Have you ever had an experience with your best friend where gender lines are crossed? I have.
It was a night to remember, and the first of several future fun and exciting encounters that would continue.
I met Kyle on the first day of my freshman year at college. We hit it off right away. We laughed at the same stuff, liked the same music, we thought the same girls were hot, and we liked to get drunk and stoned routinely. We’re friends to this day, in fact. I lived with a couple of friends in a house about 5 miles off campus, and he lived with his sister, Lola, about a mile further down the same country road. We could get to each other’s houses in a matter of minutes.
Kyle and I had the same general experience in high school. He grew up in Memphis, and I grew up in a small MS beach town called Bay St. Louis, which was about 30 minutes outside of New Orleans. We both had lots of friends, dated lots of girls, and we both played multiple sports. I played football and baseball, and he played basketball and ran track. He was at university on a track scholarship, while I fell in love with music during the summer between my junior and senior years and quit all sports to play in a band. I still loved sports, and he loved music, so again, we got along great.
A difference between us physically was that when I quit sports, I got kind of finicky. I was 5’11” and weighed about 170. He was 5’9” and weighed about 190, but it was all lean muscle. He would take off his shirt at the pool and girls couldn’t stop staring at him. He knew he could get laid whenever he wanted to, and he was genuinely funny and personable to everyone he met. I was the funniest and most personable person you could ever know, provided that you got the chance to know me. I wasn’t as socially outgoing as he was.
He and I were inseparable for the four years we were there. One night during our sophomore year, we took a road trip to Kyle’s hometown of Memphis to go and see 2 bands, Superchunk and Sonic Youth. His parents were out of town, and we had their house to ourselves. Both bands were anchored by amazing female bass players, Laura Ballance and Kim Gordon. This was 1993. Laura was an adorably sexy nerd, and Kim Gordon was the shit. Coolest persona, great voice, just a badass woman.
We had a blast! Some of Kyle’s old buddies met up with us there, and we proceeded to get hammered, dancing, drinking, molly, etc. The show ended around 11, and we moved on to another bar for a few drinks, before heading home. Kyle was trying to pick up some girls to go back with us, but struck out. It was a Wednesday night. People had shit to do the next day.
We had a couple of tabs of molly left so we took them, had another drink at the bar, then headed to his parents house. Both of us were rolling and feeling amazing by this time. Kyle threw some music on in the living room when we got there, and told me I could stay in Lola’s room, so I immediately went to her room and closed the door.
She had the perfect stereotypical girls room, with a princess bed and her own bathroom. Instinctually, I went straight to her dresser and started looking through the drawers for her lingerie. She had a ton of different bras and panties in her top right drawer. Some were for everyday wear, and some were definitely sexy as hell. I love silk, satin, and nylon lingerie. It’s the most feminine, and feels amazing on my body. I grabbed a pair of red satin bikini panties and a matching bra, and went straight into her bathroom.
I cracked the door and yelled at him that I was going to take a quick shower, and he said he would be in the living room. I just wanted an excuse to change clothes. I hosed off quickly, put the panties and bra on, and put my clothes back on over them. I looked in Lola’s bathroom drawer and found some makeup. I put the slightest hint of pink sparkle lipstick on my lips, put it in my pants pocket, and headed back out.
He apparently had gone to his room to do the same, because when I came out, I heard water from his room, and music coming from the living room. He played a mixed CD, with a bunch of random 80’s new wave and punk stuff on it. I remember the first song was “How Soon Is Now?” I made us a couple of drinks and sat down on the couch. I put my head back, and closed my eyes, letting the music absorb into me. Molly is an amazing drug. I felt like I was in heaven, wearing girly lingerie as waves of pleasure rolled through my body.
Kyle came walking in and was wearing a thin silk robe. He looked hot, and I had never seen him in that way. I mean, I know he is hot, but I don’t really see a lot of guys as being hot, honestly. I’m infinitely more turned on and interested in girls. So much so, that if I had the nerve to tell the world that I thought I was trans, I’m pretty sure that I would lean more towards bisexuality instead of just guys, but secretly, I love the dick.
“I made you a drink,” I said, “have a seat, everything feels amazing right now. That’s a sexy robe, baby!”
He replied, “You like this robe, eh?” then started strutting towards me, as The Human League started playing from the speakers. He did a goofy dance as he walked towards the couch. We touched glasses in cheers, and he sat back on the couch right next to me. We both sat in silence, letting the music do the talking for a minute, then he started talking.
“It sucks that we couldn’t get any girls to come back here with us,” Kyle said, “I’m horny as shit, but I guess it is a Wednesday, ya know?”
“Yep,” I said, “we’re lucky enough to be able to skip classes tomorrow, but most people have to work or go to school. I must say, I’m actually enjoying myself right now.”
He replied, “Yeah, man, I know, and I am too. I just want to have my hands on a girl’s ass or the back of her head as she’s giving me a blow job, ya know? X always makes me feel so good, and it also makes me horny as hell.”
*A quick note: Kyle and I knew pretty much everything about each other, but the two secrets I had kept from him were that I loved dressing like a girl, and loved being treated like a girl by guys. At this point in my life, I had really only been with one guy, but I had been with him multiple times, in every way imaginable, and I was always a girl for him. I have written about our first time on here, go read it if you haven’t already. *
Hearing Kyle talk about just wanting to get his cock sucked got me really excited. I inched in closer to him on the couch, and began teasing him to get him laughing. He would frequently get loaded and start acting like he was gay for laughs. He would walk funny, talk with a lisp, and wiggle his hips while saying stupid stuff, and calling me or any other guys around him names like Honey or Baby. It was harmless stuff, but sometimes it would get me horny when he would start doing it, because he would get touchy feely and really commit to it.
I started playing his game. I leaned into him and said, “Is your cock raging right now, stud?”
He chuckled, then brought his hand down to his crotch and said, “What do you think, baby?”
He tightened his robe around his crotch to show me the outline of his cock through the fabric, and he was raging hard. It was quite impressive, but he thought I was just playing around with him like we always did. He had no idea that my mouth was watering and my pulse had intensified.
I said, “Look at you, daddy! You’re all plumped up! Looks like you need release!”
While talking, I “accidentally” ran my hand along his thigh, and it immediately gave him goosebumps along his legs. He also took a deep breath and made a groaning sound, which turned us both on. He smiled and chuckled, then said,
“Don’t you wish it was that easy? Like, we want our dicks sucked right now, and somebody should be on call for that kind of shit, ya know?”
“There are people on call for that,” I said, “They’re called call girls.”
He laughed, then said, “Molly always gets me horny as shit, I just want a little harmless fun.”
The next song came on. It was Madonna, Like A Virgin, and Kyle got suggestive about what to do.
“Hey, wanna have some fun?” he said, “get up and dance for me, baby!”
I blushed and said no, but he was in a really playful mood, and continued:
“Seriously, it’s just us, you dance to this song for me, and I’ll get up and dance for you on the next one.”
We laughed and I agreed to dance for him. I had him back the song up to the beginning so I could go out to the hall and make an entrance.
I noticed his jaw grinding, and so was mine. We were both full of chemical euphoria from the molly we had taken, and it was hitting its peak at exactly the right time. It is an indescribable feeling of comfort, and all inhibitions come undone. We had never acted like this or gone this far into left field. As mentioned earlier, we had played around while drunk and pretended to be gay, but it was always in front of others for laughs, and it stopped right there. This wasn’t stopping, it was intensifying, and we were both fully engaged on the ride we were taking.
As the song started, I sashayed into the living room, swaying my hips, and blowing kisses. I lip synched along with Madonna. I started moving towards him, jiggling my chest, and strutting like a whore. He was loving it, laughing his ass off, and making cat calls at me as I lost myself in the moment. In my mind, I was a girl, and he was looking at me like I was Madonna herself.
“Turn around and shake that ass, baby!” said Kyle, sitting up at full attention on the couch, “Let’s see you make it wiggle!”
I replied, “You would like that, wouldn’t you, daddy?!” and began dancing closer to him, shaking my ass as best I could.
He paused the song, and said, “Hold up! Hold up! I’ll be right back!” and he sprinted out of the room, as I was standing there, horny as fuck. I pulled the lipstick out of my pocket and applied it heavily. Kyle came back into the room waving a fistful of dollar bills and had a shit eating grin on his face. His eyes widened when he saw my frosty pink lips.
“I love your sparkly pink lips, baby!” said Kyle, as he sat back down on the couch attentively, and started the song over again.
I acted annoyed that he was starting the song over again (I wasn’t) and pranced off to the hallway again to make an entrance. As the song began, I started my strut. I walked as sexily as I could directly towards him, swaying my ass. He stood up on the couch, and started waving a dollar bill at me. His robe was barely tied around the waist, and as he pretended to gyrate, I could see his cock flopping wildly through the silky fabric of the robe.
I blew him a kiss and walked right up to him. He folded the dollar bill up and put it between my lips, which made us both laugh. He quickly sat back down and had a request:
“Turn around, slut! Let me see that ass! Grind on me, sexy bitch!”
I gave him my best attempt at sexy, sissy eyes, turned around, and began walking backwards towards him, swaying my ass from side to side.
“That’s it,” he said, “bring that ass down on daddy’s lap!”
In that moment, I just let go of any remaining inhibition I had, and lowered my ass right down on his crotch and began grinding. I could feel his hard cock right between my cheeks, and I massaged it in a circular motion, while bobbing my ass up, down, and all around him. He put his arms around me and out in front of me, and began showing the dollar bills I had just “earned.”
He said, “That’s right, baby, you deserve this cash! Back that ass up, I’m gonna put it in your underwear!”
I was lost in the moment, trying to act like I was laughing with him, but in reality, I was totally turned on and had excitement butterflies swirling throughout my body, so much so, that I completely forgot that I was wearing his sister’s bra and panties as I ‘backed that ass’ up to meet him at eye level. As I was swaying my ass back and forth in front of his face, he began pulling my pants down, then obviously saw my ass draped in shiny red satin and stopped to comment.
“Whoa!” he said, “what are you wearing?”
I got nervous but tried to remain calm, cool, and keep the conversation light and fun, as I continued to lightly sway my ass back and forth in his face.
“Oh my God,” I replied, “I totally forgot that when you suggested we dance for each other, I ran back into Lola’s room and threw some of her lingerie on to surprise you. If this bothers you, I can take it off, and I know I had no right to go into her panty drawer, I was just caught up in the moment as that molly was kicking in.”
He didn’t say anything in response, but his hand remained on my pants. I felt it go under my pants and begin moving around, feeling my ass cheeks that were being cradled by these sexy satin panties. I heard him begin breathing heavily as he did so, then he started quietly laughing lightheartedly and he broke his silence.
“Man, I know this will sound weird,” he said, as his hand was now pushing my ass cheeks apart and his fingers were running up and down my ass crack, “and I never ever acted on these feelings, but I always thought my sister was hot as fuck. Maybe it’s the molly talking.”
I started moving my ass gingerly while his hand kept exploring, and his breathing got a little more intense.
I tried to comfort him. “I know that it does sound weird when you talk about your sister like that, and I know you would never act on anything like that, but I have to agree with you. Your sister is totally fucking hot. She’s so girly girl, and you’re so manly man, but you’re both fortunate in the looks category.”
He was smiling, clearly not of his right mind, and apparently was extremely turned on. He pulled my pants down a little further, and gripped my ass cheeks with both hands now, as his breathing intensified even more, then he started chuckling again.
“You know what?” said Kyle playfully, “I’ve determined that you’ve been a naughty girl, and deserve to be punished for it. I think I have a solution if you’re willing to accept my punishment.”
Now I began breathing heavily, as one his hands made it inside of the panties. I remained turned away from him, as he spread my cheeks with his 4 outside fingers, as his middle finger began running up and down my crack, flirting directly with my boy pussy hole. I made a quiet, satisfactory grunt as he did so.
He asked again, “Well, are you willing to accept my punishment?”
I played along with him, not sure where any of this was going to end up going.
“I have been a naughty girl,” I replied, “and I think I do need to be punished for putting on your sister’s panties and bra.”
He replied, “Wait a minute, you’re also wearing one of her bras?”
I nodded yes to him, and grinded my ass back into his hands as best I could from the position I was in.
“Very well, then, little lady,” said Kyle, “here’s what you’re going to have to do. I need you to remain facing away from me, and to stand up and take off your shirt and pants, and strip down to your girly bra and panties. Understand?”
My heart started pounding in a good way, as I nodded in approval, and stood up to remove my boy clothes. I took of my bulky shirt, then let my pants fall to the floor. There are few things that make someone feel as vulnerable as standing in flimsy, shiny girly underwear with their back turned on a man, as you can hear him intensely breathing.
Panties and bra leave every other inch of your body exposed. Girls that wear them like bathing suits and manage to look hot have amazing bodies. I wasn’t fat, but could feel whatever little tummy I had hanging ever so slightly over the waistband of the panties. I had no titties like a woman, but luckily Lola’s bra was somewhat padded. He continued with his directions:
“Good girl, very nice,” he said, “now, I need you to close your eyes, get down on your knees, and turn towards my voice.”
I did as I was told, and got down on my knees, then turned towards Kyle with my eyes closed, and inched towards him, breathing heavily. I could hear him breathing heavier, and could feel him grinning from ear to ear as I inched closer to him. George Michaels, “I Want Your Sex Parts I & II” started playing from the speakers, as if there were a DJ hiding behind a wall, like the goddamn Wizard of Oz. I could barely hear movement on the couch over the music that was pumping, but heard it nonetheless.
In a low and seemingly much more serious tone, Kyle said, “By the time I count to 10, I need you to have your arms by your side, and your mouth open. Understand, baby?
I smiled and tried to act like I was somewhat hesitant to follow his commands by saying, “You better be good to me, daddy. I am not into this, and am role playing with you for fun, so…”
He laughed and replied, “Of course, silly bitch! This is all in good fun, just me and you, and I’m not into it, either. Have I ever done you wrong, baby? You’re being a good girl, and I would never do you wrong.”
He sweetly patted me on the top of my head twice and told me to relax. He promised we would have fun and I would love it. He then began counting. He would pat my head as he counted, one pat for one, two pats for two, and so on. When he reached 10, I opened my mouth, and dropped my arms to my side as he said to do.
“Now open your eyes, baby,” he said to me, in the sexiest lowest tone I had ever heard come from a man in my life. I did as I was told.
As soon as my eyes opened, he was smiling and holding his rock hard cock right in my face, and softly thumped me again across my nose and lips with it. I was salivating, and rifled his cock into my throat as far as I could. He groaned loudly and moaned sexily, with his entire cock all the way down my throat. I began breathing through my nose, and had my hands wrapped around his torso, gripping his sculpted and meaty ass cheeks, gently pushing him into my face in an effort to literally swallow his entire cock.
“Is this gay?” said Kyle, as he began thrusting his hips and burying his cock down my throat.
I tried to reply but he grabbed the back of my head and began pumping even harder into my shiny pink lips. I shook my head to indicate “no” as he was literally fucking my face.
“No, it isn’t gay?” he said, as he continued to gyrate. I nodded my head to indicate “yes” as he forced me all the way down on his cock as far as he could and held it there. My nose was buried in his pubes.
“Yes it’s gay, or no it isn’t gay, slut?” he asked, as we made eye contact. He gave me sweet smile, and caressed my cheeks, pushing them inward so that he could feel his cock in my mouth through my skin. I couldn’t take not being able to answer him, so I pulled myself back and let his sloppy wet cock slide all the way out of my mouth.
“It’s not gay,” I said, then resumed sucking his delicious rod, and he resumed thrusting into my face.
“How do you figure that?” he asked, then pulled his cock back out of my mouth, and thumped me in the face with it several times awaiting my answer. Each pop he gave to my lips and nose was making me moan, and I finally replied to him,
“It’s not gay, because I am wearing slutty girly lingerie and have painted my lips sparkly pink like pussy lips. How can it be gay if I’m a girl?”
With that, he leaned down and gave me a deep tongue kiss, and rubbed on my tits through the satin bra, then stood back up over me, and plopped his cock back into my mouth and resumed fucking it. He started talking really dirty to me, degrading me, but every time I looked up at him, he was smiling, like he wanted me to know that he was just playing. Here’s a sample of our exchanges:
Him: “What’s your name, little bitch?”
Me: “Call me Katie, daddy.” (slurp, slurp, slurp)
Him: “Keep slurping on that cock, Katie slut”
Me: “Yes, daddy.” (slurp, slurp, slurp)
Him: “Swirl that slutty cocksucking tongue around the head of my cock.”
Him: “If I’m not mistaken, I think you like being a girl for me, don’t you?”
Me: (throats entire cock until my nose is in his pubes and holds for 10-15 seconds)
Him: (groaning) “I said I think you like being my sissy girl, don’t you?”
Me: (finally releasing and coming up for air) “Yes, daddy!” (resumes)
With that, he overpowered me, pushed me onto my back, and after making out furiously with me for about a minute, he put his knees over my shoulders, leaned forward in a push up position, forced his cock back down my throat, and began pumping furiously into my mouth. I felt my own cock leaking into my panties, and he was grunting with every thrust for another minute or so, until he started cumming.
His cum was very warm, and he shot copious amounts of it into my mouth. It was like I was being water boarded with jizz. I drank every bit of it that I could get down my throat, but there was still plenty to clean up. He had stopped thrusting, but kept his cock down my throat, as he was trying to catch his breath. Sweat from his tight belly was dripping onto my face. He pulled his cock out and came backwards to lay on top of me. He started kissing me and running his tongue all over the inside of my mouth, as if he were trying to get as much of his own cum as he could to swallow as well.
We laid there making out for several minutes, his eyes were closed the whole time. When he was finished, he dismounted my shaking body, and lay beside me, draping his arm over my body, and caressing it, rubbing it up and down between my tits and my crotch. He noticed that the front patch of my panties was also wet with cum, and he played with my cock and balls through the panties, rubbing them as if they were a clit. It felt amazing, and got me turned on all over again.We were both breathing heavy, not saying anything, just taking in the feelings that were happening.
“Oh my fucking God, that was awesome!” he said, “We have to get some more molly and come back up here for another concert when my parents are gone!”
“That sounds delightful,” I said, “it can be our little secret, and please don’t mention it to anyone.”
He said, “Are you fucking kidding me? I would never mention this to anyone, partly because I know we would both be outed and lose all of our friends, and partly because I want to keep you to myself. You just gave me the best blowjob I’ve ever had. You’re an amazing cocksucker, Katie!”
We sat up for another hour or so, barely talking, just soaking in what had just occurred and listening to music. Kyle suggested that we go to bed in order to get back to school at a decent hour, and I agreed. I went to Lola’s room, and he went to his room. I got in bed, and immediately began playing with my cock with one hand, and fingering myself through the panties with the other. About 10 minutes went by, when I heard him knock on the door.
“Who is it?” I said, playfully. The door opened and there he was, completely naked. He walked towards me, pulled the sheets back, and got in bed with me. He cradled me like I was a girl, then spooned me, with his hard cock planted right between my ass cheeks on the outside of my panties, kissing me on my shoulders, and gently dry humping me until we both fell asleep.