My first time

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Brunette

It was my eighteenth year, and I was ready to start my new adventure.  It was really sad to see the summer go so quickly, but I also realized that a whole new life was in front of me.  My bags were packed with my belongings and I was ready to get out of this miserable town and on my way to the big city.  I was looking forward to meeting people who didn’t know my past, and would only know me as me.  Of course, I still had to be very careful, but at least I didn’t have to put up with the close-mindedness that my own hometown had toward me.From a very young age, I realized I was different.  I was a boy that never liked the stereotypical boy things such as sports, boys clothing, getting dirty, and catching creatures.  Instead, I had a female best friend named Tracy.  We would play house with her dolls and I always wanted to be the mom, we dressed up like princesses and wore makeup, and shriek when boys came at us with mud or snakes.  When I went to school dressed up as a boy, I hated every minute of it.  Boy clothes were so boring, uncomfortable, and just plain ugly.  Instead, I preferred the soft fabrics and the dainty nature of girls clothing.As I grew up, I tried to express myself more and more as I wanted to, and less about how society thinks I should express myself.  Even though my parents signed off on my behalf to take hormones, which helped me develop a really nice womanly figure, I was ridiculed and teased mercilessly.   My best friend Tracy tried to stick up for me when anyone started teasing me.  Unfortunately, though, she also would be treated really poorly.  I guess it was guilt by association.  It was really unfair because Tracy was one of the nicest people I ever knew.My senior year was the worst.  Even though it didn’t start off being teased or made fun of as I had anticipated, I was soon to learn it was short lived.  A guy named Steve asked me to go with him to the Homecoming Dance.  I was surprised, because even though I looked more like a young woman than a young man at this point, I never really considered my sexuality and what kind of person I found attractive.  I was so caught up with the fact that I was asked to the dance, that I really didn’t consider why.  Either way, I thought this was the year that I started to be accepted for who I am.  Oh, how wrong that turned out to be.The night of the Homecoming Dance, I was dressed up in one of my more pretty formal dresses, ready for my date to pick me up.  Steve was a total gentleman to me in front of my family and while in the car to dinner.  We met up with several of his friends and their dates at one of the nicer restaurants in our town.  I had a lot of fun and was finally getting comfortable with everyone.  Then we headed for the dance, and that’s when it all fell apart.My date’s friends did some not so nice things to me at the dance in front of the other classmates.  Everyone was laughing at me, calling me derogatory names, and one girl even intentionally ripped my beautiful dress.  Only Tracy tried to stop what was going on.  Unfortunately, too many classmates were involved in hurting me emotionally that she was powerless to stop it.  I thought that my date was protecting me when he took me out of the school in what appeared to be a protective way.  But as soon as we got to the middle of town, he stopped the car.  He looked at me called me a freak and tranny, then he asked me to leave his car. I pleaded for him to drive me home, but all that did was make him madder.  He finally physically removed me from his car.  One of my high heels broke, and my dress was ruined.  My purse got lost during the school fiasco, so I had no phone to call my parents.  I sat on the curb.  It was midnight, and here bursa escort I was crying on the corner of Main Street.  To add insult to injury, not a single person stopped their car to check up on this crying young woman.  This is why I wanted so badly to get the hell out of my hometown and on to bigger and better things.Graduation couldn’t come soon enough, but once it did, I was just three months away from a new start.  My parents, brother, and sister gave me the best graduation gifts I could ever want.  My older brother handed me the keys to his old car, my sister took me out on the town for a new wardrobe, and my parents helped me make everything official on my driver’s license and birth certificate, so I was known as a female named Jessie.  They also gave me $30,000 towards whatever surgery I wanted to have to help complete me. The day I moved out was a bitter-sweet day.  I was so glad to leave my hometown, yet sad to leave my brother, sister, and parents.  After my hometown was no longer visible in the rearview mirror, it was like a huge weight was lifted off of my chest.  Now it was just me, and the road ahead of me.  After two days of driving, I finally made it to my new hometown of Seattle.  It was prettier than I had ever imagined. As I was moving into an apartment near the college, I noticed that several guys would look at me and smile.  After taking my third load into the apartment, two guys actually helped me move the rest of my belongings.  It was so different than my hometown that I thought I was in a dream.   Later that evening, I met my roommate Kasey.  She was a gorgeous lady, and we hit it off immediately.  When I finally settled down, I knew I would love it here.My first week of classes went very well, except for the moment where my backpack opened up on me and spilled my textbooks and class notes all over the ground.  As I bent over to pick them up, I saw a hand reach down and pick up my biology book.  Looking up, I saw a most handsome looking guy.  He smiled at me and told me his name.I replied, “Charles, it’s nice to meet you.”He grabbed my hand and helped me up to my feet.“And your name?” Charles asked of me.I started blushing, “Umm, Jessie.  Jessie is my name.”“So nice to meet a beautiful lady such as you.  Do you care to get a cup of coffee?”I looked at my phone and figured I had enough time before my next class.  “Sounds nice.”Charles took my hand and we walked to the campus coffee shop.  While there, time seemed to stand still.  It only seemed like minutes, but two hours had passed.  I had looked at my phone to see the time.“Oh no!  I’m late for my Shakespeare class!”Charles smiled at me.  “Skip the class and stay.  I am really enjoying your company.”My half-hearted reply was, “I can’t.”Charles saw in my eyes that I didn’t want to go.“Here, let’s go back to my place, and we can continue to talk.”We walked a block off campus, where Charles lived in a rental home.  I came to find out that he and his two best friends rented the house together.  We sat on the couch talking more about our first week of classes, and what we wanted to do in the future.  After a while, there was an awkward pause between the two of us.  He leaned over and kissed me on the lips. I have to admit that even though it was my first kiss with a guy, and I still wasn’t certain I was attracted to guys.  The kiss gave me butterflies in my stomach, and a wave of euphoria swept over me.  I leaned over and gave him a kiss.  Soon our tongues were exploring each other, doing an erotic dance between our mouths.  As soon as I felt his hand reaching for my thigh, I immediately froze and backed away.“Jessie?  What’s wrong?”“Um.  Nothing.”“Why did you pull bursa escort bayan away?”“Well, um.”  I was thinking in my head what I should say.  “Um.  I think I need to leave.”I started to get up, but Charles grabbed my hand and stopped me.“Come on Jessie, what is wrong?”“Well, I’ve never done this before.”“Never?” was Charles reply.“No.  You were my first kiss.”“Come on, a girl as pretty as you?”I responded, “Yes.  It’s true.”“How does someone so beautiful get into college without ever kissing a guy?”“Well, um… ” I was clueless how to respond.  All I know is that I didn’t want to end up in the same situation as I had during Homecoming, or worse, beaten up and or killed because of who I am.Charles asked me to sit down.  I kept stuttering in fear.  Charles finally smiled and kissed me again.  “Your secret is safe with me.”I looked at him with an odd look. “What do you mean?”“There’s no need to be nervous telling me why you’ve never been kissed before.”I thought long and hard about what to say next, but I kept thinking back to my high school experiences.  The words just wouldn’t come out.“I have to leave.”I quickly got up and headed for the door.  Charles begged me to stay, but I was bound and determined to leave.  I opened the door and as I was heading outside, I heard a very dejected Charles call out, “Please don’t go, Jessie!”On my way back to my apartment, I contemplated what happened at Charles’ place.  A big smile formed on my face when I relived the kiss he gave me.  Lots of fireworks and a warm feeling from within was a great thing.  The drawback was that I was no ordinary girl.  I was so afraid that he would get mad if he found out about my secret, and that he would make me a statistic.  Yet, there was a pang of regret that I didn’t stay and continue our day together.I walked into my apartment and saw Kasey cooking something for dinner.  She saw me and immediately ran to me and gave me a big hug. She looked me in the eye and said, “Glad you’re home!  I was worried when I didn’t see you in class, and when I got home you weren’t here.”I thought about it and realized she was right.  I should have been home.  “Sorry, I met a really nice guy between classes.  I lost track of time.”Kasey smiled at me and continued, “A guy?  Was he cute?”“Of course!  Otherwise, I wouldn’t have missed class!”“So what did you do?” Kasey asked.I started to blush and a smile came across my face, “We had coffee then went back to his place.”Kasey egged me on, “Oh?  You’re blushing.  What else happened?”I shyly replied, “He kissed me.”“And?”“I left.”Kasey’s face was priceless, “You left?”I looked at her and reaffirmed that I had left.Kasey gave me a slightly stern look, “Why did you leave?”I looked at her with a little fear in my eyes.  She sensed it and gave me a hug.  “Are you OK?”“I um..” Here we go again was all I was thinking.  What do I tell Kasey?  Today I went from a major high of my first kiss to two different lows.  I was so terrified of repeating my high school experiences that I started crying.Kasey looked at me with compassion in her eyes and held me close.  She started caressing my back and telling me it’s okay.  After a couple of minutes, I settled down, and the tears stopped running down my cheeks.  My mascara was ruined, but in all honesty, it was furthest from my mind.  I finally lifted my head off of Kasey’s shoulders and looked at her eyes.  That was all it took. One soulful moment where Kasey’s beautiful green eyes looked deeply into my watery and reddened eyes.  Kasey slowly closed her eyes, moved her lips toward me, and stopped just as our lips made contact.  It was a very soft yet sensual kiss that made me jump back a little.  Never escort bursa in my life had I felt a jolt of electricity as that kiss. Surprised that I jumped back from her, Kasey looked at me with a look of sorrow.  I knew that my jumping back was the cause of her sorrow, I had hurt her.  I looked at her eyes again.  No words were said between the two of us, only our deep and soulful gaze into each other’s eyes communicated what we wanted.  My hand touched her cheek as I leaned in to kiss Kasey again.  More electric shocks coursed through our lips.  Both of us felt the connection, and for the first time since I started taking hormones three years prior, I felt something stirring between my legs.I backed off before I got too worked up from kissing Kasey.  She looked at me in confusion and stated, “Are you okay?”“I am more than okay, I’m elated,” I replied.Kasey continued, “I don’t understand.  If you are elated, then why did you back away from me?”I looked down at my feet, “I…  I, um… Well..”“Jesse, hun.  Whatever it is, you can tell me.”“I ah… I’m not who you think I am.”With a quizzed look, Kasey asked, “What do you mean by that?”I finally broke down my defensive guard, “I am a girl with something extra.”It looked like Kasey was hit by a bus.  “What?!?!”“Yes, Kasey.  I am a girl, but I wasn’t born a girl.”“No way!  That is not possible!  You look…  You look so… girly!”I was saddened by her shock but I still managed to say, “It is possible, and that is me.  I am so sorry that I deceived you.  I think…  I think I’ll pack my stuff and go now.”Kasey grabbed my arm and loudly proclaimed, “NO!  I want you to stay!  You just surprised me.”“Are you sure you are alright having a transgender as a roommate?”“Jesse hun, I am more than okay with you being my roommate… and hopefully more.”I stared into her eyes.  Kasey was sincere with what she said.  We mutually leaned into each other and kissed again.  This time it was more than a sensual kiss.  It was one of love and lust.  Our kisses became more frantic and erotic.  Soon our tongues were dancing in each other’s mouth.  They were playing a tango that only the two of us would understand.  It was obvious that we wanted each other, badly.Even though my something extra had shrunk back down to size from the exchange, I found that I was becoming increasingly hot for this woman.  My extra package started to grow again for only the second time since my hormone replacement therapy started.  I was shocked, slightly repulsed, yet pleased that something that was not supposed to work was now working.I fell onto the couch, and she fell on top of me.  Our hands started exploring each other’s body.  It was so amazing to actually be touched in such a loving way.  I gently caressed her breasts through her blouse as she did the same to mine.  Eventually, my hands made their way under her blouse.  I proceeded to lift her blouse over her head and took them off.  Both of us smiled and then giggled at what was happening.  Her beautiful breasts were held within a sexy lace bra.  It was a complete symbol of her femininity, a symbol that I hoped mine would look so sexy one day. My thoughts were interrupted when Kasey reached behind her and unclasped her bra.  It fell onto my chest, almost like it was begging to hug my own breasts.  She, in turn, removed my shirt and bra.  We were two partially naked females immersed in each other’s love and lust.  I was falling in love with her, and I knew I would never ever want to love anyone except Kasey.Suddenly her hand made its way to my something extra.  Based on the expression on her face, she was very pleased with what she felt.  Kasey lifted my skirt and pulled down my panties so my something extra was now out in the open.  She looked into my eyes as she lowered herself toward my hardened shaft.  We never broke eye contact as her tongue reached out to the tip of my hardened cock.  I moaned as her warm soft mouth surrounded the shaft of the thing that I hated so much.

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