tagTransgender & CrossdressersMy Brother's Panties

My Brother's Panties


This one crosses a number of categories from incest, gay, fetish, group, toys/masturbation and transsexual. I went with transsexual as it is the predominate theme. As always, constructive feedback is welcome.


My brother and I are twins, fraternal not identical. Throughout our lives, no one ever confused us, and furthermore, no one ever thought we were siblings. Growing up I would often get the question, "Kevin, why do you hang out with Jamie so much?" People were always surprised when they learned we were brothers.

I was the strong one and Jamie was the weak one. I won't go into sports, dating, friends and all the things which make or scar kids on their way to becoming adults. Rather, I want to concentrate on what life dealt Jamie and how he played it.

Without a doubt, Jamie is the nicest, kindest, sweetest person I ever met. He cries at movies, takes in stray cats, has incredible taste in home furnishings, and a fashion sense envied by women. He always had these traits, and because of them, Jamie was bullied and the target of slurs.

When we were kids, he was called 'faggot.' I felt so bad. How could people be so cruel to such a nice person? On more than one occasion, I came home with a bloody nose, a black eye, or a swollen hand because I stood up for Jamie.

All I ever said to our parents was "You should see the other guy." They never condoned fighting, but they knew what was going on and chose to say nothing. Jamie would always come into my room later at night to say thanks. He used to call me his 'shining prince' while giving me a tender hug or gently running his small soft hands over my injury.

My parents didn't know what to do for Jamie. They loved us both, but had strange ways of showing it. Mom would always ask Jamie for his opinion on fashion and they often went shopping together. Dad ignored Jamie. Seriously, Jamie could have set himself on fire while standing on the dining room table and Dad wouldn't give him a glance. However, he would always ask me how Jamie was doing. When I told him he was doing OK, he would nod and walk away.

By the time we turned eighteen and graduated from high school, Jamie was transitioning well from Jamie Drexel the effeminate man to Jamie Drexel--the woman.

Jamie no longer wore men's underwear or t-shirts. In their place, he donned various colors and cuts of 'boy style' panties with matching sheer, lace trimmed, tank tops. I think Mom bought them for him on their shopping trips or she at least accepted it because they were all cleaned and in our laundry baskets. I must admit, I did have an aroused curiosity, and would always check out his things when no one was around.

One of the conditions of his acceptance into a New York City fashion school was the completion of a starting portfolio. This meant he didn't have to get a summer job. From June to August, while our parents were at work, Jamie would move around the house wearing nothing but his intimates. He said he felt more comfortable and less inhibited while he worked.

Since I was going to study business at a school less than an hour away, I had to get a summer job. Luckily, I was hired back as a lifeguard at our community pool. My hours varied as the guards worked rotating shifts, so I got to see Jamie a lot that summer.

That summer produced a definite change in my brother. He would give me looks when I was in my speedo or stare at me through the mirror while I showered and dried off. We always shared a bathroom so Jamie being in there with me was not unusual.

However, Jamie was now overtly looking at my cock while touching his, or licking his lips. When I would catch him, he would just bite his bottom lip and give me a seductive look. Often his cock was hard and pressing against his panties. I had to admit there was something that turned me on about Jamie.

There was another big change going on with Jamie—breasts. They started with puffy nipples, and plumping areolas. This time it was Jamie catching me staring. I wouldn't do the lip thing, but our eyes always shared a lustful glance.

Jamie was never very hairy, but his skin was becoming silky smooth. When he left for New York in late August, Jamie's blonde hair was long, luxurious and flowing. I'll never forget the way he looked the day we dropped him off at O'Hare.

He wore a white starched shirt; the top three buttons of which were open. The tails of the shirt were tied in a knot just above his now pierced navel. Tight blue jeans rode his slender hips. They were women's---Halo's, with the little indentation in the back. They shaped his ass into a perfect heart. No belt was necessary.

A stylish pair of sandals completed his outfit. With his blonde locks in a ponytail, he looked kind of hot. A Midwestern girl heading to the Big Apple.

When we got to airport departure area, Dad said he'd wait with the car and meet us in short-term parking. I saw him give Jamie a look and wished him luck. He also said that Mom would be in contact if he needed anything. That was the closest they ever got.

Mom and I walked Jamie into the terminal. I carried the luggage, while Mom and Jamie talked. She was in tears. Her baby was leaving. It was pretty embarrassing. I told her I would finish up with Jamie and for her to head back to the car.

They exchanged hugs and Mom took an envelope from her purse and told Jamie it was "a little something from your father and me." The envelope had six-thousand dollars in it. For the record, I got shit when I headed off a few weeks later.

We finally got everything checked in and Jamie had his boarding pass. We were standing in the main concourse with people moving all around us. Jamie took both of my hands in his. There was a sensual softness in his touch. Looking up into my eyes, Jamie spoke. "Kevin, I am going to miss you more than you will know. You have been my 'shining prince' my entire life and now we part. You probably know I won't be coming back anytime soon....if ever. My new life starts now."

Somewhere deep inside me, I did know that. Still, I felt sad.

He continued, "If you ever get to New York, please visit me. My door will always be open to you."

Jamie brought a hand to each side of my face and pulled my head towards his. I was stunned when his lips found mine and gave me a tender, yet passionate kiss. His lips moved over mine.

Breaking it, he said, "I Love You. Always have. Always will."

He turned and headed towards the gate.

I stood there in stunned silence watching Jamie's ass sway as he made his way to his gate. What stunned me the most however, was my state of arousal. If his kiss lasted any longer, I would have been standing in the middle of O'Hare with a raging hard on.

Things changed for me that day also.

When we got back to the house, I snuck into Jamie's room to see what girlie things he left behind. I found all sorts of things, panties, dildos, a few training bras, magazines featuring transgendered women and Jamie's notebook of sketches.

He had drawn pictures of men sucking T-girl cock and vice-versa. There were ass-fucking sketches and every cum shot was going into someone's mouth.

I was in shock. I was aroused, I was torn. I was a guys' guy. A ladies' man. I could have any girl I wanted. But looking at these pictures turned me on...a lot!

My cock was throbbing as I turned each page. On one page, Jamie had even label the guy as Kevin and the T-girl as Jamie. He also had journal entries saying how he wanted to suck my cock and how he thought I want him too. He described it as "the look in Kev's eyes."

I took the book back to my room and hid it under some sports magazines in my nightstand.

That night when Mom and Dad were asleep, I brought it out and looked at it again. I treated my cock to a slow soft jerk with the turn of each page, envisioning what it would be like to actually do those things. The thought of Jamie's panties and the dildo in the next room was a sexual lure.

A quick check of the hall and I was back in Jamie's room. I grabbed a couple pair of panties and the dildo. Touching the dildo nearly made me cum it on the spot. It was soft, yet firm and felt very realistic.

Back in my room, I crawled back into bed with Jamie's things. Laying on my back, I took a pair of his panties and began stroking myself. Reaching for the dildo, I didn't hesitate bringing it to my mouth.

My lips sucked in the head as my tongue coated the crown with saliva. Feeling the hole, I snaked my tongue into it. This was heaven. Sucking cock seemed to be the most natural thing in the world for me.

Envisioning Jamie straddling my shoulders with his knees on either side of my head, I started fucking my mouth with the dildo pretending it was Jamie's cock. It didn't take long to explode. Cum soaked Jamie's panties and spurted onto my stomach.

Removing the dildo from I mouth, I used the head of it to scoop up some of the cum. Returning it to my mouth, I completely cleaned my seed from it. The salty taste was heady and being so taboo, made me want it even more. Over and over I cleaned my cum from the cock, after which I brought Jamie's soaked panties to my mouth and sucked the cum from them.

It took a while to settle down, and for reality to set back in.

"My God," I thought. "What have I just done? I'm not a faggot. I like girls. What the fuck?"

With two weeks left before college. I hit the party circuit and fucked and sucked every chick willing to give it up. The whole time my mantra was "I am not a faggot." I was out to prove my manliness.

But each time I was alone, my actions told me the truth. If I am not a faggot, then why does sucking this dildo turn me on so much? Why do I love to lick cum from it or to have it glide in and out of my ass? And why does wearing and cumming in Jamie's panties turn me on so much?

I left for college still confused. However, I did take Jamie's panties, the dildo, and the sketchbook with me. I knew this was more than a passing phase in my life.

My first day in college brought my first surprise. His name was Greg and he was my roommate. One could tell he was an athlete or former athlete. He was about five foot ten and lean. He wore a black T-shirt, which hugged his well-developed frame. It matched his dark black hair.

His baby-blues were captivating. Surveying the rest of his torso it was impossible not to notice the bulge he was packing in his form fitting jeans. As it turned out he was on the diving team in high school.

Greg moved in while I was at the bookstore. I was a bit startled when I first entered the room, since no one was there two hours earlier. He apologized for scaring me, and based on the tone of his voice and the enunciation of his words, I knew he was gay.

Within the first ten minutes, Greg confirmed this by telling me he was gay. Greg was talking and I was listening. When he asked me if I had a problem with a gay roommate. I smiled and told him there was something I needed to show him. I went to my closet and retrieved Jamie's sketchbook.

I moved from my side of the room and sat beside him on his bed. This move alone created a sexual tension both of us sensed. I gave Greg a quick but spicy summary of Jamie and told him about the kiss at O'Hare and finding Jamie's sketchbook. Opening to the first page set the tone.

Greg gave a little sigh when he saw the sketch. He moved closer to me, placing one arm behind my back and resting his weight on it. His forearm leaned against my back. He placed his other hand on his thigh, the one next to mine.

When I turned the page, he moved his hand onto the page in an attempt to highlight some obscure detail. "I love how Jamie makes their cocks slightly bigger and out of proportion to the rest of their bodies."

At this point, Greg's face was very near mine and he turned his head toward me. I felt his breath against my cheek. The time was at hand.

I turned my face towards him and looked into his eyes. They were filled with lust and desire. We hesitated for a lingering moment and then our lips met.

Greg's mouth opened and instinctively I pushed my tongue into it. He sucked it in but in a manner unlike a woman. There was a power to his kiss. We fell into an embrace on his bed and kissed long and hard. It was different, arousing none-the-less, but different. Instead of the soft smooth skin of a woman, I could feel the freshly shaved stubble of a man.

It was exciting to feel his cock through his pants. Both of us were groping one another. Although this was a first for me, there was no hesitation on my part. This was something I wanted. Greg seemed to want to take control.

Pushing me onto my back, Greg unbuttoned my shirt while still kissing me. The contrast between a man and a woman were striking. Greg's movements were direct.

When my shirt was completely open, he slid his mouth to my nipple and began sucking it. His hand moved to my pants and started to unfasten them. Pushing them down my legs, he returned his hand to my underwear and did the same to them. My cock was free, erect, and very hard. Greg grasped my shaft and pushed it against my body, massaging it into the flat of my abdomen. The feeling was very primal. I was aroused and wanton.

Slipping between my legs, Greg took my rod into his mouth and began sucking it and I mean sucking. It wasn't sensuous or erotic. This wasn't a beautiful woman looking into your eyes as she fellated and worships your penis. Still Greg's hunger for cock was evident and his mouth was doing the job.

The more he sucked the hotter I became. I told Greg it was my turn and he wasted no time in standing up and removing his clothes. While he disrobed, I kicked off my pants and undies, and threw my shirt across the room onto my bed. I was still sitting on the bed when Greg stepped in front of me and presented his cock to my mouth.

I thought of how I sucked Jamie's dildo and gave his cock a big lick. Greg had other thoughts and at his first opportunity he shoved his rod into my mouth and began fucking it. As basic and manly as it was, there was something sexually arousing about it. I took each thrust. Pre-cum started to seep into my throat; it was a taste I recently learned to crave.

My cock was still rock hard and I couldn't stop myself from stroking it as Greg fucked my mouth. I was getting close to cumming and so was he. Greg started to grunt and said he was ready to explode. He pulled his cock out, and aimed it at my face while furiously stroking his shaft.

Opening my mouth, I gave him a target and Greg's first blast landed directly in it. Although I tasted my own cum numerous times before, the lewdness of another's seed sent me over the edge. Cupping my hand over the head of my cock, I captured my cum and rubbed it over the head of my cock intensifying my orgasm.

Greg's cock was feeding me shot after shot. I collected all of it. When he was empty I tried to pull his cock back into my mouth for a couple of final sucks. He wasn't game for it and stepped back saying, "Pretty good blow job, Kevin. This is going to be a fun year."

I can't say I was as pleased as Greg. Yes, I came and there is no such thing as a bad orgasm. However, it was just sex. There was no sense of emotion, or sensuality to it. That night we fucked each other up the ass. It reminded me of two dogs letting their hormones control their genitals while their brains were elsewhere. Greg was happy and I was registering firsts.

On campus, I was noticing both the guys and the girls. Even though I now officially had cock, I still had an overwhelming attraction to women. Seeing a sexy woman still aroused me, while the guys were just cocks.

Sex with Greg was every night and it was getting very mundane. As luck would have it, Greg dropped out of school after the third week. He said it wasn't for him. When he was all packed up and his parent's car was loaded, he came back up to the room for a good-bye blow job and I gave it him. I was actually glad he left.

That night I took out Jamie's dildo and panties for some long overdue self-pleasure. It was so much more fulfilling.

Wearing Jamie's panties, I started dancing to the tunes playing in the background. Watching myself in the closet mirror, I found the sight of the tight panties silhouetting my cock to be intensely erotic. My dancing became more suggestive. They image in the mirror was really turning me on.

The more I danced, the harder I became. My hands never touched my cock either. They somehow knew it was more seductive to trace its outline through the panties in synch with the music. They caressed my ass and nipples suggestively, stopping short of direct stimulation. It was the pure sense of lust that was making me rock hard.

Picking up Jamie's dildo, I moved closer to the mirror and began to caress and lick it. I slid it down my chest, across my nipples, and began to rub it on the outside of the panties against my straining cock. I was watching myself the whole time; the image looking back at me a slutty whore.

Dropping to my knees, I pushed the dildo length-wise against the mirror and began to bathe it with my tongue. It looked like two people double-teaming a cock as my mouth went over the fleshy shaft. Pre-cum oozed from the head of MY yet un-stroked rod.

Sucking the phallus into my mouth, I worked it with an immoral hunger. My eyes were glued to the raw sensuality being presented in the mirror. As one hand worked Jamie's dildo in and out of my mouth, the other dipped into my panties to free my cock. It was time.

My hips gyrated as I stroked. The look of my long hard cock with the panties pulled underneath my balls was electrifying. This was the sense of lust I sought. I wanted more. I coated the dildo with my saliva and pulled the panties from around my ass.

Placing the phallus at my ass hole, I eased it into my chute. After three weeks of Greg taking me, I had develop the ability to easily relax and open my bud. This felt so good. Pushing most of it in, I sat back on my calves trapping the end of the dildo between them.

I started rocking my hips back and forth on top of my legs. The dildo slid in and out on each rock. I was climbing to another level. The only thing that mattered at that moment was pleasure. My ass began attacking the cock. It couldn't go deep enough. My hips pulled up and then slammed down, burying its length up my chute.

After each downward thrust, I ground my hips on the cock. I could feel it move inside me. Seeing me fuck myself was mind blowing. I looked hot. I wanted this. The person in the mirror was out of control with need.

My hands pulled on my cock as my ass went wild. There was no rhythm between them. My cock was being serviced; my ass was being serviced; and my mind was being shattered.

The orgasm destroyed me. Cum exploded from my cock and splattered against the mirror. It filled my hands and dripped between my fingers. Stream after hot goody stream shot from my cock head. Never before had I cum this hard. I began to shake and went blank.

When I regained my composure, I realized I must have licked the cum from the mirror. My face was smeared with it, as was Jamie's dildo. Did I pull it from my ass, coat it cum and then suck it off? The evidence in the mirror said yes. That orgasm sent me to a new world; a world of desire; a world from which I never wanted to leave.

No one moved into my room after Greg moved out, so I didn't need to be clandestine. I started to wear Jamie's panties full time in the room, even though they were a bit small for me. They gave me a feel of sexuality. They also conjured up images of Jamie moving around the house and teasing me with his panty clad ass all summer.

I had many mind blowing solo sessions that year. Still, there was something missing. I needed feminine softness. Girls started coming back into my life. How I enjoyed their lips, and sexy ways. I was pretty successful in smooth talking them back to my room for some rousing sex.

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byseat542© 20 comments/ 149997 views/ 211 favorites

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