Lingerie is Introduced

My lady and I spent the afternoon together, drinking mimosas and being intimate.  As we lay naked in bed, warming up to the event, she told me "whatever you want to do, I'm good with it.  I just want you to be happy."  Seriously, she said that. We both knew what she meant, but we were both having trouble breaking past the barrier.

Finally, I screwed up the courage to ask if she'd like to see one of my lingerie items, not me wearing it, just seeing it.  I told her, "please, it's totally ok if you say, 'no,' I don't want to pressure you in any way.  If you're not comfortable, we won't do it, and it's not an issue."

She said that she wanted to see it, so I scampered off to my walk-in closet, and returned with a little green chemise.  I joked that the matching triangular thong would serve no purpose, and we both got a chuckle out of that. Unlike many CDs that we might read about, I'm not small of penis. She asked me to put in on, and so I did.  I fumbled at first, being so nervous.  Mind you, I've only had a few relationships in my life, but none ventured this far into my kink. Most women, in my limited survey, find this behavior abhorrent. When I finally managed to get the thing on correctly, she caressed it, and told me that I looked hot in it.  I could tell that she meant it. My erection grew at her touch and her remarks. 

What followed was simply remarkable. After playing for a bit, I asked her if she wanted to wear another of my pieces. She did.  I brought out a red one - Hey, Tis the Season, right?  She looked phenomenal in it; far better than I ever could.  Her womanly curves filled it out the way it was designed to be worn. She was radiant. We kissed, caressed and made love for a long time, and we each climaxed intensely.  Her first, of course, and then me. Both orgasms were extraordinary, by my observation and experience, respectively.

We lay in post-coital bliss, so contented, and so much more deeply in love than ever. She thanked me for confiding in her, and for trusting her to take the chance.  I thanked her for being open-minded, and for loving "all of me."  It was one of the most intense and pleasurable sessions we've ever had, and I think it was mostly because of the emotional connection - the trust and the openness - more than the articles of clothing.  

I'm so excited for the future. I don't know how far we'll go with this, but am happy for the journey. I am trying hard to introduce this whole world to her slowly, so as not to be overwhelming.  I am also trying to ensure that each step we take is one that she is comfortable with.  I'm prepared to stop at any point, and go no further, or even backtrack if need be. She is the most important element of my life.  I love her more than I ever thought possible, and I have never been happier in my life. Nothing is more important to me than her happiness, and that is my guiding light.`

Thanks for reading.

Jen

Crossdressing in the Time of Pandemic

I'm an office worker.  For nearly all of my career, that meant the daily slog to and from the office, through bad weather and traffic.  It also meant lack of direct sunlight for a couple of months on most days, because I would arrive at work before sunrise and depart after sunset.  Most of the time I've worked, I've not had direct access to the outside, and the lack of sunlight is depressing.

Since March, I've joined the countless millions who are fortunate enough to be able to work from home.  I would say my productivity has increased, because I spend more hours working, and less (i.e. none) on driving and idle chit-chat.  I also have nice, big windows in my home office, and can enjoy the outside views all day long.  

I'm also enjoying extended time crossdressing.  For the first time in my life, I'm able to spend hours upon hours in lady mode.  Most workday mornings, I shower, shave where needed, apply my make-up, bra and panties, breast forms, outer clothing, heels (love, love love heels!), and jewelry and wig.  My make-up skills are ok, not great.  My wardrobe continues to grow, and now with Winter upon us, I am wearing more sweater tops.  I have an array of skirts, and I love to wear them with stockings (the kind that require a garter).  In my 6" heels (with a 2" platform), I love walking around my house, feeling the softness of the nylons caressing my legs.  I am not passable as a woman; I never will be.  I'm too tall, and my face is too masculine.  But it's ok, it's not my goal.  I have to say though, that ladies clothes are so much more interesting and sexy.  It's definitely a turn-on.

How does all this jibe with my lady friend?  As I said in my first post, she loves all of me, and is supportive of me. However, she's not at the point where she wants to see me dressed that way, so out of great respect and love for her, I always revert to guy mode when we are together.  To be clear, she is a gorgeous lady - far more so than I would ever be, so there's no chance that I would outshine her. I love being the guy in our relationship.  Our romantic relationship is very good.  Our "parts" fit together quite nicely, thank you very much.  There's nothing I love more than bringing her the greatest pleasure, using every part of my anatomy.

So, for now, while I work from home, I enjoy the freedom to dress en femme as I please.  After a near lifetime of shame and embarrassment, this experience fills me with happiness and peace.

Thanks for reading!

Jen