The Surprise My Coworker Was Hiding Under Her Dress

My name is Adrián, and I want to tell you about an experience that forced me to tear down almost everything I thought I knew about myself and about desire. I’m telling it because I still find it amazing how heavy the backpack of prejudice I carried for years without even noticing really was.

I grew up in a very conservative family. In my house, talking about sex was taboo, something that simply did not exist in conversation. From the way my parents behaved in public, and even in private, anyone would have sworn I had come into the world by spontaneous generation. There was no abundance of affection either, although, to be fair, I never lacked for anything material.

As you’d expect, I turned out much like them. My relationships were always long, with months of courting before anything happened. My full sexual encounters didn’t reach a dozen, and all of them were with just three different women.

Most of those encounters had been with my last girlfriend. If I’m honest, I think I stayed with her only because she gave me sex. I didn’t especially like her, neither physically nor for her personality, and I found her rather boring. I was stuck and didn’t have the courage to admit it.

A few months ago, a job offer came up in another city, where some uncles of mine lived and could put me up. I accepted without thinking too hard. The job consisted of managing the network for a new company, which in practice meant spending hours locked in a small, poorly lit room, staring at monitors and carrying out tasks at fixed times.

It was incredibly boring. I had no contact with anyone except a supervisor who showed up now and then. From how vague his questions were, I quickly gathered that he had the faintest idea what I did there.

After two weeks of boredom, the supervisor came in with news: I was going to have company. A coworker, actually, who would be starting the next day.

And the next day, just a few minutes before my shift began, the supervisor appeared with a young woman at his side.

—Adrián, let me introduce Nadia. She’ll be your coworker as of today. I trust you’ll get her up to speed quickly, because you’ll be alternating holidays: we want to expand the operating hours — he said.

—Of course, count on it — I replied.

I stepped forward and held out my hand. She shook it with an open smile.

The sight hit me hard: carefully but discreetly made-up, brunette, hair pulled back in a ponytail. The suit jacket emphasized a narrow waist and generous tits straining against the blouse, and glasses framed pale blue eyes that took my breath away.

I went silent for a moment, and the only thing that saved me from looking like an idiot was remembering a movie where a character said out loud what he was thinking. I almost blurted out “nice tits… I mean, good morning,” but I held back.

—Welcome to my domain —I said at last—. Sit in that chair and I’ll start explaining things right now. There are lots of tasks, but none of them are complicated.

—Thanks —Nadia replied, stretching the first “a” in a way that struck me as devilishly sexy.

She moved to the chair, sat down with her legs tightly together, and then twisted her round, prominent ass around to rest her back against the chair. The supervisor said goodbye cordially and left us alone.

I started explaining the tasks while she took notes in a little notebook. She looked at me so intently, with her eyes so wide, that I lost my train of thought a couple of times.

***

At the end of the workday we went out for a drink, and the after-work hangout stretched on amid laughter and jokes. Nadia was very good with programming, so within a few days she developed small programs that automated almost all of our routines. Suddenly we had the day free while at work, except for the occasional specific issue.

All behind the supervisor’s back, of course. When he showed up, we pretended to be intensely focused. Nadia joked that we could bang away at the keyboard meaninglessly, like in movies, and he still wouldn’t notice we weren’t doing anything.

We used those dead hours to talk. Sometimes she would rest her head on my shoulder when I pointed something out on a monitor and was standing behind me. Every night, when we left, we’d meet up for a drink. Little by little her comments got bolder: that she was single, that all the guys she knew bored her. I confessed that I was in a long-distance relationship I no longer believed in.

A month after she arrived, I got a call in the middle of my shift. It was my girlfriend. She told me she’d met someone else, that she hoped I’d understand, that it was over between us. I hung up and, to my surprise, felt relieved. I’d always been a coward, and I was grateful that she had the courage to do what I also wanted.

Nadia asked me what was wrong and I told her. After saying she was sorry, and hearing me reply that there was nothing to be sorry about, she smiled and, with her eyes fixed on the monitor, murmured:

—Well… then we’re both free.

***

That night she was much bolder. She ran her hand over my chest when we laughed, and grabbed my wrist when she asked if I was really okay. I usually drove her home, since she took public transportation. Halfway there, she said:

—Hey, Adrián, we’ve been working together for a while now and we have such a great time.

—Yeah, it’s fun, right?

—I wanted to tell you I feel really comfortable with you. I think you’re funny, easy to be around… and pretty attractive.

—Uh. Well… thanks.

—I wanted to know if, now that you’re free, we could…

I didn’t let her finish. I hit the brakes, looked at her, and lunged to kiss her. She answered with tongue and arms around my neck. A couple of minutes later she pulled away:

—Pull over in that vacant lot.

I drove there in a hurry. When I stopped, she stopped me with a hand on my chest.

—I don’t want to give you the wrong impression —she said—. I can’t fuck today.

I assumed she must have her period.

—But I can give you a really good handjob. I’m amazing at it, you won’t believe it. If you want, of course.

—Don’t worry. Of course I want to.

She grinned from ear to ear, rubbed her hands together, and exclaimed:

—Then come on, pants down!

I sat up against the backrest, unbuckled my belt, pulled my pants and underwear down to my ankles, and pushed the seat as far back as I could. My cock was already hard, pointing at the ceiling, and a thick drop gleamed on the tip. Nadia licked her lips at the sight, leaned over me smiling, and gripped it firmly at the base.

—Fuck, you’ve got a nice thick one —she murmured—. You’ll see. I’m going to leave you as satisfied as a fuck.

She started slowly, sliding her closed fist up and down my shaft, changing the rhythm, brushing my glans with her thumb on every pass. When she heard me panting too much, she stopped dead and squeezed the base with two fingers, as if strangling the climax before it could rise. Then she spat into her palm and started again, this time with her hand slick, twisting her wrist around the head. I told her, practically drooling, how expert her hands were, and she nodded proudly, biting her lip.

—I just love giving handjobs. Watching you all look so stupid.

Ten minutes later, with my balls already tight and sore from holding back so long, she said:

—You’re nice and hot now. Have you ever come with a finger in your ass? It’s way better.

The question surprised me.

—I don’t know. I’m not much for experimenting.

—Come on, don’t be such a prude.

—What if it hurts?

—It won’t hurt, I know what I’m doing. We’re alone, nobody’s going to know, and I promise you it’s worth it. Trust me. Coome ooon…

—Ugh, fine. I’d accept just about anything right now.

And it was true. A week earlier I would have thought it unthinkable, and now I would have said yes to almost anything.

She opened the glove compartment, took out a condom, spat on two fingers, and started gently massaging the entrance to my ass, making very slow circles around my hole while with her other hand she kept jerking me off. Her fingertip slipped, pressed a little, withdrew, returned. I could feel my sphincter opening on its own, searching for that finger. A little later she tore the wrapper open with her teeth, slipped her middle finger into the latex, and said:

—Relax, I’m not going to put much in. I just want to get to the prostate.

—Whatever you say, but I can’t take much more.

She laughed and started going in slowly, pushing with steady pressure.

—A little more… there’s the fingertip… a little more… there.

I couldn’t say where she touched, but suddenly it felt as if a high-voltage cable had shot from my ass to the tip of my cock. Every movement of her finger, every slight inward curve, tore a moan from me, and her other hand, now pumping faster, sent me flying. I barely had time to grab a tissue from the glove box before she sped up both hands at once, her fist moving up and down my dick and the finger going in and out of my ass to the same rhythm.

—I’m about to cum…

She looked at me with a half-smile, eyes bright, and sped up even more, squeezing hard just below the glans.

—Come on, come for me. Let it all out.

I lasted less than ten seconds. The first spurt came out with such force that it hit my cheek before I could cover myself, hot and thick. The second landed on my chest, and then several smaller ones followed, dripping over my knuckles and her wrist. She laughed, easing off little by little, milking me until the last drop, and then wiped my face with a tissue.

—I warned you.

—Yeah… I wasn’t expecting that.

—Did you like it?

—A lot. I didn’t know a handjob could be so intense.

We spent a while talking and laughing before I took her home.

***

The next day she greeted me with a wink and a conspiratorial “good morning.” Midmorning, with no work in sight, she came over:

—I’ve thought of a way to improve yesterday. And we’ll do it here.

—Are you serious? —I asked, my voice somewhere between panic and euphoria.

—Yes. In the server room. If the supervisor shows up, we have an excuse to be inside, and we’d have time to act natural when we hear the door.

It took me several seconds to process it, and even fewer to get hard. I followed her, we closed the door, and she took three condoms from her pocket.

—No way are you getting three fingers in me.

—Not three, but two. The other one is so you don’t make a mess again. Will you let me? Please, please… —she said, making a slaughtered-lamb face.

I snorted, looking up at the ceiling.

—All right. Yesterday was worth it.

This time I was standing, with my pants pulled down to my knees and my already rock-hard cock sticking out of my shirt. She knelt in front of me and, before anything else, shoved it all the way into her mouth in one go. I felt the heat of her tongue wrapping around me, her throat contracting around the glans, and let out a growl that echoed off the servers. She sucked for a few seconds, pulling me out with a wet sound, and then made me turn around and press my forehead against the metal cabinets.

—Spread your legs and stick your ass back.

I obeyed. She worked the entrance from the start, first with her tongue —an electric surprise— and then with the fingertip, now sheathed. She spent a long time with just one finger, up to the knuckle, rotating it inside, while whispering filth in my ear about how tight I was and how badly she wanted to open me up. Then she added the second carefully, pushing very slowly, and when she had both inside she began an alternating motion, as if imitating someone walking, touching my prostate with every step. With her other hand she grabbed my cock from the front and gave me a slow handjob, synchronized with her fingers. After a while I was biting my forearm to keep from shouting. The orgasm shook me from head to toe; I came in spurts against the inside of the condom she’d covered my head with, my legs trembling so much I had to brace myself with both hands to keep from falling.

During that week we repeated it a couple more times. On one occasion the supervisor interrupted us, but we had time to pull ourselves together before he opened the door. Each day I felt looser, freer from the rigidity I’d grown up with.

***

That weekend we went out together and, on the way back, she asked again for the vacant lot. I lived with my uncles, but she lived alone, and I didn’t understand why we never went up to her place. I didn’t want to pressure her.

—So tonight we can really fuck, right? —I said as casually as I could.

—I still can’t.

—Wow, your period lasts a long time.

—It’s not my period, Adrián. I like you a lot. There’s a reason I still can’t, and I promise I’ll explain it to you soon. Please be patient.

—That’s not much of a sacrifice. I’ve waited for much worse women than you.

She smiled and gave me a long, deep kiss.

We kept up the same routine. She even managed to convince me to take three fingers. On the fourth week of our game, on Monday, she told me very seriously:

—Saturday I’ll explain everything, over dinner at my place. There won’t be any games this week. And I’m asking you something, even if it’s hard: don’t masturbate. I’ll try to make it up to you on Saturday. Promise?

I was dying of curiosity, but Saturday would end the suspense. I promised, and I kept it.

***

I arrived at her place and she greeted me in a tight evening dress that accentuated her curves. She gave me two kisses and told me she’d explain everything after dinner. We finished dessert, she wiped the corners of her mouth with a napkin, and stood up.

—Come, follow me to the sofa.

We sat down.

—Adrián, I’m going to change jobs.

—And that’s it? I thought you were going to tell me something else.

—I’m not leaving the city. And I’d like to keep seeing you, if you still want to, after what I’m going to tell you.

—Go ahead.

She looked down for a few seconds, then looked at me, biting her lower lip, and lunged to kiss me. I’d gone a week without coming, so that kiss made me rock hard instantly. Nadia pulled back, looked down at my crotch, and smiled.

—Wow, you’ve got a tent pitched down there, huh?

—As you can see.

Her face turned serious.

—What I wanted to tell you is this.

She took my right hand, brought it to her crotch, and… I felt the bulge. A hard bulge, unmistakable, pressed under the fabric of the dress. I was speechless, eyes wide, taking forever to react. When I did, I folded in on myself, hands over my face.

—Oh, God. Oh, my God.

—Adrián, please don’t react like that. I liked you from the very first day. It’s not something I go around telling people, and when the opportunity came I didn’t know how to tell you. I know you liked me from the start too.

—You should have told me!

—Would we have had this relationship if I had told you?

—No —I answered honestly.

I took a deep breath.

—Can I see it, at least, to make sure this isn’t some cruel joke?

She held my gaze, stood up, and pulled the dress off over her head, leaving herself in underwear. She pulled down her panties, and there it was: a cock, not very big, cut, half-hard between smooth shaved thighs, not a single hair around it.

—Please, Adrián, it’s not such a big deal, and it works for what it’s meant to work for.

—Fuck…

—You don’t have to be afraid. I’m the same person you’ve been with these months. I just… have this. I’m leaving the job, and we barely had contact with anyone else besides that asshole. Nobody’s going to find out. Does it really matter that much? Does it really change all the good times we’ve had?

I looked at her. Up top I saw a beautiful woman, with those enormous tits I’d been obsessed with from day one; down below I saw “that.” But even so, my first impression wasn’t fading.

—You should be honest with yourself —she added—. Despite the shock, look at your crotch.

I looked down. My pants were still raised by an erection that hadn’t let up, outlining the bulge against the zipper. I stood there thinking, said “to hell with it,” and lunged to kiss her. We were devouring each other’s mouths for several minutes, until she pulled away with a smile.

—Come on, let’s go to bed.

***

She led me by the hand to the bedroom. There she unclipped her bra and showed me a pair of magnificent tits —surgery or not, I no longer cared— with dark, stiff nipples pointing upward. Then she started undressing me, tugging at my belt with anxious fingers.

—You’ll notice some differences from what you’re used to. It’s a smaller hole, after all. But it’ll be just as satisfying. You can do it without a condom; I cleaned out really well with an enema. I was hoping you’d agree.

When she had me naked, she looked at my hard, dripping cock and smiled. She knelt in front of me, grabbed it, and took it into her mouth slowly, closing her eyes as if she’d been waiting months for it. She sucked me slowly, her tongue tangling with the frenulum, her cheeks hollowed by the suction. She stroked my balls with one hand and with the other grabbed her own cock and started jerking off on the floor, mouth full. Seeing her like that, kneeling, sucking me while giving herself a handjob, finished melting away every last remnant of doubt.

—Stop or I’m going to cum right now —I told her, pulling her hair back.

Between kisses she sat on the bed, handed me a jar of petroleum jelly, and lifted her legs, holding the backs of her knees with her hands. Her ass, pink and perfectly shaved, was at my height, with her cock resting against her belly and her little hole tight, waiting.

—Go ahead.

I didn’t want to think too much about what I was doing. Almost on autopilot, I took petroleum jelly with two fingers and applied it gently, spreading it around the rim and putting a little inside. She moaned very softly when my finger went in.

—Don’t be rough, okay? Carefully.

I coated my cock well, gripped it at the base, and brought the head to the entrance. I pushed slowly, feeling her sphincter give way, feeling the glans work its way through that tight ring. She huffed, head thrown back and eyes closed, while I moved forward slowly, centimeter by centimeter, until I felt my balls against her ass cheeks. I had her all the way inside.

—Wait a moment —she said, breathing like she was in labor.

I stayed still, feeling her ass pulse around my shaft, feeling her squeeze me in waves. It was much tighter than any pussy I’d ever been in before. A tight warmth, slick with petroleum jelly, threatening to make me come without moving.

A couple of minutes later:

—Okay. Go ahead.

I started moving gently, holding her legs up and resting them against my chest. I pulled my cock out almost to the tip and then sank it all the way back in, watching the hole open around my shaft every time I entered. She was jerking off at the same time, gripping her own cock and working it to the rhythm of my thrusts. The sight —a gorgeous woman, those tits bouncing, jerking herself off underneath while I was fucking her— blew the last of my conservative upbringing to pieces.

—When you’re about to come, stop. Trust me, it’ll be worth it.

I did it five or six times. Every time I felt the climax rising, I pulled out and stayed still for a few seconds, my heart pounding at my temples, until the feeling faded. She laughed and licked her fingers, enjoying my torment.

—I can’t hold out. I’ve been waiting a week.

—Okay, stop. I’ve got a proposal. Want to try the other side? You’ve been stretching little by little, you’re ready, and it’ll be even better than the handjobs I’ve given you.

I froze, cock inside and not daring to move it. It felt like a huge leap. One voice inside me said, “Don’t cross that line, this isn’t the upbringing you got.” Another answered, “This person has already given you handjobs, fingered you, and now you’ve got your cock in her ass. There’s not much leap left. Whatever you are, you already are it. Does it even matter?” The second voice won by knockout.

I nodded.

—I trust you.

I pulled out slowly, with a wet sound, and she laid me on my back at the edge of the bed and lifted my legs to her shoulders, leaving my ass exposed and in the air. She put on a condom, coated her cock with a generous layer of petroleum jelly, and applied it to me too, first with one finger, then two, turning them, scissoring them open. I gritted my teeth, staring at the ceiling, feeling more vulnerable than ever in my life and at the same time more turned on.

—Are you ready?

—As ready as I’m going to be —I answered, uncertain.

She brought the tip to the entrance and started pressing, alternating her gaze between what she was doing and my face, which must have had the expression of someone getting splinters under their nails. I felt the head pressing against the sphincter, pushing with steady insistence, trying to force its way through.

—Relax… you have to relax.

I huffed through clenched teeth, letting the air out between them. Suddenly I felt it give, a sharp burn, and the glans entered all at once. I cried out through my teeth.

—The tip’s in. The hardest part is over. I’m going little… by… little.

—Ah, ah.

She kept pushing, millimeter by millimeter, until halfway in. The burn was brutal, but mixed with something else, a deep pressure running through me on the inside. My cock, against all odds, stayed hard against my belly, with a sticky thread connecting me to my navel.

—We’re halfway. The pain will pass in a second.

—Nadia, it really hurts… ugh.

—Slooowly. There, all the way in.

She stayed still, her hips pressed to my ass cheeks, leaned over me, bending me almost in half, and kissed me hungrily on the mouth. We stayed like that for two or three minutes, tongues tangled, her cock buried inside me, throbbing.

—Better?

—Y… yeah. It’s getting better.

—Good, I’m moving slowly. If it hurts too much, say so and I’ll stop.

—Come on… do it.

She started very slowly, pulling out just a couple of centimeters and then sinking back in, for a long while. Every time she thrust, something deep inside hit a spot that sent a shock up to the head of my cock. My erection didn’t go down even in the worst of the pain; on the contrary, it got harder, thicker, dripping like a badly shut faucet, leaving a shiny puddle on my own stomach. The burn gradually became a kind of dull, strange pleasure that forced my back to arch and had me moaning without restraint.

—God… God, Nadia, don’t stop.

—See? You like it, you pig —she whispered, smiling—. Look at yourself. Look how much you’re enjoying having it inside.

Then she sped up, thrusting with her whole hips now, making her pelvis smack against my ass, and grabbed my cock with a hand full of petroleum jelly to jerk me off at the same rhythm. Every one of her thrusts coincided with a pull of her hand on my dick. I no longer knew whether the pleasure was coming from the front or the back, everything was one electric circuit frying my fuses.

—I won’t last much longer.

—Neither will I. I’ve had the abstinence week too.

—Then let’s come together.

—Yes… I’m there. I’m going to cum inside you, Adrián. I’m going to fill your ass completely.

—And… me too!

As I came I felt her contractions inside me, the hard pulls of her cock emptying against my walls, even through the latex. My own climax gushed out in bursts, one stream hit my chin and the next ones ran down my chest and abs, while my ass clenched convulsively around her cock, squeezing it and milking it. It was the most intense, longest, deepest orgasm of my life. She collapsed over my chest, not caring about staining herself with my semen, between panting kisses. When we looked at each other, we both burst out laughing.

—That wasn’t so bad, huh?

—Let’s say yes —I said, and we laughed again.

We stayed embraced in silence, with her still inside, softening very slowly. There’s no need for me to tell the end: we stayed together, happy and unashamed. That night I understood that the heaviest burden I had ever carried was not between anyone’s legs, but in my head. Who cares about anything else?