Doing Daisy

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Status: In Progress  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

I decided the easiest way to start posting is to tell how I became interested and almost obsessed with anal sex. I hope the content does not offend anyone.

When I met my girlfriend for the first time, she was a waitress at a local restaurant that I frequent. I had playfully flirted with her, as well as two other waitresses because they were cute and flirted back. I understand that waitresses get hit on all the time and it must be annoying, so I have never asked any of them for a date. I respect them as working women who don’t deserve to be pestered by horny customers.

One evening, when she gave me my check, Daisy sat down in the booth opposite me.

“You come in here a lot, but you’re never with anyone.” She said.

“I’m single and I like the food, the atmosphere and the servers.”

“That’s obvious; you tip very well. You’re a welcome customer, actually our favorite.”

“That’s good to know. Ellen, Brenda, and you are the best waitresses in town; you make having a meal very enjoyable. I like just watching you.”

(Ellen is a petite red head, in her twenties, who has been engaged to her boyfriend for 3 years. Brenda is a brunette, single, also in her twenties, pretty and average in size. Daisy is very petite, a Latina, dark hair and eyes, in her thirties, with a little extra pounds in just the right places.)

“You flirt but you haven’t asked any of us for a date. Why is that?”

“I don’t want to be disrespectful.”

“But I see you looking at my ass when I’m near your table.”

“How could you see me looking at you?”

“See those mirrors on the walls?”

“Ah! You caught me.”

“So, you’re an “ass” man?”

“I will not deny that pretty legs and a sexy ass get my attention very quickly,” I admitted.

“So, would you like to take me out Thursday night; it’s my night off?”

“I would love that.”

She wrote her phone number on my receipt. I called her Thursday, and we went out to dinner. She was charming, fun and we had a great conversation. We had lunch together on her next day off and she invited me to her apartment that evening. She offered to make dinner for us and suggested that if I complimented her cooking enough, she might ask me to spend the night.

Her boldness surprised and intrigued me. The roast beef was a little dry but palatable. The sides of baked potato and broccoli were better. I used every positive adjective I could think of for compliments, and she laughed at my efforts.

“You must really be horny; would you like to borrow my Thesaurus?”

After dinner we cuddled on her couch. Things progressed quicker than I had even hoped. Her kisses were soft and passionate, with just enough pressure to tease. We slowly undressed each other, and she welcomed my hands and my mouth as more of her was exposed. Her skin was soft, and I detected a slight fragrance, perhaps body lotion of some kind. It was mesmerizing. I wanted to kiss every inch of her. Her breasts were not large, but her nipples were small and hard by the time I tasted them. Her breathing told me that I had permission to enjoy myself with her body, and I did.

We both enjoyed the process of getting rid of our clothes, and it made it easier for each of us to explore. We struggled to kiss as her hand grasped and tugged at my hardness, and mine pressed and probed into her wetness. Our kissing became so passionate that we seemed to do it without breathing, just gasping into each other’s mouth.

“How do you like it?” she managed to ask between kisses.

“Slow and all night,” I answered.

“I mean, would you like me to suck you off? Because if I suck on it, I won’t stop.”

“That wouldn’t do much for you, now would it?”

“You could eat me afterwards; I really love that, getting it for a long time.”

“Is that what you want?” I asked as I licked a nipple. My fingers teased her entrance.

“Maybe the next time. Tonight, I’d like to feel you inside me, deep inside me.”

“Okay, but I didn’t expect to be intimate tonight; I didn’t bring a condom.”

“Then we’ll have to do something else,” she said, still fisting my erection.

“So, no glove, no love?” I asked with a laugh.

“I like sucking a cock, but I don’t want to risk getting pregnant. But there is something I enjoy just as much if you are into such a thing.”

“You seem to be keeping me hard for a reason, so just tell me what you want.”

She turned over onto her stomach. “Kiss my neck and all the way down my back.”

I positioned myself between her legs and bent over her frame. I leaned over her, kissed the nape of her neck, then worked my way down between her shoulder blades and along her spine. I stopped when I reached her hips.

She turned her head to look back at me. “Don’t stop; kiss all the way down.”

As I leaned down and kissed the apex of her buttocks. She reached both hands back and spread them open. Then I realized what she really wanted to do. I kissed along the inside of her dark crevice, and she raised her hips, lifting slightly off the couch. I kissed her crack from one end to the other and paused with my lips hovering and my warm breath on her tight brown hole.

I could hear her breathing heavily in anticipation. “Oh, God, do it, please…” she whispered.

I pressed my lips against her and kissed where she wanted. Her hands released her grip, and her buttocks gently cupped my face. She lifted her hips further, pressing against my face. I felt her hand slip underneath to pleasure herself.

I knew my station. I knew what she needed and what I needed to do. I began licking, slowly at first and then making wet sucking sounds against her flesh. She went wild under me, wiggling, moaning in a passionate frenzy. I could hear the sounds of her fingers at work.

Her voice was a constant moan, “Eat it! Eat it and then fuck it!” she wailed.

This was new territory for me, but I was drawn into it by her excitement. I pressed the tip of my tongue against her anus and pushed it in. There was resistance and an odd acceptance and my erection throbbed unexpectedly. I imitated what my cock would do, and she moaned approval.

“Yes! Fuck yes! Eat it! Please DON’T STOP!”

I accommodated her until my tongue was tired and I pulled back, catching my breath. She got on her knees, and I unsteadily stood up on the couch. Entry was slow even though she was emotionally charged up. This was my first time taking a girl anally and I was unprepared for it. Even though penetration to the max came quickly, so did I. The tightness amazed me and as I held onto her hips for support, I prematurely gave her my full load.

She squealed as I released into her. “I love it – I’m coming!”

For whatever reason, I stayed inside her until she put her hands out by her shoulders and flopped onto the couch. My deflating member eased out of her as I stood there panting but satisfied. It didn’t go as I had fantasized, but it was nevertheless memorable.

I went to the bathroom to clean up and when I returned, she was lounging on her side. I sat down next to her. “I’m sorry. I’ve not done that before, and it got to me too quickly.”

“That’s all right,” she said, “if you date me a few times you’ll get lots more practice.”

In the weeks following our first date, I learned a lot from Daisy about anal sex.




Submitted: April 23, 2023

© Copyright 2023 Grogu269. All rights reserved.

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Add Your Comments:



Very exciting! I enjoyed this story.

Sun, April 23rd, 2023 9:20pm


Thanks for checking it out and your comment!

Sun, April 23rd, 2023 3:01pm


Delightfully candid and deliciously pleasurable storytelling.

Sun, April 23rd, 2023 9:49pm


From you that's a terrific compliment; thank you!

Sun, April 23rd, 2023 3:01pm


Great job for your first post. Well written and good detail. Thanks for sharing.

Mon, April 24th, 2023 3:32am


Thanks for reading and your encouragement!

Mon, April 24th, 2023 5:06am

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