Heather

This is mostly a true story with embellishments. I am now a 60 year old sub gay crossdresser but I will start this story at the beginning of my journey.

As with most of my generation the story begins in the cottages of a city in Scotland, where I was first touched by an older man and ran a mile. However I realised that it gave me a great thrill and I returned the next day to begin what was my life as a gay.

I loved the taste of cock and sucked many through the holes in the walls. I also sucked many men in derelict buildings and in parks. I was often played with but even at this stage I preferred to give pleasure to my men.

I became quite well known and whilst I went to a few guys homes I had no regulars as I just loved cocks and wanted as many as I could have.

However this all changed in my early twenties

During one of my many trolls around for cock I met a guy who invited me back to his house. We had a nice leisurely session and I enjoyed it so much I let him make me come but stressed I preferred to satisfy men.

We had a chat after when he suggested he could help me explore my inner desires. I found this interesting and he explained I should become a submissive and he would instruct me how to develop my skills. I agreed to call the next day.

I wondered what would be expected of me and called the next day to find out more. He took me into his bedroom and I noticed some clothes on the bed. He explained he wanted to turn me into a sub sissy and I would need to dress properly.

I was told to strip and he got me into black female panties which were tight around my small cock, which was getting hard. He then had me pull on black hold ups and I was getting so horny he noticed and said I would have to learn not to get hard. He then produced a black bra that he made me wear. I was so excited and loved the feel.

I then was introduced to nipple play and little did I know what this would mean to my life. He played with my nipples through the bra and I was tingling and felt so good. He then got my nipples out and felt the tingle for the first time of a mouth on them and then the pain of them being bitten but I screamed for more and they were bitten so hard I was crying.

I had only had my man pussy fingered but he said I needed to be introduced to my pussy being used but before feeling cock he lubed me up and inserted the end of a brush - wow what pain but this turned to pleasure very quickly. He then said I should suck his cock and I loved his nice sized cock. When it was hard he made me get on all fours, lubed his cock and slowly inserted it into my pussy and he drove me wild and I came. Eventually I felt his cock go hard and then spurted his cum into me. WOW

This went on for a few years developing into me becoming a fully dressed sissy and be used by my now Master.

It also moved into punishment. He would clamp my nipples, restrain me and the punish my ass eventually arriving at the cane and I often left with stripes across my ass but a wet dripping clit.

I still went cottaging and loved many men.

I then moved with work and my Crossdressing became more frequent.
I had a flat and was able to indulge my desires and often got fully dressed, made up and wig to meet men but never went out openly. I loved men using me as they desired and the bigger harder cocks they had the more I wanted.

One night I went cottaging mostly male attire but full female underwear and a female blouse. I was  unfortunately rounded up in a police action and was bailed to appear at a later date.

I thought my life was over but a few days later I answered my door to the policeman who arrested me and he told me he would be back in an hour and wanted the full Heather. I thought this was a try on but got ready and sure enough he did come back.

He grabbed me as soon as he got in the door and he ripped the dress of me and immediately went for my tits. This drove me mad and I would find out later that my tits were well marked. I got on my knees got his cock out and sucked it hard and tasted his pre cum.

He said I was a naughty girl and ordered me over his knee and I was severely spanked. He then filled my man pussy and filled it with much cum.

He then left saying he would be back but would leave a note when he was to call.

He called many times and occasionally brought a friend who was very well endowed and I loved being spit roasted by these 2.

The police case eventually was dropped but they invited all the people who had been arrested and told us all together. One man kept giving me the eye and on the way out I gave him my phone number, not expecting to hear from him.

But this for the next chapter.