The Gigolo Chronicles 7 - Deborah - Cover

The Gigolo Chronicles 7 - Deborah

Copyright© 2022 by Master Jonathan

Chapter 1

Erotica Sex Story: Chapter 1 - Deborah was referred to me by Heidi, another client of mine. I received her call at home and flew out to San Diego to meet with her. What I found was a woman in dire need of validation...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Cheating   Anal Sex   Oral Sex   Safe Sex   Squirting   Illustrated  

I was sitting in my living room having just got back from a business trip earlier that week and relaxing before fixing something for dinner when the phone rang. It was my answering service.

“Mr. Harris, you have a message from a Mrs. Deborah Covington. She would like you to return her call. Her number is (619) 844-2126,” the operator said.

“Thank you.” I hung up and looked at the clock. It was 4:30 in Dallas where I live which made it 3:30 in San Diego where the area code says this Deborah Covington called from. I dialed the number the service gave me and presently a woman’s voice answered.

“Hello?”

“Hello, Deborah Covington, please.”

“This is her. How can I help you?”

Mrs. Covington, my answering service told me you called and I am returning your call. My name is Tony. I believe our mutual friend Heidi has talked about me?”

“Tony ... OH, Tony! Oh, I’m sorry, I didn’t understand at first! Yes, she and I have talked and she told me that you might be able to help me with a problem I am having.”

“Well, I hope what she told you was good!” I said, jokingly.

“Oh, she said you were very good at what you do! She highly recommends you!”

“Awww, that’s nice. It’s always good to have a happy customer. Happy customers give good referrals, which leads to more clients. I will have to thank Heidi for her recommendation. Now, what is it I can do for you, Deborah?”

“Well, I was hoping that we could meet and discuss my particular needs in person. Do you think you could come out to San Diego? Heidi tells me you come out to California often as well as other places on business. I would really like to see if you could help me.”

“I think that could be arranged. I just got back from another trip, but my work often takes me from place to place. Heidi is a good client and a good friend – if she thinks I can help you and referred you, then yes, I can come out to San Diego. I usually plan on a couple of days for the initial consultation so I can get a good idea of your needs and how I can give you what you want. Does that sound okay with you?”

“That sounds wonderful! When do you think you could come to San Diego?”

The eagerness of her voice was now apparent, even long distance over the telephone. I knew this woman needed my services quite desperately.

“Whenever you want me to come out there. The rest of my month is pretty much open.” And it was. This month had started out like gangbusters and I had made more than enough to tide me over into the next month. But Deborah would add to the coffers quite nicely and I would have a new client on my books as well.

“That’s wonderful Tony. Would this coming Monday be enough time for you to get a ticket and make travel plans?”

Today was Tuesday and I have a terrific travel agent I always go to. She can get me on a flight with only a couple days notice. And I make sure she knows how much I appreciate her hard work too!

“Yeah, I think I can arrange for a flight out there next Monday.”

“That would be perfect. My husband will be away on a business trip himself so it will be perfect.”

“So there’s a Mr. Covington then?”

“Yes, of sorts. I mean we are married but only in name. We occupy the same house, but we don’t see much of each other. It’s more a marriage of convenience than anything. We were in love once ... a long time ago. Now neither of us wants to pull the plug on it for fear the other will win in the divorce.”

“I’m sorry to hear that. Unfortunately, yours is not an unfamiliar situation. A number of women seem to be in unhappy or unfulfilling marriages or relationships. But enough of this depressing talk. I will call my travel agent right away and have her book me a flight to San Diego for Monday with a return flight on Wednesday evening. That should give us enough time to discuss your needs and whatever we can do to correct the problem.”

“Oh thank you, Tony! I can hardly wait!” She hung up the phone and I could almost sense her relief. I immediately called my travel agent.

“Far Horizons Travel, this is Susan speaking.”

“Hi Susan, just the girl I was looking for. This is Tony Harris. I need a flight Monday morning for San Diego with a return on Wednesday evening sometime.”

“Hello, Tony! Let’s see. Yes, I have a few seats available. I have one that leaves at 6:55 am and gets to San Diego at 8:00 California time. It’s actually a three-hour flight, but it’s First Class.”

“That would be just fine. Go ahead and book me on that flight.”

A moment or two later Susan came back, “Okay Tony, you are all set. You’ll need to get to the airport a couple of hours before your flight but you know all about that stuff!”

“Thanks, honey and when I get back I will have to thank you properly for all your hard work in booking my travel needs!”

She giggled. “Ooh, I like the sound of that!” Then we hung up and I started fixing dinner. Susan remembered well the last time I “thanked” her for all she did for me, and she was eager for another thank you!

After that, the rest of the week went by pretty smoothly and easily – at least for me. I would hazard that time moved considerably slower for Deborah, however!

But the weekend did come, and I called Deborah back on Sunday just to make sure things were all set for my arrival in the morning. She asked me what flight I would be on and then told me she would meet my plane if I wanted her to.

“That’s okay hon ... I’ll take a cab to your place – you just make sure you are are ready for me when I get there!”

“Oh honey, I was ready for you the first time I called you!” She proceeded to give me her address so I could tell the cab where to go and then we hung up. I could tell by the excitement in her voice this was going to be a great trip! I knew that letting the anticipation and excitement build up in this obviously sexually neglected woman over the past week would insure a wild couple of night in the sack for us both.

The next day I made my flight easily and three hours later I was landing in San Diego. I had been to this airport a number of times so making my way through it was no problem at all. I hailed a cab and gave him the address and settled back for the short ride.

The cab pulled up to the front of a very nice two-story Colonial-style home in what looked like an upscale neighborhood. I took my bags out of the cab (I travel very light with just a couple small carry-on bags ... I don’t need to have my luggage going to someplace that I’m not!) and walked up the sidewalk, admiring the flowers lining each side until I got to her front door. A quick ring of her doorbell brought an almost instant response from the lady of the house.

“Hi Tony, come in please!” she said, with a blushing smile on her face. The woman that met me at the door was a very beautiful woman about thirty-five years old I estimated with straight dark brown hair to about the middle of her back, warm welcoming green eyes, and a very lovely smile. I was very pleasantly surprised.

“Wow, that was fast!” I commented as I stepped inside her home.

“Yeah ... I ... watched you pull up. I’ve been watching for you for about a half hour now. I’m really glad you came.” she said, looking down as if embarrassed at the reason I was there.

I crooked my finger and placed it under her chin, lifting her face to mine. “I’m glad I came too, Deborah.” I smiled and looked her directly in the eyes.

“Please come and sit down and make yourself comfortable. Would you like something to drink? A glass of wine perhaps? I have a nice Merlot...”

“A glass of wine would be perfect. And I love Merlot, it’s my favorite.”

She smiled “I’ll be right back then.” Personally, I think she was glad to have something to do and an excuse to slip away and catch her breath. She looked to me to be a little shaky and nervous and this gave her a chance to get herself together a bit.

When she came back in she seemed a bit more in control of herself and she handed me a glass and sat down on the sofa next to me, but at a respectable distance ... for now.

“I’m sorry Tony, but I’ve never done anything like this. What happens now?”

“Well normally on a first date, we talk for a bit and you tell me what you want from me and I tell you how I can help you. You have an advantage over some of my other girls in that you were referred to me and so you got an idea of what I can do. You have told me that you and your husband aren’t intimate anymore ... that you barely even speak to each other. So tell me, Deborah, what would you like me to do for you?”

“I ... um ... I mean ... oh this is so hard!” she said, looking down again and fidgeting with her hands.

Deborah was nervous, I get it. She wasn’t the first girl to be in that awkward, uncertain situation and she wouldn’t be the last either. I had walked all my clients through these first faltering steps. She needed someone to take her by the hand and help her as well.

I took her drink and set it on the table in front of us. Then I stood up, pulling her to her feet with me. I pulled her in close, wrapping one arm around her waist and lifted her face to mine with the other. “Heidi told you about me, but she didn’t tell me how beautiful you were. You look stunning Deborah, and I am so glad you called me.” Then I pulled her into a kiss ... that first kiss. She was hesitant at first as I expected, but as soon as she found out that the world didn’t end just because she kissed me, she warmed up and began returning my kiss.

I had Deborah pegged as a neglected woman in need of some sort of validation and looking for someone to tell her it was okay to feel again. But what I hadn’t counted on was the depth and scope of that need. After she got over the initial shock that she was kissing a man she’d just met only moments ago, her kiss turned into a desperate, hungry, devouring of my mouth. She kissed me like she was trying to suck the soul from me. Like she was drowning and I was her air line.

I felt her arms move up and wrap around my neck, holding me in the kiss and not wanting to let me go. No worries, I love kissing and wasn’t going anywhere. My hands moved slowly down her sides to her hips and then around to her ass cheeks. I squeezed her ass firmly enough to be felt, but not mauling her like some horny pervert. Apparently, I did it just right, because she moaned into my mouth when she felt my hands on her ass.

Taking that as a cue, I began to inch her dress upwards, gathering it at her hips as I revealed more and more of her long, lean legs. When I had raised the hem of her dress up above the tops of her stockings, she gasped a bit as the cool room air hit her naked flesh. I pulled her a little closer and continued. I reached the leg openings of her panties and then My hands went under her dress to caress her ass over her lacy black panties.

By now our kissing had become almost frantic – or rather hers was ... I was just trying to keep up!

Finally, she pushed me back a bit breaking our kiss so she could grab a breath of air. “Wait! Wait a minute, please ... it’s been a long time since I was kissed like that!” I smiled and held her to let her catch her breath.

“Tony, I want you ... more than you could ever know. And I hate to bring this up right now, but I need to know going in ... how much ... how much is this going to cost?”

Now I am not your garden variety skirt-chaser. I have skills I have perfected and use to make my lady friends feel special and very appreciative when I see them. This is also my living and I do very well at it. I have a very comfortable life and I get to fuck a number of beautiful (and well-to-do) women. I travel all over the country and I enjoy every minute of it. But I am not cheap. I cater to women who don’t mind paying a premium price for premium entertainment. And I make damn sure that they get their money’s worth! My livelihood depends on my ability to make a woman happy!

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