I always loved vintage lingeri as that's the kind of stuff I was exposed to where I started looking at men's magazines from the seventies from the seventies. I'm not sure about the actual start of this but my cross dressing started including vintage laundry especially corset's shaper's shapeware pantyhos nylon slips full slips.
It used to be feasible to buy large Lots on Ebay but most of that stuff now is overpriced, and a lot of it from certain buyers I used to trust are just redyed once that they claim or original complete bullshit.
Another thing that happened was a period of very long affair, for nearly 20 years, with the neighbor who was 25 years my senior. She had lots of the classic lingerie, tap pants and tops camisoles and it was very hard for me to open up the real reason I love them so much was I could also imagine myself wearing them. Sushi sometimes indulged me when she wanted more profound reaction out of me.
Another was an older woman I met in college, who ran the first aid station. Normally a friend of mine was there, who I rented a basement Suite from so he was usually there late at night when I was in a cabin or physics lab and there had to be first aid people around. But as soon as that was done I could get a ride for the night home. Sometimes though, I would just show up late and rather than going home work on my homework for a few hours there as there was very seldom any calls. The only times I ever saw anybody in there getting treated was myself, once after I got cut by some broken glassware and kim, and another time when I slipped and fell on an icy staircase that hadn't been fixed yet.
However, one day that changed. Rather than my twice divorced friend, Diane showed up one night. We got to talking and she knew that I might show up as I like to pass the time there and Bjorn was a very well read person like myself with interest that were similar. Diane on the other hand was a divorced woman about 30 years older than me but still in very fine shape.
We got talking past the time and then she offered me a ride home. We talked a bit on the way not too much as it was only about a 15 minute drive. At a light she was chatting with me and she put her hand on my bare leg to emphasize some point and of course I got a bit of an erection out of that which she noticed.
She asked me about my social life and I said that I had dated a girl in college but if Dad didn't approve of me so I let that go. She exclaimed a bit of surprise at this, as Bjorn had thought that I was gay. Which is actually pretty funny, but not surprising. I switched to cycling to give me muscles at a sport to have fun on as I was still getting injured on ballet especially my left ankle and would probably need an operation on it that may or may not fix the problem so I was probably going to have a very limited if any career in that.
I also told her that sometimes when Bjorn had asked me to babysit his kids, I would pretend to not be available when he lived across the street from my family years earlier so his sexy niece would come over and then we'd end up making out on his couch. We're snooping through their Trove of sexy Swedish lingerie and sex toys.
She thought this really funny and we ended up talking a bit. She told me she'd be there again on Friday and if I wanted to see her again I could show up there from anytime after about 2:30 in the afternoon.
On friday, I made sure that I was dressed a little better than normally not wearing cycling clothes but actually something nice and good looking. She was dressed up pretty nicely too and had gotten a haircut and some curls put into her hair. Our date was we went to dinner and a movie going Dutchess I was a bit of a poor student at that time. Around 11:30 after the movie had gotten out and we've gotten a bite to eat she asked me what my plans were for the weekend and I said that I had a bit of homework to do which I had left in her car but otherwise I was pretty free she asked if I wanted to do the homework at her house that weekend so I thought over her on proposal and said yes.
We didn't do anything on the first night and I slept in her spare room nursing a large erection thinking about her sleeping a few Doors Down and during one of my bathroom trips I got some toilet paper from the bathroom so I could masturbate and not leave a mess behind. She called out to me when I was patting back to the room and asked me if I was having trouble sleeping and I told her I was and she said I could join her. We talked a bit further I came in with the wad of toilet paper and she figured out what that was all about and said I probably wouldn't need that tonight and we started making out and before long I'm on top of her in the missionary position ejaculating into her.
We stayed awake after that chatting with me kissing and touching her and her doing the same to me. She asked me about any other things that I've done and I admitted to her that I'd had a few gay encounters but nothing recently. I told her about a boy up the street from me that I'd visit on afternoons when his parents weren't around or on sleepovers soon as basement rumpus room where I would give him oral after his parents had gone to sleep. I also told her about a guy 15 years older than me that I found by accident when I stumbled across a cruising site and we ended up carrying on an affair for nearly two years while I was in Winnipeg attending the Royal Winnipeg ballet and staying with my grandparents.
She asked if I had felt exploited or sexually abused by that last one but I told her the guy was a complete gentleman and left it up to me whether or not we were going to do anything. I also told her that I had a bit of backlash from other girlfriends that I told about this later and that ended up causing a bit of self-loathing with me and my gay encounters. I also admitted to her that I enjoyed some other kinky things like cross-dressing sex toys and colonic irrigation.
She told me that none of those things were particularly unique, and that her being a nurse she knew of a lot of people that enjoyed anal fun including enemas.
After having sex once more and falling asleep we got up moderately late the next morning and when she said she was going to go shower she invited me in, a novel experience at that point as I never had a shower with the opposite sex before.
I got down to my bit of homework the next morning, wanting to free up as much of the weekend as possible so I could spend it with her.
Diane and I talked a bit went for a walk came back and she asked me to come over to one of her dressers and she started pulling out lingerie and I thought she was going to ask me what I wanted to see on her but she was actually pulling out stuff that she thought I would look good in. And she was very right about that I like the merry widow she dressed me in although her size being a bit bigger than me didn't quite fit me except in the cups which she stuffed with nylons to give them a bit of form. Getting into bed, she took the lead and treated me like a submissive good looking little s*** and quite frankly I enjoyed the role reversal.
We carried on a bit more of that afternoon and ended up going out to dinner and then coming back home. I feel Bjorn to let him know that I was all right but I didn't know is that he had called display back then, a fairly new feature, is he frequently got calls from his dispatcher to come in and do first aid attendant jobs and he needed to know which numbers he could safely ignore. And he noticed that this was Diane's number. Me getting home in the late afternoon I got a strange look from his wife and him but no words were said. I got the feeling he wanted to ask me about where I was but I think he figured I would probably lie to him and then he'd get upset and there wouldn't be any trust between us. Which was bad as he wanted to be able to trust me enough because you sometimes asked me to babysit his two kids or at least supervise them as they were high schoolers while him and his wife went out for the evening.
Diane and I got up to quite a bit more in the ways of just regular sex and more kinky things. She gave me enemas and I her as she really enjoyed anal sex.