Interview with Penny Ollie

This is the first in a series of interviews with crossdressers, this time we meet Penny Ollie who is from the East of England




1.How do you describe yourself, (crossdresser, transvestite, trans gender) ?

I like to think of myself as trans-gender, but in reality I am a cross dresser, as I have not had any hormone treatment or surgical reassignment. I do not like describing myself as a transvestite, as this is an old term, which I believe has negative connotations, based around past prejudices.

2. How long have you been crossdressing?

I have been cross dressing from my earliest memories. I can recall that my sister and I slept in the same bed in infancy and we often exchanged pyjamas secretly, until my strict father caught us. I was the only one blamed and punished. We were then put in separate  beds. 
Shortly after this, at around six years of age, we went on holiday to Torquay. I can remember the landlady in the hotel, putting a red ribbon in my hair and said “you look more like a pretty girl than a boy.”  

3. Acceptance was for me, the turning point, once I had accepted who I was my life changed. What about you? When did acceptance come to you, how did it change your life and outlook regarding crossdressing?

Throughout my adult life I felt ashamed of cross dressing and the associated desires and attempted to cure myself, with only temporary success. However, about eight years ago, we had a charity event at work, where a handful of us dressed as women for a day. The girls in the office brought in outfits and applied our makeup. They even had some six inch stilettos that fitted me perfectly. My colleagues said I really looked like a woman and the ladies in the office kept giving me compliments and taking photos. I really enjoyed the day. I kept reflecting on the event and how good I had felt psychologically. Shortly afterwards I decided  to accept who I was and to embrace my suppressed femininity, I then began to do my own complete makeovers. I have moved on quite a bit since then, buying a full wardrobe of outfits and frequently going out in public as Penny. 

4. Have you ever considered transition? Would you consider it in the future?

When I was around 17, I went through a difficult period of puberty. My mother had died and my father was strict and unemotional. I found cross dressing was a means of escape from a difficult world. I felt I wanted to become a women through surgical reassignment. However being young, I had no idea how to start on this path and little information was readily available, as the internet was decades away. Eventually my life moved on, I married and was busy raising a large family and pursuing a successful career, so these thoughts just faded away. I am now quite happy in my current state and having a full physical transition would raise too many complications into my life

5. You seem very confident when dressed, but how do you really feel?

I feel immensely confident when I am Penny. I feel she is my hidden natural self and has a strong female personality of her own.

6. Have you been out and about? If so where? (no specific locations) 

I often go out in public as Penny, mainly shopping for lingerie and women’s clothes etc. I have travelled on busy trains on several occasions and also go for walks into the countryside and to beauty spots.

7. How do you feel when you've been out?

Going out in public as Penny meets a deep inbuilt psychological need. I feel so complete and am left with a wonderful  feeling of satisfaction. 

8. Do you have a favourite outfit? Describe it and explain why you like it so much.

It is difficult to pick out one outfit. I like to vary my themes from an everyday girl to a classy lady. I love my collection of lingerie. However, if I really had to choose one, it would be my white pussy bow blouse and tight fitting pink midi skirt, with matching pink stiletto heels and pearls. I think this is a very classy outfit. My second choice  would be my short, black, body hugging cocktail dress. This is a very sexy outfit and shows my long legs to best effect. 

9. Us girls love heels, do you have a favourite pair? 

I tend to wear my black 5 inch stilettos the most, so these are probably my favourites, but I do love my whole collection. I tend to wear lower heels when I go shopping, as these are easier to get around in. Large stiletto heels are not normally worn by many women going out and about. 

10. What are your thoughts on 'Passing'?

I think I pass off as a woman successfully. 
I have been approached by men on several occasions who have tried to chat me up. I  have also had compliments from genetic ladies on the clothes I wear. I am not quite so confident with my voice, as I am with my appearance. Having said that, I have  had conversations with check out ladies and ordered coffee in several cafes without any difficulties. I can speak in a feminine voice for short conversations, but need to continue to practice and develop it further.

I am not overtly concerned if I was suspected. It is unlikely anyone would be motivated to say anything. 

11. Have you ever 'Purged' if so how did you feel after?

I like my clothes too much to purge them. I have read many accounts of T-girls purging themselves of hundreds of pounds of clothing and then regretting this and starting all over again. I can understand fully why they would do this, but I decided never to be tempted to do so myself.

12. Would you like to live full time as a woman?

I would like to be able to dress as I woman whenever I wished, without any constraints. This would often be 24/7. However, I do not think I would want to entirely abandon my male mode, which I also enjoy.

13. Can you ever stop?

I have come to realise I can never stop, so I am now enjoying the journey.

14. Have you or would you use a 'dressing/makeup' service? 

No, I am unlikely to ever use a dressing up service. I like to do my own make over.  I love transforming myself and this is part of the satisfaction I gain from crossdressing.

15. Who knows about your crossdressing?

The only people who  know about my cross dressing are my on-line friends. My wife suspects, but seems to turn a blind eye. The lady next door has told my wife I am either a transvestite or having an affair, as she has seen a women drive off in my car.

16. If you could have one wish, what would it be?

To cross dress whenever I want to. 

17. Where do you see your life going from here?

I intend  continue to go out in public and do even more activities as Penny. This might include, meeting other T-girls I trust socially and potentially going to a T-girl event. 


I would like to thank Penny for taking the time and trouble to answer my questions.
Copyright photograph curtesy of Penny Ollie.

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