The New Hire

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

As you'd expect, we also began to get intimate, though we were deliberately taking it slow. We never had to talk about it - we just seemed to find a natural rhythm that worked for both of us.

After a few weeks of perfection, Sam and I had one of the most difficult conversations I can ever remember. After a small dinner out, we decided to head back to my apartment to watch a movie or play some games. Once we got there, the normally easy and light mood was suddenly tense and stifled.

"Brett, we need to talk," Sam said to me, a hint of fear in her voice.

"What's up?" I asked, as I could sense something was wrong.

"I trust you more than anyone and I'm really afraid that I'm falling hard for you," she said, continuing, "but, I need to share some things with you and I'm scared to death to do so." Tears began to well up in her eyes, and I immediately grew very concerned.

"Whatever it is, we can work through it Sam," I said softly, not fully knowing what I was about to get into.

"I don't know how else to say this, so I'm just going to ... uh ... I have a penis," Sam said, the words muttered through a voice trembling in fear.

"What?" was the only word that managed to find its way out of my mouth.

"Please don't hate me for not telling you sooner. I just ..." Sam trailed off, her body shaking and her wide eyes fully wet, staring at me for some sort of reply.

The truth is, I had no clue how to respond in that moment. I didn't feel blindsided as much as I was confused. To me, Sam was all woman, and an incredibly beautiful one at that. The idea of her having a penis wasn't repulsive or off-putting, it was just confusing. As the thoughts raced through my head, I finally realized that Sam was sitting in front of me a complete mess. In my delay to answer, she began crying in earnest, clearly shook up by my lack of a response. My emotions could wait - my closest friend was clearly in pain, and I couldn't let her stand there feeling alone.

I stood up and pulled her tightly to me. Her head buried into my chest and we stood there in a long hug that was silent and soothing. I never spoke a word, realizing I wasn't yet sure what to say. I knew I was straight, yet the bombshell of this news never made me question that. Samantha was all woman, even if she was not born a genetic one. In that moment, I said to her the only words that mattered.

"Sam, I love you."

She looked up at me with her soaked, beautiful green eyes. Her shaking had stopped as I held her close, and her eyes closed as she kissed me more passionately than she ever had before.

"I love you Brett. You're the best thing that's ever happened to me," she responded quietly, after our lips broke apart. I felt her body ease into my arms, as she was overwhelmed with comfort and peace.

We sat down together on the couch and I learned so much more about Samantha. She told me about her parents, and how her desire to be a girl as a child caused a rift between them. Her dad hated that his only son was "gay" and "screwed up in the head" while her mom was completely accepting. They divorced when Sam was only 10, and she and her mom moved in with her Aunt. Her mom worked two jobs to help pay for the hormones that would make Samantha more fully a girl. Sam hadn't talked to her father since the divorce, and had no intentions of doing so. She still talks to her mom all the time, and couldn't wait for me to meet her.

Her shy nature became clear as she shared the stories of abusive boyfriends from her past. Sam had made the mistake of thinking guys would be ok with her physical differences, only to find out a few times that the backlash could often be severe. She was even put into the hospital by one particularly insecure boy, who subsequently concussed her and broke several of her ribs in the process. I told her I wanted to find that guy and end his life, which she briefly contemplated for a second before thinking better of it. As it turned out, he was only one of several who physically struck her when they found out the truth about her. I found myself in tears as she recounted the stories, and how they made her withdraw from the world, only to believe that she would end up alone in this life.

Sam shared with me that she hadn't yet thought about having the final surgery, but the thought had crossed her mind ONLY because of the difficulty in getting close to guys. As she saw it, she was no less a woman by having a penis than those who were born with a vagina. Knowing her like I did, I agreed completely.

For endless hours we talked about her past. She shared her deepest fears with me. She told me that the ratty tennis shoes she always wore were a gift from her first boyfriend, who was the only one who wasn't a jerk to her when he found out the truth. The more I learned about her, the more my heart was enveloped by her. Any doubts about being with a transgendered girl were easily wiped away that night. I realized I was too far gone. I was deeply in love with this girl, and nothing was going to change that.

Passion

------

Before the revelation, Sam and I had already planned a short vacation together to Florida. Since it was October, the temperatures in Florida would still be perfect for spending time on the beach, and we were looking forward to the time away from work. Deep down, I think we both felt like this would be the natural time for our relationship to take the next step. If I'm being honest, I was a little nervous about it, but still anticipated it nonetheless.

On a Thursday afternoon, we made the long drive down to Destin. We were able to get a small condo directly on the beach. After an amazing evening and retreating to our separate bedrooms, we agreed to spend the next day entirely on the beach. On Friday morning, I saw Sam in a whole new light.

She came out of the bathroom wearing a stunning, light pink, two piece bikini. In our time together, I knew that Samantha had a nice pair of breasts, but I had never seen them like this before. Her cleavage was sizable, and her mounds looked perfectly round and perky. I was no expert on the matter, but they appeared to be around a C-cup, which seems irrelevant in how perfect they looked on her fit, smooth frame.

Her hips jutted out from her thin, trim waist. Her belly button glistened and begged to be kissed. Her whole body just seemed to have a soft, beautiful glimmer to it. She looked every bit like a super model, and I sat there stunned, wondering how I was so lucky to have this beautiful angel in my life.

"My god, you are so gorgeous," I told her, which made her blush intensely.

On hearing the words, she bit her lower lip and slightly turned her head to the side. That slight movement was so incredibly sexy, I almost lost myself right there.

"You're not so bad yourself, mister," she said back to me.

I was no stud, but I did work hard to keep myself in good shape. I was certainly not in her league, however.

Sam walked over to where I was sitting on the couch and sat on my legs, facing me. She placed her lips on mind and we kissed passionately, losing time as our tongues wrestled with one another. My hands moved all over her soft skin, as hers did on mine. I was having a hard time resisting her, and the anticipation of being with her was starting to drive me mad. Before things got out of hand, she pulled away and said, "Now let's get out to the beach before I end up naked."

I'll be honest - the beach sounded like a terrible option in that moment.

We exited the condo, making our way onto the nearly empty beach below. We walked up and down the beach, enjoying our time with one another. The weather was ideal, the breeze soft and cooling, and the feeling of her hand in mine was perfect. We alternated walking in the cool water and the hardened sand, taking in the scenery and pausing periodically to kiss and embrace. It was a perfect day.

After a long day on the beach, we finally decided to make our way back to the condo.

As we got into the condo, and let the door close behind us, Samantha pulled on my hand, drawing me in for a long, passionate kiss. I lifted her up and her toned, firm legs wrapped behind my back. My manhood was growing stiff very quickly, and Sam could feel it press against her leg.

"Brett, I want you so bad," she said to me, sounding anxious and sultry. The words melted me.

I looked in her eyes and knew that the moment had finally arrived.

I walked our entangled bodies into her bedroom, where we continued to kiss intensely. As our lips broke free, I went to kissing up and down her neck, kissing passionately in the space between her clavicle and neck. She sighed "Mmmmmmmm" with every kiss, her pounding heart apparent to me as we drew closer and closer.

"I've never been with anyone before, Brett. I'm not sure how this is going to go," Sam said to me, a tinge of nervousness in her voice.

"I love you Sam," was all I could think to say, my mind numb from passion.

Sam's legs unwrapped from around me and she stood on her own, taking one step away from me. She reached around the back of her neck, untying the bikini top. She slowly pulled the thin straps down, revealing her perfect, tear drop shaped mounds. Her nipples were light pink and erect, with half-dollar sized areolas that were light pink and perfectly shaped. She reached around her back to take the top off completely, and her breasts swung gently from the light movements, arousing me even further. The bikini top fell to the floor and her breasts burst forth in front of me, bouncing ever so slightly once set free from the cloth below.

"Wow. Your breasts are perfect, Sam," I said, nearly drooling in front of her. My cock rapidly stiffened in my swim trunks at the sight of her perfectly formed chest.

Sam walked over, putting her fingers into the front of my swim trunks. She reached inside of them, lightly touching the head of my cock with her fingers. She looked up at me with eyes that asked, "Can I take them off?" I nodded quietly, and she began pulling my trunks off, my rigid 7 inch cock springing upward as they were pulled to the floor.

"Oh Brett!" Sam exclaimed, drawing a large smile to my face.

Before I could say anything, she had placed her lips gently around the head of my shaft. The sensation was incredible, making my sack tense up from the pleasure. She gently grabbed my cock with one hand, while her other rested on my leg for balance. Sam began taking more of my cock into her mouth, her tongue swirling all around the shaft, intensifying the sensation incredibly. She pulled off of me a few times to kiss the shaft and lick it attentively, which made me moan in intense pleasure. For a few minutes, she stayed there on her knees, bobbing her mouth on and off my cock, driving me insane.

Sam finally stood up from her position on the floor, placing her hands behind my neck. "Are you ready to see all of me?" she asked in a tone that was both sexual and nervous.

"I want all of you Sam," I responded.

She took a step back, shifting her delicious hips left and right as she shimmied her bikini panties to the floor. Between her legs were several strips of some sort of flesh tape. Her hands were shaking as she reached between her legs and quickly stripped the tape off, which looked painful.

As I looked on, I saw her womanhood appear suddenly before me. It was hairless and soft, with a light pink head. I had never seen another cock in person, but hers was unlike mine. It was beautiful and completely feminine in its appearance. As she stood there, completely naked before me, I realized she was 100% woman, penis or not.

"Sam, you are so incredibly beautiful. Every last inch of you," I said to her, as she stood there with a nervous energy to her.

On hearing the words, she smiled deeply and I noticed that her womanhood began to stiffen as well. In that moment, I wanted nothing more than to pleasure her, the woman I loved. I grabbed her hand, laying her in the bed. I laid on the bed next to her, my head and legs on the opposite of hers.

I gently grabbed her cock, which was as soft and smooth as it looked, and placed the head between my lips. I could taste her sex on my tongue, and it aroused me further, knowing she desired me in that moment. At the same time, I could feel her hand grab my hardened shaft and place her mouth around my shaft.

I began placing her more and more into my mouth, swirling my tongue around her shaft in the same way she did for me. Her body shuddered in my hands.

"Oh shit, oh my god that feels so good, Brett," Sam cooed, taking her head off of my shaft briefly.

We laid there, continuing to pleasure one another softly. My shaft in her mouth, hers in mind. I could sense the sex in us building up intensely, driving us closer and closer to eruption. I was often frozen in my actions as her lips and tongue moved all around my cock. I could tell when my same actions had triggered sexual pleasure in her, as she would moan deeply and freeze in place as well.

After a few minutes of pleasuring one another intently, Sam stopped. "I want you inside me," Sam said to me, pushing slightly away from me, taking me away from my inevitable climax.

"Are you sure you're ready?" I asked her, no longer nervous about what lay ahead.

"I want you so much right now. I want you to fuck me Brett," she said in a strong, sexually charged voice.

With that, she grabbed a bottle of lube she had resting on the nightstand and tossed it at me. She repositioned herself on the bed and spread her legs, her rigid 6" cock pointing towards her perfect breasts as she laid her head on the pillow. The sight of her was thrilling.

I took the bottle and squirted the cold lube into my hand, spreading it over my painfully stiff erection. I moved over to Sam, placing my finger on her pink, star-shaped hole, lubricating it ever so softly. The feel of my fingers on her body made her body quiver and I saw her cock twitch as she moaned out "mmmmmmmm" with her eyes pinched tightly closed.

I moved over to the space between Sam's beautiful, toned legs. I grabbed her hips with my hands and drew us closer together. Our erect cocks collided gently, which sent a shiver up my spine. The anticipation of being inside of her had driven me to a painfully stiffened erection.

"I'm ready," Sam said, her body somewhat tense and her eyes opened and locked with mine.

I leaned into her, my face now even with hers and placed a passionate kiss on her lips. I moved my lips down her body, latching them onto her beautiful, erect nipples. I sucked on them strongly, whipping my tongue back and forth over them, massaging her considerable flesh in my hands.

"Ohhhhhhhh Brett, that feels so good," Sam cooed as I massaged and sucked on her mounds. Her skin smelled like the most expensive fragrance, and her skin tasted like the sweetest nectar.

After a minute, I reluctantly pulled away, grasping my slick cock in my hand. I began moving the head of my shaft towards her pink, tight hole. I pressed gently against it. Sam's body clenched up slightly. Slowly, I moved my head back and forth against the tight hole, pushing ever so slightly against it. My cock began to slip inside of her when she cried out, "Ohhhh. Hold on, hold on."

The head of my shaft was fully inside her incredibly tight hole. I could tell she was in pain as I said to Sam, "Do you want me to stop?"

"Hell no! Just go slowly, I'll be ok," she responded passionately, wincing ever so slightly.

I began pushing slowly as she moaned aloud. Within a minute, my cock was fully inside of her. I stopped there, our bodies intertwined to perfection. She wrapped her legs around me, pulling me in closer. I leaned in and our tongues found one another, my hand massaging her breasts as my cock throbbed inside her tight, perfect body.

"The pain isn't as bad now. Just stay like this right now. I want to remember you deep inside of me," Sam said through a lightly panting breath. I took advantage of the pause, kissing her neck again and paying special attention to her perfect breasts and perky nipples. Her body quivered underneath me, as she moaned approvingly.

After a brief moment, she locked eyes with me and whispered, "Fuck me."

I slowly began to withdraw my shaft from inside her, which caused her to moan "uhhhhhhh" in pleasure. She was so incredibly tight, but I could feel her body begin to relax. Again, I pushed into her, my hips rocking forward. The motion made her breasts sway up and down while her rigid cock bounced into her body. The sight of her trim, fit body moving in motion with mine drove me closer to climax.

In and out of her I thrusted and her pronouncements of pleasure grew more and more intense.

"Oh Brett! Oh god, fuck me. That feels so amazing. Oh god!"

The more and more I moved in and out, the more her pleasure heightened alongside mine. Before long, my thrusts were rhythmic, as her pain disappeared into extreme sexual pleasure. As I was thrusting my cock deep inside of her, I took her own stiffened cock in my hand and stroked her gently as well. Faster and faster I thrusted my shaft deep insider her, as my hand stroked up and down her perfect, soft, smooth cock as well.

"Holy shit...oh god Brett, I can feel myself ... oh god," Sarah muttered, almost unable to contain herself. Her body began tensing up; I could sense she was about to hit her orgasm.

My balls began to tense as I could feel my body fill to its explosive climax. After a few more thrusts, I rammed my cock deep inside of Samantha. My shaft rapidly filled with my seed and began to convulse inside of her, rocketing my warm milky cum inside her tight, perfect body. I nearly passed out from the intensity of the release, the sensation almost overwhelming. Twitch after twitch my cock erupted, releasing my thick, milky cum into her for what seemed like a small eternity. My body felt completely engulfed in warmth and sexual pleasure, as every inch of my skin tingled during the release.

Sam's back was arched back as her body began to lock up and convulse as well. I removed my hand from her cock, which quickly filled and erupted, shooting rope after rope of her sticky white cum onto her flat belly and jiggling chest. The explosive sexual release from Sam caused her to close her eyes as she bit her lower lip and let out a long and pronounced "shittttttttttttttt." With each rope she shot, her beautiful female cock rocked up and down, until she was completely spent, her skin glistening with sweat.

For a moment, I stayed there - deep inside her - and stared at the perfection below me. Sam was sweating and breathing heavy but had the deepest, warmest smile on her face. Her body was no longer shaking. She had lifted her hands up to her breasts and began moving them in a massaging motion, which was erotic and nearly drove me to sexual hunger yet again. My cock was still stiff and deeply buried inside of her, making me feel completely at one with this amazing creature.

"That was ... oh my god, Brett. It was more than I could have dreamed of," she purred at me, looking up at me with those beautiful green eyes.

She reached for me, and I drew our heads close together. We locked lips and kissed passionately, our tongues finding one another yet again between our interconnected mouths. My hand drifted up to her breast and had begun kneading the soft, smooth flesh.

"That was so amazing," I replied back after our lips parted for breath.

I eventually withdrew my still erect cock from inside of her and moved to lay beside her in the bed. She turned to face me, and our cocks met and lightly intertwined between our glistening bodies. Her breasts rolled over in front of me, and looked even bigger as they pressed against my body.

"I love you so much Brett," Sam said, staring into my eyes, her own lightly filled with tears.