General Info

Sissy Phillipa

My name is Phil, but sometimes I go by the name Samantha. I'm from Portsmouth in Hampshire. I'm often Samantha in my head and Phil to everyone else...but sometimes I get to be Samantha on the outside too.

It all started for me when I was about 4 years old. I don't know why, but I had a fascination with my mothers underwear. A particular set of black silky underwear with red lace trim gave me strange feelings whenever I saw them. I also used to play with my sister and her friends back then. One particular day, I was getting dressed up in a lollipop lady's outfit (don't know why that one in particular - it was just there!) sister and her friend were putting finishing touches on me and I was just loving being the centre of attention. I was part of the gang, I belonged (more of which later). The woman from next door who was having tea with my mother commented on me playing dressup with the girls. "You know, he'd make a good little girl wouldn't he?" was the throwaway comment. From then, I started to imagine what it would be like if I WAS a girl. So started early forays into dressing.

I mentioned earlier the feeling of being part of the gang, a belonging. This was a theme that would recurr time and again. I've always been quite a shy person, and found friendships a little difficult, especially at the start. Approaching a girl I liked in my early courting days was always difficult unless accompanied by copious amounts of alcohol. As I grew older, I often craved that sense of belonging with female companionship, however that was a door that became increasingly closed to me as puberty and later the male female divide kicked in. I imagined what it would be like to be a girl again...and how if I were, I could somehow belong to that 'inner sanctum' although this was never to be.

So now, I find myself still dressing, still imagining myself as a girl, sometimes wishing I were, but fully recognising the fact that I am not, nor ever will be. I still seek to belong, but within the acceptance of who I am and what I can achieve. This community, and finding the companionship of others like me is now my comfort, my sense of belonging, my gang!

Latest fantasy

The latest fantasy that I have been daydreaming about is to find an openminded couple. In my imagination, the woman would be in charge (how I love it that way). She would call the shots with both myself and her partner. After dressing appropriately, myself in a suitably sissifying outfit - I am made to caress and suck her partner to hardness whilst at the same time, the woman goes to work on my ass with a strap-on. Before her partner reaches climax, the couple swap position. With the strap-on removed...the woman is now riding my face with her juices flowing everywhere, at the same time her partner is giving me a good pumping in my ass. Of course we all cum at the same time (its my fantasy after all), and then come down from the intensity with some lovely kissing and cuddling.

Would like to meet

Well, you probably get a good idea of how my mind works from whats been written here. I'm keen to meet anyone who is prepared to be friendly and non judgemental. Sexually, I like to be experimental and try new things. I have few limits, but they need to be discussed openly and respected both ways. I'd love to hear from anyone who'd be interested in friendship or more, so don't be shy, say hello x x

Turn Ons

Forced Feminization, Forced Bi, Cuckolding, Femdom, Bondage, DS, Crossdressing, Roleplay, Exhibitionism, Voyeurism, Eating Pussy, Sniffing Panties, Sissydom.

Turn Offs



Bend over boyfriendPorn.


A real eclectic mix

About myself

Physical Profile

Sexual Interests

SissyPhillipa's Photos (3)  (1 - 3 of 3)  
7 years ago
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SissyPhillipa's Favourite Videos (11) (1 - 4 of 11)  
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****** Cuckold
7 years ago
Squirt My Cum
7 years ago
Moms That Cheat
7 years ago
Strap Attack
8 years ago
Sodomia ( 2 )
5 years ago
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All Comments

6 years ago

I love the way your bigcock is sticking out ofthose tiny panties. Mine is doing exactly the same thing

more please!



7 years ago

Hello Sam,love your profile,love your pics !!! I'm glad to be in YOUR gang,hugs kizzy Xxx.

7 years ago

Your cock looks nice in lace

7 years ago

Hi there

SissyPhillipa - Male

Rate ME!

14 votes

Member for 8 years
Sexual orientation: Bi-Sexual
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