u/Ashamed-Garbage-4814

So many of you liked my previous and many of you subscribed to my substack. I am grateful from the bottom of my heart. Just know, if you are here right now, you are invested early like bitcoin in the early 2010s. We are going to blow up baby!!!

Anyway, so where were we? Yes, I left you like I just left Victoria with the biggest teaser imaginable. But what do they say - if you fall down, you get back up and that I did. However, it was never actually my intent to have sex so soon. So in my normal viewing of Snap stories this girl made a joke I found so funny. It was a double entendre of “mayai” and eyes. It gave the vibe of early Ronoh before Majimbo ran with it and became a sellout (I am still salty we don’t give Ronoh her flowers). Anyway, innocently, I commented on her story and like clockwork we vibed. Our conversations were so dumb yet so easy; we could talk for hours on end. There was no anxiety, no waiting for texts, no doubting if you said the dumb thing. In one such conversation I mentioned that I had gotten a new sound system and if she ever comes to my place she can be as loud as she wants. I don’t know if I did it intentionally but this was her cue that we should turn up the notch a few, sexually.

Plans were made and she was to come to my place and that she did. Let me describe Lauryn to you all. She came from a middle to upper background yet she was heavily influenced by Rastafarian culture and as a result she had locs as she would call them. She was heavily melanated and had the pinkest lips that struck such a magnificent contrast on her face. She was short, a bit thick but not as much as you would think. Her greatest asset came in the form of her heavenly shaped, massive and soft to touch breasts. She could wear any cloth and trust me her cleavage would steal the show. And she wore glasses something I admired at the time. Let’s get back to it, she did come to my place again this was the first time we saw each other. Looking back at these memories after the whole femicide, drugging and falling from apartment floors events makes me think I was quite reckless considering I lived on the 7th floor.

Anyway, we chatted up a bit and she made me laugh a lot. And we got to what brought us here. I remember we made out so heavily I can still hear her breathes her moans as I type this. However, we didn’t actually fuck that day as she said it wouldn’t look right if she gave it up on the first day. I am a firm believer of consent and that was that I escorted her to the matatu stage and that was that. However, we soon set up a next meeting and this time I knew we are going to fuck. She came looking magnificent as ever. This time there were no jokes, no laughs and certainly no endless chitchat we knew what brought us here. I remember holding her massive breasts and being amazed at how soft they were almost squishy. If I describe how the sex was I would be lying. All I remember is we fucked on the bed, on the floor while standing and at some point my roommate knocked the door while I was mid strokes. I answered his call while fucking and was like “Yeah, I am kinda busy right now”. Funny thing if memory serves right I took so long to cum I guess this was a benefit of anxiety. Side note I never told her I was a virgin so she thought I was really good at sex (penetrative sex at least).

Nonetheless, that was the start of a relationship, situationship and FWB situation all in one. Well if everything was so perfect I would be writing about her as my wife right? But it wasn’t I don’t remember the exact sequence of events but the dominoes started to fall. I remember she gave me a UTI or was it an unknown STI. It started so quaintly just a feeling deep in my urethra then the itchiness and before I knew it I was scratching my dick vigorously and pissing every time. This took a couple of antibiotics and several awkward visits to the family doctor who knew my mum personally and she was a woman so I had to show her my dick. Any of you who have never experienced a urethral swab just know whichever deity you worship, loves you. Because it is painful as fuck.

I believe I was too naive but I think she was also fucking someone else. Because the STI didn’t make sense at all but I can never be too sure. She also got pregnant at some point and lucky for me she decided to take the emergency pill on her own volition. And in the middle of this I decided to tell her I love her and she was requited the same feelings. However, I soon met another girl and my attention waned, followed by whatever feelings I had of her. I know I am not innocent in this story and I do not believe she was guilty but I will forever be grateful that I lost my virginity to a cool ass rebellious woman.

So that’s it, that is how I lost my virginity. Underwhelming maybe but it is deeply etched in my memory. Thank you for reading till this point, it might have been short but I wrote this and “How Not to Fuck” back to back. Anyway, the next story is one of the few girls I have had mind-blowing sex with i.e. the sex was like a drug. So see you next time and have safe and enjoyable sex in the meantime. Again I am asking for you to subscribe at https://substack.com/@squaredjaw

Well I have had a lot of things happen to me in the pursuit of sex but perhaps none as funny as the story I am about to tell you. If you have read my previous two stories “Preamble” and “Art of Fingering” you must know by this stage I am at the precipice of losing my virginity. Picture this: I am a horny and idle 20 year old and what do I do with my time I chat up random girls online on Facebook, Instagram and Snapchat. I happened to be successful with one girl who we shall call Victoria. Now Victoria was a plain looking girl with a dirty mind. We would talk, flirt and chit chat about matters sex, porn and blowjobs. At the time this was new territory, I knew girls get horny but I believed that it was up to us guys to get them there. A very dumb way of thinking that my fellow brethren still hold dear.

Also at this point in time I had moved out of my parent’s place. I was in campus in my second year of study sharing a dark bedsitter (seriously the window faced a dark corridor you had to have the light bulb on 24/7) with my cousin. Anyway, our chats soon became a dare, or rather, an invitation to actualise them in person. I told her of my recent life developments and she should visit. I don’t know how I did this or the atmosphere was different back then but women would often meet me for the first time in my apartment. If you are a girl reading this please don’t do that ever go for a date first and if you are a guy stay safe get to know a girl first.

Anyway, she agreed to come on one rather dull weekday in which I had no classes or rather skipped classes; guess we’ll never know. I want you to know that I had never had sex and as the eldest sibling who do you think “taught” me about sex? If you guessed porn you are right. Well in porn the men fuck and fuck for hours more like 20 mins to be precise of constant penetrative action. I would later come to learn it is just an amalgamation of shots and most porn is quite performative. I then had the bright idea of masturbating so that when Victoria comes she will be enthralled by my sexual prowess as I drill her mercilessly for hours. So me, my stupid head, my phone and a bottle of cheap lotion went into the bathroom, watched a porno, masturbated and came and as usual it was not gratifying (as cumming from porn always is).

True to her words, Victoria was quite the daredevil and she did indeed come. If memory serves me right she also skipped class. Well, Victoria, as I had mentioned above was a plain looking girl, she didn’t have extraordinary conventionally attractive features but she made up for it with her glistening melanated skin and perhaps her most potent tool; her mind. So she came, sat on my bed as I had no sofa at the time. And then we talked and talked and after talking we talked again. Then she stopped talking tied her braids in a knot, you know how girls do it before they give you head yeah that. And then with the most straightforward voice she said “I have to be home by 5 so do you wanna do it or not?” Obviously, I replied in the affirmative didn’t she know I was about to restructure her insides?

Well here is the thing I didn’t, in fact, my well-decorated veteran failed to rise to the occasion. It was a mixture of anxiety (it was to be my first time after all), porn desensitisation and lastly normal physiological human function i.e. the old refractory period. Well Victoria tried to give me head but it didn’t work. I said maybe if I finger you I might get hard and she agreed. She was quite wet and the more I fingered the wetter she became. Her vaginal juices turned white on my fingers and on her vulva; it was a sight to behold against the contrast of her darker skin. Nothing worked, however, and eventually she got annoyed and dressed up and left. I don’t remember much but that was the last time I ever saw Victoria and our conversations quickly dried up.

At the time I thought I had fucked up monumentally; it was time to accept my life as an eternal virgin. However, I would soon have sex in a matter of months which forms the basis of my next article “How Not to Lose your Virginity”. So boys and girls what have you learned today? Porn is bad, performative and not representative of real life sex. So if you are going to take anything from this is that don’t try to be like what you see in porn. And if you are a guy masturbating before seeing a girl is the utmost worst idea you can think of. Kindly subscribe I have a lot of stories and your subscriptions will motivate me to write all of them.

https://substack.com/@squaredjaw

So where were we, we last talked about Mwanzo my nextdoor neighbour with whom I broke my kissing virginity and basically the first woman I ever touched. Well that was me at 16 turning 17 but I lost my actual virginity when I was 20. So what the hell happened in those 3 years. Well I fingered a lot of girls is one and by a lot I mean like 5 or so I cannot remember. So the stories below are myriad events that happened 10 or so years ago.

Well after Mwanzo, your boy broke out of his shell I was shy but not so much after all I had touched boobs, had someone suck my dick and fingered a girl (well at least attempted to). The main problem with porn (well there are serious links between human trafficking and porn, so look that up) at least for me has always been the unrealistic standards. Fingering always felt for me at a tender age like a competition of how much and how fast you can fit into a girl’s vagina; according to porn at least ask the fisting experts. I am no woman myself and some girls might like it but I don’t think that is the general consensus of what you need to do.

Anyway, if memory serves me right the next girl I engaged with was Alexa. We met at a movie shop (I know I am old), I was with my friend and we had gone to get some tv shows uploaded on our flash disks. She was very friendly so we talked and exchanged contacts. And before you know it, she came to visit me. I don’t remember how we ended up at the back garden of an unoccupied house in our estate. If you read “preamble” you might remember my grave error of not living in the servant quarter. I feel that one decision delayed me losing my virginity by 3 years. Anyway, we started making out; she had these massive succulent breasts any gender would like to hold and squeeze. I remember being amazed at how heavy they were and the hot sun made sweat drip in between them; a sight to behold. Anyway, we did make out and I fingered her; at that moment in time, penetrative sex was not an end goal for me and I hadn’t discovered the art of giving oral sex. So that was that and after she left we stopped talking for whatever reason. I did see her in a talent search tv type of show as a contestant years later though I doubt if she remembers me.

Then there was another. I have to put a disclaimer that my biological parents have always lived apart. So this happened while I was at my mother’s place. My mother was not so financially gifted and thus lived in a more densely populated part of the city. Instead of villas and estates here we just had tall apartment blocks and narrow muddy alleyways. Anyway, I once met a girl while walking to the shops and as a horny kid I mustered up the courage to ask for her number. She obliged and gave it to me. That same day I told her to come to my mum’s; and since there were other people at home. I told her we go to a different floor. While she was looking over the not so beautiful obstructed view of the Nairobi city skyline I stood behind her. She got a feel of my crotch and I realised that I hadn’t focused on a single thing she said and neither had she. I went on to kiss her neck while my hands traced down her pants to reveal a bushy vulva. The first I had experienced and if I am not wrong the bushiest till date. Anyway I did finger her but it was for such a short period as I was afraid of being caught.

Now on to my last story of the day. Back then Facebook was the huge platform where people talked and met online. So I had DM’d hundreds of girls at this point looking back at my old account I had the lamest icebreakers. “Sasa msupa”, “Umeiva sana”, “Can we be friends” and my favorite “I am bored let’s talk”. Anyway one of these worked on a really beautiful girl; Brijo. We talked for a minute and eventually met. I’d like to think that Brijo was hornier than I but she had a boyfriend an important detail I would later come to learn. Nonetheless she did come to my mum’s house twice. The first time we went to the very top floor, I had found a secluded place in the rooftop where water tanks were being stored. And in the view of the unobstructed Nairobi skyline we made out. I don’t remember it being a good or a memorable kiss but I was heavily attracted to her. Guys will understand the feeling of punching above your weight. And then my hands did the thing, traced slowly across her beautiful face to her well sculptured breasts and finally to her pants which barely held in an abundance of hips, unbuckled her belt, opened her buttons and fingered her. Well more like inserted my fingers in and out of her vagina severally and vigorously.

Anyway she did something with her hands over my crotch whilst I still had my pants on and I came; a thing I have not experienced since then. More like rubbed my crotch and my dick and in between then grab my dick quite hard. Whatever she did was enough to make me cum. She later felt guilty that she had a boyfriend but still she insisted on coming one last time to see me which even at my young age I found quite amusing. When she did come, she cried but let me finger her one more time; crazy I know. My aunt walked in on us and thank god she never said a word to my mum. True to her words that was the final time I saw Brijo, I would later pop into her in uni and near uni there was the hi’s but nothing beyond that. She now hosts a not so big tv show on one of Kenya’s main channels but a tv show nonetheless. She might be the most famous person to be mentioned in these stories.

If you have reached this point by now you would have realised that this post is not about fingering. But rather my early experiences with the female vulva of which I admit I was quite clueless. This post has been too long for my liking. Next time I will perhaps talk about the time I thought for sure I was to lose my virginity only for my penis to fail me, I could not rise to the occasion, and how I finally lost it. Thankssss. Please subscribe to the substack https://substack.com/@squaredjaw