The Summer Associate

The summer started out normally enough, I guess. I had just finished my second year of law school at Penn, and was lucky enough to secure a prestigious Summer Associate position at a Chicago law firm. At first I thought about finding a summer sublet for the ten weeks I would be in the Windy City, but in the end I decided that I would stay with my Aunt Paula and her family. It wasn't the most glamorous plan, but it would definitely save me money and the living arrangements themselves were actually probably nicer than anything I could have afforded on my own.

Paula, my mom's younger sister, lived with her husband Gary and their three daughters in the heart of Lincoln Park. Their house had an open-plan living room, dining room, and kitchen on the main floor; two bedrooms upstairs for Gary and Paula as well as their youngest daughter, Eve, who was around ten; and two more bedrooms in the finished basement for their older daughters. Melissa — or Missy, as most of us called her — graduated from high school a week before I arrived; her older sister, Kim, was spending her last summer of college bumming around Europe with friends, leaving me her room. There was a large hangout room downstairs with a large flat-screen TV and some overstuffed sofas, and our own bathroom.

As excited as I was about the job, I was also excited to spend the summer with my younger cousins, whom I hadn't seen since the last big family reunion five years ago (I wouldn't see Kim at all while I was in Chicago, but since she was studying at Bryn Mawr we saw each other pretty regularly in Philly). I figured a lot had changed, but I wasn't prepared for what I saw when Missy got home from her job as a counselor at a day camp.

The last time I saw her, Missy was suffering the worst of being thirteen years old: pimples, braces, bad hair — really bad hair, and an awkward body that was not quite a woman's but definitely no longer a girl's. I distinctly remember my deep sense of pity for what her life must have been like at the time, so when the door opened and a tanned, smiling, nicely-proportioned beauty breezed in, it took me a moment to recognize her. Missy's light-brown hair was just a little wavy and fell loosely around her shoulders; her green eyes sparkled as she smiled. It was hard to see her exact figure beneath the bright green t-shirt with the name of the camp written across the chest, but it seemed like she had filled out decently. Her legs, muscular and toned, extended down from her shorts. She had grown to 5'7", just a bit shorter than me.

"Jake!" she squealed when she saw me, running over to give me a big hug. "It's so great to have you here! We're going to have the best summer!"

I laughed. "You do realize I'm going to be working all the time, right?"

Missy made an exaggerated pout. "Weekends?"

I shrugged. "Who knows? I might end up sleeping under my desk!"

Now Missy laughed, and we headed into the kitchen to catch up over snacks.

*****

There's not a lot to report after that first day — my expectations were all too accurate, and I found that my regular schedule involved getting home well past midnight, throwing my clothes over the back of Kim's desk chair, and collapsing in bed for a few hours before dragging myself out of bed, into the shower, and back to the office.

Still, I managed to find time for family. Gary, Paula, and Eve I saw mostly on the weekends — Sunday brunch, barbecues, that kind of thing — but usually once or twice a week Missy was still awake when I got home at night and we'd sit on the basement couches or in one of our rooms and catch up. As late night conversations will, things got personal, so I wasn't surprised when, a few weeks after I moved in, Missy was waiting up for me when I got home.

"Hey, kid," I said with a smile, setting down my bag and shedding my tie and suit jacket. "What's happening?"

"I wanted your advice on something," Missy replied.

I flopped down on the far side of the couch. "Shoot."

"There's this guy, one of the other counselors at the day camp. He's a couple of years older — a sophomore at DePaul — and he asked me to go with him to a party on Friday night."

"So far, so good..."

"That's just the thing — I'm not sure if I want to go."

"Like not sure if you want to go at all? Not sure you want to go with him? Or you want to go out with him, but not to this party?"

"Like not sure what I'm not sure about. He's a nice enough guy, and good looking, but I don't know if I really want to hook up with him."

"So don't. Or do you think that's his expectation in bringing you to the party?"

"I'm not sure about that either. I wasn't like Kim in high school, I didn't really date much at all and I don't have a lot of confidence around this stuff."

"Have you done this kind of thing before?" I asked.

"Which kind of thing? Go with a guy to a party? Or hook up?"

"Either?"

"I didn't go to a lot of parties. Not my thing, I'd rather stay in with some girlfriends and a movie. And I didn't hook up so much, either, which is probably all related." I nodded.

"I had kissed a few boys," Missy continued, "At smaller get-togethers — not ones you would call 'parties,' just a few kids in someone's basement for the evening. I let one or two feel me up, but the only time anything really happened was after prom, when I blew my prom date in the limo."

I raised an eyebrow in surprise. "A boyfriend?"

Missy sighed. "No boyfriends for me. Just a guy from class, Kevin. We were sort of in the same circle of friends and he asked me out, and he had a reputation for being a nice guy so I figured, why not? He was good friends with my friend Jessica's boyfriend Max, so we ended up sharing the limo with them and our other friend Anna and her date, some guy from a different school none of us knew. Anyway we had this limo, and it was like a flat rate for the night, and we didn't really have anywhere to go — some of the kids had hotel suites but there was NO way my mom was going to allow that."

I nodded, knowing how Aunt Paula could be.

"I think she would have flipped her shit if I had even gone to someone else's suite," Missy continued, "And Anna's parents are also really strict, which is kind of ironic because she's a really big slut despite how psycho they are about keeping tabs on her."

Missy stretched out her legs and went on with the story. "So basically we just told the driver to take us around the city, nowhere in particular, and we put up the privacy screen and there we are in the back of the limo and Anna is all over her date — we had all pre-partied pretty hard, but knowing her she probably also dropped some E — they're kissing, and groping, and we're all sort of sitting there, watching but not wanting to look like we're watching, and not really sure what to do. So Jessica reaches into her purse and takes out a joint, lights it, and takes a drag. She passes it to me and immediately kisses Max, exhaling her whole hit into his mouth. I'm definitely nervous so I also take a big hit on the joint, and then I take another one and I figure I should just relax and follow the other girls' lead, since they were the more experienced ones. Which was probably a mistake in retrospect, but between the booze and the weed and it was like 2 a.m. already, I wasn't thinking so clearly.

"So now this joint is going around — Anna stops humping her guy long enough for them to get some weed too — and Jessica and Max are getting making out pretty intensely, so I start kissing Kevin, and he's feeling my boobs through my dress and honestly I still feel pretty awkward about fooling around with all these other people there, even though the lights are way dim, but at this point to stop would be worse — because what are we going to do, just sit there and make conversation while everyone else is messing around? Get out and take a cab home? So when Kevin slides his hands up my legs and under my dress, I just let him do it."

"Did you want him to be doing that?" I asked.

"I don't know," Missy answered honestly after a brief pause. "I mean, I don't think I would have asked for it, but once he started touching my..." She cleared her throat. "Once he started rubbing me down there, I certainly didn't mind how it felt.

"Then he starts kissing my neck and the tops of my breasts (and I'm a little mortified because I'm all sweaty from dancing), while he's doing that I can get a look over at the others and I almost freaked out — Anna's dress is crumpled on the floor, her underwear is on the seat next to her, and she is full on having sex with this guy, who's still wearing his tux, right there in the car across from me, and her boobs (she has really big boobs, like 38Es) are bouncing up and down inside her black lace bra, which is literally the only stitch of clothing she has on now. Her back is to him like she's sitting on his lap and she is completely shaven so I can see his thing going in and out of her as she bounces up and down on him."

I shifted slightly and tried to discreetly adjust my pants; Missy's story had given me a half-chubby. Spying a blanket folded over the back of the couch, I grabbed it and spread it across my lap to head off any further embarrassment.

"Meanwhile Jessica has Max's pants open with his junk out and she's moving her hands all over it while she keeps kissing him, so I decide that the best thing for me is to follow her lead, figuring that she might be going farther than I thought I was willing to go, but at least she won't go as far as Anna. So I reach down and unzip Max's pants, and try to fish his stuff out through the fly. But it's not so easy!"

I laughed. "No, not always."

Missy laughed too. "Anyway, he says, 'Let me help you' —"

"How gentlemanly of him," I quipped.

Missy laughed again, "Right, so he opens his belt and pants and sort of scoots them down around his thighs, and there's his stuff, right there in front of me."

"Had you ever done that with a guy before?"

"No! I hadn't even seen pictures, except for what's in the Health textbooks, and that doesn't exactly capture the essence of the real deal. But I definitely can't stop now, so I reach out and grab it with my hand — I mean, I really have no clue what I'm supposed to do now — and it starts to get harder and thicker. Kevin is still rubbing my panties and that feels good for sure, and between what I saw Jessica doing with her hands and seeing Anna doing what she was doing I have a pretty good idea of what I should do for Kevin so I start stroking him.

"He's not looking at me so I follow his gaze and see that Anna is now on the seat on her hands and knees, fully naked, and her guy has ditched his pants and is doing her hard from behind, her massive boobs are swinging all around. She's propping herself up with one hand and the other is reaching back under her, it looks like she's masturbating. I'm really turned on at this point and I look at Jessica and I see that Max is also watching the show that Anna is putting on, but Jessica is down on her knees in front of him, bobbing her head up and down on Max's penis. And I'm still thinking that I'll just keep doing what Jessica does, so I also get down on the floor, eye level with Kevin's penis, but I sort of shift to the side so I can keep an eye on Anna.

"I really think it might be the worst blowjob anyone has ever given," Missy said, blushing. "I think I heard Kevin wince a few times. I had no idea what I was doing except that it seemed from the others like I was supposed to go up and down on it, and maybe use my hands also. At least it didn't last very long — after a few minutes Anna's guy started grunting harder and she suddenly pulled away and turned toward him, sitting back on her heels on the floor and pushing her breasts together in front of him. He grabbed his own shaft and started stroking it, three or four times and then with a loud groan he came all over Anna's neck, chest, and face."

I glance down and I can see Missy's nipples pressing against the thin fabric of her nightshirt. Thank God I put the blanket in my lap, I thought, as I considered my own rock-hard erection. What a fucking crazy story!

"The other guys take one look at this and they're done. Jessica must have known what to expect when Max started to moan, but I was totally caught off-guard. Kevin came right in my mouth and I gagged, spitting it back all over his lap. A little bit hit my cheek and then I grabbed his penis and pushed it away. I instinctively kept stroking him and he shot three more times, up and all over his tuxedo shirt and jacket."

"Oh fuck!" I laughed. "Imagine explaining that when you return the rental!"

Missy blushed deeper. "Shut up, Jake! I was so mortified, Kevin was in my US History class and I ditched for like two weeks after prom because I was so embarrassed to see him."

"Sorry," I said with a smile, even though we both knew I wasn't.

"So I really don't know if I'm up for that again."

"Although," I said tentatively, "You could potentially go to the party and not blow your date..."

"But isn't that what he's expecting?"

"Not necessarily — I mean, some guys would, but a lot of guys wouldn't. You need to figure out what kind of guy he's like. Unless you're just not into him, in which case you can just decline."

"Thanks, Jake," Missy said, standing. "Your advice is always so helpful. I'm glad you're here this summer." Missy started walking toward her room and then turned back. "Sweet dreams," she called, blowing me a kiss.

*****

I don't know if Missy ended up deciding to go to the party on Friday night or not — for my part, I barely made it home before sunrise on Saturday morning that week. It had been a particularly rough week for the group I was assigned to at the firm, and the lead partner left one of the associates, Emily, with his credit card and told her to take the "summers" out and show us a good time.

Emily and I had been working in the same group all summer, but I knew very little about her. She was all business — not in a mean way, but she definitely didn't invite small-talk. She was a first-rate lawyer, but I could tell something was off about her socially around the firm — the other women kept a discreet but noticeable distance from her; the male associates seemed a little off-balance when she was around them at social functions; and the summer associates seemed to flock to her. Whenever there was a large group at a bar, you would see her lavishing her attention on one of the male summers; but I never heard any talk about whether she was dating, or whom.

That night started out more or less like every other night where the associates entertained us (and there were many of those nights), but at some point — I can't say exactly how it happened, we were already drinking pretty heavily before dinner — the five of us, two associates and three summer associates, ended up at a strip club.

I was frankly a little nervous about the whole thing, partly because I'm not the kind of guy who goes to strip clubs in the first place, partly because these were co-workers, and on top of that because there were two women in the group, Emily and one of the summer associates, and I was sure being in a mixed group would just make things awkward. As it turns out, I needn't have worried: that night, I learned that the kind of woman who thinks it's fun to go to a strip club is liable to get way crazier with the dancers than a man could ever get away with.

We ended up in a private room with two or three dancers — remember, none of us were footing the bill for this — and the ladies were getting the lion's share of the lap dances. Not that any of the guys cared; if you think a lap dance is hot, you should try sitting next to or across from a woman in a business suit getting a lap dance. Emily, in particular, was really out of control. She was petite, at least part Japanese, and about half a foot shorter than me. Her hair, which had been held up with a variety of pins and clips, had long ago fallen out and stretched well past her shoulders. She had surprisingly wide hips for an Asian girl, and the swell of her chest looked like a large b-cup. At first she was just dancing with the girls at the club, but as the night went on (and she drank more) she started really getting wild with them, kissing their necks, pulling on their nipples, swatting their bare asses, rubbing her own tits on their faces and bodies. Like I said, stuff guys could never get away with.

The dancers got really into it also — at one point two of the girls sat on a bench seat and stretched each of us in turn over their laps, face buried in one of the dancers' thong-clad crotch, while the third one spanked us. I have no idea how long we were there, and I don't even want to think about what the tab came out to, but by 4am I managed to get myself into a cab and mumble my address (although it's entirely possible that, at first, I gave the cabbie my address in Philadelphia — thank God he asked me if I was sure before he put the meter on).

I managed to wake up by noon, with a brutal hangover and a boner as hard as Aunt Paula's granite countertops. After verifying that the floor was, in fact, down, and the ceiling up, I pulled on a robe and headed down the hall to the bathroom. I turned the shower water on mostly hot and poured a cup of cold water from the sink. Sipping the water slowly, I considered the sorry state of my appearance in the mirror. Nothing a shower, eggs, and coffee won't fix. I slipped out of the robe and into the shower.

As I washed my body, I let my soapy hand drift down to my cock. After all the craziness of the night before, I needed some relief.

I sat down on the inner lip of the tub and started stroking my meat, coaxing it to its full size. Closing my eyes, my mind turned to Laxmi, one of the secretaries at the office. She had medium brown skin, dark black hair cut to chin length, and long, thin legs. Once I passed by her in a workroom while she was up on a ladder putting a box away, and I could even see fine black hairs growing on her leg above her socks. She looked to be pretty flat-chested, but in my mind that meant that her dark nipples were full and puffy, hardening to little brown points when I grazed my fingertips over them. In my fantasy, Laxmi knelt down in front of me in a gray pencil skirt and light-blue oxford shirt. She had four or five buttons open on her shirt, no bra, and from above her I could see down to her small mounds capped with those succulent puffy nips. Hooking her thin, straight hair behind her ear, she leaned down to kiss the head of my cock. The contrast between my pale white man-flesh and her nut-brown cheek fueled my desire to feel her mouth around me.

Laxmi leaned toward me, her lips parting in anticipation of my dick sliding between them, when Missy burst through the bathroom door.

"In here!" I shouted. How much could she see past the curtain?

"I know I know I know but I really can't hold it and I'm not going to make it upstairs," she said as she made a beeline for the toilet.

I really wasn't sure what to do — I definitely didn't want to jack off with my cousin sitting right there, but I knew I was going to end up with blue balls if I let myself get soft again. The Laxmi fantasy was a lost cause. Slowly, hoping my movements wouldn't be noticed, I pulled on my balls and gently ran my hand up and down my shaft, trying — subtly — to maintain position without giving away what I was doing. The shower curtain was the kind that is fuzzy-clear, which is nice when you want lots of light in the shower but super awkward when your cousin walks in on you beating your meat. The toilet was along the same wall as the shower, in a small nook, but I could see the top of Missy's head in the mirror which meant she could see me if she looked up. I was at a loss for how I might explain why I was sitting down, but I was also afraid to stand in case my junk would be on full display.