That Jana Caulfield was willing to cuckold me was something of a shock. She had always laughed at me for even thinking about doing anything like swinging, as she termed it. At first I wasn't sure if she was even taking me seriously. But, as it turned out she was indeed serious, and now I have this little predicament: she likes it and doesn't want to give up her more or less regular Saturday afternoon trysts! It was supposed to have been a one-time deal. But, now it has become the primary vehicle of my punishment.
Yes, yes, it was my idea originally, kind of a way to spice up our sex lives, as I saw it; probably not an original notion. The idea was that she'd pick up some stranger, let him bang her while I watched, and then we would have something to talk about for years to come. But, it didn't work out that way.
Now, I am made to watch, and the humiliation is often unbearable, yet I have no choice but to bear it. My wife, as it turns out has a cruel streak, and watching her and her lovers is but part of the picture.
Jana won't say, but I am sure she does it for the pleasure she gets out of it as much as a means of punishing me. Why don't I just scrambola? I love her, and, in point of fact, it is all my fault: talk about a catch-22. Every once in a while, I get the feeling that maybe she'll put an end to it all, but so far no such luck.
It's been almost a year now since the first time. And that first time was a doozy. Neither of us had ever done anything like it. We were nervous, and so was the pizza delivery guy that my wife finally did it with. I was there, oh boy was I ever there, but I was hiding in the closet.
We'd decided to go to a motel and order pizza. My wife would proposition the delivery guy, which we figured would be some young virile kid; and well, she'd get it on with him. Well, he turned out to not be a kid. It was some semi-retired guy, way over weight, and totally not gonna happen. So we paid the $15 bucks for the pizza, and ordered another one from a different place. The second guy was a kid, maybe eighteen or twenty years old tops.
My wife looked the kid up and down and decided that he would do. She let him in, paid him, and pretended to need help with her zipper. Okay it was lame, but a youngster with the usual raging hormones isn't likely to pick up on it, or care much either way regardless.
My wife was wearing a demur blouse, black, and a gray mini-skirt. Somehow the combination accentuated her dark red hair. She wore no stockings and her panties were the standard, full size white kind so in favor by Catholic school girls. If the kid shut up and did what he was told; he was going to get the chance to take them off of her. Jana rarely wore any makeup, but her perfume was the man-killing kind: she smelled great, always. He helped her with the zipper. Jana let the skirt flutter to the floor and stood there waiting for the kid to say or do something.
He just stared. He seemed fixated. Well, so was I; Jana is very pretty, in spite of her 37 years, that especially with only her panties and blouse on.
"I have to know," she said, "do you think I'm pretty?"
The kid just nodded. He was acting almost zombie-like.
"Well, that's very kind of you," she said, answering his nods. "My husband doesn't think so. He thinks I'm old, I guess."
"Ma'am, he's nuts." Said the boy so sincerely that it was all Jana could do to contain herself.
"He hasn't made love to me in months," lied Jana. I'd banged her three times the night before; I couldn't get enough of her. Nevertheless, lies or not, the kid was responding. The bulge in the front of his pants meant that he was already lost. Jana noticed it too. "You can have me if you want," she said.
The boy advanced slowly toward her. Even so he nearly tripped over the leg of a chair. He reddened. He seemed afraid that he had broken the mood by his clumsiness. "Ma'am, I never..."
"Your first time?" said Jana.
"Yes, ma'am," he said.
"What's your name?"
"Well, Carlos, I would be honored to have you do me and be your first piece of ass," said Jana. She reached out and felt his penis through his pants. I saw her eyes widen when she realized the size of the kid's tool. "You are a big boy aren't you," she said.
The boy extended his hand toward Jana's breast and touched it. When she didn't flinch he extended both hands and began gently exploring both of them. Jana closed her eyes and let him discover her. Soon his hands were tracing their way down the sides of her arms and onto her butt. He pulled her to him and kissed her neck, then her cheek, then her lips and she let him.
"You've kissed girls before haven't you?" teased Jana.
"Uh—yes ma'am. It's just—well—I've never been—you know—naked with a girl."
"It's okay. I think it's exciting to be a boy's first," she said.
"Really? You don't think I'm a..."
"You're fine," she said, putting him at ease as well as she could.
For my part, I was in the closet seated on a stool—naked. The boy might have been fine, but I sure as hell wasn't. I was mad dog jealous! Jana had wanted me that way, so that was the way it was going to be. She had also left me strict orders not to touch myself; she wanted me to take her when the pizza guy had finally gone. I was, however, having a devil of a time trying to keep my word. I did keep it, but next time she had to let me play with myself; she just had to. Geezsus! What was I saying, next time. There wasn't supposed to be a next time. The thought of going through this again was actually making my Johnson wilt; it was scary!
She unbuckled his belt. Soon she was going to see exactly what it was he had in there. She unzipped his trousers and pulled them down around his knees. The bulge in his briefs was intimidating. She peeled them down and a ten-inch cock sprang out and brushed her face.
She'd fallen to her knees to pull his briefs down. His cock was at her eye level. She stared. The purplish glans looked like an enormous mushroom; it even impressed me. Jana kissed it, then licked it; the boy Carlos jerked spasmodically at the unfamiliar intimacy. I didn't blame him; I was rock hard just watching them. Jana stole a glance in my direction, a gleeful smile briefly framed her lips. Her hands encircled his rod and stroked it up and down once or twice. She leaned forward, taking the tip into her mouth; she began to suck it, slowly, methodically. Carlos, for my money, was the luckiest cat in town right at that moment; that in contrast to the "jealousiest" cat in town—me!
The boy grabbed the back of her head: a brute male controlling his she. When he came in her mouth, he shuddered like he had been electrocuted. White foamy stuff dribbled from the side of my wife's mouth and her lover collapsed backwards onto the bed. Jana stood and began stripping her remaining clothes off. Her back was to me now, and when she pushed her panties floorward; I had a perfect view of the prettiest butt in the whole wide world! She glanced over her shoulder at me and mouthed a teasing kiss in my direction; I almost fainted from the eroticism of it.
She crawled up onto the bed next to the boy-man who would conquer her. He wrapped his arms around her diminutive form and whispered something to her that I couldn't hear. I couldn't hear it, but I could well believe that he was telling her what an idiot her husband was for not treating her a whole lot better than he had. I was sick with jealousy by now. I was close to bursting from the confines of my self-imposed prison and booting the youngster's butt outta there and taking over where he had left off. But, gritting my teeth, biting my tongue, and hating myself more than words could express; I didn't. I stayed right where I was and waited impatiently for the second act. I didn't have to wait long.
"You are wonderful," said the boy. "I never..." He began to cry. I wasn't sure if it was out of gratitude for my wife giving herself to him or relief that he was finally going to be able to do a girl. It was probably a mix of the two; in fact, I'm sure it was.
Jana comforted him, kissing his lips like the understanding woman she was. "Touch me," she said. "Touch me all over."
He started to feel her up. Her breasts, her buttocks, her belly, and finally her mound. Jana had a completely bald mound; it was exquisite. Carlos shimmied down her body and kissed her slit. She oohed and aahed and twitched as his tongue penetrated her most secret places. His right hand insinuated itself under her butt, and I could tell his finger was probing her anus. She raised up for him to be able to better push it inside of her, then she settled back down impaling herself in the process. I knew his finger was in her from her initial grimace that bespoke the slight pain of the unfamiliar object violating her bowels.
"Take me now, Carlos, I need a good screwing and I need it now!" My wife was desperate. Carlos was hard again and his cock was clearly in control of him. He rolled on top of my wife and she spread her legs wide for him. He poked inexpertly at her vagina and looked frustrated when he couldn't gain a lodgment; he really was a virgin. Jana took hold of his penis and guided it to the right place. It was all of the help he needed. He began pushing slowly but inexorably into her. Her subdued cries were hardly noticed by her assailant.
Carlos grunted and mooed more than Jana had the first time I had taken her seventeen years before. Well, a virgin is still a virgin regardless of their sexual equipment I guess.
.... There is more of this story ...