The Metamorphic Power of Lingerie

My Big Mistake

I'm Raul, a heterosexual, 35-year-old male, single, living by myself in an apartment complex. I have brown hair, blue eyes, medium, well-toned build. I'm on the fifth floor and have a balcony with a nice view of a public park down below. I have two women that I have been seeing for a while, separately of course though a threesome has crossed my mind.

I have two friends, Tom and Kelly, that I have known for some time. They live together. Tom is bisexual and Kelly is a lesbian. Both of them are 29 years old and have blond hair and blue eyes. Kelly is hot and I always thought it was a waste that she was a lesbian. They recently invited me to go with them to a dress-up party night at a local gay bar that caters to men and women. I didn't see any harm in it so I agreed to go.

About a week before the party I was at their place having some wine and Kelly made a suggestion that took me by surprise. She suggested that when we go to the party I should dress to look bi/gay just to see what would happen. Tom laughed and agreed that it was a great idea. I pointed out to them that I am straight so probably shouldn't do that. They kept hammering me and after another bottle of wine, I reluctantly agreed.

Kelly said "Oh goody! This will be a lot of fun!" Tom shook his head in agreement. I asked how exactly I would dress to look gay. Kelly chimed in saying that pretty much everyone there at these parties tries to look as provocative as possible, and I should do the same. She suggested that I shave my legs, and wear some little white shorts, a short t-shirt, and a pair of high heels. I was okay with it (sort of) until she got to the high heels where I said no. More wine, more hammering, and I ultimately agreed to wear heels if she could find some for me in my size.

As the night went on we were discussing my outfit in more detail. Kelly said I needed to go to a local surf shop where they sold towels, t-shirts, bathing suits, and junk souvenirs and find myself a little pair of white shorts meant to be worn by women over bikini bottoms as a cover-up. They are made of thin material with no lining so the bikini "sort of" shows through the shorts. She said she saw them there a while back. She also said that I was to wear panties under them that were bright enough so that if someone looked they would be able to see them.

At this point, I thought this was going too far and considered backing out. But then Kelly said she was off from work tomorrow and would go with me to pick them out. Tom said "That's a great idea! Maybe you can get the high heels while you are out!" Thanks, Tom, I thought to myself. But I agreed and Kelly was to pick me up at noon. She told me to go ahead and shave my legs tonight to prepare because she wanted me to try the shorts on. She also gave me a pair of panties to wear and told me to have them on when she picked me up. They were from Victoria's Secret, part of the Darling Collection, and were very sexy and girly. They were bikini cut, had scalloped lace around both legs and the waist, had a ruched back so they fit nice and tight to your ass, and the body was stretchy material so they would accommodate my junk, which is medium-sized at best. The lace was bright red and about an inch wide, and the body was white with a pattern of red bows all over it.

Now over the years, I have done a little underdressing by wearing panties under my jeans, but I never had worn anything as sexy as these. I do like it when I wear panties, though I keep it a secret. As I held them up I felt a little stir in my groin as I thought about wearing them. I asked Kelly why she wanted me to wear them when we go shopping, and she simply said to be sure that they are visible through your new shorts. I asked did she intended for me to try the shorts on in the store, and she said "Of course, silly. How else will we know if they fit?"

With that it was getting late, so I put the panties in my pocket and said my goodbyes. Kelly reminded me to shave my legs when I got home, and I did just that using my usual shaving cream and razor. I was very careful so didn't even nick myself. After I was done and dried off it felt weird, cool on my legs, kind of sexy.

I looked over at the counter and there were the panties. I couldn't resist. I picked them up and slid them on. It was heaven! They felt so cool and silky as I pulled them into place, and they fit perfectly. I turned to see my ass in the mirror and it looked really good framed by the lace trim on the panties with the ruched back pushing into my ass. I turned around and saw my cock starting to harden and rubbed it a few times. But I knew I had to stop or I would cum in the panties and they would be soiled for shopping. So I reluctantly took them off and climbed into bed in the nude which is my normal sleep mode.

Going Shopping

The next day, right on time, Kelly called my cell phone and told me she was in the parking lot. I was wearing Khaki shorts, a t-shirt, the panties, and flip-flops. I opened the door of her car and climbed in. And was I ever surprised! Kelly is hot to begin with, but she had heavier than usual make- up on, a tank top, a very short skirt, and strappy high heels that were silver. Right away she said, "Show me your panties." So I undid my shorts, lifted my hips, and pulled them down so she could see them. This was unexpected and caused me to get a little excited. Fortunately, she just told me that she saw I liked them and that I did a good job shaving my legs.

Off we went to the mall! Once we parked we went to one of the main mall entrances and there was a Payless shoe store right there. She said, "We should look there for your shoes since they carry large sizes." We walked in and a 20-something clerk asked if we needed any help. Kelly told her we were looking for shoes for me. So of course she pointed us to the men's shoes. Then Kelly said, "Actually we are looking for some high heels for him." The clerk got a big grin on her face and said, "No problem!"

The sales clerk had me sit down and measured me using the women's shoe scale - size 12-12.5 would work. Looking at the selection, Kelly immediately found a pair of shiny, light pink 5" heels with ankle straps in a size 12.5. She said, "These should be perfect! And They will match your panties!" I almost died and the sales clerk said, "Let's try them on, shall we?"

She proceeded to hand me two of those little footies to put on and commented on how nice my shaved legs looked. Kelly was just looking and smiling. The shoes fit perfectly and they had me walk up and down the aisle a few times both so I would know how to walk in them and because I think they just wanted to watch. They coached me on how to swing my hips, one foot in front of the other... The sales clerk said, "He certainly has the legs for heels!" Kelly laughed and told her we would take them.

As I was sitting down to remove my heels and put my flip-flops back on, the sales clerk asked Kelly if I was really wearing panties. I was leaning forward on the stool and Kelly suddenly grabbed my shorts in the back and pulled them down, fully exposing my panties to the girl. She just gasped and said, "That is SO hot! I love it" I was starting to get hard at this point. Something about this entire encounter was turning me on...

We next headed down to the surf shop called Sun & Surf. It was just a few shops down so easy to get to, even with my growing erection pushing against the panties. When we got there we walked straight to the women's section for bathing suits. And there they were, the white shorts coverups. They were little. They were white. The material was thin, I could clearly see my hand through them. Kelly selected a pair in size large and held them up to me. I didn't expect that. She said, "These should work just fine."

I noticed that one of the employees who was re-hanging bikinis by a nearby changing room had seen Kelly hold them up to me and smiled a little. It was a woman, I would say mid-50s, and attractive. Kelly told me we were going to have me try them on, and led me over to the changing room by the woman. She asked for a fitting and the woman told her to go ahead into the room and pulled back the curtain. Kelly then told her that it was me trying them on, not her. The woman said, "You realize these are women's shorts, right?" Kelly nodded and pushed me into the changing room handing me the shorts. 


As I was changing I heard Kelly describing our mission to the woman, who was asking questions and was keenly interested. "You really want his panties to show through in public at this party? What if some guy hits on him? Does he wear panties often? What about other lingerie?" At some point, Kelly showed the woman my new high heels and I heard her say she would love to see me wearing them. Some of her questions were getting me a little excited as I realized the gravity of what I had agreed to do.

Another woman, similar in age and also attractive, was at the nearby cash register. She heard what was going on and said that she thought I would have a good time at the party. She said that If I like wearing panties I should try some other lingerie as well. Maybe some nighties, stockings, a garter belt. Maybe a little pegging... Then she laughed and turned to help a customer.

Kelly asked me how it was going and I told her I had the shorts on and that they were awfully small. She asked if I could see my panties through them and I told her I wasn't sure as the changing room was very confined. Then she told me to step out of the changing room. I was not worried about her seeing me, but the other woman?

So I slowly stepped out... Kelly said, "Oh! Those are PERFECT! I can see your panties very clearly!" The other woman said, "Oh boy, if you want your panties to show those shorts do it! Turn around slowly for me so I can get a good look!" So I did a slow twirl as they both watched. Kelly approved and the other woman said they looked so hot that Kelly should make me wear them home. I looked at Kelly and she said to the woman, "Good idea!" Kelly went into the changing booth, grabbed my Khaki shorts, and the woman pulled the tags off of the white shorts for me to pay with. So here I am in the middle of a mall wearing little see-through shorts and panties, and have to walk back to the car like that.

As we approached the register, that woman just took the tags, smiled, and said, "Those really are nice panties you have on. You say you are not gay, but I think you are. You just haven't been flipped yet. Those shorts and panties alone should do it. And by the way, don't forget your bag from Payless!"

My high heels! I had totally forgotten about them given all of the other actions. "Don't forget those", said the first woman. And I think he should be wearing them!" Kelly said, "Thanks for reminding us! And I agree that he should be wearing them. Can we use the bench in the changing room again? They will go so well with his new shorts and panties." So now I not only had tiny, white, see-through shorts on with bright panties underneath, but I also had my pink, strappy high heels on with my shaved legs exposed! And it was time to walk to the car.

The walk was mostly uneventful since it was late and the mall was almost empty. But some people did see me and the click-clack of my high heels was impossible to miss. It turned a lot of heads. I got catcalls from men and women, and comments about my panties and/or heels. Once three young women started following us and commenting. Kelly invited them to do whatever they wanted and one of them came up and slapped me on the ass several times while another rubbed my cock. It was a brief encounter and they left us alone laughing and taking pics as they walked away.

We made it to the car and headed to my place. Once there I implored Kelly to return my shorts but she refused. I had to walk across the well-lit parking lot, into the apartment building, and up the elevator dressed as I was. I made it unseen but the thrill of it all had caused me to get semi- erect, which Kelly noticed. Remember, she is a lesbian, so no action was expected on my part. But she took note.

She said, "It looks like you enjoy wearing panties, skimpy shorts, and high heels. Is that true?" I had to admit that it was. She then reached into her handbag and pulled out this beautiful, red lace, babydoll nightie. She said, "This is what goes with those panties you are wearing. Why don't you try it on?" I slowly took it and held it up. It was beautiful. All red lace, spaghetti shoulder straps, nice but small breast cups, very short, and a fly-away back. "You want me to wear this? Along with the panties and high heels? Why?" She pointed out that it would be fun and just for us two, and that it is clear I like soft, silky things so why not give it a try? So I agreed. What downside could there be, after all?

I was shaking in anticipation but took off my new shorts and my t-shirt and slipped it over my head. It fell into place perfectly, the hem covering about half of my panties. It felt so good that I couldn't help myself. I had a full erection at this point and she couldn't help but notice. She told me to go ahead and stroke myself since I obviously needed some relief, which I did.

As I was stroking she said to me, "You do realize that if you cum wearing lingerie and high heels there is no going back, don't you? Once you do it you will be wearing lingerie whenever you can for the rest of your life. And each time you put it on you will have to cum." And with that, I came, and I came hard. She caught my cum in her hand bringing it to my mouth and telling me to lick and swallow. And I did. I was still dazed and confused about what happened, but she patted me on the ass and told me I was a good girl and to get some sleep. I took off my heels (feet killing me) and fell into bed in my lingerie.

Preparation

I woke up the next morning with my usual woody. As I sat up I realized that I was still wearing my new babydoll and panties. The feeling of them and the thought of wearing them only served to make me harder. I saw the shoe box on the counter and figured I might as well put my heels on and jerk off while wearing my new stuff. All of a sudden Kelly's words came back to me - "You do realize that if you cum wearing lingerie and high heels there is no going back, don't you? Once you do it you will be wearing lingerie whenever you can for the rest of your life. And each time you put it on you will have to cum." Well, so far they were true.

I tried to slow down and get control of my raging hard-on by brewing a cup of coffee. It was a nice day outside so I decided to get some fresh air out on the balcony overlooking the park. I figured being five stories up no one would notice I was a guy wearing lingerie. And of course, the unexpected happened - my neighbor walked out on her balcony and was looking directly at me.

Remember the two women I told you I was seeing? Well Tina, my neighbor, is one of them. There are a few things I like about Tina. She is very attractive and has long, red hair and hazel eyes, she is 27 years old and is a runner, she is always horny, and best of all she lives right next door.

She stood there with her hand to her mouth for a minute, then said "Raul? What are you wearing? Why do you have on lingerie and high heels?" I told her I could explain and she said that she would be right over. Before I could even put on a bath robe she was knocking at the door. I let her in and she just stood there looking me up and down for a minute as her smile slowly grew. She said, "I had no idea you were into this kind of thing. I think I rather like it. Have you been doing it for long? I know you're not gay, but dressed like that some guys would be on you in an instant!"

I told her that my first time with any of this was yesterday and that I would explain. I went to the kitchen to mix up a couple of Mimosas (heavy on the champagne). As I turned around she slapped me on the ass and complimented me on it and my panties, saying that the heels really made me walk sexy. We sat on the sofa and I told her the entire story.

When I was done she just sort of nodded, having not stopped smiling the entire time, and said "Show me your new shorts. Put them on and come out here." So I did. Again her hand went to her mouth and she told me that between the shorts, the clearly visible panties, and the high heels I sure looked gay. Then she noticed that my legs were shaved and laughed. She said, "Now you know what women have to go through to have smooth legs!"

Tina was slowly shaking her head as she continued to smile. "I love the whole thing!", she said. "I have an idea. What if I join the three of you at the party? I can be your girlfriend in case you need to get away from a situation, which you will need to do if my guess is correct." I agreed and actually thought it was a good idea since at least I wouldn't seem to be a single, gay-looking, guy showing up. I said, "Let me call Kelly and Tom and see if they mind." And they didn't mind at all thinking that it would add to the fun as they already knew Tina.

Tina kept looking me up and down and soon said how much she liked me in lingerie. She started tweaking my nipples through the lace which felt really good and was turning me on. Soon my erection was returning and she said, "Somebody likes wearing lingerie and heels." She then pulled my little white shorts down and off and started rubbing my cock through my panties. I was helpless with lust. She then pulled my cock out of the right leg opening in the panties and started stroking it. I was thrusting into her hand as she did so and soon I had drops of pre-cum on my cock head. When she noticed she swirled her finger over it and pushed it into my mouth. I sucked her finger and she dropped her mouth to my pantied cock and started sucking. In no time I shot load after load of cum into her mouth, almost passing out from the intensity of the orgasm. Then she sat up and gave me a long, deep kiss pushing my cum into my own mouth. She asked me to swallow it all which I did.

Tina asked, "So how do you like the taste of cum, hun? Do you want more? Does dressing like this make you think about it?" I had to admit that element of the experience was there, though I would never plan to act on it with anyone's cum but my own. I didn't mention to her that Kelly had fed me my cum just last night.

"This has been an eye-opening and fun experience for me. I like you in lingerie and expect that the next time you come to visit me you will be dressed appropriately. And I mean without any dirty man clothes over the lingerie you will wear as you walk to my door. Understood?" This is a side of Tina that I had not previously witnessed. All I could do was agree. She got up to go home and I walked with her to the door. As she was leaving she planted another kiss on me with a full frontal embrace and firmly grabbed both my ass cheeks with her hands, slapping them as she released her grip.

I collapsed onto the sofa and tried to process what had just happened. What Kelly said was true - I wanted to wear lingerie! I wanted to wear high heels and shave my legs! But I am a man and have no attraction to other men, so why would I want to do those things? I did some research and discovered that what I am experiencing is a common fetish where men (mostly) relate wearing clothing of the opposite gender with sexual satisfaction. It is called a transvestic fetish and is quite common. It doesn't mean you are gay. It doesn't mean you want to be a woman. It means that you relate wearing sexy women's clothes, especially lingerie, with sexual satisfaction. For me, Kelly has awakened that fetish within me and I kind of like it.

The next morning, the day of the party, Tina came over to check on me. I let her in and noticed that she was wearing a silk robe that clearly exposed her nipples that were quite erect, and a pair of short-short jeans that exposed her ass cheeks. She asked me to fix us some coffee so I went in the kitchen to do so. What I didn't notice is her going into my bedroom and grabbing the red lace babydoll and putting it in her pocket. We chatted for a while and she left.