Archive for the ‘Crossdressing’ Category

When you realize that it all kind of comes together…

A few weeks ago, I had an “aha” moment when I was thinking about crossdressing and some of what makes it so pleasurable for me. I came to realize that Jennifer, in her own way, is a form of bondage.  I may not be physically restrained (though I have definitely done some scenes as Jennifer), but it’s more of a mental thing.  I typically go out without any option to easily change out of female attire, and now that I’ve started going into makeup, it’s far less straightforward than simply changing clothes.  Whenever I go out, there is almost always some element that is difficult to undo in the field, which de facto locks me into Jennifer until I get home.

How I accomplish that little bit of bondage that keeps me locked into Jennifer varies by adventure, but it’s usually something simple.  For my January trip to Pennsylvania, where I first started using makeup for Jennifer, it was the lipstick.  The lipstick locked me into Jennifer mode, because once applied, it wasn’t coming off easily, as I did not have makeup removal wipes on that outing.  In more recent cases, the bondage has been my nails.  I will typically paint my nails in a nice girly color, and that stuff is not coming off easily.  And that keeps me locked into Jennifer, since the nails would be a dead giveaway that something is up.

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Changing the way that I present Jennifer…

Ever since the local governments rescinded much of the pandemic restrictions, I began going out as Jennifer a whole lot less than I was doing.  Let’s admit – it’s fun to be Jennifer, but she has her ups and downs.  One thing that I always enjoy is doing trips as Jennifer, where I am committed to her persona for the entire trip.  In those instances, I only pack stuff for Jennifer, and so I would have to buy an entire set of clothes to get out of Jennifer’s skin, which provides a barrier to a quick changeout.  After all, Jennifer as you have known her is entirely clothing, so she can be donned and doffed in relatively short order.  However, in the past year, I’ve changed how I present Jennifer a bit.  With the pandemic measures’ subsiding, I’ve found it harder to get away with Jennifer in the form that I’ve known her.  A gold bodysuit, while fun, is harder to justify now that masks are coming off.

One thing about masks-optional, though, is that while Jennifer was previously becoming somewhat routine, the option of not having to mask injected a level of fun back into her.  Now, Jennifer was once again a special occasion.  She was something different and exciting.  Though initially, Jennifer kept her usual presentation, i.e. the gold bodysuit, as I continued to dress in the gold bodysuit for Jennifer through the end of 2021.

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A play date in drag…

There’s a certain level of fun when combining  some of my interests – BDSM and crossdressing, in this case.  A few months ago, I got to do that when visiting a friend for a little play date.  For this, Jennifer wore her slinky little red dress and black heels, and we had fun putting me in various positions on the different equipment for the camera as well as doing some light flogging and other such teasing.

Posing with a stripper pole.

Posing with a stripper pole.

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More Jennifer photos…

So it’s been a few months since last we spoke, and in that time, I’ve been going out as Jennifer about once a week.  I’ve become quite comfortable in her skin, as I feel quite confident going out and doing things while so attired.  I also now wear a pair of gaff underwear when going out as Jennifer, which works to conceal the dangly bits.  In addition, I now have a debit card with my girl name on it.  The bank knows who’s behind it, so all is well there, but now I can give people a card that says “Jennifer” on it rather than my real name, preventing me from blowing my cover, and which makes things feel just a tad more complete.

And all the while, I’m still getting photos while I’m out.  Here are some:

Standing in front of Starbucks at Tysons Corner Mall, holding up a cup of coffee.  My girlfriend described this photo as my having achieved "basic bitch" status.
Standing in front of Starbucks at Tysons Corner Mall, holding up a cup of coffee.  My girlfriend described this photo as my having achieved “basic bitch” status.

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Having lots of fun as Jennifer…

I guess that you could say, “That escalated quickly.”  Since last we spoke, I have been going out as Jennifer quite a bit, and having a lot of fun with it.  On the days that I don’t have work, when I need to go out, I’ve been putting on the gold zentai and being Jennifer.  I’ve also put some renewed effort into it, getting some new outfits, as well as new boobs.  Recall that Jennifer’s original breasts were homemade, made out of nylon stockings and rice:

Jennifer's original breasts

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Going shopping as Jennifer…

So… I believe that I have finally figured out how to reconcile the whole mask-mandate thing with the masks-are-fun thing.  With my state, Maryland, still requiring everyone to wear masks, and all of the other nearby states within a reasonable drive (i.e. DC, Virginia, West Virginia, and Pennsylvania) also now requiring masks, it required a change of strategy.  For my girlfriend and I, our original strategy was to avoid doing our shopping in the jurisdictions that required masks in order to not have to participate in the state-mandated security theater.  First we avoided our home jurisdiction of Montgomery County, Maryland.  Then masks were required statewide in Maryland, and Pennsylvania and DC shortly after that.  So we would go to Virginia to do our shopping.  That wasn’t the worst thing in the world, because I also work in Virginia, and would couple grocery runs and other shopping trips with work when I could, and we would also make other trips to Virginia if we needed to.  We got to know Northern Virginia much better for this, and that wasn’t a bad thing by any means.  Then at the end of May, Virginia started requiring masks as well.  So we started going out to West Virginia, in the Charles Town and Martinsburg areas.  Then West Virginia joined the mask bandwagon, which meant that everyone within reasonable driving time required masks.  This was followed shortly thereafter by a flurry of companies enacting their own policies requiring masks to shop.  So I was thinking, well, crap, as my girlfriend and I were more or less boxed in on this if we actually wanted to shop.

Then I had an idea: Jennifer.  The way that I figured, I might as well have a little bit of fun with it and be Jennifer when I go shopping.  In order to do this, I had to make some modifications to how I did Jennifer.  I also am a lot smaller than I used to be, as I underwent weight loss surgery last December.  As a result of that, Jennifer looks a bit different now than she did when I last showed her off to you in 2018.  So for this adventure, first and foremost, I got a new zentai – one with open eyes.  I needed to be able to see in order for Jennifer to go shopping, as I’ve complained before about not being able to see well through the original flesh-toned suit.  I eventually found a shiny gold-colored suit by Wolf Unitard on Amazon that had open eyes.  It didn’t look as natural as the original suit (which still fits) did, but it worked for my purposes.

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So Jennifer also did some bondage modeling…

When I became Jennifer to show off the back bedroom in the previous post, it was also something of a play session with a friend.  This was my first time getting tied up in far too long, and my first time doing so as Jennifer.  I wasn’t quite sure what I wanted to do with the photo for the previous post, and was considering using multiple photos, so we did a lot of different poses.  I ended up using only one photo, because the post focused on hardware, and Jennifer was really only there for eye candy.  To use multiple photos of a model in various poses in a post about housing and other hardware would have made for a major tangent.

So here are the various other poses, starting with holding the spoon:

Jennifer poses with the spoon in the dungeon room

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I have a house, and now to get a little bit of dungeon equipment…

My, what a year it’s been.  Since last we spoke, I bought and furnished a townhouse in the Maryland suburbs of Washington DC.  It has four levels, which means plenty of space for my girlfriend and me.  We each have our own bedrooms, with my bed in the master suite, and her bed in the finished basement.  That meant that the spare bedroom was upstairs, and thus, my dungeon is in an upstairs bedroom.  In my last post a year ago, I remarked, “After all, I could have a dungeon in an upstairs bedroom, but it wouldn’t be the same.”  Funny how things work out, as the play space ended up going upstairs.  But I think that an upstairs dungeon will work out pretty well, because the room has lots of other desirable features.

Here’s the room as it stands now, with Jennifer modeling:

Jennifer shows off the new dungeon room.

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Jennifer’s night on the town…

I don’t get nearly enough opportunities as I would like to go out as Jennifer.  Thus far, I’ve gone out as Jennifer four times: twice at BDSM events last year, once in June for photos at Pen Mar Park, and most recently, once in Washington DC on Halloween.  For this most recent outing, I was really debating whether I wanted to go out as Jennifer on Halloween, because I’ve always contended that Jennifer is not a “costume” similar to the way people dress up on Halloween.  This is an expression of a different side of my personality, and runs far deeper than merely dressing up.  Ultimately, I decided to go for it, because I had the night off of work, and I figured that this would be as good of an opportunity as any.  I went with a very close friend and play partner, and our original plan was to walk around the Tidal Basin near the National Mall, and visit the Jefferson, Roosevelt, and Martin Luther King, Jr. Memorials.  The way I figured, this would be a nice, pleasant walk around the memorials, and I get some more time as Jennifer.  Plus I could rock my purse, which I had not done before.

Getting down to the Mall, we decided to go into East Potomac Park to make the change.  My rationale was that the somewhat remote location of the park would provide me with additional cover to make the change.  However, the more remote location also meant something unexpected: critters.  East Potomac Park had raccoons running through it at night.  My friend even found one in the ladies’ restroom – eek!  We didn’t linger in the restroom, because critters, so I ended up changing in the car, and then drove to another parking lot closer to the Jefferson Memorial.  There, the hood on the zentai went up, and my transformation into Jennifer was complete.  Jennifer wore a teal-colored dress with knockoff Ugg boots (“Fuggs” as I call them) from Payless.  Definitely a fashion plate.

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Finally, some Jennifer photos…

I finally got some photos of my “Jennifer” persona for you to see.  It took a lot longer than I wanted to schedule an opportunity to do these, but I suppose that good things take time.  I could have done this a lot more quickly, but I didn’t want to do them at the house, out of concern that someone might recognize my decor from other Internet projects.  Since this shoot was to be “vanilla” in nature, my friend and I went up to Pen Mar Park in Washington County, Maryland and did the photos in the great outdoors.

As per usual, Jennifer is created by putting on a bra, adding breasts made from rice (I am eventually going to replace those with silicone, but rice works for now), and then adding a skintone zentai over it.  The wig and the (embarrassingly cheap) jewelry are also standard for Jennifer.

We did the shoot using two different outfits.  The first outfit was a navy blue sheath-style dress with a tan sweater and tan sandals, which we shot against a wooded backdrop:

Jennifer in blue sheath dress and tan sweater, with tan sandals.

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