The Humiliating Night When a 58 Year Old Woman Tricked My 20 Year Old Self Into Sex

It’s Still The Only Time I’ve Had a Black Woman

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Photo by Bill Hamway on Unsplash

As the annoying sun beamed into my bedroom window, I tossed the pale blow up doll into my closet in extreme frustration.

It was as deflated as I was, because I tried to erase the disgusting memory of that — old ass lady from the night before!

8 Hours Earlier…

I was talking so much shit to girl after girl on the telephone chat line. This was May 1997, years before I had ever been on this weird new thing called the Internet. Here I was, just a 20-year old ball of insatiable horniness looking for some action.

Yes, I had a girlfriend, a pale redhead that did all the nasty shit that I liked. But I had lost my virginity just 10 months earlier and I was still trying to make up for lost time.

And lost pussy!

Looking For Some Strange — Over The Phone

The broads on the chat line were always a chance to put another notch on my youthful belt of conquests. I flirted and they flirted back, or ignored my messages.

All of a sudden, a slow talking woman left me a message referring to herself as a “sweet black woman” and said she was “looking to have some fun.”

We began chatting and she told me that was 35 years old. That shit got me excited as hell because it would’ve been a major score if I could close the deal with a “vet.” That’s what the homies called older women, and being a young guy like I was, gettin’ action from a woman in her mid 30’s was a badge of honor.

I flirted a lot with her, even though her voice sounded strange. I was at a point in my life where I would take what I could get. If a fish was biting, then I was gonna reel that damn thang in!

I Hooked Me a Fish For The Night

We ironed out the details. It was already past 2AM, but I was determined to go to her spot for a late night booty call. The fact that she was a black woman was also kind of fascinating, since I had fucked only three women in my life by this point, and none of them were black.

It sounds silly for a black guy to be curious about sex with a black woman, but that was and still is my reality.

Since I still lived with my mother and two younger sisters, I had access to Ma’s car. I woke her up and asked if I could use it. Good thing she was groggy, because she approved without much questioning.

By the time I pulled up to the chick’s house, it was almost 4 in the morning. She lived in a high-rise apartment in downtown Cleveland. I signed in at the front desk and headed up to the 14th floor, horny as all hell and smelling like a purebred pimp!

I Met Her Standing In Her Shower

As I had instructed her over the phone to do, she’d left the door cracked and I stepped right in. She told me that she might be in the shower and sure enough, she was. I stepped into the bathroom and pulled back the shower curtain to take a look at her.

The honest truth is, she looked like a chocolate skeleton!

She was all of about 102 pounds, dark as Batman’s car and had a weird look on her face. Her bottom lip was poking out so far it could’ve been a damn awning in another lifetime. She looked as if she’d had about 5 strokes before I showed up!

I pretended not to notice the hot mess that she was, and I told her that I was going to lay down in her bed while she finished showering.

It says a whole lot about my desperation that I decided to stay for the pussy being served shortly even though this bitch looked like a Harriet Tubman knockoff! In the back of my mind, there’s no way she was 35. But, I was too committed to the carrying out of the mission to just walk away.

Something Wasn’t Right About This Broad

As the sound of water trickles from the shower filled the room, I looked around and was caught off guard. The place reminded me so much of my own grandmother; the music on this chick’s radio was the same kind of church music that grandma listened to, there were tons of bottles of medication on her dresser that again, reminded me of my grandmother.

There was even a tricycle in the kitchen!

I decided not overthink shit, so I took off all of my clothes and laid in the middle of the mattress, because that’s all there was. It was located in the living room right in front of the window that showed incredibly majestic views of the illuminated Cleveland skyline from 14 stories up.

Now, I’m naked and ready for some snatch.

The Snapper is Served

The woman came over to where I was laying, shadowy and mysterious because of the darkness of the place. I guided her onto my ding-a-ling which was already in stiffy mode. I made it a point to slip my finger into her moist slot, just because I’m a freak and I wanted to experience her erotic scent.

Turns out, I could’ve just put my hand into Lake Erie and everything would’ve been the same! And yet, I still guided her down on my teeny fishing rod and thrust into her with extreme satisfaction.

The whole sordid encounter lasted just long enough for her to grunt and moan like a wounded Moose and for me to unleash a generous dose of “baby formula” into her moist slot machine. I felt accomplished because she was yet another conquest, but I also felt disgusting because she was about as attractive and enticing as Hugh Hefner’s testicles on his last day.

And that’s with all due respect to Hef’s testicles.

The Mystery is Solved

It took just a handful of moments for me to start thinking about my exit strategy. And to ask some damn questions.

Now that the deed was done and my self respect was in the toilet, she was quick to be forthcoming.

  • Why did she have church music playing?
  • Why was there a goddamn tricycle in her kitchen?
  • Why was there so much medication on her dresser?

Those questions were all answered when she told me that her husband had died “20 years ago.”

“But, you’re 35,” I said to her with my eyebrows bent down. “Are you saying your husband died when you were 15?”

Bombshell time. Her response? “Honey, I’m 58.”

Getting the Hell Away From That Relic

I couldn’t get out of that old ass bitches’ apartment fast enough. I told her that I had to get something from the car after she told me that she was a fucking senior citizen! I grabbed my clothes and everything that I had with me, which made her suspicious that I might not be coming back.

No shit.

I couldn’t believe that I actually nailed what amounted to a living mummy. When you’re just 20 years old, a bitch being 58 and on ya’ dick naked is one of the yuckiest things ever! Driving through the streets of downtown Cleveland in glow of the late spring sunrise, I was trying to clear my head.

It didn’t help that I still smelled like her nasty cooter! I never understood how it could reek so terribly when she was coming from inside the shower! I needed something to distract me from what just took place and I found it.

The Porn Store To The Rescue

I drove to the near westside and strolled into a porn store because in that moment, it felt like a damn great idea. I spotted a box with a blowup doll inside, and I decided to check this broad out.

When I looked at the picture of what the doll was supposed to look like, I was happy as hell and started smiling. She looked like Mariah Carey, and I could picture me fucking this hot little chick. I decided to buy “her.”

The store manager was nice enough to give me a small air pump for free since I bought the doll. I couldn’t wait to get her back home to push the memories of the million year old lady out of my mind.

Ready For Some Fun With My — Doll

When I got back home, everyone seemed to still be asleep which was perfect. I stepped into my bedroom and closed the door, excited for what I thought was going to be amazing as hell.

When I pulled the blow up doll out of the box, I was shocked to see how flimsy “she” was! “She” felt like an inflatable tugboat and “her” hair was just printed on! “Her” face looked so bizarre, nothing like the photo on the box. This may seem like comedy now, but in that moment, I was really upset and I felt like I wasted my money.

When I tried to use the air pump to inflate the “girl,” the air pump itself broke immediately after I took it out of the box. This forced me to have to blow the bitch up with my mouth. Once I did, I was out of breath and pissed the hell off! She looked so unappealing and artificial.

Yes, I understood that “she” was just a doll. But I didn’t expect the box photo to be so misleading! Even still, I continued to try to make the best of the bullshit. Once inflated, I put my finger in what was supposed to be “her” snatch, but it was so hollow that my finger went completely through and out of “her” ass.

I couldn’t get tuned on for shit. After a few minutes of this nonsense, I yanked open the air seal to deflate “her” and I tossed “her” into my closet. I was genuinely pissed.

As I laid in my bed, I decided to call my redheaded girlfriend to talk. It’s funny to think about it now, but I could’ve just gotten some action from her later that day instead of nailing a decrepit bitch and trying to nail a blow up doll. I guess the real lesson in that 23-year old story is simple:

Sometimes, cheating just isn’t worth it!


The most hilarious aspect of that humiliating night with that old biddy is what my uncle said about it. When I told him the story days after it happened, he asked me the name of the high-rise complex in which the woman lived.

“Bohn Tower,” I told him.

“Bohn Tower,” he asked with a knowing look. “You know that’s an old folk’s home, don’t you?”

My eyes widened. “Um…NO!”

Ain’t that a bitch?

Personal Development Writer | Deante Unlimited podcast, Host | Deante: Under Construction web series, Star | Deante Young Enterprises, Chief Creative Architect

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