So Sunday morning saw me sitting at the table trying to eat toast with a nervous, dry mouth, wondering what the hell to do about Gwen. I really liked her, she was good fun, and VERY attractive, no , SEXY!, but I knew that if she got flirty again, or wore that sexy wonderbra, I'd make a pass at her, and I still wasn't sure if that was what she wanted. If it all went wrong, the whole family would find out, and all my mates, AAARRRGG! shit, shit, shit.
I got the car keys, and decided that I'd be very cool and collected, and just move the bloody table and go for a drive out of the way. When I arrived at Gwen's, she was already working away cleaning up after the decorating, and, to my relief, was NOT wearing 'THAT' bra! She was in jeans and a tee-shirt, but for once her long hair was down in a long ponytail, and pulled over her shoulder. She had a little make-up on with a soft coral shade of lippy, and she looked a lot younger than her years. It was so unusual back then to see a woman of her age in jeans, and it really took years off her, and it meant I didn't have the distraction of her long legs in a short skirt to contend with.
We carefully moved the table back to it's position, and I helped with the clearing up for a while, gradually getting more comfortable in her company, and we were soon laughing and flirting as we got the dining back in shape.
Gwen made a pot of tea, and we sat in the kitchen just talking about nothing really, cars, music, holidays, all the usual stuff. She had been reading the 'Womans Own' magazine, and it was on the kitchen table, open at an advert for 'Playtex', and I kept taking a sneaky peek at the picture of a corset in the ad. I wasn't sneaky enough, though, as Gwen suddenly said " you looking at clothes again?" I went bright red! She didn't say it in a nasty way, she laughed as she said it, and when I blushed, she reached over, took hold of my hand and said "sorry, I've made you blush now, I'm just joking".
She said that she had noticed that I spent a lot of time checking out her clothes, and she had seen me looking at womans' magazines. She still had hold of my hand, and I must say I had no wish to move it, it felt really nice. We talked for ages, and I found myself telling her all sorts of things that I'd never told anyone else, including about my occassional dressing up. She didn't seem shocked, she just smiled and nodded, then explained that her late husband was also into crossdressing, and they had enjoyed playing dressy-ups when they were first married.
She admitted that she HAD worn the top and wonderbra on purpose, and was very pleased with the result, she knew I couldn't take my eyes off it. I said how nice it had looked, and that it was a shame she hadn't worn that bra today
She said she could do better than that, and standing up, deftly pulled the tee-shirt over her head! She dropped her jeans, and stood in front of me in the most beautiful matching undies I'd ever seen. It was a lovely 'Janet Reger' bra, scallop shell cream polyester, trimmed with lace, underwired with lace-covered straps, and matching french knickers. BLOODY HELL! there's a woman standing in front of me in bloody lush undies, inches from my face, and I've got a massive hard on and I'm sweating like fuck! She could see what she was doing to me, and, with a little giggle, pulled me to my feet. She stepped out of her jeans while I tried to cover the very noticeable swelling in my pants, and, wrapping her arms around my neck, pulled me to her near-naked body. She stretched up and kissed me on the lips, gently at first, and then with a bit more pressure, as she eased the tip of her tongue between my lips. I dropped my hands to the cheeks of her bum and stroked the silky material as my mouth opened and we worked our tongues together. Gwen slowly moved her right hand down between our bodies until she reached the bulge in my pants, and, still snogging me, squeezed my cock.
WHOOSH! I shot a load of hot spunk into my underpants! FUCK! what a dick-head! I'd just cum in my pants and I'd never even had a feel of her tits or fanny! I turned my usual shade of bright red, and stood like a fucking idiot, shaking and panting as I finished the longest cum I'd ever had. Gwen was just standing there, giggling like a girl, then she reached up and stroked my face gently and said " that was lovely, you really do like ladies underwear, don't you?" We both set off laughing, and hugged each other, then Gwen took me by the hand and said " let's get you cleaned up, come on upstairs".
I went into the bathroom and wiped as much spunk as I could out of my pants, and shoved a bit of bog-roll down my front to soak up the wet patch on my jeans. Gwen was standing at the door of her bedroom, still in those fabulous undies, and I started to feel VERY silly, so I said that I'd better get going, and went to go past her to the stairs. She grabbed my arm, pulled me to her, and kissed me very gently, then said " you had better come back tonight, I want to give you a fuck you'll never forget". WELL! I was shocked! I was stupid enough to think that young people had invented that word, Yes, I knew little in those days!
Well I did go back that night, we fucked for hours, it was fucking fantastic, and it carried on for years till I moved away to work. I will always remember that first time, though, and the sight of that lovely underwear. Trannies, eh, it's always about the clothes!
