“Elizabeth, my dear, of all the pleasurable things there are in the world to do, the only thing I prefer to eating your wonderful pussy is fucking your wonderful pussy. Let me know when you are rested and ready.”
Her smile grew broader. “You are such a flatterer. Just let me rest for a minute and then we’ll see if your cock is as good as your tongue,” she said. Elizabeth knew full well that my cock was every bit as good as my tongue–I never let my lady friends down and she was one of my favorites.
She knew I would make damn sure she got every bit of value from the experience, and that if she could get up and walk to get her purse to pay me, I wasn’t done fucking yet! A lot of people in this profession–men or women–charge by the hour.
Not me. I charge by the experience. Which means I will stay there and continue fucking until my client gets the full enjoyment from it. Which is why I get paid so well and still have a large clientele… my lady friends know when they call Tony, he delivers!
Elizabeth rolled up against me and we hugged with the entire lengths of our bodies, wrapping our arms and legs around the others and getting as close as two people can get, both of us enjoying the contact.
Elizabeth had called me a flatterer, but my words weren’t meant to flatter her or bolster her ego. She had been a top model and now had a very successful line of fashion and makeup. She didn’t need an ego boost.
No, I had told her the truth… at that time and place, eating her pussy and fucking her pussy were the two most pleasurable things in the world. I would say, with complete truth, the same thing about any of my lady friends when I am with them. Elizabeth was probably aware of this, but she didn’t pursue the subject because she knows that I never talk about my other lady friends.
When she was rested and ready to continue, Elizabeth rolled over and got up on to her hands and knees. She knew from our many times together, that I was aware that she likes to start out doggy style and switch to finish in the missionary position. She likes to be “taken” in the doggy position because she likes it when I am dominant and a bit more aggressive with her at first.
I enjoy making love with Elizabeth any way she wants, but my favorite is the full body contact of the missionary position and I especially like to enjoy a mutual orgasm while there. However, my job was to please her however she likes it and I had been with Elizabeth enough times to know what she liked and how best to give it to her.
With Elizabeth on her knees, I rolled on my condom, knelt behind her, and spread her freckled ass cheeks. Her pretty pink rosebud winked at me and I leaned forward to give it a little lick, causing her to moan as she felt my tongue back there.
Elizabeth had yet to let me fuck her sweet tight ass, although I had asked her if she wanted me to a few times over the years. I was hoping that maybe this trip she would relax her views about anal sex and let me pop her anal cherry. I knew Elizabeth pretty well and I had a sneaking suspicion that she would enjoy it if she would just let herself.
She did like it when I rimmed like I was doing now and she had even let me rub my finger across it when I fucked her doggy-style a couple of times. So I knew the sensation of being back there was pleasurable for her.
As I licked her crinkled asshole and rubbed my finger over it lightly, she wriggled her ass back at me and moaned loudly, telling me how wonderful it felt. Juices were running from Elizabeth’s pussy down both her legs and onto the bed, and she reached underneath herself and spread her pussy lips.
“Fuck me now, Tony! I need you inside me, baby! I need you to fill me up with that beautiful, thick cock!” she moaned. Oh well, so much for talking her into anal! With one hand I steadied myself, and with the other, I guided my cock to the entrance to her love hole. With one slow, gentle shove, the tip entered Elizabeth’s pussy.
After the initial penetration, she let go of her pussy lips and leaned forward so her weight was on her knees and elbows, with her face pressed into her pillow. Her ass and pussy were high in the air for my pleasure, and for me to pleasure her. Two more gentle strokes and my cock was buried in Elizabeth’s lovely pussy.
“Mmm,” she murmured. “I really love that. Fuck me slow and deep.”
Slow and deep it was. One hand was on either of her thighs and I moved my hips back and forth, stroking my cock slowly into Elizabeth’s pussy, as deep as I could.
After two strokes, she started pushing back to meet me, and my cock going in and out of her sopping wet pussy made a pleasant, squishing noise. Neither of us would cum for quite a while, especially with the slow strokes we were using. but Elizabeth prefers to start in this position and I have no objection.
She murmured again, “Oooh, that feels really good. Take it easy, we’ve got all day. Let’s just fuck.” Since that sounded like a wonderful idea, I heartily agreed.
After the first few strokes, she began fucking back to meet my thrusts in the same rhythm I had started, but she soon wanted to use the circular motion she favors. My strokes didn’t change much, but I timed them so my cock plunged into her pussy in time with my hand which was now wrapped around her waist and fingering her hard throbbing clit. Her moans of pleasure mixed with my own to form an erotic duet.
After about ten minutes of slow strokes in the doggy position, Elizabeth, in between her sighs and moans of pleasure, let me know she wanted to change position. I backed slowly out and waited for her to turn around and lay on her back, her legs spread out on either side of me and her face shone with lust and sheer ecstatic happiness.
The combination of the pillow and her own ass put Elizabeth’s pussy at a good position, and I turned toward her and started plunging my cock in and out of her as soon as the shift was completed. One of the many beautiful features of Elizabeth is her large, freckly breasts with their pink nipples.
Earlier, I had enjoyed the taste and the feel of them on my tongue and now I was enjoying the sight of them, swaying to her motions. I reached out and caressed her there, feeling the erect nipple against my fingers.
I aimed my cock at her drooling pink hole for the first stroke in this new position, and I could see Elizabeth smiling at me and then she puckered up her lips and reached her arms to me. As I stroked my cock forward into her, I kissed her gently, and she hugged me around my neck, so our faces would stay close together.
This intimacy is what I most like about this position. My lips remained pressed against hers as I drew back for the second thrust, and this time, when I moved forward, Elizabeth pushed her pussy up to meet me. All my weight was on my knees and elbows so she had full freedom to move under me, and Elizabeth was glad to use that freedom.
At first, she just thrust her hips up to meet me when I plunged my cock into her but after a few strokes, she started swivelling her hips so that my cock massaged all the interior of her love hole. The sensation was wonderful to me and to her too. “Oh, Tony, I love your cock in my pussy. Keep fucking me. Let’s fuck all day.”
Fucking all day sounded great to me too. “Elizabeth, your pussy is one of the great wonders of the modern world. Fucking with you is about the best way I can think of to spend the day.” There was some flattery there, and even Elizabeth recognized that, but she smiled, enjoying what I said and what my cock and her pussy were doing for each other.
Both of us knew that we wouldn’t be fucking all day, but we wanted it to last as long as possible, giving us the most fun. A good way to make it last is for me to drive my cock slowly into Elizabeth, and for her to thrust her hips upward to meet me at the same speed.
The slow strokes would give her a chance to move her pussy around so my cock would caress the entire interior, and be caressed by her entire pussy. We were moaning in unison because what we were doing was so intensely pleasurable to both of us.
Elizabeth stopped swivelling her hips and, instead, wrapped her legs around mine and started a circular motion. Timing her movements, I drove my cock into her pussy when I could be sure of the best contact with her clit.
“Oooh,” she moaned on the first stroke. “That’s goood. I love your cock on my clit.” Again and again, my cock surged into Elizabeth’s pussy, and she moaned her pleasure at every stroke.
Even though we were fucking slowly to make it last, I could feel my Elizabeth getting close to her climax. “Okay, Tony. I’m close to cumming, baby.” I moved forward on top of Elizabeth so my cock had a stronger contact with her clit and I increased the speed of my strokes. She resumed fucking straight back to meet me and matched my speed. We continued with stronger contact and increased speed for several minutes.
“Oh! Oh! That’s it, Tony. I’m almost cumming. Give it to me! Yes! Yes! Fuck me good. Oh, God, I’m cumming! Fuck me! Fuck me!” and when she said that, Elizabeth held me tighter around my neck and hips and rammed her pussy against me even faster.
I matched her speed, driving my cock into her while I could feel my balls bumping against her ass. “Fuck me! Fuck me!” she cried, and I did as she demanded, plowing my cock into her pussy as fast as I could, feeling my cock scraping against her clit.
When Elizabeth had cum the first time, from my eating her pussy, she had taken a long time before climaxing and she took even longer this time. I am not complaining because I enjoyed it almost as much as she did, feeling her pussy against me, and her arms and legs around me.
Ecstasy can’t last forever, though, and finally, she climaxed, giving my legs and neck an extra squeeze and ramming her pussy against me one last time, before collapsing on the bed under me, tired and happy.
I rolled over to lay next to Elizabeth and kissed her as she smiled up at me. We lay there for several minutes until her breathing returned to normal and she could talk.
“Oh, Tony, you always make me feel so wonderful! I love getting together with you baby!” she whispered to me.
“And I love getting together with you too, beautiful. You are my favorite fucktoy!” I said. Elizabeth giggled at the name but then she noticed that I still hadn’t cum and was still rock hard.
“Oh poor baby–you haven’t had yours yet!” she said.
“That’s okay so long as you are happy that’s what I care about,” I said, being gallant.
“Tony, do you want to fuck my ass?” she asked. It was a very good thing I was already laying down or I would have dropped like a sack of potatoes at her suggestion!
“What? Elizabeth do you mean it?!?” I sat up looking at her, my eyes very wide. She grinned and nodded.
“Yes, Tony, I want you to fuck my ass. I know you have wanted to for a long time, and I do like when you lick and play back there. Just promise me you will take it slow… this is my first time,” she said softly.
“Of course Elizabeth,” I said, kissing her sweetly. “I would never want to hurt you.”
I always carry a little nylon zippered tool bag with a few things I might need when I go to meet a client. Nothing ruins a date like not having enough condoms or lube or something! I got up and grabbed a small bottle of lube from my bag and came back to the bed.
“Up on your knees, Elizabeth,” I said. She smiled and moved into the popular “face down – ass up” position; on her knees with her chest and face on the bed, her ass high in the air, and her legs spread. I squeezed a small glob onto my fingers and put it on her little rose, rubbing it around and spreading it where it needed to be.
I gently pushed a fingertip into her hole making sure I got her anal ring good and lubed as well. Another glob of the lube and I pressed it into her a little further, wanting to get her chute slickened up as well. Once I figured she was lubed good and proper I began introducing one then two fingers into her asshole, slowly opening her and stretching her in preparation for my cock.
“Oh, Tony…” Elizabeth moaned as she felt my fingers opening her ass. She tried to relax and accept what I was doing, and I felt her ass muscles loosen a bit.
“That’s it, Elizabeth, just relax and trust me, baby. I won’t hurt you, I promise,” I said.
After I had gotten her ass ready for me, it was time to lube up my cock. I put a good dollop of the lubricating jelly on my cock and worked it all around and the full length of my shaft especially over the head.
So after getting us both thoroughly lubed and her ass opened a bit, it was time to start. “Okay, Elizabeth, now I am going to take this nice and slow. If you want me to stop for any reason, just tell me and I will stop immediately. Now relax and let yourself go, all right? I will take care of you… I always do honey,” I said in a calm soothing voice.
“O-okay, Tony… I trust you, baby,” she said.
I moved up behind her until the tip of my cock was nestled in her ass crack. I pulled her cheeks apart exposing the target I intended to take and Elizabeth gasped a little. I gently bumped at her entrance just a bit so she would know I was there.
My cock was steel-hard from the lubrication action and the anticipation of exploring virgin territory. I watched as she gathered the corner of her pillow in her mouth and clutched at the sheets in preparation.
“Okay, here we go hon,” I said and I eased forward just a bit. I watched as her hole parted and the tip of my cock made entry. I pushed a bit more and slowly, very slowly, I slipped further inside.
“Ohhh…” she moaned as she felt her ass opening to me. I pushed a bit further and the rim, the widest part of my cock, was at her anal entrance. One more push and I felt myself slip inside with a little pop.
“OH!” Elizabeth gasped as she felt her ring shrink suddenly around my shaft.
“It’s okay Elizabeth, it’s just the head of my cock inside you,” I said calmly. I stayed just like that for a few moments, letting her get used to me inside her and talking calmly to her. My calm, relaxed voice and telling her just what was going on helped to ease her mind, and she felt a lot better about the idea.
“Okay sweetheart, I’m going to move in a little deeper now,” I said.
“Please be gentle Tony,” she said again.
“Of course I will beautiful,” I said. I pressed forward easing myself deeper into her. I sank another inch or so into her and stopped to let her rest.
“I’ll tell you what, Elizabeth. I’m going to stay still and let you move at your own pace. You just push back onto my cock as you feel you can, okay honey? That way you are in control and can adjust as you feel able to,” I said.
“Okay, maybe that would be better,” she said. She slowly pushed back on to me, and I watched as my cock slowly disappeared into the ass I had waited so long to enter. So gently, slowly, lovingly she pushed more of me into herself.
When she had me about halfway in her she stopped, to rest I guess, and get accustomed to my size. Then she pressed even farther back until I was all the way into the hilt, buried in her colon.
Have you ever felt a woman’s ass-cheeks pressed against your groin when you are as deep as you can get inside her ass? I was in heaven! Holy shit it was great! I can still feel her hips and everything pressed back to me.
I could even lightly feel my balls pressed against her pussy and her fingers manipulating away on her clit, I leaned forward and played with her wonderful full tits, Kissing her on the back of the neck and whispering soft endearing words in her ear.
“God you feel so fucking good, baby. Your ass is so tight and so warm! Do you like this? Do you like my hard cock buried deep in your tight little ass?” I asked, growling deeply.
“Oh yes! Yes, Tony! Oh, fuck my ass! Please fuck my ass now!” she whimpered. As I had always suspected, now that she had experienced it, she loved anal sex. I had created an anal slut!
Elizabeth put her head down and started moving her hips on my cock. I could feel the tightening and loosening as her sphincter worked to eject me from her tunnel, it wasn’t having any luck, but it felt so damn good. I could see her hands gripping and clawing at the sheets as she ground her ass into my hips, pushing back like she wanted even more of me in her.
Then she reached down to her pussy again and after tickling my balls she pressed two fingers inside herself and up against the back wall of her pussy. I could feel her fingers right against the bottom of my cock, but inside her pussy and through the walls of flesh, she was so amazing!
Elizabeth liked to make a little noise when we have sex, and I encourage her to “let her slut out” and talk dirty. I love it when a woman begs and pleads and tells me just what she wants me to do to her.
But now with me in her ass for the first time, playing with her tits with one hand and her pussy with the other, she made the most wonderful sounds. And they were loud sounds! Things like “Fuck my ass faster, harder, Oh God yes! Give me more! More! Yes, baby, right there, Yes YES!”
Suddenly I couldn’t take it anymore and grabbed her hips and pushed as hard as I could up her ass and she leaned back against me. We could both feel this molten blast coming out of my cock up into her rectum, I usually have a pretty good load but that one was out of this world. She came right at about the same time, God it was wonderful!
We both came together and afterwards, we collapsed with me on top of her, holding my upper body up off her with my elbows so she could catch her breath. She moaned as she felt my cock shrinking back down and finally plopping out with wet sound. I rolled off her and we lay in each other’s arms resting and kissing and cuddling.
The only problem with the whole experience was that her poor ass was sore for about five days or so after that! She stayed with me for a couple of days before heading back home to New Orleans and called me a day or two after she got back. I felt really bad, but she never was mad at me, she just said it was a heat of the moment thing.
Then she told me, “Actually even though it was a heat of the moment thing, I still think of how good it was every time I have to use the bathroom… and it turns me on all over again!” I was glad for that.
Anal sex was never the main ingredient in our lovemaking, but we did use it when we wanted to spice things up a little and it sure worked great for that. And it still gives us some of the best orgasms we can have. I can’t wait to see her again!
Copyright © © Copyright 2013-2018 by Master_Jonathan
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All names, characters, businesses, places, events, and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters portrayed in this story are over sixteen (16) years of age.
<a href=”https://www.lushstories.com/stories/taboo/-the-gigolo-chronicles-ii-elizabeth-1.aspx”> The Gigolo Chronicles II – Elizabeth, Part 2 </a>