Paths not taken as a boy that I might have taken as a girl

[AllenJames]

Sleep was hard to come by last night after too much coffee at a day long conference on the road. Back in the hotel trying to sleep (wearing black lace VS pjs), my mind wandered to the sound of some nice jazz (trying to sleep) and I found myself wondering what if I had actually been born a girl. Assuming I would have had much the same tastes, etc,. I would have been a midwestern girl with a taste for East Coast styles over really sexy lingerie, I certainly would have worn more shorts and exposed as much skin as possible (and made the most of whatever breasts I might have had!). (I probably also would have smoked seeking that "sophisticated" air). I would also have been more daring about same sex play than I was as a boy because it seemed less dangerous, but all of those sleepovers, etc, joined a sorority where I did not join a fraternity. Certainly would have practised kissing and perhaps, more - as I boy I loved going down on girls as well as fingering so that would probably have been very much of interest. I also like have my male nipples played with so I can only guess what kind of fun I might have been up for as a girl with breasts! That led to picturing myself as a girl making out with and even having sex with my girlfriends and even girls i wished had been girlfriends. Needless to say, I woke up harder than I have in a long time. Would I have fooled around with my brother? I'm not sure, but I had some boy cousins - and later some female step cousins and I might well have fooled around with both! This may keep me up and awake on future nights now.

 

[Marty Fisher]

Sleep was hard to come by last night after too much coffee at a day long conference on the road. Back in the hotel trying to sleep (wearing black lace VS pjs), my mind wandered to the sound of some nice jazz (trying to sleep) and I found myself wondering what if I had actually been born a girl. Assuming I would have had much the same tastes, etc,. I would have been a midwestern girl with a taste for East Coast styles over really sexy lingerie, I certainly would have worn more shorts and exposed as much skin as possible (and made the most of whatever breasts I might have had!). (I probably also would have smoked seeking that "sophisticated" air). I would also have been more daring about same sex play than I was as a boy because it seemed less dangerous, but all of those sleepovers, etc, joined a sorority where I did not join a fraternity. Certainly would have practised kissing and perhaps, more - as I boy I loved going down on girls as well as fingering so that would probably have been very much of interest. I also like have my male nipples played with so I can only guess what kind of fun I might have been up for as a girl with breasts! That led to picturing myself as a girl making out with and even having sex with my girlfriends and even girls i wished had been girlfriends. Needless to say, I woke up harder than I have in a long time. Would I have fooled around with my brother? I'm not sure, but I had some boy cousins - and later some female step cousins and I might well have fooled around with both! This may keep me up and awake on future nights now.

Mmmmmm, I simply LOVE this and think about the same often.....it's too bad that being BOTH isn't the norm! Think about that - why shouldn't it be?!?

http://static.boredpanda.com/blog/wp-content/uploads/2015/08/fb_thumb_55d59818491d2.jpg
https://i.ytimg.com/vi/n-ViSOO91CY/maxresdefault.jpg
https://i.pinimg.com/originals/24/9c/85/249c857e5475a32278db5c67bb2e2106.jpg

 

[AllenJames]

Nice....but

Great pics and being a boi as I am I love that they can look that good, makes me wish I were starting out now! But the idea of a life exploring female sexuality and especially bisexuality really had me going last night - and I suspect it will return again and again! Thanks for sharing the pics!

 

[Justfantasies]

If I had been a girl, I would have been really, really slutty

 

[jackstud]

We like that

 

[oggbashan]

I have a cousin that looks so much like me that she could be taken for my sister.

She is also built like me, tall and heavy with massive feet. While I played Rugby and Australian Rules she played hockey and lacrosse. Both of us were players that other people were frightened of challenging.

She had to dress in a way that suited her size and eventually found a boyfriend who became her husband that was even taller and heavier than her - not easy.

On a dance floor, like on a sports field, both of us are people to avoid for fear of being crushed or trampled particularly with appropriate size partners. Until she met her boyfriend I was her preferred dance partner, not because we were romantically attached but because I was the only person she knew who could lead her in a dance.

Her son and daughter are of similar build but even larger. The son has no problems with women of normal size but the daughter at six feet three and 220 pounds of muscular build has found, like her mother, that there are very few men large enough to be suitable partners - except her brother and similar sized male cousins.

Being a very large woman isn't wonderful.

 

[SissySalina]

sissy does not wonder, at this point in life being able to be a sissy is all that could be dreamt about. If it had been through life then things would be much different and could not say that the enjoyment would be there now. Certainly life would have been much different.

 

[AllenJames]

Of Course

Being a very large woman isn't wonderful.

Having one longtime woman friend who must cope with that as well as a transgender woman who must deal with that I don't doubt it. Of course, if I were born a woman I would probably be a bit closer to my mother in size and shape - as I noted, probably a rather healthy midwestern girl. But the possibilities remain fascinating.

 

[4yourpleasureiam]

Mmmmmm, I simply LOVE this and think about the same often.....it's too bad that being BOTH isn't the norm! Think about that - why shouldn't it be?!?

http://static.boredpanda.com/blog/wp-content/uploads/2015/08/fb_thumb_55d59818491d2.jpg
https://i.ytimg.com/vi/n-ViSOO91CY/maxresdefault.jpg
https://i.pinimg.com/originals/24/9c/85/249c857e5475a32278db5c67bb2e2106.jpg

Oh I wished I had played with makeup when I was younger. I to would have been a slut and I hope the boys would have liked me.

 

[BrightShinyGirl]

I sometimes wonder the opposite — what would I be like if I’d been born a boy? I grew up with three brothers so it’s not too hard to imagine. I’d probably be tall, with a broad hairy chest and a big, black beard.

The freedom would be exhilarating—not having to pay so much attention to my personal safety. If I wanted to go for a long walk in an unfamiliar neighborhood I could just do it with worrying about being harassed or attacked.

I’m fascinated with guys’ muscles. If I was a guy I’d volunteer to carry things around all the time just for the thrill of it. You need that pickle jar opened? Allow me! Being able to hold a woman down during sex must be such a huge power rush. Being able to pin her arms over her head so she can’t move no matter how hard she tries—I’m really curious what that kind of effortless dominance would feel like.

I’m not sure how I’d feel about having a cock. It seems so awkward and ungainly having it hanging there. And erections look uncomfortable. I mean, I know they’re not, they’re actually pleasurable, but having something so hard and sensitive jutting out like that seems like a recipe for disaster.

Cumming however ... that looks like fun. If I was a guy I’d want to cover my partner in cum. Just pump it everywhere—in her hair, on her tits, in her pussy. I’d probably jack off all the time just to watch it shoot out.

 

[Whispor]

Cumming however ... that looks like fun. If I was a guy I’d want to cover my partner in cum. Just pump it everywhere—in her hair, on her tits, in her pussy. I’d probably jack off all the time just to watch it shoot out.

Trust me - I'm 47 and watching my own cum shoot out still fascinates me. It will never get old, and will never cease being fun.

 

[AllenJames]

Delicious

If I had been a girl, I would have been really, really slutty

Me, too - wouldn't it be fun!

 

[AllenJames]

Distaff

I sometimes wonder the opposite — what would I be like if I’d been born a boy? I grew up with three brothers so it’s not too hard to imagine. I’d probably be tall, with a broad hairy chest and a big, black beard.

The freedom would be exhilarating—not having to pay so much attention to my personal safety. If I wanted to go for a long walk in an unfamiliar neighborhood I could just do it with worrying about being harassed or attacked.

I’m fascinated with guys’ muscles. If I was a guy I’d volunteer to carry things around all the time just for the thrill of it. You need that pickle jar opened? Allow me! Being able to hold a woman down during sex must be such a huge power rush. Being able to pin her arms over her head so she can’t move no matter how hard she tries—I’m really curious what that kind of effortless dominance would feel like.

I’m not sure how I’d feel about having a cock. It seems so awkward and ungainly having it hanging there. And erections look uncomfortable. I mean, I know they’re not, they’re actually pleasurable, but having something so hard and sensitive jutting out like that seems like a recipe for disaster.

Cumming however ... that looks like fun. If I was a guy I’d want to cover my partner in cum. Just pump it everywhere—in her hair, on her tits, in her pussy. I’d probably jack off all the time just to watch it shoot out.

Wow, great comments - interesting to hear it talked about from the other side, Thanks!

 

[AllenJames]

Still thinking

We like that

I do, too - it is very interesting to imagine having lesbian sex with former girlfriends and wives - and speculating on which of my male friends I might have seduced or allowed to seduce me (poor boys thinking it was all their idea). And who hasn't enjoyed those fantasies about life in a lesbian sorority dorm? Then, older, moving to say a big city on the Coast - and becoming a sophisticat and eventually perhaps even a cougar?

 

[JulieAnn42]

Like Bright Shiny Girl, I have always been fascinated by men's junk just hanging out there. I would not want it though.

 

[LauraWilling]

I sometimes wonder the opposite — what would I be like if I’d been born a boy? I grew up with three brothers so it’s not too hard to imagine. I’d probably be tall, with a broad hairy chest and a big, black beard.

The freedom would be exhilarating—not having to pay so much attention to my personal safety. If I wanted to go for a long walk in an unfamiliar neighborhood I could just do it with worrying about being harassed or attacked.

I’m fascinated with guys’ muscles. If I was a guy I’d volunteer to carry things around all the time just for the thrill of it. You need that pickle jar opened? Allow me! Being able to hold a woman down during sex must be such a huge power rush. Being able to pin her arms over her head so she can’t move no matter how hard she tries—I’m really curious what that kind of effortless dominance would feel like.

I’m not sure how I’d feel about having a cock. It seems so awkward and ungainly having it hanging there. And erections look uncomfortable. I mean, I know they’re not, they’re actually pleasurable, but having something so hard and sensitive jutting out like that seems like a recipe for disaster.

Cumming however ... that looks like fun. If I was a guy I’d want to cover my partner in cum. Just pump it everywhere—in her hair, on her tits, in her pussy. I’d probably jack off all the time just to watch it shoot out.

OMG! You said this so well! I have wondered about these exact same things many times myself. I would ad that I would like knowing how a man can spot us submissive types so easily. Even in a crowd. Thsi has happened to me many times and has always been a mystery how men do this.

 

[4yourpleasureiam]

I sometimes wonder the opposite — what would I be like if I’d been born a boy? I grew up with three brothers so it’s not too hard to imagine. I’d probably be tall, with a broad hairy chest and a big, black beard.

The freedom would be exhilarating—not having to pay so much attention to my personal safety. If I wanted to go for a long walk in an unfamiliar neighborhood I could just do it with worrying about being harassed or attacked.

I’m fascinated with guys’ muscles. If I was a guy I’d volunteer to carry things around all the time just for the thrill of it. You need that pickle jar opened? Allow me! Being able to hold a woman down during sex must be such a huge power rush. Being able to pin her arms over her head so she can’t move no matter how hard she tries—I’m really curious what that kind of effortless dominance would feel like.

I’m not sure how I’d feel about having a cock. It seems so awkward and ungainly having it hanging there. And erections look uncomfortable. I mean, I know they’re not, they’re actually pleasurable, but having something so hard and sensitive jutting out like that seems like a recipe for disaster.

Cumming however ... that looks like fun. If I was a guy I’d want to cover my partner in cum. Just pump it everywhere—in her hair, on her tits, in her pussy. I’d probably jack off all the time just to watch it shoot out.

I can very well dream of you being my guy and I your girl and you doing as you please with me. Oh My Yes.

 

[goodsonformom]

I would have been less of a slut than I was.......

I think as a boy it was safer in someways, more plausible excuses, and societal acceptance, sadly. I think the fun part of being a girl would to have had the ability to flirt. I would have loved to be in a feminine role and flirt with my dad or uncles. I would have loved seeing their response....

 

[KimGordon67]

Huh ... I'd completely forgotten about this, but this thread reminded me - I used to have an online partner who was totally up for exploring all sorts of things. One of the great things about cybersex, obviously, is that you can 'think yourself out of your body' ... somehow a few times - not often, but more than once - we'd end up sliding into me having a cock and him having a pussy. We were still 'us', just with different genitals. It was really interesting to get into the mindset of being the person who 'penetrated', rather than 'was penetrated', if that makes sense.
Thanks ... I'd completely forgotten about that, and it's a really great memory to have again.

 

[OrLaTime]

Thus my interest in good strapons that let women explore the other side
By good, I mean handsfree with good feedback that gets them to their orgasms first

Batgirl would have such toys for sure

 

[AlexBailey]

I would have been a rough and tumble tomboy who could polish up well and be fun in the sack with girls and guys.

As a kid I liked getting dirty with the guys but I liked playing with the girls too, I was always jealous of the sleepovers the girls would have.

I would have been into gymnastics and cheerleading. In highschool I hung out with the cheerleaders but I wasn't into boy's team sports like football or basketball, I went to the prom with the squad captain and was always silently wishing I could trade places with her.

I work in a field with few women but the ones that are in it are mostly tomboy types, or at least really fit and very good at their work. I would have probably had the same career.

I probably would have been a slut sometimes but I would have been careful about pregnancy and I would have eventually been a mom.

The safety issues of being female are very real. I'm sure it would have changed how free I've always been about exploring by myself. I've definitely been crossdressed in situations that could be dangerous if I encountered the wrong person and I've been groped by random strangers at concerts who mistook me for I girl when I wasn't even cross dressed, so I know how uncomfortable that can be. I'm not a very big guy but I would be on the large size for a woman. Size 12-14, XL-XXL, 5'8" ,170lbs.

My sister is pretty, just a bit shorter, she has modestly sized breasts, but I probably would have been quite a bit prettier and would have stayed in better shape, so I probably would have been pretty hot.

I would have had a similar world view to what I have now. My first serious relationship was with a girl who, besides when she was with me, was and always has been a lesbian. We hung out with a big pack of dykes, (that's now they referred to themselves) the whole time we were together. I was accepted for the most part. I remember going to lesbian events with all of our friends and being inspected and watched by a bunch of self appointed butch security guards who finally publicly gave me their stamp of approval. Lol.

I may have been a mom and raised kids with a wife, though I would still be bisexual. I don't think my real world wife would have been with me if I were a girl. Maybe she would have been my friend and l could have been more promiscuous.

I wonder.

 

[AlexBailey]

AllenJames, your avatar is really cute!

 

[stargame]

Very cute body.

 

[AllenJames]

Love this thread

Huh ... I'd completely forgotten about this, but this thread reminded me - I used to have an online partner who was totally up for exploring all sorts of things. One of the great things about cybersex, obviously, is that you can 'think yourself out of your body' ... somehow a few times - not often, but more than once - we'd end up sliding into me having a cock and him having a pussy. We were still 'us', just with different genitals. It was really interesting to get into the mindset of being the person who 'penetrated', rather than 'was penetrated', if that makes sense.
Thanks ... I'd completely forgotten about that, and it's a really great memory to have again.

In my early days online playing, I did have one experience in which I played totally female with a male online partner - LOVED IT!!!!

But I realized at the end that he hadn't realized that I wasn't a gg - and he got very upset and so did I. Changed my profile to make it clearer and was more careful - but still love playing that role from time to time with a willing partner - with my toys to help out on my end/