I was back to my old ways. Pam was not around at that point so I was seeing another lady, quite a bit older, and she was really persuasive at getting me to try anal-specifically a strap on dildo into my rosebud. She said all crossdressers liked being taken that way.

Mabel she called herself and she opened a drawer saying that she had many different sizes and that a beginner’s one would suit me. She showed it to me-black, about 7” long and about 3 or 4 cm in diameter- and then proceeded to tie my wrists to each side of her bed and put my ankles into a spreader bar.

She said that given the way I was-a bit of a submissive sissy-this was the way to make it particularly enjoyable for me. She put a condom over the end of the dildo and told me to suck the end of the dildo until it was very wet.

Meanwhile she was lubricating my rosebud until it felt similarly wet and had been prepared by her fingers.

This was quite consensual as I had wondered what it might feel like. Any porn involving crossdressers would certainly show rosebuds being enjoyed by fellow dressers.

Mabel attached the dildo to a harness strapped over her pussy. She stood in front of my head, which was on the bed, as the wrist ties were only allowing me a very narrow amount of movement and she wanted me to see how she would enter me.

She disappeared from my field of view and began to massage my bum cheeks. Then, pushing her thumbs down to my rosebud, she entered with her fingers and began to slide the dildo down the side of my bum cheek until it was next to her fingers, ready to enter.

As she took her finger from my rosebud, she simultaneously entered with the dildo and widened my sphincter with her thumbs. The dildo was wider than her finger, and felt slightly uncomfortable-(her finger had felt nicely sexy!)

She kept pressure on my rosebud and I felt the dildo sliding up inside my pussy; then pulled down and back up. I was taking the full 7” apparently, as she was calling me a good girl and building up a bit of a rhythm. I could feel her stockinged thighs push against my own stockings as she pushed into me and, I must admit, strange though the sensation was, I was getting very aroused. Then she did a deep thrust and stopped, deep in my pussy.

Leaning onto my back, she reached round and grasped my clitty and began to gently rub and pull me as she slowly moved the dildo a few inches in and out of my pussy.
This was very erotic-she was calling me a good girl, whilst fucking me like a woman might be. I felt myself cumming but this did not stop her. Still she slowly pushed the dildo and gently played with my clitty.

I came into her hand and she let my clitty fall away. Raising her dripping hand, she wiped it from my eyebrows down to my chin. I licked it like the sissy I was.

So, I had been taken like a woman might be and I did like it, though my orgasm was more linked to a lady playing with my clitty than being fucked up my pussy.
I did wonder what it would be like for a cock to cum in my pussy.

So, that was my anal virginity taken, and it was very enjoyable as a whole experience.