I’ll just cut to the chase, I used to be really heavy growing up as a kid. Getting made fun of, no girls liking me, all the classic hellish symptoms of growing up an overweight child. About a year ago I looked in the mirror and saw a 25 y/o overweight virgin, in between jobs, and in a really low place. The only silver lining to being let go from my job had been my increased time to focus on lifting and eating right. Since a year ago I’ve been able to lose 75lbs, bulk up with muscle, and see signs of a 6 pack but more importantly just maintaining healthy habits. But there was one more issue to tackle, my virginity.
A buddy of mine had asked me and some other friends of ours from college to come up to his parents lake house in Michigan for the weekend. Now keep in mind I had not been to any public events since my weight loss. I’m still very shy and protective of my body and still feel like I had not progressed to where I wanted to be.
Upon arriving I was greeted with all kinds of compliments and gawks. “Oh my god you look great!” Or some ranging from “dude are you okay it looks like you need to eat a steak.” It was all nice but I still felt like that chubby kid on the inside. ABSOLUTELY NONE of my friends knew I was a virgin, and if they did I’m not sure they’d be friends with me anymore.
As I rekindled with all of my old friends and their girlfriends, it was sobering. It felt as if I was the only bachelor in the crowd. I felt like this until I saw my buddy’s younger 20 y/o sister (we’ll call her Delilah) who I met one time previously my freshman year. She had been much younger then, barely in high school, but boy did she grow up. She had strawberry blonde hair with a nose piercing, 32 C cup tits, and jean shorts that struggled to contain her dump truck ass. She snuck out of the back door and made a b-line straight for the pool.
I was kind of drunk and feeling confident so I made my way over and introduced myself. She remembered me right away, and proceeded to say “wow you’re looking amazing”.
It was all innocent at first, me asking her how her classes were and her asking me about my job (or lack thereof). We took down a good amount of alcohol before she exclaimed, “You know I’ve been watching you since I was in the house, I noticed you’re the only one without a gf” I told her yeah it’s been kind of difficult getting out there. So she responds “I find it hard to believe you have trouble getting girls.”
We laughed and I said “well what about you?” She laughed again and took a sip of her white claw before saying “I’d let you”. “Let me what?” I said pretending to me dumb. She touched my leg in the pool and I instantly felt blood gush to my cock. “I’d let you fuck me” she responded.
Before I let another moment pass she was taking my hand and we were sneaking away from the crowd of my buddies and their significant others. Delilah led me to the pool room where she kept the lights off so no one would notice we were in here.
We were both cold and damp from the pool so we stripped off our clothes. Her nipples were erect from the chill and they stood at attention with goosebumps covering her tits. They wobbled as she shivered in place. I rose up to hold her and we kissed passionately letting our tongues swirl in each other’s mouths. She sat me down and started deep throating my member. As I grew harder and harder she could sense i was about to blow and stopped.
She stood up turned around so her ass was over my erect cock and sat down. Her pussy plunged onto the tip of my cock and I slowly watched the tip be engulfed by her pink wetness. It made a creamy sound as it slid in and she gasped “fuck”. She bounced on it once or twice before I blew a months worth of load into her womb.
She continued to ride and as she slid up and down, cum collected at the base of my dick. I held her still and unloaded the last of my jizz before pulling out. We made out a little longer before she disappeared into the house. I rejoined my friends and slapped my buddy’s hand with the same hand I fingered his sister with.
Source: reddit.com/r/gonewildstories/comments/ix8mtd/friends_sister_rocks_my_world_in_reverse_cowgirl
Good story
Great story. Did you hook up with her again?
I have not since but we text occasionally and talk on insta
High five (your other hand please)!
Amazing to experience cumming inside a woman on your first time, too.
You should ask her out for a friendly date and ask her is she’s into FWB’s or a relationship or just fucking random guys? If she wants a relationship, maybe you can go for it and gain some needed sexual experience and stamina. I would hold off on telling the virginity thing until you know her better though. You don’t want it getting out and having it embarrass you.