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Hetero Male Switch, 55,  San Jose, California
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AmazonSissy

AmazonSissy - photo 1
AmazonSissy - photo 2
AmazonSissy - photo 3
AmazonSissy - photo 4
AmazonSissy - photo 5
AmazonSissy - photo 6
AmazonSissy - photo 7
AmazonSissy - photo 8
AmazonSissy - photo 9

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Friends:
tanyalove

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Straight, very tall cross-dresser with masculine features, no way I can pass. I don't want to be a woman, I get very turned on by wearing woman's clothes.

What I really need at this stage of my development is a mentor, or even a "trainer". Someone who give me a little push when necessary, give me guidance on what's appropriate and what's not, and act as protector / chaperon.

I have quite a few skills and attributes to offer in exchange for you help. I am good with computers and mechanically. Also think I am fairly intelligent and a good communicator. I have a fairly busy, but flexible schedule, and am willing to make time for this -if I find the right situation it will have a high priority.

I have some more pictures, but don't have permission to post them here (would love to have someone take some more). I can send attach them to e-mail, though.

Username:

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Height:

Weight:

Age:

Sexuality:

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 AmazonSissy

 Male Switch

 San Jose 

 California

 6' 5"

 235 lbs

 55

 Hetero

 Caucasian

 11/22/06

 12/07/21

Actively Seeking:

Dominant Transgender

Submissive Transgender

Dominant Female

Submissive Female

Switch Women

Domme/Dom Couples

Sub/Sub Couples

Femdom Couples

Friends Only

 Lives For:

 Bondage

 Breast Play

 Chastity

 Corsets

 Crossdressing

 Genital Punishment (Beginner)

 Hoods (Beginner)

 Hypnosis (Beginner)

 Objectification (Beginner)

 Orgasm Denial (Beginner)

 Pantyhose Fetish

 Stockings (Beginner)

 Strap-Ons (Beginner)

 Vibrators (Beginner)

 Female Supremacy (Beginner)

 Loves:

 Anal Play (Beginner)

 Blindfolds

 Body Worship (Beginner)

 Collars

 Electrical Play (Beginner)

 Maid/Butler Service (Beginner)

 Queening (Beginner)

 Sensory Deprivation (Beginner)

 Spanking (Beginner)

 Suspension (Beginner)

 Likes:

 Cages (Beginner)

 Canes and Crops (Beginner)

 Corner Time (Beginner)

 Dilation (Beginner)

 Exhibitionism (Beginner)

 Eye Contact Restrictions (Beginner)

 Role Playing (Beginner)

 Rubber Fetish (Beginner)

 Vacuum Stimulation (Beginner)

 Tolerates:

 Diapers (Beginner)

 Tickling (Beginner)

 Curious About:

 Enemas (Beginner)

 Local BDSM Community (Beginner)

 Outdoor Bondage (Beginner)

 Plastic Wrap

 Public Play  (Beginner)

 Watersports (Beginner)

 Cuckolding (Beginner)

 Lifestyle BDSM (Beginner)

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Journal Entries:
6/15/2016 5:08:04 PM
When my ex and I broke up, she outed me to two platonic friends of mine. We used to hang out and watch movies and sports together. It was supposed to make them stay away from me. That wouldn't have been a problem, they were more interested in each other than me.
But she told them in the context that she couldn't get off of, that I was gay or wanted to have a sex change. She didn't see the specifics of how I dress and when (which would make it obvious to anyone else that I am a sissy cross dresser) as being that significant. So if made just made my friends realize I wasn't the straight-arrow that then had assumed, but curious about what exactly was going on.


12/19/2015 1:26:39 PM
I have been separated from my soon-to-be-ex for almost two years. When we separated, she made it clear one of the unwritten terms was that she would out me to anyone she thought I tried to date. Her rationale was that it will be a public service to ensure that no other girl is fooled the way she was, despite the fact that I had never really dressed until out relationship started deteriorating and she started refusing to cater to my fetish by dressing up.
Not that that has been what has been inhibiting me from starting dating again. It's more being gun-shy after going through what I have with my ex. In fact, it might be doing a service for me, as I wouldn't just jump into dating someone until I was comfortable enough around them to open up about my secret.

9/30/2015 11:49:01 AM
I am at work alone today and I have a lot of paperwork, so I decided to dress "secretary" underneath. Black patterned tights, a tight black panty girdle, and transparent black nylon panties with lace trim around the legs.
Under my blue collar jeans, t-shirt, and boots, of course.

9/24/2015 12:14:51 PM
Laura, our mutual friend, has no idea about my cross-dressing, she just knows I have the hots for Alice. She thinks she is scaring me off with the stories, if she knew the truth, that would be the end of her telling me anything.
There are some things that happened way back that are starting to make a lot of sense now. Back when I first met Alice, Laura and I had been on-and-off friends with benefits. Laura was pissed when I quit sleeping with her after I found out that was one of the reasons Alice wouldn't date me. The fact that I did even though Alice said it didn't matter, it was too late, made it worse.
One of the other things Laura and I would do was be companions on kinky expeditions together that we didn't want our current squeeze knowing about or cramping our style. After I stopped fucking Laura, I was rewarded by having Alice tag along.
Laura was always making remarks about Alice being turned on by seeing how much she could get a guy to do without letting him fuck her. At one point, she tried to convince me that I should get a chastity belt and let her lock me in it and give the key to Alice.
I thought she was crazy, there is no way I would have considered something like that. How ironic that it wasn't that long later that I got my first chastity device for someone not nearly as attractive as Alice.

6/17/2015 8:13:14 PM
I finally got the details on the girl I have always had the hots for who was supposed to have turned her husband into a woman. It turns out it is not 100% true, but it is pretty close. I met her when she was my ex-girlfriend's roommate. She seems a little bit of a tomboy, but she actually is pretty hot.
She always dated guys that were the opposite of her, they acted like players, but also seemed a little effeminate. She ended up marrying a guy who better than most of them (as far as not hitting on everyone he saw), but I still got a way weird feeling from.
It turns out he is a transvestite, Alice knew it all the time, she has a thing for them. He would dress up and they would go out together and get guys to by them drinks. But he was straight and they would never put out.
Alice got transferred back east a couple years ago, so he quit his job and took care of the house, dressed all the time as a woman, but going out as a guy. Apparently she caught him screwing around with another woman and gave him the choice of leaving or going full-time as a girl. He now on hormones and isn't able to get an erection anymore. My ex found out because Alice is complaining about not getting fucked anymore.

4/26/2015 1:50:42 PM
We were both on temporary work assignments and in stages of our life where we our careers took precedence over our relationships, so we were more inclined the take risks and open up about our kinky secrets. (At least she was, I was pretty chicken :) )
When we first met, Leslie had trouble coming, so when I dominated her, I focused on making her come (a lot). That had the effect of making her want me to dominate her more.
So when she started dressing me up and taking the lead sexually, she tried to make up for it by making me come. But it didn't take her a real long time to realize that making me come had the opposite effect on me, I would immediately get all uptight (not that I wasn't already) and not want to play anymore. So she started focusing on keeping me on edge while she got off herself. Pretty soon, she was getting off as much or more dressing me up and dominating me as she did when she submitted to me.


4/5/2015 3:33:23 PM
My first experience wearing women's clothes was with a girl-friend who had a great collection of underwear that I was always trying to get her to wear while we had sex. She started bugging me about how if I liked her wearing it so much, I should wear it myself and see what it was like. Finally I went along and she put a pair of stockings, garter belt and a satin slip on me. She wore the same thing and it was wild, I couldn't believe how good it felt and she went kind of crazy, so I just laid back and tried to act like it was no big deal.
But it was really a life-changing experience, although I wouldn't admit it until many years later. Even though it felt great I thought I looked ridiculous with her too-small clothes on, so I pretended to go along just to humor her and even tried to get her to do extra things for me in exchange for my "cooperation".

8/14/2014 10:41:46 AM
Big news flash from an ex-girlfriend (who has no clue about my secret), her former roommate has "turned her husband into a woman!" I was too taken aback to get many details. I always had the hots for her, and she, my ex, and I had gone on some kinky expeditions together, but never dated. She had always made it clear I was off-limits because of my history with her friend.
At the time I assumed it was also because she seemed to be into the metro-sexual type of guy.

10/8/2013 11:08:50 AM

I'm not one of those guys who complains about how long it takes women to get ready, but I am getting more and more understanding. And it was worth the effort, I loved the feeling of being encased from toes and wrists to neck. My genitals were accessible through the open crotch of the body stocking, but with the chastity device locked on, all I would be able to do is go to the bathroom.

I was a little concerned about how tight I had to lace my corset to make sure it didn't show. It wasn't as tight as I had had it in the past, but quite a bit tighter than I'd normally do knowing I would have no opportunity to adjust it for several hours.

To finish up, I had to take into account that most of this trip I was going through territory where I wouldn't be comfortable showing my sissy side. Normally, I would have worn  a heavy sweater, but it was going to be too hot, so I decided on a light sport jacket and slacks. But I did get a little risque (for me at least), but only wearing a shiny nylon t-shirt and no socks. Not to mention, the restriction of the corset and the tight grip of the CB-6000.


10/3/2013 10:33:56 AM

I finally got the nerve to go to the sissy night event in the City. It wasn't exactly the kind of thing that turns me on, but it is hosted by a woman who really seems to understand the sissy fetish and gets off on it.

When I told her how nervous I was about coming, she said I should just wear a pair of panties under my street clothes. But I was so excited about the prospects of meeting her, I decided to go a little further. Then one thing led to another.

I wanted to wear one of my new corsets, I had been getting used to wearing them around the house, but it would be tough to make it up to the city and back, much less spend any time up there. So I decided to wear my trusty crossdressers corset. It is pretty utilitarian, but I was happy to discover that my training with my more severe corsets has paid off and I could lace this one up almost all the way.

Since I was going to be wearing satin panties, of course I had to put on my chastity device. My guy clothes were still going to be lumpy, so I put on a crotchless bodysuit on and then the panties.


5/27/2012 1:59:55 PM

I have had a few chances now to start my self-imposed "corset training". I have been pretty good about it so far. The first thing I did was put the smaller ones away so I wouldn't be tempted to try them until I had some practice with the larger one.

I had been very busy, but finally found a couple of hours of private time. Once again, I wore a nylon t-shirt, enough of a barrier to protect the corset, but sheer and slippery enough to not affect the fit of the corset.

I had adjusted the laces to more closely match the shape of my body, so when I wrapped it around me the busks lined right up and I was easily able to connect all the hooks. Right away I noticed it was pleasingly tight at the waist but flared out at both my hips and bust. I had expected this, since it is really made for a woman's body. And it emphasized the need for me to wear my breast forms and get some padding for my hips.
 My previous corset had been cut for a man's body, but I had decided to sacrifice comfort and utility for appearance. The big thing I had been worried about was how long it would be. My previous one had been a bit of a disappointment, even though it was cut for a man's body, it must have been a short man. So even though my new ones were the longest ones I could find, I thought that being cut for a female shape might have it be a little short. Especially since they are over-bust corsets.

I couldn't have been happier with this one, in comes from just over my nipples and ends right at my hips, close enough I have to maintain my posture or get poked when I am sitting down.

 

 


5/13/2012 2:15:15 PM

Well, it seemed like forever until I finally got a chance to try one of the corsets on, and it turned out to be little frustrating / disappointing.

Once again I only had a few minutes to myself. I knew the waist-training corset I had unpacked a couple days ago had come pre-laced. I wasn't sure about the other two, so I decided to start with it.

I was even more impressed than the first time I checked it out. It  is very heavy, satin lined with cotton. It has 24 bones. It is 5 inches longer than my previous corset, I held it up and realized that, depending where the waist point was, it could be a perfect fit.

Length-wise at least. I rushed to undress and put on a nylon t-shirt so as not to soil it. The laces were all the way tight, so I loosened them what I thought was quite a bit. But when I wrapped it around me, it wasn't even close.

So I loosened the laces up to the full width of the modesty panel and tried again. This time it was close, but I couldn't get all the clasps connected along the busk at once. The laces needed to be adjusted to better match area where I was wider / slimmer than "normal".

I've had this problem before, but in the past I rushed and forced everything closed and it messed up the corsets. I've resolved not to do it this time.

This corset is advertised as being for a 5-7" "potential waist reduction". It is a 32, my waist is just over 38". So it doesn't surprise me that it is a close fit, especially considering I'm not exactly the shape it was designed for.

So I've decided to wait until I had quite a bit more time and try one of the other corsets to start. One is a 32" and the other is a 34", I will try the 34" next.


5/12/2012 10:14:19 AM

My new corsets arrived right on schedule. Unfortunately, I did not have as much control over my own schedule. I came home from one trip to pack and leave for another and the package was waiting. I only had a few minutes of semi-privacy to open the package and check them out.

The site I ordered from had three categories, "fashion", "steel boned", and "waist training". I ordered one from "waist training" and "two" from "steel boned". Beyond that, my main criteria in choice of styles was the length, since I am very tall and these are my first true "overbust" corsets.

I had assumed the "steel boned" ones would be about the same as my previous corsets, with some improvement because of being cut for a longer torso. The minute I picked up the package, the size and weight told me all three of the new ones were much more serious than any I had previously worn.

I really didn't have time, and there was a serious risk of getting discovered, but I had to open the package. Everything was all wrapped up, so I only was able to check out the "waist training" corset for a few second, but it was obvious it was definitely going to be a big step up for me.

 


4/21/2012 6:53:53 AM

Right after I had a small cash windfall, I saw an ad for a corset sale. I have two corsets, but I have had them for a while and had decided to get a new one. But they had some really good deals, plus a 3 for the price of 2 sale, so I had to order 3.

 


4/15/2012 11:38:46 AM

Within my limitations, it's interesting how some of my biggest "phobias" turn out to be my biggest turn-ons. Stuff like being under the strict control of a strong woman, learning to wear a chastity device, wearing makeup, and being exposed to women who are normally intimidated by me are all things that really scare me and make me really uncomfortable, but are what I end up wishing I had more of afterwards.


Originally I thought it part of being tested to see if I was really committed to submitting as a sissy. I realize now there was a lot more to it. I look forward to things I used to dread were because I am being conditioned to associate them with how turned on I get by dressing.


5/18/2011 11:18:56 AM

I really love having my limits pushed. I have come surprisingly far in some ways, but there are some things I know will shut me right off.

  • being outed in r/l
  • being used to offend straight people
  • Being put in legal or physical risk

 


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