[M]y [F]irst Time: The Much Older Woman

I was 21 when I met Barbara at a bar in Miami. I didn’t so much notice her as she noticed me.

She was a Canadian, in her late 50s, married, a little overweight, a lot tipsy, and seemingly one of those snow birds that Floridians despise. I learned that her husband played golf every afternoon before meeting her at the bar where they would have cocktails, and dinner. Once a week, they’d have sex.

Okay, maybe a little too much information for someone you’ve just met, but whatever floats your boat. I sometimes over-share when I’m drunk, so no biggie. 

Another drink later, her husband shows up, she throws a twenty on the bar and says goodbye. As she stands up, I check out her lips, smile, and breasts. As she walks away, I survey her nicely tanned legs, matronly ass, and graying hair. Not bad, Barbara. Not bad. 

Fast forward two weeks, and I am once more at that same bar.

“I was hoping I’d see you again.” She kissed me on the cheek. She smelled amazing. And, for the first time in my young life, I was sexually attracted to a much older woman.

“My husband is playing golf with our son, and he’s going be late. Would you like to come back to our condo for a drink?”

“Sure.” I’m wondering where this is going, but I’m 21, invincible, and would do just about anything for Barbara short of hooking up with her son or killing her husband. 

When we finally get to the condo, she kisses me. Really skillfully. Her lips are soft, she smells amazing, and I can sense a building tension between us. My hand slides down over her ass, and she responds by kissing me even more passionately. 

We are pressed together, and I know that she can feel my cock throbbing in my shorts. I slide my other hand inside her waistband, and feel her smooth flesh and her lacy panties.

I start to undo her belt.

“What are you doing?”

Um…what does it look like I’m doing?

“I’m sorry. I got a little ahead of myself.”

She said, “I don’t mind, I just want to know what you are doing.”

“I want to taste you.” 

“My husband won’t…,” her voice trailing off.

What a dipshit. 

More assertively this time. “I want to eat your pussy.”

She stepped back and loosened her belt and unbuttoned her shorts, letting them slide to the floor.

White, lacy panties, distinct tan lines, and a rather generous bush escaping on either side of the fabric. 

I guided her to the nearest barstool and she sat. She was not particularly toned, but she was on fire.

I dropped to my knees and parted her legs enough to get my face between them. I dragged my tongue up the inside of one thigh and down the inside of another. I could smell her sex, and she moaned softly as my tongue pressed against the crotch of her panties. 

She was getting wetter by the moment, and I finally peeled away those lovely panties before slipping my fingers inside of her. She wasn’t particularly tight, and she smelled musky; but, I was enjoying her body’s response to my touch. When I flicked her clit, her knees buckled, and when I slid my tongue along her engorged lips, she moaned a little more loudly.

My tongue dipped inside of her, and my fingers followed as I licked, flicked, nibbled, and sucked her 58-year-old cunt until she grabbed a handful of my hair and clamped her thighs against my head.

If there was any doubt about what was happening, it was removed when she grunted, “I’m cumming!”

And cum she did, shaking and shuddering as her pussy gripped my fingers like some maniacal sex machine. 

“Don’t. Stop!”

I couldn’t really do anything except keep going since she had my head in a death grip.

I slaked my thirst with her juices, nibbling and sucking her clit. She came again.

Finally, exhausted, she released me.

“I don’t think that I’ve ever cum just from oral.”

She looked at me, my messy hair, and the growing wetness on my shorts.

“Oh! I’m so sorry.”

She pulled on her panties and shorts, fastened her belt, and guided me to the spot where she had been sitting just minutes before.

She unzipped my shorts, and fumbled with my cock. Upon freeing me from my boxer shorts, she touched my head with the tip of her tongue. Then, she swallowed me whole, gagging on my length, before she started working my cock with her mouth and her hands.

I wanted to grab her by the hair; but, at the same time, I didn’t want to mess up her coiffure. 

She continued sucking and stroking, sharing with me her many years of experience. 

Before I could say anything, she picked up the pace, looking up at me, and saying, “Mum mn my mouf.”

Oh! She wants me to cum in her mouth. 

And with that, I did.

I emptied my 21-year-old balls down her greedy throat. She kept up with the flood, sucking everything out of me.

When I had finished, she opened her mouth and showed me what remained. She smiled, swallowed, and opened her empty mouth once more, proud of her efforts. 

Then, she looked at her gold Rolex and said, “Look at the time.”

I washed my face while she fixed her makeup and brushed her teeth.

An untucked shirt covered the cum spot on my shorts, and we returned to the bar just ahead of her son and husband.

After meeting them, and saying our farewells, they went off for supper, and I stayed for another drink.

This would become a somewhat regular thing over the next five months, at least once a week, and sometimes involving more than just oral sex.*

*But never her husband. 

Source: reddit.com/r/gonewildstories/comments/103eooa/my_first_time_the_much_older_woman