A Different Kind of Open Marriage Ch. 03

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A regular client pays Tracy to take his son's virginity.
3.5k words
4.27
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12

Part 3 of the 3 part series

Updated 11/19/2023
Created 10/28/2023
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Hello, I'm Tracy and this is the continuation of my story as a married woman who escorts. If you haven't read the first part -- 'A Different Kind of Open Marriage' -- then I urge you to do so, as well Part II -- in order to understand how my husband and I got into this situation, and my background.

We have two kids, live in a nice house way out in the country. My husband Jim enjoys sports and is in good shape, and our sex life is good -- its gotten better, in fact, since I began my 'extracurricular activities. Myself, I'm 108 pounds, 35C-22-35, about 5'6" tall in high heels. My hair is long, silky straight, dark brown, cut off my shoulders, with bangs -- the 'Bettie Page' look. My eyes are blue, I exercise and work hard to stay in shape and keep trim, the results are a tight ass and shapely legs. My breasts are full and firm -- one of my best assets - with just a hint of sag that comes breastfeeding; just enough to show they're real. Men and women both tell me I'm beautiful.

Earlier, I discussed how I have always been a sexual person, have been sexually active since high school -- although I was never the town slut or anything like that -- and of course I discussed many aspects of my youth and my initial sexual awakening, which took place with my best friend Cathy. I didn't know it at the time -- I thought we were just 'experimenting' - but over time I came to realize that I am actually bisexual. I am sexually attracted to women as well as men, and although I prefer sex with men, I find women beautiful and I do enjoy an occasional sapphic dalliance.

We'll pick up the story at one of my more unusual 'dates'. One of my regulars, a middle-aged gentleman, had a request -- would I be willing to take his son's virginity?

"Bring me the boy," I said to him, "I'll give you the man."

I told John (not his name, obviously) the room number at the hotel I usually worked out of. I have a deal with one of the managers -- he makes a room available for me and I give him the occasional blowjob. For tonight he'd set me up a suite with a separate bedroom, very swank, and I was waiting when John brought his son up to meet me. I chose some tasteful lingerie -- thigh-hi's and heels, G-string panty, no bra, and a sheer robe that left nothing to the imagination -- everything in black, the whole femme fatale vamp look, suitable for my persona as Sophie, the high-class whore.

I put a porno on the flatscreen, with the sound down low, as a mood setter, and poured myself a glass of wine. There was a knock at the door. I was surprised to see both of them there, but didn't say a thing, just an almost imperceptibly raised eyebrow.

"Hello, John," I said, offering a cheek for his light kiss. "So nice to see you. And this must be George -- I'm Sophie and I've heard so much about you!" George couldn't rip his eyes off my chest, which was fine, that's why I had the goods on display -- I could tell that the young man's head was spinning.

"Please come in, sit down," I said. Indicating the sofa, I asked, "Would you like a drink?" I had a bottle of Scotch on the sideboard -- I get paid well to entertain gentlemen, and so I like to do it properly. John smiled as I handed him his Scotch, and as his eyes traveled down to openly gaze where my nipples were poking through the see-thru material, he smiled even wider.

I took George by the hand and told John, "I hope you're comfortable, John, while George and I get acquainted?" Then to George, "I'm sure we've got so much to say and do!" as I led him into the bedroom.

It was obviously necessary to start things off slow and easy with the young man, because he was as nervous as a cat in an alley full of bulldogs. We sat on the little loveseat sofa. George was a little tense, sitting very stiff with his hands in his lap. I put a hand on his and said, "So tell me a little about yourself, George. You're in high school?"

"Yes, ma'am."

"Please, call me Sophie," I laughed. I mean, I was sitting there in a see-thru robe and we both knew what was going to happen over the course of the next hour, and the young man was call me 'ma'am' like I'm a teacher or something. "So, you play sports?" I asked.

"Yes ma'am. I mean Sophie."

"There you go again," I said, placing a hand on his chest. "You mustn't be so formal, George. Think of me as an old family friend." This was true, in a way. Truer than he could have possibly imagined.

"Well, I like baseball," he said, "and I run track."

"Are you nervous?" I asked, tracing a finger across his lips -- what was needed was an icebreaker. I put my arms about George's neck and leaned forward. Our faces were very close, our lips almost touching.

"Er, um," was his response. His heart was beating so hard in his chest I could feel it, about a thousand miles an hour.

"Don't be," I said. "I'm going to take good care of you, and you're going to find this is the most natural thing in the world." I undid the sash on my robe, let it fall open a bit, all the way down to my panties. Then I closed my eyes and placed my lips on his.

The young man returned my kiss ever so gently, his lips just barely on mine. He was trying so hard to be well-mannered - because of the age thing between us, I suppose - and that seemed to tame the tiger in him for a moment. Then I felt his hardness poking through his jeans. I mean, it felt like he had a rod of steel down there!

I like sex with younger guys -- sometimes, the younger the better. Their cocks are SO hard, they fuck like jackhammers, and they're just so damn grateful! The only drawback is a young man tends to cum too soon, but I've learned to manage this.

As we kissed I pressed closer, parted my lips and our tongues met. His cock felt like he had a cucumber in his jeans, and I gave it a squeeze. We broke the kiss and I was like a kid at Christmas, undoing the front of his pants - I had to see what he had in there. When I pulled them open his boner sprang straight up. "Oh my, George," I gasped and my eyes went wide. "You have a REALLY... BIG... COCK..." We both looked at his huge erection poking straight up like it had a consciousness all its own - bold, impudent.

I got up, shrugged off the sheer robe and went to my knees before him. His cock was pointing straight at my face. I closed my eyes, pursed my lips and put a nice wet kiss on the very head of that big, beautiful cock. I felt his cock throb, leaned back, opened my eyes and saw a drop of shiny liquid glistening right at the very slitted tip of his cockhead. Without hesitation, my tongue darted out and I licked it up, and ran the tip of my tongue over my lips in a lustful manner.

Then I parted my lips and took his hard, hot cock deep into my wet mouth.

The young man inhaled deep as I sucked his tool. I closed my eyes and hummed a bit, my signature move. Then I looked up at him, looking directly in his eyes with my mouth full of his cock.

There's something about making eye contact when you're sucking a man's cock. It's an unspoken acknowledgement that makes an intimate act something totally wanton -- 'yes, I'm sucking your cock.' In this case, it was 'I'm old enough to be your mother, and your cock is in my mouth.'

Every young man loves having his cock sucked by an older woman.

I was on my knees before him, with his trousers down around his ankles and my lips and tongue running up and down his pole. George moaned and groaned. Then I wrapped my wet lips around his shaft once more and I felt his cock stiffen even more as my head went up and down. I let a lot of slobber drool all over his pole and, making a circle with my finger and thumb, I began stroking him into my mouth.

George placed his hands on the sides of my head, ran his fingers through my hair. His breath was becoming short. Like I said, a younger man cums too soon, and I could sense this young man's moment was soon. Releasing him from my mouth I stretched tongue all the way out and began jacking him off into my mouth.

"G-A-A-A-A-A-H-H-H..." was all he said as he unloaded his first shot of jizz across my outstretched tongue. With a mighty groan, "UHHHH!!!" George spurted white hot cum all over my lips and tongue. His second shot landed a dollop across my cheek. I engulfed his cock in my mouth and sucked as his cock pulsed, shooting the remainder of his load.

I moaned my appreciation, closed my lips around his pole. His cock pulsed in my mouth several more times as I continued stroking him off into my mouth. When he was finally done, I sat back on my heels, my mouth partly open so he could see his jizz dripping over my lower lip, dribbling down my chin and puddling up on my heaving breasts. It's all about the visuals with men, and I love being such a slut for my clients.

Then I went down again. I licked him clean, then I used the head of his cock like a spatula to wipe up the gobs of cum all over my face and deposit them into my mouth. "Wow, George," I said, between swallows, "That is a LOT of cum!"

But I did not stop - I continued to suck. It was my intention to suck him back to full hardness, not letting his erection subside. I sucked like a soul possessed, releasing him from my mouth only to work lips and tongue up and down the length of his pole -- pure cock worship.

"UNNNGGGHHH..." was all the young man could manage to say, sitting there with his head thrown back, trousers down around his ankles and his glistening wet cock pointing straight up at the ceiling.

I got up, offered him my hand. "Come with me, lover," I said. "Let's get you out of those clothes and into bed."

The thing is, a young man cums too soon, but a young man recovers quickly and his cock is just as hard. What I've found is that for round two, a young man will stay harder, longer, able to give a good pounding.

We lay together and gazed into each other's eyes -- we'd already shared so much that the age gap between us seemed to fade away. George was fondling my breasts, then moved his head down to kiss them, to nibble and suck on my nipples. That always feels great. Then George moved over me and I felt the head of that magnificent cock pressing on my wet pussylips. His being a virgin, I was willing to let him in bareback. I reached down to separate my labia and he pressed it in.

OH. MY. GOD.

George's cock felt FANTASTIC. My wet pussy clenched about his girth as the young man's thrusts went from slow to a medium rhythm to WARP SPEED. I wrapped my legs about his and hung on for dear life as George's rod plunged in and out like a piston.

One of the best parts about doing it with really young guys is the amazing fuck-faces they make while they're experiencing sex for the first time. I just love the way their faces go from intense to exhilaration to absolute rapture when they cum inside a woman for the first time in their life. As for me, I swear I was having one continual squirting wet orgasm the whole time with George -- he was that good!

I finally had to pound on his arm to let George know his weight on top of me was too much. "Let me up, lover," I panted, "Let me get on top for awhile." I wanted to ride his amazing pole. I straddled him, arching my back as he placed his hands on my breasts. Again, I was practically cumming the entire time I was on George's cock -- there really is nothing like having your wet pussy impaled on a young man's hard cock.

After a while we rotated again, this time I went to my hands and knees and George was giving it to me from behind -- doggy. This is the best way to get it in really deep, and George was gripping my hips as he pounded it in, balls to the walls. His hips slapped against my butt cheeks until I collapsed and now he was giving it to me in the prone. I was spread my legs wide beneath him as he went up and down on me. George roared as he climaxed, his face buried in the pillows next to mine. I was spent, yet still my pussy was still cumming around his plunging rod as George unloaded bucket loads of hot cum deep inside me.

We lay together in the afterglow, and the look on his face was one of pure happiness and bliss. Then I did my little run to the bathroom, came back and collapsed on the bed. Then George got up and went to the bathroom, and then he got dressed. He went to the door and when he opened it, John was there.

"Oh hi, Dad," George stuttered. I was still laid back on the bed, stark naked, of course. His Dad didn't say anything, just stepped past him, came up to the bed and started taking his clothes off. Like Father, like Son -- right? -- only this time, in reverse, I guess. George left the room.

John was already erect, full mast -- he'd been out there watching all that porn, after all, while his son and I were doing it on the other side of the door. This wasn't an expected part of the deal but I didn't say anything -- John had paid a lot for me to deflower his son, and he was always a good tipper. I simply swung around to sitting on the edge of the mattress, put my hands on his hips and my lips on the head of his cock. I swirled my tongue about his cockhead and all about the edge of his helmet. Then I formed my lips into an O, took his length deep into my warm, wet mouth and dutifully began sucking, like a good little whore.

I looked up, looked John in the eyes. John looked down at me and smiled, running his fingers through my hair and stroking my cheek as I slowly sucked his cock. Finally I pulled off, moved back and patted the mattress, indicating for him to join me.

We lay together, kissed some. John was usually a conversationalist but this time he did not speak -- I assumed the fact that I'd just fucked his son was a bit disquieting. To alleviate any awkwardness, I simply moved down and continued licking up and down his shaft, nibbling and licking his balls and slobbering a lot of slobber all over his tool as I moved back up again to stroke him into my mouth. I figured the longer I sucked his pole and stroked him off like this, the faster he'd be done and over with when we started fucking.

And fuck we did. John moved over me, looking me dead in the eye as he positioned the head of his cock on my wet pussylips. "Ooh yeah, give it to me, lover," I whispered. John gave it a push and it went right in -- I was already thoroughly wet of course, my pussy was full of cum - John's cock was saturated in his own son's jizz.

Making it with John was a little more methodical than the fucking I'd just received from his son. George had given it to me like he was running a four-minute mile -- with John it more a pleasant walk through the woods, and that was pleasant too. I'd already cum so many times from his son's hard pole I'd lost track, I couldn't cum from the older man's cock but ever the good courtesan I faked it, dutifully squirming beneath him and squealing "Oh give it to me, lover! Fuck me! Fuck me!" An older guy needs all the encouragement he can get. He was grunting and groaning, humping away on top of me and I was crying out "FUCKMEFUCKMEFUCKMEFUCKMEFUCKMEFUCKMEFUCKME!" clutching him and gasping as he unloaded his cum deep inside me.

I just lay there, spent, while John got up and went to the bathroom. Then I got up, pulled on my sheer robe to see John and his son to the door. It was kind of funny, because John kissed me on the lips -actually slipped me a bit of tongue - then his son George kissed me on the cheek like I was his mother or something. Meanwhile both of their combined fluids were leaking out of me and dripping down the insides of my thighs. Like I said, John tipped well -- he was not a cheap Charlie -- as he left he thanked me, kissed me again, and handed me several bills. I waited until he'd left to count them -- John had basically paid me twice.

That night was certainly one for the memory books. In more ways than one, actually, as I was about to find out.

After Jim brought me home from my 'date', as usual he drove Kaitlyn (the babysitter) home. Kaitlyn is a lovely girl -- long blonde curly hair that comes down almost to her cute little butt. Like I had been, Kaitlyn was a cheerleader in high school, she just graduated, in fact. Because I'm a total sexual degenerate, it occurred to me that young George could very well be one of her classmates. Possibly her Prom date, even.

I've often wondered if Kaitlyn and Jim engaged in the same kind of 'arrangement' I'd had with Mr. Norris, way back when I was babysitting. Not that it would have bothered me; I am not the jealous type, and what two people do alone in cars at night is between them -- I've certainly given my share of blowjobs in cars. I don't think it had happened yet, until that night when it took longer than usual for Jim to come home. When he finally got home, it was obvious that something had gone down. His disheveled look told me all I needed to know.

I didn't confront him about it -- I really am not the jealous type -- instead I waited until we were upstairs, in bed. I was spent and he knew that, and I was wearing my granny nightie -- which means no fucking -- and he understood that. I'm sure he was half hoping for a blowjob, which I often give him as thanks, after a 'date'. "Honey," I began, "Are you and Kaitlyn... you know...?"

"I, uh..." he stammered.

"It's okay if you are," I went on. "I don't mind. I really don't. I just want to know. 'Coz if you are, I don't want to think you're running around behind my back, trying to keep secrets from me. Especially that kind of secret."

"Well, uh, yeah," Jim said. I understood it was a difficult for him to talk about. He'd never shown an iota of jealousy, and I was completely sincere in what I was saying, but still...

"I just hope you're using some kind of protection," I said. "I like Kaitlyn, but I don't like her enough to become an aunt, or whatever it would be, if..."

It was my intent to say something about it with Kaitlyn, later. I wanted to let her know I'm open-minded and accepting, and I didn't want her to think she things were going to be weird when she was around me, avoiding eye contact of whatever.

Meanwhile it was time for sleep -- it'd been a long night -- and no blowjob for Hubby. I might not be the jealous type, I might be open minded and free thinking, but a woman has to have some sense of honor. I might be a whore, but I'm not that much of a whore.

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AnonymousAnonymousabout 2 months ago

I loved all three chapters! One correction though..... The proper analogy is "like a cat in a room full of rocking chairs"

MtRseMan99MtRseMan993 months ago

Thanks, really good series. Keep up the good work.

AnonymousAnonymous5 months ago

I’ve been told by friends that are single since the internet apps started with social media it took the street corner hooker with a pimp to women who needed money finding hook ups . It also can be dangerous but not as bad. We were in our early 20’s and guys were going to lunch for a hook up. Twice it wound up being someone they knew their kids well . Those two wound up fucking most of the areas classmates of her kids . Two guys had her at their dorm and dped her paying triple . She said seriously she’s not a slut and never been but they had fallen on a really bad financial situation and she’s embarrassed by what’s she’s doing. The friends roommate felt bad and set her up with athletes from the sports teams . She was earning really good supposed. Once the black athletes found out they were all over it . Loved they were fucking a guys mom that hangs with friends at the school parties.. all were shocked her family never found out. Probably because anyone paying to get laid didn’t want that to get out either . Lol

AnonymousAnonymous5 months ago

What a life! And she makes out lie a bandit and leaves two very satisfied customers. They should return soon.

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