18[F] tried anal for first time. he slowly inserted his finger to prep me for his dick, and that made me cum almost instantaneously.

*This happened a few months ago but posting here for the first time*

The feeling was so intense that when he finally got his whole middle finger in, i came in less than a minute. It was an orgasm like none I’d ever felt. Like maybe he was somehow massaging my vagina or g spot from my anal canal.

Next he began trying to enter with his penis. He wasn’t that big but it sure felt like it was too big. We had to use so much lube. Slowly he kept inching in and pulling back out to lather himself with more lube, and massaging some into my butthole as well. I gasped and grunted every time. What an amazing and simultaneously terrifying sensation.

I kept asking if he was all the way in because I felt so stretched, but he kept replying no. I was on all fours doggystyle and watching the action from between my legs. My pussy felt extremely sensitive and i could feel that i was gaping a bit. I was extremely wet and could feel juices flowing down my pussy and ending at my clit. I could see my own strand of grool slowly developing.

He kept trying to burrow his way into my ass and I kept making noises. At some point my eyes teared up and he stopped to ask if I was okay, but I wanted him to keep going. I refused to not take every inch of him inside me. After about 30-45 min he finally got all 5-6 inches in. He added a bit more lube and continued to pump me as i bit on my comforter and moaned into my bed. My body was shaking from the overwhelming sensations, especially my legs. It wasn’t long before he came inside my ass. He snuck out a couple hours later.

The next morning I was in the kitchen and my dad asked if I was having nightmares last night because he thought he had heard me screaming.

Source: reddit.com/r/gonewildstories/comments/m3zv41/18f_tried_anal_for_first_time_he_slowly_inserted

18 comments

  1. So you both have a new trick to get you an orgasm quickly. That’s awesome

  2. What a fantastic story and experience! Sounds like you’ve opened up another space to play!

  3. So what works for me to relax more is to play with the clit while he goes in. I’m not just focused on one or the other and it’s smoother and takes less time to get in there all the way

  4. When I go down on my wife I will rub her anus with a finger and she cums really hard and easy like this. I’ve always teased her saying her g-spot in in her butt hole

  5. use a ridiculous amount of lube. it’s fine. your butthole is not self lubricating so it needs the help. srsly sex is not like what it looks like in porn

  6. *About 35-40 mins of trying he got all 1 and a half inches in & that reminded me why we were trying anal in the first place*

  7. Buy some trainer anal plugs. You’re lucky to have a boyfriend who was more gentle and concerned about you your first time. My first time was hell, and I didn’t try it again for years. But when I did…OMG! It can be earth shattering, kind of like fucking when I’m on my period. I don’t know why it’s better then, it just is.

  8. Wow, what a lucky guy your boyfriend is. You are so hot in your pictures ;)

  9. Oh no, not dad.

    On a side note, I’m always expecting to read about the time he pulled his cock out and a ton of lube, cum and liquified shit comes flying out of that rooster tail.

    Not everytime. Just once or twice.
    When it does happen, it is a mixture of horror and so fucking funny one cannot hardly stand it.

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