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The Most Embarassing Things...

Embarrassing my stepbrother

Posted by bonnieblubonnett on 2004-11-28 17:54:38

Here’s a female perspective on embarrassing stepbrothers. Mine was 13 and I was 15 when our folks married, and I embarrassed him pretty steady until I left home for junior college. It started when I caught him on the telephone, talking long distance with his mother. He’d just come out of the shower and was wearing an undershirt and blue-patterned briefs, kind of like Still Embarrassed’s situation. He blushed to his toes as I had never seen him like that. I didn’t eavesdrop but after he hung up, I chased him all over the house until he ran into his room and hopped under the covers. It was the most fun I’d had in a long time, I told him.

I coaxed him out and sat beside him complimenting him on his underpants and how sexy he looked. Then I asked him why he was quivering and he said he was so nervous and embarrassed and for me to please not tell my girlfriends about me seeing him, a big worry for him. All this was turning me on and I cuddled him up and assured him I wouldn’t. As proof, I told him I was having a girl party the next weekend and that I would strip him to his underpants while it was going on but that he could stay in his room. But he had to trust me by letting me do it, a big step for him. I couldn’t wait until the weekend and I was afraid he might back out.

He didn’t and after that we trusted each other and grew really close though I still arranged for him to submit to being stripped to his panties. The best times were on the weekends when my dad was on a business trip and my mom was on duty at the hospital. Then we had the house to ourselves and Cliffy would be in his underpants most of the time.

I never beat him up like Still Embarrassed. That was really pretty mean, I think. I look back on those years with great pleasure. Cliffy wasn’t a handsome hunk but kind of a bookish kid, slightly built with a thatch of dark hair and cool gray eyes plus he had a fabulously cute little button be-hind. He always made it fun for me because he never failed to become royally embarrassed during the two years we did this. Hope you'll post any other stepbrother stories out there or drop me a line at bonnieblubonnett@yahoo.com

Posted by bonnieblubonnett on 2004-11-28 22:06:43

Got to wondering if sexual activity is more common if it's step siblings rather than blood kin? Anyone care to venture a guess or insight? I know I felt a sexual attraction to Cliff and I guess he did to me. Perhaps because we come together typically later in life when on the cusp of sexual awakening. Sorry if getting into socio-psychological babble here.

Posted by the Tuffgirl on 2004-11-29 02:50:56

Sorry,I don't have any stepbrother tales.I used to torture and humiliate my younger brother.I was sort of attracted to the neighbor boy that I would humiliate.Maybe that's why I chose him,but it didn't stop me from really embarrassing him.The first time we were alone for more than a minute,I picked a fight with him,wrestled him to the ground and tore his clothes off!LOL

Posted by crawfish on 2004-11-30 03:17:40

Hey, don't worry about venturing a socio/psychological guess. I have some questions unless you want to address them on the forum which might help keep the interest and activity up.

  1. How did you and your stepbrother keep his level of embarrassment up? New activities? Scenes such as outside, in the car? Getting caught by friends or parents?

  2. Did passing through puberty with arousal, ejaculations enter into fresh embarrassments?

Thanks. That's if for now.

Posted by bonnieblubonnett on 2004-11-30 15:37:23

Yes to both questions.

(1) We used the backyard in the summer--it was very private but still risky. My girlfriends almost caught us there once. The sunroom in the winter but it could be seen from the street. After I learned to drive, we did the car thing 3 times but it seemed too risky though exciting. Went into an abandoned farmhouse once.

(2)After Cliffy passed puberty, there was, of course, a whole new dimension. We continued to observe the No Pulling Underpants Down rule, and Cliff was grateful he could retain a little dignity because of it.

I think we had about 12 sessions over the two years. It never became routine because when Cliff heard the words stripping or underpants, he entered my world under my control. We grew very close before schools and jobs kept us separate. Which was nice. Drop me an e-mail if you want the longer version, okay?