When I was 19, I found myself still a virgin. While my buddies started hooking up with girls the previous year or two, I never had any luck. I was less than a week away from turning 20 and was starting to get more and more anxious because I hadn’t even kissed a girl yet.
All the girls even remotely considered candidates at high school were already pairing up with other boys. I found myself on an island, frustrated. On the weekends, it would be my buddies with their girlfriends and me, always the odd man out. It really started to piss me off.
I knew I wasn’t bad-looking or anything. I wasn’t a 6’3” bull with an abnormally huge cock, but I considered myself decent enough looking, was in decent shape. Even my dick wasn’t bad; it was just a shade above average length. Even my height was decent, tall enough for most superficial girls. My looks weren't the issue.
Then, one day, it finally happened. At a house party, I met a girl named Amber. I had known her since grade 3, but never really talked to her, as she made me nervous. She was a petite brunette, standing at around 5’1", slim, and had a pretty face. We were all drunk, and I’m not sure if she was dared or if she just took pity on me after maybe talking to my buddies' girlfriends, but at that point, I didn’t give a shit. She took me upstairs and we started to make out, and it was about to go down.
This is where it gets embarrassing. This isn’t one of those stories where a virgin magically loses their virginity to a hottie, fucking her for 45 minutes, making her cum, and the two of them falling in love for all ever after. No, my first time was bad. And awkward as fuck.
In hindsight, I had likely watched way too much porn and basically tried to repeat what I saw in the movies. I was overzealous trying to kiss her, probably way too much tongue, and she told me to settle down. Then, when she unzipped my pants, I thought she was going to start giving me a blowjob, so I tried to stick it in her mouth, and she got mad and stopped me. She then shoved me onto the bed, started giving me a hand job for a couple of minutes, and then got on top of me and started kissing me again. I had no idea where to put my hands, as I didn’t want to piss her off again, so I basically just laid there like an idiot. But by just lying there doing nothing, that frustrated her again.
She sighed and then took her panties off, left her shirt on, grabbed my dick, put a condom on it, and stuffed it inside her tight pussy. I was no longer a virgin, but this wasn’t exactly enjoyable yet. Then she started bouncing on me, which got me really excited, as she was really tight. But it got me too excited. She rode me for about 50 seconds, and I couldn’t control myself. I tried to think of something else, but it didn't work, and I started ejaculating into the condom. Like a fucking loser two pump chump. She looked at me in disbelief.
So embarrassing. She was very pissed off, and I apologized, but she got dressed and left the room without saying a word. I laid there on the bed like a fucking idiot, condom still on and full of my own semen. The whole thing lasted maybe 10 minutes, and that’s being generous.
It was the worst “popping of a cherry” I could have imagined. I was no longer a virgin, but the experience was traumatic. Not only was I in my own head even more after it, but Amber would go on to gossip to the other girls about what happened. What a twat.
My buddies heard from their girlfriends and were nice about it, as were their girlfriends, but as far as any of the other girls at school, it went from radio silence to being on some other planet entirely. I was a lost cause.
As a result, I went another full year not even touching another girl. I might as well have stayed a virgin. All I did was jerk off every night, watching more and more porn.
My best friend, Greg, and I would often hang out at his condo with him and his girlfriend, Lia, and play video games. He shared the condo with his super hot older sister, Brooke, who was like 6 years older than us. I, along with all of Greg’s buddies, had teased him for years about how hot his sister was, and it became a long-running joke. We weren’t kidding, though; she was fucking hot. She had medium-length dirty blonde hair and an incredible body, huge natural tits. I sometimes felt bad for Greg, as whenever she was around, he obviously knew what all of us were thinking.
On this particular night, Brooke was at the bar with her friends, and it was just Greg, Lia, and me. We played video games and got way too drunk, before eventually Greg and Lia made their way to their room at like 2. I was in no position to drive, so they told me to crash on the couch. I told Greg to let his sister know that when she comes home, I’d be on the couch so as not to freak her out or take a baseball bat to me.
I passed out immediately, but heard the door open when Brooke came home; it must have been like 3 in the morning. I fake-sobered up with the thought that I should probably say hello to her.
She must have come from the club, she looked fucking smoking. Wearing black shiny leather leggings and a ridiculous, tight sparkling blue shirt with her huge cannons on display. She was a bit stumbly too, as she must have been hammered as well. I summoned the courage to speak first.
“Hey, Brooke.”
“Oh, hey Josh! How was your night?”
She sat on the chair beside me and I think I had my first real conversation with her in my entire life. I don't know if it was the booze but the conversation flowed very smoothly, and even was a little bit flirty. We even touched on me being single, and I learned that she was recently single as of a few weeks ago when she broke up with her boyfriend of about 2 years. I was fucking tired though, and fading fast, which she could see. I stood up to pour myself a glass a water and she stood up to make her way to her room. I told her goodnight.
She smiled at me and gave me a hug, which we had never done before. Her big tits pressed against my chest were hard not to ignore. She gave me a little smile and then went to her room and shut the door. The whole encounter gave me an erection as I went and passed out back on the couch.
The next morning the four of us, hungover, made breakfast at the condo and ate at Greg’s. Greg and I chatted at the table while Brooke and Lia chatted on the couch. I thought I noticed Brooke constantly looking over at us, but figured it was my imagination. Shortly after I left for home.
Later that week I received a Facebook message from Brooke.
*Brooke: Hey Josh, how’s it going?*
She didn’t have my phone number or anything and I wondered what the hell was going on.
*Josh: Hey Brooke! What’s up?*
*Brooke: Was nice chatting with you the other night, I know we’ve known each other for a long time but I had no idea you were so easy to talk to!*
*Josh: So are you!*
*Brooke: SO…. i know this message is a bit out of the blue, but I hope you don’t mind me prying, but I was wondering why you’ve never have had a girlfriend?*
I was a bit stressed by the question. Why was she asking?
*Josh: I’m not sure! Just my personality I guess, girls are weirded out by me?*
*Brooke: That can’t be the case. You’re very normal. Is it because of that one-night stand you had a year ago? Lia told me. Sounds like some of the bitches in high school might have ganged up on you?*
Well….there was no lying about it now.
*Josh: ummmm……yeah I imagine that’s probably part of it. I hooked up with a girl and it wasn’t very….how shall we say….well received.*
*Brooke: If you ever want pointers on what to do with a girl, I’m willing to help. Just text me, here’s my number. Just don’t tell Greg.*
I was oddly excited at the opportunity for some guidance, especially from a girl. And an older girl, no less, who I imagine had plenty of experience. I took her number down and added it to my phone.
Over the next number of weeks, I would text her questions, and back and forth we could go. I can’t lie, every time texting her would result in me jerking off, as it was basically sexting. I made sure Greg was unaware of any of this contact.
One late Friday night at around midnight, I received a text from Brooke.
*Brooke: Josh Josh Josh, wht are we going to do abuot you. How do we get you confdent around the ladies….?*
The spelling mistakes led me to believe that she had another wild one at the bar.
*Josh: hahah you sound like you’ve had a night!*
She ignored my accusation.
*Brooke: can i ask, i know weve been texting for a whle now, can i ask is everything well-equipped down below? ;)*
*Josh: umm yeah, I dont think thats the problem! Nothing wrong down there :)*
*Brooke: was girl chatting with Lia the other night, she told me about a girl in school that thinks you cute. She’s gonna try and set up something for you! But we gotta be ready. Understand?*
*Josh: Who!*
I had recently begun a new friendship with a chick named Bella, she was super cute, a little nerdy and awkward like me, and we were becoming fast friends. Bella had a really nice rack too, not as big as Brooke’s but bigger than most of the girls in class. I was hoping Brooke was going to say her name
*Brooke: some chick named Bella.*
*Josh: fuck that woudl be amazing! She’s so cool. And cute!*
*Brooke: sounds like this chick has some big boobs thouhg, we gotta make sure you now what to do with those. And we gotta make sure you pace yourself in bed, we gotta impress her.*
*Josh: i think your advice has been great, I can roll with it*
*Brooke: do you wanna do a dry run?*
I did a double-take, making sure I read that right.
*Josh: What do you mean?*
*Brooke: With me? We can do a training session so to speak. I can show you what girls like.*
This was a dream. The thought of fucking my best friend's hot sister was extremely hot.
*Josh: ummm…. Are you sure? I could sure use your expertise but I don’t wanna make it weird?*
*Brooke: we wont tell anybody. PLus, i think you’re pretty cute. Let me help you. Greg and Lia are going to the mountains for the weekend, so why dont you come ove here tomorrow night and we can have some fun. Spend the night.*
I was rock hard responding to her offer.
*Josh: that honestly sounds amazing! And fun! It’s a plan!*
*Brooke: oh make sure you jack off 30 minutes before coming over. As we’ve discussed, you’ll want to do that before you take miss Bella out on a date too. Clean your pipes.*
*Josh: Got it! Thanks Brooke, this means a lot!*
The next day couldn’t come fast enough. As per her instructions, I jerked off before leaving for her place. She buzzed me up and opened the door and my heart was pounding.
She was dressed in jeans and a white tank top, and hugged me and brought me inside.
“Ok! First lesson. You jerked off already, right?”
“I sure did.”
“Good! Now let’s get buzzed. Not drunk, but buzzed. It’ll loosen you up”
We had a couple of drinks and chit-chatted on the couch. She noticed my eyes wandering down to her cleavage.
“See…right there. You need to have as much eye contact with me as possible. But not 100% eye contact. I want you to get caught looking at Bella’s cleavage only once while chatting with her, so she knows you’re interested. Otherwise, you look right in her eyes, got it?”
This was already proving to be a great advice session. I soaked it all up. We finished our second drinks when she abruptly jumped on me and started making out.
She advised me on the correct amount of tongue to use, and also made me grope her ass and hips just enough. She came up for air.
“At this point, it’s ok for you to start groping her breasts. But do it gently.”
I obeyed. Feeling up Brooke’s tits was the best few minutes of my life. She noticed my cock getting enormously hard.
“K now pace yourself. I can feel your cock getting way too hard. You don’t wanna pop when she gives you a blowjob.”
I nodded and forced myself to stop playing with her tits. It helped ease my erection down to about 50%. This was brilliant advice.
“Ok, so from what Lia told me, I heard you popped really early with that Amber chick, right. We’re going to practice controlling yourself. Go into my room and wait, I’m going to go get dressed in some lingerie, and I’ll be right back. And we’ll test you. Over and over and over.”
She left for her bathroom and I went to her room and sat on the bed, still rock hard. About 5 minutes later, she opened the door and came into her room. Fuck, she was looking like a million bucks. She was wearing black stockings, some high heels, black panties and a small black bra that barely contained her massive jugs. She sat down on her chair and told me the rules.
“Ok, I’m going to suck your dick, and I give really sloppy blowjobs. You need to control yourself, jerking off earlier helped, but if you feel like you’re going to pop let me know and I’ll stop. We can’t have you nutting in this poor girl's mouth.”
“Got it.”
She wandered over to me, spread my legs, unbuttoned my jeans and took my cock out.
“Wow, this isn’t bad at all. This dick deserves more action”
“Tell me about it!”
She placed it in her warm mouth and started sucking away. She wasn’t kidding, she loved the saliva. Gobs and gobs of it were dripping down my shaft. I had to stop her 2 times, but by the 3rd go at it I managed ot keep in control. It was fucking heaven.
“Ok, great job! Now I want you to suck on my titties, and then I’m going to titty fuck you, same rules as the blowjob.”
She brought her body up and I unhooked her bra and started massaging her amazing breasts. I licked the nipples and managed to stay in control. I even got Brooke moaning a bit, which seemed like a win for me.
I stood up and shoved my cock in her big tits and after she spat another gob of saliva in there I started fucking them. We had to stop once, Brooke felt it too that I was about to erupt in them. To distract me she slapped me hard on the legs which actually worked.
“Focus! No nutting! You haven’t even fucked me yet! All this foreplay is setting up for when you get ME off!”
She wasn’t wrong. So I calmed down, stuck my cock in her titties again and fucked them for a few more minutes.
“Great job! OK! Next stage. Time to eat my pussy.”
She got on the edge of the bed, spread her legs instructed me what to do.
“Don’t let your tongue seize up, and all the important bits are inside. Use your tongue and spell B-E-L-L-A over and over again with it. Suck on the clit too, champ, and she’ll be loving you.”
I obeyed and got right in there. It actually tasted better than I thought it would, and I went to work. I had Brooke moaning really good, and I decided to introduce a finger into the scene.
“Yes! Josh, that's amazing. Keep going.”
I loved eating her out, and found that there was no risk of me exploding early, so I really went hard at her. She was moaning loud enough for the condo neighbours to hear but I didn’t give a single solitary fuck.
To my surprise, Brooke orgasmed really loudly. She instructed me to stop after she did, for a few seconds.
“I can’t believe you haven’t done that before, that was really good. My pussy is ready for your cock now”
She bent over onto all fours on the bed and I stuck my cock in her pussy very slowly as she instructed. I thrusted very slowly at first so I wouldn't get too excited, as she instructed, and it worked beautifully. I wound up increasing my speed after a while and managed to fuck her really hard.
My balls were bouncing off her clit and I was starting to get the hang of this. I squeezed her bouncing tits from behind and sucked on her neck and back, which she really liked.
“That’s it Josh, girls love this. You know what to do.”
Confidence was flying and I moved her off the bed and positioned her on a chair and bent her over.
“There you go! Manhandle me, Josh! I’m your fuck toy!”
I started drilling her from behind and squeezed her bouncing tits as hard as I could go. I don’t know who the guy was, but I was really getting the hang of it. Brooke stopped giving instructions and we just let it flow.
I threw her back on the bed and fucked her missionary. We were both sweating pretty profusely, and as I fed my cock into her some more I felt her tighten up again, preparing for a second orgasm.
“That’s it, that’s it, that’s……” Her eyes closed as she had her second orgasm. I stopped again.
“Fuck Josh. That was amazing.”
“I'm almost ready to cum too, do I just cum on her tummy or do I ask her or what?”
“Ask her. Tell her “Where do you want me to cum” and she’ll tell you the truth every time”.
“Ok…..so where do you want me to cum?”
Brooke changed the rules.
“Where do you want to cum Josh?”
Finally some of my own input.
“I wanna titty fuck you again and cum on your face and tongue.”
“Mmmm ok. I'm a little bit more of a freak than most, some girls won’t like that, but you can do it on me, baby”
I wandered up to her chest again, and she squeezed her tits together. I used my own spit as lube and fucked them one more time. I felt the ache arriving in my balls and told Brooke when I was ready. She grabbed my cock and started stroking me, which I had never ejaculated not using my own hands. It was amazing.
She positioned my cock toward her mouth and opened wide, as I unleashed rope after rope onto her face and tongue. I was shocked I still had that much jizz in my sack after jerking off earlier, but Brooke found it.
“That’s a good boy”. She licked the tip of my sensitive cock a few times, and I collapsed in bed beside her.
“Now you let the girl go get washed up, and if she’s the type of girl who likes to cuddle, you cuddle. And you spent the night.”
“Gotcha!”
Brooke went to the bathroom and got cleaned up, and made her way back into bed.
“Just so you know, Josh, that was really, really good. Like, no complaints. If you fuck Bella like that, you’ll have her. I can’t believe how good you were, actually.”
She spooned into me with her ass.
“Thanks, Brooke, that was so great. I’m ready.”
We fell asleep, and I actually fucked her again the next morning. A week later, I had my first date with Bella, and by the third date, I managed to have sex with her, and we became a couple a month after that. And I like to think that it was 100% with the help of my best buddy's hot sister!