The Gigolo Chronicles 7 - Deborah
Copyright© 2022 by Master Jonathan
Chapter 2
Erotica Sex Story: Chapter 2 - 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 smiled inwardly as my suspicions of this woman’s dire needs were confirmed. She was everything I had expected her to be – the quintessential attention-craving, neglected woman in need of someone to show her love and worth.
I pulled down her panties slowly, teasing her just a bit more. I uncovered what has to be one of the prettiest, most delicious-looking pussies I have ever come across – and I have seen a lot of them!
Deborah’s pussy was tight and tucked in ... only her clit poked the very tip out to see what was going on. Her bush was immaculately trimmed, short and full, and carved into an upside-down triangle starting just above her clit and small enough not to be seen under her panties or a bikini bottom. There was the telltale dampness to it letting me know that she not only wanted to be eaten – she needed to be eaten. And I’m not one to let good peaches go to waste!
“Mmm, I do love a ripe juicy peach!” I said as I spread her long legs wide apart to get a better view. Putting my face closer, I inhaled the sweet perfume deeply.
“Please, Tony please don’t tease me. I need you now!”
I used my thumbs to pull apart the lips of her sweet honey hole and peeked inside. Her pink walls were dripping her juices and I could see the glint of her ambrosia in every crease and fold. I fastened my mouth securely to her pussy and my tongue started snaking its way into her molten core.
“OH, MY GAAWWDD!” Her response was immediate and dramatic. Without my prompting her, she lifted her legs, grabbing her ankles and holding her legs straight and wide apart. This gave me optimum access to her especially since her ass was on the very edge of her mattress so I could even get to her small puckered asshole.
Tasting her for the first time put me in high gear as well and I devoured her pussy like it the first meal I’d had in months. I licked and lapped, sucked and nibbled on her ferociously and she writhed and squirmed, moaning and squealing in answer to my feasting.
“Yes! Oh my God, right there! Right there! Oh, fuck, Tony! Lick me! Lick my pussy ... yes, just like that! Oh God, baby, you do that soo good!”
The sensations I was reacquainting my new girl with were so powerful that she soon lost her concentration on holding her ankles. Her legs began to droop, so I lay them wide apart and used my elbows spread out to hold them in place. With her hands-free now, she reached up and began clawing and tearing at her tits, hoping to distract her shattering mind from what I was doing to her. She was in such a frenzied, lust-addled state that it was the only thing she could think of to do. But it did little good.
I knew what Deborah needed ... what she hadn’t gotten for a very long time, obviously. The woman needed a good orgasm. “Le Petit Mort.” She needed an earth-shattering, mind-rending, so-good-I-can’t-even-breathe orgasm. And I was just the man that could give it to her!
Two things I considered right off. First, Deborah had been “referred” to me by a very special client and friend. Referrals carry a lot of weight in my line of work and especially when they come from dear friends like Heidi. The second thing was that this woman was in desperate need.
Now I’m not the type of guy that women call when their love life is chock full and going swimmingly. I understand and accept the fact I am an “emergency fuck”. I am not looking to become someone’s one and only. I tried that once and it was a disaster.
But Deborah was in exceptional need, and as this was our first time together, I wanted to make sure she put my number on her speed dial for the next time she needed a little “reassurance”.
I had one particular trick I used when I wanted to get a woman off. A trick that has yet to fail me. I moved my mouth up a bit and sucked hard on her clit, pulling the nub into my mouth where my teeth gently trapped and held it while my tongue rolled over it and caressed it.
At the same time, I shoved two fingers of one hand palm side up into her drooling pussy, curling the fingers around her pubic bone and massaging that elusive place on a woman known as her g-spot.
Finally, and I don’t do this to all my girls because I know some do not like anything anal, I rubbed the thumb of my other hand over her puckered little anus. She responded as if anal sex was fine with her, so just as she crested, I shoved an index finger into that tight hole up to the second knuckle.
I may as well have stuck a cattle prod up her poop chute! She practically levitated off the bed as she screamed long and loud to the ceiling.
“OHHH, FUUUCCCKKKMMEEE! I’M CUUUMMMINNGG! OHHH FUUUCCCKKK!”
Deborah’s juices flooded her pussy and poured into my mouth as well. I drank her in as fast as I could, but she had been denied for too long and she was making up for it now. I had no chance of keeping up with her and her juices poured out of the edges of my mouth, running down my chin and smearing all over her legs finally soaking the sheet below us.
Deborah meantime was bucking and pitching like a rodeo bronc doing her level best to toss me off her. You see when she began to cum, I didn’t just pull back and watch the show. No, I stayed right in there licking and sucking and fingerfucking her even while she was cumming. So she was trying to rid herself of my vexing persecution. But I was securely in place and wasn’t going to be easily moved.
After what seemed like several minutes, her energy had been completely depleted and she collapsed, sweat-covered and panting from sheer exhaustion, onto the bed once more, moaning as I pulled away from her.
I stood up and watched her as I undressed. I took my time, giving her a chance to at least catch her breath a bit. I didn’t want to let her get too cooled down – we had only begun this little party and there was still all that fucking to do. But I knew she wasn’t “in shape” for a marathon fuck just yet!
When I was down to my boxers only, I came up to Deborah who by then was coming back to me. She sat up and I came up to stand between her widespread and still pussy dampened thighs. She looked up at me questioningly.
“Go ahead, Deborah.”
She smiled and took my boxers down slowly. As my cockhead peeked out over the top of the waistband she saw me for the first time. She pulled my boxers down a little further and my entire cockhead came into view and she could see how big around I was. She gasped a bit at my size (I’m not a small man, but I’m not really porn star material either).
She continued to pull my boxers down and the lower they went the more of me she saw and the wider her eyes got. Finally, she had revealed all there was to see and she dropped my boxers to my ankles.
“Oh my God Tony! You’re a lot bigger than my husband – not that I’ve seen him much lately!”
My cock is about eight and a half inches long base to tip and about three inches around the shaft. I am more than enough to fill most any woman, and I can proudly, and truthfully, say that in my professional career I have not left one woman disappointed or unhappy with my performance.
“Now I know why Heidi speaks so highly of you! She said that you make her feel things no one else ever had ... I can see why!”
“Well you are about to feel those same things ... are you ready?”
“Ready? I’ve been looking forward to this since I first called you!” She lay back on the bed like before, her legs wide and grabbing her ankles in preparation for me. I took a couple of condoms from my pants pocket.
“Tell me, Deborah, are you allergic to latex? I have to ask to see which of these to use.”
“No, I’m not allergic to latex but you are so sweet to ask. Thank you, Tony.”
“Hey, I take care of my girls ... and prospective girls!” I gave her a wink that made her giggle.
As my cock was already hard and ready to play I opened the packet and started rolling the rubber down over it, sheathing my weapon in protective latex. I moved between her legs and just as I was about to start she stopped me.
“Wait, Tony, can I ask you for a favor?”
“Sure, what is it?”
“I know you are wearing that rubber to protect from STD’s and I appreciate the precaution. But when you are finished and about ready to ... um ... cum, would you, I mean could take it off and cum in my mouth?
“Are you sure Deborah? I mean there are risks...”
“Tony, you use a condom with every girl you’re with right? And I’m sure a careful guy like you gets tested regularly. So I don’t worry about catching anything from you. And since you will be jacking off into my mouth, you won’t catch anything from me. Please, Tony, I love it when a guy cums in my mouth. And I really love the taste! Please?”
How could I argue with that? She had covered the bases - it would be safe for us both. She was right, I am very careful about STD’s. And this was something she really wanted. I couldn’t say no.
“Sure honey. When I am getting close, I will pull out and while you get on your knees, I will take this off and shoot into your mouth if you want. But before I do that, I’m going to make sure you have already gotten yours! Ladies first, you know!”
“Always the gentleman, Tony!” she smiled.
“Yes. Always.”
With my cock properly sheathed, I stepped closer and grabbed the base with one hand. With my thumb and index finger of the other hand, I spread her pussy lips a bit then ran the tip of my cock up and down her slippery slit, coating the condom in her natural lubrication. This also served to tease her a bit, getting her more and more anxious to really feel me. I slid the length of my cock up and down her slit, getting as much lubrication as I could on the rubber.
I never use those pre-lubed rubbers for one because they taste terrible (or so I’m told) and some of my girls enjoy sucking me while they “dress” me for sex. Secondly, and important for first timers, I don’t want any adverse reactions to the lubrication. Using her natural lubrication is more than adequate and by the time I’ve gotten to the fucking stage, my girls are always plenty wet, I see to that!
I pushed into her slightly, just enough to place my cockhead at the entrance to her tunnel. I looked at her focusing on her pretty face. I always love the expression I get from that first entry. Deborah was no different. As I slowly began pushing deeper into her, I watched her eyes get wide and her mouth drop open in slow-motion surprise. It’s one thing to see how big I am, but it seems a whole other matter to feel it! Whatever the cause, this first shocked and amazed reaction is priceless! Fortunately for me, I don’t see any of my girls often enough for them to get used to it so every time I meet with them it’s like the first time!
I sank my hard thick cock deeper into Deborah’s tight wet hole, stretching her wider and wider.
“Oh, Toneee...”
I smiled at the woman’s lovely face, a mixture of surprise and pure happiness. I continued going slow and deliberately because this was our first time and I didn’t know her pussy or how far in I could go. Plus I wanted her to enjoy every moment of this first entry, to savor every inch of my cock and how I was opening her neglected womb. She was tight as I expected her to be. Not having any kids and not having sex for a long time had made her nearly virgin tight – a very nice surprise for me!
Finally, I reached the bottom of her well and bumped against her cervix. As I still had a little ways to go before I was fully in her, I marked the depth mentally so I wouldn’t thrust too far in and hurt her.