Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed. after 10 or so seconds she closed the door and walked away.
i was mortified. i was kneeling on my bed, with her clothing catalogue open at the lingerie section laying on the bed before me, hard cock in hand. But most embarrassing.....i was wearing my mom's black bra, suspender belt and black stockings....her black panties were thrown onto the bedroom floor, cast aside when the urge to cum had become too much.

for weeks after this incident, we barely spoke. as it was just the two of us since Dad had left, this was all the more awkward. although i was glad dad wasn't around to hear of my "perversion"

Other than her initial disgust, mom seemed to have an overriding feeling of guilt, like she'd let me down, not giving me a male role model to follow. she'd questioned my sexuality, which i assured her i was straight. Coming out as bi-curious now would have destroyed her!

one day upon returning from school, i walked into the kitchen to find mom and her friend Linda. Mom had a glass of wine and was slurring her words. "here she is" she blurted out she'd clearly been talking with Linda about my indiscretion all afternoon.
Linda however reprimanded her for her mocking tone. and explained to her that my dressing as a girl was most likely a passing phase, and that it didn't make me gay, just curious. she also said it was probably just the feel of the clothes against my skin that aroused me. She seemed strangely clued up.....i was however thankful, as my mom seemed to listen and take her comments on board. even apologizing to me and gave me a hug.

Linda then turned to me. "look Simon" she said "I understand what you're going through right now, if you'd like to come over to mine tomorrow night, we can talk, it would probably help for you to talk to someone other than your mom about this right?"

How embarrassing.....i looked at mom, she looked puzzled, but after a brief paused nodded in agreement.
I tried to insist that i didn't need to talk to anyone and that i didn't even want to dress up anymore (which was a lie....I'd not dressed since mom caught me and was now desperate to slip into something feminine)
reluctantly i agreed. We arranged for me to visit after school, I'd go for tea and then we'd chat, before she ran me home.

next day at school was a torment. i was dreading "chatting" with Linda. God knows what she thought she "knew" that was going to make thing better.
I got to her house at about 4:30. her small red car was on the drive, so i knew she was home. gutted!
I knocked, she answered she was wearing a black tailored skirt suit, and white blouse with black patent heels. she looked smart. like she'd dressed specially.
"you look nice" I said, "Thank you Simon" she replied. I've been for a job interview. This seemed unlikely, Linda worked from home and judging by the decor was doing quite well.

we went through to the kitchen where Linda served tea. She'd prepared a full cooked dinner, like we only had on Sundays at home. "Job interview my arse" I thought.
Linda wasn't an attractive woman, but not ugly she was short, but around my height in her heels. she had almost white blonde hair. not long, but backcombed to make it "bigger" she was I guess late 40's. She was single. Mom had told me the gory details of how her boyfriend had left her for a much younger woman.

Over the meal we made small talk about school, about whether I had a girlfriend (I didn't) a boyfriend? (i'd acted indignant and said NO!)
I'd tried to avoid the subject hoping she'd just be happy with the small talk but eventually she'd asked how long i'd been dressing.

"around 12 months"

"Because it turns you on?"

"I guess so yes..." (embarrassed)

"look, your mom is wrong to reprimand you about this, in fact, if you were my son, I'd just get you some of your own clothes to wear and let you work it out"

"erm.....wow" I responded.

"Look, when I was with Bryan (the runaway boyfriend) he liked to dress as a woman, and I was fine with it. It didn't make him gay in fact we had some great night with him dressed as briany"

"erm ok"....this wasn't where I'd expected this conversation to go.

"come with me" Linda said, standing and taking my hand and leading me from the table.
We went upstairs to what I assume was Linda's room. It was pretty and floral with a huge 4 poster bed, a little over the top in a room this size, but still nice.
Laid out on the bed were several items of clothing..... women's clothing....women's underwear.
"These were Briany's" Linda said. "would you like to try them on"

Now in hindsight, I should maybe have said no....looked at her like she was a weirdo and walked out....maybe even told my mum about her. But as I said earlier, I'd not dressed up now for around 8 weeks and the urge to raid my mom' knicker drawer was becoming too much. Here was Linda, with a wardrobe full of stuff for me to wear!
"yes please" I blurted out
"good boy" she said, "you'll need some help getting into that corset"

"oh erm....yeah I guess" I said.....she wanted to stay while I dressed?...she wanted to watch. I'd kind of assumed she'd have left me alone to try them on.

I undressed.

Linda giggled "your so smooth" I didn't shave, I just hadn't got bodily hairy like most of the other boys at school.

Finally I stood before her in just my pants. "those too silly" she said. "i'd rather not" I replied....

"look, I'll turn away and you can swap them for those black panties there ok?"

I nodded. and Linda made a theatrical gesture of covering her eyes and i quickly switched panties. This whole little charade was pointless as when Linda opened her eyes, the black panties barely hid my erection. Linda grinned.

"Turn around" she said, lifting the corset from the bed, I slipped my arms through the straps as she held in up to me, and then turned for her to fasten the clasps at the back.

She fastened me in, it was tight, but so feminine, finished in black and purple satin, with black lace trim around the cleavage and thighs. it had 4 suspender clasps. Linda said "sit down" and handed me a pair of black lace topped fishnet stockings, "put these one" she said
I rolled back the stockings and slid them up my legs. Linda looked on. Clearly enjoying what she saw. I smiled at her. finally becoming more comfortable in this situation.
Finally Linda reached below the bed, and pulled out a pair of black heels. 4" high. I'd never worn girls shoes before.
I slipped them on, they were a little tight, but not too bad. Maybe just a size too small.
Holding my hands Linda helped me to my feet. I was now taller than her. She kissed me, full on the lips, tongue probing my mouth.
"you'll be beautiful when I do your makeup and wig darling" she said. "but that's for another night isn't it, as I can see your a little too excited for that right now aren't you?"
I nodded....we sat back down on the bed. Linda next to me, still kissing me, she took my cock from the panties.
First she lingered at the tip with her long painted nails, so much pre-cum, then she grasped it, tight and began to jerk me off....still kissing me....oh god i was cumming already!