So I’ve always had an effeminate body type. And my mom is a very loving person and a great mom, don’t get me wrong, and this isn’t like those porn videos that the title might make you think of. So growing up, I could only wear girls’ pants because women’s sizes it what fit me. And because I have a very feminine physique and face, she was perfectly fine with it. And I had always been jealous of my older sisters when we went to the beach. I remember begging when I was a teenager to wear a one-piece or a bikini Bottom like they got to.

After a year of vacation, my mom and stepdad announced that we were going on a trip. And my mom said she’d let me wear a girls’ one-piece, and we went to a store. She went into the changing rooms with me and made me try on all the kinds, adjusting and tugging as she went, and she was smiling the whole time. She said multiple things. I remember a couple being, “No one knows you’re my son in the girls’ changing room because you look nothing like a boy.”

I remember asking her about the bulge and being scared people would realize I’m a boy. She looked at me and said, “That won’t be a problem for you,” and she even went a brought in a bikini thong (pretty much). I said I liked it, and she told me she “wanted to see something,” so I tried it on. I was embarrassed because she looked at me and said, “Are you tucking yourself?” and I said no, and she almost didn’t believe me. And she said how much of a girl I was turning into, physique-wise wise and spanked me playfully, and I got both the bikini and a one-piece, and we went on vacation.

Well, I’m nervous about going out, and so my mom goes with me to the pool with my stepdad dad and he ends up going over to the hot tub. I’m in the bikini, and she tells me that working out with my older sister, who is a trainer, has been really helping my physique. We start doing things like diving off the diving board and having fun, and no one else is there. And my mom does a flip and says she’s done because water in her ear, and then I do, and I flip, and as I went down, the force took off my bottoms, and I couldn’t even tell until I went to get out, and as I reached up to get out, I saw her start laughing. And I felt a sudden chill, and I just realised holy shit my dick is out, and she just says, “It’s OK. I can’t even see it,” and puts her thumb over her eye and says, “It looks how I remember it, maybe even smaller” and she gives me a towel and I run off and cry.

And I go into the girls’ bathroom, and she comes in and reaches over and hands me my bottoms, and tells me to come out, and I do. She just hugged me and said she was only joking and that it’s ok to be tiny, it doesn’t define me… but I liked the jokes and I realised then I liked SPH before I even knew it was a kink and I told her I liked the jokes and she can make them if she’d like but I tried being cool about it.

She said, “Don’t worry, your father was tiny as well, but he wasn’t as cute as you, girly” (Girly has always been her nickname for me.)

And this is how it began: years of jokes, playful digs, and banter. She was a teacher and was mine for basically most of my life. And funny enough, it was a domino effect because I’d have girl crushes come over. They’d see my dick and just laugh and tell me I’m better off with guys than trying girls because: “thank goodness you have an ass to make up for the lack of dick.”

I’ve been told that I’m both the most “fuckable femboy” and the most “unfuckable white boy” simultaneously.

It also didn’t help that I wore leggings, leather pants, and jeans that were all girls’ sizes.

One time, a girl I really liked tried giving me a shot, and so she tried sucking. Still, she couldn’t even tell she was sucking anything because it felt like a “less thick ring pop” (never heard that before then, and it stuck with me).

I tried missionary, but I couldn’t because it just felt like awkward scissoring to her. And then she tried riding me, and I went limp because of the pressure she was putting on my dick when she got on top of me, and she was trying to apologize and thought maybe reverse cowboy would help. I couldn’t make it past her butt cheeks.

She got in doggy, and I couldn’t get past her butt cheeks. She spread open her cheeks, and I couldn’t even really get into her pussy at all. And when I started trying to fuck I could only go like 15-20 seconds before I started falling out. Then she got upset, and when I got back “inside” she let go of her ass and started throwing it back and said, “Real men could handle this… Real men like girls’ asses.”

I tried, but I fell out immediately and was just fucking air in her cheeks before falling out.

She told me how pathetic I was and how much she was grossed out by it. She said she doesn’t know which was more impressive, the fact that a dick could be that small or that my ass and body were a girl’s. And put up pics of my classmates dicks and compared and just laughed. She kept making jokes and digs.

My mom, the teacher, wasn’t much help because she was considered the young MILF teacher, and I’d get told I looked like her, which was fine eventually as well. My mom’s solution was to dress alike. And what’s funny is, I’d be wearing these tight ass clothes and get “hard” and no bulge. I’d wear a bikini or one piece and get “hard,” no bulge.

Anyway, I just needed to vent a little about my life.

Sorry for bothering you all.

 

The End.

 

 

*The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free websites and is now in the public domain, allowing us to republish it here.