A few months into my first job after college graduation, I was on a trip for work with some colleagues that had me traveling to a new city for the first time.
I love going out to explore, so my coworkers and I went out to a seemingly popular bar with a pretty big dance floor.
That’s where I spotted Cathy–a much older (I was 21) woman who I found incredibly attractive. She had a tan, petite body–thin, toned arms stood out to be in the black low cut top she wore that also shopped just a tad of her midriff (tight, low-cut jeans also enabled this). She had long, fake blond hair, larger-than-you’d-expect breasts and a pretty smile. She was wearing heels, but was still quite short.
I learned, even before then, a huge secret of bars/clubs: The gorgeous girl/woman dancing without a man in the middle of the dancefloor? She actually *appreciates* a man approaching her. At least in most cases.
Why? Because it takes balls to approach her. And most guys won’t do it. If she turns you down, *everyone* can see it. But it’s a huge opportunity, if you believe in yourself.
She was there with a friend, but smiled as I approached her. We chatted as we danced. She was 42, recently divorced, mother of three. There was lots of non-sexual, yet meaningful physical contact: Her hand on my shoulder as she leaned in to speak toward my ear; my hand gently on the small of her back as I listened to her. All little signs of our compatibility.
She felt safe with me.
Before long, we were dancing a bit more provocatively. She wasn’t supremely talented, but it didn’t matter. She grinded her tight little ass against my cock as her friend flashed the “OMG” look at her. My colleagues were a bit surprised. And probably jealous. I didn’t mind the attention.
If she had a problem with my age, she certainly wasn’t showing it. Part of me thinks she liked the novelty of it. She found it flattering.
She eventually had to leave, but I got her number and we texted much of that night and the entire next day. Flirting *hard*. I was a little surprised (pleasantly) at her forwardness. She said she felt the size of my cock through my pants and wanted to see it in person.
I had a hotel room downtown, and invited her to come by the following night. After my day in meetings, I rushed back to my hotel room as quickly as I could, ate a few granola bars from the front desk, and did a quick in-room workout to get my blood flowing and muscles tight. She had to be home by 9pm because of the babysitter, so she was set to arrive at 6.
She came directly to my room and I greeted her with a hug–my hand by her waist, where I could feel the thong she whore under her little black dress. She wore some sort of wedge heel and smelled like vanilla.
I could tell she was nervous. For all her talk over text, this was showtime. After I greeted her, she reached into her bag to pull out a bottle of white wine, and two thick crystal glasses from her house.
“I want to show you that I know how to take care of a man.”
“I like it,” I told her, but the truth was the wine was cheap and the glasses were tacky. It was screw top bottle, so she opened it and poured us too glasses. I mostly saw it as a signal of her desire to please. And how she’d be comfortable following my lead.
We sat on the bed and sipped wine, with SportsCenter on the TV (admittedly, not my finest stroke of romantic instinct). As we sipped wine, I had my hand on her left leg, gently stroking it, trying to diffuse her nervousness. She had told me via text she had only been divorced for a month, and hadn’t gone on a single date.
And here she was, bringing wine to a hotel room for a man half her age.
My hand wandered more toward her pussy, and she quietly spread her legs slightly to give me access. We chatted, but the conversation was difficult to focus on, as I pressed through the thin fabric of her dress to gently grind a seam from her panties against her clit.
She moaned softly and said she needed to use the bathroom. She got up, spent a minute or two, and walked out, looking a little more relaxed. I stood up to greet her, and she wrapped her arms around me as I scooped her up by the ass. Like her arms, her legs were toned, but not overly muscular. More a “fit mom who watches her weight” than a Crossfit queen. We began making out, and I placed her on the bed to lift her dress up and off her dress.
Her lingerie was *gorgeous*. Lacy. Black. Perfectly fitting. I can’t imagine when she possible could have last worn it. Her wedding night?
She could tell I was impressed, and that emboldened her. She turned and did a little strip tease for me, bending over in front of me as I lay on the bed. I playfully slapped her ass and leaned forward to undo her bra.
I pulled off my shirt and slid off my jeans. She was on all fours in front of me, wiggling her ass. Like a “What are you gonna do about it??” taunt.
I leaned toward her on one knee and pulled her thong to the side. Her pussy looked raw and tender. Very red, like she shaved it with a razor for the first time in years just before coming to the hotel. I wanted to affirm her. I was probably the only the second man to see her pussy sine the Clinton administration.
“Your fucking pussy looks delicious,” I told her, as I rubbed her clit from behind. Her sweet folds were already quite wet, and I slipped a few fingers into her with a “come here” motion, digging down deep into her.
“Fuck, Daddy…”
And that was the first time *any* woman called me Daddy. And she was twice my age.
Then I took my cock out.
I knew she was intrigued by my size, so I wanted to tease her a bit. I was behind her like I could mount her, but instead, I let my cock flop against the top of her ass/the very low end of her back. The top of her ass cheek provided a nice little resting space for the base of my shaft, while my balls hung low into her wetness.
It was a hot visual, and I felt bad she couldn’t appreciate it. My pre-cum was starting to ooze slightly, so I took my cock and pressed it into her ass cheeks, smearing my seed against her soft flesh. Taunting her as I rubbed her clit.
I had condoms, and was expecting to use one, when she suddenly shifted her weight back onto her heels, turning her upper body a bit and reached back to grab a hold of my cock.
With my hand still holding her thong to the side, she gently rubbed the head of my cock all around her wanton folds. Using my cock like a toy of sorts.
There’s something fun when a woman gets to enjoy a big cock for the first time; even moreso, when she’s been married to one man for such a long time. Not only was my cock a novelty to her, but *everything* I did was different. She’d been used to one way of being kissed. Touched. Rubbed. Controlled (or lackthereof).
This was *all* ne for her. Younger man. Big cock. Hotel room wine.
She continued to lubricate the head of my cock as I gripped her shoulder.
“AhhhhhHHHHHHHHHHHH,” she cried out quite loudly as she backed up around my shaft. She got about half way before falling forward, clenching her ass, exhaling a big breath and having to start all over again.
This time, when she was backing into me, and I thrusting into her, I told her that her pussy was *all* mine.
“Yesss. Yes it is!” She said with conviction, grunting as she rode me until my entire shaft was surrounded by her wetness. I gently slapped her ass. Cosmetic spanks. I didn’t think she could handle more.
Her breasts were flopping beneath her. She had a steady, low moan the entire time. Like the hum of a vibrator. Except it was her pussy. No toy. “Uhhhhhhhhhmmmmm” she steadily groaned, in between gasps for air.
I grabbed Cathy’s hair and gently pulled her head backward, toward me. I saw her face in the mirror and it was one of the sexiest sights I’ve ever witness: A woman’s first new dick in decades–and a thick, young one that was absolutely punishing her surprisingly tight hole.
As she began to cum, I used both hands to grip her shoulders. Her thong shifted back against my cock, and it was a tad unpleasant. She trembled and shouted incoherent yelps and moans.
It wasn’t long before *I* was ready. I told her I was going to cum.
“This pussy’s too good. Too fucking good. I’m going to cum deep in your fucking pussy.”
I figured if she wanted me to pull out, she’d have said so. My words gave her a burst of energy. As best she could, she clamped her lips around me and slapped her ass against my hips.
“Fuck me Michael. Fuck this pussy, Daddy.”
I moaned loudly a I erupted, blasting ropes of thick, gooey seed deep inside her little MILF pussy. It felt so good. Her pussy was so smooth. So wet. So *eager*.
It was almost if fucking her brains out transported her back in time. For a few hours at least, she wasn’t a divorced, responsibility-laden 40-something.
She was like a cock-hungry co-ed, wanting nothing more than to hop on a cock and call her partner *Daddy* as her pussy was drilled.
And so she did.
When I slowly pulled out, my cock was covered in her cream. Her pussy gaped a bit, wanting to be filled again.
She giggled and thanked me. She flipped on her back and seconds later, giggled as my seed tickled her pussy as my seed leaked out.
She kept her panties on to collect everything.
Source: reddit.com/r/gonewildstories/comments/j1qem5/in_which_a_woman_twice_my_age_from_the_bar_took
Lucky guy.. nice MILF
Hot!
Older women are fun ?☺️
Sounds like she really needed that creampie. Congrats on taking such good care if her. Blowing loads deep into fit needy MILFs must be such a rush.
Hope she took that load home with her