Three Firsts In One Hazy, Crystal Clear Night by Katie_Johnny

Oh What A NightI was 20 years old, a sophomore in college, and was living in an apartment with a friend off campus for the first time in my life. No one in my circle of friends had any idea that I had always felt like I was a girl in my mind. Living in the deep south in the 90’s, it wasn’t an option to be honest with people. If you had these feelings, it would be in your best interests to store them as far back in your mind as you possibly could.

No one had a clue that I wore panties almost exclusively. I had 4 or 5 pair of boxers that I could wear if I was going to be anywhere with others that might involve sleepovers or showering in a gym or something, but even then, I often wore panties under my boxers as well. Once you wear them, and feel the fit on your body, it would be hard to not wear them if you were being honest with yourself. That goes for everyone, including all men, though most wouldn’t admit it.

I had a small collection of about 10 pairs of panties, a few bras, some stockings and pantyhose, as well as a small makeup collection. All of my lingerie was satin and/or nylon, and still is to this day. I love the slinky, shiny, girly fabrics, and love the way they felt so snugly on my hips and ass. I even love having panties ride up my crack, and I loved the gentle popping sound the elastic would make against my skin when I put my panties on and adjusted them around my crotch and ass.

My collection of panties and bras has little to do with anything, but I wanted to set the scene of where I was in life. I was unhappy internally, due to the crossed wires in my head that knew I was a girl. I found a small slice of peace and comfort in wearing girls clothes under my regular clothes. It soothed my body and mind. Overall, it made me feel more relaxed in my situation.

It was Christmas break, and everyone headed home for the holidays. I had a friend named Brad that went to a different college than me, and we hadn’t seen each other in months. We went out drinking on the beach with our friends like we always used to do, and then got in his car to head home.

We were both musicians, and his dad was an insurance broker who owned a strip of retail buildings downtown. He had a vacant building that he would let Brad use to record or practice whenever he was back home. We played together in a high school band, and I was familiar with the place. We went by there on our way home at his suggestion, and he poured us each a drink and put on a Zeppelin CD.

We sat down to talk, and we both talked shit about some of the girls at the beach and so forth. Keep in mind, though I mentioned earlier that I always felt internally that I was a girl, I was also infatuated with girls. Everything feminine was appealing to me from all angles. I had never hooked up with a guy before, and I shared my innermost thoughts and feelings with no one for fear of repercussions.

“Tracy looked fucking good,” said Brad, “I would love to get into her panties.”

I replied, “Yeah, she looked tight, just seeing her and Samantha and Faith got me horny as hell.”

I noticed that Brad subtly touched his junk through his jeans. He was looking away from me, but in hindsight, I realize he was planting seeds for me to eventually harvest.

He said, “I don’t know about you, man, but I get turned on so easily around girls that it’s ridiculous. It’s the stupid things like, I love seeing a girls bra strap on her shoulders, or her panties barely sticking out of her pants, and Tracy had both of those things going for her tonight at the beach. I was afraid of being busted having a massive hard-on in my pants when we all started dancing.”

As he said this, he made a slow, deliberate pull on his cock through his jeans, and I could see a clear outline of his relatively large dick through his pants. I tried breaking up the scorching hot conversation by suggesting we go out and smoke a cigarette. He agreed, and told me to wait outside for a minute, so I went out and sparked up.

He came walking out a few minutes later. He had refreshed our drinks, and had a joint dangling from his lips. He was smiling as he asked for a light, and I obliged. He took a few puffs, and passed it over to me. I took a few puffs as well.

He said, “It’s hard coming home and not having any of the girls from school being here, ya know?”

I took a few more puffs and agreed with him, then said, “The way I see it, this gives us a chance to hook up with some of our old friends we haven’t seen.”

“I guess so,” he said, “but I just wanna chill, get a buzz, and feel good.”

With that, he pulled really hard at his crotch, looking away from me, then said, “Let’s go back in.”

I was still smoking a cigarette, so he went ahead of me. I could hear that he put on a new CD, another Zeppelin record, Physical Graffiti. I finished my smoke, and walked inside to join him. I was pretty buzzed, and I know he was as well.

When I walked into the back office, I noticed he had turned all the lights off, except for a corner lamp at the opposite end of the room. He was sitting on the couch, and as I looked closer, I saw that he had no pants on at all. His cock was fully erect, laying on his bare belly, as he was slouched down on the couch.

“Care to join me?” he smirked, and grabbed his cock, giving it a playful tug. “Those pants were bunching up around my dick, I just needed to let it breathe a little. He continued, “If this makes you uncomfortable, I can put my pants back on.”

“It’s cool, man,” I said, trying to maintain a sense of normalcy. I didn’t want to make him feel weird, and was also quite intrigued at the site of his hard cock. I walked towards the couch and went to sit down.

“You should take your pants off, too, man. It feels so good to be freed up down there,” he said, as he sort of tugged his cock again.

*note* Keep in mind, I had only secretly cross-dressed, and imagined being with a guy before, but had never done anything with a guy up to that point in my life. I was equal parts nervous and paranoid, but there was this underlying feeling of excitement in a way, as well.

After thinking about it, I nervously said, “Alright, man, sounds good to me,” and began unzipping to pull down my jeans to awkwardly join him on the couch. It was at that precise moment that I realized that I was wearing a pair of pink floral print Victoria’s Secret Second Skin Satin bikini panties under my jeans. I had pulled my pants all the way down to around my knees when I noticed them, and quickly tried to pull them back up, but it was too late.

He sat up, looked intently at my crotch area, and said, “Hey, are you wearing panties?”

I was totally busted, with no excuse to hide behind.

“Yes,” I said sheepishly, “please don’t tell anyone,” I pleaded, “I wear them sometimes on my own, they’re really comfortable, but it’s nothing more than that, man.”

There was silence for a few seconds, when he finally said, “I won’t tell anyone, I promise. Just sit down and relax.”

I was extremely uncomfortable about what had just happened, but still, I proceeded to pull my pants back down and was pulling my panties down as well, when he piped up, “Don’t take the panties off. Leave them on, just have a seat.”

I did what I was told.

He began asking questions.

“How did you ever get up the nerve to wear panties?” he said, while casually toying with himself.

“I dunno,” I replied, “I just saw some in my mom’s hamper one day and wondered what they would feel like on my body. I always got turned on seeing girls in their panties and bras. I sometimes find it even hotter than seeing a girl naked,” I said.

This time it was me who subconsciously reached down and tugged my cock through my shimmering panties.

“So they turn you on?” he asked.

“They can sometimes,” I replied, “they grip my junk and my ass cheeks so snugly, that I can even get turned on by just walking around and feeling them move with me as I do so.”

“Do you imagine being a girl?” he asked, and I was petrified on how to respond to him.

“I’m clearly a guy, Brad, you know this,” I said, “so I guess not?”

That wasn’t enough of an answer to stop him from asking more questions.

“I know that you’re a guy,” he said, “but do you sometimes get off by imagining that you’re a girl, in your bra and panties, and hooking up with a guy? It would make sense to me if you did, since you know, you’re wearing all of that tight underwear made from all of that sexy girl fabric and all.”

I was nervous about revealing my thoughts and feelings. People we grew up around didn’t ever discuss things dealing with any sort of sex or sexuality outside of the stereotypical man/woman scenarios. I asked if there was any more of that joint left, and he said no, but he would roll another one, which he did.

He walked over to the counter in the office we were in, and began rolling. I was buzzed for sure, and I just remember sitting back on the couch, wearing nothing but pink satin panties, and being hypnotized into staring at Brad, stark naked, with his tight ass cheeks and a raging boner. I could feel my heartbeat intensifying, and felt a slight shiver in my body. His back was partially turned to me, and he kept on trying to continue the conversation with me as he worked.

“Does anyone else in the world know about this, Johnny?” he asked me, “and how often do you wear panties?”

I was rubbing my cock through my panties as he spoke, and replied, “No one in the world knows but you, and since I left home, I pretty much wear panties 24/7, to be honest.”

He chuckled, and shook his head in a sort of disbelief at what he was hearing, which made me feel very vulnerable.