My First Time Having Sex Was a Disaster

My first time having sex was a disaster. I was 17. (Senior) She
graduated a year before me and was way more experienced. Her
name was Allison.

Every time she saw me she would ride my dick so hard. I put on this vibe that I was cool as fuck and she was going for it. She was super aggressive and called me sexy. This threw me off, I don’t feel girls should be doing stuff like that, it feels sketch, the roles should be
reversed. Anyway, I was a pussy.

All my friends knew her and I cared too much about what they would think of me if I tried anything with her since she’s a ‘hoe’ and ‘not that good looking’.

By pure luck, I ended up making out with her at a party across the
street from her house. We snuck outside (from the party) and went
to the front of her house where we made out. She literally straddled
me while we kissed, it threw me the fuck off hard because I hadn’t
made out with about 1-2 girls before this and they were nowhere
near as aggressive.
She fucking had her front door open and told me
to come in!
(She wanted to get dickeddd down and I knew this) But, I
didn’t go inside because her parents were home and it was ‘too
for me. (Pussy) I ended up taking her 
number as she went
in for the night. I went back to the party and felt defeated regretting
my whole life.

The next day, I was with my other boys in a house being built (pretty
much done, working lights, carpet and flushing toilets) smoking weed and she called me. Me being a pussy back then, I couldn’t talk in front of my friends since I didn’t want them to laugh at me so I went upstairs in private and talked to her.

It was about 7:30PM, she said we should chill and I took the biggest risk of my fucking life, I wanted so badly to say “I’m busy, but I said lets see what happens, I said “come over.” Mind you, I live with my
Indian parents who have never seen me bring a girl over ever.
They don’t even like me having people over at all. I told my friends I
had to go and went home to shower and shave. I cleaned my room
and set up a nightlight in there so I could see what I was doing
without having the light on.

She got here. It was about 10:30 at night, my mom is at work and my dad is asleep. She came dressed in a big tee, some sweats, Sperrys
and sick. I was like “ewww ur sick” and she said “so ur not gonna kiss me?!!” with some puppy dog eyes and of course my pussy ass was like “of course I am” and made out with
 her right there in my driveway.

I looked like a boss though, I was putting up a huge front by being ‘confident’ but I was nervous as fuck.

By this time, I had been reading Boytoy’s diary for months and knew I had to lead the situation.

I grabbed her hand and walked her up to the garage I came out of. (That was half-way cracked since I was sneaking her into my house) It was dark in the house so I grabbed her hand tight as she was
holding my waist with her other arm and walked her through the
kitchen into the living room. Going past the living room I have to
walk past my dad’s room, (the door was open, he was snoring loud)
she was nervous. She didn’t want my dad to wake up and I REALLY
DIDN’T WANT HIM TO WAKE UP so I picked her up and carried
her (she was slim, nice smooth one-tone skin, just not really super there in
the face)
past the room where she put her head down into my shirt
holding on to me with her life all the way up the 16 stairs I had
memorized, then put her down at the top still holding her hand the
whole time and walked her into my bedroom that was already set up
with condoms on the windowsill beside my bed.

Condom sex

(She wasn’t even expecting me to use them, I suspect this is why bitches are always preggo) (Not gonna lie, it’s hard to get a condom on in the
moment especially when putting up with last minute resistance. It’s easy
to put a condom on with a girl you already slept with and know you are
going to fuck, but when fucking a new girl that’s not all the way
‘comfortable’ sometimes you just gotta slip it in unexpectedly and if you
paused to put on a condom she’ll just pull her pants back up) [She is
thinking now when before it was all emotions]

Sex on my bed
My bed used to be up against that window.

My room was immaculate. Clean sheets and nightlight on.

As soon as we got in there, I roughly pushed her on the bed. I was
man handling her
 because that’s what I read was good to do. She
legitimately fell for it, she was like “so how many girls have you
snuck up here like that?” I was like “don’t worry about it lol” and she
lol’d. (The answer was 0)

She’s on my bed fully clothed, but I had did my RESEARCH. (This is why I think it’s so cool that some guys just KNOW shit like this, I had to ‘read’ about it, dont care tho, I’m in the top 5% of guys if not top 2% when it comes to the whole package I’m just shy of some dollar signs currently but not for long) 

I told her I would massage her, she was laying flat on her stomach. (She wasn’t being aggressive anymore since she wanted me to take her)

Sexy Girl
This is how she was laying on my bed with me on top of her.

I had read, pull down pants+panties AT THE SAME TIME so you
don’t get stuck anywhere and you need do it quickly and sneakily. I got a few fingers in her waist band then pulled her sweats and yellow lace panties off. Defenses down since pussy is now OUT. Then, I pulled my shorts off and I was hard.

*I was not about to eat her pussy, I thought that shit was gross at this time. Nowadays, I’ll eat pussy in the 69 position or if I can’t keep it up for some reason so long as she is super clean, has no odor and doesn’t mind
getting face fucked for 10min. (Then I might return the favor)

I moved her by her legs and tried putting a pillow under her back
until she says “why does every guy do that?” (Fucking hoe. Don’t say shit
like that when I’m about to go in you.)

Anyway, I had to put the condom on and it was a mother fucking bitch.

My dick kept going soft and I was too pussy to make her suck my dick. (You do so by telling her to suck it and putting it in her face while grabbing her head) 

I started jerking off and nothing happened. She wanted to fuck so bad. She was rubbing her pussy up and down on my limp dick and I
still wasn’t getting hard so I started finger fucking her greatly.

I was a pro at it from the jump, I could tell exactly where her clit was and where her G-spot was and how to massage it without being
uncomfortable. (I’m a natural at sex, kissing, fingering)

I have the entire 2nd floor to myself. I live in a 5 bedroom house with
my parents and dog. Upstairs has 4 bedrooms, 3 of them with beds. I took her from my room to a different bed, (picked her up) I was
super hard.

Sex on bed 2
2nd bed.

In my head I was like “yes ima fuck this bitch finally!” But then when came time to put the condom on, I went soft again. I told her “follow me” this time and we walked to yet another bed to see if I could
function over there. (She said “wow u got me walking naked around ur
whole house”

Sex on bed 3
3rd bed.

Well, same shit happened here to the point where I’m just plain
embarrassed and pissed.

I walk into the bathroom with my little LG Virgin Mobile phone (how ironic) and got on XNXX to try and jerk off to some porn while she waited disappointed and bored on the bed.

Still no success, so I went back to her and said “do something to make me hard.” (I wanted her to suck it but I didn’t know how and she looked like she didn’t want to)

*I genuinely didn’t think anything about my size here, and she didn’t say I had a small cock even though mine was literally like 4.5 inches at the time.

Instead of giving me a hand job like a normal bitch, she pinches the tip of my dick (head) and legitimately thought that was going to feel good for me. I was like “aite this shit not gonna work.”

I sent her home and felt like a pussy. I never heard from her again.

I tried texting her like 3 times and she never replied once. I don’t blame her.

Thankfully, I’m not a pussy anymore and shit like this doesn’t happen to me.

What I Would’ve Done Differently

  • Stop thinking about it so much, she’s just a dirty little hoe.
  • My friends probably don’t get laid as much as me, stop caring about what they think.
  • Actually be confident and not fake it. (Didn’t matter here tho)
  • Not hit up girls after I fucked unless they hit me up first and I’m sure she wants to see me again, or else I’ll end up hurting my own feelings.
  • If I’m a virgin or haven’t been getting play lately, lower my
    standards or else I’ll continue going without sex wondering why I can’t get it.  
  • Learn how to tell a girl NO. I will not tolerate kissing a sick bitch. 
  • Never show a girl I’m pissed, it’s gonna make me look like a pussy,
    what I should have did was laugh it off and say “idk whats wrong with me tonight,” and continue kissing, fingering her until she came a few times and let her sleep over or go home (doesn’t matter)
    and try again tomorrow. 
  • Realize regret is a terrible thing to do to myself and dwelling on
    past events is no better. Move on and get better. 

– Written by Brandon Ramlal