I knocked on the apartment door, honestly surprised at how nice the block Chloe and her partner lived in - they even had a concierge who'd given me a professional once over before directing me to the elevators and confirming the floor I needed from memory.
As I pushed the button for the suggested floor, I let out a low whistle of appreciation at just how swanky the complex was - clearly, there was money in the pornography business, and not just the kind of money that would help a broke-ass student buy a better quality of ramen noodles.
****
I’d taken Stuart Mosely up on his job offer, of course I had; how could I not? He was offering 6 months' pay for 6 days of work, and that was in addition to the £500 Pounds - stuffed in my trousers, right next to my semi-hard cock - I'd received as compensation for attending the interview.
Yes, I was going to be shooting porn - had agreed to allow myself to be dominated and humiliated on camera - but Stuart's rationale, that no one paid attention to the guys, rang true with my personal experience and, again, as Stuart had pointed out, it boiled down to what I could live with.
I decided that I could live with the potential for future embarrassment before I'd even made my way home from the interview - that trip, with my cock still bulging in my jeans, was a likely indication of what was to come - and now that I'd seen Chloe's apartment and the level luxury she was able to afford, I was more certain than ever that I'd made the right choice.
With that decision well and truly made, my nerves resettled in a different form: Performance anxiety.
Stuart and Chloe had been complimentary about my penis during the interview – Chloe going further still, to use me as a flesh and blood sex toy - but the fact was that I was relatively inexperienced sexually, and it had taken only one Saturday morning crash course to highlight just how vanilla my past experience was.
It had never occurred to me that the size of my penis - its girth in particular, according to Chloe - might have put teenage girlfriends off giving me little more than the occasional handjob.
Despite what the internet - pornography warping the perception of normality, again - might suggest about the nymphomaniac nature of college-aged girls, maybe the reality was as Chloe had suggested, and there was something legitimately intimidating about a unusually thick cock.
Whatever the reason, real or imagined, I was in need of an education as to what was expected of me, and that was why I found myself in the elevator of a high-end apartment block on a Friday night.
****
My phone had rung with a withheld number, which I'd usually have ignored, on the assumption that it was a scam of one sort or another, but I decided to pick this call up; the courier had left with the signed legal pack for Olympic Productions was not long, so it could be something to do with work, and when the boss calls you have to answer.
"Hello, Steve speaking," I answered, more than half expecting the voice of a deposed African Prince offering me half of his fortune if I would just be kind enough to share my bank details with him first.
"Steve, it's Chloe, I'm not disturbing you, am I?"
“No, it’s cool, I was just...” well, I'd just stepped out of the shower.
Chloe released one of her now familiar laughs, "You're either naked or wanking, which is it?"
I was momentarily shocked - how could she know - but I tried to play along, "Can't it be both?"
"You're far too unimaginative for that," Chloe chided me with mock seriousness. "Do you need a minute to finish up, or are you just out of the shower?"
"The shower," I admitted.
"Knew it," she laughed again. "Anyway - I was just giving a call; we've your contract and the NDA here, so you're in and on the books now; Stuart's in America for the rest of the week, working on the other end of the shoot - the actresses - but he'll be back Monday / Tuesday and will give you a bell then; is that cool for you?"
"Yes, that's cool," I answered, involuntarily mirroring her usage.
"Great, so you're free this weekend?" Chloe asked.
"I've a match Sunday," I said, pausing as I tried to remember if I'd agreed to anything else, "....I think..."
"Steve, let me stop you there," Chloe interrupted. "I really enjoy your self-conscious, nice-guy act because I know it isn't an act, and that makes you a genuinely nice guy, which is a rare thing in our business."
Our business... no use denying that now, I was signed up and all the way in.
"So, I'm asking - no, I'm telling you - make yourself free Friday night; you're coming over to mine, and I'm making good on my offer to help you past your stage fright."
“I…” words initially failed me, but my cock stirred at Chloe's tone, which had implied I wasn't being given a choice. “Sure, thanks; I appreciate you offering to help.”
“Seriously, you seem like a good kid,” Chloe said, her voice softer, and while she was only 10 years older than me, such was the experience gap between us that I couldn't be offended by being described as a kid. "You just need to put yourself out there a bit more, be more self-confident, and understand that you've a cock normal guys would kill for - it's practically a weapon."
"Thanks," I said humbly, really not sure what else to say.
"Good, that's attitude," Chloe said before her voice regained its edge. "How far do you want to go Friday?"
I didn't understand the question and admitted as much, "I'm sorry?"
"What I'm trying to say, Steve, is, do you want to come over, have me strap on a cock and quietly take you in the arse, or are you up for the full rehearsal?"
"Ummm," my cock twitched in answer, but I had to ask, "Stuart mentioned Watersports?"
"Did he," Chloe said, and I got the impression this was news to her, "well, nobody is going to piss on you in my living room, but I suppose we could head down to the bin room afterwards if you like?"
"No, sorry, that's not what I meant," I meant - I don't want anyone to piss on me...
Chloe laughed, inferring god knows what, "OK, so are you up for the full experience, or do you just want to go with Strap-on lite?"
I thought about it, but what was there to think about - the contract was signed, and Chloe might even be holding a copy of it, so I answered, "I'm all in."
"Good boy, that's the right answer - right for you, right for me - I'll text you my address."
"Thanks," I answered.
I thought that was the end of the call, but Chloe spoke again and with force, "My first instruction..."
She paused, expecting some sort of response; all I could manage was, "Yes, Chloe?"
"You are not to get dressed after your shower; the minute I hang up this phone, you are going to masturbate until you orgasm; do you understand?"
"Yes, Chloe."
"You are to imagine me on my knees before you, sucking your cock, as your force your full length down my throat, choking me with your big thick cock; do you understand?"
"Yes, Chloe."
"You are to use my mouth relentlessly until you are ready to cum, and then you will force me to swallow every drop; do you understand?"
"Yes, Chloe."
"Good, very good, Steve," Chloe's voice darkened as it filled with menace. "When I hang up this phone, I will also be masturbating, but in my thoughts, it will be my cunt on your mouth, and in my fantasy, you will swallow everything I give you; do you understand?"
"Yes, Chloe," I barely managed to squeak this time.
"And so we're clear, Steve," Chloe paused for a heartbeat, just to make sure she had my full attention - likely sensing the way my cock was now straining against her words. "Only my fantasy will ever become a reality, and when I choose to place my pussy against your slut mouth, you better not disappoint me."
"Yes, Chlo..." but the line was already dead.
I stood in silence for a moment, looking down at my naked form and burgeoning erection.
My phone chimed with a text message containing the promised address and a message: put your fucking phone down, and take hold of that big cock!
I read the message back a half-dozen times and then set my phone down.
I had my instructions.
****
The door opened on Chloe's smiling face, almost at the moment my fingers touched the bell, "Right on time," she started before a snort of laughter overtook her as she caught what I was carrying.
Faltering in my motion slightly, with Chloe's laughter shattering what little confidence I managed to cobble together on the trip over, I held up the bottle of wine I'd brought, "I wasn't sure if I should bring a gift?"
"Steve, you're an absolute idiot," Chloe answered, still laughing, but her smile broadened as she took the bottle from me, "but a well-meaning one, so all is forgiven."
Chloe showed me the way in, turning away for a moment to place my gift down on a small table inside the door, which she closed behind us.
As at our first meeting outside the lecture hall, Chloe was dressed up today.
Back in heels, Chloe was about 5’9, and while her hair hadn't been straightened today, it had been tied back into pigtails, which automatically made any woman over the age of 30 wearing them look slutty, and Chloe was no exception to the rule.
Today, she was wearing a very thin white shirt that perfectly revealed the sexy black bra beneath and was only buttoned to the base of Chloe's cleavage, with the top left open to draw both the eye and imagination.
If the skirt she'd worn while fishing for talent at the university had been short, what she was dressed in tonight might best be described as very short, although that still might be understating the matter - if Chloe was to bend even slightly from the waist the cheeks of her arse would be fully visible, and were she to bend backwards, even a fraction, well... well, imagination would no longer be required.
“You like?” Chloe asked, having paused deliberately to let me check her out.
I realised I didn't feel the least bit put out at being so brazen; given what had taken place in her boss's office, there seemed little point. "I really like your pigtails."
"Of course you do," she smiled slyly, fully aware of the promise the look offered. "I'd give you another twirl, but I was serious when I told you I wouldn't be wiggling my very small bottom anywhere near your very thick cock ever again."
I tried not to blush but still felt the colour creeping into my cheeks at the memory of Chloe's first pantiless twirl - does Chloe take it in the arse? Do lesbians have anal sex with each other?? Oh my god, do they?! -And the colour radiated from my freshly shaved face.
"You look great," I added, almost redundantly, my body language was speaking louder than any words.
“It’s my karaoke costume,” Chloe explained, smiling, and I couldn't help but glance at her skirt, stunned that she might wear it in public.
My glance didn't go unnoticed. "You're wondering which karaoke bar we go to?"
Hell, yes, I was; even if we lived in downtown Tokyo, it would still be worth cruising every karaoke bar on the weekends for just the possibility of catching Chloe as she was now dressed.
I tried like hell to regain some portion of my wits and managed, "You mentioned that you went out as a group on Fridays. I'd never have guessed Karaoke, though."
“Great memory,” Chloe said, sounding genuinely impressed. "Can you guess who I'm dressed as?"
I shook my head in my wonder, my mind totally blank, to such an extent that I don't believe I could have even named a member of my family if cash was up for grabs.
"Well, we already knew that you don't get out much," Chloe said with a smile and a wink before something clicked in the atmosphere around us, and we both understood it was time to get the evening moving again.
“OK, first thing,” Chloe said, "we need to work out some sort of safe word."
"Safe word?" I repeated back, sounding obviously dumb but not embarrassed by that fact; the acknowledged reason why I'd come here tonight was that I was diving in over my head and needed to learn how to swim in the open water of what I'd signed up to do.
"Yes, it's a key part of any sort of domination play, where you're playing with personal boundaries as much anything else," Chloe explained. "So, you pick a word - and it can't be anything like 'No,' 'Stop,' 'Don't,' or anything you might need to moan as part of the game - and when anyone here's that word, they know the line in the sand has been drawn, and the game goes no further.
"Domination play is all about having fun - yes, pain can be involved, as well as humiliation and a range of more complex emotions that you might not ordinarily encounter when you're keeping your sex strictly vanilla - but we're not trying to really hurt each other."
“OK, that makes sense,” and it did; when we'd spoken on the phone, I'd said I was all in, but as with Chloe's definition of embarrassing, there was no guarantee that we were on precisely the same page.
“I usually go with a traffic light system,” Chloe suggested, and there was a definite note of care in her voice.
“You usually…” I started, but that really wasn’t the point, “OK, sounds cool.”
She nodded, taking a moment to make sure I was really listening, "OK, so - it's Green for 'go' - Orange for 'be careful' - Red for 'STOP!' - that makes sense, right?
“That makes sense,” I agreed.
“Perfect,” Chloe said with a smile. “OK, I need to pop into the living room to set things up; strip naked and wait for me here.”
“Just strip?” I replied hesitantly, conscious that I was standing just inside the front door.
Chloe's tone had been overwhelming friendly tonight, but an element of her business-like self answered my hesitation, "Steve, you've signed up to shoot a porn movie; getting naked, and staying naked in unusual and/or uncomfortable places, is something you're going to have to make your peace with pretty quickly."
I nodded, Chloe's point was fair, and I was here to receive an education; I might as well start at the beginning by stripping off in a hallway.
“While I’m gone, make sure to get your cock nice and hard.”
“My cock,” I said like a fool. "Sorry, I just mean... well, I didn’t think I’d be using it?”
“Trust me,” Chloe said, with her filthiest smile yet. “nice and hard.”
****
“Are you ready?” Chloe asked as she returned through the closed door set on the opposite end of the short hallway, making sure I didn't get a peek at what awaited me beyond.
For my part, I'd managed to strip naked, being well-versed in the process after 22 years of practice.
As for the getting hard... "For fucks sake, Steve," Chloe snapped at me, with what I hoped was mock seriousness, looking at my still semi-erect cock, “aren’t you even a bit of a pervert; what were you thinking about?"
There seemed little point in holding back, so I answered honestly, "That little flash of your arse you gave me outside the University."
An exasperated look crossed Chloe's face. "God, what are they teaching kids these days?"
The question seemed rhetorical because Chloe was surely aware that what she had planned for my evening would be illegal if it were to take place in a lecture theatre.
"Give me that," she said, swatting my hand away from my penis to replace it with her own. "Steve, I'm a lesbian who's about to sodomise you - get more creative; you should be fantasising about getting your retaliation in first."
The moment Chloe's hand touched my penis, I began to stiffen and grow, a state she immediately took advantage of as she began to masturbate the hardening shaft of my cock.
“I’m half your size," she said, standing close, aggressively looking me in the eyes as she wanked me. "You're well-muscled from years of gym training for Ruby; I know you find me attractive; don't you want to fuck me?
"You could; I could pretend that I wanted to resist, but with this big cock you'd make me squirt for you, whether I liked it or not."
I was hard now. Chloe could feel it and had even adjusted her grip on account of my increased girth, but still she wanked me harder, seemingly determined to bring me back to my fullest size which she had felt only once before.
She brought her face close enough to kiss, lowering her voice, which only made me listen all the more intently, "You're about to give me your arse, Steve, but we both know you could take mine - right here, right now - there's no way I could stop you; you could pin me against the wall and split me in half raw; I'd scream, moan, cry and curse your name; but do you know what?"
She was beating me hard now, and my orgasm was close - too close to talk - not that Chole really gave me any real chance to reply, "After you'd cum inside me, I'd beg you more; I'd bend over, push my arse out, and beg you for more... you'd own it Steve, just one load from your thick cock and no one else would be able to satisfy my arse again."
"Oh, God," I moaned as I began the final journey towards orgasm, which was Chloe's cue to release my cock, step back and giggle girlishly.
"There we go," she smiled broadly, "now you're hard."
Taking some deep breaths, I managed to say, "Chloe, I would never do that," despite the evidence being presented by my straining erection dribbling precum.
"Of course you wouldn't," she said, almost kindly. "If I didn't trust you, you wouldn't be here, but just remember that everyone is allowed to fantasise - and while you might not get off dreaming about fucking my arse, I'm allowed to."
From the table where she'd earlier deposited the wine, she handed me something - a blindfold, "Slip this over your eyes - no arguments - I trust you, you trust me, ultimately everything about this game we're playing is based on that."
I didn't hesitate or argue - I did trust Chloe - and slid the blindfold over my head to softly cover my eyes.
****
My soft eye mask blindfold snuggly in place, Chloe led me - literally by the cock - down the corridor, presumably to the door she'd disappeared behind for a couple of minutes to set things up.
I felt a slight change in the air as a door opened, and Chloe had barely pulled me a half step into the room before it erupted with the sound of women's laughs and cheers.
Pulling me forward, nearly painfully, Chloe adjusted her grip, taking my still massively erect penis by the base to wave it at the assembled group.
Laughs and catcalls followed the action: 'Holy fucking shit' 'Look at the size of it!' 'He's so fucking hard!' 'I'm going to take a picture!'
The last comment drew almost raucous laughter - take a picture - and stunned me, but given my new job, this sense of unease was something I needed to get over very quickly.
“Don’t even pretend that this isn’t turning you on,” Chloe said below the general volume, just for my ears, “I can feel your cock getting even thicker, just like it did when I rode it.”
Chloe was right, and I'd surprised myself; instead of being embarrassed by the brash attention of god knows how many women, it was turning me on and making me hard; a few rapid flicks of Chloe's wrist - which she denied me utterly - and her friends would get to watch just how hard I could ejaculate.
Apparently, what was about to take place - whatever that may be - had been discussed with the group ahead of my arrival, with the cheers and catcalls intensifying as I was led blindfolded across the room.
Coming to a standstill, Chloe asked in an undertone, "How are you feeling about all this?"
"Green," I answered her, surprising myself by not even taking a moment's hesitation.
"Good boy," Chloe almost purred at me. “There’s a table in front of you; it’s narrow, and you can bend over it, spread your legs slightly, then grip the sides to brace yourself.”
Chloe's instructions were spoken below the general hum of the room, and I followed them explicitly, discovering the table was more of a bench and my full head and shoulders would stretch comfortably over it.
I took a half step back, without comment from Chloe, to better follow my instructions, and felt my cock standing hard and proud as I bent and crouched, pushing my arse out - I'd come here for it to be fucked, and it was time to own that.
When I was in position, Chloe raised her voice to the room, “Who wants to see this slut get fucked in the arse!”
The volume of cheers was such that either Chloe's apartment had very thick walls or very accommodating neighbours - shit, they could be sitting, watching and cheering along with the rest for all I knew.
I wasn't sure what was going to happen next, but when my arse was suddenly spanked - hard - I actually moaned involuntarily, and loud enough for the group to react.
Again and again, Chloe's hand came down, creating a whip-crack sound as she struck my cheek, and everyone - everyone, as evidenced by the pulsating nature of my erection - was into it.
"Do you like this, bitch?" Chloe asked as her hand came down with even more force.
My answer, "Green," was moaned for the room here.
Bent taunt as I was, my cheeks were now burning from the force of Chloe's spanking, and it was then that I felt the cool gel being poured onto it to dribble down the crack.
The hand that had so recently been spanking me raw now was softly massaging the cooling gel into my skin, a finger collecting a large amount before it was unceremoniously pushed into my anus.
Again, I moaned—loudly—and the group reacted, although their tenor had changed somewhat to that of anticipation.
"I think he likes it," Chloe called to her audience, and they reacted to the theatre; a single woman's comment - 'My god, will you look at the size of his cock!' - rang clear through the chorus.
I'm not sure what triggered it, perhaps it was nothing more than watching my arse fingered, but a repeated chant of ‘Fuck Him!’ started up, and this time it was Chloe's laughter that I heard most clearly, as she continued to loosen me.
The catcalls as Chloe continued to prepare me: 'It's so thick!'- 'I can't believe how turned on he is!' - 'He's going to cum like a fucking hose!'
Again, a single voice stood out, the woman sounding almost questioning as she said: 'I'd love that inside me.'
Another laughed a little drunkenly, agreeing, “I’d love that up in me.”
“It’s turning you on, isn’t it?” another woman called, being even more direct.
“Yes,” I admitted loudly, a sound that turned into a moan as a second finger was slipped inside me, stretching my arse out further still.
The fingering continued, but the party atmosphere subsided a little as the anticipation of the sheer taboo scene - watching their friend fuck a man in the arse - rose in every woman present.
One woman summed up the experience for the whole group as she said quietly, “My God... she's really going to fuck him.”
Chloe decided there had been enough foreplay - if that's how you'd describe the way she'd kept me fully erect - and I felt the head of a strap-on cock being eased into a position to replace her fingers.
There was pressure, but not quite enough to enter me, and Chloe asked, "What colour?"
I was ready, more than ready, "Definitely green."
My assent given I was allowed a final moment to prepare myself before she thrust her rubber cock inside my arse.
What followed next was Chloe fulfilling her earlier promise to give me the full experience as her friends watched, their laughter now infused with something like stunned awe as she began to steadily fuck me from behind.
There was a restraint in her rhythm until she sensed I was ready for more, and then, grabbing my hips, she really slammed her cock inside deep to give me my first taste of what it was like to be really fucked.
“Oh God!” I moaned loudly, which caused a woman to call out, 'He's such a little slut!'
It burned - it hurt - but there was pure pleasure behind the pain, and it radiated through my cock as Chloe began the process of mercilessly taking what she wanted.
“You like it, bitch?” she growled, her voice nothing like I’d heard before, at a volume pitched deliberately for our audience, to which she added another whip-crack spank of my arse.
My god, I didn’t want to admit it, but it felt good—better than good, it felt great, “Yes, I like it,” grunting as another thrust bottomed out.
“Louder!” she commanded, sounding frenzied, like a completely different woman.
“YES, I LIKE IT!” and she fucked me harder still; my cock rock hard, as thick as I ever got, so hard that it was barely swinging with the motion of the repeated penetration I was receiving.
“You like it?!?”
“Yes, I LIKE IT!” I said, “IT FEELS GOOD!”
Chloe’s grip tightened on my hip, surely marking my skin, as she gave me her cock relentlessly. “You like getting fucked.”
“Yes, fuck me,” I said, my mind now in the head of my penis.
“Louder, tell them,” she instructed.
“Fuck me! Please fuck me!”
“You’re such a slut."
“I’m a slut! Fuck me! Fuck my slut arse! FUCK ME HARDER!"
I’d never been loud during sex - it had just seemed, well, unmasculine - but this new sensation of being so thoroughly used and humiliated was driving me wild; I really was loving it, and I wanted to play my part in giving the women looking on a show.
I was loud, moaning, groaning, pleading - begging - for more cock, for Chloe to thrust it deeper inside me, for Chloe to fuck me harder, for Chloe to make me cum... and I was so close; Chloe was going to push me over the edge by just fucking my arse.
"Oh my god," I moaned, knowing that I was arriving at the point of no return - that I was about to cum… but then I was literally dragged back from the edge - by my hair - as my head was yanked forward, bending me over more fully, for Chloe's lips to press against my ear and whisper, “Do you still think pegging makes you gay?”
My mind tried to rationalise it: How could Chloe’s hands be on my hips as she brutally, amazingly - awesomely - fucked my arse but also be in front of me, pulling my head down to whisper in my ear.
“Chloe?” I asked softly, the bravado of my loud moaning lost.
“Don’t worry, I’ll take my turn,” Chloe answered softly, “but I thought you’d like to be introduced to my girlfriend first - she wasn't very happy when I told her how you made me cum with your cock.”
Made Chloe cum, was not how I remembered my interview, but it wasn’t a thought I had a chance to dwell on because Chloe – the real Chloe – had straightened in front of me and brought the head of a dildo to my lips.
What I was supposed to do was obvious - although I’d never sucked a dick – and Chloe removed the element of hesitation from my mind by pushing the strap-on into my mouth, holding my head fast and making me suck on her surrogate cock.
All the while, the woman behind me – my god, was it a woman? Did it matter at this point?- continued fucking me for all they were worth.
“That’s it, fuck him harder,” Chloe said, the last word seemingly cut off by the sound of the two faces connecting in a kiss, a realisation punctuated by a brief pause in the fucking, with the dildo fully inserted, absolutely pinning me to the bench.
“Cum for me,” Chloe said, and I would have answered that I was close had her cock not been in my mouth.
The fucking resumed, the angle in me changing subtly, as a now obviously different woman started to moan hard, “Yes, yes, yes—YES!” the last word followed by a muffled scream as the full length of the strap-on was buried in my arse and a weight collapsed onto my back, trembling in orgasm against my naked skin.
“That’s it,” Chloe purred, “Good girl,” and the cheering in the room rose once again as the women in the room watched their friend orgasm.
Chloe took a step back, freeing my mouth to beg, “Please! Help me! I’m going to burst! Help me cum!"
“Should I help him cum?” Chloe asked, commanding her stage.
“Fuck that sissy,” a voice called, then another, sounding extremely flushed, “My god, I want to fuck him too. I’m so turned on.”
“You want to play too, do you?” Chloe asked the audience, and several voices answered, “Yes!”
Whoever had been behind me stood, taking their weight off my frame, as they pulled out of my arse.
I experienced a strange feeling of emptiness, but there wasn’t even a moment to marvel at the sensation because I felt a fresh squeeze of lubricant to my arse, and then Chloe – and this time it was Chloe; she made no secret of it – didn’t pause for even a moment, as she pushed her strap-on fully inside me, and began a motion as if we were rampantly fucking, which of course I was, but she fell right into her partner's motion of taking my arse.
“Who wants to watch this slut squirt?” Chloe asked, coaching her voice for the crowd and slapping my arse as she pounded it with her strap-on.
The giggling girl's laughter again took a slightly different tone; I could almost smell the anticipation, and when one raised her voice to call. “Fuck him, make that big cock cum.” It was clear that she was speaking for the group, and they all wanted it to happen.
Despite what Chloe had promised me—that she would be getting hers—it was becoming clear that she’d thought through what was happening and had taken my care into consideration.
Neither dildo that had fucked me was objectively large, although they’d initially felt it when I’d been penetrated, and before sticking it to me, the first woman had helped me relax, used a lot of lube, and had kept applying it.
Yes, it was gotten rougher, but it felt good, and the rougher she had taken me, the more I'd enjoyed it.
Chloe was now pounding her cock so hard up my arse that I grunted every time our flesh slapped together, but as my orgasm built again, I understood that Chloe’s motion was more precise than indiscriminate as it might casually seem.
Every forward thrust was hard and fast, but it was also deliberate, driving against the same point – surely my prostate - every single time, and it felt better and better and better…
I couldn’t help but moan constantly now. “Please," I whispered before embracing my humiliation to raise my voice, “Please, fuck me! Make me cum!”
“You heard him, ladies,” Chloe called, “he going to blow.”
A laughing chorus erupted but died to a hushed silence when they realised Chloe wasn’t exaggerating for the party's sake, and I was going to cum, and cum I did.
It burst from me in all directions, spraying in four hard prolonged blasts aimed only by the position of my swinging erection, as Chloe continued to mercilessly fuck me throughout my orgasm, grunting, “Take it! Take it bitch!” which in the now otherwise stunned silence of the room, betrayed her own lust – was she about to orgasm – and Chloe screamed loudly to the room, “I’m cumming!!!” as she rode my arse through our orgasms.
While I only initially blasted semen, my orgasm went on and on, my arse contracting tight around the strap-on, keeping me in free fall through the abyss of my orgasm.”
Chloe didn’t collapse on me, as her friend had during the first orgasm my arse had delivered, but she didn’t pull out either, leaving the full length of cock buried inside me, “My god, that felt good.”
“Oh really?” asked a stronger female voice, which caused Chloe to giggle girlishly.
“Oh, babe,” Chloe said, “don’t be like that; I let you go first…” and her voice died then, covered by kisses of the passionate variety.
From the silence of the room rose a subtle murmuring. Clearly, Chloe and I were the subjects under discussion.
Now that I wasn't otherwise distracted, I was able to guess that maybe six women, aside from the two who’d taken me up the arse, had witnessed and cheered on as I’d lost my virginity.
The realisation that I was naked, still hard, with a rubber cock up my arse, in a room with possibly 8 women made me feel exposed again, despite the magic of the blindfold over my eyes.
It was time to take control, but as I made a move to straighten, Chloe, who had appeared to be fully engrossed kissing her partner, placed a firm hand on my back, signalling I should remain in position.
After some hurried chat in an undertone, a fresh spate of giggles arose from the women looking on until a nervous rose above it to ask, "Can I try?" which led to a full-blown explosion of laughter.
Chloe and her partner seemingly broke their embrace, with the unnamed woman asking in a tone of mock seriousness, “I’m surprised at you, Claire; what would your husband say if he knew you were fucking another man?"
The group's laughter rose at the embarrassed tone of Claire's answer. “He’d never let me fuck him like this, so it hardly counts as another man if he's not man enough to take it first."
This subtle outburst actually drew a laugh from Chloe's partner, the first I'd heard, I think, but whether she was crediting the logic, I couldn't tell.
"That seems reasonable," Chloe said, and I could hear the smile touching the corner of her lips. "What do you think, slut? Are you ready for more?”
The question was certainly for me, and while we were playing rough, it felt right that I was consulted before the next escalation; fortunately, I was in no doubt but tried to answer with feigned acquiescence to play my part in the game, "Green."
“You’re sure," Chloe asked, playing along now for her friend's - Claire - sake as much as my own, “definitely green, not even orange?"
“Definitely green," I answered immediately.
“Bigger?” Chloe asked, and rather than elaborate on what, she twitched her hips and, by extension, the strap-on inside me.
I took a moment to consider before answering again, "Green," reasoning that if I'd come this far, what was another few inches.
The decision made, Chloe stepped back, fully withdrawing from me and allowing me to experience the sensation of a gaping arse for the first time.
“God damn, that’s sexy,” someone, possibly Chloe's partner, said, even as I felt something pushed into my anus.
“It’s a butt plug,” Chloe explained. "Just while Claire gets ready. Stay bent like that, though, and keep your fucking mouth shut.
“You’ll have to take your jeans off” - laughter - “and your panties” - laughter - “because this end goes inside you” - laughter - “they’re not all like this” - laughter - “because it helps you cum” - laughter - “yes, the big end goes in him; he gets to take it like a like man.”
While this conversation went on between Claire, Chloe and her partner, I stayed silent as instructed until I was asked, "Bigger, as you sure?"
The question surprised me a little because Chloe had again stepped around the table to ask it close to my face, so close that I thought she might kiss me, but that didn't happen; instead, she grabbed my hair again, slapping my cheek, asking with some heat, "Green?"
“Green,” I agreed, and on that word, Chloe immediately gripped my head harder to force my mouth down, forward and roughly against a thin strip of hair, which a single, automatic flick of my tongue confirmed was her pussy.
Chloe made it absolutely clear what was expected of me, forcing my mouth full against the mound of her sex, “Eat my sweaty pussy, bitch.”
And eat it I did. I didn’t try for finesse; I just let my head and mouth be guided to lap against Chloe, licking her slit, which did taste salty from the sweat she’d worked while fucking my arse, but it made her taste all the sweeter to my current sensibilities.
I felt the butt plug eased from me carefully, causing me to moan against Chloe’s pussy, a sound that became more guttural as I felt the head of something new and bigger being pushed against my arse.
“Take it,” Chloe said aloud, muffling my moan by grinding my tongue onto her pussy, as her friend's virgin cock penetrated my only recently deflowered arse.
“I’m in,” Claire said, her voice betraying so much lust it was as though her body had really become hard to fuck me.
Pulling my mouth away from the tongue fucking she was demanding, Chloe growled, “Tell her what you want, you sissy bitch.”
I did as instructed, “Fuck my arse, Claire; fuck me like a slut!” was all I managed before Chloe forced my mouth back into position, leaving me no choice but to push my tongue deep inside her.
“He knows your name now, Claire; he’ll be coming for revenge on you with that big thick cock!" one of the watchers called, and while there was some laughter at the comment, I could feel several pairs of eyes settling on my penis, which still swung, remarkably hard after my recent orgasm.
Claire was somewhat hesitant, but the commanding voice of Chloe's partner instructed, "Do it," and the full length of the bigger strap-on was pushed in, our skin slapping together as she bottomed out, causing me to squeal into Chloe's pussy.
“Oh, my god,” Claire called out, “oh my god... oh my god...”
“Fuck him, Claire,” Chloe said breathlessly, and I recognised the signs that she was about orgasm in the moment before she filled my mouth, forcefully holding my head in place, giving me no choice but to swallow the wetness of her pussy as she came on my mouth.
As Chloe came on my face hard, Claire began fucking me with her cock, taking guided instruction from Chloe’s partner, who sounded decidedly husky and turned on, standing somewhere behind me.
While it was her first time taking a man, Claire naturally fell into a rhythm, no doubt mimicking how she'd been fucked from behind in the past, all the while grunting, moaning, calling me names, this time copying the behaviour she’d seen from the preceding women, “You like that, bitch! How do you like it in the arse for a change! You like it, don’t you! You like my cock, don’t you!”
And I did; I fucking loved it - regaining her breath, Chloe demanded, “Tell her how much you love it.”
“I love it!” I said, my voice raised for the room, “Fuck me, Claire; fuck me harder!”
“Yes, yes, yes,” she grunted, giving me her cock. "Fucking take it!"
“Fuck this,” one of the watchers said, her voice slightly slurred from either alcohol or sheer emotion.
Another watcher sounded shocked. “You can’t just masturbate here.”
“Watch me, I don't give a fuck,” was the blunt response. “Are you seeing what Claire is doing; look at the size of his fucking cock? - How is this not turning you on?!"
Another watcher clearly agreed - one who waxed her pussy - and showed it by taking Chloe’s place, dropping the hem of her skirt over my head, to forcefully grind my tongue up and down on the nub of her clit.
I could feel the adrenaline in the hands that held my head through the material of her skirt and sensed that the woman had arrived in front of me ready to orgasm but was determined to do so by fucking my face.
The sensations - both emotional and physical - were too much, and I realised something. "Oh my god, I think I’m going to cum again," I moaned, my voice muffled.
Claire wasn’t working with the finesse with which Chloe had taken me, but the sex was more animalistic and raw.
“Yes, cum for me, you little slut,” Claire demanded, and I ejaculated, not as voluminous as my first orgasm but just as hard, with my cock straining over and over, cum spraying from the head.
“Oh my god,” I heard moaned softly by one of the watchers - perhaps from the woman who’d so boldly declared she didn’t give a fuck if her friends watched her masturbate - as she made herself orgasm at the sight of my ejaculation.
Claire hesitated, mid-stroke, sensing that my orgasm had run its course. “I didn’t cum,” she almost pleaded breathlessly.
“No, you don’t stop,” Chloe instructed forcefully, which immediately triggered Claire back to action. “Fuck him until you cum; that's what he's here for.”
Claire needed no further invitation and let loose with lust-fueled fury.
At my face, the woman with the bald pussy used me until she orgasmed, only for her to step away and be replaced by another partygoer.
This new woman wasn't as confident and ran a soft hand through my hair, almost hesitantly asking, “Do you mind?”
I had no clue who stood over me, but she was obviously nervous about using my mouth. I could smell the gentle scent of her pussy and quested with my tongue, signalling what I wanted, until she positioned her slit before me so I could start licking.
Claire, oblivious of her friend's hesitation, fucked me until she came, announcing it loudly to a room of lusty murmurs – the giggles from earlier in the evening had now been replaced utterly by something much more serious and sensuous - and I was left to wonder at just how many women were now watching the show and masturbating.
No sooner had Claire orgasmed than she stepped away—was almost pulled away—and I sensed another woman step up behind me, pour lube generously all over my arse, and thrust into me to begin the cycle again.
Over the course of the next hour – and I felt every inch of the hour – the women behind me changed places 4 times, a number easy to keep track of because I keenly felt each initial penetration – especially when the larger of the tree dildos was used – but whether every woman at the party took a turn, or some lined up for seconds, I had no way of telling.
Three more women stood in front of my face while my arse was ridden, and not one of them stepped away until before she came.
The middle of the trio - perhaps deciding that I'd not been degraded enough - actually took a half step back, finishing herself with fingers so she could forcefully squirt on my face, a sight which clearly turned her on all the more, and she aggressively moaned through the clenched teeth of her orgasm, “Take it, you slut!”
I lost track of whether the women fucking me managed to orgasm, but when I was brought off to cum for a third time – my hard cock now dry-heaving over and over - Chloe took the softening of my penis, which incredibly had remained hard to that point, as signal an end to my humiliation.
Standing again, I realised how stiff I’d become from being bent over for so long and winced at the soreness in my arse before a smile washed over my face - I had been a very bad boy.
I paused, almost wanting to thank the ladies before leaving, but the room was awash with contented, perhaps even embarrassed silence and leaving without a word seemed to be the right approach, so I allowed Chloe to lead me silently from the living, again by my cock, to the real world and were my clothes awaited.
In the hall, Chloe took the eye mask away and said, “Things got a little crazy, right?.”
I smiled, my eyes adjusting to the light—Chloe looked exactly as she had an hour before, except now she was bottomless, with a rubber cock strapped around her waist and had obviously been sweating from her exertions.
“That might be the best night of my life,” I answered, surprising myself with the truth of the statement.
Chloe grabbed the cheek of my arse with a squeeze, causing me to wince a little. "Something to remember us by."
“Don’t worry about work,” she said, and it took me a moment to remember that I’d come here worried about shooting a porn movie, which was why Chloe had set this night up. “You’re ready for whatever they throw at you.”
****
I was in the elevator back down to street level before I realised I should have cleaned up in Chloe's bathroom - not that I'd been offered the opportunity.
Sore and sweaty all over, I must have been a sight, and with that, I desperately needed to piss and probably should brush my teeth and wash the taste of pussy from my mouth.
My phone beeped as I thanked the doorman while leaving. I’d been added to a WhatsApp group, and in the next few minutes, videos and pictures began appearing, posted by private numbers.
Clicking into the first one… it was a close-up of a woman standing inches from my head and squirting in my face.
The next... a video taken point-of-view by one of the women who’d ridden me, the camera shaking unsteadily with the motion of her body as she fucked me.
The videos/images kept appearing from all sorts of angles, and I had to stop checking my phone for fear someone would look over my shoulder as I made my way home and raise a serious objection.
Another new message appeared, separate from the group, this time from a single number:
Chloe gave me your number—I asked for it.
She mentioned that as part of your ‘job’, you were going to be fucking a woman in the arse, and it’ll be your first time.
While I was fucking you tonight, I got kind of obsessed with your cock. I've never seen one so big, and what it would feel like if the situation was reserved—honestly, fucking you is one of the hottest things I’ve ever done.
My husband stays up in the city Tuesday/Wednesday nights working—if you ever want to come over for some ‘anal only’ exchange, I’d love to be your first time.
An arse for an arse?
You have my number. Claire.
I had to drop my hand to my lap to cover the stiffening of my penis as I read the message back a half dozen times.
It wasn’t until I was halfway home that I realised I had no clue what Claire looked like.
[End of Part Two]
