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Monday, June 13, 2016

My Sissy Story 5: Junior high and discovering boys

So, Timmy and I were "playing house" a lot as we entered junior high school, which in our school district was grades seven through nine, pretty much ages 13 to 15. We were doing it after school when we could and at least one of the weekend days.

I remember what happened next vividly because the events pretty much changed my life:

One day, Timmy and I were at his house in the attic apartment when his mother shouted up that two boys were there to see him. They were two boys who were actually nice to us despite the fact we were sissies. Most of the boys were not nice. So Timmy went downstairs to bring them up.

The first time the four of us were up there together we just sort of hung out and listened to some music and talked. This happened another time too. After the second time, Timmy wondered why those two boys were being nice to us? They were not sissies like us.

The third time we were together Timmy goes into our stash of clothes in a dresser and pulls out two bras, two garter belts and two pairs of stockings. 

The boys laughed and dared Timmy to put them on! 

I said, "Go ahead Timmy, put them on."

He said to me, "Not unless you do too."

The two boys started cheering us on to put on the items!

Timmy and I looked at each other. We started to take our clothes off, down to our panties, which made the two boys quite amused. Then the panties came off! I remember how they snickered at our little things!

So were stood there nakie with these two boys, who were having a fun time watching us as we each put on a bra, garter belt and stockings!

Now, I had been seen nakie in a locker room with my little thing, but that was the first time that anyone besides Timmy had seen me dressed as girl!

The next time we were all together, this was all repeated. And by now, Timmy and I knew that these boys were not there to just sit around with us. This time, we started messing around, trying to tickle or pinch each other and the boys were trying to smack us on the butt. Horseplay type stuff.

Timmy and I had on our bras, garter belts and stockings that were his mother's actually, with our little things showing! We told the boys that they had to get nakie too! And so they did, willingly. We kept up with the horseplay after they had their clothes off. The boy I was with kept grabbing me by the wrist and trying smack my ass. 

And he also kept trying to tickle me. Now, I am very, very, very ticklish! Did I mention I am extremely ticklish! So, he's doing it to me unmercifully and I'm pleading for him to quit so I don't pee myself and I drop to my knees right in front of him. 

Out of the corner of my eye, I see that Timmy is on his knees in front of the other boy and he's giving him a blowjob. I don't know if that was Timmy's first time, but I suspect that he was holding out on me and that it certainly was not!

So, I turned back to the boy whose dick was dangling right in front of my face and I gobbled him into my mouth! It was still soft but soon he had a boner in my mouth! And so it was done, my life was taking a sudden turn!

I kissed and licked and sucked on his cock and balls and it was so awesome! Timmy was doing the same to the other boy. The boys were looking at each other and laughing and talking back and forth about who knows what.

I lost track of what Timmy was doing and I was enjoying what I was doing for, I don't know, maybe 10 minutes, when the boy shot his load into my mouth. Not knowing what else to do, I swallowed it. I remember both the boys saying "That was awesome!"

I didn't know what to do next so there was a pause as I remained on my knees on front of him. So I stood up and started trying to tickle him back like he was doing to me before I dropped down to pleasure him. But he was so much stronger than me that he was able to grab both of my wrists to stop me. And there was more horseplay like before the BJs and my boy kept trying to smack my butt.

When things settled down the boys got dressed and left. Timmy and I stayed in our lingerie for a while and we were both amazed at what had just happened. Then I remember Timmy saying something like, "You know, they are going to blab to everybody." At that point, we didn't know what to say or do, so we got out of our lingerie and I went home.

I remember lying in bed that night with my mind racing between thoughts of "Oh my god what did I just do?" and "Oh my god that was so great!"



Nancy Lewis said...

Very nice post. Thanks for sharing it. Although I didn't act on my fantasies when I started thinking about boys (age 13), I will never forget the first time a boy kissed me (age 15) and the first time I pleasured him. Both were wonderful.

jimsub said...

Loved the story. Puh -leese keep writing

Sissy Mishel said...

Your story makes me sit back and think about my young teen years where I was more interested in touch boys than girls. Its funny how your stories jog my memories and I sit and smile of all the things I did with boyhood friends and the times we had.
Thanks for posting.

mbenn2571 said...
This comment has been removed by the author.
Nancy Lewis said...

Your post brings back memories of secret thoughts I had as I grew up. At 5, I knew I was born to be raised as a girl. But it didn't happen. The subject was verboten and information was non-existent. To do research required a visit to the local library. And nothing was there.

Fast forward to age 12 or 13. By this age, I was cross dressing frequently. I had an older and a younger sister, so sneaking their clothes and accessories was easy. Eventually they discovered what I was doing. Fortunately they accepted me because they loved me. I became a new sister.

When My older sister started dating (she was 17 and I was 12), we sat for hours talking about boys and dating. I was so envious, I could scream. Thoughts of being on dates, being kissed and desired kept me going for many years after. I fantasized about it and still do.

Throughout your life as a sissy T-girl, what derogatory name have you been called the most?

Why do your wear bras? Or not?

Ever pilfer panties from a girl's drawer, clothesline or laundry, etc?,

How do you wear your pantyhose?

As a young sissy, did you look at naked men in locker rooms?

Did you ever raid a clothesline for bras or panties?

Do you hate getting erections?

Do you want to have your penis removed?

Do you take female hormones to be more girlie?

What is your mental state as a T-girl who wishes they were a girl?

Do you tuck away your sissy clitty to pretend you are a girl?

Do you wear a bra on a daily basis?

As a t-girl, what do you shave? (Pick closest choice)

What is your favorite lingerie?

You have always wanted one, but what would you call it?

Did you have a crush on a boy when you were in high school?

When you see a gorgeous girl, do you want to:

At this exact second, what are you wearing?

Do you use feminine protection?

Who was the first female you envied and wanted to be like?

Growing up, did you place dress-up with a sissy friend?

Did you play with dolls like Barbie and Tammy as a young sissy?