All Blog Entries

Okay, so Saturday night I go home and sleep in my own bed, and dont come back until Monday. New week, new shenanigans. I hop back on grindr , look around and see my next target. Middle aged guy, starting to lose his hair. I started chatting him up. I asked if he wanted to come by...........he was like

"ewwwwwwwwww, you are too girly, you are so girly you probably smell like a vagina, oh god no, I can't even , ughhhhhhhh"

Well, to be fair, I think my perfume was eau de coochie or something like that. I wasn't sure if I should take it as a compliment or not. I am one of those, I take my dressing up seriously, as in, I work hard on it. Even though I will never pass, i feel good being as feminine as I can.

I moved on, chatted with a bunch of people, it was all 20 somethings wanting to come over and tear me up. Well, that didnt sound fun so i gave up for the night.

The next night after getting dressed, i decided, I want a sprite, but damn, I am wearing a miniskirt, I said screw it and went to the vending machine anyways. While I am getting my soda, I feel a hand on my back and a head near my hair, this creepy guy says

"Gee, I like that ass, and you smell so nice, would you like too........."

At this point I turned around and used my guy voice and asked, "Are you wanting me to shove my cock up your ass"

That guy could have beaten jessee Ownes in a foot race he left so quick. I got back tot he room and found a promising candidate. Everything looked good, invited him over.

Turns out, he was into no touching, we just jerk ourselves off in front of each other, this week was not starting good.

After he left, I went back on, there was a guy who only wanted to come over and blow me, so I let him. He was so happy to do it, I almost felt bad cumming.

But, I did then went to bed.

Next day, I am going through the lobby and a guy asks me if I was an escort, I was flattered and insulted at the same time. Later, I went over to his room and asked him how much he would pay, needless to say, I am not a $50 whore, I want at least $99.99.

One thing led to another , he felt bad and brought over some drinks. We started talking, me asking if he was gay or bi.............nope 100% hetero. Then why did you hit on me ?

He is of the opinion if a guy is wearing a dress, it is not same sex sex. I will say he was a very caring, slow and considerate lover, but oral, nope, he wasn't doing that at all

So, night two comes around. Same thing with people asking questions and chatting and I am like, wanna come over. Sure I had sex the day before, but, for me, I only got gas station sex.............self serve pump your own. All these guys just seemed to want to have chat sex and I am like,
"I need a cocksucker stat.........50 mg of tequila and some kneepads immediately"

One guy was being real pushy, almost demanding to come over right then, tell tale sign of something not good. Plus he made comments about smacking my ass and sillyness, sorry dude, this is not a porno.

Eventually I chose someone and he comes over, walks through the door and gives me that up and down look, I should have been insulted, but honestly, I started getting a boner. So we laid down on the bed and pro-ceeded to start making out.

Guys, I now know why girls always said I was the best kisser. Let me give you a hint, your tongue is not an assault vehicle, you dont have to shove it everywhere like you are a labrador or something, a little technique , using it sparingly works wonders. Sadly, i find this in most guys, I may do video on how to kiss properly, it seems to be a lost art.

Anyways, he was feeling me up, yeah this is going better already. We get his pants off and he is like 5.5 inches and thick. I got to work on it for about 10 minutes, then he flipped me over, I was very concerned he was gonna try and ram that cock into me un-lubed, but, instead he went to work with his tongue. I honestly did not know a tongue could go that far in.

This goes on for a while, then I felt like sucking some more, we are sort of in a 69 position with me on bottom and he is fucking my face, all of a sudden, no warning (usually you feel the slight throbbing) he came like crazy. Turns out he is one of those sensitive guys that feels it for like 10 minutes. Once he settled down, he was kind enough to return the favor.

So , once again, the awkward part of, he we had sex, time to go now. So he got dressed, stopped at the door and said thank you, gave me a kiss and left. End of it right ?

Noooooooooooooooooo, PM's start the next day, how long am I in town, when can he see me again, last night was very special. I did the play it off, I am leaving that night, not back for a few weeks, blah blah blah. Then I get the poem expressing his love for me.

Shit, I mean, do I need to change perfumes or something, what is in the one I bought..................wowwwwwwwww.

He is still stalking me on grindr when he sees me on of when we can get together, he has already told his ex wife about us.

I thought, huh, my luck is being weird, no hook ups for the rest of the week.

Well, for the past month, I have been stuck in hotels for work. So, I decided to , how can I say this delicately, let my inner whore out. So, I went on Grindr, and Silver Daddies thinking, some casual sex with no strings attached will be easy, boy was I wrong..............so, I am going to share the past 4 weeks with ya all.

First night in the hotel, I took my time got dressed, nothing major, a burgundy dress past my knees. Sat with a glass of wine and set up my grindr. Like 10 minutes later I had 9 pm's. Well, damn, now I feel good about myself. 2 or 3 were guys testing the waters, 1 was a very confused kid, and the rest started off with dick pic's.

They all had the same question, you like ?

Guess what skippy, I am 54 years old, I am a former combat medic and paramedic, I have seen a ton of penises in my life, yours aint special. But, I had set up a rule for myself, anyone that greets me with a penis, I block right away. At least say hello, here's my cock, you know, proper manners.

Well, the one I chose that night was this scared younger guy (I felt like such a cougar). He was telling me that one of me has been his fantasy, he has never done this before. Hmmmmmm, well, being a fantasy is kind of cool, I have never been an object of fantasy before.

Oh wait, does that make me objectified ? awwww screw it, I liked it.

So he comes over, we sit down on the bed, he was shaking, I mean visibly shaking. I am thinking if I touch his dick through his pants he would cum. He starts mumbling nonsense trying to sound cool, so, I am like

"Look, why dont you run your hand over my stockings, see how that feels " I could see him getting a boner in his pants. So I reached out and he made sounds like I thought he was gonna cry with fear. Yeah, I know, but I was enjoying the sense of power and sexuality.

It was like I was Crossdresser man, master of the erection (old he man joke).

So, I got his cock out and was stroking it, this thing was hard. He is still trying to say sexy things to me and be cool, but it is just sounding bad. I stroked it for a while and used my best sultry voice to speak with him, finally, screw it, i went down on him and he went stiff all over, I mean like someone having a seizure or an exorcisiscm or something.

He had no clue what to do. He was about 4.5 inches with respectable girth, so, I thought why not, handed him a condom. I asked what position he wanted he was like

"Can you just get on top of me and put it in"..............sure, we did that for a minute. he was grabbing my tits, I don't think he even realized they were silicone. Then he wanted to try doggy style, so he got behind me and started going to town for about a minute and a half and then I heard the unmistakeable uhhhhhhhh sound and it was over.

Hey, I give him an A+ for being enthusiastic though. Then he sits down and starts whimpering how sorry he is it didnt last longer and he doesnt hink he pleased me. So, being the nice girl I assured him of his manhood, and complimented how thick it was and how he used it like someone twice his age.

So, he gets dressed and is ready to leave, I am walking him to the door, he turns, hugs me, kisses me on the cheek and says

"I will never forget you, I want you to always be a part of my life"

Okay, that didnt go as planned, this is not good. I suggested he go home, patch things up with his girlfriend and move on with life. He responded, am I gay.

Well, shit-balls, now instead of being a cheap tramp for the nigh, I have to be a counselor. I am like, well, do you still like Vagina, do you still like boobs, they way a girl smells, their soft skin ?

Okay, then you may be bi, I wouldnt worry about it, this could be a one time thing................so he finally left.

Except I kept getting PM's for 2 weeks, how he misses me, wants to go on a real date etc etc etc, meet his parents. I had to jsut block him at that point.

So, I don't cruise, I don't generally do blow n go, and I generally don't do a one night stand. But a few days in a hotel, why not. I had an interaction in the hotel with a guy asking if I was an escort, I made some jokes and asked how much I was worth. Well, he felt bad and came down with some wine. After the first bottle and we were talking, one thing led to another.

I had asked him if he had ever been with a guy, as I thought he was hitting on me.
He said no, no way in hell, I am not gay..............hmmmmmm,, okay.
So I asked, but you were wondering if I was an escort, I kind of got the opinion you were interested.
He said yeah, a CD or Trans, but I don't do guys. I suggested he was Bi then ?

Nope he is 100% heterosexual, he just likes CD's and Trans

I didn't get the opinion he was homophobic or anything, but that he truly believed that there was some kind of magic that made me female when wearing a dress. Before you ask, yes, we did end up having sex. Honestly, it was very good. He was careful to only use female pro nouns, and every body part he called by a female name. Again,I dont think this was for my benefit, but his.

I put myself on grindr, just for fun, only met one person,but, I can tell you, I get a lot of texts or PM's or whatever you call it. I dont think its because I am so passable, I am not, and there are some seriously hot CD's on there, I mean wow. I think it's more of a gateway for some men.

They can still convince themselves they are not gay or BI, it's like a protection circuit for them.

I guess that makes me a gateway drug

But I do find it interesting how hard they work to consider themselves straight

The number 1 question I get asked, "How do you get clothes"
Number two question " How do you keep your life quiet"
Third questions always revolves around "Isnt this just a way for you tog et more sex"

Well, second question is easiest to answer, some people know, some don't. As I don't live my entire life crossdressed , there is not a need for the world to know my private life. I see this as no different than I don't know if my neighbors do it missionary or doggy style, not everything in life has to be shared with everyone.
As my car is in the garage, when I go out dressed, my windows are tinted, I just pull out, and my neighbors have no clue.
I keep my personal life seperate from work, so no issues there.
When I did live with others, I had a cabinet that was securely locked. I told everyone I secure my guns when not in use, which was true, but, there were clothes in there also.

Third question, "isnt this just a way to get more sex". Yes, in the beginning there was a highly sexual component to dressing, the arousal and naughty aspect. These days, yes, I do get more exciteable when dressed, but, it is also now a part of me and my personality, and the majority of the time when dressed en femme, I am not getting any, just lounging around the house. I know for many, it is all about sex, but, for others it's much more than that. When dressed it doesn't mean we are just looking for sex. Just like the rest of the world, we are all individuals

Now, as for the clothes. There are many ways to get clothing and still be highly discreet. Same with make up and other things. If you go online, there are actually size charts to help you know your female size. Now, the problem is, they are not 100% accurate, because men are built different, just a fact. When you measure your waist and hips there is a little wiggle room on getting the correct size................so, some trial and error.

The other issue many of us have, we see something that looks hot, and we see ourselves in it, then we try it on and huge disappointment. For us, it's a new feeling, genetic women have been dealing with it all their lives and understand how to work around it, so, be prepared to accept, you may not get to wear everything you want (depending on your desires). Although I have met some "ladies" that holy crap everything looks hot on them.

For me, i can wear a size 2 pants, but a 4 dress depending on the make.So how to get your clothes and make up easily without fear.

Well, for one thing, you can order online, download the walmart app, park in a designated spot and they bring it out to you. The negative, you don't get to walk around and touch and see things, the positive it removes the fear factor, I suggest ordering cheaper basic items at first to get a feel for the different cuts and way things fit.

Another one I have utilized is the WISH app, everything online shipped to your house. The problem is, it is usually very bad quality and you don't really save money with the shipping fees, but I have gotten some really cool stuff. the other negative, you sometimes wait 8 weeks.

Last easy one is Amazon, fast shipping, very discreet, no problems and easy returns...........but if you live with others, there is a chance they will open your package. Walmart is my favorite for the pricing and easy of getting things. I usually have a shopping list on my computer, then when ready hit purchase.

you would be surprised at the sexy stuff walmrt actually sells

And... I got caught. My brother and I had been getting it on and prior to our mom busting into our room, I'd been under him and feeling good and dreamy as he fucked me and more so when he unloaded his balls into me. We changed places and i was in him and it felt good and as it always did and... "What the hell are you doing?"

Oh, shit. I knew I was going to be beaten badly... and that never happened. I got a lecture about it that still stings when I think about it today. After I got reamed out for it? I had two thoughts: The first was that if she had busted in five minutes early, she would have caught him fucking me and the second was, even if she had, she still would have blamed me for it since I was the oldest and should know better. And I did... I just knew "better" than she did but something else occurred to me: I didn't get the horrible beating that I expected to get... because she knew and chose that moment to put a stop to it.

Which, um, didn't work. She went back to bed... and we went right back to having sex.

Sigh. Guys can be so... weird about getting dick. I understand their fears. Why they hesitate. How it can mess with their minds and in ways they may not be aware of. My brother had noticed it and mentioned it to me one day because a guy he had sex with was very weird about it. He asked why guys had to be so fucked up in the head over something they fucking knew they wanted to do and I told him that that the answer wasn't an easy one - but a lot of it is all about us not having sex like this and how forbidden it was. He just shrugged and said, "Whatever. Let me get that dick."

I'm fucking him and he says, "I fucking hate you... but I love it when we do this." I knew how he felt. It kinda didn't make sense but we both accepted it for what it was. Two days before his girlfriend murdered him, we'd had sex. It was as good as it'd always been. He had said, "You know, we've been doing this for a long time and there's no other dude I'd rather have sex with than doing it with you." It's... weird that the best memories I have of him are the ones where we were having a field day with each other. Finally understanding that, sure, we really did hate each other but by having sex, we did find a way to get along with each other and that was what had more importance. Immoral? Sure it was. So what?

Today, society is so fucked up in the head about boys being boys and the many ways they can be and it makes me scratch my head and wonder if they really understand what this is about... or, if it's really just us - as a whole - being very prudish about sex and how it can really be done and, yes, between men - and being gay doesn't have a damned thing to do with it. Some being very weird about how I learned all of what I know about this. Changing the minds of a lot of guys and showing them a truth that I learned so very long ago:

Nothing really wrong with getting some dick... because it's sex. Anything else is gravy. Many fears are unwarranted and imagined but many more are very real... but can be dealt with. The only safe sex is not having sex... and the only abnormal sex is not having sex at all. You learn to be smart about it and you learn not to fear it; you learn to be safe - that's what condoms are for. You learn to not let your fears make you foolish. Timid. Allow it to suppress that natural desire you feel to get some dick and to give it. Making it harder than it has to be. Letting the social bullshit fuck with your head when you should be paying more attention to what you know you want to do but keep finding reasons not to. I understand it because I grew up with it and in every way imaginable. With adults who knew better. With my friends and how we learned from each other. Yes, incest, too. Learning that as long as nothing went wrong - and you didn't get caught - it's just... sex with someone you care about or love or, yeah, you can't stand but when you're having sex with them, well, it's all good. Just boys being boys and being unafraid to be a boy.

All along the way, showing and teaching other guys what I know about this. Learning to understand their fears which was mostly about becoming gay more than anything else. Sucking them off and seeing that moment when they realize that they were afraid for no reason at all. Being told that I suck dick better than women do but that didn't matter to me as much as hearing them say, "It wasn't as bad as I thought it would be!" or "I don't know what I was afraid of..." and "I don't know why I didn't do this before now!"

And being able to understand why they didn't. Why they thought it was bad. What they were afraid of. Learned to better understand myself by helping them understand themselves and that sex, well, it's just sex. It can mean more than that and that's okay. Seeing so many guys at their wit's end because they need to have sex and women weren't trying to give it to them and knowing that I can make them feel good... if they're not afraid to have sex with me.

Falling in love with a gay man. Shit - didn't see that coming! But it did and I learned even more stuff about boys being boys and why they were the boys that they were. God, I loved him so much and in doing so, I learned some important shit about love, like, it didn't matter who you loved as long as you loved. Having sex with him. Seeing the joy in him as he'd suck my dick. The way he clung to me when I fucked him. It didn't matter if we were "good" or not because being in love made the sex better. He was so... girly in bed that I'd often forget that I was having sex with a guy.

Sex is a very powerful thing and I'd learned that from the first time I tasted dick. I knew. I understood. I'd tell people how I got to love dick... and they would feel sorry for me. Saying I was abused. Yeah, technically, I was... but I never felt abused and when they'd tell me how sorry they were I would say, "I'm not - I'm glad that it happened and if I could thank the man, I would because what he did freed me and taught me some very important stuff about sex... and life."

And yes - if I could go back in time and do it all over again, I wouldn't change a thing. Like, I couldn't stand the stupid game my cousin would want to play so we could have sex but I'd grow up and understand why he chose this way to do what he wanted us to do because we were more like brothers than cousins and I was the brother he didn't have. Crazy game... but the sex was very, very good. That sense of pride when he busted his first nut with me and how good it tasted. Calming his fears about it - and because I remember how scared I was when I busted my first nut at the ripe old age of nine.

Other cousins, both male and female and close enough to be illegal in most places... but that's not what mattered. Having sex with them. Showing affection because we were related. Vacationing with a brother and sister cousin who were more shameless about having sex with each other than I could ever be... and having sex with both of them, one-on-one and in a threesome and understanding that at the very root of this very incestuous thing was... it's just sex. No harm, no foul. Learning from them that living on a farm and tending animals taught them that sex was normal and natural and understanding the same thing I did when having sex with my own brother and sister: If you can't have sex with them, who can you really have sex with? Who knows you better?

And, importantly, it ain't illegal unless you get caught.

Being a teenager and learning that there were a lot of adult men who wanted to have sex with me. Pedophilia, they called it. Child abuse, they called it. Yet, I'd have sex with adult men and not ever felt abused at all. Yeah, some "seduced" me but I knew what they were doing and, sometimes, it was funny because I knew, even if they didn't, that all they had to do was just ask me if I wanted to without trying to seduce me. Did that make me a bad person? Eh, sometimes, I felt like I was but, again, I was learning that boys will be boys... even when they're grown-up boys. That some of them liked boys my age was kinda scary - some men were very creepy and I avoided them but if they were kind and all that, sure. I would realize, many years later, that those older men treated me better than the guys my own age would or did.

I understood that forcing someone to do it was very bad. Kid logic said that as long as I wasn't being forced to do anything, it'd be okay. I understood sex in a way my peers didn't. Right or wrong didn't really mean a whole lot and sometimes, it wasn't what you did or who you did it with but why you did it. All the rules made sense... but not really all that much. One day feeling very weird about screwing my sister and her telling me that as long as I didn't get her pregnant, she didn't know what the problem was. We were screwing because we were both very horny but at the root of it, we loved each other, and sex was a way to show that love. Knowing that incest was very, very wrong but also understanding that it's only really wrong if something goes wrong or, yeah, you get caught. Being lovers with my brother who didn't like me all that much - and I didn't like him - but we'd have sex and that was really the only time we got along with each other... and it made sense to me despite the circumstances that made us not like each other.

Getting some dick is just good. One day, I fell into a man's trap; he drugged me, tied me up, and had sex with me. The bad part? The sex was damned good. I still tried to kill him because he fooled me... and that was my fault more than his. The things I was learning about having sex with guys was... deep. Complicated but not really if you got to know why men - and boys - are the way they are about getting their dicks hard and having sex. Having sex with guys who were "more like girls" than they were guys... and not all of them were gay and then learning stuff about guys who were. Not just how they liked to have sex but why they only liked guys. Complicated but not really.

it's a satisfaction that, in a lot of way, cannot be found when having sex with women. You find out what you like and what you don't like. Learning that you don't have to be into a guy in order to have great sex with him. Again, I had a brother who couldn't stand me and I disliked him with a passion; conventional thinking says that you never have sex with someone you don't like but we were the exception to the rule. We could fight like wild animals and later have sex like the fight never happened. Finding it hard to admit that out of all the male lovers I've ever had, he was one of the best ever. Weird stuff... but real-deal, real-life stuff.