My "Time of the Month"

Last night as we lay in bed after I pleasured my wife Diane orally, I cuddled next to her as she held me close.  I have very sensitive nipples and she played with them very sensually.  I moaned softly as she touched them a pinched them a little bit.


"Are your breasts a little sore?  You should be starting your period soon right?" She asked me.

"They're a little sore" I told her.  "I'm due to start tomorrow."

She knew very well when I am supposed to wear a sanitary pad.  It was just one of her little subtle reminders of how much things have changed.

I loved it too.

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A Feminine Man

I'm not an overly masculine man or macho type by any means, but I'm not effeminate either.  There have been times where I've been made to act effeminate by Diane or a man I was with.  That's been difficult to do, but in just about every instance, Diane or the others seemed to enjoy embarrassing me that way and having me endure such humiliation. 

I think one can be feminine without being effeminate.  Being made to act effeminate in a sexually related scene of for some kinky play is one thing, but in a lifestyle, you  have to do what comes naturally to you.  I live very much as a "wife" now.  It's the way Diane likes it.  Some of the things I do are things she insists upon.  And there are others that are totally of my own volition. 

For instance, I keep myself impeccably groomed.  I'm always clean shaven and smooth all over except for the hair on my head.  I put clear nail polish on.  I weigh myself every day and always worry about my weight.  I never want to have to wear anything larger than a size 12 dress!  I also pluck my eyebrows.  These may appear to be minor things but collectively, I think they help me be a more feminine man.

I'm also very fortunate that I could retire relatively early in life.  Diane continues to work so I am more or less (actually more) the stay at home wife in our relationship.  In some ways it is quite dreamy, but sometimes it causes me a little angst and embarrassment. 

A good example of this was last week when Diane's friend Linda was stopping by after work.  It was on one of the days when I did laundry and I was getting ready to do the ironing when Diane called me to say that Linda was coming over after work for a few minutes.  I thanked her for telling me and said that I would wait to start the ironing until later that evening.  "Why would you do that" Diane asked.  Before I could answer, she told me that I was either into this lifestyle or I wasn't and she expected me to be doing the ironing when she got home.

When she arrived, I was doing the ironing just as I was told.  Linda seemed a little surprised and after saying hello said to Diane "Wow, don't you have him well trained!"  Diane just smiled and they went about their business.  I blushed and continued the ironing.  It was just another one of those things that made me feel more feminine.

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A Clueless Cuckold

Nearly twenty five years ago, my wife had an affair that nearly ruined our marriage.  At the time, I was heartbroken.  I had come close to having affairs of my own, but never did.  I was a cuckold and didn't even realize it or even know what the term mean in a D/s context.

Several years later, when Diane became more dominant over me, cuckolding became an erotic fantasy of mine.  I wanted her to find a "bull" as part of her domination over me.  She finally agreed to begin the search.  Postings on Collarme.com, Alt.com, Craigslist, PlentyofFish, Ashley Madison and a few other sites haven't produced any results to her satisfaction.  She's met several men, but is still looking.

Cuckolding is a popular topic on many Female Domination and sissy type blogs.  I envy the people in those lifestyles but by the same token, I understand Diane's reluctance to hook up with just anybody.  It also makes me wonder about her affair many years ago.  I haven't really pressed her about it, but I wonder if she was this selective back then?

At least I can say that I was a cuckold at one time.  I just wish I could have enjoyed it more.

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To Wong Fu Thanks For Everything Julie Newmar

We've had to watch about every drag movie from Some Like It Hot to Tootsie to Wong Fu. I thought that the wedding reminded me a lot of To Wong Fu. The reason is that we were so nervous that at the reception, we sort of became the party. I don't know exactly how many of the guest new we were guys and how many didn't, and a wedding that's got a large contingent of hair stylists isn't going to be the most anti-crossdressing crowd out there, but there were aunts and grandmas and uncles who met us and were at ease and fascinated. I guess having Colleen on my arm made me less self-conscious than the others in frocks.

One of the best parts of the wedding events for me was meeting Wendy's sister Jackie. Jackie is a high school student and at first I know Wendy had worries about how she would interact with us, but I think she was more interested in the fact we were in college than the fact we were in heels. She was just so enthusiastic and interested about everything. I think I was the dancing queen of the wedding. I danced with at least a dozen people of all ages, sizes, and genders.

Somebody asked me when the date for my release was coming up. After all, I started this only about 4 months after Jill. I have no illusions. That day is not coming for me as long as I date Colleen. If we break up, I'll probably get more freedom, but I really hope that doesn't happen. Knock on wood, we're doing great.

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Another Little Black Dress

I wear things besides little black dresses, I really do. Things with Colleen and I are going much better. We had a heart to heart and I know where things stand. I can't help, but feel a bit sorry for Katie and Xiu as though I love her to death, I know just how devious Colleen can be and they do seem dead set on not only feminizing Katie, but also punishing Xiu. Jill and I had to kiss and make out some, but Xiu and Katie have taken it to a whole nother level.

Wendy's wedding is coming soon and I'm scared to death about this. Her wedding is going to be very nontraditional, but families and such will be there. Within a week or so, Wendy wants us to come in so she can practice our wedding hair styles. This is going to be one bizarre bachelorette party I can say that.

One person asked about passing as a male--I can do it, but it takes a lot of work. I don't have to do it much fortunately. It's very weird to be in this situation, but I hope to eventually be in a situation like Jill is. She looks male all the time now, except when she dresses up and while she might not be quite as pretty as she was when she did it full time--she's still a very hot woman.

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Am I Crazy to be Jealous of Katie

The first six months of being a sissy were the hardest part. My God, every time I turned around, I felt like I was losing the final scrap of my masculinity only to lose another scrap the next day. Katie, like my beginnings, is not thrilled be be undergoing this transformation, but feels powerless to stop it. So why do I feel jealous?

Colleen had a talk with me before she even began dressing Katie and told me that we filled two different roles. I was her lover, her girlfriend, and at times her boyfriend. Katie was her doll and a chance to do something she's really wanted to since she found out about her brother--feminize a guy. I was pretty much already a finished product when we met.

Still, seeing her all excited about Colleen, is giving me those feelings an older sibling gets when a new baby is born. Colleen is so excited about Katie. I hope when things calm down, it'll be a bit different. I got a lot of questions last time so I thought I'd go through them.

Katy Perry - Very hot in my opinion. Very bland music that I neither hate nor love. I think her look is part of where Colleen came up with the name Katie from.

Chastity - I haven't been in it in a while except as an occasional punishment. It was really uncomfortable. It served Colleen's purpose though of reminding me who controlled me completely.

Moisturizer - Clinique Moisture Surge Extended Thirst Relief. Clinique counters are everywhere.

24/7 - Not quite, but 21/7 I'd guess. I am able to look like a guy, but it does take more work than looking like girl does now. I think this is a place where both Colleen and I are happy. Unable to look like a guy is not something I'd be happy with, but she likes that it's work for me.

Breast Forms - They're pricey for the good ones http://www.thebreastformstore.com/breast-forms-store-gold-seal.aspx

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Colleen is Such a Kink

Colleen is such a kink. I don't think she can help herself. That day that I came to the realization that the more feminine I was the more excited she was. It's weird because she had absolutely nothing to do with the decision to feminize her brother in the first place--though she certainly approved. While Jill has basic freedom to dress how she wants, if Colleen is around, she'll assert her authority to send him back into a dress. Oscar night, she came over and we all found ourselves digging out our closest approximations to Hollywood glamour to watch the show, while she sat there in jeans smiling the whole time. Aaron has become a new favorite target of hers and while he's not technically being feminized, she has no trouble using her authority over him to torment him. I asked her what drew her to putting guys in dresses and she told me she loved the power most, but the fact she had such a hottie for a boyfriend had benefits too before kissing me square on my lipsticked mouth. Yep, she's a kink alright.

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