Never in my wildest dreams would I have thought that my first time would have been with a woman.  I was born a genetic male, but growing up, I always knew that my body didn’t match who I am.  My early life was miserable as I was always ridiculed by my classmates in my little home town.  I finally graduated from High School and moved out of that horrible place and started college in Seattle.  College was so much better.  My roommate Kasey, was a beautiful red-headed woman who just oozed confidence and sensuality.  Kasey was also my first.

What made my first time with Kasey so amazing is that I really didn’t have an interest in women, primarily due in part that I had a penis which I detested so much.  That penis and the fact I was a woman trapped in a man’s body did me no favors in life.  I was constantly harassed growing up and it impacted me deeply.  Just prior to making love with Kasey, I had met Charlie.  He was my first kiss, my first set of butterfly induced feelings.  I loved the feeling that Charlie gave me.  Unfortunately, I left before things got too hot.  I was so terrified of something bad happening to me.

When I got home, Kasey comforted me.  It started getting hot in the apartment as her comforting me soon turned into very passionate love making.  Even though I detested the penis between my legs, Kasey’s mind, beauty, and inherent yet hidden love for me took me to a place I had never experienced.  Our lovemaking helped me beat the odds as my hormone replacement therapy was supposed to prevent any erections or sperm production.

After Kasey and I made love with each other, we stayed naked as we spent the rest of the evening eating dinner on the couch, watching her favorite shows, and cuddling with each other as night made the room dark.  Many times during the evening, we kissed each other passionately and gazed in each other’s eyes.  It was clear we enjoyed each other’s company.  It was clear we had a connection.  But it was becoming even more clear that we were falling for each other.

As tiredness started to overtake us, we kissed passionately one more time.  Kasey got off of the couch and grabbed my hand.

“Come on hun, it is time for bed.”

I looked up to Kasey, and let her lead me off of the couch.  While still holding my hand, she walked us into her bedroom.  No further words were said that night.  Kasey proceeded to put on a pretty red teddy with lace trim. It did an amazing job of accentuating her figure.  It was sexy yet not slutty.

I stood there still naked, my hardened penis pointing out toward Kasey.  I thought, god I so hated this piece of me, it screamed that I was a genetic man and not a woman.  Kasey looked at me and tossed a similar teddy that was black.  I put it on and was amazed how it clung to my body, making me feel sexy.  The only issue was my penis.  The damn thing wouldn’t simmer down.  Sensing I was a little uncomfortable, Kasey looked at the bulge near the hem of my teddy.  She smiled, grabbed my hand and crawled into bed.

I also crawled into her bed.  Her soft silky sheets were driving my senses wild.  I never had or wore anything silky, and the feel was amazing.  Kasey grabbed her sheets and blanket and covered us.  Her final acts before falling asleep were to give me a kiss, wrap my arm around her, and spooned inside of me.  My penis which never settled down nestled into the crack of her beautiful bum.

Kasey fell asleep pretty quickly.  I on the other hand struggled to fall asleep.  My mind flashed back what happened during the day.  I was so confused about the events and what transpired.  I really hated that penis of mine, yet it gave me more pleasure tonight than any other thing in the world, and it was all due to Kasey.  I contemplated what I should do, many circumstances going through my head.  I’m sure that I was falling for Kasey, yet I really didn’t want my penis, and I wanted to have someone like Charlie make endless love to me.  Eventually, sleep overcame me.  It was late, and I knew it would be a tough day tomorrow.

I woke up in the morning, Kasey’s big green eyes staring intently at me.

“Good morning babe.”

I replied back, “Good morning hun.”

She leaned in and gave me a nice sensual kiss.  “Have class this morning?”

“I do.  It starts at nine.”

Kasey frowned a little, “Such a bummer.  I was looking forward to being with you this morning.”

Kasey’s hand found the penis I so dreaded, and started stroking it.  I hesitantly said, “Oh Kasey, please don’t”

A wicked little smile came across Kasey’s face, she had me, and she knew it.  She leaned over and started to kiss me.  Wow!  I had those same fireworks as I did when we kissed for the first time last night.  I so wanted her to love me forever.  Kasey was the one I wanted to love forever.  It seemed to destined to be.

She slowly continued to stroke my penis as she slipped her tongue into my mouth.  We kissed sensually and passionately, each time became deeper and more frantic.  We were getting increasingly hot for each other, yet the conflict about my penis still weighed heavily on my mind.  Kasey now had me rock hard, and she rolled me over onto my back.  She removed the sheets off of me, and then straddled my stomach. 

I was breathing heavily.  It was a beautiful sight.  My breasts were rising and falling with each breath I took.  Above my breasts, I could see Kasey’s hourglass figure over my stomach and her pert breasts.  The most beautiful sight though was her nice full and pouty lips with her green eyes and red flowing hair that covered the front of her shoulders.  She looked like a goddess to me.  She was a goddess that could take any man or woman and cast a spell on them.  Kasey had done that to me.  Medically speaking, my hormone replacement therapy should have gone beyond the ability for my penis to be anything but a useless little appendage that I would only be so happy to never have again.  However, Kasey’s spell resulted in me having an erect cock, rearing to go another round with her.

Kasey looked deep into my eyes.  I could feel her soul peer into mine.  She lifted her body off of my stomach, shifted her weight back, and then lowered herself onto my swollen penis.  I couldn’t believe that I was going to have sex with a woman for the second time in my life.  As my penis reached the pedals of her flower, small shocks of electricity coursed through my body.  It felt good.  No, make that, it felt really, REALLY good.

As she neared the end of lowering herself completely onto me, she let out a moan of pleasure.  I started to reach for her, so we could have body to body contact, but she grabbed my hand and lowered it back to my side.  It was clear to me at that moment that she wanted full control.  Ever so slowly, she started to raise herself.  She stopped just as the tip of my penis neared the entrance of her vagina, and then she lowered herself.  This time though, she bucked her head back, and did more of a grinding motion with her body.  To this day, I don’t know what she did, but she hit something right which caused both of us to moan very loudly.

Kasey continued to control the pace and depth of my penetration into her.  It was such a beautiful sight seeing her ride up and down on my only piece of man left in my body.  I loved how her nice pert breasts shifted and slightly bounced with each cycle.  It took some time, but I noticed that Kasey started to speed up the rhythm of her rise and fall.  It felt so good to me that I was starting to get that familiar feeling in my cock that I had for the first time the night before.  Soon she was starting to get frantic.  Kasey was losing it.  Her own orgasm was rising from within as she continued to rise and fall on me at a faster and faster pace.  Suddenly, she stiffened up.  Her eyes were shut, and her mouth opened.  It seemed like she was frozen in time.  Not a muscle was moving on her, and not a sound came from her.

Suddenly, she cried out in orgasmic bliss as her body started quivering.  I could feel the walls of her pussy contract around my only piece of manhood.  Her contractions were so strong that it started to have an effect on me.  My penis grew inside her and got incredibly hard.  It was harder than it had ever been in my lifetime.  Suddenly I moaned as my own orgasm washed through my being.  It was amazing as every nerve felt on fire. 

I was desperately trying to hold back my first contraction of my manhood inside her.  Kasey seemed to have known that I also was also on the verge of my own orgasmic release.  Her pussy still contracting around my penis, she managed to look right into my eyes.  It was the look of love and lust.  It was the look of a wild mare getting what she needed from her stallion. It was the look that she wanted me to release inside of her.

Finally, I couldn’t hold back.  The first contraction of my manhood released all of the pent up oxytocin.  Waves of love and orgasm coursed through my body, and my womanly seed, now rushed inside my newfound lover Kasey.  The second contraction of my manhood released more of my seed deep into Kasey’s vagina as she had made sure to sit fully on top of me. She gave me a sly little smile as she continued on with her own orgasm.  My third and forth contractions added even more of my womanly seed into Kasey.  Maybe I was imagining it, but it sure seemed that Kasey could feel what was happening inside of her.  My fifth and final contraction, only a small amount went deep into Kasey.  Her orgasm also wound down.  We were both spent.  There was no way we would be able to go another round.

Kasey and I stayed coupled together, neither one of us wanting to break the bond between us.  She lay on my chest and gave me several deep and passionate kisses.  We stayed like this until my only piece of manhood finally shrunk to the point that it slipped out of her flower.  Some of our juices dripped from her pussy onto my crotch.  It felt so wonderful to have our coupling dripping onto me.  Kasey wrapped her leg over my stomach and placed her head on my breast.  Both of us enjoyed the most beautiful thing any couple could do.  We were joined as one.

We stayed in bed for the rest of the morning, each of us taking turns initiating passionate kisses to each other.  Neither one of us felt the desire to get out of bed, as this was something so beautiful, that neither of us wanted it to end.  Around noon, Kasey finally propped herself onto her side, her arm holding her head up.  Silently, Kasey and I soulfully stared into each other’s eyes. 

Finally, Kasey said, “Jessie, were do we go from here?”

I briefly thought about all I had gone through and what I wanted to do.  But now there was doubt about me wanting to complete my transition.  I truly hated my last symbol of being a man, yet the last twenty-four hours it gave me so much pleasure.  I wanted Kasey to love me and be my partner forever, yet would she want the same if I went through and completed my transition to womanhood?

I broke down and started to cry.  “Kasey, I want us to be together.  I love you.  It’s just….  It’s just…”

Kasey interjected, “It’s that you want to complete your transition and are afraid you would lose me if you do.”

“Yes.”

“I am falling for the person inside you, Jessie.”

We looked into each other’s eyes as I cried in relief.

“I love you Kasey.”

“I know.”