by Ellis, Livia
I return to ignoring The Matchmaker. I’m hard. Olga is squirming. I ask her one simple question: Does she want me to make her cum with my cock or my mouth? She’s the client. The choice is hers. The look on her face tells me she appreciates my consideration.
The Matchmaker answers for her. She doesn’t care. She has a meeting in fifteen minutes. So hurry it up.
One of the condoms is opened with a rip by my teeth. I slide it on myself. I can hardly expect a woman that is paying me to fuck her to put the condom on for me. This is a service business. I reposition myself between Olga legs. Mentally I’ve developed an action plan that includes a fair amount of fingering, a touch of ass play, maybe a bit of tonguing, and then I’ll penetrate her.
Olga wraps her legs around me, slides under me, grabs my cock, and pulls me into her. Her legs are freakishly strong. My plan to slowly ease my cock into her has been tossed aside for a more aggressive approach. But again, the customer is always right. If this is what she wants, then I’ll give it to her.
With speed and determination, I fuck her hard. She spreads her legs wide and brings them up and around my back. I’m deeper in her than I’ve ever been in a woman. My hips swivel and buck. Her cunt muscles grab me hard and hold me tight. When I’m deeply seated inside of her, she wraps those muscular thighs around me and flips me to my back. Her thighs straddle my body as she leans back and rides me. My thumb finds her clitoris hiding inside the nest of black hair. With a feather touch, I press the pad of my thumb just against the sensitive mound. She’s moving as she likes. I don’t want to over stimulate her.
Her hips begin to swivel rather than slide. I know I’m going to cum, but I need her to get there first. My free hand reaches for one of her breasts. I squeeze and toy with the nipple until its puckered and erect. I do the same to the other. My thumb on her clit begins to massage and press just a touch more. I can see in her face how close she is. Her lips open and a sweet sound comes out. Sort of a sigh and a cry. Beautiful and musical. She grinds down on my thumb. I pull her to me and flip her on her back. I finish the job with her under me making that pretty noise.
I keep thrusting as she’s recovering. She’s whispering to me. Encouraging me. My orgasm fills my entire body, then concentrates into one ball of fire, and shoots to my penis and out as I ejaculate. I pump her over again as I spend myself in the condom inside of her. When I’m done I kiss her. This is instinct taking over. I fuck a girl. I kiss her when I’m done. It’s the gentlemanly thing to do. As previously stated, I am not a monster. Besides, Olga is far better than anyone as broke as I am could ever hope to pull. Kissing her is my way of saying thank you for lowering yourself darling.
Good, The Matchmaker says. The kiss at the end is nice. Olga?
She pushes me off of her and I flop back on the bed. I watch as she rises. I had a feeling she was tall, but I really had no idea. She’s all leg. My performance is discussed in detail as Olga slips into a pair of lacy panties and a matching bra. Now they use English. The bottom line: I’m good. I could know my own body a bit better. A bit of ab work wouldn’t kill me. Not that I’m tubby, I could just use some definition.
I look at my stomach. They’re on drugs. There’s nothing wrong with my abs. Now I’m paranoid. I’m going to have to start doing more sit-ups. Maybe work on my core a little. At least my shoulders and arms get a pass. Being picked apart is humiliating. Best I get used to it quickly.
The Matchmaker stands over the bed and looks at me. Her eyes scan me top to bottom and back up again. Work on the abs. The rest is good. Do I have a place to stay in London?
No. Not really. At least not without apologizing to Elon for being an ass.
Olga will take me to the house. There’s an empty room there. It’s mine until the Japan trip is over. We’ll see how it goes then. If everyone is happy, she’ll have more work for me than I can handle. Her phone buzzes. She needs to take it. I’m left alone with Olga.
Olga tells me to dress. She’ll take me to the house and introduce me to the girls. She leaves the room.
I find the bathroom. I turn the tap on and let the hot water run until steam rises from the bowl. I take off the condom and drop it into the hot water. The last thing I need is a bastard. When I’m certain my swimmers are dead, I wrap the used condom in tissue and drop it in the trash.
I give myself a really good look in the mirror. Do I really want to do this? As much as it annoys me that he might be right, Elon has a point. I’m not a prig, but I do tend to think of myself in a certain way that isn’t always wholly humble. I have a feeling this is one of those paths that if I go down it, it’s hard to take a new direction. I wait for a sign. There is no sign. No last moment call on my mobile as a signal there is another way. No burst of sunlight through the overcast London sky. There is nothing to stop me other than myself. I’m not going to do that.
I’ve really got nothing left. I have £700 to my name, the castle which has been in my family for five hundred years, and a couple of aging servants that I haven’t paid in about five months. Mr. & Mrs. Gresham’s compensation is enjoying their retirement in my castle. Besides, they have more money than I do. I need the job. I owe Mr. & Mrs. Gresham £2000. They’ve been very nice about not reminding me, which makes me feel worse.
I give myself a final look in the mirror. I have no one left in my life other than Elon and Mr. & Mrs. Gresham to disappoint. What family I have, has taken to not acknowledging my existence. I’ve been banished from the family that I’m supposedly the head of by virtue of the fact my father was the oldest of his brothers and I was his only offspring. The title and the castle are mine.
My uncle, the one in search of a hit-man capable of making my death look like a tragic accident so he can take my title and my castle, called me a profound disappointment. Several times. Loudly. In public and in front of witnesses. Witnesses with camera phones and internet connections. I was nearly as popular as the finger biting Charlie for a day.
My uncle, the one out for vengeance, isn’t wholly wrong. Truly, what a disappointment I’ve been. With the defection of my uncles, and the refusal of most of my cousins to acknowledge my existence, I have no family. More or less. I’m peevish so I’m using hyperbole to be a brat. My father’s family has disowned me. I have a mother roaming out there in the world somewhere. India I think. At least that’s where she was the last time I got an email from her. There was something about a raja that had taken a fancy to her. I had no idea there were rajas anymore.
As I stare at myself in the mirror. There is a momentary and fleeting fear that I am going to become my mother. I don’t know that she’d ever think of herself as an escort, but she certainly fucks for a living. Unfortunately for her, she’s getting older and plastic surgery is expensive. I’m still young. I’m going to do this. I’m going to do it well. I’m going to make some money. I’m going to prove to Elon that I do in fact have the stones to do the job. I’m going to find someone to marry. Someone with a lot of money. Then I may never fuck again. But I probably will.
21
5 Voyeur
When I’m dressed I leave the room and go searching for Olga, The Matchmaker, or anyone. I’m not certain where I’m supposed to go, but the sounds coming from a bedroom down the hall draw me. I have a very good idea what The Matchmaker’s appointment was. That cool, placid, exterior wasn’t as unaffected by what she witnessed happening between Olga and I as I thought. I know what sex sounds like. Someone nearby is engaging in coitus.
I creep down the hall with a large grin on my face. A deep sigh stops me. I press my ear to the door. There is definitely sex of the female on female variety occurring on the other side. I truly never thought of myself as a voyeur, but then again I never thought I’d be paid for sex. The doors in the house are large wooden planks fitted with brass knobs and plates. In each brass plate is a keyhole. Just the sort of thing maids used to use to spy on the occupants of the rooms. Perfect for this fledgling voyeur.
In the room are two women. One I know
. The Matchmaker. The other I don’t, but I wouldn’t mind getting to know her. There is a soft spot in my heart for red heads. Especially ones that have a full and glorious bush of fiery hair. I’m wondering if there is some secret underground of men that truly understand how delightful a woman as nature intended her to be is. Or is it just these women are confident enough, know their bodies well enough, not to feel pressured by trends? Either way, I’m a fan.
The Redhead with enormous tits stands with her back to one of the columns of the four poster bed that dominates my visual field. Her arms wrap behind her body, holding tight to the column. That pair of well rounded, generously endowed breasts thrust forward. Burying my face between the set as I give them a good fondle and squeeze is added to my list of things to do before I die. A pair of creamy white legs encased in a pair of shiny, black, thigh high boots is spread wide. Between those legs, The Matchmaker is enjoying a feast.
The well-tailored black dress The Matchmaker had worn for my interview has been discarded. Her hair has been removed from the crown of braids and allowed to hang down her back. She’s also quite flexible. Squatting low, with her legs spread wide; the way her arms move tells me her hands are busy with her own cunt. For a woman of undetermined age, she has a marvelous arse. The blood rushes to my cock for the third time in just as many hours. I’m going to need to increase my cardio. Otherwise I might have a heart attack if I have to keep up this pace.
My hand slips into my trousers as The Matchmaker rises to her feet. The Redhead drops her arms around The Matchmaker’s shoulders. Their mouths come together in a long, sloppy kiss that included a lot of tongue swirling and licking. They turn just enough for me to discover The Matchmaker prefers a clean mound. As they kiss their pussies rub and bump together. Their hands slide down the others back until each has a double handful of perfect rump. The sounds of moaning and sighing increase as they press together.
I nearly protest when they pull apart. But when they climb on the bed, I nearly cheer in approval. My hand was rubbing against my hard cock, the tip receiving special attention from my thumb. The Matchmaker lies on her back as The Redhead slides like a snake on top of her. I know what tribbing is, but I’ve never actually seen it happen. As the two come together, they’re turned just enough for me to have a view of their vulvae as they begin to bump together. The matchmaker releases a deep sigh as The Redhead brings their mouths together. I nearly cum when they start pinching and squeezing each other’s breasts. Their wet cunts start grinding together. The Redhead’s round, white ass, shimmies and bobs as she works The Matchmaker towards release.
There is only so much I can see from my place at the keyhole, but I can see enough to know that the two are reaching their climax. Then they stop. I desperately want to walk into that room and tell the two of them enough of the teasing – just get on with it! But I’m not going to do that. I don’t want to give The Matchmaker a reason to fire me and I’m enjoying watching the two fuck from my place behind the door. Who would have thought I’d learn something new about my own sexuality? I like to watch.
The Redhead rises from the bed and goes to the nightstand. From it she pulls a long, slim dildo, and a tube of lube. As she returns to the bed, The Matchmaker flips over and rises up on to all fours. Her legs are spread wide and her ass is pressed up in the air as she brings her face down to the mattress. My breath catches in my throat as The Redhead coats the dildo with a generous serving of lube. I nearly ejaculate in my hand as The Redhead bend over just enough to run her outstretched tongue over the rim The Matchmakers anus. The Matchmaker cries out as she presses her ass to The Redhead’s wiggling tongue.
I’m going to cum and I know it as I’m watching the two. A finger sharply poking my shoulder brings me as close to a heart attack as I’ve ever been. I nearly yank off my penis as I pull my hand from inside my trousers. I’ve been caught in the act by a very smug looking Olga. At least I didn’t scream like a girl, but I did make some sound. There’s movement in the bedroom. I can hear the two talking. Olga offers me her hand. I jump to my feet and the two of us bolt around the corner. The door to the bedroom opens for a moment, and then closes again.
I look down at Olga. Her hair hasn’t changed. Still that whip of a ponytail I’d be happy to have her beat me with anytime. She’s wearing a dress. I like women that wear dresses. It’s just so pretty and feminine. Women’s’ fashions aren’t my thing, but I can tell it’s expensive. It looks expensive. Expensive and classy. The silk is thick and gunmetal gray. Very sexy. Olga doesn’t look like a whore. Not even a little. This is probably why she can charge what she does.
She looks up at me and mouths the word naughty. I am naughty. I’m also very hard and very close to cumming in my trousers. I let her know I need a moment to myself. She just gives me that grin and leans in to me. I think she’s going to kiss me, but instead she grabs the knob on the door behind me, gives it a turn and a push. Voila: A bathroom.
Instead of letting me alone, she walks in to the white tiled, pristine bath behind me. The door is closed and locked. The fact that I’m a naughty boy is repeated. The Redhead is not one of the girls. She’s The Matchmaker’s girlfriend. No she’s not a madam. She’s a party planner.
Her hands unbutton and push open my trousers as she’s telling me all of this. When her fingers wrap around me and squeeze, I groan. I look down at my cock with her hand wrapped around it as she starts to masturbate me. She holds me hard and jerks me fast. Her fingers are a blur. I was already nearly there before she touched me, so it doesn’t take much. Her mouth clamping on my neck as her tongue draws a small circle on my skin does it.
My third orgasm of the afternoon is like a cannon shot out of my cock. Olga quickly steps to the side, some admonishment about not messing her dress left hanging in the air. Lovely as it is, at that moment I could really care less about her dress.
She walks past me to the sink. She washes her hands and looks at me through the reflection in the glass. Am I ready to go to The House and meet the girls?
Absolutely.
25