ShyDeanna's Blog

Well, I've met a few great men on this site and I was hoping a couple of them might have turned out to be something meaningful or at least friends with benefits. But, after over two years it seems this site has slowed down a lot and most of the men here are much older than I am at least locally and are not interested in the things I desire. My Premium membership just expired and I have been spending more time on another website as well as a mobile app and have met way more local guys than on here. So, I'm not saying I'm leaving for good but I'll certainly be spending way less time on here than I used to especially without the premium now.

I appreciate all the connections I've made here and I'm sure I'll peek in every now and again but I've noticed I log in less and less over the last few months.

~D~

I'm amazed at how far I have come (is that a great way to start a blog entry or what?) since decided to jump into dressing more than just an article of clothing here and there. In the last few years I've bought not only pantyhose (too many pairs to count), dresses, but also gaffs (panties designed for men), breast forms, bras, wigs, makeup kits, shoes, and more. I've enjoyed dressing up and posting my pictures online, getting naked for men, and even doing a few jerk-off sessions on Chaturbate.

I've gone from wanting to just dress up as a woman to wanting to be with a man sexually. I've finally admitted to myself that my dressing is pretty much sexual although I do enjoy the inner feeling of presenting myself dressed up. I've realized that at this point in my life I really don't want to be a woman full time nor do I want to be in dress other than a few days a month even though I crave it daily. A lot of this has to do with being married and having a job where I'm expected to be a man. While part of me wants to tell my wife and continue on my path to see how far I want to go as Deanna part of me enjoys the life I have and that temptation on the side.

I've been very selective and careful with potentially having sex with a guy. I've met DOZENS of eager and nearby men who have offered to put up hotels and come over to see me, but I'm nervous of getting caught, robbed, or worse yet; getting a disease. I'm also not attracted to men other than cocks. I have no desire to kiss a man although in the heat of the action Deanna will probably take cruise control over me, but I am dying inside for not being able to enjoy a nice solid dick in my mouth and hands as well as my ass.

I don't want to lower my expectations, but I'm realizing more and more that I just really want to experience being with a man to decide what I want out of Deanna moving forward. I wish I would have had so many choices like this with meeting women over the years and I don't know why I'm being so overly cautious about things. A part of me has also moved beyond dressing up to want to be with a man and I have become willing to engage in acts with men while not dressed as Deanna. The only thing I want to avoid is getting involved with someone who is gay and may develop feelings or want a relationship. I suppose the same could happen when I'm dressed as Deanna and the thought of having a boyfriend is intoxicating and I guess I'll never know until the flesh meets flesh!!

I've been wanting to dress for quite a while but keep putting it off due to how much time it takes to get ready. Usually if I know I'm going to dress on a weekend I get my body hair shaved ahead of time and plan out what I want to wear and do. I've also had a few discussions with guys about hooking up. As much as I want Deanna to soil her oats I do find hooking up with a guy as my normal self almost as hot and way more convenient. But Deanna wants to get laid!

Anyway, I'm being overly careful as this is not only my biggest secret but I also don't want to get a disease or three. I had a close call with a girl I slept with once and I certainly don't want to get something from a one night stand or with a casual partner while I cheat on my wife. I hope my patience pays off soon as the fantasies, photos, dildos, and constant masturbation are starting to not be enough! As much as I say I'm not gay and don't want a romantic relationship a part of my heart does want a "boyfriend for Deanna" and a guy that I can have relations with instead of bouncing from cock to cock (oh my, that sounds hot though!). I do want to experiment though. A threesome with a guy and a girl or with two other guys is something on my bucket list.

That last fantasy played out during my latest photo shoot this weekend. It ended with a vibrating dildo in my ass, my knees up, me on my back, and my large pink dildo bouncing in and out of my mouth. I came very hard and at that moment I knew I wanted to experience that for real. Watching porn with others doing it is nice, but feeling it was great and doing it will be awesome.

Anyway, yes, my latest "photo shoot" just wrapped and I finally got to take pictures of me in my new "professional" dresses. I usually try to get a handful of photos in different outfits but I got a late start. Plus a strange thing happens where I seem to lose a lot of clothes during this and end up with something shoved inside of me (like what I just described above ;O ). I did take some more nude shots and along with filters they look really good. I did put up a new one where I finally took a picture of me wearing a different type of top.

Keep an eye on my pictures as I'll be dropping a new photo about once a week or more. Thank you for reading!

I've helped my wife shop for clothes in the past, but it's generally at a smaller store and a very short time with her. She's unaware that I dress as well as am into other things although I think she may suspect I dress. Knowing her upbringing she would certainly be upset enough to divorce me over just dressing (let alone if she knew I was trying to hook up with men while dressed up as a woman) so I've been careful to spoon-feed small bits to her to slowly bring her to a point where I can tell her (at least about dressing).

We are set to go on vacation soon and we were at a store shopping (separately in our respected gender areas). I showed her a couple of shirts and shorts I was buying for men, of course, when she asked me to check out the dresses with her. My heart almost skipped a beat and I found myself wanting to make a comment or put it off (like I'm programmed to as a man), but I resisted and instead happily joined her.

I was like a kid in a candy store and I caught myself holding a dress up to myself more than once. I went through almost every dress on the rack and commented on them, it was so much fun. I tried to make as many remarks as I could (I wonder if this is my size, I wonder if they would let me try this on, is this my color/style) to see if she would say something, but nope. I was also tempted to tell her that since she was looking for a particular style dress that I might actually have one she could borrow, but I know it's too big for her or otherwise I would seriously present it to her and either make up some bullshit story or actually come clean finally.

It was a fun night and I may suggest that we go out dress shopping again soon! We also looked at shoes, makeup, and other feminine goodies and I could barely contain myself. A number of women looked at my direction when I was checking things out, but I didn't care it was just so much fun but would be much more fun if I would have been dressed and could be Deanna while I did it.

First I want to thank everyone who has commented on my blog. I know many people read it, but it's nice to know that my feelings are similar to what others out there are encountering. That knowledge makes it a lot easier to deal with the feelings I've had and I've come a long way in that regard in the last few years.

When I first began to take an interest in shemales and then true men sexually I began to wonder, "Am I gay?" I can't be gay as I love women. I love looking at women, I love having sex with women and I can't stop checking them out. They do things to me that no man can as far as those feelings are concerned. But, I want to suck a dick and have anal sex, so am I gay or what? I fought through those feelings and realized it's not black and white like what people think or beat into your head when you are a kid. I remember when I was young and someone asked, "Would you suck a dick for a million dollars?" Of course you had to answer no or otherwise they would call you gay and try to beat you up. As you get older and lean the value of a million dollars and you think harder about that question, but there's the social discomfort about two guy friends talking about doing things together. The same two guys that would happily team up one one of their girlfriends together and high five each other and only talk about if their balls touched would that make them gay. Guy are just fucking weird as far as that's concerned and it took me until my 40s to realize it.

I remember comics making fun of sexual orientation by saying things like, "There is no bi-sexual, you either suck dick or you do not suck dick." I believe it was Andrew "Dice" Clay that said that (not that I took much he said seriously). Is it possible to still love women a lot, but enjoy having a dick in your mouth? I don't see why not. The world is not black and white and bi-sexuality is not a millennial thing or is it new at all. I honestly think that men are just scared of the idea of losing control of their sexuality to another man. Most men are dominant in bed, or at least say they are up front and I think it's partly this fear that leads most men to ignore wanting to experiment with the same sex.

Anyway, I've been sexually attracted to men for a while and it's easy to flirt online. I'm not looking for a gay relationship (since I'm not gay) but kind of like friends with benefits. I was talking to a guy online and we hit it off. He found Deanna very hot and loved everything about her (nothing new I haven't heard). But he wanted to know about me, my feelings about what I was going through, as well as the guy I was on the other side. It felt great. After hours of talking I really felt like I liked this guy, I was actually emotionally attracted to a guy which was a bit scary but felt great at the same time. Then I finally asked where he was from. The answer; the Netherlands. You've got to be fucking kidding. It seems like every time I meet a great guy he's from far away like South Africa (you know who you are ).

This guy was great and he had a great body and shaved cock and was just a bit younger than me. I could almost imagine having a relationship with him. Granted, I'm married (no children) and my wife has no idea about anything such as me dressing (although I think she suspects). I've been trying to drop hints for it to not be a huge surprise since I know it will not go well if it happens that way. I'm not looking to have a relationship with a guy, but the duality going on within me is pushing outward. The Deanna inside of me wants out and she wants to find a man. I almost feel like I have split personality disorder since the two are never around at the same time, lol. I'm not mental and I feared that as I got into cross-dressing, but there are no classifications of mental disorder associated with wearing other gender's clothing unless it begins to affect one's life. Shit, that's where I'm headed!

I hope I have things balanced out and all I really want is to had a sexual relationship with a guy for a bit so "Deanna" can soil her oats. Will that be enough for her or will she want more like she has been the last few years? I won't know until the cum dries.

I enjoy playing baseball, lifting things, checking out women, drinking with the guys, and just being myself. The hard thing is that I want to be Deanna a little more than I am. I don't necessarily want to be a woman full time as this would completely change my life and I do enjoy being who I am. Unless, of course, I meet some hot guy who is filthy rich and wants me to be his live in cross dressing lover! Being my normal self is really getting in the way of dressing as a woman and meeting men like I want to do. I got an ankle chain in the mail yesterday and I couldn't wait to try it on. When my wife was in the shower I tried it on and it felt so good. I really wanted to put nylons on with it over them and put high heels on to get the full feeling of enjoyment, but I couldn't. I haven't been able to keep my legs as shaved as I want to and now I have a skinned up knee from playing baseball so my favorite assets are not as good as they can be. When I see a girl I think is hot I do check them out, but then I look at how they are dressed, how they are wearing their hair, and I see other guys checking them out and wish I was her. I've grown used to this duality, but the longer the feminine side is locked up the more desire I will have to fulfill the fantasies within.

I don't mind the dual life at all and I'm looking forward to exploring a bisexual side as myself with someone soon and getting that pleasure and hopefully "sharing it with Deanna" if that makes sense. I almost feel guilty that the first thing I thought of when my wife told me she was going on a cruise next year with a friend was that I would be able to dress up all week long and maybe sneak out a few times. The one thing that keeps me going is that at least I have been able to explore this side of myself in more depth and have been able to fully dress a lot and while I don't feel passable I have been out in public and felt that rush of being checked out (and desire more of it!).

I have belonged to many websites for CDing in the last year or so since allowing myself to explore cross dressing in depth. I have had the urge all of my life, but only allowed a piece of clothing to be worn or shaving body parts but allowing them to grow back. The last few years I have kept all of my body hair short or shaved and two years ago I decided that I would finally allow myself to explore this desire more in depth.

I wanted to see myself as a woman instead of just "imagining" it. I made mistakes with buying a costume wig, but being a good researcher I quickly amassed dresses, makeup, a wig, and other essentials and it felt so great to finally connect to what I would eventually call Deanna.

I am very confident in my sexuality and know I am a heterosexual and am not attracted to men emotionally or physically. But, I did have an odd encounter with a close friend many years ago that made me realize that it would be a turn on to "play around" with the same sex. I'm a kinky person and connecting to Deanna created an even stronger urge to fulfill the fantasy of being more "like her" and ultimately being taken by a man. I went from obsessing over shemales to start to find men attractive sexually and these feelings have grown stronger over the last year. I guess I've just opened up sexually since opening up to Deanna to the prospect of being bisexual (I've always thought about it, but never allowed myself to go this far).

I began to be flirted with by a few men on a couple of cross dressing sites and it continued heavily when I created an online account on an adult oriented social media site. Many men claimed to want to be with me, experiment like I wanted to, and just have sex like I really wanted. But, when I made the time and effort to make it happen they all back down. I'm not asking for a relationship, just a one night/day stand and I'm shocked that so many men that claim to want to do this back out, delete their accounts, or just ignore my inquiry into their feelings on it. I guess I finally realized just a sliver what women go through when dealing with men!

I've conquered many things since cross dressing, but I still have many doors to open. A giant one is admitting this to my spouse, but I know this will not end well based on what I know of her over the years. The other is to take the leap forward to be more out in public, and of course allowing Deanna to soil her oats and find her sexual freedom.

~D~