[M/F] First time without a condom, with virgin GF (Me, 27 her 25) (ALMOST a TIFU)

First time poster. On here, on reddit, all of that. I’ve been lurking long enough to probably get this right though. If you want to skip the brief backstory, just go to the * * * below.

It’s long, I know, so if you wanna know if it’s up your ally the TL;DR is get carried away, no condom, almost knock her up.

So this is about my ex, Casandra. She was a virgin (until me).
I didn’t believe it at first but when she and I started messing around it became very clear she had no idea what the fuck she was doing. It was cute and hot at the same time, in an endearing way. I delighted in corrupting her and watching her discover her body and mine. So being a virgin she was totally unprotected and we always used a condom. She had literally never touched bc of any kind before. It was the most condoms I’ve ever used actually, I always dated girls on the pill or shot.
But she refused to go on it, and it didn’t bother me. However, being all natural she had a very regular and normal cycle. When she ovulated even I could tell, even when she was fully clothed. It was murder not being able to have her raw, having gone almost 90% of my sex life prior without condoms. This is the first time she and I ever didn’t use one.
She was tall, 6’1, even taller than me (5’11) and 100% Italian. Darker skin, long brunette hair and an amazing body. What you’d expect from a Mediterranean lady. Perky medium sized tits, long legs of course.
* * *
So when she and I started actually having sex, we fell into a rhythm. The quick of it is we’d make out, touch each other, clothes would come off, more touching (I could literally feel her get wetter when she touched me) and we’d pause for a sec, I’d put on a condom, and away we went.
So it’s a hot summer afternoon and we’re home alone in her room. We’re making out, and it starts getting passionate. The clothes start coming off, and she’s soaking wet. I knew she had to be close to ovulating or she actually was at that time. When she was she would get unbelievably wet. One time I watched it pour – not squirt or drip, but pour out of her.
So I get this wild idea in my head. Now I’m paranoid and very safe when it comes to pregnancy, but she was even more so being so new to everything. But because I love what I cant or shouldn’t have and I got off on corrupting her, I was dying to know what she felt like raw. So instead of stopping to put a condom on I decided to see if she was as caught up in the moment as I was, and would just let me have her. Now initially I didn’t actually plan on going through with it; I just wanted to see if she’d let me, cause the idea of it is hot. So, we’re both naked and I’m fingering her, and she’s pouring out into my hands not squirting just soaked, and she’s jerking me off. She says are you ready for me? I say yes and I roll over on top of her, between her legs. She looks at me funny and says aren’t you going to put a condom on?
I reply “don’t you want to know what it feels like?”
She said “isn’t that risky?”
I said “What if it was just for a second, I won’t cum inside you. I just have to know what you feel like.”
To my great surprise, she says with a slightly anxious and worried look on her face, “Okay just for a second and go slow.”
My heart is now in my throat. I expected her to say no completely outright. For a second, I toss all caution to the wind and position myself at her entrance. I lean back on my knees and look at her, my dick in my hand. She’s on her back, legs spread wide open, her pink pussy lips glistening with her wetness is a stark contrast against her tan skin. Her lips are parted slightly, and she looks scared and nervous but her eyes still have that wild ravenous hungry I-want-you-so-fucking-bad look in them. She slides her hand down her tummy and spreads her pussy wider, and I point my dick at her entrance. I’m throbbing hard, a tiny bit of precum dripping out of my tip. I’m literally 2cm from her pussy, so close I can feel the heat coming off her.
Logic takes hold and I tell her no I can’t, it’s too risky. I climb off the bed and go to my bookbag where I know I stashed a few condoms. I’m so turned on I literally cannot get it on fast enough however before I can even unzip the pouch, something I never expected to happen, happens.
She grabs my arm and says “Waaaiiiittttttt! Don’t you want to know what it feels like?”
That was all I needed to push the last bit of logic out of my head. I don’t say a word, I just climb back onto the bed with her and lay her back. She spreads her pussy like before. This time I push my tip against her entrance. The tip glides in effortlessly. With my tip inside, I don’t have to worry about aim anymore and I lay down on top of her. She lets go of her pussy and her lips delicately wrap around my shaft just below my head. I wrap my arms around her and look her deep in the eyes and I begin to push. I go the slowest I’ve ever gone in my life. We’re both panting and the looks on our faces are both total shock and pleasure. Her because she’s never felt it before and me because it’s been so long that I haven’t used a condom that I had forgotten how amazing it feels. She’s soaked enough that I could have gone in in one stroke, but I go in a quarter and come out. Go in a half and come out. Go in a little more and come out, letting her lips wipe her wetness all over me inch by inch. Our breathing both catches randomly from how good it feels. At last I go all the way in and I just stay there, and I wrap my arms around her and melt into her. I let out a long relaxed sigh and she lets out the slowest loudest sexiest moan I’ve ever heard. “Wow this feels incredible! so much better than with a condom” she says. She always did state the obvious. It was cute. I’m approaching orgasm just staying still inside her but she doesn’t know this, so she starts rocking her hips. I can feel her pussy lips squish against the base of my dick, and then kiss my hips with a wet shlick noise each time she rocks back. It’s driving me wild. I’m trying to hold still and calm down but she isn’t letting me. I’m suddenly reminded on the brink of orgasm that she’s probably fertile, not protected, and my naked dick is about to pump cum into her without anything to stop it. I barely manage to gasp out a “Casandra stop, wait that feels too good” but it’s too late; I’m over the edge. I almost violently shove back and pull out, just in time. My tip is an inch out of her when the first ribbon of cum shoots out and lands trailing from her clit down to her entrance. The rest of my load ends up on her still spread pussy and stomach. We both kind of freak out after this, and we get plan B. She never did get pregnant, but we counted down the days until we were sure. In retrospect it was one of the hottest times of my life.

Source: reddit.com/r/gonewildstories/comments/4cocrf/mf_first_time_without_a_condom_with_virgin_gf_me