Ryan's Three-Way with Harry Styles

Plains, October 2016

In search of celebrity dating and hookup stories, I've been asking all the gay men I know, with little luck.  But I got a good one last night, from of all places, Ryan H., the college track star I met two weeks ago while driving through small-town Illinois on the way back from a funeral.

Last night we were chatting on Facebook's instant messenger:

Ryan:  I have one for you.  Me and Harry Styles.

Me: For real, or a fantasy?  

Ryan:  Real.  Summer before last.

I quickly wikipedia Harry Styles.  Born 1994, member of the boy band One Direction from 2011 to 2015, five albums, five Brit Awards and four MTV Music Video Awards, "Live While We're Young" hit #3 on the U.S. charts, and "Best Song Ever" #2.  Just signed with Columbia as a solo artist.  

Google images shows Harry at several points in his life.  Rather cute in One Direction, but now he has androgynous long hair and a body-full of gross tattoos.


Me: So summer of 2015.  You were...17?  

Ryan:  Right.  Just after my junior year in high school.

Me: So how did you meet Harry Styles in your small town in Illinois?

Ryan: No, LOL, it was in Indianapolis [two hours away].  My family goes down for the weekend several times a year.  We go to a Pacers game or a concert, go to the Children's Museum, that sort of thing.  Well, this time my friend Sam came along, and there were so many of us that we got our own hotel room.

Me:  Were you and Sam a couple?

Ryan: Sam?  LOL.  He's a year younger than me, and straight!  I just like older guys.  But he's a sweetheart, my cuddly bae.  So we had it all planned out.  After they were all in bed, I snuck out -- Sam covered for me, right -- and I walked about seven blocks to the Metro [a gay club on Massachusetts Avenue].

Me:  You got in ok?

Ryan:  I had a fake id, and besides, look at me!  I've been flashing a smile to get whatever I want since I was little.

Me:  Well, you are rather cute.

Ryan: Def!  So I'm into silver foxes, hot ones like you, and this one really hot guy piques my interest -- in his fifties, tall distinguished, white hair and beard, nice muscular chest.  But he's already hitting on this cute, long-haired twink.  I don't care -- I go up and flash my smile anyway.

Me: Planning to steal the Silver Fox away?

Ryan: I don't know.  I thought maybe a three-some -- I never had one of those before. So I flash my smile, and Silver Fox gets that dopey grin -- the one you got when you saw me, right?  And the guy he's with looks a little jealous.  And I see it's Harry Styles from One Direction.  I was never a big fan, but every girl in school was into him, so I recognized him instantly.

Me: What was Harry Styles doing in Indianapolis?

Ryan:  I didn't ask.  I pretended I didn't even know who he was.

[A quick look at One Directions' website reveals a concert in Indianapolis on July 31st, 2015.]

Me: Did Silver Fox invite the two of you home?

Ryan:  We went to the Sheraton -- the same hotel my family was staying in!  So we waste no time -- the minute we get inside, Silver Fox and Harry start kissing.  I unzip Silver Fox and -- OMFG!  #Hung to his knees  #Super-stud.  Almost as big as you.  Can I see a cock pic?

[I send him one.]

Ryan:  Hot!  So I go down on the Silver Fox -- I'm really, really good at oral, by the way.  My mouth and tongue are legendary.  I unzip Harry, too, and go down on him to be polite.

Me:  How big was Harry?

Ryan: Kind of small, but nice anyway.  Very firm.  When you tell the story, make him a Mortadella, ok?

Me:  Ok.

[This bulge pic suggests a probable Bratwurst]

Ryan: Anyway, I decide I want some kissing action -- so I stand up and try to kiss them both at the same time, you know.  But they ignore me, strip off their clothes, and Daddy turns Harry over onto his stomach and starts topping him.  I take off my clothes and sort of hang around.  Daddy reaches out and gives me a feel.  Come on, I have the biggest cock in Champaign County.  I deserve more than that!

Me: Then what happened?

Ryan: I kind of kneel over Harry, and he tries to go down on me.  But it's a weird position, and he gags.  So I kiss him while he's being topped by the Silver Fox.  Really nice, by the way.  Are you into kissing?

Me: Sure, I love kissing.

Ryan: I can't wait until Christmas.  I want to spend Christmas Eve on the couch with you, wearing fuzzy sweaters, drinking eggnog and cuddling and kissing.

Me: Sounds great.  So, what happened next?

Ryan:  Nothing much.  I kind of crawled under Harry and went down on him while he was being topped. Then Daddy finishes with a gigantic roar and goes into the bathroom to wipe off.  I keep going down on Harry, but he pushes me away and goes into the bathroom, too.  I figure he's going to pee and will be back in a few minutes.  Then I hear the shower going -- Silver Fox and Harry are taking a shower together, leaving me alone on the bed, aroused, all by myself!

Me: Not cool.

Ryan:  I mean, I think I'm pretty hot, don't you?  And I have a gigantic cock.  Why weren't they into me?

Me: I don't know.  I'm into you.

Ryan: So I got out of there and went down to the fifth floor to my room, and sort of started crying in Sam's arms. #Miserable.  #Jealous.

Me: Not a positive experience?

Ryan:  Not at all!  I'd rather have the guy all to myself.  I want to take my time, kiss him, fondle him, get to know him.  And cuddle!  If you don't spend the night, what's the point?

Me:  I hear that.

Ryan: I can't wait until Christmas.  There'll be a package for you to open under the tree.  [Sends me a selfie, aroused.]

Was Ryan telling the truth?

Harry Styles was in Indianapolis in the summer of 2015, and he has been the subject of gay rumors, but there's no evidence that he's into older guys, or is in the habit of hooking up with random strangers in bars.

Ryan's story was obviously a cautionary tale about what to do and not to do on our upcoming Christmas date, and an attempt to pique my interest with references to his penis size, proficiency at oral sex, and attractiveness to men.  But he could have used any sexual experience -- why invent a liaison with Harry Styles, who I don't find attractive in the least?

Unless he really did have a three way with Harry Styles and a Silver Fox the summer after his junior year in high school.

See also: Picking Up a College Track Star; West Hollywood Stories of Dating and Hookups with Celebrities; My Christmas Date with the College Track Star.

Picking Up a College Track Star in Front of My Brother

Small Town Illinois, September 2016

We're on our way back from a funeral, my brother and sister-in-law in the front seat, me in the back, driving down I-74 through a wilderness of small towns and vast plains: Danville, Farmer City, Mahomet, LeRoy, Downs, Carlock.

Katie points to the sign of a town with a quirky name.  "We should stop there for dinner.  It will probably have a cute Mom and Pop restaurant that all of the locals go to."

"Small town locals?  Sounds scary.  ZZ Top wannabes driving red pickup trucks with Confederate flags and 'I Heart Trump' bumper stickers."

"...and rows of cute boutiques and antique shops," Katie says.

"I think we should just press on to Bloomington.  According to Google Maps, there are three Thai restaurants..."

"I can't wait another hour!" my brother Ken exclaims.  "And I'm not eating rest-stop McDonalds!"

"It will be fine!" Katie jokes.  "If your hot pink tutu and drag queen bouffant attract rednecks, we'll tell them you're my hairdresser."

To get to the small town, you drive north from the highway through one of those horrible retail strips, with a Wal-Mart, fast-food restaurants, and car dealerships.  Then through a residential district of the same white-porch houses you see everywhere in Illinois, across a river, and to downtown:

A park with a bandshell.
A clothing store for Cowgirls.
Two closed banks, a closed antique store, a hair salon, a lot of deserted storefronts, and two restaurants, only one open: The Paradise Soda Shop.

We go into the soda shop.  Maybe it serves sandwiches, too.

It's in a historic building, with restored booths and seats from the 1920s,

There's a hot bear in an old-fashioned soda jerk costume behind the counter: in his 40s, chubby, black hair, beard, nice square hands.  His name tag reads "Seth."

I go into full cruise mode: eyes, crotch, eyes again.  Unfortunately, Seth's crotch is covered by an apron.  "Hi, Seth, my name is Boomer.  My associates and I are traveling through on the way to the big city, and we were wondering what kind of local delicacies you have."

He grins.  "Well, we have sodas, malteds, shakes, and phosphates."

"Phosphates?"

"Carbonated water with all different kinds of flavoring. They were popular in the 1920s.  But we have flavors they never thought of: watermelon, papaya, kiwi, sriracha..."

"Sriracha?  The hot sauce?"

Our eyes meet with that unmistakable vibe.  "It's an acquired taste."

"We were looking more for dinner," Ken says,

"Well, there are two restaurants in walking distance: Burger King and Pizza Ranch.  But be sure to come back for a phosphate later.  I'm here until 7:00."

So much for a down-home Mom and Pop restaurant that everybody goes to.

The Pizza Ranch is the franchise run by fundamentalists, with the goal of Glorifying God with bad pizza and deep-fried chicken.  Two buffet tables loaded down with fried stuff.  A salad bar consisting of wilted lettuce and sliced cucumbers, and some long rows of family-style tables.

Where the entire local high school football team is eating! Eight beefy guys squeezing past us to get to their table, then returning for more fried stuff and squeezing past us again.

Crotch view after crotch view!

Legs and thighs an inch away!
Chests and biceps in full view!
A smile and an "Excuse me, sir" as a guy shifts toward me to scoot around.

Plus a cute boy eating with two rednecks, a pair of men in muscle shirts, and the father of a nuclear family with a blatant bulge in his pants.

There are 23 men and 3 women in the room. My kind of restaurant!

I nudge Katie. "I think I'm going to move here, and eat at the Pizza Ranch every night."

"You do, and you'll be as big as a house," Katie says.

"Ok, I'll go somewhere else for the food, and come here for the view."

I try to push us through, so we can get back to the Paradise for phosphates and cruising.  Unfortunately, we arrive a little after 7:00, and Seth is gone.   A gruff older woman takes our phosphate orders.

Seth may be gone, but there's a cute college boy a nearby booth, eating ice cream with his two friends -- both girls, I notice.  He's tall and slim, with a long face and dirty-blond hair.  And he keeps looking over at me and smiling.

Seeing a chance to cruise, I excuse myself and go over to his booth.  "Hi, you look familiar..."

"You must have seen me at the meet.  I'm Ryan H**** -- I placed at 10.23."

I have no idea what he is talking about, so I say "That sounds very impressive.  Sorry I wasn't there to see it.  I'm Boomer -- my brother and sister-in-law and I are just passing through town."

His face falls.  "Are you interested in track and field?"

"Sure, I like all sports.  I used to write for a bodybuilding magazine."

"Cool!  What do you do now?"

While the girls text furiously on their smartphones, Ryan and I talk about college.  He's a freshman at the University of Illinois, where he's on the track team (10.23 is his personal best for a 2-mile run).   He wants to major in criminology and go to work for the FBI.

"I can tell you all about the field of criminology," I begin.  Then I see Ken and Katie gesturing at me and looking bored.  "But we should be going -- we have a long drive ahead of us.  But you and I should stay in touch.  I'll give you my email address."

He thanks me, but doesn't offer anything in return.  We shake hands and head out into the night.

"I'm definitely moving here!" I exclaim..  "This place is cruisier than the Rage on a Saturday night at last call!"

"Are you sure Ryan wasn't just being friendly?" Katie asks.  "There's a big difference between friendly and interested.  He didn't give you his phone number, did he?"

"No, but..."

"Anyway, he lives 600 miles from your town," Ken adds.  "A little far for dating."

"Well, I'll be passing through this way again at Christmastime."

Back home, I look up Ryan on twitter and Facebook.  Last summer he tweeted a picture of his friend's backside with the caption "Thank God for Sam's butt."  His Facebook page has a picture of him in his underwear -- nice basket -- with the caption:  "Only ___ High School boys party in their underwear."

I'm guessing he's gay.

Suddenly my cell phone buzzes.  Ryan has sent me a photo: nude, at a pool, his enormous Kovbasa semi-aroused.  Probably photoshopped, but who cares?

I'm guessing he's interested.  

Only three months until Christmas!

See also: My Christmas Date with the College Track Star; Hookup with the Waiter at a Christian Restaurant; and Ryan's Three Way with Harry Styles.

My New Year's Eve Sex Party with the College Track Star

Indianapolis, December 2016

I had been looking at pictures like the one below, and reading sext messages, for three months, ever since I met Ryan H., the college track star, in a diner in small-town Illinois.  Finally, just before Christmas, I drove into Champaign, and he took me out on a date, which involved meeting his parents, a wrestling meet, a mediocre dinner, hanging out with his friend, but NO SEX.

Three months of anticipation, and I didn't even get to go down on him!

Ryan asked me out on a second date, to a "21 and Under" pizza party in Indianapolis on New Year's Eve.

I never go out on New Year's Eve.

I definitely didn't want to go to a teenage party at age 56.

And I DEFINITELY definitely didn't want to go to a teenage party that results in nothing more intimate than a kiss on the doorstep.

But take a look at that combination of face, physique, and Mortadella+!  Maybe there's some way  I can talk the conservative Ryan H. into dropping his drawers.

I texted him and offered to take him to a "Real West Hollywood-style Gay Party" on New Year's Eve.



"I've never been to a party with all gay guys before," Ryan said.  "Sounds exciting, but I'm also a little nervous.  There won't be any drugs, will there?"

"No drinking, no drugs, just some desserts and party games."

Now I just had to arrange the party.

I asked Tyler to be the host.  He's the "son" of my ex-boyfriend Fred (actually the son of his roommate): a chef, 33 years old, very tall, with a tight physique, curly black hair, a scrubby beard, a hairy chest, and a cut Bratwurst+.

I contacted the other two gay guys I knew in Indianapolis, Ryan the museum guard and Simon the church organist, but they were both busy.

 "I'll take care of the party guests," Tyler offered.  But by December 28th, he had managed to get solid commitments from only two of his ex-boyfriends (Jesse and Sandoval), both bears in their 50s.

Tyler likes them older.

Five guys is enough for a West Hollywood-style party, but there should be a mix of sizes, shapes, and ages.  Ryan H., at age 19, would be the youngest guy there by over a decade.  I needed to get someone close to his own age.

Fortunately, I'm a twink magnet.  On December 28th, I got cruised by the waiter in a crazy retro restaurant: Mike, age 23, medium height, on the thin side, with a round face, heavy eyebrows, and short brown hair (top photo).  We went out on the 29th (oral bottom), and I invited him to the party.

That made six, a perfect number.

Most West Hollywood Parties begin at 6:00, but since it was New Year's Eve and we would be up until midnight, I picked up Ryan H. at the Sheraton at 7:00 pm, shook hands with his parents, and kissed and groped him in the elevator on the way down to the lobby.  Then we drove to Tyler's apartment.

Pre-Dinner Conversation

The usual coming out stories, dates from hell, enormous penises, and celebrity hookups.  I told about my date with Michael J. Fox, which impressed the older guys but not Ryan -- he looked away.  I started telling about my hookup with Justin, the supersized guy at the gym, but stopped when Ryan picked up a magazine.  Bored? Embarrassed?

This was the guy who had been sending me nude selfies for three months.

Dinner

Tyler served a traditional Greek New Year's Eve dinner: a lamb-macaroni dish, a cabbage salad, and vasilopita  There was wine, but Ryan, Mike, and I drank Diet Coke.  Then he passed out bowls of green grapes.

"Have a mouthful of grapes when the clock strikes midnight," he said, "For good luck in the coming year."

"What if my mouth is already full?" I asked, looking at Ryan.  He looked away.

Embarrassed?  Was I doing something wrong?

The Entertainment

We played Gay Trivial Pursuit, in teams: Ryan and Mike, and Tyler and his bear friends.  I was the moderator.   In what year was Stonewall?  What gay-themed movie won the best picture Oscar in 1982?  What was the name of the first gay character on prime time tv?  Which famous American writer was gay?

Tyler's team won easily.  Ryan and Mike belonged to the post-gay generation, with mostly straight friends and little knowledge of their history and culture.

The "Guess the Sausage" Contest

Here's where things would get erotic.  Everybody had to go into the bathroom and snap a picture of their penis, flaccid, then text it to Tyler, who printed them out.

The one who guessed all five correctly got to spend 10 minutes alone in the bedroom with the guy of his choice.

It's not easy, even if you've been with the guy before. I had been with Mike and Tyler, and I had no trouble guessing Ryan's gigantic Mortadella+, but I got the two bears mixed up.

But Tyler got them all right, and chose to go into the bedroom with -- me!

I dutifully followed him into the bedroom.

"Why me?"  I asked.  "I'm staying here!  We had sex this morning!"

"I know.  Why do you think I want some more?"  He pushed me to my knees.

"Ok, but we need to do another penis contest.  I want to get with Ryan before the night's over."

"Sure, sure."  He unzipped.   I shrugged and went down on him.

When we returned, Ryan was glaring at me.  Had I done something wrong?

The Arousal Contest

For this contest, everybody had to get naked and stand still.  The first person to get fully aroused without touching himself or being touched by anyone else won, and could ask anyone he wanted to go down on him.

Older guys and guys who are well hung don't get fully aroused easily, but Mike the Waiter sprang to life immediately. And chose -- me!

"You've already been with me," I protested.  "Are you sure you don't want one of these other guys instead?"

"I made my choice," Mike said, grinning.  "Rules are rules."

I dutifully followed him into the bedroom, where we kissed and fondled, and he went down on me.

Auld Lange Syne

By this time it was nearly midnight, so we gathered around the tv, still naked, to watch the ball drop on Time Square.  I sat on the couch between to Ryan H. and Jesse the Bear.  At the stroke of midnight, I grabbed Ryan and kissed him and fondled his Mortadella+.  He smiled, pushed me away, and started eating his grapes.

"Grapes for luck in the New Year."

"Right.  I should eat my grapes, too.  I wonder where..."

At that moment, Jesse enveloped me in a hug and kissed me.  He was a good kisser, and I became aroused.  I felt someone go down on me -- Ryan, probably.

No, it was the other bear, Sandoval.

Sharing

Desperate, I pushed his head away.  "Ok, time for the sharing," I said.  "Ryan, you and me, and who wants to join us?  Mike?"

"Actually, I'm a little tired," Ryan said.  He was pulling on his pants. "It's been a fun party, but I'd like to go home now, if that's ok?"

"Um...sure.  Just let me get dressed, and I'll drive you back to the Sheraton."

"The downtown Sheraton?"  Sandoval asked.  "Jesse and I are going that way.  We'll be happy to drop you off."

A few minutes later, Ryan H. was gone, along with the bears, leaving me alone with Tyler and Mike.

Mike grinned.  "About that sharing..."

I wasn't really in the mood, but I dutifully went down on Tyler while Mike was going down on me, then bottomed for interfemoral -- Mike on top of me with his cock between my legs, and Tyler topping him.

But all the time, I was thinking of Ryan H., the college track star who I somehow managed to offend.

He unfriended me on Facebook, and he hasn't responded to my texts since that night.

See also: My Christmas Date with the College Track Star.; I Spend the Night with Fred's Son; Cruised by the Waiter in a Crazy Retro Restaurant