Dressing Like a Lady

When compared to men's, women's clothing is much more complicated and difficult to put on.  No wonder women (and crossdressers) take so much longer to get ready.  In a previous post, I wrote about the difficulties I used to have with putting on my bras, and how Diane used to make me practice in front of her until I became an "expert" at it.  There are still times when I struggle, but those times are very rare and they usually come with a brand new bra that I'm not used to.

Bras aren't the only thing that's difficult to put on.  Another example are dresses, particularly fitted ones, that have zippers in the back.  I can't remember how many times I got myself tied up like a pretzel before finally getting the darned thing zipped all the way up to the top.  I am in good shape and fairly nimble, but a contortionist I'm not!  Just like I've done for Diane many times since we've been married, she now reciprocates and  sometimes helps "zip me up!"

Regular button down shirts are another item that still feel awkward because the buttons are reverse from men's shirts.  I suppose if I grew up buttoning all my shirts that way it would come more naturally, but it still seems a little awkward.  I wonder who decided ladies' shirts should be made this way and why?  Since I've been dressing at home all the time and become Diane's "wife", more and more of my shirts are in a women's style.  I wear them like I would any other shirt and even with male slacks or shorts.  I doubt anyone ever really notices the difference!

Men's clothes on the other hand are incredibly simple to put on.  No zippers in the back, buttons that you can fasten in no time and nothing like brassieres to deal with.

Corsets????  Well that's a whole other story!  I have a couple and have become quite adept at tightening them so that I have a very nice hourglass figure.  Naturally, when Diane laces me it helps reduce my waist even more.  But then again, corsets have this erotic allure about them don't they?  I think everyone would agree they're best enjoyed in the company of another!

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Sissy Sundays

In a little while I'm going to go shopping with Diane, something we do quite often on Sundays.  One thing about Diane is that she's very appreciative of having an understanding shopping partner to accompany her.  She's told me several times how much she enjoys it.  As I've mentioned before, no sitting on the sofa enjoying a Sunday afternoon sporting even on television for me unless it's something she's interested in.

How things have changed.  In the past, in my more masculine (but uncomfortable) days, both of us would get annoyed at the other during these shopping trips.  So much so that she would much rather go alone or with a girlfriend.  Now, I guess I'm that girlfriend.  Diane pointed out yesterday that Macy's has a lingerie sale and that we should check it out.  It's going to be one of our stops today. 

When we get back, I'm going to get dressed to the hilt and work on fixing her a nice dinner.  I'm going to be in that "1950's housewife"  mode, with a nice dress, maybe a pearl necklace, heels and a frilly apron.  I think for many married sissies, there are few outfits that make us feel more feminine.

I've also got to make some travel plans for my consulting assignment this week.  For the most part, I get to choose the hours and days that I work.  That's part of the agreement with my employer.  However, I'm really not the one who will be making my schedule most of the time.  That would be Diane.  This week I'll be gone Wednesday and Thursday so she can be with Brian.

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Sissy Punishment

I found myself in a position last night that I've only read about in erotic fiction or on other blogs:  standing in a corner dressed only in a pair of panties at the direction of my wife.  My corner time was a little delayed punishment for my behavior the other night. 

Diane referred to it as "sissy punishment" and said she would use it from now on whenever I misbehaved or acted selfishly.  When she got home, I was told to strip down to just my panties and stand in front of her as she sat on the sofa in the living room.  I wasn't totally en femme because we had plans on going out to dinner, so I only had a few articles of women's clothing to remove in addition to my slacks, shirt and shoes.  When I was down to just my panties, she explained to me why she was doing this and I was no sooner in the corner as she sat on the sofa and turned on the evening news.  "Be still and be quiet" were her simple instructions.

I wasn't there very long before her cell phone rang.  It was Brian.  It immediately occurred to me that Diane had set this all up so that I would be standing in the corner while she took Brian's previously arranged call.  After some small talk and Diane telling Brian that she was free for at least the next half hour, I had to listen to the planning of their next get-together (this Wednesday or Thursday) here at our house, and some rather intimate conversations. 

The conversation turned very sexual when Diane said "Wow....that's fucking hot" in response to something Brian had said.  I could hear Brian's voice and some of its inflections but couldn't make out the exact words.  But from Diane's side of the conversation, it was sometimes pretty easy to understand what he had said. 

For instance, shortly after her comment about something being "fucking hot", her response to one of his questions was "Yes I am....are  you hard?"  He had obviously asked her if she was aroused or wet.  It was obviously the latter when after he must have said he was very hard, she answered "very, very wet.  My panties are getting soaked."

On and on it went and I stood there with an erect penis doing all I could do to stop from playing with myself, yet totally humiliated.  I learned more about their lovemaking antics than I wanted to know.  How Brian enjoys playing with her breasts while she rides his cock when he's laying on his back.  How she enjoys it doggie style, with a hint from Diane that she would like it a little "rougher" at times. 

I am almost positive they discussed the possibility of anal sex, something I have never been allowed to do with Diane.   I can't be 100% positive, but from Diane's side of the conversation, things like "I don't know, maybe we could try it", "we'll see, maybe soon, if you promise to be careful", "no, I've never done it" or "but you're so big!"....what else could it be. 

Then, the conversation seemed to be wrapping up because Brian's wife would apparently be home soon.  They talked up this coming week where Wednesday night might be the best.  Brian must have said that he would have a surprise for Diane because she said "Oh really?  What is it?....Why can't you tell me what it is?"   She then went on to say, obviously for my benefit "Ok...I love surprises anyway.  Some people don't, but I do."

Before they said their goodbyes, Diane said to Brian "I'm still wet.  Just wanted you to know that."  There were no "I love you's", but there was some smooching over the phone before they hung up. 

"You can come out of the corner now" Diane said to me.  "Come stand in front of me."

I walked over to her and she just shook her head when she saw my stiff penis in my panties.  "Looks like my sissy wife enjoyed hearing me talk to my lover" she said as she rubbed me softly.  "Kneel down" she said as she spread her legs and revealed the black panties she was wearing.  "Kiss me between my legs.  I want you to feel the wetness.  I wasn't lying."

She wasn't.  The front panel of the panties were indeed very wet.  I kissed her through the fabric and stayed there until she pushed my head away.  "Lay on the floor and play with yourself for me" she said.  I obeyed and lay back with my knees bent and began to stroke myself with my fingers, sissy style. 

Diane stood directly over me and removed her black panties.  She dropped them right on my face. 

"Smell them" she said.  "It's the smell of a horny wife, aching for a real man."

I came in my own panties as hers lay on my face.  I could feel her wetness as my panties became soaked.

"I hope you're happy now" Diane said.  "At least you won't be surprised about my next meeting with Brian."

She truly is very diabolical. 

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Cuckold Thoughts

I feel kind of silly about the way I acted the other night.  I've promised Diane that I'd do my best not to act so childish about things in the future.  She has every right to be upset.  We knew up front that there would be some difficult emotions at times and that I would have to deal with them. 

Diane's not into physical punishments.  But last night she said I had come close to getting "slapped or spanked" because of the way I'd acted.  The talk we had last night was under much more reasonable and calmer circumstances.  I wasn't the "emotional sissy" she saw the night before.  She even teased me about spanking me in front of Brian, or even worse, having him do it for her. 

Right after she said that, she ran her hands across my smooth legs (I was wearing a pair of white ladies shorts and a flowered top) and up to my groin.  "You like that thought don't you?" she asked me.  I acknowledged that I did, but realized that the reality of it would be very, very difficult for me.  "Don't worry.  It would be hard for Brian too.  He's not yet ready for something like that" Diane said. 

I couldn't get the thought of such a scene out of my mind.  Spanked by my wife's lover, for some childish behavior.  The idea kept returning to me and each time it did, I would get aroused. 

I really wonder if faced with this in real life how I would react.  Would I run away from it?  Submit to the punishment at the hands of another man who is someone I know, although not that well? 

In many ways, my cuckolding the way it is is just fine.  But in some ways, I want to be a part of it.  Yet, I think that once you're a part of it, and you submit in the way I just described, or something similar, there really is no turning back. 

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A Surpised Cuckold

I walked into a cuckold scene Tuesday night when I got home.  No, I didn't "catch" Diane in bed with Brian, but the feeling was almost the same.

I had just returned from a meeting with the company I will be consulting for and it was shortly after 6 PM.  Diane had left me a voice message to remind me she would be home a little later than usual.  She always attends a dinner meeting during the last week of the month.

On the island in the kitchen was a note from Diane that read:

"Didn't make the bed when I left for the office today.  That's your job anyway.  Make sure to change the sheets also.  Love, Diane"

Not a big deal.  I never expected her to make the bed before she went to work.  I also didn't expect the scene I found when I got upstairs.

Once again, on the nightstand on my side of the bed was a used condom and its wrapper.  Pillows were strewn about, with two sitting in the middle of the bed amidst some crumpled sheets and two others on the floor on what is usually Diane's side.  A black nightie and matching thong panties also sat on the bed.  It wasn't the nightgown that Diane had worn the night before.

Probably the most disturbing evidence was in the bathroom, where two large bath towels lay on the tile floor.  It was evidently clear that Brian and Diane had showered together.

I cleaned everything up and changed the sheets as I was told.  When Diane got home just before 8, the sheets had already been in the wash and were now in the dryer.  I sat reading the newspaper when she came in and gave me a kiss.  "You're pretty efficient" she said, "already drying the sheets."

I didn't say anything and Diane could tell I was upset.  We didn't talk for the better part of an hour until I finally told her I wished she would have told me Brian was coming over.  This led to a sometimes heated discussion about her decision to "surprise me" rather than let me know in advance about her meetings with Brian.

Eventually, we resolved the issue.  I understand her point a view a little better now.  I apologized for the way I had acted. 

Submissive cuckolds never bargain from a position of strength.

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Spring Cleaning - A Sissy's Job

It's a very busy Monday here since I didn't do any housework this weekend and I'm gone all day tomorrow meeting with the company that offered me that temporary position as a consultant.  In addition to regular housework that I do on a weekly basis, Diane decided that this week would be a good time to start my spring cleaning.

Our house is immaculate, and I work very hard to keep it that way.  Nonetheless, Diane insists that every spring and fall all houses need a good thorough cleaning; all walls, windows and floors need to be washed, and what carpeting we have shampooed.  It's not something I'll finish today but will take me several days to complete.  "Spring cleaning is a a stay at home wife's responsibility" Diane said, adding "or a sissy's job."

It's also not something that you can do in heels, a frilly french maids outfit and petticoats.  Instead, I have rather plain looking pink hotel maids uniform with one of my favorite white pinafore aprons, white tights and some women's tennis shoes with a hint of pink that matches the dress.

I was up early this morning so that I could get dressed and started as soon as Diane was ready to leave for the office.  Before she left, she told me how much I "really looked the part" for the tasks she had assigned me.  "Instead of a consultant's job, you should have applied for a chambermaids position at one of the local hotels" she laughed.

Before she left, she lifted my maids dress to and ran her hands over my butt.  "Let me see what color panties you're wearing" she said.  I bent over a little so she could see the pink panties through the white opaque tights.  "I love your ass when it's in pink panties" she said, "Makes me want to fuck you."

Maybe tonight if I'm lucky.  But i still have plenty of work to do first. 

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Vanilla Friends

It's a quiet Saturday evening here and we're expecting some very vanilla friends over tonight in a few minutes.  We'll have a glass of wine then head out to dinner.  I wonder what it would be like to have friends with similar sexual tastes to ours.  Perhaps a few couples where the wife is dominant, or even a little bit of a mix where some of the males might be the dominant partner.

In any event, Dick and Jackie are probably the least likely to be kinky friends we have.  But one never knows I suppose.  Maybe they really go wild in the privacy of their home.  Doubt it very much though, since I don't think any even remotely sexual topic has ever come up when we've been with them.

I wonder what they would think if they knew what I'm wearing underneath my khaki Dockers and LL Bean shirt and navy blue blazer.  The sports bra Diane chose for me is hardly noticeable even without the blazer.  I love the pink color and it goes well the the pink ruffled panties I'm wearing.

If you run your hands over my bottom, you can feel the ruffles.  When Jackie arrives I know I'll be giving her a hug.  But she's the last person I'd expect to run her hands over my ass!

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Cuckolding, then Sissy Sex

The whole cuckolding dynamic seemed to intensify for both Diane and I as a result of her meeting with Brian on Wednesday.  I sat down and tried to put together a post yesterday but just couldn't seem to concentrate.  Wednesday evening was both emotionally difficult yet perversely satisfying to me.  Perhaps the most difficult thing to deal with was that Diane seemed almost blissful about the evening.

At about the time I thought they'd be halfway through their romantic encounter, my cell phone rang while I was on the practice putting green at a nearby driving range and practice facility.  Diane called and asked how I was doing and what time I expected to be home.  I told her I'd be there around 7 PM as planned.  "Eight o'clock sounds great" she said, and added an "I love you too" before hanging up.  I couldn't help but wonder if Brian had gotten there late, or if they just wanted more time together?

I haven't had the opportunity (sometimes I really wish I would) to talk with others in even remotely similar situations to mine.  I thought that after seeing Brian and having enjoyable sex with him, Diane would be more subdued, distant and probably even cold towards me in the immediate aftermath of their time together.  Wednesday was nothing like that.  Instead I got home a little after 8 PM, Diane appeared invigorated, happy and content.  Content with what had happened, but not content in that she didn't want more fun.

"Pretty yourself up upstairs and I'll be there in a minute" was what she greeted me with.  She was dressed in a dark purple satin robe I had bought her for her birthday a few years ago.  She looked like a woman who had just had sex.  A peck on the cheek and I was on my way to our bedroom.

I ignored the signs of sex that were all around.  The rumpled bed, her bra and panties that had been tossed on the floor next to what was usually my side of the bed.  There was one used condom on the nightstand, again on my side.  On a chair in a corner of the room lay the nightie I had set out for her on the bed.  I wondered if she had even used it.  I undressed and was slipping on a pink camisole with matching tap pants when I heard her coming up the stairs.

"It's your turn to get some cock tonight honey" she said with a smile, "but first, you know what you have to do."

I did know.  She went to the bed, laid on her back,  opened her robe and spread her legs.  "Go down on me and lick my well fucked pussy" she said in her most dominant voice.  She came so quickly that she held my head there for another orgasm.  I wondered how many that was for her that night?

When I had satisfied, it was time for her to have a little fun with me.  "Get ready" was all she said.  She went into our walk-in closet and got her strap-on and leather harness.  She walked back with a tube of lubricant and had me help her with the harness. 

"Get on all fours.  I want to take you the same way Brian took me tonight."  The words were sharp and stinging.  Short and to the point, they summarized the direction our relationship had taken in recent months and weeks.

No sooner had I gotten into position I heard her open the tube of lube and start applying it to her rubber dildo and then to my ass.  Laughingly, she said "I'm sorry, I forgot to make you suck it first.  I'm sure you're disappointed.  I'll just fuck you longer.  Ok honey?"

I was shocked by her attitude and by how much fun she was having, how much she seemed to be enjoying all of this.  "Ready?" she asked.  A slap on my ass reminded me that she expected an answer.  "Yes, I am" I said.  Another slap, this one much harder.  "Yes what?"  I got it right this time.  "Yes, Mistress."  I felt the tip of her cock make contact with my bottom.

Diane wasn't particularly rough.  She never is.  Sometimes, she just fucks me harder than others.  Last night was one of those times and in addition, as promised she did it longer.  She takes extreme care not to hurt me during her initial penetration and has the ability to sense when I am comfortable and begins to get into her groove. 

With her hands on my hips she told me how much she loved making love to her "wife" and how well I responded to her lovemaking.  "I thoroughly enjoy sissy sex with you terri" she told me, "and it's even better knowing how much you enjoy it as well." 

When she told me how Brian had taken her in the very position she was taking me, I couldn't control myself any longer.  I came with abandon and she slid in and out of me even harder.  "That's it honey, cum just like I did, cum like a good girl."  I collapsed but Diane had other ideas.  She pulled me back up and continued to do slide in and out of me.  The fucking continued for several more minutes until she said she had had enough.

Only then did she take me into her arms and kiss me deeply.  We had plenty to talk about before we finally got to sleep that night. 

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A Cuckold Date for Diane

"I need you to get all your housework done by early afternoon" Diane told me this morning.  "Brian will be over later in the day for a few hours.  I also need you to disappear until around 7 PM."

Keeping to her strategy to only let me know about her plans with Brian at the last minute, or even after they'd been together, I wasn't told about this next meeting until she was ready to leave for the office this morning.  As I explained before in this post, she believes I get too anxious about the whole thing in the days leading up to their meetings and, by doing it this way, I'll be less on edge. 

"Take the bed down and leave a sexy nightgown laying across it" she added.  "Make sure the bedroom looks real nice."  Brian will once again take my wife in our marital bed. 

She sensed my initial shock but knew I'd get over it.  Before I could really get going with Wednesday's housework (which I usually take care of at a rather leisurely pace) she took my hand and pulled me close to her.  "I know you would probably enjoy it more if we could be  more open about our lifestyle with Brian, and you could stay here and watch, but I doubt it will we'll ever be able to get to that point with him" she said.

She's right.  I know I would probably have a hard time at first, just watching my wife with another man.  But like everything else that's happened with us, I would get used to it and I would enjoy it.  Now that I'm required to "disappear" when Brian comes over, I really wish I could be a full-fledged cuckold in front of the both of them.

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Secretarial Duties & Financial Control

I got a job offer  yesterday.  No, it wasn't for a secretary's position, but I thought the title was a little catchy and apropos considering the discussion I had about it with Diane last night.

I got a call yesterday afternoon from a company offering me a temporary and mostly part-time position as a consultant.  They need help in an area where I had expertise.  I've been retired for awhile and with Diane doing very well, a return to work wasn't something I was planning on.  However, the offer was very, very generous and, it will probably be for a 6 to 8 month period.

When I told Diane about it the first thing she said was "Don't you think you'd be better suited for some secretarial work now that you're really getting into this wifey thing?"  There didn't seem to be a hint of humor when she said it either.  I didn't answer, thinking it was just a rhetorical question, then she followed up with a "Well?" 

"I guess I probably would" I answered sheepishly.

She then went on to say that taking the position was fine with her, but that she expected the same level of attention, the same amount of housework and domestic responsibility from me even if I was working.  The only exception would be if I would have to travel.  Otherwise, she said the decision was up to me.

Things changed drastically when I told her the salary.  She stared at me for a moment with a surprised expression and, before she turned away simply told me "You're taking it."

The next phase of our discussion truly surprised me.  She asked me how I would be paid my consulting fees, monthly, bi-weekly, etc.  I hadn't gotten into that level of detail during my discussion with the company, but told her that I thought it would be on a monthly basis.  "I want 85% of the net deposited into my checking account.  You can keep the rest.  I've been thinking about this for awhile and I think I need to have more control of our finances" she said. 

The overwhelming majority of our assets are held jointly, but we do have some separate savings and checking accounts.  But her position on this took me totally by surprise.  She knew it and tried to reassure me that I have nothing to worry about.  It's simply a symbolic thing that's "more befitting to the changes in our relationship."

There was one last stipulation.  "I like what you're doing with the blog" she said "and I wouldn't want that to suffer to much as a result of this new job."

I promised her it wouldn't.

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Tampon Time

As per my "contract" with Diane, I started my period the other day.  After I showered that morning I inserted a sanitary napkin in my panties and went about my business.  I was a little disappointed that Diane didn't say anything that day or in the days leading up to the time when I'm supposed to start.  Her little snide remarks about how I must be getting ready to start my period because I'm bitchy or moody always make me feel more feminine.

This time, there was none of that and when the day came, I just did what I'm supposed to do.  I was also very disappointed that she hadn't even noticed it in the evenings when we were changing or in bed.  I really was in a very different and down mood because of the lack of attention.

That changed this morning though.  I was up first and got the coffee going before heading back into the master bathroom.  Diane was still in bed and got up just a few moments later.  She came over to kiss me on the cheek and ran her hand down to the front of the panties I was wearing, stroked the outline of my penis and  reached down a little further.  She felt the pad.  "Too bad you have your period, I was hoping to fuck you tonight" she said.

Her touch and her words got me very aroused.  The neglect she had displayed for the past couple of days was soon forgotten. 

"You seem to be flowing heavily too.  I think it would be a good idea to use a tampon again this month.  Get me one and I'll help you with it" she said.  I went to the cabinet to retrieve a tampon and gave it to her.  After lubing a little, she slid it into my bum.  "There, that should help" she said and put her arms around my waist.  "You'll have something much nicer in there in a few days.  I promise." 

As I go about my housework today, I know it may sound strange, but I'm finally enjoying my period. 

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Sometimes the Truth Hurts

One of the positive things that came out of Diane's first affair (but only after some very difficult times) was our agreement that we would be truthful to one another and more open in our communications.  It's worked very well for us and is the primary reason our relationship has been able to grow and be what it is today. 

Sometimes however, the truth hurts or at a minimum, is difficult to hear.  The information Diane shared with me last night is an example of something that I might have been better off not knowing.  Diane told me that her good friend Linda now knows that Diane is having an affair with Brian.  Linda doesn't know that I'm aware of the affair and our "open cuckolding" as Diane calls it.  But just the fact that Linda knows that Diane is having an affair is tormenting to me. 

Initially I was aghast that Diane would share this information with Linda.  I know they are very, very close, but I couldn't believe that Diane would just come out and tell Linda.  However, Diane only shared the information yesterday after Linda told Diane she was also seeing another man.   According to Diane, Linda was asking Diane to cover for her this coming week when she was going to be seeing her lover.  Linda felt awful about reeling Diane in to her web of deception but felt that it was her best way of providing an alibi and not raising any suspicions.  To put Linda more at ease and relieve some of her anxiety, Diane told her about her thing with Brian. 

I appreciate Diane's honesty with me, but I struggle with whether or not I would be better off not knowing.  I see Linda once and awhile and we sometimes get together as couples for social things.  I'm certainly going to feel different each time we see one another now.  Even though Diane hasn't told Linda about my knowledge of her affair with Brian, I can't help but be embarrassed that Linda knows I'm a cuckold. 

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Submission and Femininity

I don't always feel more submissive when dressed in women's clothes, but most of the time I do.  I suppose I'm the product of my upbringing that women are supposed to be the weaker sex and adopt more docile and secondary roles in our society, acquiescing to their husbands  and boyfriends.  Times have certainly changed and I think there are more men like me comfortable in adopting these types of roles.  We just happen to enjoy crossdressing as well!

Diane can be quite dominant but not in a "hard" sort of way.  She's not much into bondage, heavy pain and those types of things associated with many aspects of BDSM and D/s.  There are many times when I wish she enjoyed some of these things but I totally understand that it's just not her.  Her dominance over me includes feminization along with a softer but very controlling approach, with a healthy dose of humiliation and more recently, cuckolding thrown in for variety.

That doesn't mean a sissy can't fantasize right?  Whenever I see a woman dressed in lovely lingerie or other classy feminine finery and in a very submissive pose, I can't help but dream about being in her position; at the hands of a dominant man who is ready to use me in any way he wants.  I'm there as his obedient slut, ready to do his bidding and be his toy.

Today, I came across such a photo on tumblr and wanted to share it with you.  This photo just does it for me in several ways.  I fantasize about what took place before the picture was snapped, as well as what is about to happen.  The collar, leash and bound wrists seem so well synchronized.  The mystery Dom can't be seen, yet his presence is so powerfully felt.  He tugs the leash with one hand and toys with her silky thong with another.  If she's as submissive as I am, she is probably at the point of orgasm  just as this photo is being snapped. 

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A Sissy Bimbo

The word "bimbo" is a derogatory term for a woman.  Although, there may be some women who enjoy being called that.  So is the word "sissy" when referring to an effeminate man.  Likewise, there are those of us who enjoy carrying that moniker.

The first time I was called a "sissy bimbo" was only the second time I had sucked a man's cock.  It was the second time I was with Rob.  The first time, which I related here, he called me a sissy faggot and forced me to finish sucking his cock when I started to pull away and said I couldn't go through with it.  I'm glad he did what he did.  I went back for more.

The next time we met at his house, he had laid out some things he wanted me to wear while I sucked his cock.  They belonged to his wife and they were obviously not things that she would wear around the house or in bed every day.  I even wore one of her bras and stuffed the cups with some of her panties and pantyhose to give me full breasts.  I don't remember what her cup size was, but she was very, very well endowed.  There was a blonde wig, some makeup, a tight fitting skirt and blouse, and even a little costume jewelry.

My makeup expertise then was pretty poor, but I struggled through it.  When I was done, Rob had me down on my knees and held my chin as I looked up at him.  "You look like a real bimbo" he told me.  "A sissy bimbo."

I looked up the definition of bimbo and though there are several, here's one that I believe describes the feelings I experienced when being called that: 

bim·bo/ˈbimbō/

Noun:  An attractive but empty-headed young woman, esp. one perceived as a willing sex object.

A Bimbo Look

I may not have been attractive to the average onlooker, but I know Rob definitely liked the way I looked.  I definitely felt empty headed, and I was 42 years young.   I was also perceived, and was, a very willing sex object.

I sucked Rob twice that day, the second time dressed in one of his wife's short and lacy nightgowns.  I felt like a bimbo once again.  He called me that several times, knowing that the words got me very excited.

After he had cum twice, he let me play with myself while laying on their bed.  I came in the panties I had brought with me just to make sure I didn't mess the sheets.  As I played with myself, Rob made me tell him that I loved being his sissy bimbo.  It's funny how words can get someone so excited.

I've been thinking about those words and that episode the past few days.  When I see Ken this summer, I want to dress like a sissy bimbo for him.  He already knows that I'm a very willing sex object for him.

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Caught in Panties?

Most of the sissies I've chatted with either in real life or online, or those that I've exchanged emails with, began crossdressing, or at least had an urge to do something like that, at a relatively young age.  Many relate stories about their first experiences taking place some time while they were in grammar school. 

I remember my own early experiences, the very first taking place before I really even realized there was anything sexual to it.  Years later, while I also felt sexually attracted to girls, I continued to be sexually aroused by female clothing.  Talk about confused.  I did take solace in reading somewhere that most transvestites were totally heterosexual.  I felt relieved.  But to be honest, now that I've come to grips with my own bisexuality, I really doubt that's true.  Maybe it is.   However, in my opinion (and it's not a medically professional one by any means), I think that men who enjoy dressing in female clothing definitely have bisexual tendencies and feelings. 

"Oh oh?  What was that noise?"

But that's a topic for another time.  Yesterday, a sissy friend of mine asked me if I had ever been "caught in panties", or caught dressed in female clothing by a parent, relative, friend, or anyone in a position of authority while I was young.  I can honestly say that I was never caught red-handed, although I had many, many close calls.  There were even a few times where my mother found some of my sister's panties in my room or in my drawer.  I denied any knowledge of how they got there, even going so far as to accuse my sister of planting them there as a prank. 

Looking back, I'm sure my mom suspected but never really said anything.   My sisters would tease me about it but the teasing never really got out of hand. 

I do remember however rushing around to hide things when someone came home unexpectedly.  Those close calls had my heart racing many, many times.  A few times, I had to throw my jeans or other clothes on over a bra and panties and wait until the coast was clear to take them off and put them away unnoticed. 

I think I'm one of the lucky sissies out there.  Based upon my discussions with others, many of them have been caught in either their mother's, sister's, cousin's or even wife's lingerie and the ensuing hysterics weren't that pleasant.  Perhaps looking back though, they did enjoy the humiliation!

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Sissy Summer Fun with Ken

I heard from Ken this morning.  Ken is the man I had an "affair" with until he moved to Florida after his wife retired.  I like using the term "affair" because in many ways it makes me feel more feminine.  Even though Diane knew about it, Ken's wife Cynthia didn't so in that sense it definitely was an affair. 

Ken's call this morning has me all bubbly.  He's going to be here this summer not just once, but twice.  He and his wife are going to be here in early June for three weeks and he plans on returning by himself some time in August.  To say I can't wait would be such an understatement. 

A few weeks after I started blogging I told Ken about my blog and he's been reading it pretty regularly.  This morning, as our talk turned to more erotic things, he insisted I lower my panties and play with myself, using the sissy masturbation techniques I've described before.  He ordered me to come in my panties and I did - twice.

I've go so much to look forward to now that I know when Ken will be here.  He promised we would get to spend some time together and has already told his wife he will be spending a few days playing golf with some friends.  It's an excuse that has worked for us before and hopefully will again.  He even mentioned a golfing weekend away.  I can't get that out of my mind right now, and I can't wait to submit to him again.  

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"Sissy Love"

Diane loved the bra and panty set I bought her on Friday.  She said it made her feel so sexy.  I made "sissy love" to her as she calls it several times, licking her to orgasm with each separate effort.   She had used that term some years ago when referring to me going down on her.  She thought it had a nice sound to it, but then all of a sudden stopped using it.

She started using it again one day last week and mentioned it several times on Friday night.  I asked her what prompted her to start using that term again and I didn't get an immediate answer.  She sort of shrugged her shoulders as if to say there was no real reason.  I sensed there was and I asked her again, this time looking at her directly in the eyes and letting her know that she could tell me anything, I would be all right.

Diane admitted that calling it "sissy love" makes it different than the sex she has with Brian.  It's a special thing between her and I and she wants to call it something unique, with special meaning.   Since she started seeing Brian, the contrast between the sex prompted her to start using the term again.

As she told me this, her hand was softly rubbing my penis in my panties and she could tell I was getting aroused.  "When I say it, does it make you feel more like a cuckold?" she asked me.  I told her it did and continued to get aroused.

"Do you like it when I say that?" she said.

Somewhat embarrassed but aroused I said "Yes, I do."

"Then why don't you play with yourself for me.  I'd like that" she said to me as she pushed me down on my back and kissed me deeply.

She got up and knelt beside me and slid my panties off.  "Go ahead, show me how much you enjoy making sissy love to me."

I began to stroke my penis with my fingers like a sissy does.

"Lift your pretty legs and play with yourself like a sissy" Diane said, assisting herself with a few soft touches on the underside of my penis.  It only took a few moments before I came.

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Bra and Panty Nights

Every so often, usually at the end of a very long and tiring week for the two of us, Diane would call me at the office and suggest that we have a "bra and panty night."  What that meant was that the two of us would come home, take a relaxing shower or bath and put on one of our favorite bra and panty sets and just lounge on the living room floor in front of our fireplace with a glass of wine and enjoy one another.

I'd spend much of the evening kissing Diane all over with special attention to certain body parts.  She would enjoy this immensely and get a few orgasms out of it as well.  I'd sometimes have a hard time restraining myself from coming as well, and would actually have an orgasm as I licked her.  But usually, after having had her own fill of satisfaction, she lovingly stroke my penis through the panties as she teased me with some erotic talk.

I wasn't going to blog today but about an hour ago Diane called me from her office and said "Let's have a bra and panty night tonight.  It's been a long time."

The call made my day.  It has been a long week in some ways.  She also said I could go shopping this afternoon to buy each of us a new bra and panty set if I wanted to.  I got the hint.  I think she'd be very disappointed if she didn't have something new and sexy to wear for tonight's "Bra and Panty Night."

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My Easter Dress (part 2)

This really isn't the second part of a story, I just didn't know what else to use for a title to this post.  At Diane's insistence, I'm posting pictures of the dress I'll be wearing on Easter Sunday.  I'll also be wearing a petticoat underneath, even though the dress has a flared out look.  The petticoat will make it flare outwards even more, revealing the ruffled panties I'll be wearing as well.

I didn't think Diane was serious about me posting the picture of the dress.  She wasn't kidding.  This morning she told me to snap a picture of it and post it on the blog before the day was done.  She did promise not to take a picture of me in it for the blog, so you'll have to leave that to your imagination.

Here's a picture of the front of the dress.  It's a little big for me around the waist, but there's a two sashes on the sides which tie together in the back which brings the waist in and helps enhance the puffiness of the petticoat.

Here's the back.  You can see the sashes and bow I'm talking about.  I'm not the best at tying bows by myself, so Diane will no doubt get it just right for me.  I'm also not the best photographer either!

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The Bitch Slap

Diane's not one who's into spanking or domestic discipline.  She's spanked me before but just really isn't into it to make it fulfilling for both of us.  It happens only on rare occasions, and not really when she's upset at me for anything.  Sometimes I wish she was into it, but I consider myself lucky to be able to enjoy what I have.

However, yesterday I did something that upset Diane very much.  It took place right here on the blog, at the end of yesterday's post.  I closed the post with a sarcastic "Thanks Diane" which didn't go unnoticed.  Diane reads the blog regularly but has yet to comment.  She'll comment to me at times about what I wrote and has even made a few suggestions.

My closing remark yesterday earned me a slap across the face as soon as she saw me when she got home from the office yesterday.  I heard her come in and say "Where are you?  Get over here now."  I hurried to greet her and as soon as she saw me told me to kneel in front of her and look up at her.  She reared back and slapped me across the face probably as hard as she could have.

"Don't you EVER be fucking sarcastic with me again" she screamed at me.  "Either in my presence or anywhere else.  If you do, I'll bitch slap you so hard you'll feel it for weeks."  She finished it off with one more slap, this time a backhanded one. 

I apologized to her profusely and have removed those sarcastic words from the post.

And let me publicly apologize as well.  There was no need for that comment at all.  I promise never to do anything like that again.

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Cuckold Conversations

Diane talks to Brian most every day.  Sometimes, if he's free in the evening they'll talk on the phone.  She's already told him it's okay to text her to see if he can call.  That's one of her ways to make him think I am "clueless" that they are having sex with one another.  After these phone call rarely will she volunteer what they've spoken about, but if I ask her, she'll usually tell me.

They had a phone conversation last night that lasted about fifteen minutes.  She wasn't very talkative after so I asked her if something in the conversation had upset her or if she was planning on seeing Brian anytime soon.  By  now nothing she says should surprise me, but again, I didn't expect to hear what she told me.

She's thinking about not letting me know too far ahead of time when they're going to get together.  She thinks it causes me too much "unnecessary anxiety" and it's just not good for me.  Instead, she believes that letting me know the day of their meeting, just before, or in some cases even after they've been together.  "It'll be much less stressful for you dearie" she said with a laugh.

Now, instead of having a little anxiety from the time she tells me until after they've met, I feel it all the time; never knowing if a meeting is just around the corner or taking place while we're apart.

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Sissy Masturbation and Milking

It has been a very long time since I played with myself using the method I'd used for so many years.  Specifically, like most other men, I would grasp my penis in my right hand, wrap it around the penis and begin stroking up and down.  Sometimes I would also hold a soft pair of panties in my hand to provide a different sensation.  But for the most part the grip, motion and sensation was the same.

All that changed a few years ago when Diane had a different plan for me.  There would be no more "closed fisted pumping" for this sissy. 

Instead, Diane's milking would consist of softly running her fingers and massaging the underside of my cock, with special attention to the area directly below the head.  Sometimes, she would also grip it a bit more firmly by securing it with her thumb as well.  From that point on, I was told that I would no longer be able to use the closed fisted method, instead rubbing my cock with middle and pointing fingers on my right hand.  It was what Diane called the "sissy masturbation" technique.   No doubt, it is much more feminine and sensually soft than what I had done before.

Two things happened in the past couple of weeks that reminded me of the change and prompted me to write about it.

First, I had struck up an online conversation with another sissy who is in a very similar situation as I am, living as a sissy wife for his dominant wife.  Surprisingly we discovered that our masturbation techniques were very, very similar.  My friend "D" also finds this method to be much more feminine and like me, suffers the embarrassment of having to do this in front of his wife.

The second incident which prompted me to write about it happened a few days ago when I read a post on the Chris Bellows Bedtime Reader blog.  Chris Bellows is a nom-de-plume for an erotic writer whose works focus on pretty hard core D/s with plenty of Female Domination.  I think he's a very creative writer and I suggest you check out his blog.

The post I read prompted me to go back and look at an earlier posting it referred to which had a link to a very erotic video of a Mistress milking a male.  The method by which she performed the task was shockingly similar to what Diane uses on me.  It's a sensual process (not always slower though depending on my state of arousal and her verbal teasing) for both parties, particularly compared to the way I used to masturbate.

To paraphrase Diane,  "The hard pumping with your full hand is the way real men masturbate, not sissies."  It's one of many ways she likes to point out that I'm different.

I'm sure most men prefer the more common method, but for sissies like "D" and I, sissy masturbation fits us so femininely well.

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My Easter Dress

Several years ago, Diane had me buy a little girls dress online from a department store.  She figured if I bought something in a "Girls Plus" size it would fit me pretty well.  She was correct.  The yellow dress with the floral pattern fit me very well, even though it was a little tight.  To finish off the dress, she had me buy a petticoat from another website that specializes in clothing for crossdressers, and it was, and still is one of my favorite outfits.

A few months after I got the dress, my responsibilities at work changed dramatically and I ended up working long hours and working out less.  I put on some weight and the dress no longer fit well.  I took a couple promotions and things got worse insofar as my weight (I wasn't fat or obese, but had put on a few excessive pounds for the first time in my life).  These past couple of years, all that weight and then some is gone and I am once again slim and trim. 

Today, Diane surprised me by taking the dress out of the closet along with the petticoat and had me try it on.  It fit better than when I bought it.

"Guess what we're wearing this Easter?" she asked me in a very condescending tone.  "Wouldn't we love to show off our sissy petticoats" she continued.

She had me curtsey for her and spin around so the petticoat could reveal my panties.

"I think some ruffled panties will be in order also.  And I think you might want to post a picture of your outfit on your blog."

Now she really had me blushing.

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