The further humilation of a sissy boy

Greg scrambled to get everything just right. He set up the poker table his wife had recently bought for such an occasion as this. He made sure all the hors devours were cooking properly and he checked to see that all the drinks were chilled. Once that was all checked he hurried to Jaclyn’s room to prepare her outfit for the evening.

Jaclyn had been planning this get together for a couple weeks, and she told Greg everything had better be perfect. He had assured her that he would not let her down. Jaclyn’s four closest friends were coming over for an evening of poker, girl talk and alcohol induced fun.

Greg was laying out her outfit when the standard call arrived. Jaclyn was leaving work. Greg knew that meant he had approximately 15 minutes until she arrived. He placed everything she had asked for on the bed and checked on the food one last time before moving to the chair by the front window. He stared out the window until he saw Jaclyn’s SUV turn into their cul de sac, at which time he rushed to his kneeling position just inside the front door. He was waiting in his usual attire, spiked, high heels, stockings, garter belt and thong panties, all in matching pink. A moment later the door swung open and Greg’s sexy plump wife breezed in.

“Good evening my Love.” Greg said staring up at her.

“Hello Gregory.” Jaclyn replied aloofly.

“How was your day?”

“Alright I guess.” She replied, dropping her brief case and jacket next to him as she walked by.

Greg didn’t move as quickly to pick up her things as he usually did, and Jaclyn noticed. She stopped a few steps from him and turned around to see what was going on.

“What?” she said with w snip in her voice.

Looking up at her with his pleading eyes, he said just one word, “Please?”

“Oh, alright.” She replied, dropping her head back with a bit of contempt.

Greg suddenly had a grin from ear to ear.

Jaclyn walked back over to him and lifted her skirt up to her hips. Her fat hairy snatch was uncovered, a sure sign to Greg that she had been naughty at work. He extended his tongue and immediately began lathering her pussy with it. He could tell his assumption was right, as the taste of male cum assaulted his taste buds, causing him to lick faster.

“That’s Seth’s cum pussy boy.” Jaclyn told him as she watched her husband clean the remnants of her noontime fucking from her juicy cunt. “He came to the office today and gave momma a good hard fucking with that big dick of his.”

Greg’s mind raced with images of his wife being pounded in her office by the hunky young stud. He continued to devour Jaclyn’s love canal, and his little cock grew painfully in his spiked chastity device. He licked deep and he licked long. He sucked on her clit and flicked it with his tongue. Jaclyn reached down and spread her lips with her fingers and raised her foot up to place it on a can near the door. This gave Greg better access to her dripping pussy and he took advantage, sliding his tongue up deep inside his sexy fat wife.

“Some of his spunk dried on my thigh, Cupcake, be a good little slut and clean that off for Momma.” Jaclyn quipped. She just loved the feelings she got when she treated her little sissy boy husband this way.

Greg did exactly as he was told, using his teeth and tongue to dislodge the crusty fluid from his wife’s thick thigh. Having succeeded, he returned to her pussy and again devoured it eagerly.

Jaclyn was really getting into it when she realized there that time was short. Pushing him away, she told him, “That’s enough wimp; there will be enough time for that later, go run my bath.”

Greg stood up, put Jaclyn’s brief case away and hung up her coat before running off to the mater bathroom to run her a bath. He reflected on what Jaclyn had said. He was excited about the party. All of Jaclyn’s friends knew of their relationship, and Greg knew he would be passed around like a bottle of wine in a group of teenager, pleasuring probably all of them with his tongue.

When the bath was ready he beckoned his wife. He undressed her and bathed her full sexy body, and then watched as she douched herself just before getting out. Greg lathered her body in her expensive body cream and helped her dress, the whole time his teeny-tiny pecker was hard and painful. He excused himself to tend to the food and Jaclyn finished by styling her hair. Even though only the girls were coming over, Jaclyn felt she had a reputation to uphold as a beautiful, sexy, confident, full figured woman.

She arrived downstairs after two of her friend, Jenny and Willa had already arrived. The three women squealed with delight upon seeing each other, and all hugged. Greg had prepared the women’s drinks, and before Jaclyn could even ask, Greg was already preparing her dry Apple Martini. The girls all retired to the living room as Greg finished with the prep work. Rachel and Sophie arrived within minutes of each other and as soon as Greg had made them a drink, the ladies all sat down at the table to play.

Greg brought the food and drinks like a good little waitress as the ladies played poker and chatted about life.

“Gregory my little wimpy boy, Willa needs her drink freshened.” Jaclyn would state.

“Right away my Dear.” Greg would reply, hurrying off to get her a refill.

“Thank you sweet cheeks.” Willa said to Greg as she smacked him on his exposed rear when he placed her drink in the cup holder of the table. Greg liked Willa a lot, so the attention found him aroused and of course in pain.

Sophie was not so flippant with her attention. After asking for another drink, she slowly rubbed his ass cheeks with her hand, caressing it oh so kindly. “You told me you like to fuck your little pussy boy in the ass with a big fat strap-on right Jackie?” Jenny asked.

“Oh yeah.” Jaclyn replied. He really likes it, Jen. Don’t you, Babydoll?”

“Yes my love.” Greg replied. He was enjoying the attention, and he could not help but stare down ah the abundance of cleavage Jenny was displaying with her 38D’s

Sophie ever so subtly moved Greg’s thong to the side and slowly inserted one of her pudgy little fingers to the second knuckle. Greg grunted a bit, since she had no lube on her finger, but as she worked it in and out a bit, wiggling it as well, he began to enjoy it. His little penis was rock hard and being tortured by the cock cage.

“How big is your dildo Jackie, because he doesn’t seem to be having any problems accepting my entire finger?” Sophie announced.

Greg could feel it worming deeper in his ass, and he moaned his approval.

“You are so cruel Jenny.” Rachel admonished her. “Leave the little guy alone. Besides, my drink is low and I need a refill.”

“You’ll just have to wait, won’t she Gregory?” Jenny asked him as she continued sliding her finger in and out of his asshole. “You’re enjoying Miss Jenny’s finger aren’t you?”

“Yes, ma’am.” Greg said breathlessly as he wiggled his tight little ass trying to get more of Jenny’s finger.

“Are you in or out?” Sophie barked, trying to resume the hand of five card draw.

“I’m in.” Jenny replied. “Here hold my cards, sweetie.” She said handing Greg the cards. “I’ll take two.”

Greg grabbed the three remaining cards and bend over to retrieve the two that Sophie had tossed across the table. This, of course, gave Jenny a little more access to his ass, and she took advantage, sliding another finger in along side the first. She grabbed hold of Greg’s little nut sack as well and began massaging his swollen little sperm keepers as she worked her fingers in and out. Greg could hardly stand, let alone concentrate on the game.

“What do you think wimpy man? Should we play or fold.” Jenny asked the tormented little man.

Looking at the cards he saw she had only a pair of kings, an Ace, a 2 and a 6. “I think you should fold Ma’am.” He barely got out.

“Fine. We’re out.” Jenny announced.

Two others made bets and laid down their hands. Willa won with a pair of 9’s

“We could have beaten that!” Jenny snapped, pulling her fingers from Greg’s ass-hole. She smacked his ass hard as if scolding a child. “No more fun for you. Go get Miss Rachel her drink you useless bitch.”

“Hey! Easy!” Jaclyn snapped at Jenny. She wasn’t about to have her friends treating her bitch like that, only she could do that.

“Sorry Jackie.” Jenny apologized. “You know how I hate to lose, and he made me lose.”

“Well play your own cards next time.” Jaclyn told her.

Greg returned with Rachel’s drink and another plate of hors devours. The ladies all chuckled at the red hand print on Greg’s ass and they went on with their game.

All of Jaclyn’s girls were large like her, not quite as big, but also not as sexy. So the food disappeared in a hurry. Greg was in a constant state of arousal with all the big round asses and tittie flesh flashing all around him. He was kept running back and forth to the kitchen for drinks and food. He could hear the conversation, and it was getting cruder as the alcohol disappeared. Finally Greg heard Jaclyn describing her night with Seth and Josh. The game had stopped and Jaclyn had the ladies hanging on every word. She was telling about the part when one was fucking her ass and the other her pussy, when she noticed Willa had her hand under the table, and appeared to be pleasuring herself.

“Willa, are you fingering yourself?” Jaclyn asked her.

All eyes turned toward Willa.

“No!” She defended herself.

“You were too.” Jaclyn debated.

“I was not!” Willa protested.

“Babydoll, take Willa’s hand from under the table and smell it.” Jaclyn ordered Greg

“He will not!” Willa snapped.

“See, you were playing with yourself.” Jaclyn told her.

“Alright, alright, I was, so what.” Willa gave in. “I can’t help it, you are such a little slut Jackie, and it just turns me on to hear your stories.”

“That I am, Willa. That I am.” Jaclyn replied. There is no need to be embarrassed. That’s what my little pussy boy is for. No need to do it yourself when we have his tongue to help.”

Jaclyn just looked at Greg, and he dropped to his knees and crawled under the table. It was not long before the moan came from Willa’s mouth as Greg’s tongue touched her dripping pussy. He really liked Willa. She was everything he loved in a woman, a little on the plump side with big tits, a big round ass and a bit of a naughty side, so he enjoyed every moment. She grabbed his head and began guiding him around her aroused sex. Greg eagerly licked and sucked her fat juicy cunt, paying close attention to her larger than normal clit. He sucked it like it was a small little cock, and Willa squealed appreciatively. She squeezed her fat little thighs around his head and then forced his head into her harder. She lost herself in the moment. Greg was enjoying it as well.

“Now, where was I?” Jaclyn asked, noticing that Willa wasn’t paying attention anymore.

“Seth was fucking your ass, and Josh was fucking your pussy.” Rachel told her.

“No, it was the other way around, but I digress.” Jaclyn quipped.

She continued the story and not two minutes later, Willa was screaming with pleasure as her orgasm consumed her. She bucked and her plump little figure jiggled with delight. Greg licked and sucked the whole time her orgasm rocked her body. Her cum flowed and it covered his face. He loved it when a woman would cum all over his face like that, and he just licked it all up

Before she was even done, Jenny was pulling her pants off and screaming, “I’m next. I’m next!”

Greg crawled between Jenny’s plump thighs and began to pleasure her as Jaclyn wove the tapestry of her sexual tale. Jenny shaved her pussy, and her juices along with Willa’s that covered his face made for a very slipper meeting of the flesh. Greg’s tongue reached out and parted Jenny’s lips and Greg relished the feeling of his slick face against her slippery smooth snatch. Jenny didn’t help Greg as Willa had; she just slid down in her chair and opened her thick thighs as wide as she could. She opened her blouse and began massaging her fat, soft tits through her bra. She also didn’t lose herself in the moment, still paying close attention to Jaclyn words as she continued her story.

Under the table, Greg was eating her pussy like a man on a mission. He licked her thick plump pussy lips and plunged his tongue deep inside her burning hole. He wrapped his arms under and around her thighs and began tongue fucking her. In and out, in and out his tongue repeatedly violated Jenny. Soon she was moving in rhythm with him. She pinched her own nipples roughly, trying to coax her orgasm to the surface. A moment later, Greg switched his attention to her clit. He sucked it in hard and nibbled on the very tip of it. This was very arousing to Jenny and she gasped with delight.

“Ooh, ……….yea,……… that again sweetie. I liked that.” Jenny coached Greg.

Everyone turned to look at her. Noticing it, Jenny instructed Jaclyn to continue.

Greg did the same thing several times quickly and he pushed Jenny over the top. She announced her orgasm to the whole table as she mashed her tits hard between her hands and her body. Greg just rode the bucking bronco again as Jenny’s body duplicated what Willa’s had done just a few minutes earlier. Jenny eventually collapsed on the chair in a haze of bliss, and Greg raised his head from under the table and looked at Jaclyn.

“Anyone else?” Jaclyn asked the group.

By now no one even cared about the card game and each of them was either listening to Jaclyn’s story or recovering from an orgasm. Rachel said she would have a go, but she directed Greg to the nearby couch, lifting her skirt up before sitting down to reveal she had no panties on at all.

“No panties Rach?” Jaclyn asked in a motherly tone.

“Don’t get all holier than thou with me Jackie. We all know your pussy is bare right now too isn’t it?” Rachel retorted.

Jaclyn just gave a big smug grin.

Rachel was not as sexy as the other girls. She was once a skinny girl, but had gained a bit of weight, leaving her with a large flat ass. Plus, her tits were not nearly as large as the other women’s. She spread her legs and Greg somewhat reluctantly began his duties. He knew he had no chance of getting out of it, so he did what was expected. He wanted it over as quickly as possible, so he doubled his effort, thinking he could rush her ending quickly. Rachel noticed his sense of urgency and took it as his eagerness to please.

“Look Jaclyn, he must really want my pussy badly.” Rachel bragged.

This made her feel sexy and it made her tingle all over. Greg sucked and flicked her clit hard and fast, and like he had hoped, soon Rachel was singing his praises as her orgasm enveloped her. Greg quit licking the moment he heard Rachel scream that she was cumming, and looked straight at Sophie hoping she would want some too.

See, Sophie was Greg’s favorite one of Jaclyn’s friends. She was thick but not fat like her other friends. She was a bit taller than the rest, and she wore clothes like Jaclyn did, that hugged her bulky figure. But it was her double D tits that always got his attention. He had never seen them exposed, but he imagined they were spectacular. They seemed to ride higher on her chest than the others, even Jaclyn’s. Her ass was always filling out her skirts and pants so sexily that Greg almost felt guilty at how he lusted after her. He wasted to see Sophie naked so badly it hurt. He stared at her waiting for her approval, but was surprised by her answer.

“None for me pussy boy, but I will give you another little surprise.” Sophie teased him, standing and lifting her skirt ever so slowly. “Your wife tells me you like silky panties.”

Greg nodded excitedly.

“She also tells me you are quite the dirty little panty sniffer.”

Again he nodded as he saw her silky royal blue panties come into view.

“Well then come on over and sniff mine.”

Greg crawled over to where Sophie was sitting back down at the table and she scooted down in her chair so her ass was almost off the edge. As he got close, he could see there was a dark spot between her legs, no doubt from her pussy dripping with excitement. Greg dropped his nose to her crotch and inhaled deeply. The scent was intoxicating. The distinct smell of female arousal assaulted his senses. He moved his face around in small circles enjoying the feel of the silky material against his skin. His little pee pee was so hard he could hardly handle the pain it was in, but he ignored it and enjoyed the smell of “his” Sophie. His disappointment over not getting to see her naked evaporated like smell of her pussy did as it crawled up his nostrils.

“You like Sophie’s scent?” Sophie asked, pulling him away from her panties.

“Oh yes Ma’am.” Greg replied.

“Do you like Sophie’s silky panties as well?”

“Yes Ma’am!” he answered passionately.

“I tell you what you little wimpy man. You can keep them for a few days, but I want them back, and I want them clean when you give them back.”

“Yes Ma’am, Thank you Ma’am.” Greg said. He was so excited as she hooked her fingers in the undergarment and began to pull them down. He was sure he would get to see her bare pussy. However, Sophie was careful to let her skirt fall as she lowered her panties, revealing nothing to anyone, including Greg whose face was only inches from Sophie’s pussy. She handed them to Greg and he immediately placed them against his nose and inhaled again. He rubbed the soft silky material on his face, arousing him even more. He sniffed them again as Sophie walked away calling him a pathetic wimp under her breath.

Greg was enjoying his gift when Jaclyn broke his pleasure, “Cupcake, if you like Sophie’s panties so much, why don’t you take yours off and put hers on.” Jaclyn told Greg. She knew he would not like this idea, because that meant he would not be able to smell them and enjoy Sophie’s scent.

“But they don’t match.” Greg said trying not to argue, but trying desperately to not put them on.

“That’s ok, Momma doesn’t mind if you don’t match this evening.” Jaclyn replied.

“Yes, my love.” Greg returned, as he disappointedly pulled his pink thong down. He took one more sniff of the sexy undergarment before pulling them over his slim hairless body. They were bikini style, so they hugged his slim little ass and covered his cock cage nicely. He did have to admit he liked the feel of the soft, fine material.

“I have to use the bathroom.” Jaclyn announced. “Loverboy, freshen everyone’s drink so we can get back to the game.”

“Yes Dear.” Greg said, grabbing all five glasses and heading to the kitchen. “I’ll join you,” Jenny told Jaclyn.

Jenny stood in the vanity area as Jaclyn did her business, and she did the same as Jenny relieved herself. The ladies were both standing at the mirror primping when Jenny said, “Jackie, I think I’m gonna get out of here.”

“What?” Jaclyn asked, “Why?”

“Well, your story and Gregory’s tongue has me all worked up, I think I’m gonna go call Tony, and get me some big, fat, Italian dick.”

“Come on Jen, you can do that later, don’t break up the game, it won’t be as fun with just four.” Jaclyn argued.

“I’m sorry, sweetie, I can’t wait I gotta have some dick and I gotta have it soon.”

By :

Check Also

Discovering a wet fetish

It was summer. And time for our annual extended family camping trip. We’d done it …

Leave a Reply

Your email address will not be published.