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The Second Cup

Category: Group Sex
10.02.2018
BadFairGoodInterestingSuper Total 0 votes
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“Here you go Hon,” Rachel said as she handed me the bright red thong her friend Karen had ‘loaned’ me. “All clean and ready to go.”

One by one, memories of both the previous day and night flooded my mind and started my cock stiffening. Getting caught wearing panties by Karen. Spending the morning in nothing but panties in front of my wife’s best friend. Rachel rubbing a pair of panties against my body as we screwed.

Finding out the panties were not hers but her friends. Of course, the best part was seeing Rachel holding the panties to her face breathing her friend’s scent, and then licking Karen’s juices from the crotch.

“So are you going to put them on?” She asked. “Or are you just going to stand there with a boner fondling my girlfriends’ underwear?”

In a flash, I had my shorts off and was sliding the silky thong up my legs. A moan escaped my lips as I stretched them over my rock hard erection.

“They look good on you.”

“They feel good,” I admitted, gently rubbing the material over my cock. “So what time are we supposed to be at Karen’s?”

“We aren’t going to Karen’s,” Rachel said. “We are meeting her at Giovanni’s in a half hour.”

Giovanni’s was a fairly large, yet dark and intimate Italian restaurant, not too far from where Karen lived. It was the kind of place where you went for special occasions, a special anniversary, marriage proposal or important first date. I wondered what was going on, but I decided to stay quiet and let the evening play out, however the girls wanted it to.

Rachel’s hand never left my crotch during the drive over. Slowly and gently she stroked me until I was at the edge of Cumming, holding me there in a sort of erotic suspension.

“Honey, could we please pull over?” I pleaded.

“Not a chance big boy,” she laughed. “You like panties, I’m liking teasing you and keeping you hard in them. So we both win.”

Knowing that once we got to the restaurant, the owner Mama Giovanni would most likely hug us both, Rachel graciously took her hand away from my crotch to give me a chance to soften up as we pulled into the parking lot.

“Rachel, Rick good to see you again,” Mama Giovanni came over and hugged us both.

Rachel mouthed ‘you owe me’ as Mama Giovanni wrapped her arms around me.

“Karen and her friend are right this way,” she said, leading the way into the dining room.

I felt a huge let down when Mama Giovanni said Karen had a friend with her. I had been holding on to the slight hope that I was being set up for my first threesome.

“You are a lucky man tonight Rick,” Mama said as we got to the table. “It is not often you get to dine with three such lovely ladies, I’ll bet.”

“That’s me, Mr. Lucky.”

She seated us and quickly left. Introductions were made.

“Rick and Rachel, this is my friend Jill.”

Jill was stunning. Very tanned with long straight blonde hair, bright blue eyes and from what I could see, a fantastic body.

“So are you wearing them?” Karen asked as soon as we sat down.

I could feel the heat as I blushed. I also felt my cock start to stir in my pants.

I nodded.

“Good,” she smiled. “I want to see.”

“See what?” asked Jill.

She didn’t know. After Karen’s first question, I assumed that she’d told Jill. To be honest, I wasn’t sure if it was good or bad.

All I could do was sit there.

“Come on, it’s not like I want you to stand up and drop your pants. Just seeing the waistband will be good enough for now.”

I looked to Rachel, hoping she’d bail me out. When I saw the evil/sexy smile on her face, I knew I was barking up the wrong tree there.

Knowing I was beat, I slowly stood reached down and pulled the side of the panties above my pants.

“Are those what I think they are?” Jill asked.

“If you mean a red thong that I loaned him yesterday,” Karen told her. “Then you would be correct.”

“This sounds good,” Jill replied. “Do tell.”

Rachel started to tell her about the day before. As she spoke, she nonchalantly reached down let her hand rest on my incredibly hard cock. Much to my relief, Jill wasn’t in any way shocked about Rachel’s story. Her reaction was quite the opposite; she seemed to hang on every word.

Rach was midway through the story when the waitress appeared, startling the shit out of me. Rachel removed her hand.

She quickly took our orders. I jumped when, as he Karen reached over with her barefoot and started massaging my cock with her toes under the long tablecloth.

“So where were we?” Rachel asked.

“Karen was just leaving,” Jill volunteered anxiously.

“Oh yeah, so as she left, she came over and gave Rick a hug. It was so cute, the way he tried to keep his hard on from bumping into her. Karen, of course, wouldn’t have any of that and pressed herself against him.”

“You tramp,” Jill chastised, giving her a playful slap on the shoulder.

“It was the first hard cock I’d felt in months,” Karen laughed. “I couldn’t help myself.”

I jumped as she flexed her toes around the head of my cock.

“You going to make it?” Jill asked.

I managed to croak out a weak “Yes”

As she continued with her story, Rachel reached her hand back down to my lap. She didn’t miss a beat as her hand encountered Karen’s foot.

“Damn Karen,” she exclaimed. “Your feet are so soft.”

“He has a thing for feet too,” Karen explained to Jill.

“Wait a minute,” Jill stopped short. “Are you jacking him off under the table with your feet?”

“Well not exactly jacking him off,” Karen answered. “More like teasing him with my toes.”

“And you don’t have any problem with it?” she asked Rachel.

“Oddly enough, no.” Rach laughed.

“So do the three of you play together often?”

“Nope,” Rachel said. “This is the first time we’ve ever done something like this.”

“Ok,” Jill said. “So why am I here?”

“Well,” Karen answered. “As I was taking off my shorts and panties in their driveway yesterday, Rachel asked me if I was interested in giving Rick as little threesome surprise tonight.”

“I knew she hadn’t been getting any lately, so I figured it would be a fun way to help out my two favorite people in the world. Rick would finally get to experience two women at the same time and Karen…well…she would finally get laid again.”

“But that doesn’t really answer my question; am I just here to add to the tease? Or are you guys expecting me to join in?”

“I invited you because I knew you’d really dig this,” Karen told Jill, her foot and Rachel’s hand still massaging my cock. “And also because I knew you are in the middle of a dry spell even longer than mine.”

“You’ve got me there,” Jill smiled. “I haven’t been with a guy so long; I’ve almost forgotten what a real cock feels like.”

“Well, if you’re up for it, you are more than welcome to join us tonight.”

“This is so amazing,” she said shaking her head. “Shouldn’t we ask Rick if he’s interested?”

“Yes I am,” I told her almost before she finished the question.

“He is so hard,” Jill commented. “It feels like my foot is resting on concrete.”

“Mmmmm I wish I could touch it,” Jill teased.

“Easy enough,” Rachel assured her and stood up.

Luckily, the few people dining near us were either too engrossed in their meals or conversation to notice the huge tent in my slacks as I was forced to stand up and switch seats with Rachel. My erection easily overpowered the flimsy material Karen’s thong was made of and was sticking straight out from my body. All three women’s eyes were glued to my crotch as I shifted seats.

“Wow, he is hard,” Jill, commented as I sat back down.

“Go ahead feel it,” Rachel insisted.

I could tell Rachel almost as turned on as I was. The revelation that she and Karen were planning a surprise threesome was almost too mind boggling to comprehend. My over analyzing of the situation was cut short as I felt Jill’s foot brush tentatively across my lap. Instead of massaging my straining cock with her toes, like Karen. She gently applied pressure and rocked her foot side to side, pressing the silky material of the panties against me.

“Damn,” she breathed. “Doesn’t that hurt?”

“No actually, it feels pretty fantastic,” I assured her.

“I can’t believe I am sitting here in a restaurant, giving a guy I just met a foot job under the table with his wife sitting next to him.”

Jill moved her foot down so it was massaging my balls as Rachel’s hand found its way to my lap again. She ran her hand down the length of my cock until she touched Jill’s foot.

“Wow your feet are pretty soft too.”

“I just had a pedicure yesterday.”

As she said it, Jill lifted her foot until her toes were visible from under the cloth and presented them for Rachel’s inspection.

Her feet were lovely, a little on the wide side, but very delicate. Her toes were slightly long, but her toenails were cut short and painted a vibrant orange.

“Nice,” Rachel commented as she ran her hand over Jill’s foot.

Rachel had just pulled the tablecloth back over Jill’s foot and my lap when the waitress appeared, seemingly out of thin air, with our food. Judging by the looks she was giving me the girl suspected or possibly knew that something out of the ordinary was going on with our little dinner party.

We quickly ate, by that time all four of us were eager to get the rest of the evening underway. Through the entire meal, Jill kept her lovely foot on my lap continually rocking it from side to side and occasionally up and down. Like Rachel, she was nice enough to take her foot away as the waitress brought us coffee at the end of the meal, giving me a chance to get my cock under control.

As we left the restaurant, I finally got a good look at the rest of Jill. The jeans she wore accentuated her slightly large ass and muscular legs perfectly. Her tank top came to mid tummy, exposing a sexy strip of very tan skin and bellybutton piercing. A pair of multi-colored Birkenstocks adorned her feet.

Karen was wearing a mid thigh length skirt, a tank top and pair of black flip-flops.

“So Jill,” Rachel started as we walked through the parking lot towards our cars. “Did you decide if you want to join us back at our place?”

“I would love to,” Jill answered. “I have to tell you guys, all this has got me so wet. You should feel my jeans, I soaked through.”

My jaw dropped as both Rachel and Karen reached down and stroked their fingers over Jill’s pussy.

“Wow, you are wet,” Rachel told her.

I soon became aware that all three of the women were staring at me.

“Well?”

“Well what?” I asked.

“Aren’t you going to give her a feel too?” Karen asked.

I immediately looked towards Rachel, she nodding in the affirmative. My eyes then met Jill’s.

“You don’t mind?” I asked.

“Not at all,” she smiled seductively. “In fact, I would be disappointed if you didn’t.”

She then grabbed my wrist and placed my hand between her legs, grinding her crotch against my hand. They weren’t kidding, she was soaking wet it almost felt as if she had peed her pants.

“Listen up Slick,” Karen said, putting her arm around me. “You have the once in a lifetime chance to fuck the hell out of three women tonight, don’t blow it by being timid.”

“She’s right,” Rachel seconded. “All you need to do, is everything we tell you to do, I swear, you won’t regret it.”

“So shall we go?” Karen asked Jill, who was still pressing her pussy against my hand.

With a reluctant sigh, Jill pushed my hand away from between her legs. She and Karen headed towards Karen’s car, while Rachel and I went to ours.

“Surprise,” Rachel said as we left the parking lot.

“I don’t know what to say. What brought all this on?”

“Not sure,” Rach said shaking her head. “Something about yesterday really turned me on. The way Karen looked at you, having her see you hard, really got to me. It also got me wondering what it would be like to see you with another woman.”

As she spoke, I noticed Rachel was gently rubbing her pussy through her pants.

“So I guess there’s not a lot for you to say tonight,” she continued. “Other than maybe, thank you.”

“Thank you.”

The fifteen-minute drive back to our house seemed to take hours. Rachel continued to rub her pussy with her right hand and hold my cock with her left, keeping me hard as a rock. When I finally pulled into our driveway, I was ready to explode.

“I need to cum,” I told her, with an almost embarrassing desperation.

“Oh you will,” she said with her sexy-evil smile, giving my cock an extra squeeze. “Just not right now. What I want you to do is get out of your clothes.”

I started to get out of the car. Rachel stopped me.

“I mean right here.”

With Karen’s warning going through my head, I quickly started unbuttoning my shirt. Once off, I unbuckled my pants and was in the process of pulling them off when Jill appeared at the car window.

“Looks like the party is starting without us,” she mock pouted.

“No, just unwrapping our toy a little early,” Rachel laughed.

I winced as the dome light came on as Jill opened the car door. I was standing in my own driveway, clad in nothing more than my wife’s best friend’s panties with my hard cock sticking out the waistband.

“Your call girls,” Rachel said. “Should we have him keep them on or take them off?”

I groaned as Karen reached down and rubbed her palm up and down my shaft,

“They don’t seem to be covering much. I vote off.”

“They do look cute on him,” Jill said, running her finger over the head, scooping off a large dollop of precum. “I think they’ll just get in the way.”

My cock throbbed as she placed her finger to her mouth and licked it clean.

“You heard the ladies,” Rachel told me. “Off with them.”

Karen snatched them from me the moment I took them off. She then surprised by putting them on. She’d been panty less underneath her skirt all evening.

My bobbing hard-on lead the way as the three of us stepped to our front door. Once inside, the three of us gravitated to the living room.

“Rick, would please open a bottle of wine?” Rachel asked me.

I nodded and headed for the kitchen, keenly aware of the three sets of eyes staring at my ass as I left.

I couldn’t quite make out their conversation as I opened the wine bottle. When I re-entered the living room and saw Jill, sitting on our love seat clad only in a pair of purple boy-shorts, I almost dropped both the bottle and the glasses I was holding.

Her body was magnificent. Medium sized breasts capped off with hard pink nipples. My eyes scanned down her body to her flat tummy and slightly wide hips. I shot my wife a questioning look.

“Paper, Rock, Scissors,” Rachel gave me as explanation. “Jill won, she’s first.”

“But we get to direct,” Karen chimed in. “Jill, both feet on the floor and your arms out across the top of the couch.”

Jill did what Karen told her to do. As I slid her panties down her legs, I could see from her ‘landing strip’ she was blonde all over.

“Rick, put them on,” Rachel ordered. “Then I want you to kiss her.”

After sliding Jill’s panties on, I knelt in front of her. My panty covered cock throbbed as it brushed against her leg. I leaned over and kissed her. Jill’s lips were incredibly soft. First a small peck, then I let my tongue gently part her lips. I reached up and cupped her face as our tongues dueled together in her mouth.

“Touch her tits.”

I slowly slid my hands down her neck to her firm tits. She moaned as I gently squeezed them, rolling her nipples between my thumb and forefinger. I leaned down and took her right nipple in my mouth. Flicking my tongue over the tip.

“We didn’t tell you to do that,” Karen chastised.

“Mmmmm, don’t make him stop,” pouted Jill as she held my head to her breast.

“No I think we’ll have him keep going,” Rachel told her. “It’s time for him to lick your pussy.”

“Yes,” Jill moaned, pushing my head down her body.

Her pussy was dripping wet. She jumped as the tip of my tongue glanced across her hard clit. I slowly licked around her pussy lips, and then parted them with my tongue from bottom to top. I teased her little pussy by coming, oh so close, to her clit but always just missing it. Finally she’d had enough, grabbed my head and moved my mouth where she wanted it most.

I let out a small moan into her pussy as I felt a hand free my cock from their silky confines. My moan got louder as I felt a pair of lips engulf the head then shaft of my cock. I forced myself away from Jill’s dripping slit and confirmed that the lips belonged to Karen and the hand, my wife. My body shook as Karen swallowed my hard rod.

Rachel, clad only in her panties, moved in beside me turned my head towards her. She leaned in and after first licking Jill’s pussy juices from my mouth and chin, our lips met in one of the hottest kisses I had ever had.

“Damn Jill, you taste pretty good,” Rachel told her after breaking off our kiss.

“Jill, I need some more room down here, turn around on your knees,” Karen said, and then slid her lips back down my cock.

Jill turned around with her chest resting on the back of the couch. I gave her a quick lick, from her clit to her tail bone.

“Oh my God,” she gasped. “He just licked my asshole.”

She seemed to like it, so I did it again, stopping at her puckered hole and swirled my tongue around it for a few seconds. She let out a disappointed moan as I pulled away.

“Please don’t stop,” she cried out. “That feels so good.”

I put my tongue back on her crack. First I licked down from her butt to her clit, licking her there for a few minutes before going back up. Drilling her hole with my tongue.

“Mmmmm,” she moaned. “He’s fucking my ass with his tongue.”

I slid two fingers inside of her pussy, found her ‘G-spot’ and started rubbing it in time with my tongue driving in and out of her ass. The tremors running through her body started to intensify. Her pussy began squeezing my fingers; I knew she was going to cum. She let out a throaty scream as she climaxed.

“God that was intense,” she said as she caught her breath. “No one has ever licked my ass before…Fuck that felt good.”

She had turned around so that she was facing me. She leaned over and started kissing me. Our mouths parted and she watched my cock slowly slide in and out of Karen’s mouth for a few seconds.

“My turn to direct,” she exclaimed. “Rick, get on all fours.”

I quickly complied.

“Karen I want you to keep sucking his cock.”

Karen lay down beside me and worked her head in underneath. I was forced to spread my legs wide, to get my cock down to her mouth.

“Rachel, I want him to lick your pussy.”

Rachel quickly discarded her panties and sat down in front of me with her legs spread. I eased myself down on my elbows and started lapping at her pussy, from her asshole to her clit.

With my face buried in my wife’s pussy and Karen picking up her pace sucking my cock, I knew I wasn’t going to last much longer. Jill surprised me when she pulled the panties I was wearing down in back, spread my ass cheeks and started rimming my asshole.

“Oh yeah,” Rachel purred. “That feels so good.”

“Jill’s licking his ass,” Karen told her, taking my cock out of her mouth for a moment.

“Ohh,” she moaned. “That’s hot….I…cumming…!”

Her hips started bucking against my face as the words left her lips. She grabbed two big handfuls of my hair and ground her pussy against my mouth. Her juices poured out of her pussy I struggled to lick up every drop.

As Rachel caught her breath, Karen worked her way out from under me.

“I need this cock,” she exclaimed.

She quickly lay down in front of me with her legs spread wide, reached down and pulled my throbbing cock inside of her. Her pussy was dripping wet, my cock slid almost effortlessly in. As I leaned down and kissed her, Jill’s tongue found its way back down to my asshole. As I ground my pubic bone against Karen’s, Jill’s replaced her tongue with a finger.

“Slide it in,” Rachel urged. “He loves having his ass fingered.”

Her finger was resting and teasing the entrance to my hole. She plunged it deep as I eased back inside of Karen’s pussy. She continued finger fuck my ass as I slid my rock hard cock in and out of Karen’s steaming pussy.

“Here let me help,” Rachel said as one of her fingers joined Jill’s at the entrance to my ass. Simultaneously they both started finger fucking my ass.

Knowing I wasn’t going to last much longer, I hooked my arms under Karen’s legs, bringing them to my shoulders. I wrapped my mouth around her toes as I drove my cock deeper into her dripping pussy. She in turn, reached down and started rubbing both her clit and my shaft as it slid in and out. With a high pitched shriek and throaty moan, Karen started to climax.

That was all I could take.

“I’m gonna cum!” I announced.

“Shoot it on her tits,” Rachel ordered.

Karen sat up slightly as I pulled my cock from her pussy and started furiously jacking it. It was only a few seconds before I started shooting one string after another, all over her big boobs.

“Damn babe, you made quite a mess,” Rachel exclaimed, then turned to Karen. “I’ll get you a towel to wipe up with.”

“Don’t bother with a towel,” Karen said, cupping her tits. “I have a better idea.”

Unbelievably, my spent cock started to stiffen as Rachel and Jill knelt down on opposite sides of Karen, leaned down and started lapping at the cum splattered on her boobs…

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