Introductions discussion

Hi there, I’m Steffie. I am a transgendered submissive who is lucky enough to have a wonderful Mistress who loves me exactly as I am. She refers to me as her “girlie boy,” which fits perfectly. I possess an unusual 50/50 blend of male and female characteristics. I feel blessed by this, having drifted back and forth across the gender line for most of my life without much trouble. Half of my friends have never seen me dressed like a man—and vice versa. It’s been a great life.

I didn’t really think about chastity until I met the Mistress who came before my current one. Both women are strong advocates for control. So, over the past three years (with pauses between relationships), I’ve spent time in chastity. My first Mistress loved teasing me throughout the entire weekend. She had a robust libido—stronger than mine—and she was the first woman I’d met who could achieve an orgasm while wearing her strapon. That made it a favorite activity for her. It sounds like something out of a fantasy, but it’s real. She was an amazing lover, better than most men I’ve been with. Her main approach was doing whatever she pleased with me all weekend long—and if I behaved well, I’d get some form of release before she departed on Sunday. This kept my behavior in check! Mostly.

Then there was the weekend where she went at it relentlessly Friday and Saturday. By Saturday night, I was so horny that once she fell asleep, I slipped into the bathroom to masturbate. Naturally, she caught me doing it. I got a solid over-the-knee spanking for my trouble. The following week, she announced she was testing out chastity devices. We ended up buying a cb2000 from Purple Passion. At first glance, I thought, “Oh, this is pretty cool. A new toy. How kinky.” But after just one night in it, I was begging her to remove it. Previously, when she teased me or made love to me, I could still get erections and rub against the sheets for stimulation, even if I couldn’t cum. With the cb on, I started going a bit mad. It felt more frustrating than before!

My Mistress loved all of this. It became part of our dynamic. She usually let me take it off Monday & Tuesday. But every Wednesday she’d call and order me to “Put it on! And send me a picture.” She liked the idea of denying me for a couple days prior to her arrival, saying it got me ready for when she came home Friday nights. I recall some nights she arrived late after drinking with friends around 2:00 am, climbing into bed behind me while wearing her strapon and going at it hard even though I was half-asleep. I’d be begging her to please take off the cb, but of course, she never did. My pleading only seemed to add to her pleasure.

My current Mistress is very much alike. However, she doesn’t let me take the cb off on Monday & Tuesday. She prefers longer-term denial and usually makes me wait about three weeks. She’s also into cuckolding, which is new for me. I haven’t met her lover yet; he’s a lawyer and sounds incredible in bed. She’ll be with him tomorrow night, and she’s been teasing me all day that he will have more orgasms tomorrow than I did throughout all of 2009!

She teases even harder than my first Mistress and enjoys humiliation much more, though not the hardcore physical pain (which is a relief!). As a submissive, I’ve always felt we’re just along for the ride. You never know where your Mistress will take you. Personally, that’s half the joy of being in a D/s relationship. You don’t know where she’ll lead next. The journey might be bumpy sometimes, but I love it. I can’t imagine living any other way.

steffie