Almost there!

i think she is exploring the LS.& she will proceed at her pace, as she feels more comfortable.

she may be, subtlety, testing your patience, & tolerance.
Yes, she does want to make sure that I am having a good time and tells me that she really enjoys seeing my excitement. And her LS explorations have proceeded very slowly, but continually -- I mean baby steps for sure, but at this point some of the early baby steps have become quite comfortable and enjoyable for her as well. At first, she tells me that she had to steel herself against any trip to the sex club, and did it to please me but also with great anxiety (which she did her best to hide from me). Now, the anxiety is gone from that type of adventure and she is able to relax and enjoy it, really reveling in the opportunity to dance and coyly reveal her breasts and body (though she was really super anxious and excited and nervous when we try something new). So one step at a time as she grows and becomes comfortable. I am so happy and lucky that her spirit and attitude are so positive!
 
I am so excited that we have turned a major corner with this adventure. 1. Objectively, she really enjoyed her experience with another man; 2. She allowed another man to caress and kiss her breast. She had done that once before, but it had not been a positive experience, and I was nervous that if this time did not work, well, it might mean the end to any future efforts; 3. Deb allowed another man to caress her pussy; 4. Deb allowed another man to penetrate her pussy with his fingers.

She enjoyed it!

So, to continue the story -- over the next few days, it was really strange – we did some reflecting on the adventure as I always strive to maintain open communication. As each day went by, she was less and less enamored of the entire experience. In fact, when I asked her what she enjoyed most, she emphasized the massage itself, and the pampering and the overall feeling of muscle relaxation. So strange to me, given what I witnessed, and what she verbalized out loud immediately afterwards. I keep wondering how this is possible. Was she in the same room that I was? She clearly loved it so much, and clearly loved not just the muscle relaxant but also the sexual stimulation. One thing she told me is that she often could not tell which man was touching her where, and she enjoyed that feeling of anonymity as it freed her from worrying about connecting with another. In fact, I think she saw the overall experience as a way that she and I could express and experience our love for each other. In a way, that is how I experienced it also – I love her so much when she is experiencing pleasure at that hands of another man. But I really don’t understand how her perspective changed so much after only a few days.
 
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Another chapter – the “Almost” title of this thread still works: Deb agreed to another meet-up, and she wanted the experience to be exactly like last time. One of my great hopes was that this time around would be less “clinical” and anonymous, so I suggested that we have a glass of wine beforehand. She agreed (!) and I met R in the hotel lobby. When we returned, there she was, sitting in the center of the couch with her hair pulled in front of her shoulder in the way that she does when she wants to feel beautiful (she has long, light brown hair), wearing a lovely sleeveless top with buttons, one of which was already undone, and short shorts that revealed long, smooth legs.

After some casual chitchat, I caressed her upper arm. Good bulls tend to be patient, awaiting signals from the couple, and R was keeping good eye contact with Deb and me. H put his hand on her thigh and commented on her beautiful legs. As he began to squeeze and caress her thigh, Deb just continued our normal conversation. At each step, R was waiting for me to take the lead. I began to caress the side of her breast through the fabric. I explained to R that this was one of my favorite places on her body, and one of the first places that I touched her when we began dating. Even now, this touch recalls that moment for the two of us. Deb nodded her head in agreement. With this encouragement, R began to caress Deb‘s other breast, first the side, then reaching over to her nipple, which he squeezed gently between his fingers. R took his fingers and touched her neck above the buttons, gradually moving them lower, opening buttons. He pulled the fabric aside to reveal the side of her breast. It was such a thrilling sight for me to see her exposed by another man.
 
OK, here is the rest of the adventure from our night with R:

As he caressed her breast and squeezed her nipple, I unbuttoned the rest of her blouse, opening her beautiful breasts to the fresh air. I kissed and nibbled on her left breast, and R, joined on her right. I asked Deb if she felt nice. She nodded her head, “yes.” I love asking her this question, because she is doing all of this for me (so she says), and I want her to consciously express those moments when she is experiencing pleasure, and not just be “OK” with it. I took a step back, reveling in the experience of another man ravishing her. I kissed her deeply as R continued to suck her breast. I unbuttoned her jeans and she lifted her hips so I could remove her pants and panties. R wasted no time, sliding his hand along the inside of her thigh, and then caressing her pussy with his fingers.

Deb requested a blindfold, adding mystery to whose hands were offering which particular touch. He and I continued to suck on her breasts while he stimulated her pussy. This was great! She held my hand firmly, aware that her pleasure was coming from another man and wanting to maintain contact with me. It was a wonderful moment of closeness.

We moved to the bed, and R continued massaging her pussy and kissing her breast. Deb is sometimes resistant to fingers in her pussy, especially if they are rough, so I asked her again, “does it feel nice?” She said, “Yes,” but with one of those barely audible responses that made clear that she could barely summon the strength to respond. She reached for my cock, oh, what an exquisite feeling. A few minutes later, R and I swapped and I slapped my cock against her pussy. Soon she reached her hand down to rub my cock against her. Deb does not masturbate, so rubbing my cock against her clit is the closest that she comes. “Would you like a vibrator?” Over the last few years, a vibrator is the only way Deb has been able to orgasm. In almost no time, Deb was moving her hips up and down against the vibrator, moaning, and expressing her pleasure. Her breast continued to be filled with goosebumps as R caressed and kissed her other breast. I slid the vibrator up and down until she said “there, right there.” Soon, she was writhing in orgasm, moaning and rhythmically pumping her hips in a way that she has not done in many years. All three of us were excited!

I asked Deb to turn her back to me, so that I could be close to her and hold her as she released from her orgasm, sliding my cock gently up against her pussy. This also gave R continued access to her breasts, which he held in such a gentle and comforting way, allowing Deb to feel, sexually, and physically, how wonderful she is. I noticed that Deb placed her hand on R’s forearm – the first indication of the evening that Deb recognized that her role could expand beyond being a passive recipient of the caring gestures of admiring men. Soon Deb was ready for my cock, and I happily obliged, pumping her, then stopping, then pumping her again, until I came in a furious orgasm as she moaned and pleasure. We said farewell to R as he dressed and left us to enjoy each other’s company. Deb had a wonderful, dreamy expression on her face. That is what I so love about these experiences.