The Holiday Party

I lifted up, and I admit it was cool to feel that toy sliding out of my ass. I stopped at about the right time. I had a tight squeeze going on with my nether regions, and I could feel the contours of the head. I lowered myself slowly, then repeated over and over. I can't say I liked my first anal. We didn't really connect emotionally, because I was too distracted by the pain during an act that didn't feel natural to me yet. I was not used to remaining dilated at the entrance like this, and it just felt like I had to go to the bathroom the entire time. I was still happy to do it for my friend that I loved. I started moving my hips around, not just up and down. I wanted to cause the smaller bulb end of the dildo to move around more in Elena's pussy and hopefully make her feel good. It worked, and she let me know.

"Are you going to come?" she asked "Is it working at all?"

"No, I don't think so. I can get myself off, but this is just too intense with the anal. You?"

"Not sitting. If I am on top or standing I can even when I am doing the fucking."

"Have you fucked me enough yet? Did you officially take my anal virginity now?" My ass still hurt, and my squat muscles were tiring.

"Yes," she laughed.

I lifted up, and the dildo plopped out of my butt with a tiny burst of pain. I pushed the dildo back with my butt and sat in front of it and leaned in to kiss her.

"Ooh, nice," she said as the dildo probably rubbed her G-spot while I pushed my end of the shaft down.

"To be continued..." I said.

"I hope so," she replied.

I felt we needed a break or even that this was a natural ending to our night. I stood and was horrified by what I saw. There was no mistaking the little bit of brown lube on the shaft. "Eww," I said and tried to wipe it up with the only thing I had, my dress, before she saw it.

"A little of that is normal, it's anal after all," she said.

"I'm so embarrassed," I muttered, my red-cheeked face looking down. I suddenly felt stupid. I was a naive virgin and had no business doing anal. I was annoyed with her for talking me into it. And what kind of stupid girl does anal anyway and refuses normal sex? I would mock someone for this. I put on my shoes and got ready to go.

"You can stay. Come on, silly."

"Sorry, this whole night is just weird. I have to go. I love you, and again sorry about your dad," I said and hugged her, leaving her standing in her apartment den naked with the dildo hanging out of her as I stormed out. I could not stop squirming in my car seat the whole way home thanks to my anal deflowering. I had that ache you get from pushing things just a bit too far, and every way I adjusted my posture still put pressure on sore flesh and muscles inside my ass.

I was so embarrassed, I went about five days without calling Elena. After some reflection, I realized that I had flaked out and overreacted. But after five days, it became harder to call, so another week went by. Then I was annoyed she wasn't reaching out. It was all so silly, and throughout our friendship, this was the only time we weren't close. I went on a couple dates with guys I had met on an online dating site to distract me, but it didn't help. I had been on a lot of first dates since I had put up a profile a few months ago as the weight came off. I began to feel depressed that I might have lost a best friend. I poured myself into my work, and two more weeks went by. I didn't see her at Crossfit either. I switched times on most days, and when I did go at our usual lunch time, she wasn't there. I assumed the worse case scenario of her avoiding me.

On a Thursday I got some fantastic news. I'd been working very hard in my first job since college. The company wanted to promote me, but it would mean a move to the other office a three hour drive away immediately after the new year. I accepted, but I was sad knowing I would be leaving my best friend, especially on bad terms. This was the big break I was waiting for, so I broke my lease and planned on moving that weekend. I would start in the other office as soon as possible the following week.

The news of my promotion triggered a chain reaction of events that ended my virginity that weekend. The news finally brought me out of my funk and elevated my mood. I was riding a wave of confidence and happy emotions going into the wildest weekend of my life sexually and didn't know it.

It started early Friday morning when I stood on the scale before my shower. I had done it. After months of dieting and hard work, I was at my ideal weight, or rather, a pound under. I arrived at work by 7:00 in the morning and settled into my cubicle like always. I was usually one of the first people at the office and could get a lot done in that first hour before others began to bug me. On Friday it was even more obvious, since people generally dragged in later than normal. We had an open landscape design, so I had a cubicle even as a manager. The only difference was mine was in the back of the row near the window, and it was a little bigger with taller walls for more privacy.

I couldn't stop thinking about sex. A lot was going on to make this a peak hormonal time for me. It was the right time in my cycle. I had an abundance of endorphins from the promotion and move. I was slimmer and felt sexier than ever before. I pushed my chair in closer to my desk to hide everything below my waist. I had a knee-high dress with full nylons on. I began just lightly rubbing my thighs together as I tried to work on email, but really I kept thinking about Elena. Then I'd think about dick, then Elena again. I hiked up the dress and rubbed my pussy on top of the nylons. It felt so good. It was so exciting to do this at work, knowing at any time a coworker could drop in. If I was lucky, I'd hear anyone with a few seconds of warning. I stared at the monitor and put one hand on the mouse to improve the charade.

I stayed on top of the pantyhose until I was ready to climax. I was still on a daily masturbation routine and was getting better at it. With each session, I could make my body respond faster to my touch. I reached orgasm quickly, and I think the public aspect of the lewd act helped. When I was close, and at the last possible second, I reached under the nylons and my panties and ran my fingers through my thick bush. I found the little nub and hit it at just the tight time, sending me into an early morning bliss and wetting the fabric for the next few hours. I exhaled deeply but managed to suppress any noticeable moans. It was a great early start to the weekend.

I was able to concentrate and get some work done after a good orgasm and two cups of coffee. By 5:15 in the afternoon, I needed a different kind of release since I had to work through my usual lunch workout. I hit the 5:30 Crossfit class. The cool shower afterward felt great, but I had to put the same work clothes back on and return to clean out my work space to move to the other office. I decided to go commando under my dress. I hated pantyhose, and the panties had been on all day and just seemed gross. This was a rarity for me, and I was definitely uncomfortable with the idea.

It was 7:00 by the time I returned, and the entire floor's cubicle farm was vacant with the main lights dimmed to save energy. We had dedicated employees, but on a Friday nobody stayed late. If they had to work, they would log on from home. I packed in five minutes with one small box. I had almost no possessions at work. As I was about to leave, I heard keyboard strokes one aisle over. "Aren't you going to say goodbye?" he said over the cubicle wall.

Jeremiah was in accounting. He wasn't the manager, but we all knew he held down the department. He was working late closing the month end, which he had to be in the office to do, given our archaic ledger software. I rarely had to work on projects with him, but when I did, I was thoroughly impressed with his professionalism and skill. I was a bit of an overachiever also, and often we were the last people to leave at night. The problem was he hit on me and asked me out a while back. I declined, office politics making me refuse to date at work. But the whole truth went to a darker place, which I had pushed aside amid more convenient excuses. Once I became a manager, I distanced myself more. I felt kind of bad. He respected me and never asked again, but part of me wished he had tried a little harder.

I went to the other aisle as requested. He was well-dressed as always and greeted me with a warm smile. He was a very fit and handsome black man about two years older than me. He was also tall; one of the only men on the floor more than an inch or so taller than my 6'1" frame. "Being a martyr again?" I said.

"Congrats, I heard. You deserve the promotion, but we'll miss you here." His eyes drifted down to check out every inch of my body as he talked.

Maybe because I was leaving for good, I felt like flirting. When his eyes drifted back up but stopped halfway up, I countered with, "You mean you'll miss me. Look up here, not at my tits. There, that's better." I was opening the can of worms for whatever stupid reason. My cocky grin was out of character for sure.

Jeremiah took the bait and got right to the point. "How come we never went out? I can ask now with you leaving and all. You know I think highly of you, always have."

"And I you. But we work together."

"No, that's not it. You went out with John from wherever."

"Marketing," I said. "Two floors down, totally different department, come on. Not the same thing." This inquiry would normally be annoying, but it felt more like flirting. I was having fun. "And that was a one-time mistake, by the way. Huge Napoleon complex."

"It's about race, isn't it?"

Dead silence for a few long seconds. I looked around to check that we were still alone. I was annoyed. Being from the rural Midwest, this whole race card thing was a foreign concept to us. I'm not sure what came over me next. At work I was an alpha girl for sure, aggressively pursuing career advancement. But not with men. I was inexperienced. Normally I would just confidently walk away. I wasn't feeling particularly sexy either. My dress wasn't one of my best outfits, and I was in flats. I didn't wash my hair in the shower after the gym, so my hair had drying sweat in a ponytail. I had little makeup on and wasn't wearing panties. But I had hit my target weight that morning, and I felt like my body was sexy, and that mattered the most. I moved into his cube and got between him and his keyboard. I pushed it out of the way and leaned back slightly, my butt against the side of the desk. I put my hand on his chest and pushed him in his wheeled office chair back to give me room. I folded my arms on my chest and just glared at him.

"You're not going to turn into a whiny bitch now are you?" I said. "I didn't think you had that chip on your shoulder." He looked surprised. I smiled to ease the tension a bit, and he looked away, a little embarrassed. I found the lever on the side of his chair with my foot, and he went crashing down to the lowest setting, putting me in a better position to look down on him. He didn't say anything, and I realized he was waiting for an answer. "You liked me, even when I was fat." He nodded. "You could have any woman you want, hell you probably have many women you're stringing along right now. Why me?"

"I do okay," he said. "You're different than most women. I don't know exactly why. You've always stood out in my mind."

"What do you think of me now? Too skinny for you?"

He finally laughed again. He picked up his phone and acted like he was looking at it. "Girl, your ass is like avocado. It's the good kind of fat."

"Yeah, my Instagram feed has the same memes as yours." I paused, then looked serious. "You're right. A little. Mostly it's the dating at work holding me back though."

"Huh?"

"The race. It matters. I admit I'm not perfect. I have my reasons, and it wouldn't be exactly as you expect."

"Ah, honesty," he said.

I think this would end our conversation if it wasn't for the obvious fact that I was into him at that moment. I went back to the aggressive persona, but it was clear now I was at least partially faking it. "That doesn't excuse you from being a bitch about it though. A girl doesn't owe a guy an explanation for rejection."

"Fair enough," he said. "Seriously, you're super cool. I've always had a thing for you. I just couldn't ask more than the one time. I had to respect your answer."

My heart melted a little. I didn't get this kind of attention often, and Jeremiah wasn't desperate for female attention. I looked him in the eye confidently as I slowly lifted the hem of my dress up to expose more thigh. He took the hint and looked at my leg. It was a knee-high dress with loose fabric, so what I hand in mind was feasible. "Go down on me right now, or never speak to me again. Don't stop until you're finished," I said. "Debunk the stereotype. Service me and send me off right after that remark."

"Here in the office?"

"I'll let you know if I see anyone coming down the hall. I just showered at the gym, so it's nice and fresh for you." I grabbed his chair and pulled him close. The tall stud wouldn't have to bend far to reach me. He gripped my thighs, then lifted my dress to expose my pussy. I took the fabric from him so he could work.

"Celebrating your promotion with a little racist innuendo and sexual harassment, I like it," he said as he brought his head to my bush.

I was out of character for sure being a little dominant, so I was relieved when Jeremiah went for it. I'd been on the receiving end of oral sex lots of times even though I was technically still a virgin. Half a virgin, I corrected myself with some amusement. I dated a guy for a few months that had some skills, and it happened also with a few other guys I wasn't as serious with.

He kissed me first on the inner thigh, spreading shivers throughout my body as he peppered the surrounding area with his wet lips. Occasionally his shaved head rubbed against my belly or vulva and added to my pleasure, so by the time his lips and tongue touched my privates, I was truly aching for him. Finally, he gratified me with a tongue flick against my protruding clit, followed by many other light strokes before opening my petals with a downward exploration of my crack.

This wasn't the easiest position for oral, but it worked great for me at least. He had to focus on my clit, because the standing position with my legs close together with him in front of me made the hole harder to reach. It was a huge turn on to stand over this powerful man and have him do exactly what I had demanded, putting my needs first with no hint of reciprocation. We were alone in a sea of cubicles, but knowing someone could interrupt us also made the experience hotter.

He looked up and smiled as his tongue was buried between my crack. His strong hands caressed my thighs, then reached around and grabbed my ass cheeks, pulling me slightly away from the desk I was leaning against. "Come for me, Brit."

"Won't be long. You're pretty good at this," I said. I was building toward a climax quickly. It was hard to pinpoint why he was better than other men that had eaten me out, but every touch seemed to have a purpose, and he hit just the right spots with the right amount of pressure. He never stayed in one spot, covering all the parts of my vulva even while the focus was on my clit. He teased the entrance to my hole as best he could in that position, and he even slid in a little. I wondered if he could tell I was still a virgin, but he didn't say anything.

As orgasm approached, I pinched and rubbed my right nipple as best I could through the fabric of my bra and dress. The closer I was to orgasm, the stronger I liked the pressure on my nipples. When I masturbated, one hand usually attended a breast while the other rubbed my clit. Near the end, I didn't mind a slight bit of pain. It actually made the experience better for me as long as I waited long enough.

He knew when the timing was right, and he zeroed in on my clit, hitting it at all angles, even sucking the whole clitoral hood into his mouth. The assault on my button was harder than the light strokes in the beginning, and only now near the end could I have handled this. He was good at reading me. I pulled his head into me hard when the moment arrived. I struggled to contain my voice in public as I grunted softly when the waves of energy rocked me.

He looked up at me affectionately and patted my butt. I could see the evidence of my high arousal all over his face. "How was that for you, love?" he said.

"That was a good one." I pushed his head back and started to walk off. "Maybe I'll see you at the party tomorrow, if not, then that's okay." Fake-dominant Brit was back.

"Wait, was it really all about you?" He stood. "I won't be there tomorrow, so a hug goodbye at least?"

"You were my going away present," I said. I leaned in for the hug, but I also reached down and grabbed his crotch through the pants. Something rather large was waiting for me. "Damn, okay. Well, show me what you got." I leaned against the desk again, hinting that I might stay.

"Sure." Jeremiah seemed very eager as his fly came down. A giant slab of black cock spilled out for my viewing pleasure.

I stared. I couldn't help it. "Good lord."

"I can't debunk that stereotype, sorry."

"That's the biggest dick I've seen," I said. I'd only seen five before in real life (yes I kept track), but I was sure I could scour the earth and be hard-pressed to find his equal. Jeremiah's offering tapped into something primal in my mind. I realized I was still a virgin only partially because of my convictions. The other half was never being tempted like this. I had an overwhelming need to feel him inside me. I lifted my butt and perched myself on the very edge of the desk. "Come a little closer," I said, reaching out to grip his member as he approached. His swelling unit was flaccid still, but he was already wider and longer than any man I'd seen. His cock felt heavy and powerful in my hands. He was uncircumcised, which seemed odd at first, but I got over that in about two seconds and liked the natural look. I retracted the foreskin to reveal the shiny, giant head that was a few shades of brown lighter than his shaft. I wanted him. I didn't plan on losing my virginity to a man I'd never gone out with and likely wouldn't ever go out with, but my mind was made up. He didn't need to know that yet, though. "Yeah, you're not coming near me with this monster," I said. "It's going to get even bigger."

"You can handle it, girl, we just have to work it in. Spread that big pussy for me."

I laughed, thinking yeah, on the outside. I'm a tiny, timid girl inside. He didn't seem surprised I had said it, and I had a feeling I wasn't the first woman to balk when she saw his big dick. But I was also salivating. I always enjoyed a good challenge.

Jeremiah moved between my legs. He was six inches from glory now. All I had to do was lift my dress again and give him the green light. "I'm not on the pill, and let me guess, no condom either?" I asked. He shook his head no. I pushed my hand under his cock through his fly. I cupped his balls gently. The skin was smooth and hairless, and they were huge. This man seemed so potent.

"I'll pull out in time, no worries. Let's fuck, baby."

I laughed, happy to hear his enthusiasm. "I don't want to get pregnant," I said. I miked his cock, this time from closer to the base until my hand was out of his pants. "See," I said. A drop of fluid oozed out onto my finger. Despite not being hard yet, he was already leaking. "Your pre-cum is white already. You have a loaded gun." Enjoying pretending to be much more experienced than I was, I brought my thumb to my mouth and made a big show of licking the semen. There was enough to get that taste for sure: the strong taste and scent of sperm, not regular pre-ejaculate. I lifted my legs and used them to pull his hips closer to me.