I lost my virginity at the age of 16 to my first “real boyfriend.” You know the kind–you’re just getting into boys, have maybe 10 things in common with him, and think “Yes, you are here at the right time and place…perfect for the role.”
I wasn’t a delicate flower, and I worked a little backwards in terms of womanhood introductions. My sister had been begging me to use a tampon for years, saying things like, “You have no *idea* how comfortable they are.” I refused until I was fingered for the first time and realized I could shove things in me without repercussions. Before that, my vagina was a mysterious cavity in between my legs. Sometimes, I looked at it in a hand mirror as I wondered about the secrets within.
Then Dan came along, and metaphorical and literal barriers were broken.
Cut to my deflowering: My parents are away. It’s daylight. I’m straddling Dan, and I put Ludacris’ “Splash Waterfalls” on repeat in my boombox. Romantic poetry like, “Know how to mack a broad, she’s on your sack and balls, You call her Jabberjaws, what? (fuck, me!)” is floating from the speakers. I suck Dan’s big Jewish dick, using my handy Urban Decay edible marshmallow body powder on his balls. He lets out little chuckles and tells me the leopard-print powder puff is tickling him. I lick up the overpriced, sparkly dust.
Things progress. I am ready. He puts on a condom, and I waste no time impaling myself on his schlong. In hindsight, his dick was fucking huge. I am really impressed looking back at my former self. Back to the story. As I allow myself to settle, Dan tells me how great I feel, how he misses being inside a pussy (he was 17 and had sex with his ex before me). Then I start riding him. Hard. It doesn’t exactly hurt like I think it’s supposed to, but it doesn’t feel great either–more like a key that won’t fit and is forcing itself to. Dan asks if I am ok. Tells me I am riding him really fast for a virgin. I tell him, “I just want to get the pain part over with.” It doesn’t get better. He eventually cums, and I am left straddling him while wondering how much longer I have to do this until I feel good. We lay there together a bit and then Dan gets a call from Daryl. Him and Leslie are outside.
I forgot to mention this, but Dan and Daryl were attached at the hip, and Leslie was my friend (she was Daryl’s girlfriend and introduced me to Dan), so all four of us hung out wayyy more than we should have. It was pretty creepy. I even blew Dan under the covers while he laid on a sofa in Daryl’s parents’ basement. At the same time, Leslie gave Daryl a bj under the covers on the couch opposite us. It wasn’t my idea.
So, after our post-coital bliss, Dan and I went outside to say hi to our friends. Daryl insisted that Dan sit with him in his car while Leslie wanted me to talk with her on the curb. Leslie knew I was planning on having sex for the first time and must have told Daryl. I sat there spilling the details as she congratulated me on becoming a woman. The boys were in a much more intense conversation in the car and out of earshot. But I could see Dan’s reflection in the car’s side mirror, and his gestures and facial expressions indicated that he was describing something euphoric, heavenly, and enviable. I thought, “Wait, was he in the same room as me? Did we just have the same experience? Is he exaggerating for bro bragging rights?!”
Before I could finish my reflection, Daryl called me to the driver side window. I walked over timidly. With a big, stupid, half smug/half light-hearted grin he lifted up his hand to give me a high five. Then he said something along the lines of, “Congratulations. You’re a woman now. How does it feel?”
“Uhhh, fine I guess.”
“Yeah, Basmine!” (his nickname for me). More stupid banter ensued, and eventually Daryl and Dan had to drive back to their hometown about 45 minutes away. They gave Leslie a lift back to her parents’ house a couple of blocks over.
There I stood on my perfect suburban street wondering what the fuck just happened, feeling like I was in a cult with Dan, Daryl, and Lisa, and contemplating how I was “not a girl, not yet a woman” as the great Britney Spears once said.
Source: reddit.com/r/gonewildstories/comments/gf0726/the_way_i_lost_my_virginity_lighthearted_and_true