Boyshorts in the Dressing Room

I woke up this morning horny. Probably most guys do that, so I am not necessarily any different than any other guy in that area. I decided to put on a pair of my black lacy boyshorts because when I am horny, they take me to the next level. I love how they feel on my cock. I think it is the fact that they are so lightweight, they fit fairly loose, and the lacy part rubs my cock. Anyway, I had them on this particular morning, but ran out of time to play. I had to run into town to pick up a few things. I never wear the boyshorts under my clothes because (this may sound goofy) I don't want to be in a car wreck and have them on at a hospital. (goes back to Mom saying to always wear clean underwear in case you are in a car wreck - laughing at the thought)

Anyway, I decided I was going to play when I got back home from my errands around town, and since I was still horny I took a chance and left them on under my jeans. I finished getting ready and headed into town.

I stopped by the hardware store to pick up a few things I needed for a project I was going to do. Then I got in the mood to run by a department store to look at jeans, and just see how busy the women's section of the store was in case I might want another pair of boyshorts. I did not want to shop for boyshorts with a bunch of women in that section. I was hoping there would be no one there except for a cashier.

I got into the store, and the women's section is right next to the men's area. So, as I went towards the men's department I looked over at the women's area and saw there was no one in that area, just like I was hoping. So, I redirected my steps and headed into the women's area. I found the boyshorts right away. I picked out a pair of royal blue lacy ones in an 1 x size, which I knew would fit me fine. I am average size, (5'10, 187) but have learned that I need a 1 x in women's boyshorts to fit me. Then, I headed to the counter where a woman in her later 50's or early 60's, was working.

She said "Hi, is this all you need?"

I said "Yep, that is all for today?"

"Buying some cute boyshorts for the girlfriend or wife?" She asked.

I could have easily said "Yep", but I decided to just see what this woman might say if I responded different. So, I said "Well, this may sound weird to you, but they are actually for me."

She was startled a bit with my answer, and said "Oh really?"

I said "Yes. I am not gay, or a cross dresser, or weird, so don't get me wrong. I just think it is a bummer that women get to wear all the silky, sexy underwear that feel good against their skin, and guys don't. I have one pair of these in lacy black and I love how they feel on me."

I figured I sent her over the edge with that one, but, I just wanted to see how she would respond. It was kind of fun to test the waters, so to speak, with a woman her age. (Not that I am a lot younger than her. I am 43)

Her response surprised me. I really figured she would have the typical, tactful cashier response, something like "Well, cool", and then drop the subject. Instead, she said "Now that is an image that sounds interesting. I haven't seen a guy in a pair of those before. I have to admit it might be kind of sexy."

"Well, I don't wear them to be sexy, I just love how they feel on me," I said. "Besides, I would be worried the average woman would think I was weird if they knew I wore them. I would never tell the average woman because of that."

"Can I ask you what you mean with 'you love how they feel on you?' " She said this more quietly, even though no one else was in that department at the time.

"You want me to be blunt?" I said with a smile.

"Hmmm. Sure" she answered back.

I was hesitant, and still testing the waters, so I said "Uh, well, they feel good on my, uh, you know."

"Oh really? And, that is why you like to wear them?" she asked.

"Yep. They hold things kind of like a hand would", then I laughed.

"Interesting. I can get a visual on that too" she said.

I smiled, not knowing what to say. She was not the kind of woman that would strike me as adventurous in the sex department, so to speak. Maybe I thought that solely based on her age. She was dressed nicely, looked to be at least within 15 lbs of in shape. She was dressed up, like a professional woman would look. She didn't look like a prude, so don't get me wrong. And, she didn't look like someone that might call security on me. I felt I could easily say a few things to her about the boyshorts and get away with it, or I would not have dared saying anything at all.

She finally broke the ice, and said "So you wear them under your jeans?"

I said "Actually I don't. It is one of those things like Mothers always say 'Wear clean underwear in case you are ever in an accident and have to go to the hospital'. Well, for me I guess I don't want to be caught at the hospital wearing boyshorts. So, I just wear them around the house."

"Hmmmm, this is interesting to me" she said.

I had already paid for everything by now, and the boyshorts were in the bag with the receipt. We were just standing there talking. I could tell she wanted to continue the conversation, but it was also awkward, too.

Then, I guess she just took a chance and suddenly said "Well, if you ever want to model them for someone, let me know. I would love to see you in them."

I was stunned. Then, I said "I would be happy to model them for you anytime you want. I have never let a woman see me in them, so it might be kind of fun."

She was getting gutsier and gutsier, and she said "Well, you could show them to me now."

I thought for a second, and then said "Sure, like in the dressing room?"

She said "Yes. No one is in here, so you can go in and try them on. Then, I will come by and you can open the door and show me."

I was getting very intrigued with this older woman. I guess I didn't expect the conversation to go like it did. I figured I would make a couple of teasing comments just to see her response, then I would leave. I was actually getting very turned on by her comments. Plus, I am the kind of guy that loves to be asked to do something sexual for someone. So, this whole thing was definitely turning me on.

"Okay, I might actually enjoy doing that for you," as I smiled back at her.

We headed toward the dressing room so she could unlock one of the rooms. As she was doing so, she turned to me and boldly said "Wear them with nothing else on. No shirt, nothing but the boyshorts."

My cock jumped inside my jeans. This was my kind of woman - ornery, adventurous, and telling me what to do. My mind started racing to wondering what she would be like in everyday life. Would she be like this in a relationship? I dated a girl my age a long time ago that was always coming up with new sexy things to do. So, I found myself wondering if this older woman was like that, too.

I said "I love your comments. You are fun. Whatever you want, I will do for you." I told her that in case other things entered her mind. This way she had the freedom to just say them, knowing she was safe with our little game.

I closed the door and stripped completely, then put on the royal blue, lacy boyshorts. I never told her that I had black boyshorts on when I came to the store. Anyway, the royal blue ones fit me perfectly. My cock was 3/4 hard, and I was already leaking precum. I knew that my hard cock was going to be very evident through the lace, but I thought that she might actually like that. So, I wasn't worried at all. I then opened the door slightly in case anyone else was around and said "You ready?"

She was just outside the dressing room and came in immediately. She said "It's still safe. No one is here right now," as she slowly pushed open the door the rest of the way. Her expression on her face was priceless. She paused and then said "Oh my gosh, you are hot. I love those on you. You have a great looking body. Mmmm. If you were at my house I would tell you to wear nothing but those for me all day long."

My cock was growing even harder from the attention. I then said "Well, you give me the address and I might just do that for you in exchange for a great lunch."

"How about tomorrow? I am off all day," she said.

I was thinking "Gosh I love this woman. I love the way she thinks." I said "You got it. Write your address down and I will be there."

She said "Wear them under your jeans." Then she paused and said "I will reward you."

Gosh what a little tease she was.

She then said "One more thing. Hang on." Then she quickly looked around the corner to see if the place was still empty. After doing so, she said "I think you like being asked to do stuff. Slide the boyshorts down to your thighs. I want to see it all."

I did not even hesitate. I slid my thumbs under both sides, and slowly pushed them past my cock, then down to my thighs. I haven't said it yet, but another thing I love along with being told what to do, is the feeling of being exposed for someone. She wanted my boyshorts down to my thighs. To me, this is being exposed to her. In my mind it is sexier to be partially undressed at someone's request, than it is to be totally naked. So my cock was fully hard from me standing there exposed to her like this.

She looked back around the corner again, then quickly came back. She walked inside the dressing room with me, closed the door, locked it, dropped to her knees and started sucking me off. Her mouth felt hot and wonderful. She massaged my balls with her one hand, while using the other hand to stroke my cock in the area that was not in her mouth. She did this for about 30 seconds, then looked up at me and said "My guess is you will not last long. I think you have enjoyed our little teasing game. You can cum in my mouth whenver you are ready, so we do not have a mess, okay?"

I said "This is wonderful. I love how your mouth feels on me, and yes, that sounds great."

She sucked me so sensually that it was like my cock was a treasure to her, and she wanted me to enjoy every second of what she was doing to me. And, she was right, I did not last long until I exploded in her mouth. I probably made it about 3 minutes. The pleasure was unbelievable. Even though the blow job was short, all the tease beforehand is why I could never last. I had no idea that a few comments to a cashier could turn into something like this.

She then got up, wiped her mouth, and said "You will have to understand why I have to leave quickly. I don't want to get caught. Stop by the counter on your way out and I will give you my address. Be there around 10am in the morning?"

I said "You bet I will."

She said "Make sure you are wearing the royal blue boyshorts under your jeans. And, bring any other pairs that you have. I will make tomorrow worth your while. I am fun, a bit of a tease, a great cook, and love to reward guys who do things for me. Who knows what all I might come up with. See you then, okay?"

We exchanged phone numbers, just in case some unexpected thing came up. I then headed home, thinking about the sexy talk we had and all that happened, and wondering what tomorrow might be like.

To be continued...