Samantha Pt. 05

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

E: +so how is the weekend going?

S: [Sending file: MSDCF1098]

S: [Sending file: MSDCF1099]

S: [Sending file: MOV1007]

S: [Sending file: MOV1008]

S: +something like this ;-)

E: +JESUS!

E: +HOLY FUCK THATS HOT!

E: +omg!!! did it feel as good as it looks?

S: +no

S: +even better

E: +haha fuck you!

E: +im sitting in here all "dry" girl

E: +i need to get someone to give me a D like that asap

S: +dont worry. Im sure your dick is just lurking around the corner ;-)

E: +geez hope so. IDK how long can i hang on

E: +where is Gary? dont tell me he already left

S: +nah he is in the shower, cooling off a bit

E: +neat

E: +how about a girly-night tonigh? to celebrate you know.

S: +i thought you will be off for the weekend

E: +that was the plan but my mom had to step in at work

E: +and you know how my dad is acting all weird around me

E: +so i thought it would be better for me to go back

E: +im waiting for my train actually

S: +okay, have a safe trip

S: +see you tonight

E: +see ya!

*****

I washed my face with some water at the wash-basin in the bathroom. The water running on my cheeks felt cold and refreshing. I wiped myself off with a towel and checked myself in the mirror. "I haven't looked this relaxed in years, Sam is working wonders on me," I thought to myself as I put the towel back onto the rack.

As I entered her room I saw Sam putting her phone away with an annoyed expression on her face. I sat down on the bed next to her kissing her cheek.

"Everything alright?" I asked.

"Yes, it's just Emily asked me for an only girl night this evening. Do you mind if I go?"

"I don't mind at all! If you don't mind that I'll go for a boy's night with Dennis while you are off," I said.

"Then the deal is sealed," she said giggling. "How about a movie for the time being?"

"Sure, any suggestions?"

"Let's see what's on the playlist shall we?"

We spent the rest of the afternoon watching movies in the living room on the couch. In the meantime I arranged my things to meet with Dennis. I picked a place not far away from where Emily and Sam would be having their girl's night so that we can meet afterwards. The time passed quickly and the evening arrived, and so did Emily.

"Hi guys!" she greeted us from the door. "I'm home!"

"Hi, how was your trip?" asked Sam.

"It was alright, less crowded than a Sunday ride that's for sure. Hi Gary!" said Emily while giving me a strange measuring look.

"Shit, she knows," I thought to myself. "Hi!" I replied.

"So you two better get ready, we have to leave in 30 minutes to catch the bus," Emily instructed us.

We went to Sam's room and started getting dressed. It was faster for me since I only had a few shirts at her place that I left there at some sleepover. I was sitting on the side of her bed waiting for her to get ready when I saw her butt. She was searching for her jeans in the wardrobe and wore nothing but her nice, blue panties. I could not resist the temptation, so I walked over to her and planted a small kiss on her butt-cheek.

"Hey," she giggled, "stop it! We are already late."

"Sorry, I could not resist," I apologized. "Besides, walking around with a booty like that has some consequences you know."

After getting ready we took the bus that we almost missed and traveled a few stops until we reached the party-quarter of the city. Dennis and I picked a bar not far from the bus stop and the girls choose a different one a few corners away.

"So you two take care," I said as we parted our ways.

"Yeah, you too! And call me when you are done, we might be still around and we can take the bus together," replied Sam.

"See ya!" said Emily.

I gave a quick kiss to Sam before heading for the bar. As i turned around I saw that Dennis was standing a few meters behind me with the biggest grin on his face I ever saw. I walked over to him and we shook hands. We greeted each other and started walking towards the bar.

"So, was that who I think it was?" he asked after some time with a smile on his face.

"Yes, it was Sam," I replied.

"Damm, bro she is a real catch! Who was her friend by the way? That girl is hot!"

"Oh, that was Emily, her flat-mate," I explained.

"Come on, she isn't that flat," laughed Dennis.

"Haha, you know what I meant. They are having a girly-night a few minutes from here."

In the meantime we got into the bar and went straight for the bartender.

"Evening," he greeted us, "what can I get you?"

"So, first round is on me," I said to Dennis, "I'll take a jack-and-coke."

"A gin-tonic please," said Dennis after some thinking.

We took our drinks and sat down by the window. After clinking our glasses we took a deeps sip from our drinks and sank back to our seats.

"So tell, me everything," said Dennis. "How is she?"

"She is sweet and cute."

"Yeah I saw that, but come on man, give me some dirty details. How's she in bed, you told me there were some 'complications' or something."

"Oh, a gentlemen never tells," I said jokingly. "But to ease your curiosity, the main thing is that I was her first."

"No kidding, WAIT! What do you mean 'was'?"

"Shit," I laughed, "yes, we are over 'that' if that's what you are asking."

"Nice, congrats to you!"

"There is always another thing with her," I said taking a deep breath, "she is trans."

There was a brief moment of silence before Dennis burst out laughing, "Hahaha, man you have killing jokes. And I thought that you lost your sense of humor. Ahhh that was a good one."

I was trying to think of something to tell but then I saw his eyes widen and disbelief set in on his face, "JESUS! You are not joking!" he said.

"Nope, I'm not."

"That's a bit weird but okay, I guess."

"So you are okay with it?" I asked him.

"Yes, I mean I find it strange, but as long as you are happy," he said in a comforting tone.

"Thanks," I replied, "I thought that you will, I don't know, get mad or something."

"Pff... why would I? But I hope you know that you opened up a whole chamber of new questions for me."

"Haha I guess so," I replied, "ask away!"

"How did you find it out?"

"Well, I kind of caught a glimpse of her at the night of the party while she was on the toilet," I explained.

"Haha, you fucking peeper."

"Hey, it was not on purpose. I pretended that I did not see it and let her tell me when she wanted to. She told me like a few days later."

"That was actually pretty fair from both of you. But weren't you freaked out?"

"No... I mean yes, but no. I really just could not believe it at first, but I was not freaked out. I was in doubt about myself and everything, and needed some time to think things through. In the end, I decided to just go with it."

"Well if you put it that way, it's understandable. I'm not sure if I could be this cool with something like this. Especially if I knew it in advance," said Dennis.

We talked for long hours at the bar, about how he was doing, how were things at my workplace and so on. We downed a few more drink before decided that it was time for us to leave. We both felt the alcohol slowly kick in. We were not drunk, just slightly tipsy. Dennis called himself a cab and we went on our separate ways. I pulled out my phone as I started to walk in the direction of the bar that Sam and Emily was visiting.

I pulled out my phone and saw a few text messages from Sam.

S: +hows your night going?

S: +we are still here

S: +tell me when you want to leave

S: +xoxo

I checked the time, and saw that the messages came some 15 minutes ago. I texted here a quick, "on my way to you," then put my phone away. While walking towards the club, I was contemplating the things we talked about with Dennis. He did not freaked out, which I was thankful for. Also he said that Emily was hot. I was not sure, how he would react if he knew what I knew. On the other hand Emily could really use a boyfriend or at least a hook-up. Maybe it's worth a try. I imagined them going out and laughed at myself, "You are overthinking Gary."

I emptied my mind as I arrived at the bar and headed inside. The club was dimly lit by colorful neon lights, the air was full of chatter and music. I saw the girls sitting at one of the tables at the corner. Sam recognized me as well because she started waving at me. She was sitting there, with Emily resting her head on Sam's shoulder.

"There you are," said Sam as she pulled me into a kiss.

"How's the night going?" I asked.

"About as expected. Miss Drunkard here is in her usual state," she said pointing at Emily. "Alright, she probably not that drunk, mostly tired from the journey. How was your night?"

"It was alright, we had some catching up with Dennis. So you two ready to leave?"

"Yes I think so, come on Emily, it's time to go home."

"Hooooomeeee, home is nice," muttered Emily.

She was definitely not nearly as drunk as the first time we met, but she was not sober either. It was a pleasant change that she could walk on her own. As we were waiting for the bus we engaged in a conversation once again.

"So you did not drink at all?" I asked.

"I'm actually a bit tipsy but nothing special, I had a few cocktails."

"Yoooo and I'm druuuuuuunk," said Emily laughing.

"Haha we know," replied Sam, patting her on the back.

Emily sat down onto a bench and we were hugging with Sam waiting for the bus. She kissed me deeply then whispered into my ear, "How about you stay over tonight as well?"

"Gladly," I replied as I hugged her tighter.

The bus arrived and we got in the back. The ride to the girl's place was quiet and event-less. As soon as we got up to the apartment Emily headed straight for her room.

"I'll go and hit the hay, night you two!" she said closing the door behind her.

"Goodnight," said Sam.

"I'm taking a shower, care to join?" I asked Sam.

"Hmm.... that is an offer I cannot refuse."

As soon as we got in the shower we started making out intensely. Our kisses were deep and passionate while our hands kept exploring one another's bodies. Our soapy wet bodies were slipping on each other like crazy. Even the cold water could not cool down our passion. I took a handful of shower oil and started gently massaging it into Sam's body starting from her neck slowly working my way down to her belly and lower back.

I gently slid my left hand to her cock and my right hand to her ass and started moving my hands, massaging her butt and slowly working on her shaft at the same time. She was standing with her side towards me providing me with a great opportunity to kiss and softly bite her ear. Her dick was as hard as diamond and she moaned and panted slowly as I worked both sides of her. Her slippery cock danced in my hand wildly as I gently slid a finger between her cheeks and started circling her entrance.

"Ohh my," she moaned as she started to massage her own tits with her hands, "what are you doing?"

"Having some fun I guess," I said releasing her ear from my mouth and sucking on her neck.

"Well, Gary, you keep having fun like this a bit more and I will cum in your hands," said Sam biting her lower lip.

"Then, how about we take this to the bedroom?" I purposed.

"Love the sound of that, let's go."

We had hard time getting dry because we kept making out during the whole process. Once we were ready Sam peaked out onto the corridor to check if the path is clear and we quickly ran to her room. We jumped into her bed and started a heated kissing session immediately. We were rolling around in bed when we came to a stop and our lips parted. She laid on her left side, legs closed, with her dick pushed back between her thighs. She grabbed her right cheek and gently pulled it upwards revealing her beautiful pink asshole.

"So, what do you want to play with?" asked Sam in a seductive voice.

Without hesitation, I took her dick in my hand and started slowly jerking it while I licked my way from her balls to her hole. I started circling her asshole with small gentle licks, as my hand started moving faster and faster on her shaft. I felt myself getting hard just from eating her delicious ass.

"Hmm.. that feels nice," moaned Sam.

I slowly came to a sitting position removing my face from her booty and started to rub my rock hard cock on her balls gently poking her while working my hand on her dick at the same time. My actions were rewarded with soft moans.

"Put it in me please," said Sam, "I want it badly."

"Gladly," I replied.

I released her and got the lube from the nightstand, started gently massaging her entrance with it, slowly working my finger deeper and deeper into her hole until my finger was all the way in. "Aww heck a bit of teasing would not hurt," I thought to myself as I started gently massaging her sweet spot. I enjoyed her shivering and moaning as I slowly increased the pressure I applied with my finger. I could hear from her breathing that she was getting close but I did not want the fun to end just yet. I carefully removed my finger from her butt and rolled on a condom. I applied some extra lube onto her ass, and to my cock as well.

I put the tip of my cock to her entrance and started rubbing it around her hole. Slowly I began pushing her hole with my dick just very slightly, a bit forward, then back. I realized that her cock was leaking pre-cum so I took it in my hand and started gently jerking her with the residual lube on my palm as I probed her asshole.

After a while I decided that I teased her enough, I started to slowly applying more and more pressure with my dick until the tip popped into her hole. Her eyes opened wide and she let out a long, loud sigh.

"Ohhh god," she said in a sweet voice, "that's good."

"Really? And what if I do this?" I asked as I started slowly gyrating my hips while tightened my grip on her cock.

"FUCK YES!" she moaned loudly.

I liked how she enjoyed herself. Goosebumps all over her body, constant shivering and moaning, it made me feel like I am doing a great job. My right hand was slowly and steadily jerking her cock, while my left hand adventure to her breasts gently massaging her. This position with Sam laying in her side and me in semi-sitting position provided me an excellent view of her whole body. I could see all the little beautiful details of her body, it was like watching an angel.

I went on for quite a while gyrating my hips when I decided that time to move on so I started pushing deeper into her hole. She opened her mouth and eyes wide as I slowly pushed past her sweet spot all the way into her tight, warm, welcoming hole until I bottomed out.

Her tight ass firmly enclosing my thick cock as my balls were resting on her left cheek was a feeling out of this world. I let her adjust to the feeling for a bit before pulling back a few inches and then slowly pushing back full again. We went on like this for some time when Sam turned her head towards me, panting and said, "Could you that rotating thingy again?"

I felt that she was close to cumming so I complied, I pulled back my cock halfway into her hole and started gyrating my hips. Her breathing was getting heavy and erratic as I felt her cock becoming even harder in my hand. I knew she was on the verge of cumming so I increased the pace at which I was rotating my hips.

"Ahh Gary," moaned Sam, "I'm gonna.... I'm gonna... ohh FUCK!"

With that, her dick swell up, I felt her ass pulsate around my cock and finally she started to shoot ropes of thick, warm cum all over her thighs and the bed. I gradually slowed the movement of my hand on her dick until I came to complete stop. Her moans subsided and we locked eyes for a moment, she was smiling.

"Shit, that was awesome," she said, "did you came too?"

"Not yet, do you want me to pull out or something?"

"NO!" she said loudly. "Don't even think about it!"

She rolled onto her back carefully with my dick still inside her, now we were in missionary position. She grabbed my hair and pulled me in for a long and passionate kiss before I started to move again, slowly rocking back and forth. It wasn't long before I felt her moan into our kiss in pleasure again.

I increased the pace and length of my thrusts as I felt myself getting close. She must have sensed it, because I felt her flexing the muscles in her ass. A dirty trick for sure but it was more than enough to push me over the edge.

"Fuuck!" I groaned as I started cumming, emptying my load into the condom.

I collapsed on top of Sam tired and exhausted. As I was catching my breath something felt uncomfortable, as something was poking my stomach, something hard. I looked down and realized that it was her cock, she was rock hard again. Sam must have saw what I was looking at because she said, "Sorry, that was just too hot for me I guess."

I did not wanted to blue-ball her so I slowly made my way down, towards her cock. I saw her shiver as my own cock slipped out of her hole when I reached her dick. I wasted no time and wrapped my mouth around her cock instantly, sucking on it hard and bobbing my head up and down on her shaft. She ran a hand through my hair gently dictating the pace at which I moved my head.

The taste of her sweet-salty cum from her orgasm before was still lingering around on her cock driving me mad for her tasty juice. From her breathing I could tell that she was close already. I wanted her to cum in my mouth so badly! I was fondling her balls when I heard her moan loudly into the night, "I'm cumming!"

With that she forcefully pushed my head down on her shaft, forcing it into my throat. It surprised me a bit but I quickly accommodated. I felt her dick twitch in my throat as she shot load after load of thick cum directly into my throat. As her orgasm subsided and she released my head I sucked the remaining cum out of her shaft, kissing her on the tip before laying next to her in bed.

"Fuck, that was good," she said softly.

"I'm glad that you liked it," I replied.

We were both extremely exhausted and sleepy, so without any other word, I pulled the cover over us and cuddled Sam from behind.

"I love you Gary," she said.

"I love you too," I replied.

"Good night."

"Sweet dreams."

*****

I woke up to the feeling of something tickling my nose. Slowly opening my eyes I realized that it was Sam's hair. It was morning already, and we were still spooning. I realigned her hair and hugged her a bit tighter. The scent of her skin found its way into my nose and I loved every bit of it. It was so pure, full of life yet somehow soft and tender. It was driving me crazy for her.

I started caressing her under the blanket. As I was gently running my hand over her waist and her stomach I felt her morning wood poke my hand. I found it funny that she still didn't wake up. I softly enclosed her boner in my hand and started to move my hand. She let out a soft moan still in her sleep. I positioned my head behind hers and began giving her small soft kisses, starting from behind her ear gradually heading towards her neck. I was around her nape when she woke up, moaning softly.

"Hmm.... what are you doing?" she asked softly.

"Making sure that you have a good morning," I replied as I tightened my grip on her member.

"Ahhh that's a good start," she said playfully, "but two can play this game," and with that she started grinding her ass on my morning wood.

"What are you playing at?" I asked her.

"Hmm.... I have something on my mind. Where did we left off yesterday?"

She playfully rolled over onto her back pulling me on top of her. We started making out as our dicks touched each other pressed between our stomachs. She reached down took hold of our members and started moving her hand. We stopped kissing and when I looked into her eyes, she made an eye motion towards the nightstand. I knew what she wanted.