I was 14. It was the day before Thanksgiving of 2012. A Wednesday. My mother had gone to work and my brother was in Raleigh, NC with his girlfriend for a work convention. I had never done anything sexual other than a few kisses that involved tongue, but that’s it. D had texted me at like 7 o’clock in the morning asking if he could come over and I’m like.. “it’s 7am?? I’m not even up yet, plus, I have to wait until my mother leaves for work, which isn’t until 8am and I want to make sure she’s gone”. So, I told him to come over around 10:30am. He agreed. I immediately jumped up and ran to the bathroom to shower, SHAVE (the first time doing my cunt btw), and prepare for him because I wanted it to be perfect and didn’t want to have any setbacks. The whole while he’s texting me like “wyd?” and I’m like “..oh, you know, watching tv..lol” lying like a motherfucker.
Anyway, he ends up getting to my house early, around like 10am. Now, we hadn’t discussed doing any sexual activities. We were good friends and we had hung out alone before . Except, I was madly infatuated with this individual and he was mildly interested in me at most (at least that’s how I perceived it). We were watching tv sitting beside each other on the couch slightly cuddled up and.. the next thing I remember is leading him down the hallway to my bedroom. He asked me if I was ready and willing to have sex with him, and me feeling comfortable enough to say “No.”, I did. He said “Well, let me just take your clothes off.” I agreed. I was now naked. He was still clothed. He told me to reciprocate the same thing he did to me. His head got stuck in his shirt :/ it was awkward, as to be expected? I gave up and he said he’d just take the rest of his clothes off himself (which I suggested he do in the first place).
After he was down to his underwear he suggested he put on a condom. I hadn’t even thought of one! Thank God he brought one (although, in hindsight it should’ve been a sign that that’s really all he came over to do.. fuck me, which, I was surprisingly okay with). While he put on the condom, he said “Put on some Chief Keef.” REALLY??? You want to hear Chief Keef and you think I want that as background music when I’m about to lose my virginity? I didn’t argue with him any further and since he was still fumbling with that fucking condom I just laid across my bed diagonally with my legs spread wide. He finally turned around and I got to see my first cock. All veiny dark and thick, I couldn’t really be mad?? I’m still ambivalent around his dick. Anyway, he got on the bed, got in between my legs, and attempted to enter me… multiple times.
Okay, I’m skinny, I’m nervous, and I’m a virgin. It’s not really a good mix. Soon, he began to get frustrated and ultimately forced himself inside of me. I screamed out at the pain. All I felt was a sharp pain and tons of pressure. “What the fuck?” I said. “Sorry. Does it really hurt that bad?” he said. “Yes, just please go slow.” I said. After a few strokes, he decided to pick up speed. Somehow, he slid out too far and ended up shoving his entire penis into my ass.
WORST PHYSICAL FEELING I’VE EVER EXPERIENCED IN MY LIFE. FUUUUUUUUUCK. “STOP!” I screamed. “What? Does it really hurt that bad?” he asked. “I don’t know. Maybe we should find a ten foot pole, shove it up your ass, and then we can compare notes! Of course it fucking hurt!” I said, frustrated. He tried to cuddle with me after I obviously didn’t want to continue. He wasn’t large in length, but in width it felt like he could split me wide open. I kicked him out after that. We didn’t talk, text, or anything for a month. Maybe not until a couple of days before Christmas came around. We’re no longer good friends. That’s how I lost my virginity. It was shit, but what’re you going to do…
- Name: Ambivalent
- Gender: Female
- Age of Virginity Loss: 14
- Current Age: 17
- How would you categorize your story?: Regret
- Country: United States