ways to come, or not

Before sex with girls, I masterbated all the time. I always just used my hand, with no lubrication. It wasn't like I had instructions: it was a trial-and-error kind of thing (there is probably material for a mini-blogpost in that subject). It wasn't until a lot of years later that I realized that guys usually used something for lubrication.

I was a kid living with my parents and didn't want to get caught so I tried to get it done really quickly. I even timed myself, and found I could regularly come in about 2 1/2 minutes.

Then one day I read about guys who came too quickly and how it left their partners high and dry. One theory for how they got that way was that they had been in a hurry when masturbating, because they didn't want to get caught, and they had trained themselves to not be able to last a long time. This was of course familiar to me and the last thing I wanted to be was someone who couldn't satisfy their partner. I started training myself to last a long time when masterbating. Soon my masterbation sessions were taking maybe 45 minutes.

When I finally started having sex with girls, I found that they really turned me on and that I loved licking them, but fucking them wasn't that satisfying to me. Its no surprise now really, I had trained myself to need a lot of stimulation and a lubricated pussy wasn't the sensation I needed to come. I probably have only come once or twice my life while fucking someone.

The fact that I couldn't come while fucking a girl meant that I didn't have the problem I had worried about (coming too quickly). I could always fuck her until she came. It did raise a question most guys don't have to worry about: when should I stop fucking her? Its an awkward situation.

To come, I ended up masterbating after we fucked. I think this made my girlfriends tend to feel like they hadn't really pleased me even though I reassured them that sex followed by masterbating led to better orgasms for me than just masterbating. And it was true.

I remember having a girlfriend tell me that I approached sex like no other man she had been with. She wasn't saying it judgementally, she loved having sex with me. Now I think that if she had been with a woman before, she would have said that I approached sex like a woman.

When I got older, I started getting more adventurous about exploring my feminine side, including putting dildos and butt plugs inside of me. It felt good, but in the end, it often didn't feel worth the work and the mess.

When I finally had sex for the first time with a transexual, it was a revelation for me. I discovered how much I loved sucking her cock and being fucked by her. There were no drugs or alcohol involved, but when I got home and parked my car, I was in such a daze that I walked into the my car mirror and bent it backwards.

While she was (is) a woman, a beautiful woman, she brought a man's urgency to sex. Being on the receiving end of that was addicting. If I never fuck someone again, I don't think it will bother me at all.

I haven't been fucked as much as I would like, but a couple of times, I thought I was close to coming just from being fucked. That would be a level of emasculation I can only dream about so far.

jeans

So I bought some women's jeans for the first time: http://store.alloy.com/item.do?categoryID=1663&itemID=49005&sizeFilter=&colorFilter=&brandFilter=, finally.

It took a while to arrive and I had kind of lost interest by the time they did, but eventually I tried them on, and they were sooooo exciting! I stood in front of the mirror posing in them.

I'm not completely sure why they get me going so much, but I think it is because some part of me imagines going out in public in them. I think I need to wear my high-heel wedges with them, and my corset.

And the really good news is that even though they looked really hot, they were a size too big! I need a smaller size, yay!

lips

This morning I found myself looking at the web pages of cosmetic surgeons in the area who offer lip injections and other augmentations.

Mouth Gags

I have always been fascinated by gags. The way a girl looks with her lipsticked lips stretched around a gag is delicious, and of course I want to be that girl! Once I was at a play party and someone put a gag on me and for the first time I was wearing one in front of other people...it was so hot to have the power of speech completely taken away from me.

This harness style gag has always fascinated me. I imagine being made to wear that at some kind of bdsm party. Not only does it remove speech, but it treats the sub like a domesticated animal. So humiliating! I think a leash would be required with it.

I bought this penis gag. On the inside is a tiny little penis! Really I think I was sold by the hot model. That look she gives the camera is just so slutty!

It turns out the gag is made of some kind of nasty chemicals that makes it taste like gasoline (really!). So that got thrown out quickly.

This is the current gag I really like. There is something very soothing about it in my mouth. It pushes me down into subspace when I wear it. Unfortunately, it does not look sexy on (it covers up the mouth completely, rather than showing off my lipsticked lips).

Now though, I wish I had one with a bigger penis. One that would push further down my throat, maybe an extra inch or so.

Panties

I can't believe it took me so long to find these humiliating panties. I just love the idea of clothing with humiliating words, telling the world what I am.

I imagine my mistress has me get all done up for a play party, with a short skirt and she slides the panties on me without me even knowing what they are. Later she bends me over a horse and slides up my skirt so every one can see. I hear laughing and giggling but don't know why. My mistress has me look back at her and I see a flash.

Smiling she walks over to me and shows me the photo on the camera. I can see my surprised face and that there are words, but I can't make them out on the tiny screen. Mistress giggles and says I should ask someone what they say, since everyone else can read them. Finally a couple come over to me, grinning.

The woman says that I must really be a slut if I advertise to blatantly that "I love sucking cocks". My cheeks burn with shame and I just hang my head. The man says "awww, don't feel bad sissy, I can give you something you want."

Pants

I know it is more appropriate for me to wear skirts, preferably short and flippy, but lately I have been fascinated with pants.

Pants that zip up in the back are especially hot. Also white, translucent pants really get my gears going.

I keep thinking that if I were to lose a few more pounds I could buy some tight women's jeans and wear them out with my regular clothes. Probably anybody who noticed would think I am a feminine gay man, but I can live with that, I think.