That Time I Convinced My Ex I Was A Prostitute [F/M]

Big ups to /u/wilson48 for not only convincing me to share this story, but also editing it thoroughly for me. If you haven’t read his stories, they’re awesome, though he could stand to share some more ;)

This story is an oldie but a goodie, taking place a couple years ago. I had a boyfriend at university, (I’ll call him “Logan”) we started dating as Freshman, and broke up at the start of our senior year. To keep it simple, he was a sweet guy, but our post-university plans weren’t lining up and the fire was pretty much gone. A week after we broke up, he was far from over it, but we were instantly friends again – we’re friends to this day even.

Fast forward a few months after our breakup, Logan and I ran in similar crowds, so him and I are hanging out at a low key birthday party for one of our shared friends. It’s a great night, and Logan and I are still hitting it off well as entirely platonic friends. At one point in the night, one of our friends brings up this one insufferable guy from a class most of us had together, and how there was a rumor going around that he had hired some sort of Craigslist hooker.

As the drinks flow, the jokes about Craigslist hired-ladies never seem to end. At one point, one of our friends was fundamentally breaking down the question as to how desperate someone had to be to hire some form of prostitute while in the hormonally charged world of university. I distinctly remember him asking, “who in their right mind would do that?” and I remember a drunken Logan raising his hand immediately. Everyone broke out in laughter as Logan played it off as a joke, but I glared in his direction, suspecting there was more to that story.

When I had a couple more drinks than I should have had in the first place, I sat across the table from Logan – most of our other friends are shooting pool, focused on some sports game on the TV, or otherwise preoccupied. I ask him genuinely how he’s doing and we catch up. Teasing the issue, I bring up how he joked that he’d be interested in a Craigslist escort, and ask him if things had really been so bad since we broke up. To my surprise, he answered fairly honestly, saying that he hadn’t been with anyone since we broke up. I was a bit taken aback, I certainly didn’t want to tell him how much fun I had been having since we broke up, but he broke the awkwardness by making some joke about how I had ruined him for other women. Returning the joke, I told him I owed him a prostitute then, telling him I’d have to find him the “grimiest lady Craigslist had to offer.” We laughed, and he joked “hell, I’d take anything at this point.”

I rejoined my friends at the party, feeling a slight pang of pity, but mostly just larger pangs of the alcohol in my bloodstream. I had greatly enjoyed my first few months of newfound promiscuity after our breakup, knowing Logan quite well, I figured he just wasn’t responding well to change, a constant problem of his. All the same, it seemed a waste. The night grew longer and longer until we all decided to part our separate ways. Logan was perhaps the drunkest of us all, so I volunteered to walk him home, as his place was on the way to mine. The whole walk, he spouted drunken insecurities, at one point even asking if he sounded ridiculous saying he would have sex with a prostitute. Not wanting to confront such drunken weighty issues, I just played it off saying that technically, I still owed him a “Craigslist Hooker” and that I’d have to go home and research it. We both had a good laugh and he stumbled his way back to his apartment.

As I made my own stumble home, my mind raced with thoughts. I thought of Logan’s slump – specifically how good he could be doing. While I am known to toot my own horn, Logan was very easy on the eyes: shoulders as broad as a bus that tapered cruelly down to his thin waist with a smile that would make any straight girl (or gay man as far as I know) weak in the knees. Surely, he could be living up the single life. I wondered if I really had thrown him off, somehow cutting away whatever confidence he had. As I slide the key into the lock of my door I think, “how could a guy that looks like that, be so desperate.” And he certainly was looking good that night.

I throw myself down on the couch as soon as I get in, and pull out my phone, shooting a joke text to Logan about how he better not be browsing Craigslist right now. Immediately he texts back, asking “Why? You find something?” Incredulously I text back, my sarcasm surely lost in the medium, “Oh yeah. Found a real gem near by.” Within moments I receive a response: “Seriously?”

Now, I’m that person in my group of friends that refuses to let a joke die – I like to pursue it at any cost. That said, it was also 2 in the morning, and I wasn’t remotely tired yet – in fact, all the drinks I had that night were inspiring some dirty thoughts. All of this cumulated in a perfect storm of an idea. I bit my lip, and texted back, “Seriously. I just gave her your address.” I instantly receive a message back: “You’re joking.” I give it a moment, and commit to my idea. I text Logan back, “Dead serious. I told you I owed you one, right?”

As soon as the message sent, I put my plan into action. I was going to get myself so dressed up that Logan wouldn’t recognize me, that was the challenge to myself at least. Part sticking to the joke, part pitying Logan, and part adhering to my Friday night horniness, I instantly pulled off my casual sweater and jeans, and began to rummage around my closet for the most absurd outfit I could construct. Cannibalizing scandalous halloween costumes and seldom used lingerie, I squeezed myself into the most revealing, assuming, and overall distracting outfit I had ever seen. Wanting to go that extra mile I rushed some gaudy makeup on to my face, including a fire engine red lip. Frankly it was surprising how accurate and quick I was able to apply it all in my severely buzzed state.

Any second thoughts quickly being washed away by the thrill of it all, I gave myself a look over in my full length mirror. Honestly, my first reaction was laughter – I looked comic book heroine whore-ific. I wore a pair of black thigh high heeled boots stolen from a Halloween Bond Villainess costume, a tight vinyl miniskirt I had bought from American Apparel ages before and never worn because it turned way more heads than I had ever wanted, and a silken black lace bustier on top that pushed my cleavage up to an extreme that I still find hilarious to this day. As a final touch, I teased my hair out, making it big and long in a fashion I don’t think I had ever pulled off before. I gave myself a “not bad” nod to the mirror and threw a peacoat on top of everything. Even if it was a strangely warm fall night, I wasn’t about to go into public looking as I did.

I locked my front door behind me as I made my way to Logan’s house, I continue to laugh to myself for going so overboard. As my heeled boots make a reverberating click with each step, I wonder how this is going to go. Will Logan realize it’s me instantly and we’ll all laugh it off? Even if he was old news, the prospect of having some fun tonight still stuck out as a goal of mine – even if sex with Logan was always a gentle vanilla affair. Halfway there, I checked my phone again. About 15 minutes earlier Logan had responded to my last text, saying “Haha. Pick on the drunk guy.” Oh, I hoped to do a lot more than pick on him.

Finally I reached Logan’s apartment, I cleared my throat, thinking of whether or not I wanted to make some sort of change for my voice. Deciding I would just wing it, I knocked on his door delicately. I heard some clamoring about in his apartment, clearly surprised, he took his time getting to the door. I made the most of that time and undid the top few buttons on my peacoat. Eventually he made his way to the door, the locks sliding out of the way to the dimly lit hallway in which I stood. The door swung open and I saw Logan disheveled and shirtless, just wearing a pair of lounge pants. I must have woken him, his chest hard and smooth with his collar bone standing prominently in the low light. Just as I saw him, his eyes didn’t see me, but his eyes lit up all the same. Confidently I murmured, “You Logan?” in an unforgivably bad, but sultry accent. Logan nodded cautiously, and I rolled my jacket off my shoulders revealing my outfit beneath. His drunken gaze caught flame as he looked me up and down.

“Aren’t you going to let me in?” I tease in an equally terrible, but different voice. Again, Logan nods speechlessly, opening the door just enough to let me in, as I drop my coat to his kitchen floor. Looking unsure, I see Logan grab a condom into his hand as he asks me, stammering, “are there any rules?”

Looking to pounce on his uncertainty, I respond, “Oh honey, your friend paid a very good price to ensure there were no rules.” Logan’s apartment is barely lit by one fading lamp in the far corner of the neighboring living room, all the same, I see him protruding in his lounge pants. Just as soon as I look at them, they’re gone, as leaves himself simply in a pair of tight black boxer briefs as he tears the condom wrapper open. I raise a single eyebrow and ask, “Where do we start?”

Logan tugs his boxer briefs off and immediately slides the condom around his fully hard dick – his speechlessness finally breaking, along with the bedroom persona of Logan I was used to when we dated. He gestures down to his dick, “We start with your mouth there.”

Knowing damn well what I was getting into, I grin and respond, “Yessir,” as I find the treacherous way down to my knees from my tall heeled boots. Before I’m even halfway there, I feel Logan’s hands firmly grab my long out of control hair and bunch it up into his grip. I can’t help but feel the excitement given that Logan had neither handled my hair so roughly before or had ever worked up the nerve to demand head from me – I was always the one to initiate. I giggled breathily to myself just before I took his cock in my mouth. Giving someone head with a condom on is normally bad news for both sides, but I loved it, as it signaled that Logan really thought I was an escort. Perhaps it was my hair, perhaps it was the light, or perhaps he was just that drunk – but I loved where this joke had gone, and given the way Logan was acting, I loved where it was going.

I labored over his dick, amidst the flavor of latex and lipstick while I felt him moan and buck. I didn’t think his cock could get any harder, but I moaned with excitement each time he grew in my mouth while my tongue danced around him. Incredibly turned on, I worked as hard as I ever did in our relationship to give him pleasure. He cursed and mumbled to himself as my jaw got sorer and sorer just before I felt a tug on my hair, pulling me up. I drunkenly fumbled my legs, trying to pull myself onto my heels. Before I was even able to stand up, I felt him hoist me up with his broad shoulders, feeling as though I was flying through the air, I knew he was moving me toward his kitchen table, the same one we had broke up around only a few months prior.

I felt my skirt catch and squeak on the edge of the table, the vinyl clinging close to my hips and reflecting what little light was in the room.. Almost immediately I felt tackled onto my back on the table, as Logan buried his face in my chest, one hand grabbing at me hard. I gasped in surprise, not a second of this felt like Logan, but I loved every one. Just as I feel the cool air on my chest as he peeled back the bustier, I can feel another hand pawing at my skirt, eventually conquering it as it snuck in. I felt him come up from my chest as he pushed me further up the table, getting much needed access to my underwear which was apparently too big of an obstacle right now. “Guess I shouldn’t have worn that,” I tease playfully. Logan quickly moves to my side and demands, “Just take it off.”

Again surprised by how direct he’s been, I attentively get to my feet, and begin to undo my skirt, “No time for that,” Logan barks at me, as I instead awkwardly wriggle out of my underwear, stepping each heeled boot out of it. As I get my last foot out of it, I feel an insane sting, as Logan slaps my ass through the vinyl, nearly knocking me off balance. “Shit,” I hear him wince to himself. I growl in approval before bending over his kitchen table, presenting my hips to be struck again. Instead, I feel one hand grab commandingly on to my ass, while his other arm wraps around, hoisting me again on the table, my back hitting the wood hard.

Once more he fights with my tight vinyl skirt, turning it up enough to lead his cock right to me. I let him slide into me so easily as I let out a long pronounced moan, he grunts and moans back to me as he pushes his way in. I try to engage him as each pump has my body heaving in delight, my mind goes to my first working-girl cliché I can think of, “You’re so huge, Logan.” I announce. He wasn’t, but tonight he sure knew how to get a girl begging. All I heard was “Yeah?” as he focused on drilling into me. I dug my nails into his forearms planted on either side of me on the table. I cursed genuinely as he had made me cum in record time. For another moment, all we exchanged were moans of ecstasy, before I heard him call to me through heavy breath, “No rules?” he asked.

Refusing to break character I responded, “No rules. Your friend must like you an awful lot.” With these words he rammed harder than ever into me as I egged him on. Abruptly, I felt him pull out – something I had never experienced in all our time together. I heard his knee land close to my hips as he was suddenly over me. Instinctively I sat up, expecting to take his cock in my mouth again, but suddenly felt something hit my chest as he groaned out in pleasure. Realizing what was happening, I laid back down, knocking a glass of whatever from his table on to me, as I continued to feel his cum make contact with my bustier and chest. “Mmm…” Was all I could let out as he finished. While not normally my cup of tea, awakening this dark side of Logan was an amazing turn on. As he finished, he hung his head in relief, as I had a grin across my face. He stood back up fully and wandered over to where he left his boxer briefs, I found my way over to his paper towels and cleaned up, we were in the kitchen after all.

I looked over to him getting dressed, as he stumbled into his pants drunkenly, I realized just how well this had all gone. I straightened up my skirt and top, before throwing my jacket back on. I could see the light from his microwave displaying that it was 3:25 – even this late, I didn’t want to ruin this by staying over. Instead, I wandered my way over to the door, as I went to leave, I called back to him using our old pet name, “Keep up the good work, Sunshine.” He seemed startled and confused as I closed the door, leaving him only to the sounds of my evil boots clicking themselves away.

Source: reddit.com/r/gonewildstories/comments/3fwl4o/that_time_i_convinced_my_ex_i_was_a_prostitute_fm