Hi, Mum of 4 sons. I'm another non-Yank, from Sydney Australia. Welcome to a good place for getting advice and help. I've found the people here to be wonderful at giving me the confidence and courage to insist on the changes we've needed to make, both in education and health management.
I didn't post before because it was sounding totally out of my league, but as I read more posts I'm beginning to see something familiar.
What I'm seeing - a flatmate I once shared with. He was a lovely bloke, very masculine in so many ways, but every so often he needed to 'take a break' from being male, and cross-dress. This was back in the mid-70s, when he could have been arrested if he stepped outside the door wearing a dress. So we stayed inside and I helped him.
What he was terrified of, was being judged for it. He had hidden this for a very long time - years, in fact - and relaxed with me. We WERE just friends, I was already going out with husband at that stage.
Then he got a girlfriend who he didn't tell about this. I noticed that a lot of his time, his energy, seemed to be spent in 'proving' his masculinity, to extremes. In the block of flats we were living in, the neighbours downstairs and next door complained about the sound of his bedsprings being pounded so frequently through the night, with his 'activities' with his girlfriend. I was in the next room but didn't complain because I had begun to use earplugs (I had been hearing a lot more than bedsprings!).
His hobbies were extreme sports - he was into hang-gliding in its earliest, most dangerous days. Anything dangerous or risky, he was there doing it.
In his case, there was nothing homosexual about him despite the cross-dressing. But he seemed to really need it, as a release. On his dress-up nights his personality seemed so different, almost submissive (as compared to his usual 'out there', in-your-face masculinity).
Then his girlfriend found out. She didn't have an ounce of empathy in her body, so she insisted it all had to stop - the cross-dressing especially. She was happy with the non-stop sex of course, but when he crashed his hang-glider and broke a collar bone, THAT had to stop as well.
At about this point I left, because she was blaming me for everything about him she didn't like. In her mind, I was the reason he was cross-dressing, because I had somehow corrupted him by letting him borrow my clothes.
I last saw him about four years later. They were married (as were husband & I) and they had a young son, a cute kid. He tried to get me alone to talk but his wife was watching him like a hawk and I wasn't too keen on any more trouble from her. He was clearly very unhappy and feeling trapped.
One thing he did which I think was very clever - for years he had managed to indulge his enjoyment of women's clothing, by using his Scottish heritage and wearing a kilt whenever possible. husband also has Scot in him so we all would go to a local Ceiligh (or clan gathering) and we enjoyed some wonderful Scottish dancing. With almost all the men there wearing kilts, my flatmate didn't seem out of the ordinary at all.
A non-Scot can still do this, by joining a pipe band and learning to play either bagpipes or drums. You don't have to be a Scot to join anything like this.
I would be considering a number of possibilities here.
First, he could have gender identity issues, which could also be upsetting him and making him wonder if he's "sick". Imagine what any male friends his age would say to him, if they knew. While he's feeling so confused he probably hates himself, in the extreme, and expects that anybody who knows his 'secret' MUST also hate him.
Second, he may be like my flatmate and be perfectly 'straight', but just happen to like the feel of women's clothing. In my opinion this is OK, although I recognise that society doesn't always agree. But he needs to know that stealing clothes is NEVER socially acceptable and wouldn't be with me, either. There are legitimate ways in which this could be indulged, hopefully releasing enough of the safety valve so he can cope a bit better.
Third, this could also be sensory, and it could be the feel of the fabrics that is attracting him. Again, there are socially acceptable ways of indulging this, too, and he needs to seek those out and not try to be sneaky about it. If he's stealing your undergarments as well, then I don't think this is sexual; I do think sensory may be the most likely factor.
Whatever happens, he needs help. He needs to know he CAN share this information and talk about himself without it utterly disgusting people. He needs to know there is an escape here, other than suicide. One important thing - if he is feeling this disgusted with himself, it shows he is a very moral person at heart who can't cope with this side of himself at all at the moment.
I'm thinking of a umber of possibilities here. ADHD could still be a factor for him, but he could also have Sensory Integration Disorder (SID) (Sensory Integration Disorder) as well, which you can get with a number of conditions including Pervasive Developmental Disorder (PDD) (Pervasive Developmental Disorder). Asperger's Syndrome fits under this umbrella and I can really vouch personally for the sensory issues, almost to the point of seeming to be fetishes. OK, beyond fetish point, in my daughter's case. She's lucky she's a girl, or she would be like your son I suspect. Or my former flatmate. She is so very much into how fabrics feel next to her bare skin. She's an incredibly sensual creature, we knew we'd never keep her 'intact' to the altar ("round heels", her father says). We knew the first boyfriend she slept with would be almost in shock at her sensuality - and he was. The poor boy still hasn't gotten over her. Our friends at church cannot understand how we can apparently 'condone' our daughter living with her current boyfriend - but they didn't raise her or they wouldn't argue with us about her! We just have to accept that she is making her own choices now.
What we have done, or allowed our kids to do, to accommodate their Sensory Integration Disorder (SID) - I made things for them, practical things suitable for them, out of the substances they craved. For example difficult child 1 craved lemon scents so I made (actually taught him to make) a satiny pillow stuffed with lemon verbena leaves, which he put inside his pillow case. difficult child 1 also likes silky fabrics so I was able to buy him a pair of pure silk boxer shorts. He likes the synthetic satiny ones too.
difficult child 3 is into the feel of towelling. So I made him a pillow out of towelling. We would carry a towel, or cloth nappy, in the car whenever we were going out. I made him some shorts (for the US people, this means outer wear in Australia) out of an old towel, he can go swimming and then change out of a wet swimsuit into these shorts and he has towelling next to his skin. difficult child 3 hates creamy textures in his food, so I don't try to feed them to him.
easy child 2/difficult child 2 loves satiny fabrics and also fur. Anything soft and fluffy, really. She made a cow-print fur fabric cover for her high school folder, then made sure she carried her folder everywhere instead of putting it in her school bag. She's made pillows out of velvet and satin. She makes her own clothes. She also wears Victorian corsets tightly laced, because she says "It's like wearing a hug." She is also fussy about her food, she doesn't like 'bits' in her food, so no biscuits or cakes with nuts at all; no fruit cake or fruit bread with peel. Most food for her has to be very plain.
I do think your son needs to be re-assessed, if only to help him understand where he is and what is happening in his brain. If he's gay, he needs to feel it's OK to admit it. If he's SCARED he's gay because he likes satiny fabrics, he needs to know that's OK too. Beau Brummell was a male fashion icon in his day who was well able to indulge his passion for wearing fine fabrics. But whatever the cause of this - not only is it important to know, I think it's important to accept it so he can stop stealing clothes from other people. I think that is a No 1 priority. Until you can sort out why, I think he needs his own legit 'supply'. But if the thrill of stealing them has become tangled in this, then DEFINITELY he needs counselling support so he can learn how to untangle it again.
It is so difficult when sexuality gets confused in the mix of all this. With puberty coming in, it's a difficult time anyway for him.
Good luck. Keep us posted on how you get on.
Marg