After a lifetime of internal strife and self questioning, I determined that I’m a gender dysphoric person who has quietly felt like I was a girl for roughly my entire life. This condition has led me down many wild roads in my adult life, most of which are amazing memories, which translate into great stories, especially in bed.
Oh What A Night
I 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.
“What’s so funny about that?” I said, feeling like he was laughing at my expense, but he said that wasn’t the case.
“I’m not laughing at you, man, I just can’t believe how close we’ve been for so long and I never knew this side of you, that’s all.”
That was a fair enough response, given the circumstances. He continued,
“I mean, you’re not gay, and you know I’m not gay, so in a way, I kinda think it’s hot that you’re that in tune with yourself. I have 4 sisters, and I would be lying if I said I hadn’t touched a pair of their panties to my cock when jacking off, but I never went all the way to the point of putting them on. I was always terrified at the idea of being caught by one of them.”
I understood what he was saying. I had no sisters, but I had a very attractive mom who dressed as girly as a woman possibly could. I had two brothers and an old school dad, so there was a lot of testosterone flowing in my house.
“I didn’t get really serious about wearing them all the time until I got out on my own and knew my world was private. Then it just became my little secret pleasure,” I told him, and by now, I didn’t even realize that I was constantly rubbing my cock through my panties and it was so hard that it kept trying to burst through the satin patch.
“That’s wild,” he said, as he sparked the joint up and started walking towards me. He took a few big pulls, then stood right in front of me, his giant throbbing cock at full attention, at my eye level, and handed me the joint. I took a few pulls as well, and was trying to act like I wasn’t 100% focused on his cock. I handed the joint back to him, and he sat down next to me, this time much closer.
“Has anyone else ever touched you down there while you were wearing panties?” he asked, taking another pull off the joint, while teasing his cock with his other hand.
“No,” I replied, “I never intended to get busted wearing them, you are the first person who has ever known about this in my life.”
He then said, “Alright, come closer, I am going to do a shotgun hit for you.”
A shotgun hit on a joint is when one person turns the burning end of the joint around and puts it in their mouth, then they blow outward, and it shoots a stream of smoke into another person’s mouth. I remember “Kashmir” started playing on the CD player. I turned to him, got really close to his mouth, and he flipped the joint around and started blowing smoke into my mouth. As soon as he finished, and my lungs were at full capacity, he pulled the joint out and said,
“Now you blow it back into my mouth, get closer, baby.”
I barely noticed he called me baby, but put my lips seriously close to his and started exhaling. As I did, our lips sort of touched. At first, we both moved backwards a little bit, and we both were smiling. After 10 or so seconds, we both kept inching our lips closer and closer until they were locked. We kissed passionately and gently, all lips for about a minute. As time went by, I could feel his tongue inching its way into my trembling mouth, and he began going deeply and aggressively down my throat, and I remember me locking my lips on it, sucking it like it was a cock.
At that moment, I felt his hand on my crotch, rubbing my dick through my panties. It was like nothing I had ever felt before. My entire body was tingling, and I was breathing heavier than I ever had in my life. My instinct was to grab his almost cartoonish looking giant, throbbing cock, and begin gently stroking it with my hand, as we kept on kissing.
He started rubbing me all over my body, pulling me closely into him and we embraced. His arms wrapped around me, and both of his hands each grabbed an ass cheek through my panties. He inched his way down from my lips with his face, slowly kissing my neck and shoulders, and his mouth made its way to my nipples. He began sucking on one of them and I thought I was going to cum right then. It seriously had me panting like a bitch in heat.
“Oh my god,” I gasped, “Oh, fuck baby that feels amazing,” and with each comment I would make, he would go to the other nipple and start sucking it as well, all the while his hands were fully gripping my ass cheeks, pulling them apart, sticking fingers into my asshole through my panties. I couldn’t take it anymore, I felt like I was about to start shooting spurts of cum with each move he would make on me. My entire body had turned into a giant erogenous zone.
“I can’t believe I’m saying this, but I think I want to suck your cock, baby,” I said to him, in between deep and feverish breaths and amazing waves of internal pleasure.
With that, he pulled back, got up on his knees, held his cock by the base, and said, “Come get it.”
I turned to him, laid down on my belly facing him, and put my lips right on the tip of his cock. He moaned in delight, and I began playing with the head in my mouth. It would jump and spasm with each lick or kiss I would give it. I couldn’t fucking believe I was actually licking and sucking on a cock. Not just a cock, but a nice, fat cock that was attached to the nice body of a sweet, good looking guy. I had imagined it countless times, but the real thing was way better than anything my imagination was able to come up with.
I never really knew I would actually enjoy servicing a cock as much as I was enjoying this. As I was licking and kissing on Brad’s cock, I began to realize what the driving force behind my fantasizing about being a girl and being with a guy really was. Girls always gave me pleasure.
In my mind, every single thing about being a girl seemed amazing, from their looks, to their minds, to their smells, even to their societal roles. I envied all of those things, without even mentioning the obvious luxuries like clothes, lingerie, makeup, hair, and being pursued by men that want to love and fuck them. I’ve heard a lot of women complain about being objectified by men. I’ve never been able to fully understand that. Sexual objectification of me by men would be like a dream to me if I were a hot woman. But anyway, back to the story…
“That feels real good,” said Brad, “are you sure you’ve never done this before?”
I smiled, bobbed my head up and down on his cock to about the halfway mark and said, “I’m positive I’ve never done this before, but I’ve watched a lot of porn, and have secretly fantasized about doing it for a long time,” as I continued going up and down on his throbbing cock.
“I can’t say I’ve fantasized about sucking a cock,” he replied, “but I have fantasized about you sucking my cock for a long time.”
This intrigued me, and also really turned me on. I smiled and replied, “Oh, really? Me, in particular?” then I took him into my mouth as far as I could before gagging on it, which really woke up my saliva glands, and caused him to moan in delight. He began leaning over to get his hands on my crotch and ass. I suggested we lay opposite of one another on the couch, so he could be down by my ass, and I could remain laser focused on his cock, and so we did it.
He began rubbing my panties between my legs where my pussy should have been, and continued explaining himself to me. I began sucking his cock a lot more intensely as he began rubbing around on my crotch and ass cheeks.
“Yeah, while I’m not gay, and neither are you,” he said, as I was literally sucking his cock and he was toying with my asshole, “I have always thought you were cute for a guy, and I know how passionate and loving you can be from the songs you write. I always found that to be a turn on.”
The fact that he thought I was cute was extremely flattering to me, and the fact that he was into the love and passion I displayed through song lyrics made me eager to satisfy his every desire as best I could. I took my lips off of his cock, and gently put one of his balls in my mouth. They were huge! I had read in some porn mag about how to suck on balls, and the advice was to be very tender with them, as they are extremely sensitive.
I put one into my mouth, and he groaned in ecstasy, which in turn made me groan in ecstasy, which vibrated on his balls and made him twitch unnaturally. I suckled on it a little bit more, then let it out and took his other one in. At that point, I felt a brand new unbelievable sensation run through me. He had bunched my panties up onto my right hip, and licked my puckering hole. As he did, I felt a little dribble of cum spurt out of my now flaccid dick, which may as well have been a clit at this point.
It’s amazing how your body can react to your mind in sexual situations. I had gone soft as I began to suck Brad’s cock, but my entire pelvic region had begun tingling in pleasure the minute that I put his large cock head and shaft into my mouth, and my dick was very much participating in the pleasure that was taking place right below it in my sissy pussy.
He spit into my pussy a couple of times, slapped my ass cheeks sweetly, then held onto my hip with one hand, and stuck a finger from his other hand slowly into me. He didn’t get very far, maybe half of his finger went inside of me, and I felt another uncontrollable spurt of cum shoot out of me as he did. This made me extremely turned on, and I released his ball out of my mouth and grabbed his cock like it was a microphone and I was Mick Jagger.
“Oh yeah, baby,” he said, “suck that fucking cock baby, you’re an amazing cocksucker, baby.”
He was working his finger in and out of my pussy, stopping to re-lubricate it every so often with his spit, and I would writhe in pleasure and suck his cock even harder than I already was. I felt his hips thrusting into my face, then I felt another finger going inside of me. I had two fingers inside of me, and began grinding on them as he pushed them in and out of my quivering hole.
“Fuck my face, daddy,” I whispered, in between nonstop licks and sucks, “fuck my face, daddy.”
Apparently, he loved hearing me call him daddy. He began pumping his cock down my throat, and working his two fingers in and out of my pussy at a fevered pace.
“If I’m your daddy, then you’re my baby, understand?” he grunted to me, as I was willfully gagging on his engorged and delicious cock.
“Yes, daddy,” I replied, “I’m your baby girl, daddy, I want to eat your cum, daddy.”
With that, he began bucking his hips into my face, and his cock was going all the way down my throat, past where my tonsils would have been. I felt like was going to die from not being able to breathe, and frankly, I was feeling so much pleasure from head to toe that I don’t think I would have cared.
I could taste what I later learned was pre-cum, and it tasted amazing. I began spurting cum nonstop in my panties with every thrust he made into my mouth and into my pussy. The guilt that sometimes accompanies orgasms for me came and went in the blink of an eye. It wasn’t really about me, it was all about him, and I wanted to make him cum like a firehose. He had developed a rhythm between fucking my face with his cock, and fucking my pussy with his fingers, so that I had something penetrating one of my holes at all times, and it had me soaking wet.
“This is it, baby,” he panted to me, “I’m about to explode.”
I was slurping at his cock and replied, “I can’t wait to drink your cum, daddy, give it to me!”
With that, he gave his cock one hard stroke, said, “Open up, baby,” and aimed it right at my mouth.
He pulled his fingers out of my pussy, and his cock out of mouth, and turned around so that he was facing the same way as me. He pushed me down flat on the couch, and straddled my chest, pinning my arms back with his knees. I was practically out of breath, tears streaming down my cheeks from gagging so badly on his cock, and my lips were shivering in delight.
I opened my mouth, and the minute I did, he groaned and shot a huge rope of cum that hit my lips and went into my mouth, all over my eager tongue, like it had been shot from a gun. It was so forceful, that part of it overshot my mouth, and hit me in the nose and cheeks. It was so warm and delicious. I began wiping it off of my face and bringing it to my lips. He shot another smaller spurt that hit my chin, and at that point, I wasn’t willing to risk any of his cum going anywhere else other than into my mouth and down my throat.
I wriggled my arms free, grabbed both of his ass cheeks, and forced him forward so that his cock was back in my mouth. He began groaning in delight, and cum started flowing like a river into the back of my throat. I had tears streaming down my cheeks from inhaling his cock as deeply as I could. He started bucking his hips, fucking my mouth like it was a pussy, and shooting his baby batter nonstop.
I felt my soft yet very aroused cock leaking uncontrollably with each thrust he made into my mouth. It felt unlike any other orgasm I had ever experienced. Each secretion made my entire body tingle in pleasure. I loved having no power to make it stop. My panties were so drenched in sissy cum that it looked like I had been in a bath. He had so much cum!
His chest was heaving, he was sweating and breathing heavily, like he had just run a marathon. I was glowing in pleasure, I felt so naughty, so liberated, so satisfied. I was taking it down as much as I could, drinking him in, enjoying my feeding, when he began to slow his pumps. I did not want it to end, though, so as he began to pull his cock out of my mouth and back up, I sweetly pushed him backwards so that he would fall back on the couch.
As he went to lay on his back, I moved right along with him, keeping my lips fastened to his still stiff rod. We both may have been done cumming for the moment, but I wasn’t done enjoying his cock in my throat, and wasn’t going to stop unless I was forced to.
His cock became a little softer after cumming, but I wasn’t deterred. He chuckled a little bit and said, “Oh my god that was amazing,” as he was laying there trying to regain his composure. “It was the greatest orgasm I ever had.”
I mumbled a muffled response to him as I continued to suck on his cock.
“We should probably go,” he said, “but we should do this again over the break,” but I wasn’t finished.
I slowly pulled his dick out of my mouth long enough to say, “Why don’t you just relax for a minute, and let me keep worshipping your cock as you do, daddy?”
He went to say something else, when I reached up and put my finger over his lips, silently telling him to shut up and enjoy it. He took my finger, put it into his mouth, and started sucking on it. At that moment, I felt his delicious cock start to harden again, and knew my plan was working….