This is a continuation from How It All Started
By the time I was 18 I got a promotion at work and which meant moving to another part of the country and obviously moving out from my mothers house. I did come home once a month for the weekend.
I was quite nervous about the new job and moving to a new area where i knew nobody and decided that I needed to find a girlfriend as soon as possible to help me settle down. I, for some reason was really popular with the girls straight away, almost like being in Hot In Cleveland (30 years too early).
I lasted there 4 months before my boss decided I was home sick and got me a transfer back home. Ironically once that had been decided I wanted to stay but it was too late. I still had about a month to go and suddenly all the girls wanted to go out with me, even some who already had boyfriends. So I started seeing a few, behind each others back.
While I was waiting for the train home and I saw in the newspaper and magazine stand a copy of Gay Times. I decided for a dare to myself I should buy it, to see if the woman serving at the counter would react in any way or maybe deep down to out myself to someone I didn’t know but at least I had to done it to someone. Another exciting and naughty deed.
It took me a while but I finally got my nerve up and did it. My heart was thumping away like mad. I was probably shaking too as I gave her the money. She didn’t react at all but I still felt a rush buying it.
I didn’t have the nerve to read it on the train so had to wait until I got home and into the privacy of my bed room. To be honest there was nothing in it that held my interest so I just put it back in my bag to get rid of later.
Over the weekend my mother went into my room for some reason I can’t remember. When she told me she had at first I thought nothing of it then I suddenly thought oh crap I hope she didn’t see that magazine. I did go bright red at the thought.
A couple of days later I realised she had seen it when she started going on about it being about time I had a girlfriend. I was a little embarrassed but actually not too much.
We lived quite near to a beach and from time to time I loved walking up to the pier and the arcades and sometimes along the beach. The last time I did this was in the evening and it was dark. I wasn’t too far from the pier but it was already desserted when a guy cycled up behind me and said hi. I replied and then he said I take it you’re gay then. I was definitely surprised by that because there was nothing to suggest I was. I said no. To which he said well do you want a blow job? You don’t have to do anything but sit there. I just answered no thanks. A guy went past us and he said hi mate to him like he knew him and he said hi back. In my mind I thought about saying yes but I was just way too suspicious about him, thinking he had friends and would beat me up and mug me so at the earliest opportunity I crossed the road and went round a corner and stopped by a wall. A few minutes later I saw him ride off and look back at me. I quickly walked home wondering about what could have happened and why did he think I was gay.
A few months later I did have a girlfriend and about a year later we moved in together. She would go and visit her mum once a week in the evening. A few weeks later of this happening I was bored and decided to try on my girlfriends underwear. She had much more sexier clothes than my mother and it really got me excited wearing them. I especially enjoyed wearing her short skirt. To add extra spice to things I decided to venture outside. Not too far, but we lived at the top of three floors with someone living below. It was either a woman or I imagined it to be this. I went all the way down to bottom past her door and back. As far as I know nobody saw me.
When I got back inside I imagined the woman had opened the door and demand that I get my girly ass inside. So I did and she said I bet your girlfriend doesn’t know you like dressing in her things and being all girly does she? I admitted to her I didn’t and she said you are a naughty little girl aren’t you? I just nodded. She then said well naughty girls like you should be spanked so get over my knee now. I did as I was told. She pulled up my skirt then pulled my panties down and spanked me hard. Then sent me back upstairs. I enjoyed that fantasy but then it was time to change back to boring clothes and got and pick my girlfriend up from her mums house much to my disappointment.
I would do this every week until we moved to a new place. I’m not sure why but I stopped doing then. My girlfriend and I had sex every night up until this point too when we decided to do it less frequently. I didn’t know the real reason she wanted to stop at the the time, which was because she had started seeing someone at her job.
Shortly after we moved again and she started going to her mums twice a week and going to a gym (with her lover, which I still didn’t know about). I didn’t mind her being at home less because I had started dressing up in her clothes again. I just couldn’t resist her sexy clothes. One particular item was a sexy, pink baby doll I had bought her that was really for me to wear when she wasn’t around and it became my favourite thing to wear, sometimes with high heels. It made me feel so good.
At work a new guy started and he was very friendly. A few weeks after him starting, rumours were flying about him being gay and so it turned out to be. He told people that he was gay and living with his boyfriend. No big deal to most people but obviously a big deal to some.
One day he showed me a pic of him dressed up for the rocky horror show in women’s underwear. I didn’t think too much of it but did wonder why he showed me it.
One day, on my way from work home I saw him outside his block of flats and and he said hi, we talked for a while before he asked if I wanted to come upstairs. Well my girlfriend was working late so I thought why not.
We chatted for a while, had some tea then I looked at the time and realised I hadn’t taped Neighbours or Home and Away for my girlfriend so I told him I had to go. He seemed really disappointed and I did feel bad but not as bad as she would make me feel if I didn’t record her shows.
Looking back later I realised that he was probably interested in something more but as usual I was oblivious to it at the time.
Not long after, I discovered my girlfriend was cheating on me and after a few rocky months we split.
Whilst living on my own I did consider phoning a gay dating chat line but as usual didn’t have the nerve.
To be continued . . .