When I was twenty-four, in February of my final semester at grad school, I was reeling from chaos in my personal life—to keep an already long story from getting even longer, let’s just say I’d fallen in love with my coworker, roommate, and best friend, who ended up sleeping with our other coworker and lying about it. The first time just so happened to be the same night we’d all gotten plastered together on the Upper West Side and she told me she’d been ‘mortified’ when he asked her out, because they were just friends. They didn’t have the same kind of relationship we did, she said. *Yikes.* The next morning I did not react well, to say the least. The following two months only made things worse. By February we were at the tensest moment of what became a year-long, painful disintegration of our friendship.
I’d also just started teaching my first ever college class, and I was struggling to write my thesis, which wasn’t going well. I needed a win, and perhaps a distraction, so I texted a handful of friends (and women, although my brain wasn’t really there yet to be honest…heartbreak, or whatever) and waited to see who wanted to go out and put up with me at my most glum and self-absorbed. A former coworker, Rachel, responded and agreed to grab a drink. We hadn’t seen each other in a while, so it would be good to catch up. Understand that I didn’t think any more of it—not only was I depressed and heartsick, but I also just didn’t see her as a potential sexual partner. Rachel was the junior agent and office assistant at a literary agency in downtown Manhattan, and had been my direct superior for the eight months or so I’d worked there as a paid intern. She was thirty when I started, and I was only twenty-three. Along with the vice-president, she’d even been the one to interview me when I first moved to the city and heard about the opportunity.
Back then I was in the midst of a different romantic meltdown, which had me moving out of an apartment I’d just moved into—from Chicago, no less!—only a week before I started grad school. Perhaps this is part of why I’d never noticed Rachel earlier, as anything other than the second-youngest member of the office and person whose desk was closest to mine. Plus, if I’m being honest, I just hadn’t grown into myself at the time. I saw myself as the same skinny, awkward, nerdy kid I’d been in high school, friends with most people but not all that confident with beautiful women. In any case, we agreed to meet up for drinks at a French wine bar on 8th Street, not far from school. We’d gone out once before after my internship ended, for whiskey at a diver bar in the East Village, but it had been friendly and not much else, at least to me. I figured we’d drink some wine, eat some charcuterie, and gossip about our favorite writers and those we were working with professionally, or in my case as a student. I guess on some level I saw it was networking—Rachel was a junior agent now, and by the time I finished my book maybe she’d be a senior one, able to represent my work. It made sense to stay friends.
I arrived first and lucked into a table. This place was always busy in the evening, thanks to its location and romantic atmosphere—something that I hadn’t considered when picking it, focused more on the ability to order inexpensive wine flights. It was cold outside, and I was dressed for it in the semi-new wardrobe I’d put together with Christmas gift-cards and help from my mother (so sexy, right?), who felt I needed to look more like an adult if I was going to fool my students into thinking I was an authority of some kind. I wore slim-cut, dark jeans, a fitted buttondown, and a thick, cowled cardigan with suede elbow patches. My peacoat, newly retrieved from the tailor, was slung over my chair. My brown Chukkas were covered in sidewalk salt, a hazard of the city in winter. I’d started keeping a well-groomed beard around this time, another effort to remind my students I was older than them, if only just. I ordered a glass of Chinon and fiddled with my phone until Rachel arrived.
The first thing I noticed was her coat: a peacoat, like mine, but lurid, Pepto-Bismol pink. Not my thing at all. But then she took it off…it was like seeing a completely new person. Rachel was tall, with long legs—she often wore riding boots over tights or jeans, something that just *does* it for me—and a great body. Thin, but not overly so, with a cute butt that she couldn’t hide, even with her relatively modest professional wardrobe. That night, however, she wore a dark grey dress, slinky without looking déclassé, cinched at her waist with a black belt. It was cut fairly low, highlighting her décolletage. She had *great* breasts, perky and big on her frame but still well-proportioned for her scale. I’m not one to stare, but I had to stop myself. How had I never noticed before?
“You look, uh, you look…great,” I said, always the smooth one.
“Aw, thanks!” She smiled and took a seat.
Understand, of course, that much of this physical memory comes in retrospect. Sure, I noticed she looked “great,” but I was also so stuck in my own emotions at the time that I didn’t think anything of it. She asked me to order her a glass of wine—a full-bodied red—and I settled on a Châteauneuf-du-Pape. We talked about work, and I found out she’d left the agency, but mostly I spent my time complaining about my roommate, Nora, and how she’d broken my heart and lied to me and I still had to work with her and see both of them. I was insufferable, I’m sure. I was insufferable for a good two-and-a-half years of my life in New York. The fact that Rachel maintained interest is a testament, I guess, to one of two things: either I’m just that desirable, even at my worst, or—and this is more likely—she was going through just as much personal-life shit as I was, and needed a distraction just as badly, if not moreso. After a few more glasses of wine each, so cured meat and cheese and cornichons, and a hell of a lot more of my complaining, the waiter came over to herd us away so they could free up the table. Rachel glared at me, but didn’t say anything.
“Are you okay?” I asked, signing the check. “You seem…it seems like you’re mad at me.”
She looked me right in the eyes. “Were you in love with this girl? Did you *love* her?”
“I…uh…well, yes. I mean, I guess, yes I was.”
She swigged her flute of Prosecco and set the glass down sharply. “Let’s go.”
***
For some reason we took a roundabout route to the subway, heading down 5th Ave and cutting through Washington Square, under the arch. It was dark and cold, and few were still in the park at this hour, other than scattered homeless people and a handful of entrepreneurial drug dealers who stayed in the darker corners, mistaking us for undergrads and trying to peddle us their shitty weed. We were almost to the corner of MacDougal and West 4th when Rachel turned to me suddenly, breaking her silence.
“I don’t…look, maybe I’ve misunderstood all this…” She shivered a little, and the finished her thought. “But…well, I just really want to try this.”
She pressed herself into me, stood on her tiptoes, and kissed me with more force than I’d ever been kissed, literally rocking me back on my heels. She was rough, feral, biting my lip and shoving her tongue into my mouth. One of the dealers hooted.
When she came up for air, I stepped back. “Wait, stop.”
She looked embarrassed. “Oh, I—”
“It’s not that! No, that was…great! I just feel a little weird making out in front of the crowd here.” I gestured at the various onlookers.
“Do you want to come back to Ditmas Park?” she asked between further kisses, biting my bottom lip. “I live by myself. We can do anything we want.”
“That sounds amazing—” I felt myself growing hard at the mere suggestion. “—but I have a class to teach in the morning, and my laptop’s at home.” She kissed my neck as I spoke. “Also, don’t you have cats?”
She stepped back for a second. “A cat, yes.”
“I’m *really* allergic to cats.”
“So is this not going to happen?” She pouted, but looked legitimately hurt.
“What about my place?” I asked. “It’s not that far, and you’re welcome to stay the night if you don’t feel like heading back to Brooklyn super late.”
“What about your roommate? Won’t that be weird for you?”
I kissed her, taking charge for the first time, grabbing her ass through the layers of pink coat and grey dress. Pausing for breath, I made up my mind: “I don’t care. I just want to fuck you.”
***
The train ride to Queens was interminable. Rachel kept trying to make out with me, couldn’t keep her hands off me, but I wasn’t drunk enough not to be self-conscious. All the people around us! I kept stopping her, trying to spin it as something seductive—worth the wait, all that. We got stuck at Roosevelt Island, as if the MTA was hell-bent on prolonging Rachel’s release and my discomfort about public displays of affection. Eventually, of course, we got to Jackson Heights, walked briskly to my place, a third-floor apartment in a privately-owned house not far from the border of Woodside. Nora, the complicated roommate, wasn’t even home.
After all the buildup, all the groping and kissing in the park and on the train, I half expected us to end up against the apartment door—although my fantasies usually outstripped my actual, in-person moves. The alcohol and drawn-out train ride, however, meant Rachel wanted to use the bathroom. “It’s fine,” she said. “Just get in bed and I’ll be there in a second.”
If I’m being honest, I was intimidated by the whole situation. Here was a beautiful woman, seven years older than me and far more experienced—she was an oversharer at work, so I’d heard some stories—who apparently wanted whatever I could give her. My sex life had been fairly intermittent since breaking up with the old girlfriend and the start of grad school two years earlier, just a hookup here and there followed by a lot of pining for a girl who didn’t feel the same way. I didn’t really know what to do—the whole situation was way more cinematic, way more adult, than what I was used to. Don’t get me wrong, I’d had plenty of good sex before that night, but it had been awhile and it’d always been with peers and girls my age, during relationships or mutually drunken nights. Rachel and I were tipsy, but not wasted, and we were hardly peers—I couldn’t help but think of her as my ‘boss,’ and myself as the intern. I sat in bed, worrying about what to do, how to advance things when she came back, and by the time she actually did open the door and step into my room, I was still fully clothed, reclined on the bed in everything apart from my winter coat.
She, on the other hand, was topless. She’d discarded her dress (and shoes, and belt) on the floor in my apartment’s entryway, and was down to her tights. This time I stared. Her tits were perfect—bigger than you would ever guess from seeing her in clothes, and incredibly perky, keeping their shape perfectly but still moving, naturally, while she moved. Her nipples were the size of quarters and erect, angled just slightly upward. Pretty much exactly this shape and these proportions: [Imgur](https://i.imgur.com/k2Yn26x.jpg)
I sat up on my elbows, and she laid down next to me, on her side. “So,” she said.
“So.” I didn’t know what to say. “Sorry. I’m a little nervous.”
“Don’t be,” she said, reaching for my hand. She guided my hand underneath her tights, and panties, and I started rubbing her clit. She moaned deeply, kissed me again, and started undoing the buttons. “Did you ever think about this while you were at the agency?”
I paused. “I mean, I think I always looked at it as ‘you were my boss,’ so no, not exactly. But I always thought you were hot.”
“Did you?” she asked, biting my lip again and starting on my shirt. “Be honest. Really?”
I curled two fingers shallowly into her, and she pressed herself into me. “Of course,” I said. “You’re sexy as hell.”
She tossed my shirt aside, quickly pulled my undershirt over my head. “What about me is sexy?”
“I really like the way you look in boots,” I answered. “And fuck, you seriously have the best breasts I’ve ever seen.”
“You like my tits?”
I leaned down and circled my tongue around a nipple.
“Fuck,” she said. “Fuck. You need to take my tights off. *Now.*”
I kissed my way down from her nipples to her stomach to her waistline, slowly peeling off her tights and panties as I ventured lower. By the time my tongue found her clit, she was arching her back and squirming.
“I always thought you were cute,” she said while I went down on her, tasting her, my hands spreading her legs open and pressing against her well-trimmed strip of pubic hair. Her moans got louder. “I pushed for them to hire you,” she said in between heavy breaths, “over anyone else. Because—fuck!—because you were sexy.” She clenched her hands, bunching up my sheets. “I thought you were so charming—god, *yes!*—and when you read the story I wrote, the one that was published a few months ago, about my sleeping with the real estate agent?”
I winked. “Yeah? Was that based on you?”
She reached down and played with her clit while I explored her with my tongue. “You. Know. It. Was. Me.” She squeezed her thights against my cheeks. “When I thought about you reading the scene. Where I blew him on the floor of the. Show apartment….I just couldn’t stop imagining your cock. You playing with yourself. Touching yourself while thinking. About me. Going down. On him.” She turned her face into my pillows and moaned. “Stop,” she said. “Stop. I need your cock.”
In one expert motion she undid my belt and fly and pulled off my jeans, kissing down my torso as she went. My cock was straining against my boxer briefs, and she kissed it like that, pressing her lips around the outline of my shaft. The view of Rachel on her knees, bent over me, teasing my cock, was almost too much her handle—those perfect tits in prime view, her plump lips pressed around the shape of my cock. Before too long, she pulled off my underwear, and my cock—rock hard, by this point—sprang free. (Luckily I had ‘manscaped only a day or two before, for no particular reason. I hadn’t expected this!)
“You’re *huuuuge!*” she said, gripping me softly in one hand and turning me too stare at every angle.
“Oh?” I said, feigning ignorance.
“Like, I always thought you were sexy,” she said. “But I *never* would’ve expected this.”
“I’ve been told this before,” I told her, “but I guess I never thought much of it. Seems like the kind of thing you just say during sex because you’re supposed to…”
Rachel laughed. “I don’t believe that,” she said. “You’re fishing for compliments. You know you’re big.”
I smirked. “I mean, a girl or two has struggled to deepthroat me, sure.”
A look of determined confidence came over. “We’ll see about that.”
I’d be lying if I said it was the best blowjob I’ve ever received, but it was good. Certainly one of the most enthusiastic. She was sloppy, loud—she’d take as much of me as she could (which was most!) and then slowly pull away, strings of saliva running from my cock to her lips. She was the first woman (can I call her a girl? She was seven years older than me!) who ever spit on my cock for lubrication. And again, the view. I couldn’t take my eyes off her perfect tits, bouncing and jiggling just slightly when she got particularly enthusiastic, nipples still at attention.
A year before, I could never have pictured this, and even as it happened it was incredibly surreal, this woman who’d told me to digitize files, or pick up paper goods at K-Mart, was bent over me, completely naked, gagging herself on my cock. The weirdness of it kept cropping up at inopportune times; the situation was hot, but it also kept tweaking my nerves in such a way that I struggled to finish, a surprise given the relative lack of sex I’d been having. “Come up here and fuck me,” I finally said. “I want to feel you.”
“Get a condom first,” she said, out of breath.
I reached over to the bedside table while her mouth was still on me, fumbling blindly for a condom. When I found one, I handed it to her and she rolled it on with ease.
“Just so you know,” she said. “It’s really hard for me to finish. So, like, don’t take it personally.”
“That’s okay,” I said. “Is there anything—”
“No,” she said. “Don’t worry about it. It just happens or it doesn’t, it’s not you. I was really close while you were going down on me, but I wanted to see if we could both finish during sex.”
I nodded. We were both slick with sweat already, and out of breath. She straddled me and slowly lowered herself onto my cock.
“Fuck,” she kept saying. “Fuck, you’re so big.” She inched her way down, shockingly tight. “You’re just a lot bigger than I’m used to.”
Finally, I was fully inside her. She paused for a second, adapting, and then started to speed up. I grabbed her at the waist and came up to meet her, the sound of skin slapping skin. “Holy fuck. Yes!” she screamed. “Fuck! Yes! You. Feel. So. Good.”
As fun as it was to watch her bounce and grind on me, and to see her facial expressions contort, once I felt sure she was used to me I flipped her over to fuck her from behind, a favorite position that usually made me come way too quickly. The weird mix of wine and nerves must have helped that night. Anyway, Rachel had the filthiest mouth of any woman I’ve ever fucked, far more than I can accurately replicate here. She was loud, screaming and moaning so much that I felt sure my downstairs or next door neighbors would complain or give me side eye in the morning. (The block was entirely row houses, with shared walls.) We shook the bedframe and knocked an Old Fashioned glass of the nightstand, which I ignored. Twice I slipped out and accidentally pressed into her ass. (“Wrong hole,” she said with a grunt.)As I fucked her from behind, watching her cunt grip my cock and her ass flex, she kept hitting her head on the bedframe. (Like every other student in the city, I had a MALM.)
“Fuckfuckfuckfuck,” she shouted. “Fuck me with your huge cock. Fuck me, fuck me, fuck me.”
Since she obviously liked dirty talk, I tried to play along. I wasn’t much good: “Do you like being fucked by my huge dick?”
“YES!” she screamed. “Shut up and keep fucking me. Fuck. Yes.”
We kept going for what seemed like forever, probably my longest orgasm-less fuck to this day. The condom dried out, and she was sore, so we paused for a second to catch our breath. My shoulders ached from being over her for so long. Rachel pulled the condom off and lazily went down on me again, each of us laying on our side. It’d had been well over an hour at this point.
“Close your eyes,” she said. “Picture the office. It’s a Thursday, and everyone’s out to meetings, or to lunch. You’ve stayed at your computer because you brought a sandwich.”
I could picture where this was going, and I liked it.
“Earlier you couldn’t help but notice that I wore a more revealing outfit than usual—tighter jeans, with my Fryes. A form-fitting sweater. You thought I didn’t catch you staring, but I did…Why do you think I went to the bathroom for so long?”
I groaned. Felt my back arch and hips buck, driving my cock deep into her mouth.
She gasped, a line of saliva stuck to her chin, when she came up for air. “You’re along in the office, so you turn to my desk, my computer, and start sneaking through my files. It’s a lot of junk, contracts and permissions documents and manuscripts, but after a while you see one titled ‘Intern,’ dated all the way back to September, when you started.”
She spit on my cock. “You start reading it.”
“Holy *shit!*” I groaned. I could feel my balls tightening, my cock throbbing. “Fuck.”
“It’s about your interview, and how the assistant—that’s me—can’t decide what to say to her boss. Should we hire the cute guy who just interviewed, with a good resumé? Or should we hire someone else, so the assistant can steal his phone number, call him, and fuck his brains out in…where did you live then?”
“Harlem,” I gasped.
She reached down with a hand to help out as she licked all the way up the underside of my cock.“In Harlem.”
I couldn’t take anymore. “Fuck, Rachel, I’m going to come. Fuckfuckfuck.”
“Don’t you want to hear the end?” she asked, stroking faster.
“I don’t care,” I said. “I just want to come on your perfect fucking ti—”
But it was too late. I exploded, a fountain of come, rope after rope—all that buildup, all that anticipation, the illicit fact that she’d been my ‘boss.’ The first shot caught her on the chin and nose before she got her mouth around me, and she did her best to handle the rest. When I finally finished, twitching and giddy, there was another dribble of come down her chin. She smiled and opened her mouth, sticking out her tongue to show me the load. Then she swallowed. “That was awesome,” she said. “Holy shit!”
She kissed me, come still dribbling down her chin, and went to the bathroom. I set my alarm, worried about missing the first day of workshop with my undergrads. When she came back, we spooned for a while, both worn out but far too riled up to sleep.
We ended up fucking again before bed, first on our sides but then with me on my back, and Rachel facing up, so I could rub her clit and nipples at the same time, but she couldn’t quite get there. By the time we fell asleep, it was 5:00am, and I had to be up in three hours to teach class—but that didn’t stop us from one more spirited effort in the morning, where I finally got to unload (albeit less this time) on her perfect breasts. She left, headed to her new corporate job downtown, and I showered, drank a pot of coffee, and left for class.
We never slept together again.
Source: reddit.com/r/gonewildstories/comments/7llnpp/in_grad_school_i_unexpectedly_hooked_up_with_my
Dude, this is a really cool story! Thanks for sharing :)