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By (user no longer on site) OP
over a year ago
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Since the age of 18 I have loved to cross-dress. I got into the habit by being lucky enough to have a very sexy mother who wore some gorgeous lingerie and high heels. My luck was even better than that because my auntie also had a fabulous collection of underwear.
You find yourself left in the house alone quite regularly – in my case either my own home or when the family went away visiting my auntie. I’d often be able to dress in their underwear for hours.
I should point out right now that high heels are my overriding passion and fetish.
So there I was, happy to cross-dress and have some wonderful wanks. The stamina one has as at 18 meant I could often cum three or four times during a two-hour dressing session.
The other thing you notice if you have a slim, attractive mum is that your mates tend to fancy the arse off her. Several of my more forthright friends would regularly tell me that she was fit and that they wanked about her. It didn’t bother me, but in no way did it arouse me either.
But all that changed when a much quieter friend of mine – Michael – one day admitted that he fantasised about her. We were 20 years old by this stage and Michael was one of the few boys in my year to not have had a regular girlfriend. He wasn’t gay, just simply very shy in front of girls.
Anyhow, we started hanging out together a lot more in the sixth form and on Tuesday afternoons were allowed to leave at lunchtime for ‘free study’. Most of the time the other lads would go to the bookmakers or try to get served in the pub. But Michael and I often went back to my house because my mum and dad both worked and it was somewhere quiet to hang out.
One day one of my mum’s bras, along with some very sexy matching French knickers, were on the radiator drying. I had nipped upstairs to get a record and Michael obviously hadn’t heard me come back down. As I walked in I saw him holding the knickers in his hand and rubbing the bra against his face. He jumped a mile when I saw him and he went bright red.
“Hey, relax,” I told him. “Half the lads at school fancy my mum like crazy but as far as I know none of them have touched her underwear! You’re way ahead of them. Do you fancy her then?”
At first he was reluctant to say anything, so I asked if he wanted to see her full collection. He asked if I was serious and I told him we had more than three hours until anyone was due home. “We’ve time to catalogue every item if you like!” I added.
So after a bit of umming and ahhing I showed him to my parents’ bedroom and opened the lingerie drawer and my mum’s wardrobe. I was getting very turned on at the thought of showing Michael her high heels and her lingerie. For the next 15 minutes I lifted various outfits out and let him touch them, something that obviously gave him a lot of pleasure and he really started to relax.
“I imagine you’d like to have a wank?” I said. He grinned and blushed again, and I then offered to leave the room so he could have his fun. He did so, and about 10 minutes later was back downstairs having relieved himself and put everything back. We spent the rest of the day chatting about sex fantasies, our mutual love of high heels and other similar stuff.
As he prepared to leave I asked if he wanted to do the same next Tuesday, or perhaps even a little bit more. He was very eager and we decided to head for my house at the earliest opportunity the following week.
This time I decided I would seize the initiative and when Tuesday came I collared Michael mid-morning. “All set for this afternoon?” I asked him. He was clearly very eager, so I decided to take the plunge. Away from everyone else I added: “I’ve dressed in my mum’s underwear dozens of times. It’s been my secret up to now, but if you want to see me in her things I’ll dress up for you?”
I was worried how he’s react but he seemed totally onboard with the idea. He even made it clear which outfit he’d like me to wear.
So the afternoon came and we rushed home. I asked him to have a quick shower and then I did the same. I had got the outfit from the bedroom – a gorgeous crimson bra, matching suspender belt, French knickers and a pair of black stockings. To top it all I had her highest pair of heels, black ones, about 5 inches high. I told Michael to lay naked on my mum’s bed while I got dressed in my own room.
All my previous experience meant I was very nimble getting my outfit on. No fussing with fastening my suspenders – I was an expert! I slipped on the high heels – one of the most sexy experiences possible when you’re a cross-dresser – and I knocked on my mum’s bedroom door.
Michael invited me in and I paraded in front of him for about one minute, running my hands down my stockings, putting my sexy shoes on the bed in front of him. “So what do you think?” I asked.
“See for yourself,” Micahel replied, pointing to his erect cock. I had never seen an erect cock in the flesh before. I had watched plenty of porn, but seeing everything in real life made me shudder with pleasure and with a sense of power. It was me, dressed so sexily, that was making Michael so hard.
I invited him to touch me. He ran his hands up my stockings, then started to brush his hand against my hardening cock in my French knickers. I rubbed my shoes and feet against his cock, knowing how much high heels turned him on. I could tell he was incredibly aroused and I had to tell him to stop rubbing me because I was in danger of cumming.
After more touching and more slutty parading around the room I said I wanted to play with his cock. For the first time ever, I held another man’s rigid cock. I loved the warmth of the blood pumping through it, the feeling of it twitching in my hand. Before long Michael stood up on the bed and pulled me up so I was standing on the floor. His cock was right in front of my face and without having to say anything the time had obviously come for me to take him in my mouth. I ran my tongue around the tip of his cock, tasting the distinctive saltiness of pre-cum for the first time. Neither Michael nor IU had ever had a blow-job, so I was doing what I thought would feel good.
I asked him to describe his fantasies and then took his whole shaft in my mouth. He began to describe the thrill of fantasising about fucking my mum, of ripping her knickers off her wet pussy and fingering her. I stopped sucking him to join in the fantasy. I told him she was a cock-hungry slut who loved teenage cock. Then I got back to work sucking and wanking him into my mouth.
I could tell it wasn’t going to be long until the point of no return. “I want to cum on your tits,” Michael said, panting and groaning. “I’ll pull out and shoot on your when I’m there.” At this point I pulled my own cock out of my knickers wand wanked myself as I sucked him. 30 seconds later he pushed my head back and aimed his pink, throbbing cock at my bra. He unloaded what looked like gallons of cum all over my chest, and as he was finishing I also shot my cream. The bra was in a terrible state, but years of practice meant I didn’t get a drop on the knickers.
We quickly got cleaned up and tidied the room. I hand-washed the bra, dried with a hair-dryer and put it away.
I expected a very uncomfortable hour or two when we both got back downstairs, but it was just the opposite. We chatted about the importance of everything staying a secret and then began planning all sorts of roleplay an fantasy situations for the coming weeks.
In the end we spent most Tuesday afternoons with me dressed to kill and Michael growing in confidence every visit. He learned to suck my cock as well as I learned to suck his. But most of all he loved the underwear and high heels. I have great legs to this day, and back then my body was even firmer. I was in my element being his sexy, high heeled fantasy ‘girl’.
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Lovely read, perked me up no end (needed to cos i is ill 
)
