Robbing the Graveyard

By Kendra Holliday | August 27, 2017

This happened in 2009…I learned some very valuable lessons – the hard way. 🙁

By Rama (Own work) [CeCILL ( or CC BY-SA 2.0 fr (], via Wikimedia Commons

I have to admit, I get a kick out of the fact that my partner Matthew is three years younger than me. Still, I have a thing for old men – as long as they have good hygiene and don’t wear old man cologne!

I told Matthew I was flirting with a 76 yr old fellow, and he commented wryly, “There you go, robbing the graveyard.”

Of course that prompted me to take it up a notch, so I found a cute 92 yr old man and sweetly charmed him. He asked me out on a date, and I accepted.

Leonard was born in 1916. Last year he lost his dear wife of 60 years. It’s not the first time I’ve dated a widower.

He’s legally blind, has a hearing aid, and uses a cane. Of course I drove.

I passed a couple people in motorized carts as I walked down the senior living center hallway. I knocked on his door wearing a pretty dress, and he answered wearing a summer suit and tie. I LOVE when a man dresses up for a date. It shows respect.

I asked, “Where’s your cane?”

He dismissed it gruffly with the wave of his hand. “I’m not taking it!”

It was a good excuse for us to hold hands. We were holding hands as we walked into the restaurant. I wonder if people thought I was his granddaughter.

He told me sweetly, “It is a real honor to be on a date with the likes of you. I feel real proud.”

I said coyly, “Is that a snap button shirt, Leonard?”

He said, “Why, yes it is. I find them easy to get on and off.”

I clapped my hands. “I LOVE snap button shirts! Can I unsnap it tonight?”

That cracked him UP. He blushed and said sure.

After dinner we went back to his place. I’ve never partied in a retirement community, so that was a new experience for me.

He wanted to get more comfortable, so I loosened his tie and threw open his shirt, which he took off, leaving him in an undershirt. He made us cocktails. He’s a vodka man.

He put on an “In the Mood with Glenn Miller” cassette tape, and we danced cheek to cheek in his living room. He’s a WAY better dancer than me. Pretty much everyone is.

After a while I suggested, “Why don’t you sit for a spell?”

He said earnestly, “But then I’ll have to let go of you.”

I told him he could sit and I would kneel at his feet, so we did that.

We held hands and I stroked his face, arms.

He said solemnly, “I’m going to make love to you.”

I said, “I would like that, but not tonight. I want to make sure we aren’t rushing into anything. This is an unusual situation.”

He accepted that, and said, “I suppose I should prepare for it.”

“What do you mean?” I asked.

“Get some condoms.”

I giggled, “Oh my gosh Leonard, can you imagine if you made a baby at your age?!?!”

He laughed too, and I told him, “I can bring condoms.”

He seemed surprised. “YOU have condoms?”

I said, “Hey, I’m a modern girl!”

Then he said, “Well I have only been with my wife the past 60 years, I was true to her. I did have the clap once, but that was in 1941. They didn’t have penicillin then, so they had to inject this red stuff right into my privates to cure it.”

Since we were talking all personal, (he acted pretty shocked to learn that I had a vibrator – NO I didn’t tell him I had one in every shape and color) I asked him some more questions. He told me his wife was the kind who was very good to a man, and how she used to twitch her pussy on his dick and give him shivers up his spine.

I asked him, “When was the last time you were kissed down there?” I was having a hard time asking a man of his age, “When was your last blowjob?”

He told me HE HAS NEVER HAD A BLOWJOB. Can you imagine living 92 years without having your dick sucked?!?

He looked down at me and got all misty eyed reminiscing. I soaked it up, and he murmured, “You are such a sweetheart, an angel.”

We kissed a little, and he smelled nice. He’s so cute! I think he has false teeth.

He admitted frankly, “I may be old, but I still love pussy.”

I took my leave, but not before promising him it wouldn’t be our last date.

“It was like a dream for me,” he whispered. “I feel like a teenager again.”

I have to admit, I had mixed feelings about how to proceed. I wanted to be a blessing to him, not a curse. He was pretty low before I met him, and now he had a sparkle in his eye and a new spring in his step. I wanted to keep it that way.

I almost felt like I was dating a minor, except he was a major – he was a grown man, with all his mental faculties. I’ll bet his kids (in their 60’s) would be OUTRAGED if they knew what was going on.

Was I doing something wrong, or good? What if you were 92 and thought you’d never have sex again, and then a beautiful woman showed up at your door and offered herself to you?

What would happen if we fucked? Would he get hard? Would he have a heart attack? I asked him about that, and he assured me with a smile, “It’d be a great way to go.”


I went on another date with Leonard.

We had a lovely time at dinner, even though at one point he told me thought it was “disgustin'” that I had a vibrator. (Man, if he only knew…) He declared that he wanted to replace that vibrator. I told him I was ready to have sex with him.

He was so eager and excited. I was careful to spell out the nature of our relationship, which he readily agreed upon. I told him I thought he was a nice man, and different from all the other fellows at the retirement community, so I was ready to take it to the next level. BUT, I told him, I was not looking for anything serious. He said that was fine by him.

He was so happy on our date, he had even MORE of a spring in his step and a twinkle in his eye. When we got back to his place, we went to his bedroom, which had two twin beds.

I thought we would start out with sitting on a bed and making out, but I was surprised to watch him matter-of-factly disrobe. He unbuttoned his shirt, took off his slacks, removed his socks, pulled his undershirt over his head, which left him in his striped boxers.

I sat there, unsure of what I was supposed to do. I guess I should take my clothes off, then, I thought, and undressed. I was not used to going about things this way – it lacked any seduction whatsoever.

So there I was, naked. He told me how beautiful I was, I sighed thank you, and then he laid on top of me and started kissing me. I tried kissing back, but it was so awkward. His lips pecked away at me and his tongue jabbed at my mouth. His pacemaker bulged under the paper thin skin of his chest. He ran his hands all over me, groping my breasts and touching my pussy. It was NOT sexy. It felt hurried and mechanical.

We made out some more, and I tentatively reached down between his legs to see how his penis was responding to the stilted foreplay.

At first I felt outside his boxers, then I slipped my hand inside. I felt around.

I felt around some more.

I thought, am I in the wrong place? What’s going on here?

FINALLY, I located a small, loose sack of skin between his legs.

And that was it.

OH MY GOD, I realized with dismay, his penis was atrophied! I couldn’t even discern any balls down there. Here I was planning to suck his dick, but realized now that was completely impossible – there was NOTHING to suck. I rubbed around gently, and finally located a minuscule button in the loose skin.

Then he moved down and put his face between my legs and licked my pussy. He was breathing hard and starting to sweat, so I did what I thought was best and faked an orgasm after a couple minutes. I didn’t want him overexerting himself.

He came back up to face me, and cursed himself. He was officially upset.

I said, “What’s the matter?”

He cried, “I can’t believe it’s not workin’! Here I am with a beautiful woman and it doesn’t do a thing!”

I said, “Leonard, that is perfectly normal. It’s been a while for you. When is the last time you had sex?”

“1976,” he answered.

“Really?? Have you masturbated or anything since then?”

“No, after my wife had her bladder surgery, she was out of business down there, so I figured that meant no more sex for me.”

“OK well no wonder you don’t have an erection – you’re out of practice.”

I was super sweet about it, believe me, but inside I was completely incredulous. Did he really think that after taking a break for OVER 30 YEARS, he’d just jump right back in the saddle again?

“I’m so disappointed with myself!” he shook his head bitterly. “I am so sorry, honey, for not pleasing your properly.”

I stroked his face and arms. “Don’t worry about it, it’s OK. Besides you, DID give me an orgasm.” (Yes my motto is be open and honest, but fuck, you would lie too in that situation!!!)

He told me that was the first time he’d ever gone down on a woman before.

“Oh wow!” I exclaimed. “So how was it?”

“You keep it nice and clean down there. Not like some women. They have it dirty and it smells terrible! You can smell them just standing next to them!”

Oh my fucking god. This was so surreal.

He announced in an almost angry tone, “I’m going to get Viagra so I can please you properly next time!”

I murmured some encouragement, but I knew damn good and well that would be like digging up a corpse to take it dancing.

I think there are a lot of lessons to be learned from this story, and here is an important one:


We took a quick shower, and I left him agitated and disappointed. I promised him I’d come back again soon, kept reassuring him that all was fine, it was no big deal, and that he needed to get some rest.

I visited him a few days later, and he pulled a piece of paper out of his breast pocket with a flourish. “My doctor gave me a prescription for Viagra!” he announced proudly. “I’m going to the pharmacy to get it.” I told him that was great news. I wanted him to keep hopeful and positive about things.

A couple days later, I got a call from his daughter.

It turns out she was NOT into taking her 92 year old dad to pick up his Viagra pills so he could try them out with his new lady friend. She told me coldly that I was not to see her father again.

Oh, the shame! 🙂

I was horrified and embarrassed, but most of all, I felt terrible. I knew it would be hard for Leonard to take.

The next day, he called, asking me for a date.

Dammit, why didn’t his daughter tell him she was cutting him off? Sadly, I gently told him I was not allowed to see him anymore.

He demanded to know why, and I told him his daughter had called and made it very clear that I was to stay away.

“Why, I’ll give her a piece of my mind!” he exploded angrily. “It’s none of her business what I do! I’m an adult, by gum! I sit around this place lonely as can be. I want to LIVE my life, there ain’t nothin’ wrong with what we’re doing!”

I told him I agreed with him, but I felt my hands were tied. I was not looking for trouble or to cause a rift in his family. I said, “Even though it’s not fair, you should keep in mind that your daughter cares for you and is trying to look out for you.”

We ended the phone conversation on a sad note.

The next day, he called me asking me for a date.

Then he called me again.

And again.

And again.

I stopped answering the phone, and he left me pleading messages, in turns hopeful, then demanding, then dejected. In some of the messages, he was crying, “Please honey, I didn’t do anything wrong, why are you avoiding me? Please talk to me!”

Finally I called him back, and I cheered him up by letting him know I still cared for him. I reminded him of the circumstances and that I could no longer see him. He told me he figured things would blow over and we’d be together again. I told him to keep thinking positive thoughts.

Then he called me again and again.

It got to the point where he was calling me ten times a day. My stomach clenched every time my phone rang. It was fucking horrible.

Then he didn’t call me for a couple days, and I felt relieved, but the next round of messages from him revealed that he was so despondent, he threatened suicide and got locked in a mental hospital for observation.

Of course I called him back, completely sick and wretched over the whole thing. He was so grateful to hear my voice, and kept pleading for me to come see him. He asked me to marry him, said he’d talk to a lawyer about his rights, told me he didn’t want to lose me.

We ended that fruitless phone call, but he called me back later that day, and on and on. It was a nightmare.

Finally, one night he left me a threatening voicemail. My chest prickled and an icy chill went down my spine.

I called him in tears. “Leonard, why would you say something like that? You know I’m a nice person with a good heart, why would you treat me like that? I only meant to add happiness to your life, I feel terrible about this, but there’s nothing I can do! I am truly sorry.”

He cried as well, apologized, and told me he’d stop calling me, but I should call him when I felt like it.

I hung up the phone, completely drained and devastated.

The next morning, I had my phone number changed.


mark 2017-08-28 09:44:14

Thank you for this honest account. Kat and I have been privileged to see the “fun” aspects of your work… we forget the hazards.


Kayla mccrea 2017-08-29 10:07:23

Oh wow, I’m so sorry dear. That sounds rough. *hugs


Les 2017-09-05 16:16:40

I think you are a perfectly lovely and patient person. Thanks for the story.


Someone 2017-11-18 18:40:16

Intersting story. I think, in a way, your story illustrates why families protect their very elderly men and women. Your heart was in the right place, but elderly people are vulnerable to those who might charm them in order to cheat them of their estates. An old widower who’s only been married to one woman, who is lonely for companionship, and doesn’t want to die alone is extremely vulnerable to a charming woman. It shows up in your story too, he is desperate for a companion. Your heart was in the right place, though, and I imagine that when i reach his age, some lovely woman might grace me with her presence.

“Use it or lose it.” Something important for us all to remember, indeed!


    Kendra Holliday 2017-11-19 07:56:09

    I totally agree with you. I understand why families want to protect their elder members, I just wish it could be addressed in a more rational way than as a knee jerk emotional reaction.


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