Sock Monkey Weekend With RainMan

By Kendra Holliday | November 6, 2012

This weekend was all furry and blurry!

My friend RainMan came to visit. We met through my blog three years ago and have been online friends all that time, so this was the first time we met in real life. It was a bit of a blind date – we’ve skyped and I’ve heard a few of his crazy stories (being stabbed in the back – literally -, getting busted by cops for fucking on the beach, his various weird experiments), but I wasn’t sure what we had in common. I’m a social butterfly, and he’s more of a loner, Dottie, a rebel…

I asked him what he was into. He told me fishing and sailing. Well, we weren’t about to hook that up here in St. Louis, so instead I offered to take him to historic cemeteries and rundown areas of the city. He was fine with that.

Since he was so agreeable and didn’t have any strong opinions, I ended up calling the shots all weekend, which was not ideal for me, and especially not for him. I don’t always make the best choices. In fact, we spent a good two hours wandering all over the city looking for Benton Park and Lafayette Square, but kept ending up down by Anheuser-Busch brewery instead. Since he didn’t drink, we skipped that attraction, even though I could’ve drank his beers like a bully stealing his milk money.

Actually, I was a little appalled he didn’t drink. When I asked him, “Do you drink?” and he replied, “No,” I was like, “What? WHAT?”

He said, “But we can still go somewhere for drinks, I won’t stop you.”

I said, “Pfft, you couldn’t stop us if you tried. Shit, we’re drinkaholics.”

We started the weekend off at Plush, where we had – you guessed it – cocktails. And pot pie. And savory waffles.

The crystal ball at Plush says you will have an awesome time in St. Louis.

After that, we went to Fountain on Locust for dessert cocktails. I had the Wicked ice cream martini and Matthew had the banana bourbon, which was like a gorilla’s wet dream. Matthew also kept dropping things on the floor so the cute waitress sporting a shelf of cleavage would bend over and show her tantalizing tits – there, I outed him as a irrepressible cad. Now she can punch him the next time she sees him.

We parted ways for the night and Matthew and I went home and had sex.

The next morning, RainMan picked me up. I made him drive, since I hate driving and I got to call all the shots.

We went to Shameless Grounds, where Lee Harrington and Mollena Williams presented Playing Well With Others, a talk on kinky etiquette.

Let me tell you – they OWNED that place. For two solid hours, they entertained and educated. They have great chemistry, and great experience to share. The audience was spellbound, laughing and amazed. And then poof! after selling almost every copy of their book, they were on a train en route to KC for their next stop on their whistle stop tour.

I’m so dumb – I failed to get a pic of myself with them. And I even looked good.

After that, we went to the Iron Barley for lunch. On a cloudy fall day, it was a perfectly cozy choice! RainMan tried their Elvis Freakout sandwich – peanut butter, jelly, red pepper flakes, bananas, bacon, cheese, on Texas toast.

Then we stopped by Shine Goodie’s place, where she was just kicking off a Day of the Dead party. Her place is like a block home for lesbians and weirdos – a safe haven for deviants. She is the High Priestess of Humanity.

And of course I did what I always do for my out-of-town visitors who get freaked out by huge crowds of people – I took him to a big Halloween party.

We stopped by Johnnie Brocks to get him a costume. He picked up some doctor scrubs, but they were so big on him I ended up just putting a sock monkey hat on him and handing him my speculum and voila! he was a sock monkey gynecologist. Guess who was the sock monkey?


A uterine-free sock monkey, mind you.

Next, we picked up my daughter so she could attend the wildly popular Halloween party our friends throw every year. She was dressed as Jeff the Killer, a nice contrast to our cute and harmless costumes.

David Wraith and our incestuous love child

RainMan found a nice, safe corner on the social anxiety couch and did just fine. It’s where all the introverts park while all the extroverts freak out and sing karaoke. There were SO many awesome costumes – Rosemary’s Baby WITH the devil who fucked a baby inside her, TWO binders full of women, vampire May Poppins, Kermit and Miss Piggy, Laura Croft…

Amazingly, I got laid again that night, despite being dressed as a sock monkey. I’m glad Matthew knew there was a soft, beautiful woman underneath the silly monkey layers.

The next day, RainMan picked me up again at 10am so we could roam St. Louis. I decided I would continue wearing my sock monkey costume, so I ran all over town in cozy simian fashion.

First, we went to Bellefontaine Cemetery. OMG that place is amazing! Over 300 acres of haunting historic beauty – so many great photo ops. And crosses.

Bellefontaine Cemetery, where they keep it classy

We saw so many nun graves. I had to point out that they all presumably died virgins – sucks to be them.

Jesus getting head

This statue reminded me of My King…

Crowning Glory

This was my FAVORITE gravestone, although there were so many good ones!

I know that’s right!

Then we went to the Riverfront, where he got to check out the Arch from a safe distance. Then, Union Station, which is an incredibly gorgeous historic landmark. My favorite part of Union Station is this stained glass tableau showing St. Louis parked smugly between San Francisco and New York like she’s the center of the universe.

Next, we went to City Museum. Don’t you LOOOOVE taking people there for the first time and showing it off??? Always worthwhile, such a rare gem in our sadly beautiful city. This was my favorite shot from this visit, you can find this bevy of beauties down in the bowels of the cave (we did the 10-story slide – YESSS!)

Goddesses in golden glow

Then we had lunch at Crown Candy! Which means we had a crazy sundae stiff with fudge and heaped with whup cream while all the people standing in line waiting for a table glared at us with jealousy.

We tore this hot fudge sundae a new asshole.

After that, we drove ALL over St. Louis city and I told him about the history of brick I learned in the local documentary by Bill Streeter.

We took a long walk in Tower Grove Park and I gave him dating advice. He doesn’t know how to flirt or notice when a woman is interested in him. Then we had tea at MoKaBe’s.

Next, he dropped me off at Ami Amore’s studio so I could do her women’s only clothing optional yoga class. While I did that, he explored the abandoned Lemp Brewery buildings and colorful Cherokee Street.

By then, I was ready for a hot shower, so we went back to his posh hotel room. I asked if he wanted to shower with me, and he said sure, so we did. It was a little awkward, like we were in the army together. I noticed he had a great dental regime – toothbrush, toothpaste, floss AND a tongue scraper were lined up on the marble counter – I was impressed!

He was so cute and hairy – 130 lbs., with a Rorschach pattern of chest hair and really hairy legs, beard stubble, awesome vampire eyebrows and yellowy tiger eyes. He kept peering at me oddly, and I couldn’t figure out what was on his mind. Every time I asked him, he just said something that bordered neutral/agreeable.

So I took matters in my own hands and got on the bed and showed him some of the yoga poses I learned. Then I asked if he wanted to do anything. He said yes, so we started tentatively kissing. I was so excited to be with a man my size for a change!

I blew him and then he ate me to orgasm. Then I put a condom on him that I brought (he didn’t bring any!) and rode him to orgasm. Then we did it doggy style. He was very gentle and reserved. After a while, I couldn’t help but notice that he wasn’t cumming. He explained that condoms numbed him, so I took it off and went back to blowing him. After a while, I finally had to stop because I had to leave. He said, “I’m embarrassed.” I said, “Don’t be!”

When I got back to Matthew, I rinsed off and told him about our time together. “Maybe I should have left well enough alone, but I didn’t want to leave him hanging after our fun weekend together.”

“Do you think you left him better than you found him?” he asked. That’s one of my philosophies with everything – leave people, places and things better than you found them.

“I’m not sure,” I admitted. “I think by the end he was wishing I would just leave his dick alone!”

Matthew and I closed out the weekend with some crazy mean sex – he circled me like a wolf, slammed doors, cussed me out and jerked off on me. I think he was trying to balance the really gentle sex I just had, which was TOTALLY COOL! I love it all!
The next day I emailed RainMan and thanked him for a wonderful weekend, which he reflected right back to me. He said:

Awkward was okay, and totally worth it. It wasn’t your fault at all, and you didn’t push me into doing anything I was uncomfortable doing
🙂  I was ready and willing, it was just a combination of my usual problems: nervous the first time I’m with someone, being desensitized
(my cock isn’t very sensitive, so cumming can be tricky, especially if I’m a bundle of nervous energy and haven’t been masturbating, which keeps the sensitivity up). I’m just glad it happened with you and not someone else. You’re far more understanding than some people would have been

It was nice spending all that time together. It really is rare, and I definitely feel like I got to know you really well by the end. You’re
outlook is great and you’ve helped to build an amazing community. I can see why everyone likes you so much.

Thanks for the advice you gave m. I think my next project will be to learn how to read people better.

Phew, so glad. What an amazing weekend! All’s well that ends well!


Capn Marrrrk 2012-11-06 08:49:17

Ah…A Happy Ending. That’s great to hear! It was nice to meet you too Rainman. Also, look into the the stage hypnosis book. A lot of that is both learning the patter and paying attention to how your subjects respond too.

Thanks for coming to town.


Kendra Holliday 2012-11-06 17:05:08

I just want to point out that I cougared RainMan while dressed as a sock monkey. (he’s 28; I’m 40)


The Devil 2012-11-07 15:47:19

Ahh that’s who the guy with the speculum was! It does look like you guys had a great packed weekend of fun! I enjoyed reading about his experiments- I have done several that he described… Life is fun when it’s one big experiment!

It was great to see you, and imagine my surprise reading about myself right here!

Now, remember, never wash the mark of the beast off yourself.


The Devil


rarry 2012-11-18 01:24:40

If you were at the Brewery, you were in Benton Park. And if you at Shameless Grounds, you were there also, or rather, three blocks west of it. I’m not actually sure if Benton Park goes west of Gravois, but you were so close both times, you could say you were there.


Gary LaBrot 2012-12-30 21:35:43

Sock Monkeys hide at the foot of your mattress under the covers….then quickly bite off all your toes when you climb in bed!


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