Back in my highschool days, my bestfriend was the typical tomb boy. She was great, cute and incredibly competitive. She was the youngest of 4 girls so I could see how hot she’ll get in the future. Fairly platonic relationship, but I can’t say I didn’t think about asking her out a few times.
Fastforward past highschool, first year in college, one of her older sister throws out a massive party. I sneakly ask my bestfriend to come. Their house is pretty much a mansion, when I come by there’s over 50 people there. My bestfriend and I are clearly the youngest there. We spend time together getting drunk and every chance I get I try to snoop on her older sisters. They were dressed sluttier the older they got. I still remember masturbating to her oldest sister’s prom photos back in the day so seeing her in a short skirt and a deep V cut black shirt was incredible. We played some games and I took way more shots then I should have. People started to leave, but we kept on going and I eventually mentionned I was still a virgin. I got a pretty big laugh out of my confession.
The rest of the night sarted to get blury from there. I remember that I brought an inflatable mattress to sleep on, but as my drunken self saw an empty bed I though fuck it. I undressed to my boxers and jumped in. I fell asleep fast and woke up to the door closing hard. Startled, I got up trying to recover my clothes in the pitch black room. I felt a warm hand on my chest:
“Ohh it’s you”
Unfortunately, I had no idea who it was. As I tried to open my mouth, her hand started to caress my skinny body. I couldn’t see anything inches from my face, but what I felt was out of this world. I was rock hard, but she hadn’t felt me yet.
“Let me teach you a few things”
She pushed me on the bed and I hear our clothes dropping on the floor. She turns around and sits between my legs, still not touching me.
“First lesson take of my bra”
I give it my best shot with both my hands, but my clumsy 19 years old self is so damn clueless. I try my best, but that bra was holding on to some heavy things upfront.
“Real man only uses one hand…”
I keep going and finally clic! Her bra slips off and she pushes me on the edge of the bed. She lays on her back and caresses my neck. I though she was going to kiss me, but she pushed me a lot lower.
“Lesson 2, always make her cum first”
It was my very first time anywhere near a pussy, I obviously had heard of a clit, but I had no idea what I was doing. She took her time, helping me every step of the way. When I finally was doing something right, she told me to keep going and as a stupid guy I though it meant go faster. I kept trying, my tongue was killing me, my dick was stuck in the mattress and my neck hurt, but I couldn’t stop. She was so patient and encouraging, I couldn’t let her down. I must have eaten out for an hour still no results. All this time, I tried to see which one of the sisters it was, but I couldn’t tell
“You’re so close… take off your clothes you still deserve a little reward for trying”
I was waiting eagerly for her to say that. I got on my knees and drop my underwear as fast as I could. She put her tiny hands on me and immediatley stopped.
“Oh no no no no no… with that thing you need to master lesson 2”
She pushed me off and took my head right back between her legs. Somehow, I was a little better, she got a lot louder. After a few minutes, I finally did it. She started to squirm and moan my name while her orgasm took over. I can tell you there isn’t a better feeling in the world then that. She grabbed my throbbing hard cock in her hands and says:
“Thank you and good luck 😘”
I got up took my clothes and went to sleep in the living room. To this day, I still dont know who it was. I still see them from time to time and they all grin at me. I know they share everything so I’m guessing they all know the story by now. Whoever it was, her tip changed my life for the better 😁.
Source: reddit.com/r/gonewildstories/comments/11ynn6s/the_best_tip_i_got_from_my_bestfriends_older