Getting Started With All That Planning
Alright, let’s get into it. So, me and my girlfriend at the time, we’d been talking about this for weeks, right? Feeling super ready, super excited, but also absolutely terrified. Like, what if I mess it up? What if it hurts her? What if I don’t know what I’m doing?

We decided to get some condoms first. Went to the pharmacy. Felt like everyone was staring, judging. Grabbed the first box I saw, paid super quick, practically ran out. Later realized I didn’t even know what size or anything – total rookie move.
We picked a weekend. Planned it. My place, parents away. Felt like preparing for some huge mission.
The Night Before & The Day Of
Couldn’t sleep at all the night before. My brain was buzzing. Watched some terrible ‘how to’ videos online – mostly confusing, some just plain wrong. Tried reading articles, too much medical jargon, gave up.
Day of, my hands were sweaty all afternoon. She came over. We tried to watch a movie, couldn’t focus. Talked about everything but it. Ate pizza. Stomach felt weird.
Eventually, we just looked at each other and were like, “Okay, maybe now?” My heart was hammering against my ribs, honestly thought she could hear it. Kissing felt different suddenly, more intense, nerves making everything shaky.

The Actual Thing: Messy & Real
Getting the condom on? Disaster. Fumbled with the wrapper forever. Almost tore it. Tried putting it on the wrong way first – felt thick in the head. Got it flipped, finally got it on, but worried I wrecked it by touching it wrong.
Finding the entrance? Way harder than anyone makes it seem. We were lying there, trying to be sexy, but it was just us giggling awkwardly and saying “Wait, is that it?” “I don’t think so?” Used fingers a bit first, felt weird, like “Is this helping? Is this the spot?”
Finally got it in. Honestly, first thought? Wasn’t fireworks. It was more like, “Oh. Okay. This is happening now.” Kinda tight, kinda warm. Forgot to breathe for a second. Asked her constantly “You okay? This okay? Hurting?” Worried I was squashing her.
Moving? Total mystery. What is a rhythm? Felt like I was flailing. Couldn’t relax enough to actually feel much pleasure myself, was too focused on not messing up, not hurting her, not cumming instantly. Lasted maybe… a minute? Two? Felt like an eternity of awkward thrusts.
Finished? Pretty much immediately overwhelmed. Condom felt weird pulling off. Came way more than expected, kinda gross. Lay there sweaty and sticky, breathing heavy. Still worried: “Did it feel okay? Was it okay?”

Aftermath: Relief & Reality
Biggest feeling afterward? Relief. Glad the “first time” pressure was gone. It wasn’t amazing, it wasn’t magical, it wasn’t like the movies. It was clumsy, awkward, messy, and honestly, kinda stressful.
We cuddled after, which was actually the nicest part. Just talked about how weird it felt, how nervous we both were, laughed about the condom struggle.
Honest Tips? Here’s What I Wish I Knew:
- Nerves are 100% normal: Your hands might shake, you might forget how to put a condom on (practice alone!), you might blank out.
- It probably won’t feel incredible: Don’t expect fireworks. First time is often awkward and confusing physically.
- Focus on basics: Go slow. Use lube (even if she’s wet, helps so much!). Communicate constantly (“this okay?” “slower?” “that spot?”).
- Condom practice is key: Seriously, try putting one on a banana or just by yourself beforehand. Fumbling kills the vibe.
- Climax ain’t the goal: Especially for guys. Staying relaxed enough to even feel pleasure can be hard. Focus on connection, not performance.
- Aftercare matters: Cuddles, laughs, debriefing the awkwardness together? Makes the whole thing way more positive.
So yeah. My first time was far from perfect. But getting through it together? That felt real. The awkwardness fades. The connection stays. Just breathe. It gets way, way better.