The Youngest Guy I've Ever Dated

Do you know how many college students fantasize about hooking up with the professor?

As far as I can tell, all of them.

I got my Ph.D. at age 40 (no, I wasn't in school that whole time), and began teaching.

Some of the boys in my classes would sit with their legs spread wide, unbutton a few buttons of their shirts to display some chest, drop by my office with little gifts like a can of soda, invite me to venues ("I'm singing at open mike night!").

Jostling for a higher grade?  Maybe.

It wasn't just my own students.  It was everywhere on campus.  The guy who sold me yogurt at the student union, who checked out my books at the library, who worked out next to me in the gym.

I'm 54 now, older than the fathers of most of the boys, but the cruising continues unabated.

The most recent was in February of this year: Scott, a 22-year old theater major.  I saw him in Shakespeare's Love's Labour's Lost, for which the actors wore bulgeworthy Elizabethan tights. His was rather well put together.

He was cute above the belt, too: rather short, with curly black hair, brown eyes, a square jaw, and a solid physique.

A few days later, at brunch, Scott was our waiter!  I told him I was a professor at the college, praised his acting talent, and claimed to be his biggest fan.

The next week, we went out to breakfast again at the same time, and made a point of getting Scott as our waiter.  When I paid with a credit card, he said "Could I check your id, Professor?"

No one ever calls college professors "Professor."  It felt weird.  But I handed him my driver's license.  "Ok, you have my height and weight," I said.  "What other measurement would you like?"

Scott laughed and handed my driver's license back.

I went home and friended him on Facebook.  His timeline and personal information didn't give a clue about whether he was gay or straight.  But mine did.

I waited for him to figure it out and react.  It didn't take long: the next day he initiated a facebook chat, and invited me to get coffee at a lesbian-owned, gay-friendly coffee house. Definitely gay!

He talked about growing up in a small town in Minnesota, feeling "different," and finding a safe haven in theater, and I told him my best "dating a celebrity" stories.

He wasn't impressed by Michael J. Fox, Cesar Romero, or Richard Dreyfuss.  But Andrew Lloyd Webber!  "What was he like?  Did you do anything?  Was he hot?  Do you have his phone number?"

After coffee and listening to a weird local band, Scott invited himself back to my apartment, a few blocks up the hill.  I was going to show him my collection of classic musicals on DVD, pop in On the Town, and then make a move, but the moment we walked in the door, he pounced. Before I knew it, we were rolling around on the living room floor, and he was moaning "Take me, Professor!  Use me!"

Ok -- my name is not "professor."  This isn't Gilligan's Island.

He was done before I even got his pants off.

"Sorry, Professor..."

"Boomer..."

"Sorry, Boomer...this has been a fantasy of mine for a long time."

He was willing to stick around for a bit, but still....



The next night, we had dinner at the Indian place downtown.

We returned to the apartment and sat on the couch to watch Chicago.  But we didn't make it far into the first scene.  Suddenly Scott was on my lap, kissing and groping me and moaning "Punish me, Professor!  I've been bad!"

Obligingly, we all went into the bedroom and took off our clothes.  Scott had a nicely muscled, slightly hairy chest and a nicely shaped Bratwurst.

"I want to spend all night with you, Professor..."

"Boomer."

"Sorry...um... Boomer.  I want to try everything with you!"

"Let's start by getting into bed."

I took him into the bedroom.  Instantly Scott was on top of me again, groping, whispering "Could we do it in your office, Professor?  Pretend I'm failing class, and I have to do something to pass."

"I don't do anything on campus," I said.  "That's inappropriate.  And call me Boomer."

But he wasn't paying attention.  He was lost again in his fantasy world.  "Professor, tell me I've been bad, and you're going to punish me.  Keep me after school.  Spank me with your belt.  Make me cry..."

And he was finished.

Ok, if Scott wanted role-playing, he would get role-playing!

I invited him over for a "special evening."  I draped the bedroom in black, put black sheets on the bed, and borrowed a lot of S&M equipment from a friend: black-painted rope, handcuffs, clothespins, three whips, a paddle, a ball-gag, a blindfold, and four dildos (including one too big to actually use on anyone).  Chaps and a leather vest completed the scenario.

When Scott came to the door, I brandished the whip and said "You're late!  I don't abide tardiness!"

"There was traffic." he said, staring, annoyed.  "Chill."

"Um...come into the dungeon for your punishment."  I took him by the arm and dragged him into the bedroom.

He stared at the equipment.  "Um...hey, I'm not into pain,  Or toys.  Or getting tied up.  Couldn't we just do...you know..kissing, oral, regular stuff?"

How embarrassing!  "Sure, ok.  Let me just get out of these chaps."

"Let me help you out of them."  A moment later, we were rolling on the bed, and Scott was murmuring "Take me...use me...punish, me, Professor!"

"Boomer."

By the way, with Scott, I surpassed my age gap record.  He was 32 years younger than me!

See also: The High School Bodybuilder; The Hookup Contest Part 2, and Our Date with the Teenage Beach Boy.

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.