Samantha Pt. 01

The beeping of my phone woke me up. The sun was already shining in through the window at full capacity, even thought it was 9:00 AM only. I opened the window to let some fresh air into the room. The early summer breeze felt nice in the morning. I walked over to my table to check on my phone.

It was a series of texts from my buddy Dennis.

D: + Hey! don't forget! You are coming to party with me tonight.

D: +You promised me, 1 party / 3 months

D: +So get your introverted ass ready by 8 pm.

D: +Don't even try to chicken out of this one Gary, I'll come and pick you up anyway

D: +If you need anything call me

"Why did I even agree to this?" I asked myself. Then quickly dismissed the thought of coming up with an excuse to get myself out of this. Since I broke up with my girlfriend, I turned quite antisocial and Dennis took good care of me. I promised him to go to at least 4 parties a year with him, to get me slightly out of my introverted ass. A promise is a promise and he is a good friend, I don't want to disappoint him.

I spent the rest of the day overthinking in slight anxiety. I was walking around the apartment trying to pass the time. I got over my uneasy feelings and got dressed up by 7:45 pm.

"Too soon, again..." I thought to myself.

Then my doorbell rang around 8, it was Dennis. I quickly grabbed my thin coat - since the evenings in may can still be quite cold - and headed downstairs.

"Hi Gary!" Dennis greeted me as I got into his car.

"Zup Dennis? How is it hanging?"

"It's alright, are you okay? Do you have your party-mood with you?"

"You know my party-mood only starts after the 1st jack-and-coke."

"Haha... True enough," laughed Dennis. "Don't worry I got you covered," as he pulled out a bottle of pre-mixed Jack-and-Coke from the glove-box.

"What?... why... I.... don't know what to say..."

"Don't have to say a thing, just have a good time tonight okay?"

"ON IT!" I said taking a big sip from the bottle.

By the time we get to the party I already started to feel loosened up. It was a house party with some 40+ people. The music was already banging on a pretty high volume by the time we got there. After a few short introductions I parted with Dennis and started walking around familiarizing myself with the place and having small-talks every now and then with bystanders, joining conversations (or more like trying) and so on.

I was slowly sipping my booze, carefully not to overdo it but have enough in me to enjoy the party. I was having a decent time actually, just chilling around, minding my own business when I saw a girl. A really cute one, one might say. Wearing ripped jeans, a trendy black shirt with some silly cartoon figures on it. Her blonde hair flowing down onto her white shoulders.

She looked extremely tensed up and jittery. I was checking her out for a good few minutes before I thought to myself. "Aww...Heck, if not now, when? What can I lose?" I quickly finished my drink and went over to her.

"Hi I'm Gary! Are you okay? You look a bit rattled," I said, trying to pull the most confidence out of my voice.

"Hello. Yes, thank you. I am just really nervous," she said with a voice as nervous as she looked.

Then I pulled my worst joke ever that managed to make someone laugh.

"Nice to meet you 'just really nervous'. May I ask, why are you nervous?"

She let out a soft giggle and I saw her relax a bit.

"Sorry, my name is Samantha I'm just not quite used to be around this many people. To tell you the truth I am here because my friend dragged me with herself."

"Kidnapped huh? That makes two of us," I said feeling sympathy for her situation.

"How come?" she asked curiously.

"I promised my friend that I'll go to at least 4 party with him a year. I became pretty anti-social recently and he is trying to get me back up."

"Really nice of him. And how are you coping?"

"I'm doing okay, thanks. Drinks help a lot," then a realized her hand was empty. "You should try some as well, what's a party without some booze, right?"

So, I quickly mixed two glasses of Jack-and-Coke and handed her one.

"Cheers!"

"Thanks," she said quietly.

We had some small talk and casual chatter that I strangely really enjoyed. There was something in her that just got me. She explained that she needs to find her friend because she is known to get into trouble and has hard time handling her drink. She asked me to stay around while she finds her as she disappeared into the crowd.

I checked my phone and saw that I had a text message. It was Dennis:

D: +Hey man! My sister just called me that she had a car accident

D: +I gotta go check on her. Sorry [sadsmileface]

D: +TTYL

I quickly replied:

G: +No problem bro

G: +gotta take care of the family right?

G: +hope she is alright.

G: +see ya!

I really hoped her sister is alright, I met her a few times. She is a nice girl. I went back to lurking around the party for quite some time looking to meet Samantha but she was nowhere to be found. "She probably got bored and went home," I thought to myself and checked the time. It was already around 2 AM, and the party was getting over I decided to call it a day and look for a bus home.

I checked the schedule at the bus stop and realized that I just missed the bus with a few minutes. Wouldn't be a problem normally but since it was night the next one would not come for another 50 minutes.

"Just as my luck would have it," I mumbled.

I am not a big fan of just staying put and waiting so decided that I might as well walk a few stops to kill the time. I walked for a few good minutes and I was about to turn right at an intersection when I heard talking from around the corner.

"Emily, you fucking clumsy drunkard slut get up or I'm leaving you here!" said a familiar voice.

I turned the corner and saw Samantha there with what looked like a totally wasted girl on the sidewalk. The sight was pretty funny, the girl Samantha was trying to get up from the sidewalk was sitting in the familiar 'I'm drunk' position refusing to move.

"Need any help with that?" I asked jokingly.

She probably hadn't realized I was there because she jumped a bit.

"Shit you scared me! Sorry, I mean, Hi Gary!"

"No problem, so I guess she is your friend, right?"

"Yupp, meet Emily. My drunk ass flat-mate who can't hold her drink not one time," she said pointing at her the girl on the sidewalk. "What are you doing here in the middle of nowhere anyway?"

I briefly explained to her that I was heading home on foot since I missed the bus and not a fan of waiting. Then she explained that she found her friend already drunk at the party and decided to take her home that's why I couldn't find her anywhere at the party.

"Answering to your question, yes I might need some help if you have the time. If you offer still stands of course," she added.

"Sure thing! No problem, where is she living?" I asked as I dragged her friend up into standing position.

"Well, she is actually my flat-mate, we are living two corners from here," said Samantha while putting Emily's arm around her shoulder.

"Cool, lead the way!"

The road to their flat was adventurous. Emily kept tripping or dragging us into all directions, sometimes throwing up onto the sidewalk. We generally had hard time staying on our feet because of her. We had a great time and some laughs though. Getting her up to the second floor was a whole other level. The elevator was out of order for maintenance so we had to drag Emily up on the stairs. At least she was passed out of asleep so she was not resisting the helping process.

"Hey, I know you already helped me a lot but can you please give me a hand putting her in bed? I don't really have the strength to do that," Samantha asked when we reached their door.

"Yes of course," I replied, "I wouldn't leave you with this thing in this condition," as I pointed towards the half unconscious Emily jokingly.

She giggled a bit then opened the door. The entryway was a small room with a coat-stand and a shoe storage, from there we got to a large living room like area with a nice couch and a TV. Samantha directed me to a hallway on the left. 3-3 doors were on each side of the corridor.

"Last door on the right," Samantha instructed. "Can you put her to bed? I need to go take a leak or I'll piss myself right here right now."

"Sure, go ahead."

I somehow managed to get Emily onto her feet and open the door with one hand. Her room was cozy. A large bed in the corner, a wardrobe at the opposite wall with a dresser, a small office desk with a laptop sitting on it still turned on. I struggled her to bed and threw the covers over her.

"Waaeee," she said just as I was about to leave the room.

"What?" I asked not understanding what she wanted.

"Wateeerr!"

"Ohh right, I'll find you some water," I told her as I left.

I remembered that the first door on the left was opened and it was their kitchen so I started walking in that direction when something stopped me. The door next to the kitchen was opened slightly and I saw light coming out. Just as I passed the door I something caught my eyes that I'll never forget. It was Samantha peeing, standing up. I couldn't believe what I was looking at. She had a penis! I slowly backed away to the door of Emily's room not knowing what to think of this. Then the bathroom door opened and Samantha came out to the corridor.

"Ahh I really needed that! You alright? You look like you saw a ghost or something," she asked.

"Yes... I'm... I'm okay. Emily asked me to get her a glass of water. Where can I find the kitchen," god I was hoping she didn't saw me.

"It's right here," said as she led me to the room that I suspected to be the kitchen.

We got a big glass of water and put it on the nightstand in Emily's room then left her to sleep.

"Well Ms. Sleepyhead is in bed, you are home I guess my job here is done," I told Samantha in the living room. "I'll be leaving then. Thank you for tonight Samantha. It was very memorable that's for sure."

"The thanks are all mine. Without you I would still be out on the sidewalk somewhere. Oh, and call me Sam or Sammy," she told me with her face getting red. "So, thanks again," she said and kissed me on the cheeks.

"Good night!" I said my farewell as I felt my face getting red as a tomato.

Thoughts were racing in my mind all the way till I got home. I knew trans persons existed, but I had never thought i would meet one, or befriend one. And that small parting kiss she gave me. I couldn't get it out of my head. I was in confusion of the highest order. How can she be trans? I couldn't tell her apart from any biological girl. Needless to say, I couldn't sleep much that night.

A few days passed by and i was still thinking about Sam. Then around 3 days after the party it hit me. I was actually interested in her! By her reactions at the party and after at her place I think she liked me as well. I knew this was probably a chance I won't get another time in my life. I needed to go on a date with her.

I pulled out my phone and opened up my chat app. Sam gave me her contact when we were stumbling to her place. I opened up our empty message window and just stared at it for hours. Thinking what should i write. I poured myself a drink from the fridge and drank it in one go. Then from the liquid bravery I quickly wrote her a few lines:

G: +Hi Sam!

G: +It's Gary, from the party last week remember?

G: +I just wanna ask if you want to grab a coffee this week?

I quickly closed the app and tossed it in the drawer to prevent myself from overdoing it. It was getting late and I had to go to work next day so I took a shower and went to bed.

The next day I was already nervous when I first looked at my phone. But for my disappointment there was no new messages. She saw my text the app indicated it, but didn't write me back. "That's my luck," I thought to myself as I put my phone in my pocket and headed to work.

***** Extract from Sam's chat history *****

S: +OMG OMG OMG EMILY OMG HELPME!

E: +Calm down girl!

E: +Whats the panic?

S: +THEREWASTHISGUY AT THE PARTY ANDHEASKEDMEONADATE I THINK

E: +Can you drop the allcaps and slow down a bit?

S: +Sorry, so you remember the party last week?

E: +Parts of it yes, you know I blacked out and I woke up home

S: +There was this guy at the party we talked a lot and he helped me bring you home.

E: +I KNEW IT! There was something fishy about that night! I knew you couldn't possibly bring me home alone!

S: +I kinda kissed him as he left and he asked me out

E: +Wow! I'm dying of alcohol poisoning and you are smooching guys in the living room.

E: +Flatmate of the year award goes to....

S: +....

E: +what did he ask anyways?

S: +he asked me if I want to grab a coffee. Is this a date?

E: +idk ask him lol

E: +also, is he cute?

S: +omg yess he is.

S: +I can't just ask him if he ment it as a date!!!!!!!

E: +Why not? Be brave sis!

E: +Gotta go! Boss is here.

E: +wye

S: +bye

*****

The buzzing of my phone dislocated me from my work in the office. I took my phone and angrily looked at it.

"Who wants to disturb me in the middle of the day?" I murmured.

I looked at the lockscreen and saw that it was a message from Sam. I needed some time alone. I couldn't just read it in the open office, so I went to the restrooms to sit into one of the stalls. My hands were shaking as I pulled out my phone and unlocked it.

G: +I just wanna ask if you want to grab a coffee this week?

E: +Hi Gary!

E: +ofc i remember, that night is kinda hard to forget

E: +I'd love to grab a coffee

E: +ehmm you ment it like a...

E: +you know..

E: +date?

I took a deep breath and slowly exhaled as I started typing my answer:

G: +yes, i ment it date-like [blushed emoji]

G: +if you are up to it ofc

E: +OK than.

E: +I know a good place

I was so happy! I felt butterflies in my stomach and everything. We agreed to meet in front of her apartment building on Friday after work.

I spent the rest of the day floating in happiness and the rest of the week in excitement. I had never really thought about dating trans persons. I had no problem with them, but i just never saw it happening and now here I was. On Friday afternoon, getting dressed to go on a date with the most beautiful girl I ever seen and she was trans.

I arrived 5 minutes before the time we discussed to be on the safe side. After a couple of minutes, I saw her coming out of the building. She was looking even more beautiful in daytime light. She was happy and nervous at the same time I could tell just by looking at her.

"Hello Gary!" she greeted me from a good distance.

"Hi Sam!"

"You waited for long?"

"Nope, you were right on time. So where are we heading?" I asked curiously.

We took the bus for a couple of stops and got off right in front of a nice-looking café. It was not one of those wannabe, fast-food type of cafés but a traditional one. Not many of those are around these days so I was happy with her choice. We entered and she led me to one of the corner cubicles. We got in just in time because when I sat down, I saw that it was starting to rain outside.

"Welcome! What can I bring you today?" asked the waitress.

"I'll have aa...." I said trying to buy some time while still browsing the menu, "...aa hot chocolate."

"I would like a green tea with honey."

"Excellent choices! I'll be right back with your orders," said the waitress as she left.

"Kind of funny," noted Sam.

"What?"

"We are in a café and none of us is drinking coffee."

We giggled a bit on the situation and had some good conversations about various topics. She told me that she was working in a furniture store as a demo room designer, I told her about my job and so on. Even though we had a great time there was always some tension in the air from her side. I saw that she was nervous and that her heart was pound probably.

I saw her building up the courage and then she finally told me:

"Look Gary, I really like you but before we take this any further there is something that you really have to know," she took a deep breath indicated me to come closer. I leaned across the table.

"I'm trans," she said and her face turned extremely red instantly. "Please don't hate me," she added after a slight pause.

"No problem, I knew it already," I said her in a comforting tone.

"WHAT???"

"When we were at your apartment after the party, and I was looking for a glass of water to give to Emily. You went to the toilet and left the door slightly opened and I saw you."

She let out a small giggle with an annoyed expression on her face.

"I really have to have that door fixed. You can't close it and I normally hav... WAIT," she exclaimed suddenly. "You knew it all along? Since.. last Friday?"

"Yes," I confirmed, "I didn't want to tell you because I wanted you to tell me when you are ready."

"But that means... you really want to date me??" her face was full of disbelief.

"Yes, why do you think I'm her..." I couldn't finish the sentence because she pulled me into the deepest kiss that I ever got. Her tongue was flickering around in my mouth like a fish out of the water.

"Thank you," she said with tears running down her cheeks.

"I guess I kiss bad enough to make a girl cry."

She laughed and pulled me into another kiss. We were kissing there for quite some

time before letting go of one another. I sat next to her so we could talk easier in the noisy café.

"So, what made you ask me out?" Sam asked, resting her head on my left shoulder.

"I don't know, when I saw you at the party there was something in you that caught me," I replied. "I couldn't get you out of my head for days."

"That's cute, but don't you mind that I... you know.. have a pee-pee? I also intend to keep it."

"First I was concerned and confused but then I realized that I was interested in you and not what is under your clothes. We will work this out, I'm sure. So no, I don't mind. I accept you the way you are."

Then she pulled me yet into another deep kiss. The closing hour of the café was closing rapidly so we decided to call it a day. I walked her up to the apartment building where we had an intense snogging session.

"Want to have lunch tomorrow?" I asked.

"I would love to but I promised Emily that I will go shopping with her. How about Sunday?"

"Works for me, lets meet here at 11 am."

"Sounds good to me."

We exchanged a few more kisses and parted. Only when I got home and sat down at the side of my bed did I realize how horny I was. I had a nice day, had a date with a beautiful girl why not have some alone time, I thought to myself. So, I sat down at the computer, thinking what should I watch. I was thinking and excited about my Sunday date with Sam and that gave me an idea. I searched for some trans porn. I never watched anything like that and I was curious. I was surprised how much it turned me on. I was watching a video in which the guy was giving it to a girl from behind, then all of a sudden, they switched places and the girl was dicking down the guy hard and fast. That gave me in idea. Already close to cumming I applied some lube to one of my fingers and fearing how it will feel I touched my asshole with it. It was a ticklish but nice sensation. I started jerking my cock faster and at the same time applied some pressure to my hole and the finger just popped in. That was the moment that pushed me over the edge and I started cumming all over my stomach.

After I cleaned myself up, I was sitting on the side of the bed once more, contemplating what just happened. I was enjoying anal stimulation. It gave me a bit of a relief since Sam is trans and she might want to top me someday at least I will know that it is enjoyable. I went to sleep with a smile on my face.