My Life Pt. 03

Shemale

This is a continuation in the My Life series. It does assume you’ve read the other parts, so if you are coming across this for the first time you should start at the beginning. I do try to write each story to stand alone, but its better if you know the history.

*

I was on cloud nine as I walked up the steps to my house. It was mid-morning and a beautiful day. I was no longer a virgin and the world seemed to be celebrating this. The sun was out, the birds were chirping. I felt really good. I was surprised.

I mean, when I went to Mr. Moran’s house last night any number of things could have happened. He could have been rough or mean. He wasn’t any of those things, I had to admit my Mom was right; he was perfect for my first time. I also didn’t know if I would feel dirty or weird after, he was much older and my English teacher after all and we have a complicated history. I didn’t. I felt like this is what my body was made for and all was right with the world.

I opened the door to the kitchen (our house was laid out kind of weird) and there was my Mom with a beaming smile on her face and a cup of steaming coffee. She welcomed me home with a big and knowing hug. I once again marveled at my gorgeous and amazing Mom. I had just had sex for the first time, she knew it, practically encouraged it and here she was welcoming me home. Not for the first time I realized how lucky I was to have her.

She handled her son needing to become her daughter (I’m Trans if you are just joining us) with grace and acceptance. She prepared me well for the world and this next step in it. It was such a wonderful feeling.

“So, my young lady has become a woman.” She said once she saw me blush. “Tell me everything and don’t you dare skimp on the dirty parts.”

My Mom was like that; very open about sex and sexuality. I was slow to start. I am really shy by nature and not as forthcoming as my Mom about these things. Once I started though it all just came tumbling out. She listened intently and smiled and nodded a lot.

“So you like men then?” she asked when I finally wound down.

“Yes!” I started, then immediately realized the import of the question, “Well I mean yes I like men, but I think I like girls too, I just don’t know.”

“Don’t worry Sweetie,” she replied in a motherly tone “you’re young and you’ll figure it out.”

Spending the night at Kelly’s

Preparing for my sleep over at Kelly’s was nerve wracking. OK, so I am 18 years old, you’d think I would have a better handle on things like this, but if you read my history, well you know how big a deal this was for me. It was going to be my first sleep over with my first friends ever. I was also going to drop the bomb about my gender. There were just too many unknowns and so I was nervous to the point of shaking.

As a result of all this, I started preparing early and I prepped like it was going to be an arctic expedition, making a checklist of everything I needed. I dressed in casual comfortable clothes, just a light floral pattern dress, yellow with blue delphiniums on it and a pair of simple flats. I did my hair and makeup with in a relaxed and casual look with studied precision, a contradiction I know but that is how I felt. The process helped.

I have to admit that there was one point that I broke down crying and almost backed out of the whole thing. It came when I was doing the simple daily think of tucking my penis away and pulling on some panties. It’s not terribly big and as I have stated before I love it and would never part with it, but this one time it made me feel like the biggest fraud in the world. I was sure, absolutely convinced that my new friends would hate me and everything would be awful.

Fortunately my Mom walked in on the middle of this freak out and gave me a pep talk. Before long I was smiling and once again ready to go. I can never say enough about how important she is to me. She ended with a piece of advice that I will always remember.

“Tonight you’ll be looking for truth. If the truth is too much for these girls to handle, then they never really were your friends. If it goes badly, you always have my love and you’ll find the right friends some day.”

That statement gave me the courage I needed to keep going. Two hours later I pulled up at Kelly’s house in my crappy little Honda Accord. I walked up the path through her well-manicured yard and rang her door bell with an arm full of stuff (purse, bag of clothes, makeup bag and pillow) and a tummy full of butterflies.

Kelly’s dad was an older, balding, black man with a big belly, glasses and a welcoming smile. I instantly loved him, he was just so cute! To answer your question right off the bat, yes I totally would have slept with him. The things you pervs make me think about, gosh!

I guess my taste in men is kind of weird. He was just so nice and I find that really attractive in a guy. He welcomed me in and took my stuff off my hands.

Kelly’s mom was an enormous blonde white woman. By enormous I mean Kartal Fetiş Escort she was big all over but in a really attractive way, she had big hips and gigantic tits, she was the kind of woman you just wanted to hug and fall in to. I didn’t have to wait long either, as soon as she saw me she enveloped me in a warm, if nearly crushing embrace.

“You must be this Tammy we keep hearing about.” She gushed.

“Yes Ma’am” I responded on my best behavior as my Mom taught me.

“Oh stop all that, you call me Clara and that fat bald guy over there is Tom.” I laughed at this.

“Thank you both, you have a lovely home.” I replied. It was true too, their house was immaculate and done up in a style that was reminiscent of the 70’s or something.

“Well thank you dear, you’re such a sweet thing, the kids are in the family room.”

She showed me the way. Theresa and Kelly were playing Mario Kart on the Wii when I got there. They were both yelling and laughing as they raced and threw stuff at each other. I had never really played a lot of video games so I wasn’t too sure what to make of it. Kelly eventually won the round.

Kelly handed me a controller and joined me in for another game. Wholly crap it was fun. I lost, badly, but it was hilarious and I loved it. We played for a couple hours and talked about general school gossip while Kelly kicked both our asses repeatedly. By the time Kelly’s parents announced pizza for diner I had completely forgotten about all of my worries.

As a reminder, Theresa and Kelly were my first and only friends that I had met in school. Theresa was what some people would call chubby but I call voluptuously gorgeous. She had big tits, curvy hips, dark hair and big blue eyes. Kelly was a small girl; whip thin with mocha brown skin and big crazy hair. She had these dark eyes that could just look right through you.

Dropping the bomb

After we totally pigged out on pizza we got into our PJ’s and settled down to watch a movie. I honestly don’t even remember what movie it was. We barely got into it before Kelly started tickling Theresa, who in turn started in on me. This all resulted in a general break down of civil society in Kelly’s living room and before long it devolved into an all-out pillow fight. It was all kinds of ridiculous fun.

After a while we became aware that Kelly’s dad was watching us. He had this big smile on his face, which was super endearing. He had come in to tell us it was time to settle down as he and Clara were going to sleep.

We settled down in front of the movie until he left, but as soon as he was gone Kelly turned to me and said “OK, time to spill it.” Theresa turned to me as well, her expression curious.

“Spill what?” I said disingenuously, my heart pounding.

“Your big secret,” she replied, “you said you were going to tell us.

“Yeah,” Theresa said “tell us.”

I looked back and forth between them and my vison started to blur as my eyes filled up with tears. I was so afraid of what they were going to say, how they would react. I loved these girls with all my heart and I didn’t want to lose them.

Theresa saw my eye first and the compassion on her face was heart breaking. She moved to hug me, to tell me it was OK, but I stopped her. “No.” I said, “let me get through this and if you still like me then please hug me all you want.” The tears finally broke and rolled down my cheeks. I was sure a dark line of mascara followed but I didn’t care.

“I am not what I look like.” I began. They both looked back at me quizzically.

“I… I…” god why did this have to be so hard? I looked away as I said it, my voice cracking just above a whisper.

“I wasn’t born a girl.”

“What?” Kelly asked as if she didn’t hear.

Again with more strength I looked her in the eye and said, “I’m trans, I was born a boy.”

“Oh my god” Theresa responded in a quiet voice and unreadable tone. I looked away again, tears flowing freely down my face now.

“Wholly shit!” Kelly said, “Are you for real?”

I wiped my face and looked back at her incredulous at her response, totally not what I was expecting. “Yeah” I replied.

“Wow that is fucking amazing.” She said, shaking her head.

I still wasn’t sure how to read their responses. It was just too much and I broke down sobbing, full on body wracking sobs. A little voice in the back of my head was chastising me “Gawd what a baby!” it said.

Then it happened. Theresa tackled me, wrapped her arms around me. For a second I thought she was going to try to hurt me. Instead she was giving me the biggest and strongest hug imaginable.

Then I felt another pair of arms go around me from behind as Kelly joined the hug and I just shook and sobbed uncontrollably into Theresa’s shoulder. The crying went on for some time. The emotions were just too much for my feeble mind to handle. They were both soothing me with soft nothings like “sshhhh, ssshhh” and “It’s going to be OK”

After a while Kartal Gecelik Escort my faculties returned enough to ask the burning question “So you guys still like me then?”

“Of course” Theresa the compassionate one responded immediately.

“No!” Kelly responded, then followed with “We love you, you dumb ass!” Ever the drama queen that one. I couldn’t help but laugh.

They held me a long time as we did the laugh cry thing. For the longest time the only other human being in my life was my Mom. Mr. Moran was fun, and I definitely felt something for him, but it wasn’t this kind of closeness, this bond. This, this was something altogether different. I needed this.

As the weight of the world finally floated away off my shoulders I found I could breathe easier. I felt lighter. I had no idea I was carrying so much anxiety around with me. No clue.

After a while they let go and we sat cross-legged across from each other in our PJ’s. T took a wet wipe out of her purse and cleaned up my face. She cleaned hers as well, she had been crying too.

Then Kelly looked at me mock seriously and said, “Girl, you got some splainin to do.”

So I did. I started at the beginning, explaining about how I always felt different. I told them about seventh grade and the hospital. That pissed Kelly off big time; I thought she was going to break something. Theresa just seemed sad hearing about it. I assured them both that it was horrible but in some ways was the best thing that ever happened to me.

I told them everything, well everything except the parts with Mr. Moran. I didn’t tell them he rescued me or that we were having sex. I made a promise and I intended to keep it.

Playing truth or dare

After all that seriousness Kelly decided to lighten things up a bit. “Truth or dare?” she said, looking at me, challenging.

“Umm truth I guess.

“Do you have a penis?” she asked.

“Umm, yeah I do.”

We did a couple of rounds in this way, all of us picking truth. I found out both Kelly and Theresa had had sex with past boyfriends, but that it was mostly not satisfying. I also found out that they had fooled around with each other a few times, experimenting.

When it finally got back to me again, I was getting kind of tired of all the revelations. Revealing hard truths can be exhausting.

“Dare.” I replied to Kelly.

“I want to see your tits.” She demanded. Theresa hid her giggles behind her hand, scandalized as Kelly stared at me. I didn’t hesitate at all, just pulled my top over my head. My tits are small but really pretty. I fill an A cup pretty well and can sometimes wear a B depending on style and padding.

“Wow.” Kelly said when I was topless, “that is soooo not fair.”

“What?” Theresa asked as she admired my chest as well.

“She has awesome tits and she was born a boy.” She replied, “Are they implants”

“No,” I replied, “they are natural; well I mean they grew when I started taking hormones.”

“Damn.” She responded as she reached out and gave my left boob a squeeze. “Damn.” She repeated.

The next round Kelly and T also took dares. By the time we were done we all sat facing each other topless. I now understood why Kelly was a bit angsty, her breasts were just small smooth swells on her chest topped with really sexy dark chocolate covered cones. I thought she was gorgeous but I could see why she was jealous.

Theresa was a bigger girl all around, curvy and beautiful. She had the chest full chest of a mature woman, with large pink areolas. She was shy like me and we both sat blushing furiously as Kelly just openly checked us out.

I took dare again, this time from Theresa. “Can we see it?” she asked, the blush spreading from her cheeks to her upper chest.

“See what?” I asked, playing dumb.

“Don’t play dumb with us!” Kelly demanded.

“Ok I said, but let me go to the bathroom first.”

I went into the bathroom, I did have to pee. I took care of business then I untucked my little girl cock. It had been straining to get out anyway and had been hurting quite a bit when the other girls took their tops off.

I came out and sat between them. They were both watching me really intently. I slid my bottoms over my hips revealing my black lace panties. Honestly I would have worn something simpler but I really only had pretty panties. Just my thing I guess. Unmistakable in those panties was the bulge of my girl cock. It’s not very big, about five inches and fairly thin. I think it is a nice match for my feminine body.

Kelly and Theresa were both staring; mouths hung half open, waiting. I took the next step and hooked my thumbs into my panties and pulled them down over my hips. My pretty little cock flopped against my lower belly.

“Whoa” Kelly exclaimed, Theresa was still speechless.

“Can I touch it?” She asked.

“Sure.” I replied nervously, biting my bottom lip as she reached a tentative finger out to touch my now throbbing cock.

“Mmmm” Kartal Genç Escort I moaned, trying to stop myself from cumming right then and there. I was able to hold back.

Then Theresa did the same, looking at me for permission. She touched it gently at first with her long French manicured nails. I squirmed. Then she scooted closer to me and I felt her hand encircle my cock. Her big blue eyes were just inches from mine, her large breast grazed across mine as we stared into each other’s eyes.

“Oh holy fuck, you two are gonna do it.” Kelly exclaimed, then Theresa closed the distance and kissed me. I moaned into her mouth as our tongues met and our breasts pressed together.

Kelly made a strange noise, something like “Ugnh.” and Theresa and I broke our kiss and looked at her. She had a hand shoved into her PJ bottoms and was rubbing slowly up and down. We both giggled at that. Then Theresa shut me up with another kiss, her body drawing me in. I felt a heat on my thigh as Theresa started grinding herself against me as she stroked my cock faster and kissed me harder. I really wasn’t expecting this and it took all I had not to cum.

“Wow!” Kelly exclaimed again between moans.

Silence fell except for the frantic moans of three girls trying to release the built up tension. I slid my hand over the beautiful swell of Theresa’s belly and into her PJ bottoms. She was smooth, shaved and very hot and wet. I slid a finger inside her and it was like heaven when she arched her back and moaned.

This was the first pussy I had ever touched. It was amazing but also complicated in a way my cock was not. I had seen porn, read and heard enough to know that finding her clit is what would get her there, and I desperately wanted to make this girl cum. My own orgasm was threating to burst through and overwhelm my senses.

My PJ bottoms and panties were down around my mid thighs. Theresa stopped rubbing my cock long enough to pull hers down too. She ground her pussy hard against my hand.

It was her hips that did it. Theresa was a voluptuous girl, similar to my Mom. When I saw her hips grinding back and forth, well that was all I could take, Kelly too apparently. As cum started to shoot all over Theresa’s lower belly, Kelly’s body went rigid and started shaking violently as she came too.

Theresa was still grinding on my hand and I could sense her frustration. Then I did the only thing I could think of. I took my hand off of her and kneeled at her feet, working her PJs down to her ankles. Then I moved between her legs and started licking my cum off her belly and moving down.

“Oh holy fuck is she going to…?” Kelly exclaimed.

I was and I did. Theresa let out this long low moan as my tongue reached her clit. Her back arched and she was breathing hard. Everything seemed so load in my ears I thought maybe we might wake up Kelly’s parents.

Theresa’s was the first pussy I ever tasted and I was immediately hooked. I wasn’t entirely sure what to do, but after some awkward experimentation I sucked her clit between my lips like a small cock and started flicking my tongue over the tip. This sent Theresa into an absolute frenzy of bucking hips and moaning so I kept doing it. Her hands tightened in my hair as she pumped her hips against my lips. I could hear Kelly commenting in the background.

Then the world exploded. Theresa’s body shook violently over and over. I held on and kept up what I was doing as best I could as her orgasm took control over her body. I felt such a sense of pride that I was able to get this beautiful woman and my very first friend off.

Then she pushed me off a bit roughly and at first I thought she was mad. Instead she looked up at me with those big beautiful eyes and smiled “Sorry, I get really sensitive after.” she said, and blushed.

We all just spontaneously busted out in a ridiculous giggle fest after that. It was getting pretty late and we tried to settle down all nestled together. Before long and move and a shift turned to a rub and a cuddle and we were at it again. I learned what Kelly tasted like and the feel of her short curly pubic hair against my cheek is a memory that still drives me wild to this day. The both sucked me in turn. By the time we all fell asleep we were so exhausted we nearly forgot to put our PJs back on. Kelly’s dad surely would have seen a sight in the morning when he came in to bring us doughnuts and coffee!

The start of my “Normal” life

The thing with Kelly and Theresa was fun between friends and there were really no awkward feelings afterward. We remained friends, even after Kelly went off to college. Now Kelly has a fiancée and is studying for her Ph.D. in astrophysics of all things. Theresa and I went to college locally and even dated for a while. We split up on mutual terms and really became better friends for it. The sex stuff kind of fell off with both of them in the long run, though I would still gladly give myself to either or both any day of the week if they wanted it.

Things with Mr. Moran eventually petered out too. We experimented with me toping him on our fifth “date” over the summer. It was OK, but just wasn’t really for me. He on the other hand began asking for it more and more. Eventually I had to break it off because it just wasn’t right for me.