One of the reasons I enjoy writing this blog is that it serves as a diary of sorts. It is usually while slipping into my lady things and feeling the feminine vibes and then getting my inspiration into words. I also have a separate little black journal I write to although it is not quite as extensive in my (perverse) thoughts as it is here. The journal is also a lot harder to hide from people in case I’m dumb enough to leave it on the coffee table, which tends to happen on occasion.
(Note that you may have noticed a lapse in time last year. Just assume I was macho me the whole time, OK?)
Having this blog means I even like to go back and read my own writing to see what I was thinking about at some random point in time in the past, which tends to amuse me today. I ran across one entry in particular about my evolving bi-curious nature, though, which I felt the need to revisit since my sexuality has taken quite the detour from nearly ten years ago.
Back then I was coming to terms that I was wanting more than just “vanilla” hetero relationships and felt an urge to explore my sexuality. from the perspective of a woman, or kind of like one at least. I didn’t want to just dress up. I wanted to be the woman that gives the blowjob or takes a good pounding (albeit from the rear). It felt sexy and exciting to fantasize about it, plus it went everything against my rather conservative upbringing which just made it all the more exciting.
I asked, I received.
Sharon was excitedly busy giving me the blowjob of her life when I suddenly had a moment of realization. There I was lying on the bed in my bustier and pantyhose and with a hole in the back that I could still feel wet from the lube Sharon had used to wet her cock that pounded me a good thousand times or so. The sexy crossdresser making me her toy and actually getting my silkies dirty had always been a fantasy of mine.
Yet this had turned into everything I imagined it would which struck me as odd. Does anything, especially a fantasy, ever end up being like you dreamed it would? “Maybe it would come close,” I thought as I watched Sharon’s head bob up and down and drowning in her sucking prowess. Nonetheless, I enjoyed the moment and the absolute “naughtiness” of our sexual encounter. I was at the peak of feeling feminine and sexy and never wanted that to end.
Sharon stopped her her vigorous blowjob all a sudden and climbed over me and into the cowgirl position with her ass just above my still-hard cock. She pulled down her black Oroblu pantyhose just enough so her bare ass was exposed then leaned over and gave me a soft kiss along with her sultry smile. As she reached for the lube nearby, I caressed the smooth, shiny nylon covering her legs and indulged in the feeling as they even rubbed against my own pantyhosed legs with every movement she made.
Sharon giggled for a second and made a humored attempt at an access hole through my pantyhose by poking her rock-hard cock into it several times while I’m on my back with my legs pulled as far as they go. As I anticipated her “entrance,” feeling her cock in and out and just barely teasing my ass was, in fact, a turn on. The tease made me so wild with anticipation, I start to tremble from the excitement.
Yet, realizing that the nylon and spandex was tough to break, Sharon ripped a small hole with her fingernails just below the crotch area and gently widened it exposing my asshole-turned-vagina. I even noted to myself, it would have been wet as possible if it weren’t for those damn gender differences. Oh well.
I grabbed a condom and lube, conveniently laid ready in place on the bed, and unrolled the condom onto her cock in a smooth, single stroke. Next, I squirted a little lube into my hand and softly stroked it over the condom-covered-cock while she let out a slow “Ooooh.”
Sharon was very gentle at first, easing her slicked love rod through my sphincter which penetrated with a little resistance but gave me a shock of excitement throughout my body. I remembered thinking “Oh my god, there is a dick inside me!” Even a wave of panic came across me.
It’s not news that I’m willing to stray from my traditional vanilla hetero side and indulge in an escapade with another sexy crossdresser. It was my first time and it was a little awkward, sure, but not any different from that first time with a GG girlfriend many years back. The seed had been planted, though, and the next time would be a far better experience for certain, much like where the vanilla hetero experience took me.
Bisexuality is still something relatively new I’ve dabbled into after straying in and out of the bicurious phase more recently. To be quite honest, it excites me now more than ever before and will go out of my way to explore it when I have the chance. Then, of course, I have to spill it all here, not to brag about the conquest, but rather share the experience. So keep in mind the name here is changed to preserve the identity of that dear crosslover.
I have to admit that crossing that line I’ve always been taught was taboo or “wrong” isn’t easy. Also the experience doesn’t always go as planned (read the link above) but it can turn out an exciting fling which leaves you wanting more. So, whether or not you’re a relative newcomer, this could either make the bicurious in you think about that next step or possibly relive your tales of chicks with dicks.
So here goes my adventure (again)…
Some of you out there may have, at one time or another (or always), dreamed about meeting that perfect girl crossdresser. You know, she show up beautifully made up, slinky dress, expensive pantyhose and heels and smells like a flower blooming after a rainy day in Italy. Then maybe after a little wining and dining, she takes you into your bedroom and proceeds to spank and pound your ass flat and tender.
Mind that this is only after you first get a taste slurping her girl cock until she tells you when. If you’re lucky enough, maybe leaving a generous tip in your mouth and down your throat.
If you unfortunately find this absolutely disgusting or appalling, cover your eyes, find your mommy and I’ll give you the opportunity to leave now.
Great, still here?
Have you ever had an attraction to other crossdressers whether it be in admiration, willing to go the distance with a passionate foray or been there, done that? Well, for those “bi-curious” waiting for the experience no different than a teeny-bopper anxiously anticipating getting her cherry popped, I believe I came upon (quite literally) a foolproof way to determine if you’re ready or not.
I was on Twitter the other day (a more frequent occurence now) and had a look at a long lost tweet I had saved a while back…
I retweeted and saved it for a reason. I pondered in those very words a bit and I couldn’t help but to think that this was directed right at me. When you think about it, though, isn’t it directed at likely the majority of hot blooded crossdressers, transvestites and other “T’s” out there?
Yes, those of you who can’t pry themselves from the mirror dreaming that you’re either some kind of pantyhose model goddess or high-priced glamour hooker whose phone won’t stop ringing (my hand raised too). I’m fairly confident there is a huge narcissistic component to our feminine alter-egos that probably just comes with the territory.
This is Part 4 of 4 of a story when two male friends decide to have a little fun in lingerie, pantyhose, heels and makeup after a casual evening at the bar.
* * *
So there we are, Eve and I lying on my bed making out like two crazed, horny teenagers. I can’t really tell what was going through my mind, probably due to the numerous beers consumed earlier, but all I can say is that it feels incredibly exciting and I was more than willing to “cross the line” where I haven’t been before.
Part 3 of two friends in the midst of playfully crossdressing together after a night of drinking.
* * *
It was a subtle yet convincingly girlish “ooh” Adam (actually, now I’ll call him “Eve”) made. Just that one silky touch to her leg was enough to set me dizzy with excitement. Normally, being alone and caressing the pantyhose on my own legs has a similar effect. But to feel it on someone else, albeit another male, is almost too much to bear.
Eve reaches down and gently strokes my crossed leg while my excitement grows so much that I begin to tremble. She takes notice.
“Are you OK?” she asks with a smile, as if she knows exactly what she is trying to accomplish.
We come to Part 2, continuing on with the tale of two friends having an innocent drink at a bar, a crossdresser and a gay male (insert joke here). Part 1 can be read here.
* * *
Both Adam and I make the short walk to my place, half a block away. We enter and Adam sprawls himself in comfort on the sofa while I immediately head to the refrigerator and grab a couple bottles of beer.
My nervousness has calmed down slightly but I still feel rather giddy. This takes me years back (a lot of years) to when I was on my very first date with a girl named Mandy. Completely nervous and trembling the whole time, I was so excited about being on an actual date that it was too hard to contain.
“But me and Adam?” I’m thinking. We’re two friends and, while he may understand my feminine fetish and even crossdress himself, I don’t believe he gets a kick out of it. Besides, I’m not into men so nothing could happen between us.
Yet the night is still long, or so they say.
Another day, another fantasy manifesting itself in a story out of my head. I hope you enjoy ;).
I don’t normally go for men in real life but when that gentleman I meet has a side to him, sharing a common bond with me if you will, well then I may have to change the rules a bit.
* * *
It was a sunny day when me and Adam were planning to meet for a beer at the local bar. I’ve know Adam, who is openly gay, for a couple months now and, while he knows I’m straight, we get along well and enjoy hanging around together as two completely platonic friends.