Transvestite practices gynecology on inflatable stepdaughter & her friends.

I consider myself to be a part-time cross dresser (the rest of the time, I’m just a hot-blooded horny male.) Some of you may be aware of the special relationship I have with Carolyn, my inflatable stepdaughter. (If you’re not, then that’s another story on another thread.) For the past few weeks it’s been not just Carolyn, but also her friends, who have been providing me with my stimulation.

You see they’re at that age now. The age when they have to start worrying about becoming a woman and the associated visits to the doctor. Of course they’re all a bit worried and nervous by this prospect but Carolyn and I seem to have come to the ultimate solution. To save the embarrassment of visiting the gynecologist, my stepdaughter asked me to help her with her routine examination. Of course, I was only too willing to help, and she trusts me completely, especially since our relationship has recently become much more personal.

Little was I to know that my step-daughter told her friends and it wasn’t long before they were all coming to me for their examinations rather the their own gynecologists. I think the fact that I was dressed as a woman helped ease their nerves a bit. Carolyn’s friends were always very comfortable with the way I dressed and they saw a me as a sort of motherly figure for them – to help them though their change into womanhood. That always seemed to put them at ease.

So this is the story of one of Carolyn’s friends, and her first ‘examination’. When she first came to me she was very shy. She knocked at the door and entered my room. I was immediately awestruck. She had just finished school and was wearing her tight blue T-shirt, short skirt (very short!) and her cute little white ankle socks. Her short blonde hair made her look every bit as innocent as she really was. I gulped as she entered my room and tried to hide my arousal.

It wasn’t easy. From the moment I saw her my cock started to grow inside my silk panties.

But I had to remain professional and push these sexual thoughts to the back of my mind. This wasn’t going to be easy. And my hard cock continued to swell.

I beckoned her in and asked her to sit down on the edge of the examination bed. She stammered, ‘Uhhh, I need a physical examination to get into college, Carolyn said I should come and see you.’ My heart skipped ten beats as I looked at the sweetheart sitting before me. I struggled to maintain my composure as I asked her if she’d had her vagina examined before. She started looking a little nervous and the more scared and nervous she got, the hotter I was getting. I beckoned her close and put my arm round her to help put her at ease.

That first pic is so cute! Looking forward to future story installments.

You're right College_Geek. She is dead pretty isn't she? You can see why I fell in love with her straight away.

Frisky,
I've just been browsing through this thread and your other one along a similar theme. You are kinky - and I LOVE it.
I adore that little short skirt she's wearing. I used to have one just like that when I was younger. I wouldn't fit in it any more though.
Amy

‘I’ve never done this before, what do I have to do?’, she asked shyly as those big blue eyes looked up at me. I told her she had to get undressed so I could examine her fully. ‘How much do I have to take off?’, her trembling voice inquired. I explained she needed to get bare foot, take off her tee and bra and to completely remove her panties. She look absolutely terrified at this and I knew I’d have to take things slowly. I agreed with her that she could keep her clothes on for just a bit longer until she felt comfortable with me. I asked her to lay back on the bed, and I turned to lock the door. When I turned back she was lying down and I was able to sneak a view up her skirt. My cock began to twitch inside my knickers as soon as I caught a glimpse of her white panties under her school skirt.

She looked so vulnerable and sexy, and I could tell she was really nervous. I walked over to her and told her in a calm voice that I would begin the examination, ‘I need you to lay back all the way and rest your arms behind your head for me.’

She lay back and she raised her arms, I could see her young round titties under her top, stand straight up and separate ever so slightly. ‘Good girl’, I encouraged her. ‘Now I’m just going to feel around each breast.

‘Just lay still, Honey’, I told her. Her little tits were amazing and so nice and firm.
‘But doctor, don’t you think like my breasts are just so small and stuff? And I hate my nipples. They stick out so far and most of the time they sort of feel tender a lot’, she softly confessed.

‘Well, let’s just take a quick look at those nipples then’, I responded. With that I began to roll each nipple between my fingers and gently pull them outwards. My penis was now so hard that it was becoming painful

please continue...

Yeah, cummon Frisky, let's see a little more. (remind me what it felt like to be a little girl again) (a long time ago, I know but I don't need reminding of that)

Don't use any sharp instruments there doctor.

By now, I could sense she was relaxing, and becomming comfortable with me touching her. I explained to her that she would have to remove her top to allow me to examine her chest a little better. She reluctantly and slowly pulled up her little cotton T-shirt. Underneath she was wearing nothing but a small white little bra, with pretty colourful bows on the front.

I was once again how shy and vulnerable she looked, and a little embarressed, but that just turned me on even more.

I straddled over her tiny, frail body and sliped my hand underneath the tiny cup of her bra. She let out a little moan as I teased each nipple. 'I'm going to have to pull them a little harder now.' and she really started to moan. 'Oh doctor, please, please, they feel so swollen,' she quietly pleaded. I must confess, I took full advantage of working those hard nips as I finished a very thorough breast exam.

mmmm, you're right Frisky, that is a pretty bra. Maybe we'll get to see more of yourself as well soon?

My own penis is now hard as rock and I’m sure this little girl is fully aware of the effect she’s having on me. I slowly release my throbbing cock from my knickers and she lets out a little surprised gasp as it springs into view. ‘That’s huge’, she says. ‘I’ve never been this close to a real one before’.

I tell her not to be scared and cover her eyes with my hand. I then lift up her little bra and slide my cock underneath. It feels like heaven, the tip of my hard cock nudging between the warm, soft buds of her breasts. I begin to rock back and forth, pushing myself along her tiny cleavage. ‘Is this all part of my breast examination?’, she asks. I explain that it’s all normal procedure for a girl her age and tell her to relax and enjoy the feeling.

Frisky Bunny said:

I tell her not to be scared and cover her eyes with my hand. I then lift up her little bra and slide my cock underneath. It feels like heaven, the tip of my hard cock nudging between the warm, soft buds of her breasts. I begin to rock back and forth, pushing myself along her tiny cleavage. ‘Is this all part of my breast examination?’, she asks. I explain that it’s all normal procedure for a girl her age and tell her to relax and enjoy the feeling.

Click to expand...

mmmm do continue! My cock is just as hard, following along!

guilty pleasures never cease, more more

‘OK’, I tell her, ‘I need you to be a big girl now and uncross your legs for me.’ She slowly lets her legs untwine and relax open slightly. ‘OK, now just lay back – all the way down again’, I ordered. She fell back until her head was flat against the bed. I held her feet firmly around her soles and slowly pulled them up and out to the side. This caused her legs to fully spread open.

I looked down and saw her white little panties pulled taught against her little pink mound. She had closed her eyes and was laying perfectly still, trying not to breathe. My own cock was still as hard as steel.

By the look of you Frisky, it looks like you could make a lot of girls happy. If I was your patient, I'd have my knickers round my ankles by now!

'You're doing great', I told her, 'but now I need to have a look at your vagina'. By now she was starting to get anxious and I was worried that she might try to close her legs, or worse, get up off the bed, so I forced her thighs a little further apart and pushed her feet down firlmy on the bed, telling her to stay still..

'Oh my god, you can see up my skirt can't you?' she wimpered. 'You can see everything can't you? How long do I have to lay like this? I'm embarrassed', her voice gently crackled. I gently rubbed her leg. 'Now, now sweetheart, just relax and let the doctor do his job', I said reassuringly and gently kissed her on her sweet little lips.

Don't stop now, FB!