Sassy’s Past Part 2: Pop Goes My Cherry

Welcome to the second story about the men in my pants, oops!… ahem…past.

If you missed it and want to read about my earlier exploits, read Sassy’s Past Part 1 – The Kissers.



Senior year in high school was all about Teddy.  He was a year younger.  He was another very Italian, Catholic guy – tall, dark and handsome in a burly way, with a mustache.  His mother always called me, “That Protestant Girl.”  Teddy was around for a long time before we dated, talking to me in Drama Club, chasing after my friends.  During the fall, we were in a play together.  He pressed me against the back wall of the auditorium, wrapped his arms around me in a big hug and just held me.  I liked him but not that much.  After a month, he kissed me at the cast party.  There was something very comforting about it.  But he wasn’t Philip.  I was done with boys.  I really wished he’d leave me alone.  But he didn’t.  He kept hanging around, telling everyone he was my boyfriend.  
We told each other stories…our fantasies.  And we’d act them out.  Pretending to be a doctor and a patient.  A teacher and a student.  A movie star and her young co-star.  Always illicit.  Always a very exciting story.  But I felt like he was doing stuff to me and I was watching from outside my body.  Going just a little further each time, but stopping.  He liked to kiss and lie on top of me, but never pressed me to go all the way.  
On a cold winter night, four months after he first kissed me, we were fooling around in my bed.  He was kissing me and hot dogging – running his cock up and down my slit.  All of a sudden, he shifted and was inside me.  No big decision, just a little further and he was thrusting and coming very quickly.  My first thought was, “Is that all there is?  Is this what the grow-ups have been hiding from us?”  It seemed like no big deal.  He told me he loved me.   I answered in kind.

I didn’t know what an orgasm was in those days, but I never had one.  He was usually done long before I was even warmed up.  I don’t blame him – we had no clue what we were doing.   

He took me to my Senior Prom.  He helped me change out of my long dress and into jeans for the after-party.  I will never forget the kiss on the back of my neck when he unzipped my formal gown, letting it drop to the floor while he squeezed my breasts.  That caused quite a reaction for both of us!  I began to think about him more when he wasn’t around, miss him and want him to touch me.

I graduated and left for college in September.  I was very afraid he would forget me but he insisted that was silly.  I missed him so much!  We had long talks on the phone every Sunday afternoon.  He came out to visit once and we had sex nine times that weekend!  We kept dating when I made it home, and missing each other.  I went home for January break.  We had sex on the floor of my dad’s library on New Year’s Eve.  He told me he had met someone he wanted to marry.   I asked him to think it over.  He stayed with me for three weeks then told me it was over.  I went back to college heartbroken and determined not to date again.  
A year later, I was home for the holidays and he called me New Year’s Eve, said he’d like to stop by to return a book and music albums of mine he ended up with.   We talked in my Dad’s study.  I gave him a hug as he was leaving.  He held onto me and sighed.  Then he kissed me.  And kept kissing me.  It felt really good so I got into it, kissing him back and reaching inside his shirt to rake my nails down his back and squeeze his ass.  He put his hand in my pants and then lowered them to put a finger inside me.  We collapsed to the floor and he was inside me again.  It was incredible!  But as usual, he was done quickly.  That was our time #100.  And the end.  I never saw him again.  He continued the trend, marrying the girl he left me to date.

When Philip found me on Classmates, I noticed that Teddy had visited my profile!  Twice!  I found him on Facebook, recognized him immediately in the profile photo with his wife.  I wrote him a brief message.  No answer.  Just as well?

For a look at what I wish my first time had been like, check out my erotica at
What If Phil Was My First

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Sassy Girl

It's the gal you knew in high school that you've wondered about. And she's got something to say! Time to heat up old flames!

3 thoughts on “Sassy’s Past Part 2: Pop Goes My Cherry”

  1. Damn you were counting back them. Are we obsessive compulsive a bit.

    I bet you are the type of girl that saves all the texts and e-mails from her guy-friend! 🙂

  2. Wow imagine all the foreplay fantasy and fabulous sex thst Teddy wouldn’t have brought you. Sometimes we have to be thankful for missed opporrunities.

  3. Great post, the best take away for me was a new term.

    “Hot Dogging”. I try and come up with or get great terms like this in my blog. I am familiar with the act, but wasn’t aware of a name for it… till now!


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