Well, this is how it all started for me.
I was a sales rep in my 20’s staying in hotels up and down the country. This was pretty dull, long before the internet to keep us busy. I would usually have dinner somewhere, then back to the hotel for a few drinks. I would meet some folks now and then for a few drinks and a laugh, but not often.
I usually had some copies of “Escort” or “Fiesta” , soft glamour porn mags, which I would wank off to as often as possible.
Well, one evening I was in with a group of three strangers at a hotel bar in Oxford, watching football on tv and ordering rounds, and generally having a laugh. One of the older ones , Alan, (probably only in his fifties), seemed to take a shine to me. We were all getting drunker, and I definitely remember him next to me in the loos having a pee with what looked like I was not gay or bi, but I remember feeling a thrill peeking at it. And he knew I was as we exchanged a glance.
Back at the bar things were winding down and the others gradually left, and before I know it the two of us were smoking lots of cigarettes and drinking a bottle of red wine which had appeared.
To cut a long story short, we eventually got talking about the boredom of hotel life and how wanking was what half the hotel occupants were doing. I told him of the magazines I liked and the glamour girls in suspenders etc. He loved that too, and told me he had a great lot of magazines which specialised in that sort of thing. Did I want to go up and borrow a few ?
Before we knew it I was up in his room with the winesitting in the bed with the telly on as he searched through a bag full of dirty magazines for me. I can’t tell you how drunk and thrilled I was. I knew something was going to happen.
He handed me a few mags and said what do you think of these ? They were great. Lots of amateur ordinary mature ladies in lingerie, I’m sure they were German of French mags I can’t remember. Anyway as I flicked through the pages I stopped suddenly - the middle of the mag was full of men in in panties and stockings suspenders etc. It wasn’t as glamorous as lots of you are now. It was big fat trannies in old fashioned undies and dirty old men in wigs. But my heart was hammering. “Like that do you?” Alan said.
I gulped and admitted that I did.
He then got me some mags he thought I’d really enjoy in that case, and bit was he right. Cross dressers and trannies of all sorts in lots of sexy outfits with hard cocks galore.
My face was flushed with booze and being turned on, and just as I was about to turn to say something, I felt him at my shoulder pointing to his favourite pics in the mag. “Just like I’m wearing” he said. I turned round and he had dropped his trousers and was wearing a pair of white French Knickers which were too small for his chubby frame. I’m sure I gasped as I saw his hard cock pushing against the material. I wish I could tell you about load of all night sexual exploits, but reality wasn’t like that. I barely had time to get my zip open and trousers down before he grabbed my cock and starting wanking it hard. He pulled his panties to the side until his stiff upturned cock was wagging about. I shot my load within a minute, just about the same time his spunk splashed hands free all over the chest of my shirt. It was utterly unforgettable.
We did meet several times more over a year or two. And things got a lot more kinky. But that first time changed me forever.