Saturday couldn’t come quick enough! When Saturday finally came (after what seemed to be forever), around 10 pm I said to my wife that I was going get ready and asked if she was still OK with me dressing up. It hadn’t been mentioned since her initial agreement. She said yes, it was fine, and she’d be up in a bit.
I’d already taken my hold-all of female clothes upstairs earlier in the day. I took a quick shower and put on my matching bra and panties set, the tan holdup stockings, the beige high heels, wig, and the satin slip.
Needless to say, I was getting excited as I sat on the bed waiting for her to join me. I heard her switching off lights downstairs and then coming upstairs to use the family bathroom. The anticipation continued to build as I heard water running as she freshened up. She knocked on the bedroom door and asked if I was ready and should she come in.
I can tell you I was VERY excited. My wife had never seen me dressed before, and I had no idea how she would react. I stood at the foot of the bed and told her to come in. I suppose it was always going to be shock for her to see her husband dressed in stockings and heels and satin petticoat, even if she was expecting it… She opened the door and did a double take, even giggling a bit, though I believe that it was out of nervousness!
She entered, wrapped only in a towel, and had a good look at me from all sides, lifted the petticoat, presumably to see if I was wearing tights or stockings, and actually commented that I looked really good!! She was especially complimentary about my legs, which I suppose were flattered by the stockings.
We started caressing and kissing and she laughed again, saying it felt so weird to feel a bra on me but by then she was getting pretty turned on herself. Once we’d had a good snog, I slipped off the petticoat and we lay on the bed together, with me in absolute heaven. We had wonderful sex and I felt great… until afterwards… I felt just a little bit silly, lying there in a wig and women’s underwear. My wife headed to the bathroom to clean up so stashed all of my female clothing.
When she came back, there was no sign of Jemma, just her familiar husband again. I asked her how she felt about the whole thing. She was very honest, saying that she could see that it was huge turn on for me, but that she didn’t get much out of it (apart from some good sex). She said what she’s said before, that she doesn’t understand what it is I see in crossdressing, why it’s such a thrill for me.
I asked if we could maybe do it again sometime but she wouldn’t say yes. She just said, I don’t know, maybe one day. It wasn’t no…
Wow I’m so glad first experience with your wife was as good as possible considering nervousness on both of you. Her being maybe unsure to continue is understandable but I hope there can be more. My wife allow only a plain black one piece swimsuit on when love making which is good with me. Otherwise she wants to keep in her mind my male image and feels uncomfortable see too much of my femme side. She’s known of Milesa for 35yrs out of 50 yrs marriage. I do go shopping about once a month fully dressed. Best to you!
You are a lucky girl. Ok, my wife does give me Saturday night to dress. But I cannot get her to come up to see me. Proud and jealous of your success. Funny thing, about 10 pm on Saturday night is when I start my transformation too. So similar to what I do. After reading this, you bring me hope. Thanks for posting this story. It is encouraging for me at least.
Abby
Dont give up. Wives can take a long time to get used to the idea. It is a bit of a shock for them! Best of luck. I’ll think of you at 10pm this Saturday! x
Thanks Jemma,
I am always optimistic but I think it may take a long time. I will be at it again this Saturday night! I do hope you are right.
Sex with your wife while dressed,what could be better? Sex again with your wife while dressed.I have only on rare occasions been able to do that and usually taking advantage of my birthday to pull it off but the thrill is well worth the wait. I’m so happy for your to have had the experience and the thrill, and your right, she didn’t say no, so there’s always the chance. My birthday is only a couple of months away so who knows, maybe it’s my turn again.
I hope you have a hapy, crossdressed, birthday Sherri! x
Sounds like it was a great experience, and a really good “first time". She might be a bit confused by making love with you looking at least somewhat feminine, with her considering herself to be straight, not bi. Hopefully you two can share the experience again! This is so difficult to explain to anyone, as we don’t understand it very well at all ourselves, so how can our wives understand? Hopefully they realize that this is an important facet to our personality, and is part of the man they love, whether or not they have realized it or not. It… Read more »
Interesting thought. Not sure I can separate the sexual side from the dressing side as it always turns me on so much! But it’s something I might suggest… Thanks Amy x
You’re so lucky to get to have “relations “ with your wife while you’re dressed I am so jealous
Well, I’ve waited a long time for that moment. I just hope it comes round again! x
I loved your story and thanks for sharing. It is so similar, it could have been written by me. Her response, all of it is identical to my wife. I will tell you that she has, on occasion, let me dress again a few times. Always if I ask, and the story is similar but at least I know do it maybe a few times a year with my wife present. I understand her side, I thnk and try not to push her at all.
Glad you liked my article Melissa, I think there are many guys out there in exactly our position. Our crossdressing sex session ahs never been mentioned since it happened, but I’m hopeful it will be repeated one day x
I truly enjoyed your story. The wonderful thing is that now you are making progress with your Wife!
Jemma Jones you are beautiful!
Indeed. Slow progress, but progress nevertheless x
While having sex is the only time my wife accepts Kathy. I love being able to have sex as Kathy with her. We have even had FaceTime sex while out of town. Feel the same as you Jemma afterwards a little silly. Then it’s back to man and wife.
Beautiful article Jemma enjoyed reading it very much. Well we’ll always have Saturday! ❤️
Yes kathy, the feeling silly immediately afterwards was a surprise. Glad it’s not just me! x
It was so cool of her to allow you this time to dress and agree to see you. I know if that had been me and my wife, she would not have said yes and if she did, she certainly wouldn’t want to see me. So congrats on her being open and supportive(somewhat). Hope it happens again soon!
Thanks Marlie. Yes, it was good of her since I know it does nothing for her. A very generous gesture on her behalf (though I’m pretty sre she enjoyed the sex)! x
The important thing is it wasn’t a no. Give her time. My wife knows about my dressing and has known since we first met. She’s seen me dressed, we’ve even gone out together with me dressed. I know she’s more open that what I think many women are but I don’t push it with her. I want her to know that she’s more important than my dressing, even though I know it’s something I want to do. If I can make a suggestion is to do something for your wife. I know with the pandemic it’s harder to do but… Read more »
Some excellent advice there Brenda. In retrospect I should have told her about my crossdressing as soon as we met, and certainly before we got married, but I was terrified of losing her. It’s all the years of secrecy that upset her more, I think, than the actual dressing. If I’d just been honest from the start she may have been more accepting and we might now be having regular girly sessions. Hindsight eh? It’s a wonderful thing…