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How my wife became a high-priced escort

My wife, Jill, and I are in our mid-30s and have been together since we were 16. We were married immediately after college, and we’ve never been with anyone else. We are still wildly in love and very happy. We have two young girls who are the lights of our lives. For a while, we’ve been discussing exploring some fantasies, and last summer we took a big plunge.

Last summer, for our 15th wedding anniversary, we dropped the girls to stay with their grandparents, and we checked into a nice resort a few hours from our home, on the California coast. I changed in a business jacket and went to the bar to wait for Jill. Our hotel was a business and conference center, adjoining the resort. Our little fantasy was that she would dress up as if she’s a woman of the evening, and I would approach her in the bar. Pretty innocent, but it excited us.

After downing a couple of bourbons, I noticed out of the corner of my eye a flash of red enter the bar. I turned to see the most fantastically sexy woman I’d ever laid eyes on. Long reddish-blonde hair, blazing blue eyes behind dark eyeliner, big beaming smile with bright red lipstick. Below the neck, she wore a bright red slinky dress that hugged every curve, with a plunging neckline and a long slit up one leg. She was 5’7, hourglass figure, perfectly round ass and tight stomach clearly tone from working out, supporting the most magnificent 32DD rack. She wore a push-up bra with a peek-a-boo front so her nipples were prominent, unashamedly poking through the thin material. They were enormous, classic door knobs. She glided into the bar, her breasts swaying regally. I almost didn’t recognize my wife as every man in the room stopped breathing.

The bar was a dark, old-school cigar lounge with lots of leather upholstery and many old books on the shelves. It wasn’t very large, and there were only a handful of men, all dressed in business attire and seated in the corners. The bar had maybe 12 stools, all empty. As Jill slid into one, the bartender looked her up and down lustily and nodded, “What can I get you?” She ordered a Manhattan and sipped on it as the men in the corner keep ogling her and whispering and chuckling. They weren’t very subtle. I just watched in amusement.

As she was finishing her Manhattan, I was about to approach her, when Jill pulled a cigarette from her purse. I’d never seen her smoke before, so I was taken aback. She fumbled for a lighter, and suddenly a man swooped in to offer her a light. I hadn’t noticed him enter the bar, but he was a very tall, muscular-looking Black man in his 50s, with salt-and-pepper hair and a custom-tailored suit. He was very impressive-looking and had the air of a man of means. Jill was startled by his sudden appearance and looked him in the eye, momentarily stunned. She was impressed too. She held the cigarette to her lip as he lit if with his lighter. She smiled and thanked him. “May I join you,” he asked politely. Jill glanced at me, and I just sat back in my seat, so she gestured for him to take the stool next to her.

He ordered her another Manhattan and an expensive whiskey for himself. I couldn’t hear their conversation, but Jill clearly was entertained. Their body language suggested he was charming her. She giggled now and then and touched his arm, once even touching his thigh. She glanced at me once, and I just grinned. I was enjoying the sight. They finished that round and ordered another. Jill is pretty petite and can’t handle her liquor well, so I wondered how long this would go on. I decided to let it unfold however it did.

Near the end of the second round, the man leaned in and whispered something in Jill’s ear. She blushed and looked him dead in the eye, as if to ask if he were serious. He just nodded confidently and sipped on his whisky, never taking his eyes off hers. She looked at me, then excused herself to visit the power room. She walked out of the bar; I waited a few minutes, then followed. I found her outside the bathrooms in a panic. “He offered me $10,000 to take him back to my room. Let’s get out of here.”

I thought a minute and just calmly offered, “Not so fast. You clearly seem to enjoy his company, and we could use the money.” She scowled at me. “What are you saying? I should do it?” I nodded and smiled. You have said one of your fantasies is being with a stranger. Here’s your chance. She realized I was serious. “Really? You want this?” I nodded again. “I do. I’ll run upstairs and hide my things and get out of there. Give me ten minutes. Have fun!”

I bolted away as Jill just stared after me. I raced into our room and hid all signs of my having been there. Then I had a stroke of genius: I set up my laptop on the desk, in a dark corner of the room, and started up a video feed that I could watch from my phone. Then I propped a pillow in in front of the screen so that only the webcam was exposed. I left the room and went to the business center, which was empty, and I settled in to watch the show.

Within ten minutes, I could see the door open, and Jill and her suitor entered. She plopped her clutch purse on the bed and awkwardly sort of gestured around. “Well, um, here’s my room.” From my point of view, the man was silhouetted, an enormous shadow towering over her. Without saying a word, he put his big arm behind the small of her back and pulled her up, suspending her on the tips of her toes. He kissed her passionately, and I could see her body loosen up as she leaned into him. Even from behind, I could see that she was enjoying him. With his other hand, he slowly unzipped her dress and unbuttoned her bra. When he released her, her outfit just fell to the floor. My wife stood there in nothing but a thong and high-heeled shoes, gazing up at this hulking figure of a man.

“Undress me,” he commanded. She very tentatively began to take off his jacket, remove his tie, and unbutton his shirt. Once exposed, his torso seemed unreal: perfectly sculpted muscles and six-pack abs. How did a middle-aged man keep his body in that shape? He gestured toward his pants. Jill unbuckled his belt, unzipped his pants and pulled them to the floor. She removed them, along with his shoes and socks. Even in the dim light, gazing from the camera in the corner, I could see that under his loose black boxers was something monstrous, aching to get out. Jill just looked at it. He took her hand and placed it on his cock. I could hear her gasp. She slowly traced the outline, stroking it through the fabric as it responded to her touch. Even from across the room, I could see the head start to emerge from below the legs of his boxers. It was then I began to worry that this was a huge mistake.

“Take them off,” he ordered. Her little hands pulled at the waistband but struggled to get the shorts down over his growing member. Once she did, it leapt out at her, springing to attention. Jill literally jumped back with a start. “Oh my god,” she said under her breath. “I can’t… I can’t do this….” He removed his shorts and pushed her to her knees. She resisted but gave in. “Please don’t. Please don’t make me.” Hovering over her, he looked inhuman, a monster of a man looming over my mere mortal wife. He pulled on his cock a little bit, and I could see that it was the largest I’d ever seen. He placed his right hand under her chin and coaxed her mouth open while he put his left hand behind her head and brought her closer. He took the sizeable head of his penis and gently probed her lips. Jill placed her tiny hands on his thighs to brace herself. He pushed a little harder, with a few inches in her mouth now. “Mmmmmph.” He grabbed a fistful of her hair to get a better grip on her, squeezing her jaw a little harder, then in one sudden thrust he shoved his cock most of the way down her throat. From behind I could see her head dart back as she squeezed his thighs harder. She tried to pull away, but he began to fuck her throat mercilessly. “Ugggghhhhhphhh.” I could hear her sputter and spit as he violated her mouth.

This went on for several minutes, and occasionally he pulled out to let her catch her breath and spit but also to let her see how big his cock was now. When she coughed, he slapped her hard across the face. She stopped resisting, and by the third time he pulled out, she eagerly grabbed his manhood and gobbled it down again. She reached around and grabbed his ass to pull him in. She wanted all of it, and he obliged, fucking her face with abandon. I saw her exquisite ass cheeks clench as she took on this monster.

Finally, he was ready to take her. He grabbed her by the throat and lifted her to her feet, spinning her around and shoving her violently against the desk. She propped herself up on the tabletop, her amble breasts swaying beneath her. Her face was right up in the webcam, and I could see that her lipstick and mascara were smeared all over her face in streams of slobber and precum. She filled the screen, and in the dark I couldn’t see behind her, but her face made clear what was happening. She bit her lip and let out a long groan as he entered her. Then her eyes shot open in shock as his full length and girth filled her pussy. Her mouth dropped open as she stopped breathing, but after a few seconds she let out a long scream so loud I worried security would show up.

He fucked her like this for 20 minutes or more, the camera shaking as she struggled to keep her balance on the desk. Once I could see his big black hands appear over her tits as he squeezed her colossal nipples and waves of pleasure ran over her face. Jill seemed to be in heaven. “Please don’t stop. Don’t ever stop. I didn’t know it could be like this. My body belongs to you now. Fuck me forever! Pleeeeeassse.” She must have orgasmed half a dozen times, and I’d never seen her so beautiful before.

As this went on, I knew that I could never please my wife in the bedroom again. She had been awakened to desires and pleasures from which there was no turning back. I knew our love was true and safe, but I also knew I needed to let her explore such heights of passion, and I couldn’t give it to her. When he was done with her, the man threw her on the bed. He took out an envelope full of hundreds and rained it down on her. Then he quietly dressed and left. From the dim corner, behind a decorative pillow, I watched as my wife rubbed the cash all over her body, covered in sweat and cum.

That was a year ago. Since then, we’ve repeated this scene six times with other strangers in different hotels. Five months ago, we set up a website for Jill, and she sees clients a few times a week. I’ve become her assistant. Her reviews currently are the highest scores on TER, and we’ve begun a college fund for our kids. I’ve never seen her happier.