“The Internship”, Chapter 9 – Work Trip
434 0 5
X
Reading Options
Font Size
A- 15px A+
Width
Reset
X
Table of Contents
Loading... please wait.

If I had anticipated going to sleep immediately after my date, I was mistaken. Chloe and Veronica ambushed me almost as soon as I had crossed the threshold, demanding immediate details.

If you thought my account above was too in-depth, well, that was nothing compared to the minutiae that my friends demanded. No detail was too unimportant to discuss, from his expression when he first saw me, to what he ordered at the restaurant, to his exact words during dessert. They sighed when I talked about the bench in the community garden, and they squealed when I told them about the note on the door.

“And we spent some time at his place, then he walked me across the hall. And here we are.”

“Oh, no,” said Chloe. “You are not going to gloss that over. What happened?”

“Well, I sat on his couch and asked him for a glass of water.”

“Yeah?”

“And he brought it to me.”

“Yeah?”

“And then he was awkward for a bit.”

Giggles. “Yeah?”

Oh, all right. “And then I said fuck it, if he wasn’t going to make the first move, I would. And I’ll tell you what...”. They both leaned in close. “I never did get around to drinking that glass of water.”

I didn’t share all of the details with them, of course, but by the time I retired to my bedroom, they knew that we had done an indeterminate amount of “fooling around” without actually consumating, as it were. At one point, Chloe held up her hands about five inches apart and made a questioning sound. I adjusted them a couple inches wider, gave her a thumbs up and a wink, and there the matter rested.

It was difficult, over the next couple of weeks, to get much in the way of alone time with Lamar. For one thing, we had decided not to reveal our relationship at work, in case they frowned on fraternization. To be honest we probably didn’t fool anyone, especially since no one needs to go to the copy room that much, but aside from having to fix my makeup half a dozen times a day, there were no real consequences.

In the evenings, we still spent a lot of time together, but it was with the rest of the group. They all knew, of course, and being a couple in a group of friends was actually a lot of fun. When we settled in for a movie, they let us have an end of the couch to ourselves. We played games and cooked and ate and laughed and generally enjoyed being together.

At some point, generally late in the evening, we would head to my room or to his, generally in whichever apartment everyone was not hanging out. It wasn’t that I was shy about them knowing what we were doing, but I still wanted to preserve a bit of mystery. We made out a lot, and I gradually gained a level of comfort in being fully naked around him. Once I did, I actually kind of preferred it. I kept finding him watching me, even if I was just reading or doing nothing at all. I loved the way he watched me.

And yet, we still had not slept together, not in the figurative or the literal sense. I went down on him a lot, and he returned the favor — an experience that will forever color the way I think about the phrase “eating out.” During this time, I got to know my own body in a new way, and I like to think I taught him a thing or two about his.

My initial anxiety about my sexual orientation was swept away very quickly. My body had been female for weeks at that point, but it was during this period that I started to become a woman. It happened gradually, of course. I got used to being referred to using the feminine pronoun. I no longer had to check the app as often to choose an outfit. The way I talked to my friends and coworkers, the way I interacted with the world, became more and more unselfconsciously feminine.

My body had started to feel normal too. At first, I would get such an intense feeling of strangeness every time I had to pee, or every time my arm would brush against a breast. The intrusive thought would come every time, “this is different, this is weird, what is this even?” But no longer. At one point, I realized that I had gone through an entire day, from waking up to going to work to coming home, without once having been reminded that I used to be a man.

When I was nineteen, my brother decided it was time that I learned how to drive stick shift. Before, I had only driven an automatic transmission. So one day, he came to my house in the middle of the night, dropped off his old Volkswagen Jetta, and stole my Ford Focus. If I wanted to go anywhere that summer, it would have to be on a manual.

It was the same sort of thing. At first, every motion felt foreign, and things that used to be easy were suddenly hard. My mental conditioning had actually skipped most of this step, and for that I was thankful.

But even after I had the skill in driving, it kept feeling weird. I was acutely conscious every time I got behind the wheel that I was driving stick. It just hovered there, always at the surface between my conscious and unconscious mind.

And then, suddenly, it wasn’t. Driving was just driving, and the fact that there was an extra pedal and a gear shift was just part of what it meant to drive. And the same thing happened with womanhood. All of the strange, new things that I had to do, the new sensations and new behaviors, became part of what was normal.

What’s more, my time as a man felt increasingly distant. When recalling memories from my past, I sometimes pictured myself at those times as a woman, not as a man. I could now start a sentence with “When I was a little girl...” without having the conditioning change it for me. I was me, and me was she.

Nowhere was that more apparent than in my relationship with Lamar. He was now my boyfriend, and that meant I was his girlfriend. I had never been a girlfriend before, but I found myself acting like the stereotypical girlfriend. I was floating around on a cloud of new relationship happiness, and it was the greatest feeling in the world to be able to share that time with my friends. Within the next two weeks, Chloe had started dating Chris, and Veronica was going out with Dave. We were actually quite lucky to have paired off so naturally, and without any of the tedious triangles that could have arisen.

And still Lamar and I did not go all the way. I knew I was waiting for something, something special. And then I found it.

Our first work trip, a conference in Boston, was starting on Monday. We would fly out on Sunday to set up, and spend the week working the conference floor, returning on Friday. Only four of us were going: Veronica, Dave, Lamar, and myself.

We were expected to share hotel rooms, and on paper I was staying with Veronica, and Lamar was staying with Dave. By mutual assent, we decided to pair off a bit differently. Five nights together, in privacy, in a decent sized bed. If there was every going to be a time, this was it.

Sunday night came and went without any hanky lanky, unfortunately. We arrived late, and still had to help set up the booth. By the time we all got back to our rooms, we were exhausted. The room had two queen beds, and for the first time we shared our sleep with each other. I kept my panties on, and he left on his boxers, but we were otherwise nude. The feeling of my breasts pressed against his side as we cuddled to sleep was pretty much sensational.

I decided Monday morning that no matter what, we would do it that evening. It was a type of power I had never wielded before, the keys to the kingdom of sex. The door had been closed long enough, though. I was ready to move forward.

I won’t bore you with the details of work that day. We represented the company like the Young Professionals we were, cordially greeting visitors to the booth and directing them to the appropriate place. My feet were truly killing me by the end of the day, but as I reflected, I wouldn’t be spending much time on them tonight.

Dinner was quick, and I ate less than usual. Part of it was nerves, but I didn’t want to be overfull either. Lamar kept looking at his watch, and we excused ourselves from our colleagues as soon as politeness allowed, and about five minutes apart.

How different that night from our first, tentative foreplay! Lamar had volunteered to leave the table second, so that gave me a short window of opportunity. I ran up to our room, stripped off my work clothes, and dived into my luggage for the special outfit I had brought.

It was black, like the dress on our first date, but there the resemblance ended. It was made of silk, with tiny straps up my shoulders. The top barely hung on, clinging to my curves and ending just around my waist. The matching panties were scarcely there at all. Over all of this, I put a silk robe in a soft pink, the same color as the rose he gave me on our first date. It ended around mid thigh, and tied in front with a thin silk cord.

I posed myself on the bed, with the robe and nightie hiding everything while promising everything as well. I had been too efficient — I had to wait ages, or maybe two full minutes, before I heard the key card in the lock. Lamar’s grin when he saw me rewarded all of the effort.

I stood from the bed and slowly walked up to him. I may have exaggerated the motion of my hips and I did so. Lamar’s eyes went up and down, slowly taking me in. I reached up languorously and draped my arm around his neck, felt him take my waist. I leaned up to whisper into his ear. “I want you.”

It was like I had blown up a dam. He began to kiss me with such abandon that I was afraid for a moment that we might fall over. I was overcome. I found myself subjected to a force that frightened me, at least a little. Suddenly I was very aware that he was large, and I was small; he was strong, and I was weak. If he wanted me, he could take me.

Well, I was giving, and that meant I wanted him to take. I surrendered myself to the avalanche. Before I knew what was happening, he had backed me up against the bed. A quick tug undid my robe, showing the silk underneath. No longer were his hands negotiating where they touched. They touched wherever they wished, to grasp the flesh of my ass under the panties, to seize a breast from beneath the nightie.

It was so much, so fast, but my own arousal had no problem keeping pace. I was wet, yes, but more than that I felt a void inside that I wanted him to fill. He stripped off my robe, let it spill to the floor. My nightie was next, and the panties. I was fully nude before him. He was still dressed, and the discrepancy was another symbol of the power he had over me.

He did not stay dressed for very long. He divested himself of his clothes in record time, and now naked himself, his erect penis perpendicular and ready, he pushed my shoulders back onto the bed.

I rode the motion, scooting back to give him room to follow me. Whether through conditioned skills or pure bodily instinct I don’t know, but as I moved back I spread my legs. I could smell myself, wet and ready.

He positioned himself on his knees between my legs. With one hand, he directed the head of his penis. He teased it against my labia, and I felt the void grow within me. I was hungry for it, and I was done with waiting. “Fuck me,” I said. “Oh, please, put it in me. Fuck me, please!”

I felt a pressure a little lower down, right at the entrance to my vagina. The pressure grew, and suddenly his penis felt absolutely massive. Was he going to fit? Would he tear me open instead? I felt a brief flash of pain as he pushed himself in. He withdrew slightly, and the pain was gone. He pressed again, and this time I felt only the pressure, the wonderful maddening pressure. Another stroke, another, and he was fully inside me.

If you have not experienced the sensation of a penis inside you, well, first off I’m sorry. You’re really missing out. Second, it’s not the easiest thing to describe, but I will do my level best.

I discovered that I had muscles down there, muscles that did very little without something to grip. Now they had it, and it felt amazing to use them to squeeze around him. Most of the sensation was on the surface, not deep within me, but I definitely got this feeling of fullness, of presence, of penetration.

As his pace increased, the force of his thrusts did as well. He was slamming his hips into my crotch, which sounds like it should have been painful. I suppose in a way it was, but gloriously painful, like stretching a sore muscle. He was battering me, and the force of it thrilled me to the core.

I wrapped my legs around him, shifted my hips to allow him to go deeper. I gripped the bed on either side, as if the room had turned upside down and I was trying not to tumble into the sky. My breasts did a dance of their own, gyrating wildly. In a sense that was uncomfortable too, but at the same time I cherished it. It was a sign that my body was his, that he could do what he wanted with me. I offered it all up to him.

I felt his pace change, a sort of frenzied final energy, and I knew what was about to happen. He arched his back, and I felt him spasm within me. There was a rush of warmth, and I knew that he had come.

He stroked a few more times, and then collapsed in a heap atop me. We lay there panting for a while. I felt raw and pummeled and sore, but somehow tremendously fulfilled.

After a minute or so, he lost his erection enough to slip out of me, and he rolled off to the side. His head nestled in the crook of my arm, his hand stroking up to gently cup one of my breasts.

“That was...,” he began.

“Damn right it was.”

“I mean....” The words trailed off.

“You said it.”

He drew in a deep breath, let it out slowly. “So did you...?”

“Not this time.”

“Oh.” He sounded quite disappointment. “Is there something I could do?”

I shook my head. “I don’t have to orgasm every time. It’s not about that.” I had heard women say that before, and always assumed they were just trying to protect my feelings. Now that I had experienced the other side, I discovered that it was entirely true.

As a man, the two feelings were connected. I would orgasm, peak, and then the contentment and relaxation, the satisfaction, they were all on the other side. But my female orgasms were different. They were amazing, a sensation unlike any I had experienced before, but they never quite pushed through into that fully satisfied place.

This time, I had not orgasmed, but instead had received a good deep fucking. And in that, I found the satisfaction. Perhaps this was why women liked to orgasm first. First the heights of pleasure, and then the contentment.

We slept together that night, and it was really nice. He had such a warm and firm presence in the bed, so that I continually knew and felt that he was there, even after I rolled over to my side. In the morning, I watched him get up and pad across the room, unclothed, and felt a warmth inside that had nothing to do with arousal.

Looking back, I like to think that he felt the same way about me. Perhaps it wasn’t love in the truest sense, the sort of eternal, die for each other type that movies always show cropping up in a mere week. But it might have been the beginning of that, and as the next few weeks went on, it only deepened.

We treated sex like a new toy that showed up on Christmas morning, that we couldn’t get our hands off of. The rest of the trip was a blur of work and intercourse. We got to where we would duck away at lunch, or on breaks, to furiously copulate back in our room, which was conveniently located in the same hotel as the convention. Our friends covered for us, or else we likely would have been fired.

My conditioned skills were well up to the task. I learned that I could effectively engage in several different positions. I discovered the wild joyous abandon of riding a cock, impaling myself on my partner and giving myself over to penetration. I experienced what it was like to be taken from behind, kneeling and standing, to watch myself in a mirror as a man thrust himself into me. As a man, I had always enjoyed watching doggystyle porn for the sight of the woman’s tits flopping around. As a woman, I came to understand that the sensation was not particularly pleasant. But it was still satisfying, an outward sign that I drove this normally mild-mannered man to such extremes of arousal that he did not restrain himself. I communicated this to him once during the throes of coitus by moaning, “Fuck me ‘til my tits bounce!” Judging by his reaction, I’m fairly certain he got the message.

Once the trip was over, our pace only diminished slightly. We had no way to fuck during the day at work, but we made up for it in the evenings. We did our best in the tiny twin beds, alternating apartments so that we did not wear out the welcome of our roommates. When I got my period a few weeks later, I switched to more manual and oral stimulation, and once it was over, Lamar returned the favor several times over.

Only total sexual exhaustion slowed us at all. Finally, when I was perineally bruised so that I could hardly walk, and Lamar’s erection was like a soldier trying in vain to stand at attention at the end of a week-long battle, we spent a night without any intercourse of any kind. That broke the spell a bit, and for the remainder of the summer, we restricted ourselves to a few days a week.

The end of the summer was coming. I had seen the signs on the highway, 2 miles, 1 mile, half a mile, 1,000 feet. But I had not slowed down or changed lanes. Would I exit in time? Did I even want to?

5