Unexpectedly, My First Kiss With A Girl Was Only A Couple Weeks Before My First Kiss With A Man.

There are so many good "first-kiss" stories but mine is a bit noteworthy in that I ended up having my first real kiss with a girl …in the same month I was kissed by a boy.

I’m almost embarrassed to say how late I was coming to the dating party.  I turned 20 earlier this year.  I have always been pretty shy and was raised at home by my mother and sister and was home-schooled …which by the way, is a good way to stay completely hidden from the rest of the world.

I moved out of the house shortly after my birthday and in with my sister, Cindy.  From that point on, I was being pushed by Cin to start my social life.  This quickly led to her setting me up on an online dating site where I could meet people behind the safety of my keyboard.  The reason this was somewhat of an issue is because, uh …I have only been living as a girl for the last several years or so and most people only know me as a girl.  As you can imagine, it is easier to explain certain things over the internet than in person.

Online chatting led to meeting Samantha and it took two dates with this beautiful girl (real girl) before I discovered shortly after dinner at her house what all the movies and books were talking about …sweet, great, thrilling, exciting …and that was just the kissing. 

The 2nd part of my “1st kisses” was a bit more unexpected.  Even though my sister believed I was inclined to like girls, she strongly encouraged (forced is probably a better word) me into accepting a lunch date with a young man that I had been chatting with online.  Although I never told her specifically that I only wanted to date girls, I think she sensed that I had some kind of unresolved interest in men.  (10 years in skirts and dresses will do that.)  

Wth my sister lurking in the background, I was incredibly nervous during most of the lunch but Jacob worked hard to put me at ease. He was handsome and funny with a dry sense of humor and eventually I relaxed enough to enjoy myself.  It was the first time I had ever talked with a boy (or man) who knew who I really was and it was very intimidating and kind of embarrassing on my part.   After a long lunch I finally excused myself after my sister flipped me the “bored and ready to go home” sign from a few tables away.  

He was a gentleman and walked me to my car unaware that my sister had been nearby the whole time.  We chatted briefly about getting together again while I dug for the keys in my purse. When I turned back I unexpected received the 2nd first kiss in my life ...my first kiss from a man.  I am sure my surprise was evident but he kept it going long enough until my eyes closed and my lips softened.  A moment later I was in the car, and a few moments later Cin was slipping in to the passenger seat with a big grin on her face. I knew I was entirely red with embarrassment having kissed him in front of her.  But the kiss was very nice …a bit more intense than my 1st-first kiss and I can still remember the touch of his hands on my waist.  It left me a bit unsettled but not in a terrible way.  And so went my first kisses in the summer of my 20th year.

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26-30
11 Responses Dec 14, 2012

I still haven't had my first passionate kiss with a man, but I can't wait until it does happen :)

you have a wonderful sister! She has your back each time!
Life is fantastic when its full if firsts!

beautiful experiences

Cute story. When I was 15 I had a hot best friend and we would sometimes "play" with one another which usually meant me sucking his ****. I will always remember our first and only kiss. It lasted several minutes, tongues intertwined, licking one another's lips and the passion I felt for him.

I started sucking my best friends **** when I was just 12 years old! At present I am bisexual and desire my wife & men. I am out to my wife which is a relief but she does not want to know about my trysts with other men nor participate with them and would prefer I not do anything but with her. I am attracted my men my age and younger and just love sucking ****. I have only swallowed twice but sucked the ***** of 10 different men. You have to experience a **** rubbing against your panty clad ***. It feels so awesome and even better if he pulls your panties aside and **** on your *** so you can feel the warm sticky *** drip down your crack and hole and onto your balls, just incredible and made me feel fo sexy & feminine. So hard to find a safe, sane, DDF **** I can suck regularly!

I was kissed by schoolboy in the park and felt sooooo wonderful dressed as teenager wearing mini skirt. I had to push his strong hand away from my panties, I didn't want him to find out what I've got. That..........KISS aaaaahhh .....I got wet in between my legs, true.

I was touched by your comment about "...the touch of his hands on your waist." THAT must have been wonderful. Almost as much as his kiss.

A very sweet story...but I think it may have answered some questions for yourself. As you say, "and my lips softened"...was very telling, and stimulating for me. I think a kiss is as wonderful as sex, sooo intimate. Love, Marcy

As it should be. Sex is wonderful...but I equate a good kiss with a true giving and receiving of love.

Did the guy that kissed you know your little secret?

so did it make you want to explore that feeling some more...with him? Proud of ya!

Well articulated stories!

WOW sounds like you did a lot of catching up in one short summer I guess you have had a more active personal life than I have. I went to public school my entire career and I never kissed a girl or a boy. I was 33 when I kissed my first man and he was nice but not the man he made himself out to be. I have yet to have my first kiss with a woman but I hold out hope that it will happen.

Well let's hope it doesn't take another 33 years for a first I thank you for your encouragement and I think I will find someone soon.