Coming of Age: A Journey of Self-Discovery, Friendship, and First Love Experiences

Looking back on it, I should’ve seen it coming. When I was feeling up Gail with trembling hands in her room that day, it didn’t feel the way I did with Cassie. Of course it was exciting and made me hard as a rock, but it was… different.

An ignorant part of me still persisted: “I’m feeling up a REAL girl’s tits, this was so much better than it was with Cassie”. It wasn’t the truth of course, but I made myself believe it.

Gail and I never had sex that day. She was way too nervous to have sex, but I got the opportunity to explore an actual vagina. I’ll never forget the sweet memories I had with Gail that day. She taught me a lot: spots to pay attention to, how to finger a girl, and a ton of foreplay.

They say you never forget your first, but I still always feel like I remember a little too much detail. I remember what she was wearing as she was laying on the bed spread before me: a hot pink camisole, a white training bra (she was a particularly late bloomer) and pristine white cotton panties. I remember thinking how bizarre it was that she smelled almost… spicy.

“That… that feels good.” She breathed as I dragged my forefinger down her labia.

I won’t lie, her pussy intimidated me to no end. So many curves and folds to memorize and manipulate, I was a bit overwhelmed. Somehow, I almost preferred Cassie’s penis to this enigma. But Gail showed me endless patience. I dipped my finger into a deep valley and she tensed up.

“That’s my… my…” She trailed off in a series of moans as I finger fucked her. She gripped the sheets tightly as I inserted another finger. The texture inside was odd. I remember the inside of Cassie’s ass being almost smooth. The inside of Gail’s vagina was different: soft wrinkles and crevices that rubbed and milked my fingers. I yearned for my dick to be inside there, but Gail didn’t want to go that far, as Cassie predicted.

My briefs were perpetually sticky and getting crusty due to the fact that I’d cum so much in them. She ended up giving me a handjob, which I don’t remember as vividly as other sexual moments in my young life. And that was the entire evening in a nut shell. When things calmed down, we ended up watching some reality show on TV. I had to leave early because my underwear was beginning to chafe me.

We remained fairly close until high school. On rare occasions we would indulge in masturbating each other for about a year, but it never went beyond that. It turns out Gail was a lesbian and that’s why she never really “felt it” with me. I never felt it with her either though, so I wasn’t too put off.


-------


During my year with Gail, Cassie and I didn’t do anything. I felt a huge shift in our dynamic actually. It began to shift that very night I came home when Cassie poked her head in my room.

“Blue balls?” She grinned evilly.

“Not too bad…” I had taken a shower to get all the cum off my manhood, but not before jerking off twice. Although Gail had given me a handjob, I still needed my sack emptied a few more times.

“Did you fuck it up royally? Did she make fun of your millimeter peter?”

“Shut up.” I snapped, and then added smugly, “She jerked me off.” Somehow I felt that was a victory I could rub in her face.

Cassie seemed… disappointed? Upset? Sad? The corners of her mouth drooped and gave a slight twitch. She shifted her weight on her other leg and crossed her arms in front of her chest. I couldn’t help but notice a hard nipple poking out of her shirt before hiding it with her forearm. “Whatever floats her boat,” Cassie spat before scoffing and adding, “Or rather, what DOESN’T float her boat, I doubt she could ever be satisfied with that thing.”

I wanted to say something like “It was good enough for you” but I realized how weird and awkward that would be. Cassie and I had never really talked too openly about our sexual escapades. Not in-depth anyway. That first time she made me suck her dick was the first time we’d ever even acknowledged it. But what I found odd is that Cassie seemed sharper with her humor than usual. Sure, she could be vicious, but it still had a level of playfulness and frivolity in her voice. There was no hint of playfulness in her voice this time, it was flat and cold.

“Whatever.” I mumbled. I didn’t know what else to say, and Cassie was already halfway out the door anyway.

Everyday thereafter felt relatively normal, only like I said, the dynamic changed. Before we had roughhoused all the time, now it was only teasing verbally for the most part. Physically, things toned down a lot. Sometimes we’d push each other and give each other wet willies, but that’s pretty much as far as it went.

In retrospect, maybe because it felt like Gail and I were kinda dating, even though we weren’t. We were exclusive to each other for no particular reason and Cassie recognized that. No matter how much of a bitch Cassie was, she would never want to jeopardize any of my relationships. She cared for me, even if she had an extremely odd way of showing it.

Everything seemed to be changing. I didn’t really see too much of Cassie during that year anyway as our mom bought her a junk car for her 17th birthday in honor of her getting her permit. I was impressed – our mom must’ve scraped together for quite some time. Cassie was always out somewhere, and even managed to get a weekend job at a nearby restaurant. They also changed her hormones to injections instead of just the gel she was taking, and she injected it in her fat instead of her muscles which diminished her mood swings greatly. It turns out, her moods and tantrums were off the charts because her hormones would rise and fall so sharply. Now that they were stabilized and level (for the most part) she seemed a lot more level-headed and calm. Our encounters seemed to become more rare though, and our fights pretty much non-existent. We were growing up, becoming more mature, and realizing that it (at least for a short time) might not be a good idea to fuck each other right now.

By the time I turned 16, Cassie was 18 and nearing

Explore my other stories

THE END