“The Internship”, Chapter 8 – The Date
376 0 7
X
Reading Options
Font Size
A- 15px A+
Width
Reset
X
Table of Contents
Loading... please wait.

And just like that, we became friends with Veronica. It is amazing to me how quickly every interaction I ever had with her became reinterpreted in light of the new information we had gained. She wasn’t being brusque or haughty; she was too shy to meet new people. Chloe and I were the pretty, popular girls that had tormented her all her life, as far as she was concerned. Our overtures of friendship were just the fake niceness that was on the surface, and she didn’t want to get caught like that again. When she interrupted us at work, that was the moment that her reluctance to speak up finally gave way to courage, and she managed to get out what she was trying to say.

As for the way the men treated her, that was more about her looks than about her. Of course she was flattered by the attention — shocked was more like it. She didn’t know what to do with it all. She apologized to me at least a dozen times about the thing with Lamar, but after we had split two full bottles of confession wine, I was more inclined to think it was funny than anything else.

Another side effect was that I had decided to stay in the program. Suddenly, all of my fears and worries seemed insubstantial. So what if I had tits? I was still me. And sure, kissing dudes was never something I was into, but turns out, I liked it now. What’s more, I was pretty sure that I didn’t have any interest in girls anymore. Why not try it out for a few weeks, consequence-free?

I should have remembered the stereotype, that women weren’t good at casual dalliance. Turns out, I certainly wasn’t. But that’s getting ahead of the story.

The three of us showed up late to work on Monday, but since our boss was even later, it didn’t matter one little bit. Lamar was totally on edge when I got there, and looked like he was about to burst when I asked if we could talk, but after ten minutes in the copy room, we made up. I apologized, he apologized, and we made plans to go out for dinner as a group that night. I was just about to leave the copy room when he called me back in.

“Maybe on Friday we could go for dinner, but like, just the two of us?”

He looked so hopeful, so anxious, and so damn cute that I left him on the hook longer than I meant to. “Sure,” I said, keeping my voice level. “I’ve got just the outfit.”

It was the longest week of my life. Oh, we all had a blast. Now that Veronica was part of the gang, all six of us spent pretty much every evening together. In the guys’ apartment, we had a six-player game of Settlers of Catan going, and we’d spend an hour or two every night advancing a turn or two, but mainly making stupid jokes about trading wood for sheep. On Wednesday night we went to a bar and listened to a band, and Thursday we went back to the same bar and just hung out. I was getting to know Lamar better, finding out about his family (two younger sisters), his hobbies (hiking, mountain climbing, and wood carving), and his interests (19th century fiction, hot peppers, classic Beatles).

What was more, I was finally starting to understand what a girl might see in a guy. The attractions of a woman were something I understood innately, growing up. But I never knew what a girl could possibly see in me, and come to think of it, that might have had a bit of a negative impact on my confidence in dating. I would see these awesome women going out with the shittiest guys sometimes, and I always wondered, what does she see in him?

Well, luckily Lamar wasn’t shitty. At least, I didn’t think he was, and Chloe and Veronica both agreed. (Spoiler alert - turns out, he was actually a genuinely guy. Well, almost. But that’s getting ahead of the story.)

I allowed myself to start appreciating the physical things. I think that impostor feeling was holding me back before, but now I had two real women who told me that I was a real woman too, and that was enough to convince me of what my anatomy could not. I allowed myself to look at his eyes, which were a piercing blue, and his smile, which would burst onto his face with no warning like a spotlight swiveling toward me.

His shoulders were broad, and he was tall. Weird to think that someone being taller than me would be attractive, but I found that I liked looking up at him. He had nice hands, too. And yes, I checked out his butt from time to time, and found nothing wrong with it. Nothing at all. Nosiree.

But there was more than the physical. I loved his passion when he talked about things he liked, but also his willingness to share that passion with me. He had a way of paying attention to me that blocked out the rest of the world. He would ask questions that let me know he was listening, and bring up things that I said days later when I had already forgotten them.

I think what really reeled me in was his ability to be silly, and not care. It wasn’t that he lacked dignity. He just never looked embarassed when we teased him. He would quirk that smile as if to say that his behavior was dignified by the fact that he did it, and he had no reason to be ashamed. It was confidence, and yet that confidence would sometimes desert him when he talked to me. I knew that I could hurt him, could shatter that confidence and wound him deeply. And because I knew I could, I did everything I could not to.

At this point, you’re probably reading this thinking, “So, you’re falling in love, then.” Well, yeah. But I didn’t know that at the time. I think you have to have been in love before to recognize the symptoms, and even then you’re so caught up in the moment that it’s hard to see the truth objectively. Throw into the mix that this is the first time I had felt that kind of love, that of a woman for a man, and you won’t be too shocked that I missed it.

Friday did eventually come, and my two roommates and I flew home to get me ready. Veronica, it turned out, was a wizard with hair, and had offered to put mine up. Chloe went through my jewelry and declared that I needed something fancier, so she went through her own collection for some suitable pieces.

Getting dressed for a date and getting ready for it are pretty much the same as a guy, but not so as a woman. It took no time at all to put on the dress, which was the only article of clothing I was wearing, bar panties and shoes. I had worn it before, in the dressing room, but that was behind a curtain with only Chloe to see. Now that I was contemplating going out, in public, where people could see me, it felt like a very small amount of fabric indeed. If nothing else, I associated bare legs with casual, summertime activities, not fancy dinners.

The open back was likewise discomfiting, and let’s not even get started on the front of the dress. I kept looking down and seeing way more boob than I was used to displaying. Chloe assured me that, unless Lamar actually got between my chin and my chest, he wouldn’t have the same easy view. Well, I supposed that my reflection in the mirror looked reasonably modest. Again, the way my clothing looked on my body was far different than the way it felt to wear.

Half the preparation had taken place before Friday night. I had stripped and repainted by fingernails and toenail, opting to stick with the same general color, but borrowing some of Veronica’s polish, which had a bit of sparkle in it. I showered that night and shaved everywhere that needed shaving. My period had ended, thankfully, so I wouldn’t have that to deal with.

While Veronica set about putting my hair up, Chloe produced the jewelry. She nixed my usual bracelet and replaced it with about a dozen thin, gold bands around my left wrist. She gave me dangly earrings, a thing that I had not yet worn. They were shaped like two little golden pendants, each with a ruby at the base. As a necklace, she gave me a giant, bulky golden thing which wrapped around my neck twice and dangled in big swoops across my chest. I was about to refuse — the thing was gaudy in isolation — but a look in the mirror convinced me that she was right. Somehow, the necklace both accentuated and distracted from the cleavage, and I felt a little less underdressed with it on. For rings, I kept my usual collection, even though they didn’t match. I had been wearing them so long that my hands felt odd without them.

Veronica was not lying about her hairdressing skills. My hair was always thick and curly, which felt like more of a handicap than a feature at times. Under her brush and skill with bobby pins, it was swept up and away from my neck, pinned into a graceful pile and pinned with a clip that matched my earrings.

I did my own makeup, but at Chloe’s direction. Luckily I had all the skills required to apply foundation and powder and rouge, eyeliner and eyeshadow, lipstick and mascara. Though I had worn makeup before, I had kept it fairly minimal. I fully expected to look like a clown, but to my surprise I looked like myself. More than myself — I was a polished version of myself. In that moment, the uncomfortable mask of creams and powders realigned itself in my mind. It felt like a lens more than a mask, something to bring my face into focus rather than to obscure it.

The shoes went on last. I observed myself in wonder. Chloe snapped her fingers and ran into her room, emerging with a deep red wrap, to match my nails and the rubies in my earrings and hair clip. I continued to pose, while Chloe snapped photo after photo. Veronica thanked us for letting her help.

“Are you kidding? Thank you!” I felt my hair, worried that I might dislodge it, but it seemed quite stable. The wrap made my back feel far less exposed, too.

I transferred the bare essentials from my purse into the new clutch. Photo ID, a card and a bit of cash, my phone, and a tampon or two in case my body was lying to me. A folding hair brush and a small mirror, some lipstick and other makeup in case I needed to touch up. A different definition of “essential” than what I was used to, but I couldn’t imagine leaving any of it behind.

There was a knock at the door, and my heart leapt up to my throat. I moved to get it, but Chloe waved me back. “Stand there, right in the light. Feet together. Good. Now hold your purse in both hands, right in front of you. No, tuck the ends of the wrap between your arms and your body. Just like that. Now, angle your head down just a bit, no, too much, there, and when he comes in, look up at him with just your eyes.”

In other words, if you’ve ever wondered if women plan out these little things to achieve maximum effect, I can set your mind at rest on that point. They do.

And it works.

Lamar was poleaxed. He could barely string two words together when he tried to tell me I looked nice, but I thanked him for the compliment as if he had just delivered a sonnet. He didn’t look half bad himself, with a tailored jacket over a burgundy shirt and khaki pants.

Then it was my turn to be rendered speechless, as he produced a single rose from behind his back. It was a sort of creamy pink, and it smelled like heaven.

I think we might have stood there for ten minutes, awkwardly grinning at each other, but Veronica whisked away the flower to put it in one of our taller drinking glasses, and Chloe directed us toward the door. I think she made some sort of joke about waiting on the porch in her rocking chair and polishing her rifle, and giving us a curfew of ten, but neither of us were listening.

I have put a lot of thought into the matter, having considered it from both sides, and I think that a photo of a well dressed woman cannot convey how beautiful she actually is in that outfit. She might tramp along like a farmer in mud boots, or mince along as if she’s walking on spilled Lego blocks. I blessed the skills I had been given, because I moved with grace.

Perhaps grace is not the right word. Imagine wearing comfortable clothes, something designed not to impede your movement. Picture the feeling of freedom and ease of those clothes. You could run, you could jump, you could dance. Now, try to move that way in high-ass heels and a short-ass dress, your hair twisted into a sculpture and your face slathered in paints. If you can carry that off, then you’re there.

I took his arm, and we walked to Avenue A. He apologized for not getting us a car, or at least a taxi, but when I found out that restaurant was in the Village, I told him not to be silly, that it was a lovely evening and I was happy to walk. I did have to ask him to slow down a couple of times, but I knew I was walking slower than usual in my shoes. Plus, I didn’t mind that he felt excited. I did too.

Dinner was Italian, not one of the super expensive places in Little Italy or the trendy ones in Hell’s Kitchen. Just a nice little trattoria, with good red wine and good red sauce. I would describe the food in detail, if I remembered it better. It was not the sort of meal where the individual elements stand out. I remember being in a haze of happiness, talking about nothing in particular, drinking in the sensation. Every sense was stimulated, from the smell of the bread, and the taste of the wine, the gentle lights and the gentle music, and the touch of Lamar’s hand on mine. He had reached out to hold my hand as we waited for the entree, and I was afraid to move mine, in case it made the moment end. But after we finished our main course, and before the dessert, we held hands again, and after that there was no reason we wouldn’t continue to as we left the restaurant.

We walked for a while, neither of us wanting the evening to end. I suggested a park, but since Tompkins Square was not the safest at night, we turned instead into a small community garden which had not been locked up. We sat on a bench, tucked away from the world. I discovered to my pleasure that his arm fit very nicely around my shoulders, and my head rested very neatly on his.

Only the cooling air drove us to move. He did not feel it, but he also wasn’t wearing such a short skirt. We went back to the apartment building, and never did the four flights of stairs seem so long. Soon, the evening would be over. I suppose I could have hung out with his roommates, or he could have hung out with mine, but that would be an anticlimax.

When we arrived at our floor, we spotted a note pinned to the door. “Gone to Brooklyn for Dave’s buddy’s party. Gonna crash on his couch. Peace.”

“That’s convenient,” Lamar said.

“Very,” I replied.

“I guess if you’d like to come in for a bit, we....”

“I’d love to.”

“Okay.” He grinned. “Yeah, all right.”

We went inside. The Catan game was still unfinished on the kitchen table, but the usual dirty food plates and pizza boxes had been straightened up. He asked if he could get me anything, and I requested a glass of water. I sat on the sofa, and he brought it to me.

My heart was beating hard. Now that we were here, there was another bump to get over. After a moment’s though, I realized what it was. Last time, he had made the first move, and it had not gone well. This time, he was wondering, what would happen if he tried again? How would I react? I knew the answer to that, but of course he did not.

Well, better to settle the question. I set the glass of water on the end table. I stood up, reach up on tiptoe, and planted my lips onto his.

Guys miss out on one part of kissing. I placed my hand on his chest, just below my head level, and felt his heartbeat. I knew that mine had doubled in speed, and now I could tell that his had too. Once again, he wrapped his arms around me, and I leaned in closer. I stretched up my arms, encircling his neck as he encircled my waist.

People throw around phrases like “time stopped” far too often to make that an effective description. Say rather than my sample rate increased dramatically, like a camera taking a slow-motion video. Every bit of my body was contributing to my senses, nothing blocked out. I felt his lips, the firm weight of his arms, the press of his body against mine. And yes, I felt the same heat as before growing inside me, but this time I was not afraid of it.

After an age, we broke apart. “Wow,” he said.

“Yeah,” I said, and grinned up at him.

“Wanna do some more of that?”

I bit my lower lip and nodded.

We moved quite naturally to the couch. Lamar sat with his back against the wall, and I nestled next to him, turned slightly towards him, my legs tucked up under me. This put our heads on more or less the same level.

There is a sort of negotiation that goes on with making out, especially if it’s your first time. Where can you get away with touching? What can you get away with doing? I had played that game myself before, on the other side. You don’t want to go straight for the boobs or the butt, Move too fast, and you risk derailing the whole thing. Instead, you start with places that are a bit less intimate, like the back, sides, and shoulders. You keep your hands in motion, stroking and stimulating, getting closer and closer. Depending on how your partner reacts, you can withdraw, stall, or press on.

I was now on the other side of this game, and understanding the rules did nothing to detract from my enjoyment. I now had a new role, which was to react appropriately. I wanted to encourage him, which meant kissing more forcefully, or making little moans of pleasure. These took very little effort, since I would have been doing precisely that regardless.

We were well past first base, and I thought we were heading nicely into second, but Lamar seemed reluctant to take that step. At this point my panties were soaked through, and my nipples had achieved a sort of aching hardness that reminded me of an erection, more than anything else. Crushing my chest against him felt good, but I desperately wanted more direct stimulation.

I decided that some direct intervention was needed. First, I removed the necklace, which I knew would only get in the way. Then, while my hands were still around the base of my neck I untied the halter top.

It did not fall off immediately. Now that the fabric was no longer anchored, by breasts naturally spread apart and a little down, which tugged the halter down a bit. I looked at Lamar’s eyes, but he was no longer focusing on my face. I’ve heard the admonition, “Hey, I’m up here.” Well, not all of me was, and his attention was precisely where I wanted it to be.

His hands, which had been roving up and down my bare back, slid to the front, dislodging the halter top and allowing to to fall halfway down my belly. I felt the cooler air on my nipples almost like a sting, and I winced audibly. Lamar was about to draw away, afraid he had hurt me, so I decided to speak up. “Touch them,” I whispered.

He complied with alacrity. And I’m here to tell you, the man certainly knew how to work a boob. He did not go straight for the nipples, but cupped and lifted and stroked. I found that the undersides and inner slopes enjoyed his touch the most. By the time, he actually got to my nipples, gently pinching each between a finger and thumb, I was alight with a burning heat.

I had never truly understood breasts as a matter of sexual stimulation. Don’t get me wrong, I knew exactly how they stimulated me as a man. But what did women get out of it, different from any other part of the body? Was it just a cultural artifact, the result of keeping them hidden most of the time, reserved for only the most intimate touch?

That might have been part of it, but it wasn’t everything. I felt a sort of direct connection between breasts and groin. It was a dual channel of fire that burned down some hidden pathway inside me. I felt a rush of blood to my vagina, another flood of moisture, and a growing tingle that seemed to herald an approach to orgasm. My vagina actually spasmed a bit when he leaned down his head and took my right nipple in his mouth. The warmth and sensation of his tongue on me sent a shiver through my whole body.

I felt a sense of release. Not sexual release per se, but a release of tension. I realized that I was fully in his hands now. It wasn’t like I wasn’t participating — my body was writhing under his touch, as he traced a line of kisses from mouth to jaw to neck to chest. When he kissed my lips, I kissed him back. But he was doing most of the work, stimulating himself through his stimulation of me. In a very real sense I was just along for the ride, and once I realized that, I gave myself over to it.

I swung my leg over his to straddle him, facing the wall. My skirt pooled around my legs, loose enough not to impede anything. My crotch was pressed firmly against the hard lump in his pants, and my hips rocked on him. Bless that mental conditioning — my muscles knew exactly what to do, exactly how to press my swollen clitoris against him to maximize the feeling. We rocked there like that for a time, and the pressure slowly built.

His hands were on my back, my ass, pressing against me and helping me to find purchase. His head dipped to allow him to suckle, then back to my mouth. As my rocking grew more fervent, he simply held me to him, our heads pressed together cheek to cheek, our breath coming faster and faster.

The sensation grew, so great that a cry escaped from my mouth. I couldn’t help it — it had to go somewhere. He did not change the speed of our rocking, but gripped my hips harder, helping me to maintain the motion.

Suddenly, the feeling peaked. Fire and ice and lightning and sensations indescribable suddenly bloomed between my legs. It did not remain there, but ballooned up inside me, sending blots down to every limb. My muscles trembled and shivered, and I uttered a cry that could be described no other way than orgasmic. It went on for five seconds, ten, longer than I had ever felt, longer than I thought I could stand. I could not maintain the motion, but Lamar kept it up for me, building the stimulation to a fever pitch.

Finally it sharped, my muscles spasmed, and I pulled myself up from his lap, almost involuntarily. Then I collapsed down atop him, breasts pressed against his shirt, crotch firmly against his still-clothed member.

I lay there for about a minute, catching my breath. I had never, NEVER experienced anything like that. I did not feel the usual post-orgasm sensations. Instead of pushing past the orgasm and reaching the sense of release and lethargy, my body still felt feverishly stimulated, like I was vibrating at a high frequency that was slowly lowering.

Then, Lamar began to move me again. To my immense surprise, the feeling began to build. Within seconds I came again. That orgasm was shorter, sharper, but no less pleasurable. I arched again as it crested, and lay atop him nearly whimpering.

This time, he allowed the buzzing in my body to calm further. Our breathing slowed. “Wow. I mean... wow.”

“Yeah. You seemed to like that,” he said.

“I think you could say that,” I replied a little shaky. It was hard to get control of my voice.

We were quite for a few moments longer. “How far did you want to do tonight?”

It seemed like a foolish question at first, given what I had just experienced, but I figured out quickly what he meant. Was I willing to let him go, as they say, all the way? Was I going to let him put his dick inside of me?

It felt tremendously selfish of me, but I decided the answer was no. There was a lot I had to process, and at that moment, I simply didn’t feel ready for it. “Let’s save something for the future.” He nodded, but I could tell he was disappointed. Well, I wasn’t intending to leave it at that. “But you know, there’s other stuff we could do.” I shakily dismounted, sliding down to the carpet. “Other stuff I could do.” I unbuckled his belt, unbuttoned his pants, unzipped them, and slid them down his legs. “Stuff I could do to you.” His underwear followed.

Lamar was still wearing his dress shirt, but now he was nude from the waist down. I was just the opposite, topless but still wearing the remnants of my dress like a skirt.

Was I sure about this? It suddenly occurred to me that even more than vaginal intercourse, sucking a dick was pretty much the pinnacle of altered sexual orientation. Would doing this make me gay? Would I regret it afterward? Would this one simple action haunt me?

As if to reassure myself, I reached up to cup my left breast. Its weight in my hand felt comforting. There it was, an outward sign that I was a woman. Between my legs, a pair of soaked panties covered even more evidence, an honest-to-god pussy. I was a woman, and if a woman wanted to give a man a blowjob, there was nothing gay about that.

And then I saw him, standing fully erect from amidst a well-trimmed curl of pubic hair. My heart leapt a bit, and I suddenly realized that I actually did want to do this. He had his fun stroking me, and I was itching to do the same.

I assumed the position, kneeling in between his legs. I wrapped a hand around the shaft. It felt enormous, and rock hard. I felt a sense of pride that I was the agent of his arousal. He was certainly well endowed, although my own smaller hands probably added it. I opened my mouth, lowered my head, and began.

It was the perfect union of something I enjoyed, and something I was good at. The skills I had been given helped, certainly, because I approached the task with a confidence and skill that belied my inexpertise. Added to that, however, was the fact that I had been on the other side, and I knew just what pressure would feel best. I could read from the tension of his leg muscles, the sound of his breathing, just what he was experiencing. He placed a hand on my head, tangling his fingers into my hair. It pulled a bit painfully, but in a sense I enjoyed that too. I was driving him beyond civility, beyond politeness, into a place where he was commanded by his desire, desire for me.

Through some instinct, I knew just when to break contact. A few strokes sent a hot jet of semen spraying onto my chest. It quickly cooled, even as I gave him a few finishing strokes. A bit of sticky cum dribbled onto my arm, and another few drops fell to the floor. I looked up at Lamar, who appeared fully spent. As he saw me, he also became quite embarassed.

“Oh geez, I’m sorry, I...”

“What, this?” I gestured down at my now-shiny breasts, and shrugged. “Honestly, I kind of liked it.” And as I said it, I realized it was entirely true.

Movies and books usually cut away at this point, but real life doesn’t have that advantage. He got me a towel and I cleaned myself off. I put the top of my dress back on, and laughed when Lamar made a grumpy face about it. I made one of my own when he put his pants back on, and finally we settled back on the couch to enjoy the afterglow. I rested my head on his chest, felt the rising and falling of his breath, and thought about how good life was.

Finally, we parted. He walked me to my door. “Thank you, kind sir, for the lovely evening,” I said, formally presented my hand for him to kiss. “We shall have to do it again sometime.”

He looked up from my hand, a truly naughty expression on his face. “All of it?”

“Oh yes,” I said. I went on tiptoe to deliver one last kiss, and went through the door. Just like that, always leave them wanting more.

I know I did.

7