The Gigolo Chronicles 4 - Gloria - Cover

The Gigolo Chronicles 4 - Gloria

by Master Jonathan

Copyright© 2021 by Master Jonathan

Erotica Sex Story: Gloria is a unique client of Tony's in that she is into the BDSM scene. But Tony is anything if not versatile and whatever the client wants, he will deliver!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   MaleDom   Oral Sex   Sex Toys   Prostitution   Illustrated   .

Gloria is a young divorcee who receives a very generous alimony settlement from her ex-husband and this, plus her job as an executive secretary to the legal offices that represented her during her divorce, enables her to live quite comfortably. Her marriage was not a happy one and she has no intention of ever marrying again.

Gloria got married to a man who charmed her completely, but the honeymoon didn’t last long. As she explained it to me when we first met, it turns out her husband actually wanted a rich woman to take care of him so he didn’t have to work and could spend that energy being a ladies man – to other ladies! You see, Gloria came from money. Not Rockefeller, Carnegie, or Vanderbilt money, but her family wasn’t poor by any stretch of the imagination!

Now Alan, her ex-husband, was middle class. He came from a blue-collar, working man’s background ... his father was a construction engineer and his mother worked as a bank teller once the kids were old enough to take care of themselves after school.

When he met Gloria, Alan saw a way out of the mediocrity of being just “average”. Whether he ever really loved Gloria is a matter of debate and depends, I suppose, on who you ask. But as far as she was concerned, he only wanted her for her money and influence.

I met Gloria about five years ago, I guess. It was at a dinner party that one of my other clients and I went to. I just happened to be in town when some friends of hers decided to throw a party. She thought it might be something I would like and so we went. While we were there Gloria came up to my ladyfriend inquiring about me. She gave Gloria my contact number – the number of my answering service in Dallas and a few days after I got back home she called me. My ladyfriend had talked with her some about who I was and what “line of work” I was in. When she called me she was somewhat informed although the specifics were still a bit puzzling for her. I explained that I didn’t like going into detail about my work, for obvious reasons, but if she would like to meet me, I would be happy to talk to her about it.

She flew to Dallas a few days later and we met. She liked what I had to say and apparently my ladyfriend was a good reference and had sold her on my “product” even before we met. We ended up in her motel room that night and the rest, as they say, is history!

Gloria is a nice change of pace from most of my other ladyfriends. While most of the women I date are looking for someone to treat them the way they think they should be treated or love them in the way they don’t get from their husbands or boyfriends, Gloria is different. Gloria is into the kinkier side of sex – subjects my other girls aren’t really into (although some of them might be persuaded if they knew what they were missing!).

Her favorite sexual preference is BDSM and she loves to be tied up and “forced” to perform sexual acts or have them done to her. She likes to be degraded and humiliated and “do all sorts of unspeakable things to her helpless body”. I’m not very much into bondage, but this is just role-playing and all in fun, so I go along. Besides, she is paying good money for all of this, so who am I to refuse?

Usually, I play the role of a “prowler” who “ravishes her” or her “Master” and she is my “submissive”. That’s the role I was to play this time we got together. I had already told her how I wanted her when I arrived. She was to be kneeling in her living room, with her hands behind her back and a blindfold over her eyes. I left it up to her what to wear with the only requirement that she be “easily accessible”.

Gloria doesn’t like to leave her door unlocked, so just before I came over she told me where she hid her spare key. I opened the front door to her house and stepped inside her well-light entry. I removed my jacket and shoes and then walked further into the house and into the living room where Gloria was waiting. I stood in the doorway and silently observed her for a couple of moments.

She was kneeling there just as I had instructed, a blindfold keeping her from seeing me and with me still in my socks, my footsteps hadn’t given me away either. She had no idea I was there. The only thing she wore was her collar and an under the bust corset, leaving her large delightful tits and her pussy and ass all uncovered and waiting for my use. I had bought her the collar after we’d had a couple of dates and she told me that I was the only man she saw. She had pretty much told me in so many words that she was exclusive to me, even though she knew I wasn’t and couldn’t be to her. So I bought her the collar for us to use whenever I came to visit with her and she loved the gift.

Without word or sound, I walked up behind her and reached down to cradle her face in my hands. “Oh!” she gasped as my unexpected touch startled her at first, but then the realization of who I was sank in and she relaxed into my hands.

“Hello, my slut. Have you missed me?” I asked her in a low growl.

“Oh yes, Master, more than you know. I am so glad you could come to visit me,” she said softly, but I could sense the lust in her voice right away.

“Well, I am here now. Have you been a good girl for me?” I asked.

“Yes, Master, I’ve been very good. I have gotten all my work done before you came here so I could spend all my time with you,” she said proudly of her achievements.

“That IS a good girl. I may just have to reward such thoughtfulness. Would you like that, my little slut?” I asked her. As I spoke, my hands moved slowly down her neck to her shoulders and then down her chest to just above her soft creamy tits.

“Please, Master...” she mewled as she felt my hands on her chest moving towards her amazing tits. I knew what these creamy globes could do to and for her and planned on taking full advantage of that control momentarily.

Gloria likes it when I put a little of the harder stuff in with our sex and she doesn’t mind my pulling her hair, slapping her tits, or spanking her ass good and proper. In fact, for her, it’s a turn on when I’m not so gentle and gentlemanly. To each their own, I suppose – I can play it rough or romantic with equal ease.

So as she knelt there blindfolded, hands obediently behind her back, waiting for what she had no idea, I reached down and grabbed a big handful of her long platinum blonde hair. “On your feet then, slut!” I said hauling her to her feet by her hair. She moved her hands instinctively up to grab my hands, but thought better of the impulse and just got to her feet quickly to relieve the tension on her hair. Still holding tightly to her hair, I marched the blindfolded woman to a nearby wall and pushed her up against it.

Holding her by the throat now I warned her, “You’d better keep those hands behind your back or you will wind up over my knee, you understand me whore?” I growled as menacingly as I could.

“Y-yes, Master,” she said.

“Good, now spread those whore legs – you know how to do that I’m sure!” I said. She stepped out so her feet were about shoulder length apart.

“Wider whore! I know you can do better than that – how in the hell is a man supposed to properly fuck you in a space that small? Now open those legs!” I snapped. To emphasize my words I slapped the inside of her thighs rapidly until she did as I said.

“Yes, Master! Yes, Master! I’m sorry! I’m sorry, Master!” she said, quickly as she spread her legs out wider. Now that her legs were open I knelt down to examine her. I reached up and slowly traced my finger up and down her slit, and pulled her pussy lips apart to peek at her pink interior.

“What the hell is this, slut? You aren’t even wet! Don’t you want me to fuck you tonight? Or are you intentionally trying to piss me off?” I bellowed, acting angry at her.

“Master, please! I-I tried being wet for you, I really did. But I know how you feel about me playing with myself before you visit and I didn’t want to disobey you! Please, I’m sorry, Master!” she said, shaking now. I wasn’t sure how much of her trembling was due to the excitement of the game or fear about how I was going about it. So I decided to show her which one it should be.

“I suppose I am going to have to do it myself, then!” I said, in mock irritation. “Open your filthy mouth, slut!” I squeezed her cheeks and she opened her mouth obediently.

I shoved two fingers into her mouth as far as I dared, making her gag a bit, but not enough to endanger her. “Get these fingers wet before I shove them up that dried up cunt!” I barked. I pushed them down her throat a couple more times, making her gag and retch a little. I knew that this was just the kind of treatment she loved – the humiliation and debasing really turned her on.

When she had gotten my fingers wet (and I saw her pussy getting that way too!), it was time to make her even wetter. With one hand I held the lips of her pussy open and I unceremoniously shoved the two wetted fingers deep into her pink hole.

“Oh fuck, Master! Oh, God, yes! Fuck me with your fingers, Master! Oh please, that feels so good!” she cried out half in surprise and shock, and half in the pure pleasure of being filled up again.

“You like this do you, whore? You like my fingers up your dirty, dried up, whore cunt? You like when strange men fingerfuck you? What a fucking tramp you are ... a fucking gutter tramp!” I sneered.

“Yes! Oh God yes, Master! I am just a filthy fucking gutter tramp! Oh, fuck me, Master! Please! Fuck your dirty whore, I beg you!” she cried. Gloria must have been really horny that day because it seemed like no time before she was putty in my hands. Normally our game goes on longer and I have to play the role a bit more!

“And if I do fuck you what do I get out of it? I know you are going to want me to make you cum – you are always a greedy little fuck about that. So when I do make you cum, what are you going to do for me?” I asked.

“Anything, Master! I’ll do anything you want! I swear! Please please fuck me! Please make me cum! Make your dirty gutter whore cum!” she said, nearly sobbing now.

I took her blindfold off and grabbed her by the collar, pulling her face very close to my own. “You may come to regret making such a bold and open-ended promise, whore. You don’t know what it may entail!” I said.

Then I pushed her down onto all fours. “Give me your hair,” I said. She knew what I had in mind. She gathered her hair up like a ponytail, twirling it a few times to make a “rope” out of it and handed it to me. “Now crawl to the bedroom so we can get on with this,” I said, and I took off walking at a brisk enough pace, that I half dragged the girl down the hallway to her bedroom.

Once in the bedroom, I placed her on the floor on her knees again so she could watch me undress. She had seen me plenty of times both dressed and undressed, but it always got her going when she watched me undress ... the anticipation and excitement for what she knew was coming afterward made her juices flow every time. I removed my shirt, pants, and socks, leaving me in only my boxers. I stepped closer and brought her face up within a couple of inches of the huge bulge that had grown in my shorts.

“Take a deep breath, slut,” I commanded. She inhaled deeply and moaned aloud. “Yes, that’s the scent you have been waiting for. The smell that makes your pussy drool and your mouth water. The smell of a man’s cock. You love that smell don’t you whore?” I asked.

“Oh yesss...” she mewled.

I pushed her face into my crotch and rubbed my boxer-clad cock across her face, letting her feel the hardness and size of the object she so wanted. “You want this cock, don’t you, whore. You want to taste it, and you want to feel it bury itself deep in that slobbering fuckhole you call a cunt. Don’t you? Tell me how much you want this cock in your holes, slut!” I commanded.

“Please Master! Please fuck me! Fuck me with your fat, hard cock, please! I need it so bad! I need to cum so bad! Please let me cum for you Master!” she cried.

“Give me your hands, I commanded and instantly she held her hands up for me. I placed them in front of each hip so she could grab my boxers. Her hands were away from my cock and I didn’t let her touch it yet. I ever so slowly moved her hands down and revealed what was under my boxers a fraction of an inch at a time. When my cockhead finally appeared, Gloria whimpered. Then it slowly came out from under the fabric it had been imprisoned in. She saw inch by inch appear, as my cock got longer and more exposed, her whimpers got louder and more urgent.

Finally, my cock was completely uncovered and she saw it in all its eight and a half inch glory. “Oh, Master!” she groaned. I took her by the hair and held her head still as I rubbed my cock over her lips, not letting her lick it, but just feel it on her soft full lips. I smacked her cheek with it a couple of times.

 
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