I guess it started out by Julie telling Cathy how much she appreciated her giving me a good shopping experience today. In return, Cathy told her she thought it was really fun to help a male customer that was shopping for himself, and added she would love to do it again. Julie told her that I was starting to wear panties everyday and we were having a bit of a hard time finding panties that would hold me in all the time. At first, Cathy didn’t understand, but Julie told her that I was ‘bigger than average’ and I always seemed to have problems keeping my ‘private parts’ inside the panties, which is actually the truth.
Cathy asked what style I had been wearing and Julie told her that up to now, I had been wearing her bikini style panties. Cathy told her that maybe what I needed was something with more coverage, something bigger than a bikini. Julie told her that she liked it when I wore the bikinis around the house because it shows me off better, especially when I get hard.
I thought Julie was BS’ing me and I asked her if she really said that. She told me she did, and according to Julie, Cathy thought it was hilarious. But, Cathy also told her she totally understood, and maybe what I needed was a style I could wear to work under my regular clothes, and then some I could wear at home when it was okay to be more daring. Julie fully agreed. What I really needed, she said, was a full supply of my own undies some for work and some for play.
I was shocked when I learned she told Cathy that I might be “discovering my feminine side” and she wanted me to feel free to explore that. Additionally, she confided in Cathy that I was extremely embarrassed to shop by myself. What I needed was someone who knew about lingerie, someone I could talk to openly about what I wanted to wear and someone who would understand the sensitive nature of a man going through all of this. Lastly, Julie told her that even though I couldn’t admit it yet, she thought I needed to explore all the offerings of the lingerie department and not just concentrate on the panties.
Julie admitted to me that she stretched the truth a little bit. “A little bit?” I asked. “My feminine side? Where the hell did that come from?”
Julie reached out to put her hand over mine and said something which I totally feared. “Honey, well, it kind of makes sense, doesn’t it? You’ve graduated to wearing panties everyday, and now, you’ve bought some of your own. You’ve been enjoying the strap-on and you told me that you’ve had some bi-curious thoughts. That sure sounds a little feminine to me. Now, don’t get me wrong, Sweetie, I don’t mean any of that negatively. The truth is… I’m actually pretty damn proud of you.”
I looked directly at her. In the brief instant that it took me to replay the significant events of the last several months in my head, I had to admit that it might look that way. But, was it true? Did all this add up to mean I had a feminine side and was trying to discover it?
Julie told me that Cathy immediately volunteered to help, saying that we could come in anytime she was there and she would dedicate herself to helping me fill out my wardrobe. That was exactly what Julie wanted to hear, but, “There’s still a small problem” Julie told her.
“What’s that?” Cathy asked.
Julie told her she felt it was better if I did my shopping alone, so that Julie didn’t influence my interest and selections. “No problem,” Cathy said, “just send him in and I’ll take care of him personally.”
“That’s great,” Julie said, “But, does that mean you’ll go into the fitting room to make sure everything fits for him?” Cathy reminded Julie that men weren’t allowed in the fitting rooms.
Julie suggested she might have to go into the men’s fitting room with me. “Oh, no,” Cathy told her, “I can’t do that. It’s against store policy. If one of the men’s department associates saw a woman sales associate go into their dressing room with a male customer, I could be fired on the spot.”
Then Julie asked “Well, how about a different store, then?”
Cathy started to catch on now. She asked Julie if there would be any problem with her doing that being in the fitting room with me while I tried on different things. “I don’t see why not,” Julie answered, “If it’s standard policy across most stores to allow women that are shopping with men to go into the men’s fitting areas, I guess that will work. That is….. unless that’s too weird for you.”
Cathy asked her straight out “Let me make sure I understand this, you’re telling me it’s going to be okay if I’m in the fitting room with your husband while he’s changing clothes trying on panties? You know he’s going to be, uh, uncovered?”
“Yes,” Julie answered, “I realize that, and it’s fine with me if you’re willing to do it.”
Julie told me Cathy’s eyes lit up and she started to smile. As Julie hoped, Cathy couldn’t agree fast enough to be my personal lingerie consultant. She was beaming at the whole idea and even asked Julie if this was on the level.
“Yes, Cathy,” Julie said, “I’m being totally honest with you. I know he’s going to be exposed, but, I trust him, and I think I can trust you, too. Oh, one thing you do need to know is that he’s almost always ‘excited’ when he’s wearing panties.”
“You mean ‘excited’ as in ‘erection’?” Cathy asked.
“That’s exactly what I mean, Cathy. Would that bother you?” Julie said.
“Heck no,” Cathy answered, “that wouldn’t bother me at all, not one bit! That would be just so cool.”
“Look,” Julie added, “he knows how to take care of that if it gets to be too big of a problem. If you feel uncomfortable, just tell him. He knows what to do.”
“OH MY GOSH!” Cathy exclaimed. “That would be amazing! I swear I would be totally okay with it. I’ve never seen a guy do that, uh, all the way. Are you sure he’ll do it in front of me?”
Julie told her I had something of an exhibitionist streak in me and she was sure I would be completely willing to be naked and masturbate in front of her. She also promised she would talk to me about not being a problem and doing exactly what Cathy said while we were out.
Julie told me that Cathy was more than excited and eager to help out, in fact, now she had a lot more questions. She asked if it was okay for her to touch me while I was trying on clothes in order to check and adjust the fit. Julie told her that was fine. “Even if he’s trying on panties?” Cathy asked. “Of course,” Julie answered, “He needs to get the right size and we need to make sure his balls won’t come out of the leg holes and that his wienie will fit inside.”
“He’s bigger than average?” Cathy asked.
“Yes,” Julie said, “and that’s been part of our problem, he’s got a lot down there. When he gets hard, it’s worse, so you’re going to have to check for that and take his size into consideration when you’re checking for fit.”
“And, you’re sure he’s going to be okay with all of this?” Cathy asked. “Even, jacking off, uh, I mean masturbating in front of me?”
“It’s okay to say ‘jacking off’, Cathy, and trust me,” Julie answered, “he won’t complain a bit. He might be embarrassed at first, but that won’t last long. ”
Julie paused for a minute and then asked “Cathy, I hope you don’t mind if I ask this, but, do you have much experience with men? How old are you, can I ask that?”
“I’m 18, and no, I don’t have a lot of experience.” She sighed and told Julie that with school, working and her irregular personal schedule, she didn’t date much. “But,” Cathy said, “I’m not a virgin if that’s what you mean.”
Julie told her it wasn’t that at all, but, she was kind of surprised that Cathy hadn’t seen a man masturbate to climax before, finally telling her. “Cathy, the more you’re around men, you’ll find out they masturbate, or, jack off, a lot. So, don’t be surprised about that ever, and don’t be surprised if they want you to watch. And, I’ll tell you this…. you can learn a lot by watching them.”
“Like what?” Cathy asked.
“Well, for example,” Julie said, “how they really like to be touched. If you watch them, you’ll know how to touch them yourself. Personally, for me, I’ve never turned down the chance to watch any man stroke himself, and especially with Greg. I’m sure you’ll see what I mean. Besides, it will make him cum faster if you do.”
Finally, Cathy asked why Julie wasn’t the one shopping with me and why it seemed Julie was so willing to let me be naked and jacking off in front of her.
That was something I wanted to hear about, too, but, hadn’t asked up to now and I wasn’t about to look a gift horse in the mouth, so, I just kept my mouth shut.
“Cathy, I’m going to tell you this in confidence, okay? And this is the complete and honest truth.” Julie told her.
“Okay. I understand.” Cathy answered.
Julie told her that she loved me very much, more than any other person she ever knew. Then told her how we had been experimenting with fantasies and different kind of things to keep our sex life fresh and new. About how I had granted her two of her greatest fantasies and frankly, she wanted to allow me the chance to try out some of the things I had fantasized about. Julie didn’t want me to go out to find a hooker or a mistress to do these things, so, she decided to take it upon herself to give me these opportunities so I wouldn’t have to go somewhere else for them. She added that if Cathy was willing, she could be a part of it.
My heart sank as she spoke. Everything came into focus and I saw my wife, my darling wife, sitting there with a tear in her eye as she touched my hand and said “Greg, I do love you more than you could ever know, and what I just told you is exactly what I told Cathy and is the honest truth.”