THE FIRST TIME (a very personal story)

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They say that everybody remembers their first time, but I think I remember mine a bit more than most.

My first time came after being a virgin all through high school — and even later than that, it was only after the bandages were removed that I actually hit a home run.  Seriously, I didn’t get anywhere until that gauze was unwrapped.

I guess some background is needed.

In high school, when it came to women, I was probably the biggest dope around.  I was a successful athlete and was voted the most popular guy in my class, but when it came to women I didn’t have a clue.

I remember making out with a girl (one of three such moments I had back then) — we were at her parent’s house when no one else was around.  We were going at it hot and heavy, and I had a raging woodie, but I was too intimidated to try anything but kiss her.

At one point she moved my hand to her breast, and I thought — Oh, my God . . . this is it!  I was in heaven.  I was fondling a woman’s breasts!  But I didn’t take it any further.

After a few minutes she stopped and pushed me back, looked me in the eyes.  “I’m game,” she said calmly.

But I just continued to fondle her though her blouse.

The next day I told a friend and he laughed out loud.  “Jesus, Mike” he said, “Didn’t you know she was telling you she was ready?”

Nope, I didn’t.  Like I said, I was clueless.

The summer after high school, I met a girl from a neighboring district while my friends and I were out at a bar.  I fell head-over-heels in love with her.  She became the first girlfriend I’d ever had.

We went to the New York State Fair together (it’s held in Syracuse), and spent most of our time looking at the model home interiors.  (We assumed that someday we’d be married, so why not start looking now?)

I was so head-over-heels that I didn’t go to college that fall — how could I leave, this was my first girlfriend!  I figured I could always go next year.

At the end of every date my girl and I would park on a remote road not far from her family home . . . but we never did anything beyond making out.

That was it — through the summer, then through fall, and all through those freezing cold nights in the car during the winter — nothing but making out.

Sometime after New Year’s, she began giving me hand jobs, and then performing oral sex — she was always the one to initiate these advances.

When the big night finally came, once again in the car, the most unexpected thing happened.  I was trying to slide in . . . she was a virgin, too . . . but I was the one who was experiencing pain.  It was too excruciating to continue.

“Oh, why can’t we do it like everyone else!” she whimpered.

I knew something was wrong, so I made an appointment with the family doctor.

“You need to be circumcised,” he told me matter-of-factly, “Looks like the foreskin is too tight to slip down.”

All those years growing up, I apparently had this problem but was never in a position to be aware of it.  Now, at age eighteen, I needed to be circumcised.

God, I was dreading this.

I’d had taken a job while waiting to go to college, so I had to schedule a couple days off for day surgery.  This was embarrassing . . . I didn’t want to tell anyone why I needed the extra time off.

After the operation the slightest movement caused intense pain, so when I left hospital I was walking funny.  I had to stop at the pharmacy.  The nurse had told me to pick up some iodine so I could paint the stitches several times a day.

To this day, I don’t know why it had to be iodine.  It stains.

I used thin latex gloves.  I’d take the bandages off, paint with the iodine, then wrap myself up again with new gauze.  I tried to be careful, but even using gloves my hands always came out stained red.  I’d scrub and scrub, but they’d still be noticeably discolored pink.

For three weeks I had red stains on my hands, and was walking funny.

One day my girl and I were out with one of her friends.  I was walking better now.  Her friend had this smile on her face when she asked, “What’s all that red on your hands.”  She was struggling not to laugh.  My girlfriend must have told her.  I didn’t know what to say, my face as red as my hands.

But the worst part was when I woke up in the morning.  I’d wake with a raging hard-on, and it was extremely painful.  I looked down at my dick — there were small puffs of white and pink flesh popping out between the stitches.

I panicked.  I thought the insides of my dick were popping out of its sides.  I was convinced that the operation had gone horribly wrong!  I called the doctor for an emergency appointment.

“Imagine you had six-inch incision in your stomach,” the doctor told me.  I think he was smiling as he said it, looking at my stained hands.  “That’s the size of the incision you’ve had around the circumference,” he said, “This is the way it’s supposed to look.”

“Of course it’s going to be painful for a while,” he told me, “Especially if you have an erection — it’s pulling against the stitches — but really, it’s healing just fine.”

“It’s healing nicely,” he said, “Don’t worry about it.”

As I left his office, the doctor’s nurse was sitting behind the receptionists desk.  “Think clean thoughts!” she said with a smile as I hobbled out.

After a couple of weeks, my girl and I began to get excited.  “How are you feeling?” she’d ask innocently, but I knew what she was thinking . . . what we were both thinking.  How soon will it be healed?

When the day we were waiting for finally arrived, my girlfriend had her family’s home to herself.  This was the big moment!

Yes, the big moment . . . the big moment.  I must have set a record for the world’s shortest intercourse.

You have to understand that when the foreskin is removed, the freshly-exposed tip is ridiculously sensitive.  And as a strict Catholic lass, my girl would only agree to using withdrawal as contraception, so I was extremely nervous and under a lot of pressure.

OK . . . OK, maybe I’m making excuses.  The bottom line — it was such an overwhelming sensation the first time sliding in, that I only lasted one second.

One-thousand (sliding in) . . . ONE! (pulling out!)

Fortunately, I was too dumb to know how poor my first performance had been . . . and my girl was too kind to say anything.

Anyway, things got a lot better and I went to Cortland State in the fall, but although my girlfriend and I had great sex once we got rolling — we never made it through four years.

College was too much of a distraction, and we split up when I was a sophomore.  She later married her old boy friend.

But that first time with her is something I’ll never forget.

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14 Responses to THE FIRST TIME (a very personal story)

  1. Starbucks8294 says:

    Hey dude, that’s a crazy story! I can’t believe you had the balls to tell that. On a break here still laughing. You really outdid yourself on this one.

  2. DAbertini says:

    Parts of this post were funny, other parts were way too personal. I didn’t need to know everything.

  3. Colleen says:

    I think the story was a riot!

  4. Case says:

    That’s one hell of a first time. I can see you walking funny with your red hands held out. The image is priceless.

  5. Llylak says:

    You’ve surprised me once more. I don’t know many men who would fess up to the private moments disclosed here. You obviously enjoy the humor of life even when its your own mishaps you’re laughing at, and your writing carries the story well. I was smiling at each turn. This is a very funny, human story. Thank you. 🙂

  6. Cheryl D. says:


    What a laugh out loud funny personal story. What makes it special is the level of detail and your willingness to put yourself out there, embarrassment and all. The more you reach down and pull out these wonderful emotional moments, the more I feel connected to you as a character in your short stories.

    Oh and thanks for triggering a little jog down memory lane to revisit some of my own awkward moments from my inexperienced youth!

  7. MikeQ says:

    Starbucks8294: Thanks for commenting, my friend! I think that’s why bloggers post … we imagine someone out there is reading and getting a kick out of it.

    DAbertini: I know you like the “rock ’em/sock ’em” posts better, DA. There’ll be more of those coming up. Thanks for continuing to read.

    Colleen: I realize you had to say that, Colleen … what are best friends for … but thanks anyway! And thanks for listening while I initially ran this story by you!

    Case: I can still see myself hobbling along bowlegged with those red hands, Case. I realized it was funny even at the time, … despite the mortification. Thanks for the comment.

    Llylak: If I’m going to rake everyone else over the coals, Lly, I guess I have to laugh at my own foibles as well. Glad you enjoyed it. : )

    Cheryl D: Thanks so much, Cheryl! That’s good advice, keep digging a little deeper … I have to keep that in mind. Just spent a few minutes looking at the photos on your “My Lush Life” Flicker page. I love the photos of Richie Havens. Are you going to New Orleans again for this year’s Jazz Fest?

    • Cheryl says:

      MikeQ: I am going back for the 2nd weekend of Jazz Fest. NOLA is my home away from home. Seeing Richie Haven’s was incredible. He moved slowly getting on and off the stage but once he had the guitar in his hands he was ageless. Highlight last year – Sonny Rollins!

      I really should post last year’s festival photos! =)

      Keep up the good stories! I look forward to your posts every week.

  8. Ken says:

    Ouch! Ouch! Ouch!

  9. Holy shit, Mike. I bet if the Catholics had it their way, they would install your penis on every new born baby boy so they wouldn’t ever have sex until they were married. Glad you could get the surgery. In the old days they would probably just bite on a stick and scream (more than usual) while they had sex.

    Great story. Keep the train rollin’.


  10. MikeQ says:

    Ken: Don’t remind me. Thanks for reading! : )

    TheRealBarman: On the run to work, RB, but I took a quick look at the vid you included in your post this week. “Shit people say to their bartender” … that might the the funniest one I”ve seen.

  11. Cordelia says:

    Mike, you have outdone yourself again. I love your stories :0)

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