It still felt like my nose might bleed a little and it had that stuffy, gross feeling that always accompanies a bloody nose. The stressful idea that my nose might start bleeding again while eating her out kept me focused and I was absolutely certain I wasn’t going to cum.

So this is the point of the story where you realize why I named my partner Bittersweet. It’s exactly how her pussy tasted. I mean, sure, it’s slightly thematically appropriate to her behavior and the memories of my relationship with her, but mostly it’s her pussy, because I am not a deep or difficult to understand person.

My name is Von Scriptenstein, and I like pussy. Don’t make me apologize for being myself.

I’ve gone down on my fair share of very nice ladies over the years, and Bittersweet tasted the best, by far, simply by virtue of that really strange sweetness that always lingered under the usual flavors. It was an aftertaste, but an extremely pleasant one. To this day I have no clue what magical item in her diet produces that taste, but I hope she never cuts it out, because it gave me the superhuman ability to stay down there for at least an hour.

If that seems excessive, you’re absolutely correct. But the thing was, she never told me to stop. Truthfully. The only reason I finally did is because of sheer cunnilingus fatigue. I just assumed she’d eventually have me stop, like literally every other woman I’d been with up to that point. Have you ever looked at your watch during any sexual act with another person, and been like, “Jesus, really?” Because I have.

Bittersweet is the most serene receiver of oral sex I’ve ever been with. She laid back on my couch and just watched me work with half-lidded eyes almost the entire time. She looked stoned. Every now and then her lips would part and she’d let out a soft sigh, or she’d run her hands up and down her thighs. If I was in a particularly good spot, she’d lightly scratch the back of my head with her nails.

The whole “ASMR” phenemenon didn’t exist at that time, but if it had, I’d say she was exceedingly good at getting that reaction out of me. Eating her pussy was *relaxing.* I know she came more than once, but I have no idea exactly how many times because her orgasm reaction is so subtle. Just the tiniest bit of tension in her muscles followed by a long slow relax and a little shiver.

Despite how long I ate her out I still felt pretty apologetic when I came up and admitted I couldn’t go anymore. She smiled up at me and just said, “That was so nice. Here, let me blow you.”

I know. Like the friendliest stewardess. She was an interesting woman.

I stood up to get some feeling back into my legs and she knelt down in front of me. I’d managed to get my jeans off all the way while eating her out so at this point we were both Porky-Pigging it, which I found comical.

Remember when I said her handjob had me close to cumming in less than five minutes? Her blowjob got me there in the same amount of time, and I was so exhausted from eating her out that when she started I was *soft*.

So there’s no way to say this without it sounding like a fucking humble brag, but until Bittersweet, not a single woman has ever been able to deepthroat me. Yes, yes, boo hoo, etc. I’m not complaining about it, but I do want to mention it because until that moment, I had no fucking idea how goddamn *amazing* it is. I mean, holy shit, not to reduce the immersion of the story or anything but just…it’s *so great*. And I know that can’t be easy, so seriously, if you’re reading this and you have “deepthroat artist” somewhere on your sex resume, thank you. Thank you **into eternity**. You all deserve LeBron-sized contracts and endless endorsement deals for the Sex Olympics.

Bittersweet was so good at sucking my cock that after a mere sixty seconds I was already saying, “Holy shit. Oh my god. What the fuck.” It was flabbergasting that a woman who couldn’t even take her pants off properly could make me cum as quickly as she did. I didn’t even know what to do with myself to fend it off. At one point I think I was just beating my own chest like Mark Wahlberg in “Fear” to distract myself.

The first time she took me all the way to the hilt I let out an immediate and impressed, “Whoa.” Then she did it again. And again. And after a few seconds it was obvious she could just do that as many times as she wanted and I lost it. I couldn’t turn my head away so I just watched her steadily and methodically throat my cock, feeling that velvety vice clasp around me over and over until I couldn’t take it anymore. I barely let out a “Oh, fuck, I’m gonna-” before I just *was*, and there was no stopping the flood.

Not that I needed to worry, because Bittersweet took me to the hilt and I’m not sure that any of it even ended up in her mouth.

After she pulled off of me, and cutely wiped her mouth with the back of her hand, I lifted her up to her feet and kissed her. I’m talking a full-blown *Ryan-Gosling-in-the-Notebook* style kiss, that’s how in love with her I was in that exact moment.

She rested her head on my chest for a moment, then looked up at me and said, “We can’t fuck tonight, my pussy is too sore now.”

“Can you spend the night?” I asked, and realized I had only maybe asked two other women to do that.

“Duh,” she responded.

“Do you want to do anything tomorrow?” I asked, hopefully.

“I can suck your cock again if you want,” she said, pulling on her panties and smiling. “I know you liked that.”

“YES, OKAY,” I said way too quickly and in a much too loud voice, and then added, “But I was thinking like walk at the park or go out to eat or something.”

She said she’d think about it, and then all of those things ended up happening. Bittersweet ended up staying at my place for a few days before going home. Then she came back every other weekend. Then every weekend. Then she got a job closer by and she pretty much moved in with me. I’m not sure if we ever, at any point during the eight months we were seeing each other, referred to ourselves as boyfriend and girlfriend. But we clearly were.

I wish I could say it was an overall happy ending, but the truth is we split up for a very good reason, and that whole sordid affair is pretty personal and not exactly Gone Wild Stories appropriate, so I’ll just say that *drugs* are a helluva drug, and leave it at that. I don’t know what became of Bittersweet after she left, but I can honestly say she is one of exactly two women in my entire life that I can say I both loved and still love.

Source: reddit.com/r/gonewildstories/comments/6ewq8v/mf_the_first_woman_to_ever_deepthroat_me