Mary had spent weeks stretching Tony’s asshole with anal dilators in preparation for pegging him. What she didn’t tell him until it was too late for him to back out was that he was going to get pegged in front of an audience. Amy, their sex therapist, was hosting a ladies-only event, and Tony was going to be the main attraction. Five women, with Mary as one, would participate and observe Tony being punished in humiliating situations. Everyone would be wearing masks.
Since he learned he was the main event, Mary noticed that Tony had been paying more attention to his body. He was eating healthier and exercising more, even working with weights. Tony wanted to look good naked in front of other women.
For the event, Tony would be named Jack, and Mary would called Lady D or D. The other ladies would be named Lady A through Lady E. Each of the ladies had paid for this entertainment, or, more accurately, their husbands or providers had paid. Several were essentially trophy wives. They weren’t always happy with their lot in life, and they would take it out on Jack. Each of the ladies drew their assignment from a fish bowl. The draw was fixed, so D drew pegging Jack. The ladies, Mary (or should I say Lady D), and Amy were all seated on sofas in a large living area. Champagne flowed freely; everyone (except Mary and Amy) was a little loose and giggly. No men were present, but cameras around the room allowed their husbands or loved ones to view the entertainment.
Amy started the ceremony. “Ladies, you know you are being viewed by your husbands or loved ones. They deserve some titillation since they paid. Let’s make this an outstanding event for them, as well. Tops off.”
Amy didn’t really care if the men were entertained. She had plans for Mary and wanted her to get used to being naked in front of others.
Lady A was wearing a wrap-around dress that was tied at the waist. She wore no bra, and her nipples were clearly visible. She untied the dress and let it fall to the floor. Under the dress, she wore a seamed hose, a garter belt, and panties, all black. Lady A was the youngest of the group and the only single lady. Her stepfather had paid, so it was assumed she had been abused for some years.
Lady B wore a man’s silk Hawaiian button-up shirt with Daisy Duke shorts belted with a lightweight, wide belt. Lady A obviously knew B since she walked to her and unbuttoned her top. They then kissed each other on the lips. Lady A then kissed each of Lady B’s nipples. “Tasty, my sweet.”
Tonight seemed to be Lady C’s first time attending such an event. She was older than the other ladies and had had no cosmetic surgery. Her breasts were full and natural and hung just a bit. She was just a bit plump. She wore a conservative red polka dot long-sleeve blouse and black skirt. She hesitated, unbuttoning her top and placing it on the sofa behind her. She slowly undid her bra and put it with her top. She left her skirt on. Lady A asked, “Would you like a kiss, dear? You have lovely nipples, and I’d love to get you in the mood.”
“No. No, I think I’m fine.” She seemed to blush at being half-naked in front of others. Lady A just smirked.
Lady D hesitated, but Amy nudged her and said, “Go ahead. You need to be part of the group.” D took off her top, undid her bra, and slipped it off. She was tempted to cover her breasts but knew that wasn’t the right thing to do. It was the first time D had exposed her breasts to someone other than her husband or doctor.
It’s time to get started. Lady A stepped in front of Jack, roughly grabbed his crotch, and squeezed until Jack grunted and bent forward. “You men think you can just grab us by the pussy, but tonight is our turn.” She unbuttoned Jack’s shirt and slipped her hands up to pinch his nipples. She finally let his shirt drop to the floor. She unbuckled his belt, unbuttoned his pants, pulled down the zipper, and slapped his ass. Hard. “Who’s the bitch now?” She then focused on his genitals. “Damn, that’s a puny penis!” She slapped his ass again, even harder.
Lady A seemed to be putting on a show for the ladies present and the men watching. Lady A’s behavior was all fine with Amy. Since everyone was masked, had signed nondisclosure agreements, and signed a “model agreement” that allowed Amy to sell the videos, it was all good. Lady A was done and stepped back to let B take over.
B gently rubbed Jack’s nipples, circling them to arouse them. She grabbed both of them by the tip, pinched, and twisted until Jack grimaced. She kept this up for at least half a dozen times. Once his nipples were hard, B put a nipple clamp on each. She squeezed the clamps to make them momentarily tighter. Jack grunted and moved forward trying to relieve some pressure. B lightened up. A chain connected the clamps. B hung a weight on the middle of the chain.
“Jack, lean your hands on the edge of the table. Step back about two feet. We want to watch your nipples and cock sway as you’re spanked. I also wanted to put weights on your balls, but Amy said, “Not this time. Don’t raise up while you’re spanked, or the timer will restart.”
Lady C walked to Jack’s left. Amy started the timer for two minutes. Lady C playfully smacked Jack’s bottom. “Boo!” shouted Lady A. “That will never do. Now, C, put all your strength behind it. Think of how your husband mistreats you and take it out on Jack. If you don’t do it properly I’ll take over. Restart the timer!”
Amy restarted the timer. C brought her arm back and spanked Jack as hard as she could.
“That’s better, C; keep it up, but harder and faster. The clock’s running. Don’t forget his right cheek.”
C did her best, spanking as hard and fast as she could. Jack was grunting but easily handled it. However, his ass was a lovely shade of dark pink when C’s time was up.
Lady D removed Jack’s nipple clamps and squeezed his nipples before she moved back. Amy stepped in to lube Jack’s asshole. She spread a generous amount of lube on his hole and pushed a finger in. Jack was loose enough that Amy decided to add a second finger. She looked to Lady D and whispered, “You’ve done a good job. He’s stretched enough for you to peg him.”
D took off her skirt and panties. She was embarrassed but knew she had to do it to get into the strap-on. Amy handed her a strap-on with an anal dildo for Jack and a vagina plug for her. D was going to enjoy this. D lubed up the dildo and placed the head at Jack’s asshole. She slowly entered Jack and began to pump in and out. Everything about the entire evening had turned her on, and she quickly orgasmed. She slowly pulled out of Jack’s ass.
Lady A was disappointed, “Too quick! One of us needs to take over.”C held up her hand and yelled, “Me, me!” She had gotten into the spirit of the evening.
Lady A was so surprised that she could only say, “OK. D, take off the strap-on and help C into it.”
D sneaked a look at Jack to make sure he was OK with this. Jack smiled and nodded. D then took off the strap-on and helped C into it. D added extra lube to the dildo and the plug. C may as well enjoy this.
C did enjoy it. She fucked Jack’s ass like her husband had fucked her. She slapped Jack’s ass and said, “How’s this, slut!” C kept pumping, “Oh shit! Fuck!” C came quickly. She pulled out, rubbed Jack’s ass, and whispered, “I’m sorry, Jack. I hope you’re OK.”
Lady E turned to face the other ladies, “I’m supposed to give Jack a hand job, but I’m not going to do it. It doesn’t seem right that one of us gives him pleasure. Tonight is all about us. Therefore, he’s going to have to finish himself off for us. Tony, I’m giving you a towel so you don’t make a mess. I’ll drip lube on your cock to make this easy for you. Do a good job and give us a show.”
Lady A says, “Oh no, that’s not good enough. This cunt’s ass is barely pink. C did her best but still only did a piddly job.” Lady A pulled B’s belt out of its loops and folded it in half. It wasn’t a heavy belt. “We are going to take turns belting his ass until he comes. Don’t dally, Jack, or this will really hurt.” Lady A pulled back and gave Jack two belts. Jack now had two red belt stripes across his ass.
Lady A pulled er arm back for another stripe, but Amy grabbed Lady A’s wrist and said, “I think two belts each should be good enough.”
Lady A handed the belt to B. “Give it to him good.”
B gave Jack her two belts. Jack’s ass was starting to turn bright red. B handed the belt to C. B smirked, “Don’t disappoint us, or maybe we will belt you next!”
C did her best, but it paled compared to Lady A’s efforts. C gave D the belt. D (or Mary) didn’t know what to do. She had never belted or even spanked Jack (or Tony) before. But she had gotten in the mood of the evening. She took the belt and struck Jack harder than even Lady A.
Lady A was delighted, “Yay! Good job. You’ve made us proud, D. You started the evening slowly but ended strong.”
Finally, D handed the belt to E. During all the belting, Jack had been furiously stroking his cock. He didn’t want the ladies to go another round on him. E waited just a bit because she knew Jack was close. But she wanted to get her belts in. She drew back and struck the back of Jack’s thighs as hard as she could. She repeated the strike and stood back to admire their handiwork. “Very pretty.”
Jack squirted over the towel he held in his hands. He carefully wiped his cock.
The show was almost over. Each of the ladies put their bras and tops back on. Lady A stopped them from leaving, “We must show Jack our appreciation.” She moved in front of Jack, pinched and twisted his left nipple, slapped his breast, and said, “Thank you for a lovely time. Amy, let me know when Jack is performing again.
Actually, I’d like a private session with him and a paddle or cane. Let me know.”
B took Lady A’s place and did the same but to Jack’s right nipple. Each lady followed. D let Lady E go before her so she would be last. She stood in front of Jack, grabbed a nipple in each hand, pulled, and twisted as hard as she could. She then spanked both breasts at the same time.
All the ladies were leaving. Lady A told B, “Come with me, B. Amy reserved a room for us. I’m still up for more spanking, and I know what a fine ass you have.”
None of the ladies noticed Lady D stayed behind with Amy and Jack. “Tony, that was wonderful! Did you enjoy yourself?
Tony answered, “Yes, I did, Mary. But maybe it’s my turn to turn your bottom red. If you’d like.”
“But Amy is still here!”
“Yes, she is, and I’ve asked her to get Jane so you could have a small audience.”
Before Mary could respond, Jane rushed in. She was wearing a long kimono. “Oh, Jack! I watched it all on a monitor. I loved it. I was so naughty. I started fingering myself as soon as you were naked.” With that, she undid the belt on her kimono and let it drop to the floor. She moved to Jack and maneuvered him to sit on a sofa.
“You need to spank my naughty bottom. I’ve been so nasty and orgasmed twice.” She lay over Tony’s lap. “Spank me now, Tony.”
Tony didn’t hesitate. He started lightly but soon increased the strength. Right cheek, left cheek. He spanked from her bottom to the top of the back of her knees. Finally, Jane said, “Stop.” Tony thought she had had enough, but she said, “Amy, please hand Tony a paddle.”
Amy went to a cabinet, opened it, and selected a paddle. She handed it to Tony, and he started again. At long last, Jane began to cry but never said stop. Tony finally said, “Enough.” He started to gently rub her bottom.
“Oh Tony, that was wonderful. Thank you so much. I think it’s now Mary’s turn.” With that, Jane got up and moved to Mary. She started to unbutton Mary’s blouse but moved close to her ear and whispered, “Are you OK with this, Mary? We won’t do anything you don’t want to experience”. Mary glanced at Tony, who was smiling. She nodded her head. Jane returned to undressing Mary. When Mary was naked, Jane moved her to Tony’s lap. She bent near Tony’s ear and whispered, “Not too hard. It’s her first time.”
Tony whispered in Mary’s ear, “Are you sure you’re OK with this?” Again, Mary nodded.
Tony started very gently spanking Mary’s bottom. Mary was disappointed and said, “Harder, Tony! I want my bottom red!”
Tony complied, and Mary’s bottom soon turned a lovely shade of pink. Tony stopped as soon as Mary’s bottom was red. He didn’t want to overdo it the first time. Jane came over and dripped lube on Mary’s rosebud. Tony rubbed his left-hand index finger around her asshole and gently pushed in. Jane knelt down, reached under Mary, and started to gently rub her clitoris with her left hand. Mary raised up to give Jane better access.
Tony slipped two fingers into Mary’s pussy. Jane reached under D’s chest and began to massage her breast. Mary got up on her forearms so everyone had full access. Tony touched fingers between Mary’s anus and vagina.
Tony rotated his hand and started to massage Mary’s G spot. With both Jane and Tony making love to her, it didn’t take long for her to orgasm.
Once Mary came down from her orgasm, Jane asked, “Don’t you think we should thank Tony? We’ll give him a two-girl orgasm.”
Jane and Mary gave Tony a two-girl blow job. One on each side, they licked his shaft, meeting at the head of his cock. After doing this several times, they kissed each other. Jane held Tony’s shaft and fed it to Mary. Mary sucked like a pro. Jane gave Mary some time and then said, “My turn, my turn!” Mary moved Tony’s cock to Jane’s mouth. Jane sucked Tony like a pro. All this spanking, fingering, and love was too much for Tony. He soon came shooting cum on Jane and Mary’s faces. The girls giggled and swallowed all that got into their mouths. They took turns licking cum off each other’s faces.
No one noticed when Amy left the room. She never had sex with her clients.
Jane looked at Mary and said, “Everyone got a two-person orgasm except poor, little, ole me! Don’t you want to give me oral pleasure while Tony makes love to my lips and tits?”
“But Jane, I’ve never been with a woman.”
“Don’t worry, just do what you like Tony to do to you. I’ve seen him pleasure you, and he knows what he is doing. You do want to pleasure me, don’t you?”
“Oh, yes, I do! I really do. And I want Tony to make love to your lips and tits. Sit back on the sofa next to Tony.”
Jane sat back and spread her legs. Mary placed a pillow between Jane’s legs on the floor and knelt down. “Tony, kiss her and fondle her breasts.”
Tony was glad to hear Mary give him directions. It confirmed his suspicion that she wanted a threesome, especially with Jane. Tony began kissing Jane. Jane still had some of Tony’s cum, so it was a new taste experience for him. He kinda liked it. Jane was clearly ready and returned his kisses. Mary began kissing Jane’s inner thighs, moving up to her pussy. When Mary reached Jane’s pussy lips, Jane pushed Tony’s head down to her tits. Tony licked, sucked, and gently nibbled Jane’s nipples. As Mary began licking from the bottom of Jane’s pussy up to her clit, Jane told Tony, “Bite harder, Tony. I like it a little rough.”
When Mary slipped two fingers into Jane’s cunt, she couldn’t hold back any longer. She began to cum and squirted onto Mary’s face. Mary had only seen women on porn squirt, so she was initially startled. Still, as she quickly recovered, she began licking up Jane’s squirt.
The room smelled like sex as it should. All three sat on the sofa and recovered. Tony went and got glasses and champagne. Tony toasted, “Here’s to beautiful women and wonderful times.” Tony and Mary finally left, but not until they promised Jane they would be seeing each other again. Soon!