Happened in HS for me with a very shy busty white girl. I had fucked a few girls already having discovered thanks to the internet I was well hung. The women I had slept with in the passed and my tape measure at home had inflated my ego to epic proportions and I was primed for some deflating. 

This girl was different from the previous girls in a few major ways. First she didn't want me to eat her or finger her. Infact she told me straight up all she wanted was dick in vagina sex and had heard from a friend my cock was nice. She didn't even want kissing at first but changed her mind right before. This meant no hand jobs no blow jobs no tit fucking no excuse to not last.

The second way she was different was so obvious i should have seen them coming. The girls. The twins. Her big creamy white milky soft warm inviting udders. She never wore anything other then big baggy t-shirts and hoodies we lived in the Midwest everybody has a jacket on!  

I've had sex with such busty curvy girls like her since but she was my first. They were as new for her as for me. This was obvious from her poor fitting o overflowing bra and the fact that her huge DDs had never meet gravity yet. They wobbled and swayed out of her bra. She seemed just as awed by them as I was. 

We were both naked and she wanted to be on top for her first cock. She was sitting in my lap looking down at my cock and she looked terrified. Her trembling only made her breasts shake more and her small hands twitching on my huge meat made me want to just rrrruin her. 

She tried to lower herself on me and OUTCH did not enter. Her pussy had closed up and dried out tight this was when she decided maybe we needed some kissing. After making out and whispering sweet nothings in her ear we tried again. This time I get in some what the tip. However it wasn't much and kinda hurt to be honest. It was however teasing the fuck outta me and I was aching. The idea of ruining her kept going through my head but I didn't want to scare her so I restained myself. This drove me crazy.

In the third try I felt something change. Her pussy "relaxed" she whimpered at me and mewed like a cute lil kitten and the aggression I had felt melted away. As she lowered herself down more I gave out a long involuntary moan. Her titties lowered right onto my mouth I could suck them and watch her face as I entered her pussy. 

It felt so right my eyes half closed as I whimpered face buried in soft warm overflowing tit flesh. I gasped as I felt her bottom out on my cock. She look down and her attitude had changed. She didn't seem shy anymore infact she seemed to have almost a swagger about her now a glow. She put her hands on the back of my head and just smoothed me in her tits.

I tried to warn her to say something. It had been maybe 5 seconds since I had touched her cervix with the head of my cock. But her tits her warm tits had me. She owned me. She didn't even know it. I almost cried as I felt it happen I knew exactly what it was. A premature orgasm. A betagasm. 

It didn't even matter tht at the same time my big fat alpha cock was stretching her. It was still humiliating. My face burned and I squirmed hidding in her tits. Mewing like a bitch as more cum flowed out of me. But I felt her hands petting the back of my head. She was looking down at me smirking and glowing.   

She said "look at you? Having fun?" And giggled. She had loved it. She was proud of herself. I couldn't believe it she didn't mock me or anything. She just let me play with her breasts and petted me kissing my head as I went limp in her. We chatted for awhile all while my cock was still soft but inside her. For awhile it was as if we were just having a casual chat. Howvere my gaze dropped back to those tits.

She stopped talked mid sentence and gave me this questioning look as I started to grow in her. Those udders. Words cannot describe. She gave out a little gasp as my cock lurched inside her thicker. I remember her smirk disappearing. This puzzled look on her face. I got longer and harder stretching her slowly. She was panting as I touched her cervix again. And as I flexed my fully hard 8 inches in her she gave out a cry of lewd pleasure her pussy juices flowing out of her now. 

There was no premature accident to save her lil pussy the second time. I fucked her till she tapped out. I made her orgasm so much I wanted to whoship her body. I felt she deserved each orgasm and I owed it to her to give her them all. We still talk even now years later and every now and then I'll get a text that make me cream my pants from her that reads "how's the premature dick?"