Crossdresser caught by landlady wearing holdups

Abbie, 

I am a cross-dressing contractor who works away from home during the week. I stay with a middle-aged single woman in her spare room. Last night she knocked on my door and came in with a cup of tea, but to my horror, I was in full cross-dressing mode and wearing a pair of holdups with little else. She smiled at me, put the tea down and left the room. This evening, I got home, I found a brand new pair of holdups on my bed that were obviously hers, I slipped them on and took several photos of me wearing them, The question is should I send her the pictures or go out of my room and show her?

It sounds like you’ve already taken a bold step by wearing the holdups and taking photos. Now you’re at a crossroads, and I understand why you’re wondering how to proceed. Let’s think this through to help you make the best choice.

1. Clarify Intentions Before Acting:

The fact that your landlady left the holdups on your bed does suggest that she might be interested in seeing you wear them or exploring this side of you. However, is is risky to make assumptions without more clarity on her intentions. If you go out of your room to show her in person, you’re escalating the situation directly and intimately way, and it could lead to unexpected consequences—especially given the power dynamics of being her tenant.

2. Consider the Risks of Direct Confrontation:

Leaving your room dressed like this to show her directly could put you in a vulnerable position if she doesn’t react how you expect. Even though her actions have been suggestive, confronting her in person is a bold move that doesn’t give her much opportunity to express her comfort level at the moment. It could lead to embarrassment or discomfort for both of you if she suddenly feels overwhelmed or unprepared for such direct engagement.

3. The Option of Sending Photos:

Sending photos via a message provides more space and distance. It allows her to process what you are showing without feeling put on the spot. This approach permits her to respond on her terms and helps you gauge her reaction before deciding what to do next. If you do send the photos, make sure the message is light and invites her to communicate her feelings openly. You could say something like: are sharing

"I noticed the holdups you left for me, and I thought you might like to see me in them. I’d love to know what you think. If this isn't what you meant, please let me know, and I’ll respect that."

This type of message leaves room for her to respond honestly, whether she wants to take things further or not.

4. Respect Boundaries and Gauge Her Comfort:

While her actions may seem like clear encouragement, it’s important to remember that people’s signals can sometimes be more complicated than they seem. It is possible that she’s curious but you need to make sure she’s genuinely comfortable with what comes next. By giving her space to react at her own pace, you show respect for her boundaries and prevent any misunderstandings.

5. Be Ready for Different Outcomes:

No matter which approach you take, be prepared for different potential outcomes. She may respond positively, which could lead to a deeper or more personal connection. On the other hand, she may realize she’s not as comfortable as she thought, and the situation could become awkward. Given that she’s also your landlady, this could complicate your living situation. Consider how you would handle things if her reaction isn’t what you hope for, and whether you’re comfortable with the risks involved.

6. Trust Your Instincts:

Your instincts brought you to this point, and they’re valuable in deciding what to do next. If you feel that sharing the photos of you in holdups is a safer, more considerate way to approach her, then that may be the better choice. If you are having second thoughts or feel anxious about showing her in person, that’s a signal to take a step back and think more cautiously.

There’s no denying the excitement of the situation, but it’s important to balance that excitement with a sense of care and responsibility. Whatever you decide to do, make sure it’s done with respect for her comfort and your well-being. Taking things step by step, and allowing her room to respond on her terms, is a considerate way to move forward.

Wishing you the best of luck as you navigate this intriguing situation.