Five Guys In One Day

If you know me in real life, you might not believe this story.

If my friends are reading this -- if I found the courage to share it with them -- well, hopefully you WILL believe it.

The craziest day of my life happened about six months ago. That was the day I fucked 5 different guys on the same day. It wasn't planned or anything. It just kinda...happened. I'll try to explain how.

7am: The Hookup

Steve is a guy I'm seeing on a casual basis. It's not anything serious but I do let him stay over when we hook up. He's stayed over enough times now that we've got our own little routines and unspoken rules. One of those rules is, I get up for work at 7.30am, so if he wants a morning fuck, he needs to be finished by 7.30. And I do NOT want to be woken before 7, otherwise I'll kick him in the balls and go back to sleep. But if he kisses up to me nicely at 7am and strokes my ass a little, I will stagger out to the bathroom, pee, come back to bed, and he can basically do what he wants with me for twenty-seven minutes until I need to be up. I kinda like being his sleepy little toy. Sometimes we 69. Sometimes he teases my oversized t-shirt off me really slowly, revealing my breasts and my pussy, playing with me.

Most often though I cuddle a pillow, and he strokes my pussy from behind, and when I'm wet enough he fucks me slowly, either spooning (awkward) or having turned me onto my stomach, pulled my ass up into doggie and kneeling behind me (less awkward, better penetration, not so cuddly).

That was what we did, me with my arms around a pillow, him behind me, hands on my hips, pulling them back, him not really thrusting but using my pussy by dragging it down the length of his cock, over and over, opening me up each time. I wasn't moaning in pleasure or anything but it was definitely "nice", and I was still too sleepy to care all that much or put much effort in.

Steve knows I'm going to hit the shower as soon as we're done so sometimes he likes to turn me on my back right at the last moment and finish over my stomach and boobs. Which he's allowed to do so long as he tries not to get any in my pubic hair, because it's annoying to wash out. I guess the reason I keep things going with Steve is that if I had a new hookup I'd have to make new rules, and that sounds like a lot of effort.

7.30am: I showered, washed Steve's cum off me, got dressed for work, and left.

That was Guy #1. One down, four to go.

10am: The Date

As it happened, I had a meeting in town that morning which meant I wasn't going into the office, and I'd found a little window of an hour to schedule a date. I met James in the bar of the hotel where he was staying. I'd first met him a few months before at a work conference. This was our 5th date, always when he was passing through town with work, always in a hotel bar. We'd shared a couple of kisses, nothing more than that really, a few late night WhatsApp chats but he kept things gentlemanly. We definitely had potential, but that made it worse. Any time I was getting comfortable in his company it got taken away from me again. If he could only stay in one place for a couple of years that would be awesome, provided of course it was somewhere near me.

We had coffee, not alcohol -- it was morning of a work day after all -- and he sat next to me at our table, and his closeness drove me a little crazy. He's not the greatest-looking guy you've ever seen, but he's warm, and smart, and something about him makes me think of home. Whoever he ends up with he'll be a great husband, and a loving father, stable and capable and...

...oh, that sounds boring? Not the kind of thing that gives you butterflies in your stomach? Well, you're reading about a woman who fucked five guys in one day. Might be safe to assume that my relationship situation isn't *quite* as stable as I'd like it to be. Stable might be very attractive right now.

"James," I said, touching his arm. "Can I be level with you? I love our meetups, but I hate them too. I'm starting to wonder if I want any more of them after today."

He paused, looking into the distance as if searching for the right words.

"It's not you. It's feeling close to you and then you being ripped away from me every time. I actually do believe we could be something, but believing that just makes me sad."

"Well," he replied eventually. "Shit."

That threw me a little. "Excuse me?"

"I was just about to say, I've moved some things around, my company is paying for the hotel for a week, so we could try to-"

I didn't let him finish. I felt so much instant regret, I knew I was turning scarlet, and it was either hide under the table, run from the room or just kiss him right then and there. So I kissed him.

We kissed and very quickly we got to a stage where you can't remain in a hotel bar. Shit shit shit. OK. I hastily took stock.

YES, I had sex with another guy 4 hours ago.

BUT...James didn't have to know that, did he?

Was there any physical evidence? I didn't remember any bites or bruises, I knew Steve hadn't finished inside me so that wasn't a worry, and I'd showered straight after. Apart from my vagina still feeling a little...used?...I figured I was in the clear.

We took the elevator up to his hotel room, kissing passionately all the way, and stumbled through his door. Eleven AM on a work day. I was giggling to myself. I'd have to make up some story for why I was off the radar.

Sometimes foreplay is a long, slow build-up of teasing, touching and kissing that electrifies and arouses every part of you. And sometimes foreplay is getting naked and hoping the guy hurries up with his condom so he can get inside your already-soaking pussy as soon as possible.

I lay back, he pushed my legs apart, and with the slightest guiding touch of my hand I helped him into me. He thrust deeply, groaning, and I pulled him close on top of me, burying myself in his arms and chest. I loved how he smelt. I loved how his dick felt inside me. I was almost drunk enough on the moment to tell him I loved HIM, but luckily I restrained myself.

I felt him slowing down, holding himself back. No no no.

"It's OK," I told him. "This won't be our only time. Fuck me. Please."

"But I can't last if-"

"It's alright. I don't care."

I didn't, I really didn't. This wasn't a romantic evening. This was a release, two people finally getting together, a promise of more to come.

I would say he lasted about fifteen more thrusts before collapsing, shuddering, onto me and then rolling off. We laughed together and kissed a while, and eventually the time started to tick by. I was really happy, excited for the week ahead and our adventures to come. I felt a little pang of guilt about doing this so soon after Steve but who cared?

There wasn't time to shower and I had no clean underwear anyway. Still feeling aroused, and still grinning, I got my clothes back on and tried to find the willpower to leave James for my day at work, or what was left of it. He kissed me again at the door of his room and I hurried out of the hotel and back into reality.

Guy #2 done. Three to go.

2pm: The Emergency

One thing about me, I don't generally respond to booty calls. If I have a casual hookup or an occasional thing, I like to keep it legitimate, everyone on the same page, dates planned ahead of time. I'm not a dog who comes running when its owner whistles.

There are exactly two people in the world who are allowed to booty call me. One of them is a guy I've known since high school, his name is Leon, and he's in the Army.

I don't know his exact position or his rank or anything like that, but I DO know: a) it's very dangerous even by Army standards; b) he gets sent to all kinds of random countries at basically zero notice; c) he's often away from family or friends or normal human contact for months at a time. His visits back home are unpredicatable and brief, and unsurprisingly when he IS home he's pretty keen to have sex while he has the opportunity. And, for about the last 5 years, I've been his go-to. He messages me with a time and place to meet, and if I can make it, I do.

Are there rules with Leon? Of course there are. The rules for Leon are, he doesn't have to make small talk. He doesn't have to romance me. He doesn't have to apologise for not being in touch, or tell me he'll miss me, or any other bullshit like that. I am a guilt-free release for him, and he doesn't have to think about anything else while we're together.

Sure enough, on that day of all days, he messaged me.

Just, for a second, put yourself in my shoes, OK? Some totally weird confluence of events occurred, it's 2pm, and against all the odds you've already had sex with two different guys in one morning. You feel excited and impressed with yourself AND a little ashamed of yourself all at the same time. You're also horny as fuck, but that's OK because surely James is going to be in touch any moment now to arrange your first "proper" date, closely followed by your first proper fuck as a couple.

Then your phone starts beeping, and when you look, it isn't James, and it isn't even Steve. It's a third guy, one of the only two people on the planet with booty calling privileges, a guy who probably hasn't touched a woman in months, and he's saying this:

"CITY SUITES HOTEL. 4PM. ONLY IN THE COUNTRY FOR ONE DAY. CAN'T EXPLAIN. PLEASE SAY YOU'LL BE THERE."

If you're me...what do you do?

The truth is, I got wet just reading it. I was dick-drunk. I was in love with myself. I thought about how until I was 21 I could barely find the courage to talk to a guy. I thought about how long it took me to realise how to do my hair, to wear a little makeup, to choose flattering clothes...I might never be a model but I was way more desirable than I'd ever dared to believe. And now there were guys queuing up to fuck me. My pussy was the hottest prize around. I loved the feeling, and I wanted more, and I didn't want to wait.

I replied to Leon within about thirty seconds. "I'LL BE THERE."

At 3.45pm I climbed into a taxi, and at 4pm I knocked on the door of his hotel room.

The only doubt in my mind was: would Leon know that I'd been with other guys that day? Steve hadn't left any evidence, and James wore a condom and finished into that...was it possible I would taste of condom down there? Was that even a thing? I'd had no time to shower. I would have to keep Leon from going down on me. If his face and tongue stayed away from my pussy then I thought I'd be safe enough.

The door to his room opened. There stood Leon. Naked, his honed and lean body, that spent so much of the year hidden under army fatigues, fully on display. And his cock hard and expectant. He had one hand around it and he was stroking it gently. I took a moment just to watch.

I told you! Leon and I don't meet up for small talk.

My pussy throbbed at the sight of him. My third fuck of the day just a few paces away. He walked backwards to the bed and sat on the edge, beckoning me closer. I stepped towards him, undressing as I moved. I unzipped my work dress at the back and shrugged it off. Then my bra, and I saw his eyes light up as my breasts came loose. Finally I paused in front of him and stepped out of my ruined underwear. I'd soaked it through on two separate occasions by this point. I dropped to my knees.

In my left hand I held Leon's cock and I brought it to my mouth. He moaned deeply and lay back on the bed and I began caressing it with my tongue, wrapping my lips around the head. stroking it with my hand before teasing his balls a little. Long, slow strokes of my tongue from base to tip, then I leaned into him and hungrily took more of the stiff shaft in my mouth.

My right hand found its way quickly between my legs and in seconds i had smeared the wetness from my dripping cunt forwards over my clit and I was working myself under my fingertips. I gasped and moaned over Leon's dick as I pleasured myself.

"Jeez," laughed Leon, "you want any help with that?"

I pulled away. "Get on the bed," I snapped as I climbed up. He lay back, I straddled him, and I held his swollen dick steady as I lowered myself onto it. I began to rock my hips back and forth, working his cock inside me, then leant back so his dick would grind into the front wall of my vagina, finding a rhythm together. He had his hands on my hips, guiding me, keeping my soaking little pussy firmly around his cock. I propped myself against his knees to free my right hand and I began to rub my clit while we fucked, slowly at first and then more vigorously. I gasped and squealed as the pent-up arousal of my three-guy day exploded inside me. I doubled forwards onto Leon, burying myself in his arms, my body convulsing as my orgasm receded.

After that I was a plaything for him. He kept me on top for a while but he controlled me from below, taking himself to the edge then backing away, now harder, now gentler, using my pussy to massage every inch of his dick. Then I climbed off him and he bent me over to fuck me from behind, hands on my hips. If I'd been dick-drunk before I was positively high on fucking by this point. My body was on the bed being fucked hard but I was floating in another dimension.

He finished with me on my back, as he held my legs up to his chest, and he fucked me roughly until he froze in ecstasy and poured his seed into my cunt. I lay there a long time after, catching his semen as it leaked out of me and rubbing it around my lips and clit. My pussy was tired. It felt used and tender. I ran the hot tub and we drank cocktails together and chatted for an hour. I think Leon wanted to go again after that but there was just no way.

Three guys in one day: I couldn't believe it. Leon kept asking me why I was grinning.

But of course, the story doesn't end there.

8pm: The Sugar Daddy

So far I hope you realise this was just a crazy day, a one-off. Three guys, and only one of those was planned. The other two were just nice opportunities that came my way and I let my desire take over. Maybe you'd have done the same. Hopefully you haven't been TOO judgmental reading this.

That might be about to change. Because when I tell you about Guy #4...you might judge me a tiny little bit.

Michael is in his late 40s. He's a very wealthy man. I met him through work, at a social function. I'm sure he only started talking to me to be polite, show he was relatable and approachable to fresh-faced interns like me. On our first meeting I mentioned something about finding the cost of living in the city pretty difficult, and maybe I betrayed a little too much, because in truth I was BROKE and worried about the future of my rent payment.

He contacted me a few days later. Michael and I reached an unspoken understanding. It's not like I don't enjoy it, he's a good-looking man who dresses well and takes care of himself. And thanks to him I've eaten at some pretty fancy restaurants and had nights at the theatre and the opera I could never have afforded on my own. And thanks to him, I've never been late with rent, or struggled to pay bills or buy new clothes.

But my side of the agreement is pretty clear. When he calls, I say yes. When he wants to fuck, I remove my underwear and present my pussy just as requested. At 7.30pm, just as I'd got home from my hookup with Leon and I was just slumped onto my couch, wondering what to eat for dinner and wondering how the fuck today had even happened, he called.

"Erm...I'm not really ready to go out or anything," I told him. "I don't have an outfit or-"

"Oh don't worry," he replied authoritatively. "I've got a nice bottle of champagne, we'll order some food, we'll stay at your place. Please, I've had three days of the most ghastly meetings with the dreariest people alive. A relaxing evening with your lovely self is the only thing that's kept me going."

One thing about my "arrangement" with Michael is that I keep up the pretence that I'm quite awkward around men and unlucky in love. Which is often true! Although it had been the total opposite of true today. But he liked me to give the vibe that I was grateful he'd chosen me for this out of all other women. That I needed his dick, otherwise I'd just be sitting around unloved and unused. I wasn't sure if he really thought that about me, or if it was just the costume he wanted me to wear.

I quickly ran around my apartment, changing the bedsheets, checking for evidence that still remained of Steve's presence the night before, straightening things up as best I could. I swapped my work dress for a comfortable but not-too-slobby jeans and a tight top.

It seemed like only a few minute later there was a ring at my door.

Michael entered with his confident, well-tailored air and pulled out the nice bottle of champagne he'd promised from an overnight bag. "Do you mind if I change?" he asked, and reappeared a few moments later in a shirt and jeans.

I talked and ate with a stomach full of nerves. I didn't normally get nerves with Michael. We'd been together dozens of times, and although it felt a little weird knowing I was, essentially, fucking for money, I'd always enjoyed it once we got going. I would say his style in bed was business-like, but he was a VERY successful businessman. He knew what he liked, and what worked, and he did those things. He had one little kink which...well, you'll see.

But tonight I did feel nervous. I felt that somehow he'd know what I'd been doing. The tacit agreement between us would melt away and he'd cut me off, and embarrassing as it is to admit, I still do kinda need the money. What if I was fucked out for one day? What if I couldn't give him what he needed, or my pussy lost interest and I didn't get wet like normal? I'm a terrible liar and terrible at faking ANYTHING, let alone sexual pleasure.

Eventually he followed me into my room and began, in his business-like way, to remove his shirt and jeans until he was just in his boxers. He had a well-tuned body, the kind you get from an expensive personal trainer.

"How shall we proceed?" he asked, smiling. He always said something awkward, but he delivered it so charmingly.

"I think instead of me kneeling, it should be your turn." I perched on the edge of the bed, just like Leon had done a few hours before, and pulled my jeans off.

"I accept," he replied.

This was something I hadn't had so far today: someone's mouth on my pussy. I just trusted to the long soak in the hot tub with Leon that it had washed away any "evidence" of him finishing inside me.

Michael began by kissing up my inner thigh until his lips pressed against my underwear. He explored around, kissing me through the fabric, sometimes over my lips, sometimes nearer my clit, then down towards my vagina. It was working: instead of my pussy complaining or refusing to wake up, I felt myself getting wet, and when Michael felt my wetness through the material of my underwear that was his cue to remove it.

Once he had my sex exposed and spread open he began by licking me from bottom to top, from just above my ass all the way up the middle of my pussy to my clit, opening me up, and then his tongue took the same slow journey again. He found the space between my inner and outer lips, so tucked away normally (he once described my pussy as "discreet") but slowly swelling and spreading at the touch of his tongue. I moaned, shifting my hips around, half lost in the moment of those sensations and half replaying three other fucks at once in my head.

Then he shifted attention to my clit, teasing over and around it to start, then finding a rhythm as he brushed his tongue over it, then a little more vigorously, then with his hand he pushed up on my mound so that my clit was totally exposed.

"Don't stop," I told him. I focused on the rhythmical action of his tongue on my clit, and a sense of tension and expectation began to grow around my entire pussy "Don't stop," I murmured again. I was close. He skilfully began to work two fingers into me, stimulating the opening of my vagina in time with my clit, and it didn't take long to send me over the edge. This orgasm wasn't a frantic release like the one I'd forced out of myself with Leon. This was a wave of pleasure that overcame me and drifted me gently out into the water.