All Anal Sex Stories


Anal Stories:
All Anal Stories:
Bar Pickup

Sweet Memories

In the Car

The Thought of It

Senior Year

Me Talk Pretty Someday

Adventurous Woman


DP for Me

First Time's the Charm

Cocktail After-Party


Sweet Memories

The first time I had anal sex with a girl is one of my favorite memories.  I still fantasize about it.  I was renting a cabin at the time near a school overseas where I was a teacher.  My girlfriend often came for dinner, which sometimes led to us spending all Friday night fucking, and sometimes Saturday and Sunday as well.  I had suggested anal sex once, and we had tried, but I had been a little too drunk and didn't have the focus (or rigidity!) to make it happen.  But at least I'd introduced the idea.

One cloudy day we were at play on a mattress on the floor, in front of a curtained window.  (In case someone came by, there wouldn't be creaking bedsprings.  As if the moaning and shrieking weren't loud!)  As she lay on her stomach, I covered her anus with lotion and inserted the tip of one finger.  She sometimes let me play a little that way, but this time I started to press the finger in deep, like I had shown her to do to me (I love a woman's fingers up my ass).  She protested, reaching back to push my hand away.  I returned her hand to her side, and told her I was going to fuck her up the ass.  I wasn't drunk this time, and I had all the patience in the world.  I wiggled that finger in her tight little asshole while I ate her pussy from behind.  I used two fingers of one hand in her cunt while pumping that one of my other hand in and out of her backside.  More than once she moved her hand back, and I would press it back to the mattress.  That is an image that recurs in my fantasies-how she halfheartedly attempted to stop what was going to happen.  She was willing but fearful, and the gesture endeared her to me.

When she seemed ready, I pressed my cock head to that second virgin portal, her third mouth.  I was deflowering her again.  Once inside the constrictive outer ring, I stopped pressing and remained still, kissing her and whispering reassurances as I played with her breasts and pussy.  I pressed in a little deeper, then pulled back.  I pressed in again.  My penis wasn't very hard or large because the effort of penetration had worn me down.  But I managed complete intromission and was soon gently pushing in and pulling out at a faster rate.  I don't know what excited me more, the tightness of her anus or the exotic, forbidden nature of the act.  I felt so close to her, physically and emotionally.  "I'm fucking you in the ass," I said deliriously.  "This is really happening.  I am fucking you up the ass!"  I asked if she was enjoying it.

"Yes, yes," she gasped.  "It's different."  She stuck her ass up higher to meet my thrusting.

"It's incredible," I moaned.  Soon I could tell by the pitch of her cries that she was on the verge.  "Are you coming?"

"Yes, my love, yes!" 

"Then I am too!"  I fucked her harder and soon we were both crying out, as I spurted hotly up into her tight rear passage. 

"Oh, my love!  Oh, my love!" she cried.  My first ass fuck.  Her first ass fuck.  We came together, at the same moment.  For some reason I had to explain that we didn't have to worry about semen in that hole. 

I've relived that moment many times, focusing on the magic of my first ass fuck, while I masturbate to orgasm.

  1. Bar Pickup
  2. Sweet Memories
  3. In the Car
  4. The Thought of It
  5. Senior Year
  6. Me Talk Pretty Someday
  7. Adventurous Woman
  8. Footballer
  9. DP for Me
  10. First Time's the Charm
  11. Cocktail After-Party



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