I was 16(F) and just got over something sad. I tried to hook up with a guy for the first time with no success. Me and another guy (Justin) were horny teenagers, but we were just kind of friends because we had mutual friends.
I knew Justin was sexually experienced, he was a bit of a chunky guy (god damn, that was and still is my weakness). He was a really sweet guy who I was fortunate to have been friends with. I texted him asking for weed (it was my thing when I was sad), he didn't have any, so he seemed useless. But he kept trying to reach out to me, so I did the same, harmless flirting, no big deal.
Justin knew I was trying to hook up with his friend (David), but he wasn't emotionally attached, so he didn't care.
I half-jokingly texted David asking for a threesome, he was a nervous goody two-shoes, so he wasn't ecstatic.
David texts me back, "Did you tell Justin about wanting a threesome?"
"Yeah," I replied, feeling embarrassed.
"Lol he told me 'YOU BETTER HAVE THAT THREESOME AND YOU BETTER HAVE IT FOR ME' "
I smirked and texted Justin. I don't exactly remember how, but somewhere along the line, Justin and I had gotten pretty horny while texting each other and made plans for him to take my v card at my house the next day.
He brought a bag containing lube, a box of condoms, bandanas, and two small vibrators (a cock ring and one for his finger)
Holy shit.
We got into my bedroom and he got me naked, we're both breathing heavy and going at it the way teenagers do.
He was fingering me and said, "let me know when you're about to cum, I want to try something"
About a minute in (he was damn good at this shit) I start to feel it. "Oh my god, I'm about to cum" I yelped.
He grabbed the finger vibrator from my windowsill and quite literally to the bathroom to rinse it off (rubber – covered in lint).
He comes in and I can barely hold myself together at this point. He turns the vibrator on the low point and roughly starts going in, rapid and deep. Holy shit. I'm already shouting and cumming and it hasn't even been 5 minutes in.
"I like that you cum fast", he said, coming back up to kiss me. We lay there cuddling for a few minutes for me to catch my breath, but we both know it's not over.
Next thing I know, I'm choking on his cock. He was average/small, but size doesn't matter to me, it's how you work with what you've got.
"Are you ready?" Truth is, I didn't think I would be, but at that moment I was certain. "Yes."
He grabbed the bandanas out of his bag and tied my left arm to my left leg and my right arm to my right leg. Shit, this was getting me wet. "Do you want me to gag you?" God, he was such a sweetheart, always asking what I was comfortable with.
"Yeah!" I replied, this was the best day of my life already. He took another green bandana out and put it around my head.
He grabbed a condom from the box and put it on his member. "Come here," he said in a sexy, raspy voice. I was on my back and started laughing and gesturing to my bonded limbs, so he pulled me to the edge of the bed and spread my legs for me.
He went in slowly, just like a gentleman should for his lady's first time. It felt even better than I thought, but hurt by the time he went balls deep. I moaned, but he could see I was in pain.
"Are you okay?" He looked so concerned.
"Mhmm"
"Do you want me to keep going?"
"Mhmm"
He kept going, slower to help me get used to it. Somewhere along the lines, the pain felt so fucking good, and I found myself becoming a cock-loving, moaning slut as he pounded a little harder.
"You like that?" I love when a guy asks me this. It's hot and sexy, but he really does want to check on me!
"Mmmmm!" I jerked and shook from pleasure. Fuck, this was so much better than the horror stories my friends had told me.
"Flip over." Fuck, everything about this guy was perfect, his voice, his mannerisms, and I fell more in love with his dominance than anything.
I obeyed and he pushed in, earning more moans from my gagged mouth.
He went so fast at this point, fuck it was good. He slapped my ass so hard. I yelped and I could hear my heart racing.
He grabbed my arms and pinned them on my back while he fucked harder and harder.
I'm sure the neighbors could hear me at this point.
"Can I try something?" He asked so gently.
"Mhmm!" I was open to anything, and I didn't regret it then, I don't regret it now either.
He pushed his johnson into my ass. Oh my god it felt weird. I just widened my eyes, it didn't hurt that bad actually.
"Are you okay?"
"It hurts a little bit"
"Do you want me to stop?"
"… Maybe."
He pulled out slowly. "I'll stop."
He grabbed a new condom, "don't wanna give you a yeast infection" how much more considerate could this guy get? I wish every partner was like this.
"Do you want me to choke you?" Oh my god, this shit was getting freaky.
I pulled the gag down just to say, "Fuck yeah" He grabbed my throat, and I didn't think he was squeezing hard, until I felt blood rush to my face and I couldn't hear well. Oh, fuck it was good.
And that was my first time. It was a little big awkward, sore and painful, but the excitement and pleasure made it all worth it.
Oh and he came on my face, just a few thick ropes. Not my favorite, but back then it was my thing.
Source: reddit.com/r/gonewildstories/comments/3bbu5x/my_first_time_fm_story_gets_juicy_by_the_8th
I just remembered that his mother called right when it was getting good, and he kept going, harder even. Ahh, good memories