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Middle Man

"True tales of a retired courtesan."

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Author's Notes

"Another installment of stories from my life as an escort, this one about MFM, MMF, and assorted variations. Thanks to the people who commented on "The Unicorn"! “MMF: A threesome involving two men and one woman. <p> [ADVERT] </p>There are several options for who actually has sex with whom: (1) the woman in the middle; (2) one of the men in the middle; (3) everyone has sex with both the others.” - The Urban Dictionary"

Much as I respect the wit and wisdom of the Urban Dictionary, there are actually a few more variations than that, which I’ll get into. The MMF (or, as it’s generally written if its option number one above, MFM) was not something I encountered too much when I was first starting out escorting as a young woman. But in the last five or six years of my work, it became very, very common…

I don’t know if it’s because Maxine was specifically putting me up for these jobs or if the practice itself had become more common with American men. It’s very possible that the latter is true, because I think increasingly people have been exposed to all sorts of variations of couplings that they see on internet porn, and certain things spark their fancies and they want to try them for themselves.

MMF falls into the category (probably, I wouldn’t really know) that a wife or girlfriend might not go for, so a pro is needed. Part of the reason is probably that no matter what anyone says, there is a certain homoerotic aspect to sex of this kind, and that is something that many men really want to keep private and secret.

To talk about this part of my career, I think I need to tell a few different stories to give you an idea of the variations on this theme.

I don’t remember now if Vince and Brian were my first MMF experience, but if not, they were certainly one of the early ones. These guys were buddies who, I think, were gym rats and knew each other from regular workouts at Gold’s Gym here in Venice. They were in their thirties, and their daily workouts were paying off - they were both in great shape, and quite handsome.

They were well-dressed professionals of some sort, but I don’t know what kind. I’m guessing that they had taken quite a few showers together at Gold’s. Perhaps that’s how the idea of being together in a threesome arose (so to speak). My guess it was Vince’s idea, because he was somebody Maxine knew as a regular Rites of Eros customer, and, during the act itself, he was definitely to take on the alpha role.

We met at the bar of a nice hotel in Santa Monica. They were, as I say, both well (expensively) dressed and handsome. This will be easy! I remember thinking. Neither one wore a wedding ring, but I could see a bit of skin whiter than the rest of the finger where Brian’s ring normally was. (Why he felt compelled to take it off for my sake I have no idea. But quite a few men do.) They made room for me to sit between them in a dark booth, then got back in, having arranged us so we were all on the same side, with me squarely in the middle.

We made some inane small talk for a few minutes, but I could tell there wasn’t going to be much of that. I was wearing a short skirt, and Vince put his hand on my thigh and started nuzzling my neck. Brian seized on the other thigh. I remember wondering if he was going to nuzzle me at the same time, telegraphing to everyone in the bar what we had going on here. But he was too discreet, or shy, or something. They seemed alright, so I was good to go upstairs with them.

We were the only three people on the elevator, and Vince wasted no time planting a big kiss on me and groping my ass. A lot of sex workers don’t like to kiss their customers, but I’ve always found that a little funny given that we invariably end up sooner or later with their penises in our mouths. I don’t mind if the gentleman is gentle about it and doesn’t have a bad case of halitosis or whatever.

But before the elevator shuddered to a stop on their floor, Vince had taken Brian’s hand and placed it on my other ass cheek. See what I mean about him being the alpha? But Brian seemed willing enough to comply.

They seemed in a big hurry to get on with it, which, of course, was fine by me. They had cut a deal with Maxine that they would pay my full one night rate, but get me for just half that time, since there were two of them. Makes sense, right? So they had me for four hours, which would have meant to some that they could go slow and savor the experience. But not these two, or not Vince anyway. I had failed to captivate them with my scintillating conversation. I guess, and by then I had a pretty clear idea it wasn’t my brain they were interested in.

They got me naked in no time at all, four hands and two mouths all over me as they were tugging away my clothes. It was a little odd when both of them latched onto my breasts and suckled as if they were hungry newborn twins. That can be quite a tender part of lovemaking, but to these two, it seemed more of a predatory act. Tit vampires, if you will. Brian kept at it while Vince struggled out of his clothes. Then Vince took over while Brian took his off. I noticed they were both very erect, so whatever was happening in the room was working for them.

We ended up in a heap on the bed with me pretty much the object of attention, their hands all over me, their mouths. Each of them had a go at my girl downstairs. Brian, I remember, was particularly good at it. It was not unpleasant to be the object of that much male energy and passion and excitement, and I thought again that this would not be a difficult assignment. I noticed that the two men seemed to go out of their way to avoid touching each other even as they were all over me. I wasn’t sure what to make of that.

A favorite for both of them seemed to be something I have since learned is charmingly called “spit-roasting,” which meant that I was on all fours with Brian’s cock in my mouth while Vince was fucking me from astern. Get it? Spit-roasting? And then they swapped. I figured out early on that the fucker drove the rhythm of my bj. It didn’t feel particularly unnatural once I got used to the sensation of penises at both ends of me.

I could tell by a change in his breathing and a tightening of his balls that Vince was about to cum. I don’t particularly like to swallow semen, so I pulled him out of my mouth and he ejaculated noisily, his cum shooting over my shoulder and onto my back. This was, of course, in full view of Brian. True to form, the sight of a cum shot turned him on, and I felt and heard him cumming inside me in his condom immediately afterwards.

I thought perhaps they would be done with me then, but we’d used up a bare hour of their time, so the three of us kicked back on the bed and finally had a bit of conversation. Brian seemed subdued, but Vince was garrulous and dominated the talk. I don’t much remember exactly what he said, but I recall that sports was a big deal to him, and there was a lot of boasting about his prowess at basketball.

That irritated me a bit (I’m not too keen on braggarts) and I’m not proud to relate that I mentioned that a couple of the Los Angeles Lakers were regular clients of mine. That shut him up about his athleticism. That was a terrible thing to do from a good courtesan’s point of view, but this was fairly early in my career, and I tended to have a lack of patience for certain kinds of men in those days.

It was Brian who came to life first. We hadn’t gotten dressed after round one, so he just started stroking and kissing my body again. At one point they were on their feet as I was sitting on the bed. I could see both of them would need some oral stimulation to get their hard-ons back, and I’m quite sure they had arranged themselves so I could get at both of them. And so I took a cock in each hand, pulled the two men closer to me (and each other of course) and took turns taking each one in my mouth, one at a time, continuing to stroke both.

I’d had an instinct or a hunch all evening, and I decided to put it to the test. It was something I had seen in porn, but hadn’t ever tried myself. Having each lad firmly in hand I pulled them closer and closer so that the tips of their cocks were nearly touching. I didn’t want to freak them out, but was fairly sure I would not, that in fact that this is what they wanted.

I had the tip of Brian’s cock in my mouth, and, without making too much of it, I crammed the tip of Vince’s in there too, so that both heads were pressed together inside my mouth. My hunch was right. They both gave ecstatic moans and their cocks became rock hard.

Then they took turns fucking me some more while the other looked on and fondled me or himself. Inevitably (I suppose) Vince asked me if I would like to be DP’d, or double penetrated. The truth is, as I’ve said elsewhere, I am not all that fond of anal sex. I’ve done it plenty of times, but I prefer men who are not at all well-endowed, and, as I’ve said, Vince and Brian both had plenty. So I explained all this to the lads, but I did it with the offering that, if they were willing, we might try DVP, or double vaginal penetration.

I was not at all sure we could work this out logistically, but I had had a few truly humongous cocks in there by this time (see my earlier remark about guys from the Lakers), and I thought with enough lube we might be able to manage it. Besides, that particular orifice can squeeze out a ten-pound baby, so it’s pretty elastic.

This act, of course, puts the men in an incredibly intimate proximity to each other, but my double bj had been so successful I didn’t think they would object to that too much.

We did manage to do it. I didn’t know too much about this act at the time (I learned a lot more in the years to come), but it works best if both guys are about the same size. The man on the bottom has to be able to sustain an erection while being fairly powerless to move (not all that easy, as I’ve observed), and the one on top has to be able to keep his weight off of both the lady and the bottom man. After a few failed attempts we figured this out, with Brian on the edge of the bed, me impaled firmly on him sitting up in what’s called a reverse cowgirl, and Vince standing on the floor and pressing himself in.

They both came very quickly. I think they liked it. I was pretty certain they would.

Urban Dictionary’s number two is my most common scenario. Generally, it goes something like this: my typical client is an older man, married invariably, who is either closeted gay or deeply curious. He wants a homosexual experience, but he wants nothing to do with the gay lifestyle or identity, he just wants to try new things sexually, and he feels better about the whole thing if there is a woman someplace in the mix.

I’ll tell you about Harold, a client who became a pretty good friend. He’s not exactly typical, but I like him a lot and enjoy talking about him and remembering some pretty good times. He was a retired CEO of some sort, always affable, generous to a fault, and always extremely grateful for whatever I could arrange for him. He left the choice of the second man up to me, and I drew on gay or bi friends I knew.

Harold was willing to pay for that guy’s services too, but I generally preferred to bring someone I knew would just be into the experience for its own sake. Harold always hosted these parties at the luxurious Beverly Hills Hotel (the pink palace on Sunset Boulevard owned by the Sultan of Brunei), and most of my friends didn’t get to spend time in places like that, so that was payment enough for the likes of Jimmy and Slade and Cole (who was maybe the love of my life, and, briefly, my husband).

I think I’ll use Slade here, as I can remember one particular time clearly. Slade and I met Harold in the famous Polo Lounge at that hotel, and Harold bought us expensive drinks and we talked about anything except sex. Harold liked my mind, and all the weird eclectic things that interest me, and I loved how he could get me to gush enthusiastically about whatever I wanted, and he would always pretend to be fascinated by every word. Eventually, we went to the room or bungalow he had rented.

Without too much ado we all three undressed, and Slade and I put Harold on his belly on the bed, and gave him a four-hand massage. He was a very large man, and there was a lot of flesh to cover. Slade, a powerful young man, straddled Harold’s ass, and gave him a deep tissue shoulder and upper back rub,

Slade’s cock pressed against Harold’s crack, and I knew Harold liked that a lot. I employed my friend Fang Xia’s soft touch and lightly tickled Harold’s inner thighs, balls and anus. Between us, we got him very excited as we saw evidence of when we rolled him over. Harold always requested that I bring a straight guy so we could “spoil” him (Harold’s word).

None of the guys I brought ever actually was entirely straight, but we never told Harold that. Next, I told Slade that I was going to feed him his very first cock, and I was going to show him how to suck it properly. “But I’m straight!” Slade protested, fairly convincingly, I thought.

“I’m afraid you have no choice,” I said. “Now put your face right next to mine and do everything just as I do.

And so I would demonstrate a lick, and Slade would follow, protesting, “But it’s so big!” (It wasn’t.) And then I’d show him how to suck and use his hand, and so we passed Harold’s very happy cock back and forth between our mouths, Slade making a pretty good show of having difficulty getting it all the way in his mouth and then loving it once he got it there.

I’m not 100% sure, but I seem to remember that the very first time I was with him, Harold fucked me, but that was positively the only time. For the most part, he was primarily interested in the middle man I brought to the party. But the fact that he had done me the one time technically puts us in the “man in the middle” category. But after Slade’s blowjob lesson we moved on to the part that Slade particularly liked, and that was for me to lie back, very visibly play with myself, and tell the two men what to do. Order them what to do, in fact.

Harold loved to think that I was turned on by watching this male homosexual activity, and I think that was some sort of justification to himself that he was still pleasing the woman in some way. It was fine, it took all the pressure off of me, and I certainly didn’t mind the sight of two males coupling, though feigning a great deal of enthusiasm for it was a bit of a stretch. Still, I think I managed.

By having me tell the boys what to do it also took away the responsibility that might have fallen on Harold to initiate things that he probably didn’t want to admit to himself that he liked… But I knew what he liked, and I made sure he got it. “Okay, Harold,” I purred, “I want you to go down on Slade. That’s it, take him in your mouth. How do you like having a man suck your cock, Slade? Good boy. You love it, don’t you? Alright guys, I want to see you sixty-nine each other, come on. Oh my god, that is so fucking hot. Yes… yes… God, you’re gonna make me cum just watching you. Okay, Harold, face down, ass up. Put your condom on, Slade, that’s a good boy. Now I want to see you fuck your first man, Slade. That’s it, lube him up.”

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You get the idea. Harold was always a “bottom,” as the parlance goes. Soon after this penetration, Harold gave a little gasp and collapsed under Slade. His orgasm. I don’t believe he ever ejaculated, probably due to an enlarged prostate or some other older male problem. But this kind of threesome always made him inordinately happy, and he usually gave the extra man and me a very handsome tip in addition to my already exorbitant fee that Maxine had negotiated and collected. All of the guys I took to Harold always liked him – he was really a very affable older gentleman, and they always told me sincerely they had a good time.

Harold would always be the first to leave, letting Slade (or whomever) and me have the room or bungalow. I usually went home, even though the place was very nice. I almost always wanted to be alone in my own cozy bed back in Venice Beach after a gig. But Slade would always stay over, and so would Cole. Both of them, I suspect, would invite friends to come over to let the party continue.

Urban Dictionary’s variation number three was not too different from Harold’s scenario, in that it involved bisexual activity between the men. It’s just that the client was a bit randier, and interested in fucking me in addition to the other guy. The clients were usually still bottoms, but from time to time one of them would prove to be a top. This was something I had to ascertain in advance, because not all of my guys – like Cole, for instance – would agree to be a bottom. He didn’t mind topping, but that was as far as he cared to go. That was okay.

My friend Jimmy was actually a bottom by preference, so I would know to call on him. The clients for option number three were usually younger guys who were just intensely interested in pushing their own limits, or finding out where they were or if they even had limits. Some of them, I was sorry to see, would show signs of shame or regret after they climaxed. I would do my best to bolster them up, but I think the homosexual acts they had just engaged in were feeling wrong to them after the sex buzz ended.

(Not that a client feeling guilty after a session was very unusual. Lots of men are affected by a certain tristesse after having had sex with someone other than their partner. This is something, by the way, that is a lot less obvious in women, as a rule. I had no good way to deal with their feelings of regret except to try to be brisk and pleasant and get dressed and out of there as soon as I could.)

The variation that I mentioned at the outset here that isn’t covered by the Urban Dictionary, was one in which the client didn’t have sex with anybody, but preferred simply to watch. These were men who wanted to play out a cuckold or voyeur fantasy, and sometimes the set up was pretty elaborate.

I’ll tell you about one that was interesting to me in that it was extremely dramatic, and it occurred in the client’s own home, something that is pretty rare with a married man (and this guy clearly was). His name was Neil, and he was a middle-aged guy with thinning hair and a paunch, and he lived in a house in the suburbs of Irvine, down in Orange County.

 

He had approached Rites of Eros with an extremely specific shopping list that went so far as to include dress and foot sizes. He was looking for someone quite petite, and it happened that I came close to the size and build he was after. Then he had picked my picture out of all the ones Maxine had shown him.

So here was the deal! He dropped off a dress and a pair of high heel shoes at the Rites of Eros office. He also dropped off a wig, a short blond pageboy. I was to put all that on (stuffing all of my very long brown hair into the wig somehow) and drive to his nice American neighborhood at an appointed time in the middle of the afternoon. My name, by the way, was to be Debbie. I was to arrive, then use my phone to call my lover, Tyrone (he had to be called Tyrone, just as I had to be Debbie), to invite him to come over. A big black guy, you understand.

Then “Tyrone” and I would repair to the master bedroom and fuck each other’s brains out while Neil emerged from hiding to watch us. I was to insult Neil mercilessly while carrying on with Tyrone. Neil would never lay a hand on either one of us.

Elaborate, right? I consulted at length with Maxine and she came up with an African American who was on her books: her go-to guy on the rare occasion when a woman called, needing a man to service her. His name was Michael, and he was an Adonis: beautifully muscled, handsome, a lovely chocolatey color, and, best of all for this scenario (as the sequel will show) incredibly well-endowed. He was also a good actor, which was clearly a skill that would be required in this little porn drama.

I met Michael for coffee on the appointed morning of the tryst, and he proved to be an extremely nice fellow. Not only that, but he was indeed an actor, trying to break into Hollywood. Being a gigolo was only one of the jobs he had to try to make ends meet in an expensive and difficult city. Male prostitutes don’t get as much work as we gals. Maybe some of the gay ones do, but this guy was arrow straight. I would have thought he would be an obvious guy to do porn, but he was trying to stay discreet in case he got his big break in legit movies. (Does anybody actually care about that anymore? I’m not sure.)

He was a graduate of USC, and very well-spoken, but we agreed that the Tyrone character would have to be a lot rougher. We devised the persona of a South L.A. gangbanger. We entertained the idea of painting some henna tattoos on him but decided that would be overkill and too much trouble anyway. We rehearsed the general outline of what we were going to do, then parted to go get into costume and character. The next time we would meet would be in Neil and Debbie’s house.

It was a lot of fun to go home and get dressed as Debbie. I had never seen myself in a short blonde wig before, and the transformation was astonishing. I really felt like someone else. And the dress and shoes were not things I would have ever picked out for myself. With a start, looking at myself in my mirror, I realized that Debbie was probably a Republican! Something I am quite adamantly not. Well, I thought, sex with Michael/Tyrone would be no problem, but I hoped Neil’s fantasy wouldn’t somehow make me say nice things about Ronald Reagan.

It’s a long drive from Venice down to Orange County on the soul-killingly ugly 405 freeway. I decided it would help me get into character if I listened to some right-wing talk radio on the way. I never said I wasn’t a whore, did I?

I parked on a suburban street in front of the innocuous, ranch-style house. I noticed there were no sidewalks in this neighborhood. You don’t walk anywhere there, you drive. The front lawn was neatly mowed and watered. Some flowers grew up against the house. Debbie must have had a green thumb. The door was unlocked. I went inside.

Yep, Republican as all get-out. Early American furniture. Wall-to-wall carpeting. Art prints that weren’t exactly Norman Rockwell, but were close. A woman’s touch everywhere I looked. If the real Debbie had left Neil, it was very recently. I decided it was much more likely that she was out of town someplace, visiting her mother or going to a realtor’s conference or something, and he’d cooked up this little drama in her absence.

I tried to move and act in character, because I was pretty sure Neil was hiding someplace, watching me. I went into the kitchen and, sure enough, there on the bulletin board were pictures of Neil and Debbie, who didn’t much resemble me except in height and the short blonde hair I was sporting. I was hoping Neil wouldn’t mind my tattoos when they were revealed… I’m fairly sure that Debbie didn’t have any. I got out my cell phone and called the number Michael had given me. He answered right away, already in full character: “Yo, baby, wassup?”

“I need you, Tyrone,” I said. “I need your big black cock inside me. I have to have it, every inch of it. Now. Please!”

From some difficult to pinpoint place – the broom closet whose door was ajar? – I heard a slight expulsion of air, a gasp. Of pain? Of pleasure? Whatever it was, I took it as a good sign.

I went into the bathroom next, leaving the door wide open. I mostly looked at myself in the mirror, striking what I hoped looked like wantonly sexual poses, unbuttoning most of the buttons on my dress, experimentally pushing my breasts up, giving myself lecherous leers, etcetera. Michael, happily, had been standing by in his car nearby. He was there in a matter of minutes. He rapped purposefully on the front door.

I let him in and he swept me up in his arms, giving me a deep tongue kiss. He had dressed the part – dangerous thug to the max. “Look here, Debbie,” he said, laying on the ebonics perfectly, “I need you nekkid, baby. I need to see that little white ass of yours. Do it!”

I kicked off the shoes and got out of the dress quickly. Michael expertly unfastened my bra with one hand, and, voila! The little twins sprang free. I was hoping Neil liked perky and didn’t mind the tattoo between them. I had taken the initiative to wear my most conservative white panties, and Tyrone yanked them down as he picked me up off the floor. I wrapped myself tightly around him, and he carried me into the bedroom and, without further ado, flung me onto the bed.

He peeled off his clothes, revealing that perfect body and a humongous cock that hung at half-mast. I took it in my mouth, and to my alarm, it kept growing and thickening until it would have been a match for Vince’s and Brian’s put together. 'Hoo boy,' my mind said to my pussy, 'good luck with this, baby girl.'

I must say it was interesting to have sex with a guy who was, essentially, in the same profession as I was. I imagine it was the way porn stars feel, working together, a kind of professional and casual camaraderie in spite of the ultimate intimacy going on between them.

I made sure to be very noisy as “Tyrone” went down on me (very expertly, I might add). “Oh god, Tyrone! Oh yes! Oh yes!” Then when he moved up to mount me, and did, I think the sounds I was making were no longer faked.

We had not been fucking long, when into the room burst Neil, wearing his best office suit, necktie, hat, and overcoat. He even carried a briefcase, the very picture of a man coming home from work unexpectedly early. “Oh my god!” he cried. “Debbie! Debbie, what are you doing?”

In for a penny in for a pound, I thought. I summoned my best Stanislavski technique. “What the fuck does it look like I’m doing, Neil?” I said. “I’m fucking my beautiful black lover.” And, turning back to Tyrone I moaned, “Fuck me, baby. Fuck me with that giant black cock of yours. Fuck me the way my limp dick husband never could.”

“Oh Debbie!” cried Neil. “How could you?”

“You set down and watch, bitch,” said Tyrone to Neil, “and Debbie will show you how she can.”

And Neil did. And I did. I was glad the dialog portion of the act seemed to be over, as I didn’t really like saying such mean things to anyone, whether he was paying for me to or not, and didn’t feel like I was very good at it. Fuck acting was a lot easier than dialog acting, at least for me.

I was mostly just paying attention to the man who was fucking me, and had sort of lost track of what Neil was up to. But I realized after a time that he had moved to the bottom of the bed and so had given himself a porn close up of Michael’s and my privates. Whatever. He deserved his money’s worth.

I had a little frisson of alarm when I realized he was down there taking pictures. Were Michael and I part of some nefarious scheme to blackmail the real Debbie? But then I knew he must have been getting pictures of my ankle tattoo along with everything else, so the match with his wife or ex or whatever the fuck she was wouldn’t have matched. I decided they were for his own private delectation later on.

Michael/Tyrone was a wonderful and athletic lover. We fucked in every position we could think of. I was riding him reverse cowgirl when I looked straight at Neil (who was still on the bed with us) as scornfully as I could. Something about my vicious sneer prompted him to take out his penis and begin masturbating. He really did seem to get off on the abuse.

Poor man, I thought. I’m so sorry. But I said it anyway: “Just look at that pitiful little pee-pee in your hand. Do you want to see what a real cock looks like?” And I bolted up off of Tyrone, exposing his tumescent manhood to Neil. I took that cock in both hands and jacked it for all I was worth. I don’t know if there was something about my technique, or if Michael was just such a consummate pro that he managed to time it so expertly, but he began to ejaculate, huge spurts, which I aimed at my tits.

“Oh god!” cried Neil and he came too.

I was not at all sure what was supposed to happen next.

After Neil shuddered to the end of his orgasm, he pulled up his pants, clapped his hat back on his head and ran away, literally, without another word. Michael and I heard the front door slam. “What the fuck just happened?” I said.

“I don’t know,” said Michael, still as Tyrone. “Some kind of weird-ass white people shit.”

And we laughed, then got dressed. I was very happy to take the wig off and let my sweaty hair out. I laid the wig and the dress on the cum-stained bed and put on a long t-shirt I had thought to bring along to get home in.

“Meet for coffee again sometime?” said Michael.

“I’d like that a lot,” I said.

“Terrific.”

He gave me a chaste little kiss on the cheek, then he left.

I left the house and looked once more at the neighborhood. I put the top down on my Porsche. Driving home, back on the dreary 405, I put on my favorite Alt-Rock FM station. I turned it up loud. I let my long brown hair flap wildly in the breeze. I felt fantastically free at that moment for some reason.

Published 
Written by serryn7
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