Advise on Young Male

iVillage Member
Registered: 07-11-2006
Advise on Young Male
7
Sun, 11-05-2006 - 1:34pm
I posted this about 2 months ago and it is now worse. I am a 50yo female who lives in an apartment complex. We have a doorman who is a young guy who is a 22yo college student. i chatted with him on many occations and he commented on my nylons etc. LOL. Well, I was flattered that he even noticed someone my age and the conversation got into how he wore nylons too. I found this interesting and to get to the point, I invited him to my apt. to try on whatever he liked. So we get together and since we are similar in size we were able to try on a lot of things. I thought it was different but enjoyed it as did he. Now obviously during our time together we were both often nude and he was visibly arroused. i figured at some point he would either make a move on me or ask to relieve himself. He did neither. We then met many times again and did such things as shave our legs in the shower, apply nail polish, dress up etc. Now i don't have the chance to be with many 22yo's so I hoped to make this sexual but figured he would make the first move. He never did. i asked my sister who felt something was strange in that men who dress always masturbate to end things. he never masturbated. By the time he leaves, I'm rushing to get my vibrator. LOL. We even went out a few times dressed in nylons, came back and nothing sexual happened. So I finally asked him if he wanted to have sex and he stated that he enjoyed what we were doing but if I needed to relieve myself it was OK. Now that's a switch. So I figured maybe that will perk his interest. So the next time I got my vibrator and took care of myself while he watched. i asked if to use it on himself which he did for a while and while it appeard he was close to orgasming, he put it down and started painting his toe nails!!!! Now he is a fun person to be with and we have a lot of laughs. I guess I want to have more but at this point its not going to happen unless I tackle him.LOL. We get together twice a week and have been now for about 4 months. i dont think he is gay because he definetly has an erection and keeps it throughout. I dont want to end things because I do have fun and we have gone shopping together and to the salon etc.. I also feel as if he is not using me as he is not looking for sex> Any advice???
iVillage Member
Registered: 09-24-2004
Sun, 11-05-2006 - 5:05pm
Well, if he likes to wear nylons and paint his nails, maybe you don't have the right equipment for him. Despite the erection, my guess is he likes guys.
iVillage Member
Registered: 07-26-2005
Mon, 11-06-2006 - 10:19am

If you know anything about cross-dressers, the erection is coming from the thrill of wearing women's clothes, NOT from his proximity to you or your naked body.

Whether or not he's gay isn't the issue. He IS a cross-dresser, and he enjoys it, and he found someone who accepts his fetish. He's not interested in you, he's interested in your clothes.

You need to get out and find someone more age appropriate for yourself....someone who is interested in YOU, not your wardrobe.

iVillage Member
Registered: 09-10-2006
Tue, 11-07-2006 - 5:30pm
The way I see it he is looking for someone to play dress up with and paint his nails with while you want a relationship. If he did not try anything with you both nude and you using a vibrator, nothing is going to happen. I'm sure he likes you as you fulfill his fantasy but are you satisfied at it stopping there. I had a friend in college who enjoyed dressing. He was not gay and no one would ever imagine that he enjoyed wearing womens clothes. I had no feelings for him sexually and agreed to dress with him provided he did not touch me. It was fun to do but I would not make a steady habit of it. It does seem strange that he does not masturbate as he is arroused.
iVillage Member
Registered: 04-23-2004
Wed, 11-08-2006 - 8:01am

I agree with Dakine, his erection is due to the sexual


bounxh0a-1.gif picture by dillbyrd

iVillage Member
Registered: 11-09-2006
Thu, 11-09-2006 - 3:29pm
I have to respond to this because I can relate to the plight of the poster. I am almost 60 years old and about 25 years ago, I realized that I knew a male who enjoyed dressing in ladies clothes. That male was my son. I was completely unfamiliar with men who crossdressed and was stumped as to how to handle it. He had a box of thing hidden in his room that I cam across. I felt every type of emotion you could imagine (anger, dissappointment, shock). So I set out to learn as much as I could as quickly as possible. Back then it was before the internet so it was more difficult!! As I learned more about the men who dress, the thing that kept coming up over and over again was how they had to keep it hidden and that they feared a spouce or family member finding out. It was just me, him and my daugheter at home. I knew that he did this alone and probably felt embarressed about it as he never told either me or is sister. I made a decision that many people may criticize but one I felt was right. I sat down with him and told him what I found. I could see he filled up to cry and then I told him that it was Ok to dress however he wanted in the house and if he needed advise or a shopping partner, i would be glad to be there. I had spoken to my daughter and she felf the same way. i think he was almost shocked and I said to him to get the box and lets try some things on!! So when it is just us at home, he wears womens clothing and so do we!!!LOL. Sometimes he gets "excited" and we told him thats oK as well. It's normal. Now obviously I'm not in the same situation as wanting a realtionship. That would be sick. However, I can relate to the man in that he has someone to share this with. i really hope things work out and I give you credit for accepting him for who is is.
iVillage Member
Registered: 06-11-2003
Fri, 11-10-2006 - 9:22am
You are a wonderful parent. It's too bad that other parents aren't this understanding and loving. Your son is a lucky man.
iVillage Member
Registered: 11-09-2006
Sat, 11-11-2006 - 12:41pm
Thank you for your kind post. It is the type of situation that my friends and family have no clue about. I'm sure there are some people who feel it is the wrong thing to do but through the years I have come to the conculsion that it is who he is and how he feels comfortable when at home. Now we don;t even think about it as a dressing thing it has just become our life. My daughter & I made the right decision or us but it may not work for everyone.