14 Mart 2023

My First Steps To Casual Sex


I’m not sure what first made me take the leap of joining a contacts site for casual sex. I’d often watched porn online, but had never done anything interactive. As a second year university student in London, getting picked up in clubs or bars was easy. When I had an itch for casual sex, it was easy to get it scratched. I guess I’d often found it disappointing though – I’d found guys my age (I’m 20) generally disappointing in bed and certainly nowhere near as good as they thought they were!

So maybe I wanted something a little bit different. I was also keen on having sex for sex’s sake without the tedious “mating rituals” of being bought rounds of drinks over small talk or catching someone’s eye on the dance floor.

Mainly though, I was just curious. I certainly wasn’t going to meet a stranger for sex, I told myself, I was just feeling a bit inquisitive and wanted to know what might be “out there”.

I signed up and completed my profile. I kept it quite “vanilla”, just a passport photo and my vital statistics really. I used my real name, Emma, but kept my surname well out of it! I was mainly interested in what other people were offering and looking for.

I clicked on a few profiles, it was roughly what I expected – regular horny men looking to fuck or get sucked off. Then I came across a profile that really caught my eye – two men looking for an attractive younger girl for a threesome and, ideally, her first ever double penetration.

Wow. Direct and to the point, for sure!

I’d say I’m above average in terms of being sexually active. I’ve been fucked by about thirty or so men and am not at all adverse to hot one night stands. I’m also pretty liberated in bed, I’ve been told by a lot of men I’ve had sex with that I dish out a good “porn star experience”. I definitely wouldn’t describe myself as stunning or gorgeous, but I’m told I’m very attractive. I’m a bubbly blonde, and have a pretty good body, nice, firm 34c breasts and long, shapely legs. My arse is maybe slightly on the large side, but hey, you can’t have it all!

However, despite being pretty open minded, I’ve never had sex with more than one guy at a time. I’ve had a threesome with Karen, a friend of mine, and her boyfriend Jack (basically I sucked off Jack as Karen snogged his face off!) but I’ve never had two men in bed. I watch a lot of MMF porno and find it incredibly sexy, but I had always put it in the box marked “fantasy” rather than something I’d actually try myself for real.

Anyway, I had joined this sex site out of curiosity. I wasn’t actually going to meet people, I was just exploring. I was determined not to be a prick tease and lead any guys on, but what was the harm in dropping these two men a short email message?

So, I just introduced myself. Said I was 20 years old, a sexy blonde university student, looking to explore my wilder side, that I fantasized about getting fucked by two men, but that I wasn’t really sure I’d ever go through with it, but I adored watching girls get double penetrated in porno. I also attached a slightly sexy photograph, nothing too frisky – just me in a loose top, short skirt and black nylons.

Well, talk about “red rags to a bull”! Within just a few minutes I had a very eager reply. Their names were Phil and Terry, two older guys from the other side of London, they adored my pic and would love the chance to “break me in”. They’d be willing to book a nearby hotel room right now if I was willing to take the step of making my fantasy into a reality.

I could feel my heart rate quicken as I read their message. I wasn’t going to actually go through with this. Of course not. But suddenly my idle fantasy seemed to be coming into sharp focus. It was becoming much more tangible, much more easily attainable. I felt I could reach out and touch it. If I wanted to, if I was willing to take the plunge, it seemed I really could get myself fucked by two men – and that very evening.

It was madness, of course. There was no way I was actually going to go through with it. But the tantalizing thought made the hairs stand up on the back of my neck. I was getting incredibly turned on just by knowing the opportunity actually existed – right in front of me on my computer screen.

I messaged Phil and Terry back, saying the concept turned me on like crazy, but I wasn’t sure I could actually take a full on double penetration. I’d been fucked in the arse quite a lot, but being fucked in the pussy and the arse simultaneously seemed really damned hard to take.

They replied instantly. They said it would be very intense, but that they had plenty of experience of giving girls their first DP and that I’d kick myself if I didn’t go for it. And they sent me a link to a video of the pornstar Jenna Haze getting double penetrated. If she can take it, they asked, why couldn’t I?

For the first time, the thought entered my mind that I might actually – just conceivably – go for it.

It seemed crazy, but I was getting more and more turned on. I walked away from my desk aydınlı escort and went to the kitchen to pour myself a very large gin and tonic. I needed a moment to think.

I had no plans for the evening and my boyfriend would be out until very late drinking with his friends. I could stay at home and watch TV or maybe catch up on some college reading, or perhaps I could get myself to a hotel and finally live out a big sexual fantasy of mine.

My heart was beating so fast with nerves, but I could also feel myself getting wetter and wetter. I poured myself another stiff gin. If I was seriously contemplating this, I needed some Dutch courage!

By the time I got back to my PC, I had another message from Phil. It read “Well??? Terry and I REALLY think you should go for it!”

I sent an email back saying I was starting to think I might say “yes”. Quick as a flash, I got another message saying “Great. Why not come to the hotel, meet us for a drink at the bar? If you don’t feel comfortable, you can walk away”.

By now, I was more than halfway to talking myself into going for it. I could go along, meet them for a drink and if I felt uncomfortable, I could just turn on my heels. If Phil and Terry seemed okay, and I felt at ease, well, then I could get myself well and truly fucked. What wasn’t to like?

I dropped them a note saying I was willing to give it a twirl. We exchanged telephone numbers and they suggested we meet at a hotel in Victoria at 6pm. I checked my watch, it was already nearly 5pm and it would take me about 30 minutes to get to the hotel.

I figured I’d better get myself tarted up, I had just been slobbing around at my flat all day and was just wearing a sweatshirt and jeans and no make up. I reasoned that if I was going to go and act like a slut, I might as well dress like one!

I had a quick shower to freshen up and then decided I was going to make a real effort to look slutty and sexy. I slipped on my best, black seamed Victoria’s Secret stockings and a red suspender belt. Then I put on some sexy, red crotchless panties and a super hot red bra. A black leather mini skirt, a tight black blouse and my killer “fuck me” 5 inch black stilettos completed the look. I slapped on plenty of makeup and lots of bright red lipstick.

I looked myself up and down in a full length mirror and was pleased, I looked like an ever-so-slightly-up-market hooker which was just the image I’d been aiming for!

Shaking with nerves and trembling with excitement, I set off from my flat to catch the train to Victoria. The journey took no longer than usual, but it seemed to last forever. I wondered if I’d overdone the slutty look, I got a fair few glances on the train – probably because my skirt was so short that my stocking tops were clearly visible!

I got to Victoria station and looked at my watch, it was ten to six. I sent Phil a text message saying “On my way x” and got an immediate reply saying “We’re already here. What are you drinking? X”. Easy answer – “A very large gin and tonic please!”

I spilled myself into a taxi – there was no way I could walk the half mile to the hotel in those stiletto heels. As the cab dropped me at the hotel entrance, I couldn’t decide if I was shaking with nerves or with sexual excitement. Or both!

The bar was pretty quiet. I hovered at the entrance wondering whether to turn back. I thought I could see two men who I assumed were Phil and Terry in the corner. Trying to look as confident as I could muster, I walked purposefully over towards them.

They clocked me immediately and rose from their seats. “Well, well, well, you must be Emma and – fuck me – you look even better than in your photo. I’m Phil”. Phil was a beast of a man, at least 6’4″, his head was shaved and he was built like a brick shithouse. I’d guess he was in his early 50s. Terry was a bit shorter, maybe 5’11”, slightly on the chubby side, not fat as such, but “rounded” and perhaps a year or two younger than Phil. He gave my arse a gentle squeeze as he kissed me on both cheeks. Both men were well turned out in nice suits.

My drink was already waiting for me and I started glugging away on it as I sat down and crossed my legs. Fortunately, we were sitting in the corner of the bar, otherwise everyone would have got an eyeful of my stocking tops and suspender belt!

Terry got up to buy another round of drinks and Phil used the opportunity to slip his hand onto my thigh, gently caressing my nylon-clad leg.

“You’ve dressed just perfectly for this,” he whispered into my ear.

“Glad you approve, I do my best!” I smiled.

By the time I tucked into my second gin and tonic, the alcohol was beginning to relax me, I was still tingling, but now more with anticipation and excitement rather than with nerves.

Terry came back with the drinks and sat down right next to me and put his hand on my knee. I felt so fantastically sexy and desired. I was glad we were in a discrete corner of the bar as I bağdat caddesi escort was basically being touched up by two middle aged men!

I uncrossed my legs and parted my knees, Terry immediately slid his hand up my skirt to my pussy and started oh-so-slowly fingering me, a smile crossed his face as he realised how wet I was getting. Phil continued to stroke my thigh as his friend was easing his finger into my cunt, he lent over and whispered into my ear “I am so fucking glad you dress like Jenna Haze, I fucking hope you act as slutty as her in the bedroom too!”

Any chance of me turning on my heels and leaving the bar was disappearing fast! I smiled at Phil and said “You’d better believe it!”.

I slipped my right hand onto Phil’s crotch as I continued to sip my G&T.

Jesus. His cock was stiff and huge. My boyfriend is average size – about six inches – but I’d swear Phil had around nine inches of hard, hot man meat and I could feel it throbbing as I gently stroked it through his suit trousers.

I knocked back the last of my drink and Terry, who now had two fingers up my snatch, said in a firm, serious voice, “I think it’s time we went to the room”. It was now way too late for me to disagree, so all three of us stood up, left the bar and made our way to the elevator.

As we got in, it struck me that not only had I never been with two men before, I’d never taken cock from guys this old. I tried to put out of my mind that these guys were older than my parents as I put my arms over Phil’s shoulders and lent forward to let our lips meet.

He pressed his body against me as our tongues mingled and I could feel his massive, hard dick throbbing against my navel.

Within a couple of seconds, the elevator pinged and the doors opened on the sixth floor.

Terry ushered us out and guided us down the corridor. Rushing through my mind was just “Oh my God…Oh my God…I am actually going to take dick from two guys.”

Terry swiped the keycard in the room door and we hurried into the room.

“Get your tits out and get on your knees,” Phil demanded.

I was now fully into this. I tossed off my blouse and pulled off my mini skirt and sunk to my knees in the middle of the room. Given the situation I’d got myself into, I thought I may as well try and act like a porno star.

“Come on guys, get over here and let me suck on your hard cocks.”

They didn’t need a second invitation. Terry was the first to unzip and I eagerly slipped my hand into his trousers, slipping out his firm dick. He was also bigger than my boyfriend, about 7 ½ inches and nice and fat. He was already oozing precum.

I looked up at him making eye contact, holding his cock just in front of my mouth. “Suck it, you fucking slut,” he groaned.

I rolled back his foreskin and gently placed my tongue against his bellend, looking him straight in the eyes as I eagerly lapped up each drop of precum.

He was already nice and stiff, but as I slipped his cock into my mouth I felt him harden even more. “Oh yeah, suck on my hard dick, you fucking cumslut,” he gasped.

This was so electric, finally I was living out my sexual fantasy and out of the corner of my eye, I could see that Phil had got his enormous cock out and was wanking it slowly but determinedly.

I reached out my right hand to make a grab for Phil’s huge manhood. Kneeling there, in my stockings and heels giving head to one middle aged guy as I was wanking off another made me feel so wanton and so horny. I’d never been so slutty in my life and I was loving it.

Phil shuffled towards me, his monster dick now right in my face. I kept wanking Terry and turned my mouth towards Phil.

“Go on, get a good taste of what you’re soon going to feel in your tight arse, you dirty whore,” he grunted.

“Oh yes, treat me like your fucking sextoy,” I pleaded as I started running my tongue along Phil’s shaft. I now realized just how huge he was, bigger than nine inches if anything, how the hell I was going to get this monster up my tight little asshole was anyone’s guess!

Terry started ripping off his clothes, so I started to give Phil my full attention, giving his dick gentle suction and plenty of tongue action.

“We’re going to rip you wide open, you filthy slut,” Phil laughed as I worshipped his dick with my mouth.

I could see Terry making his way to the bed and sprawling across it, his firm dick sticking straight up in the air.

I took Phil’s cock from my mouth and looked up at him “God, fuck me like a dirty whore, guys, please, please, please!” I begged.

Phil smiled. “Go and impale yourself on Terry’s cock, you cock-loving bitch”.

I stood up, stripped off my bar and panties, so I was now just wearing my stockings, suspender belt and stilettos and took a couple of strides towards the bed. I knew now I was only a minute or two from experiencing my first ever DP – and from two middle aged men I’d barely met!

I straddled bahçelievler escort Terry and smiled down at him as I held his dick against my pussy lips and let out a gasp as I slowly lowered myself onto him. I licked my lips and gently pinched his nipples as I did so.

“Oh yeah, take it right up your cunt,” Terry shouted at me.

I did as I was told, easing him all the way into my pussy, clamping my nylon-clad legs either side of him and then leaning forward and letting my tongue slip into his mouth.

Terry eased his hands down to my arse and gently parted my butt cheeks.

Oh my God, I knew what was coming next. I felt Phil apply some lube to my tight little hole.

“Bet you’ve never had a cock this size up your arse before, have you bitch?” Phil chuckled as he coated his cock with lubricant.

“No. God, no. I haven’t,” I sighed.

“Make sure Terry has a good view of your face, he loves to see a slut’s facial expression as she takes an anal battering.”

With those words I felt Phil clamber onto the bed. I clung onto Terry tightly, bracing myself for what I knew was coming.

Phil’s gigantic, greased up cockend was pushed up against my arsehole. Slowly but determinedly, he started to edge his way in.


“Bit fucking late to say that now, darling,” Terry whispered as he watched his mate sink into my arse.

My face must have shown a perfect mix of agony and ecstasy. Feeling myself pinned between two dirty old men, dressed like a whore, submitting myself to the sluttiest experience I’d ever had. But also wondering how the hell I was going to cope with nine inches up my arse.

“Right, I’m about halfway in,” said Phil – as Terry continued to hold my arse cheeks apart.


I knew I was going to be pushed to the limits. Part of me was terrified about whether I could take what was happening. A bigger part of me didn’t want to be anywhere else.

I gripped Terry even tighter, took a deep breath and looked down. Terry had a smile a mile wide on his face. He was clearly enjoying seeing me struggle to take it. I could feel his dick pulsing in my pussy. Phil was still edging his way up my arse. I remembered back to that Jenna Haze video they’d emailed me.

“Oh God. Go on, then. Fuck me, you dirty bastards!” I shrieked. I thought my arse was going to break as Phil pushed all the way in, I could feel his bollocks against me, he was right up me. And Terry arched his back to make sure his full length was right inside my pussy too.

“Oh fuck yes, you are so wonderfully tight. I fucking love tight young ass,” said Phil as his whole body started to press against my back.

I really was stuffed full of cock now and thought I might break apart. I knew I was well beyond being able to spit out a sentence.

“Awwww….ooooooo….f.f.f.f.ff.f.f.ff.f.uck…..” was about the best I could articulate as I let my mouth slip onto Terry’s and shoved my tongue into his mouth.

Both men were fucking me now as I gripped onto Terry for dear life. Their rhythm was amazing, I didn’t just feel doubly done with each pump, I felt utterly and totally fucked.

“Oh yes, you take cock well, you beautiful whore,” Phil shouted as he picked up the pace in my asshole.

That was enough to push me over the edge. I started to feel a huge orgasm build up and the ripples begin.

I unlocked my mouth from Terry’s. “Oh fuck…fuck..fuck…fuck…I’m cumming,” I yelped.

“Good girl, good girl, fucking take it,” groaned Phil as he continued to plough my arse.

I did my very best to bounce up and down on Terry, but I could hardly move. I looked him in the eyes, and I could tell he was on the verge of spunking.

My orgasm hit me, and my body went into spasm. “Yessssssssssss…..awwww God yes.” Well, I think that’s what I said, but I was closer to miaowing by this point.

I could see Terry’s face tighten up, and felt his dick start to twitch in my pussy. He was a millisecond away from bursting into my cunt.

I just about managed to spit out a sentence: “Fucking spunk in me, Terry, shoot your load. SPUNK IN ME!”

He let out a loud growl and groan and I started to feel his cum fire into me.

Phil was showing no mercy, he was going even faster as he’d seen me cum loudly and his mate shoot his load right up me. Phil was also beyond words now, just grunting and groaning as he banged my tight young arse. I expected to feel his jizz fire up me at any second.

Then he screamed “Open your mouth, bitch, eat my cum!”

He was out of my backside and into my mouth in a flash. As soon as my lips locked round his monster cock he started to fire. I was expecting a hot mouthful, but his first couple of jets must have missed my tongue and simply hit my tonsils.

The next spurt flooded into my eager mouth and then his dick twitched a couple of more times, with a good bit more cum dumping between my lips.

I swallowed it all down in a single gulp. My limp, worked-over body just collapsed onto Terry.

“Fuck, that was amazing, thank you so much, guys,” I whimpered, “I just hope to hell I never have to explain this to my boyfriend!”

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