If you could take a pill that would permanently change you to the opposite sex, would you take it?

Few people would state an immediate yes to jump on the chance to take a pill that would change their gender forever. Most of which either knew at a very young age or even just recently realized that their genetic makeup did not suit who they are on the inside.

If you could take a pill that would permanently change you to the opposite sex, would you take it?

Then there is the majority of the population.  Either never once considered being the opposite gender or have no desire to change.  Usually one will get the quick “No” or a funny look followed by an “Oh hell no” type reaction.  Others may give you more of a repulsed look at the question.  

If you could take a pill that would permanently change you to the opposite sex, would you take it?

Then there is the population that would say “Hmmm, guess I’ve never really given it thought.”  The question intrigues them enough to start doing hypotheticals but ultimately will give a no response.  While for some it will be the one pivotal moment that starts the formation of their egg, and it is just a matter of time before it breaks.

If I could take a pill that would permanently change me to the opposite sex, would I take it?

This was the question that was posed to me not so long ago.  Let’s just say, I fell into the “never thought about it” population.  That was the question that formed an egg and started me down an unexpected path.  That was also the question that ultimately broke my egg.  But I am getting a little ahead of myself.

I remember that fateful day when I (Jessie) was asked that question.  It was well into adulthood when my best friends and I were talking about recent events in the news.  One of the events eventually steered us toward a friend that recently came out as transgender.  It was roughly 50/50 on those that were supporting versus not.  This set up a debate among our group about how many people really would consider a change if it meant they wouldn’t lose a thing by changing their gender.

Most of my friends ranged from a quick “No”, to a “Hell no”, and “Even if you paid me millions of dollars, I wouldn’t do it.”  Some of these friends even started poking fun of why anyone would even consider the change.  When the question came to me, I fumbled to come up with an answer.  I guess I never really gave it a thought.  

I finally blurted out, “I guess I have never really thought about it.”  I quickly steered the conversation away from having to answer.

Eventually, everyone but Scott and I left the bar.  I was inebriated enough to be in no condition to drive.  Scott was kind enough to drive me back home.  At a stoplight, Scott turned to me and said, “You know, you never really answered that question.  If you could take a pill to permanently swap genders, would you?”

Even in my inebriated state, I knew I had to tread carefully in my response.  “Well. Like I said, I never really have thought about it.”

Scott’s eyes narrowed in on me.  He knew I was continuing to evade the question.  “Come on, man.  I know those gears in your head are cranking.  I won’t tell a soul.”

“Ummm.  Well.”

“Well, what?  Stop stalling or else all our friends will hear what I think you would say.”

“Scott, seriously.”  Thinking of the next words to say.  I knew what I wanted to say, but what came out seriously was not what I was thinking. “It kind of intrigues me.  Especially since I love to wear women’s…”

I knew it.  I messed up.

With a huge questioning look on Scott’s face, he replied “What did you say?  Finish it.”

I tried to change the conversation, but Scott wouldn’t let it go.

“Okay.  This is between you and me.   Deal?”

“Of course,” Scott replied.  “Unless it is really juicy of course.”

“When I was younger, I discovered my love of women’s panties, hosiery, skirts, and high heels.”

“Shit!  No way!  And???”

“Well, when I dress up, sometimes I wish I was born a woman.”

“And?”

“What do you mean and?” I retorted.

“Aw come on, there has to be more.  No guy just dresses up for no reason.  Spill it.”

The infamous “Resistance is Futile” moment.  “Okay, promise you won’t tell a soul?”

Scott smirked, “Of course, man, or should I call you woman?”  This caused me to laugh a little.

“Seriously, Scott.  I don’t want our friends to know.  This is just you and me.”

“Okay. Okay.  I Promise.”

“When I dress up, my alter ego comes out.  I pretend I am her in every way possible.  When she wants to go home, I get sad so to speak.”

I am certain by this point that Scott knew the real answer, “Okay, Okay.  So would you take the pill?”

“As I have said, I never really gave it any thought.”

“I think you have and don’t want to admit your answer would be a yes.”

I retorted, “Seriously, I have never thought about it.”

“Yeah.  Okay, don’t believe you”

We finally got to my place.  I was getting ready to exit the car when Scott stopped me.  “Mind if I quick use your bathroom?”

“Absolutely not,” I replied.

Once we got in the apartment, Scott quickly turned to me.  “I am really intrigued.  I want to see you in woman mode.”

“WHAT!?!?”  I was shocked.

“Seriously, I have been trying to visualize what.  What is her name?”

“Jessie.”  Dang, blew another one, he knows my identity.

“I want to see Jessie in the flesh.”

It took me several seconds to think it through.  Part of me was super thrilled for Jessie to come out in the flesh, yet another part was terrified.  It was obvious I was indecisive and needed a nudge.  Since Scott and I have been friends for such a long time, he knew what button to press to push me over the edge.

“Come on, Jessie.  I know you want to meet Scott.”

“Shove it, Scott!”

“Jessie, you know you are dying to come out.  I can see it in your face.”

"Seriously, Scott, knock it off!”

"Jessie, if you meet Scott, I promise you concert tickets to your favorite band…”

“Not this time, Scott.”

“You're playing hard to get, Jessie.  How about a date with my sister.”

“Your sister? How.”  I thought he was bluffing.

“See this?”  Scott takes out his phone and shows me a conversation between him and his sister.  It was obvious she was interested, but it was the bro code.  No dating friend’s sisters.  

“You’re willing to make an exception to the code?”

Scott types some stuff on his phone.  My phone dings.  I read the message that he agrees to break the bro code.

“Okay.  Just this once.  And not a soul will know,”  I reply.

“Absolutely.”

I staggered into my room.  Not sure why, but I was seriously getting horny by the situation.  It took me about five minutes to settle on my Little Red Riding Hood costume.  Not sure why I chose that as it is very provocative.

“Come on, Jessie!  What is taking so long?”

“Mind your business, Scott. This is a huge step to show off my alter ego to someone else.”

I put on a matching red lingerie set with a bra, panties, garter belt, and sheer white thigh-high stockings.  I then placed my C cup forms into the bra, followed by my favorite five-inch red heels.  Next, I wore the Riding Hood costume, and finished it off with a red wig, some lipstick, and eyeshadow.  Not sure why, but I wanted to look absolutely stunning to him.

“Are you ready, Scott?”

“No… What kind of question is that?  Of course I am.  I want to meet Jessie.”

I placed my hand on the doorknob and hesitated.  Should I really be doing this?  Is this a mistake?  God, I hope this doesn’t get out.  I almost chickened out, but I knew I had gone too far to stop.  I open the door, slowly walk out of my room and down the stairs to where Scott was sitting.  Before I could see him and his reaction, he already saw my legs in the stockings and heels.

A wolf whistle met me.  “Oh, my Jessie.  Your legs…”

As I made my way down, he saw the whole me.  Jessie.

It was so fun to see his jaw drop.  He was totally speechless.  I had never seen him so speechless with someone of the opposite sex before.

“Oh, my god.  No way.  You.  Jessie?”

I nodded my head.

“You are absolutely gorgeous.  If I didn’t know any better…”

“You’d?”  I finished.

“I would have easily mistaken you for a woman.  You are gorgeous.  I mean seriously.  I don’t see how a guy wouldn’t ask you on a date.”

So, the tables have turned.  I half-jokingly stated, “Okay Studmuffin.  Are you putting your money where your mouth is?”

“Quit joking around, Jessie.”

I called his bluff.  “Well, you are calling me by my alter ego name.  And no.  I am not joking.  If you are serious, ask me on a date.”  

“I…  I um.  I have to get going.  It is late.”

I blocked the door so he couldn’t just leave.  “So you push me on taking the pill question, you insist on seeing me dressed.  You at least owe me an answer to my question before you leave.”

“Jessie.  Please not now.”

I look deep into his eyes, trying to figure out what is going on in his brain.  Suddenly something clicked.  My egg was cracking, and cracking fast.  It was so strange.  Just hours ago I was strictly a straight genetic male.  Never a thought of considering a permanent change even though I had a secret feminine side of me.  Now here I am, dressed as a woman in front of my best friend, thoughts swirling in my head all because of one simple question earlier tonight.  To this day, I don’t understand why, but I closed my eyes and gave my best friend Scott a soft and sensual kiss on the lips.

I opened my eyes, expecting the worst.  All I saw was Scott totally dumbstruck by what just happened.  “So, would you ask me on a date?” I asked.

It was dead silence, he was peering into my soul with his eyes.  It was awkward yet something comforting.  His left hand went to my cheek and he adjusted my face just enough for what was coming.  He moved in and gave me a kiss. The kiss was followed by more kissing, then with tongue.  It was electric.  I was getting tingly and giddy all over.  Never would I have thought a male would turn me on.  Especially the brother of the woman I so loved but could never state it.

But there was a growing warmth inside of me.  Turning into a burning fire of desire.  I was melting like butter by his lips touching mine.

Scott unexpectedly picked me up and hoisted me over his shoulder.  He turned away from the door and started to walk up the stairs.  All I could see was his nice ass, just inches from my face as he carried me up the stairs.  Then he walked into my bedroom and tossed me on the bed.

I was laying there looking up at him.  I could feel the vulnerability of being in a submissive position and not knowing what Scott was going to do.  He got on top of me and kissed me some more.  The fire inside was turning into an inferno.  I wanted Scott, and I wanted him badly.  He continued by nibbling on my ear lobe and kissing the nape of my neck.  This only amplified my desires.  Desires that I have only felt for the first time just minutes ago.

He moved down to my chest area.  Because of a medication I am on, I did have roughly A cup breasts.  I was worried that if my bra and forms came off it would remind him that I am a genetic male.  Eventually, Scott didn’t care.  He rubbed my breasts through the Red Riding Hood corset.  Small touches that made me start to squirm.  For the first time in my life, a man’s cock was totally on my mind.  Sure when I dressed up and used my dildo on myself I imagined it was a real cock, but this was different.  Instead of just a faceless and body-less silicone cock, I now am with a body and a face that I desperately want to make love to.

I reach down to his crotch and feel a good-sized bulge growing in his pants.  I rub his jeans, hoping to feel it grow more.  I wasn’t disappointed.

“You want my nice hard cock, Jessie?”

I nodded my head.

“Say it out loud, Jessie.  I want to hear you tell me how bad you want my cock.”

In as much of a feminine voice I could do, I said, “Scott baby.  I want you to make love to me.  I want your cock deep inside of me.  I want to feel every thrust into me.  I want to hear you moan and grunt as you drop your seed inside of me.”

I have no idea where that came from, but all I could say is that it was the truth.  I would take the pill in a heartbeat to be Scott’s girlfriend, his lover, his wife.  Oh, how I wish he could get me pregnant tonight.  I would love to carry his babies and grow old together.  My thought was interrupted when I felt my panties moved to my knees, exposing my smaller cock and rosebud.

Scott quickly unsnapped his pants and dropped them.  Next, he pulled his underwear down and then I saw it.  His cock. Drooling with desire.  I tried to reach down and stroke it.  I wanted his precum.  He backed away.

“Jessie, there is plenty of time for that at a later date.  Right now, I am going to take you and turn you into the woman you want to be.”

“Fuck, Scott.  I so want your cock.  Make me your woman tonight.”

I reached into my nightstand and pull out some lube and condoms.

“Your pussy is mine, Jessie.  I don’t think we’ll need birth control.  I’ll take a risk on getting you pregnant.”

Oh my god.  How did he know I thought about that?

He moved my legs up to my chest, exposing my little-girl cock and boi pussy.  I felt the coolness of the lube as he slid a finger up my pussy.  Next, he lubed up his hard cock.  I felt the head slip around the opening.  As relaxed as I was for this moment, it was evident that it would be a tight fit inside.

He pushed just enough for the head to enter.  I gasped at this sensation.  It was so similar yet so different than the dildo of mine.  Scott backed off and pushed in again.  This time more of his head entered into me.  I gasped yet again.  He was a wonderful and caring lover.  He made sure each time he entered it was firm yet gentle.  He gave me time to adapt.  The next thrust he got past the first sphincter muscle.  I lost my breath.  He asked me if he should stop.

“Scott, you are being extremely gentle and caring.  I want this.  I want you inside of me.”

The next thrust in he hit the second sphincter muscle.  It felt like he was splitting me apart.  I let out a yelp and cried a little bit.

“Scott, break it.  Get past my boi hymen.”

The next push I felt his cock slide past the last point of resistance and settle inside of me.  I totally lost my breath.  I’ve had my dildo in this deep, but there was no comparison to Scott’s magnificent cock inside of me.  It hurt, yet in some odd way it was also comforting and felt really good.

After I caught my breath, I wrapped my stocking and high-heeled legs around his back.  My arms went around him, and I kissed Scott on the lips.  I whispered into his ear. “Fuck me.  Fuck me good and hard.  I want your babymakers deep inside of me.”

Scott started thrusting in and out of me.  Changing rhythm periodically then stopping deep inside.  I thought this was the end already.  But no.  It was just the beginning.  His cock drove in and out of me for over an hour.  I was his little sex slut and I loved it.

Finally, Scott rotated me so my pussy was up in the air, and my head was on the pillow.  One of the most vulnerable and submissive positions to be in.  He drove his cock inside of me.  That walnut-sized prostate inside of me starting to swell.  I knew what was cumming.

“Oh Scott, don’t stop.  I am about ready to explode.  Fuck me just like that!  Keep going!  I want your cock inside of me as I explode!”

Scott pounded into me.  My walnut started to explode.

“Oh god!  Oh god!!!  Oh fuck Scott, I am cu….”

I couldn’t finish as something I had never experienced before washed over me.  My eyes rolled back in my head.  My legs started shaking.  Then my body.  I had no clue what was going on, but is was the most pleasurable thing I have ever felt.  Wave after wave of shaking uncontrollably.  Then I felt it.  My little cock erupted an amount of cum that I never shot before.  What made it amazing is that I was soft and it didn’t spasm.  

When I settled down, I was spent.  But Scott kept going.  After a couple of minutes, I could feel that same build-up occur.  My body started a second wave of orgasmic bliss.  Then I felt it.  Scott slammed deep inside of me and held in there.

“Oh god, Jessie!   Your pussy contracting so hard!  Oh god.  Oh yes…  I’m cumming inside of you!!!”

“Shoot your seed deep inside of me!”

Scott’s cock spurted deep inside of me.  After a while, Scott collapsed onto my back.  His hard cock still inside of me, we rotated around so we were laying on our sides.  His cock stayed inside of me, but it was shrinking and coming out fast.

When his cock finally exited my boi pussy, I felt sad. Empty.  It was kind of a letdown to a phenomenal hour.  About a minute later, I could feel some of his cum dribble out of my pussy and to my crotch.  It was unexpected, but it made me smile, knowing he did cum inside of me.

I was worried about the post nut regret that would come to Scott, but thankfully it never came.  He wrapped his arms around me, keeping me secure.  Scott kissed the nape of my neck and whispered to me.

“Now would you take the pill?”

Without a moment of hesitation, I replied, “For you, absolutely.”

More kisses and cuddles, then I asked, “Will you take me on a date?”

Scott kissed my neck some more. “How about dinner tomorrow at 6 PM?”

I was giddy with excitement.  I couldn’t wait to see where this will go.