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Nick Meets Jessica

Jennifer had taken a long bath, away from the kids, and looked exquisitely sexy with her hair back in a ponytail. She wore one of Jerry's blue button-down dress shirts with the top three buttons unbuttoned and the tails out along with a pair of nice white shorts that showcased her awesome legs. Her bare feet rested on the chair caddy corner to her at the table. I always thought she could make a potato sack look alluring. I wore khaki cargo shorts and a dark blue golf shirt.

"When I talked to Jerry this morning about our night last night, he begged for details. He wants a go at Nick too."

I smiled at her. "Well, does he want to play Wednesday night? Maybe we could have a ladies night and a guys night out."

"I think he wants to hook up with Nick as Jess and see how that works. It would be a good way to break him in before next weekend's get together. Besides, if you two have Nick, like you said, maybe I could have Holly at our house. That is a good idea."

I smiled at her and hoisted my beer for a toast, "To Wednesday night."

"Yes, to Wednesday night. But for now, I need you. My pussy is throbbing."

I took the cue and dropped to my knees right there in the kitchen. I slid my hands up her legs to her ass and then let my fingers wander to the waistband of her shorts where I let my fingers slowly unbutton and unzip her shorts. She helped me by lifting her ass as I slid them down her legs giving me that awesome view of her shaved pussy, begging to be licked and sucked.

I began to tease her as I let my tongue drift up her inner left thigh almost making contact with her outer pussy lips but bypassed them to let my tongue glide down the inside of her right thigh down to her inside of her knee before slowly working my way back up. I paused at her pussy letting her feel my breath on her gaping love box. I knew her clit was throbbing.

She shifted in the chair giving me open access to her sweet pussy. I slowly let my tongue trace up the outer lips, nibbling as I did so. I was not going to touch that clit until she begged for it. When I began to suck on her outer lips ever so lightly, she moaned. As I let my hands pull her forward to my tongue, I could feel her pussy lips quiver with each lick and nibble.

Finally, she couldn't take it any longer and she grabbed the back of my head and pulled me in tight to her pussy. I let my tongue finally massage her clit. She shuddered after just a few moments of stimulation. I could feel her body quiver as she quickly reached her first climax.

Jen threw her head back and placed her legs over my shoulders. I had the perfect angle to tongue fuck her pussy and slip down to tease her little rosebud. I slid my right thumb into her pussy as I sucked her clit and then slipped my middle finger into her hot ass. It didn't take long before I got my first shot of pussy juices as she came again.

I could devour her pussy. Her sweet nectar was intoxicating. She could drive me wild. Finally, she begged me to stop and asked me if we could carry this session upstairs to my master bedroom. Of course I complied. We fucked our brains out that day, night and twice again on Sunday before she had to finally get herself together. The kids were due back from her mom's house and she still needed time to pick up Jerry at the airport. From our conversation on the phone Monday afternoon, Jerry drilled her twice more when he got home.

Monday evening after work, Jerry and I sat on his back deck, beers in hand, and talking about our Friday night adventures with Nick and Holly. Jen had filled him in Saturday on the phone and they talked about it again when he got home Sunday evening following their first fuck session. "When Jen told me, in detail, about you taking Nick's cherry after we had already fucked, I swear I was hard again damn near instantly."

"So what do you think of Jen's proposal for Wednesday evening? She said you would love to enjoy Nick too unless you just want to wait until Saturday night and see how they do with the group," I noted.

Jerry thought about it for a few minutes. "I do think that I can get home at a decent time Wednesday to get dressed. Where do we meet him?"

"How about we just have him come here? You can already be upstairs in the bedroom. Should be a great surprise. He knows, but he doesn't."

Jen walked out onto the deck with a phone in her hand. The kids were busy doing homework and no sports or gymnastics this Monday and it was just us three on the deck. "I have Holly on the phone and she's asked what we were up to on Wednesday. Are we good?"

Jerry smiled at his wife and nodded his head yes. "As long as we both can get home and you can help me transform, we should be good."

"Holly, yes we are on for Wednesday evening. You and I will be here and Nick will go next door. I look forward to enjoying you Wednesday evening too. See you then."

Holly sat down next to Jerry and smiled. "We're on. Just need to have Jerry ready to go before the kids get back from gymnastics. Shannon drives on Wednesday so we have time."

I smiled at them both and presented a toast, "Wednesday it is."

Tuesday came and went. Wednesday morning, I had left a meeting and sat down at my desk to find e-mail from Holly telling me they were looking forward to this evening and were definitely going to be there Saturday night.

Jerry had gotten off earlier than he had thought and had plenty of time to get ready. By the time Jennifer got home, they only had to deal with makeup. Jerry had decided to wear a black corset with garters, black thong with a quick release hook on the side, black hose with seams, red stilettos, the proverbial little black dress and a strand of pearls. Jen chose the shoulder length black wig that had bangs and sexily framed Jerry's face into Jess. Jen gave him a "come fuck me" make up job with red lipstick and super sultry eyes. He was always hot looking as Jess.

It got dark early in the fall and Jess left the house by the lower level patio doors, crossed between our yards and entered in my downstairs patio doors. He had his bag of clothes to change into before heading home if needed and his make up kit to freshen up. We walked upstairs to the bedroom so that he could put his bag in my closet and help me light the candles in the room. I had changed the sheets, making the bed with blue satin sheets that shimmered in the candle glow. I told Jess how sexy he looked and knew that Nick would be in for one hell of a fuck session tonight.

Jess cracked open a bottle of German white wine, a fine Riesling Auslese from the Mosel area. Three glasses were set aside and Jess filled one for each of us. The phone rang and Jen said that the kids just came home and were getting ready for bed and Holly and Nick would be on their way shortly.

Sipping our wine, I couldn't help but want to fuck the hell out of Jess, looking so sultry there in my master bedroom suite. But, I knew I would have to go next door to chat with Holly and Nick when they arrived and to walk Nick back over to the house. I knew that Holly and Jen wouldn't get started right away with the kids just getting ready for bed but wanted to make sure we played out the erotic role for Nick to enjoy Jess this evening. I was looking forward to being the director and getting some this evening as well.

The idea was to have Jess on the bed, leaning back against the headboard, dressed and waiting on Nick to arrive. I was going to be the one to give him directions for the evening. I was hard just thinking about it.

I dressed simple, black slacks, grey button-down shirt, and a pair of blue silk briefs that exquisitely encased my cock. I slipped on a pair of black loafers and stood in front of Jess, "Its show time."

I made my way over to Jen and Jerry's back patio doors and walked in. The family room was dimly lit with candles making it easy to navigate to the stairs. I noticed a Wedge and Ramp pillow set, complete with restraints, set up on the carpet next to the sofa. I smiled. I flipped on the light switch for the stairs and made my way up to the kitchen. Jess was walking down the stairs after having made sure that the kids were finishing up with bath time and brushing their teeth. She was dressed in a dark blue silk floor length robe that I knew hid her white garter belt, white hose, and also knew that those perfect breasts were free waiting for Holly's attention. The doorbell rang.

Jen smiled and made her way to the front door. Opening it, Holly and Nick were smiling and both held a bottle of wine in one hand and looked as delicious as always. Nick was dressed in a pair of slate Dockers, white Polo shirt and black sports jacket. Holly had on a long length black trench coat pulled tight and covered everything but her black leather boots with six-inch heels. I was wondering how high her boots went. I made a mental note to ask Jen later.

Jen invited them in. Jen asked if Holly wanted to hang up her coat and Holly shook her head no. "Not until the kids are asleep," she said with a glimmer in her eyes and a smile.

"Well then, let's move this down stairs to the family room and bar. The kids should be fine now if not already asleep. School day tomorrow."

Jen first showed them around the main floor of the house before heading down stairs. Once down stairs, Jen turned on the main lights and used the dimmer switch to lower the lighting level to compliment the candles. Jen moved to the bar and pulled out four wine glasses while Nick opened one of the bottles. Holly looked around the room and spotted the Wedge and Ramp set up and walked over to it.

"Jen, what is this thing? It looks interesting."

Jen smiled and replied, "Yes it is interesting and it's called a Wedge and Ramp. It is great for access and leverage. Got it from an on-line store in Atlanta. I'll show you how we use it here in a few minutes."

Nick smiled, "Baby, you are going to enjoy yourself tonight."

"Baby, so will you."

I only let Nick fill my glass half full before cutting him off. I knew that Jen wanted to get comfortable with Holly here soon enough and I also knew that Jerry was waiting at my house. He took my cue and only filled his half full but filled both girls' wine glasses.

Nick raised his glass for a toast. We touched glasses and Nick said, "To a hot evening with special friends."

"Definitely to a hot time tonight," Holly responded.

I finished my half glass and nudged Nick's arm to let him know we were ready to move over to my house. Nick finished off his glass and set it down on the bar and said, "Ladies, enjoy. We will see you sometime later."

I patted him on the ass and moved to open the sliding doors and had him follow me out. I closed the doors as Jen moved to turn the dimmer switch all the way down and closed the curtains. I really wanted to watch them again but quickly shook it off.

Nick followed me over to my back door. I had left the outside light off but we had the walkway lamps to provide light up to the door. I let Nick walk in and I followed, turning on the family room light switch. As I closed the doors, I motioned for Nick to follow me up the stairs. On the main level, I took his jacket and hung it on the coat rack at the front door.

"I have wine for us upstairs and a surprise for you this evening. Remember, you are going to do what I tell you. You will have quite an experience tonight."

"I'm looking forward to this. I was going crazy with anticipation not knowing what to expect."

"Well, I hope you enjoyed yourself Friday night," I said.

"That is an understatement. That was the most erotic experience I've ever had."

I smiled at him, "Between tonight and what you will experience this coming Saturday night, you will have your world rocked."

I moved forward to him and put my right hand on his crotch to feel if he was hard before heading upstairs. I wasn't disappointed. His cock was straining whatever he wore underneath his slacks. "I like that."

I slowly unzipped his pants, reached in to see if I could pull his rock hard cock free and found that I needed to unbuckle his belt, unbutton his pants before I could slip my had into his satin thong to release his throbbing cock. I dropped to my knees and slowly engulfed his cock while he stood at the breakfast bar.

A few moments of pleasuring his cock and I looked up at him and said, "Ok big boy, it is time to go upstairs. Button up. I don't want you to lose your pants going up the stairs."

I got up as he began to button and zip up his fly. Then I grabbed his hand and had him follow me around the corner and up the main stairway between the formal living room and the main floor family room. I stopped at the door to the master suite. Soft music played on the bedroom stereo system. Enya's Watermark album was currently playing. "Now, when you enter, I want you to move to the right of the suite and stop before the bed. Ok?"

He nodded his head in acceptance and followed me into the bedroom. Jess was in the middle of the bed, back against the headboard and pillows, legs out and erotically crossed, head cocked to the side, and empty wine glass in hand giving Nick a "I am going to fuck you" look. Jess was looking incredibly hot and sexy and softly spoke as he reached out to hand Nick the glass, "Would you be a dear and fill my glass for me?

Nick nodded his head and reached for the glass. Jess smiled as Nick took the glass. He turned to me and I winked at him. As he filled the glass, I moved to the settee next to the widow. This gave me a direct view of what was about to happen.

"Nick, once you fill that glass, please pour me one too," I motioned toward the other glass at the nightstand.

He poured my glass and brought it to me. "Now, be a dear and give Jessica and I a little strip show and take it down to that sexy thong you have on, please."

"Yes," was all he could mutter.

You could tell Nick was excited but also unsure. He was trying to figure out who Jessica was first. That was how good Jess looked dressed up.

"Nick, its me, Jerry. But for right now, I'm Jessica"

Nick sat back and looked astonished. "No shit? It is you?"

Jess nodded with approval as Nick began to rock slowly while unbuttoning his shirt. "Let me see you slowly move those hips for me, as if you are slowly and deliberately fucking me, while you strip those clothes off," Jess sexily noted.

Nick added a slow hip rotation that closely imitated a slow fucking motion while he continued so shed his shirt. He slipped off his shoes and reached down to remove his socks before resuming his hip movements while he unbuckled his belt and unbuttoned his pants.

"Jess honey, I took the liberty to check out his package to make sure he was actually ready for you this evening. I admit, he's got one hard cock waiting for attention."

"Oh he does, does he? Let me see those slacks fall and I'll be the judge of whether he's ready or not," Jess whispered.

As Nick's slacks fell to the floor, his cock strained the satin fabric of his thong. Jess batted her long black fake eyelashes and put her hand to her mouth acting as if astonished, displaying the long red fake fingernails on her hand and sighed, "Oh my. I do think he's a bit excited."

"Nick, move over to the end of the bed and let Jess see what you have there," I said.

Nick moved slowly to the edge of the bed. Jess shifted on the bed getting to her knees and leaned forward to run her fingers along the waistband of Nick's thong and looked up at him, "So, what do we have here?"

Nick's cock strained at the fabric. Jess slowly slid the band down releasing Nick's cock from its satin confines. "Take them all the way off," Jess whispered to Nick.

I sat there watching as Nick slid his thong down, leaving him standing there naked with his rock hard cock standing straight up. You could see it throbbing.

Once the thong was off, Jess reached forward and slowly grasped Nick's cock with one hand and pulled him close. Nick's body easily gave in to Jess's advances. Jess leaned further and let her tongue flick the head of Nick's cock. Then, slowly, Jess let her tongue circle the head and slowly slide down the underside of the shaft to his shaved balls before slowly running back up to the head. I sat there watching knowing how extremely erotic this was to watch and how good of a cocksucker Jerry was, especially when he was in his "Jessica" role. I had to shift in my seat and relieve the pressure my cock felt trapped inside my own pants.

Jess artfully began to perform one of her best blowjobs on Nick as he stood there. "Remember Nick. You don't cum until Jessica says so. Do you hear me?"

Nick nodded his head as Jess continued to suck, lick, kiss, and nibble on Nick's member. Nick began to pump his cock into Jess's mouth and she back off reminding him he wasn't going to cum yet. Jess worked him slowly for a few more minutes and leaned back looking up at him, "Now, get up here on the bed."

Jess slid backward to the middle of the bed as Nick climbed up onto the king sized bed. Jess smiled and asked, "You do know the primary reason for satin sheets is to fuck, don't you?"

Nick looked puzzled but responded, "I guess that makes sense. You move around easily on them but they sure feel sexy against the skin."

"Oh yes baby, they do all that. Now, be a dear and unzip my dress please."

Jess turned giving Nick access to the zipper running down her back and he slowly slid the zipper downward all the way to her waist.

"Thank you. You are such a handsome hunk."

Jess moved to slide off the bed and stood to wiggle out of the little black dress, back turned to Nick but facing me. Slowly, she let the dress slide down and stepped out of it after it was at her feet. Standing there in the corset, thong, hose, and red stilettos, Jess was as incredibly sexy as any lingerie model. His cock was straining the thong in front with more than two inches of cock and the head exposed above the thong's material. Jess smiled at me and turned toward Nick and said, "Now, please unhook my thong. There's a clip on the side."

Nick's eyes got wide as saucers as he saw Jess's cock before him, encased in the black thong. Nick moved forward to the edge of the bed, his eyes never leaving Jess's cock, and reached for her hips to pull her closer. He found the clip and unhooked the band, letting the thong fall down Jess's legs.

Jess's cock was right in front of Nick's face, "Like what you see baby?"

"Oh yes," Nick muttered.

"You can lick it if you like," Jess responded.

Nick pulled Jess's hips forward and let his mouth engulf Jess's cock immediately. Nick must have remembered what he was taught Friday night as he delicately began to suck and lick Jess's throbbing cock instead of how he tried to "Hoover" me the first time.

"Oh baby, you've gotten some experience as a cock sucker, haven't you?"

Nick released Jess's cock slowly to respond, "I had a good teacher," referring to me.

"I can tell. I was told you were a little rough at first but learned how to suck cock fairly well."

Jess moved Nick back onto the bed and climbed up into the middle and propped herself up with pillows at the headboard to have a better view of watching Nick suck cock. "Ok, let's continue," Jess said.

Nick slid around and knelt between Jess's spread legs and resumed sucking on Jess's cock. They were putting on quite a show as I sat back and watched. Jess was giving Nick instruction on how to refine his cock-sucking skills and Nick would apply each technique as instructed, down to running his hands along Jess's nylon clad thighs and teasing Jess's puckered asshole with his tongue. He did remember some of the tricks from Friday night.

I got up from my seat and went to the nightstand and removed a bottle of Astroglide. I handed it to Nick and reminded him that lube was his best friend when it came to inserting something into another's ass, even if it was a finger or two. I squirted a dab onto Nick's fingers and he proceeded to slipping one into Jess's unbelievably hot ass. Jess loves to have his prostate massaged.

After nearly fifteen minutes of oral pleasuring, Jess slid to the side of the bed and moved Nick into a sixty-nine position. I took that cue as the opportunity to fuck Nick's ass while they sucked each other's cocks. I stripped, placing my clothes on the settee and grabbed the bottle of lube. I squirted some onto my cock and then more onto my fingers and moved up onto the bed behind Nick. I slid up and slowly massaged his asshole getting him to moan a little louder anticipating his ass was about to be penetrated again.

I was able to get in two fingers stretching his ass and moved forward to let my cock begin to enter his hot ass. He pushed back against me, this time allowing my cock to slip into him slowly. I always love the feeling of the head passing through the tight muscle and into the hot depths. I let him move slowly back onto my throbbing rod as I slid slowly forward to bury myself in him.

I began fucking him very slowly, easing myself out to the head of my cock and then slowly forward again to my balls. Slowly, we were all engaged in an erotic copulation. I could see me fucking Nick's ass and them sucking in the mirror on the dresser. It was quite an erotic sight.

Jess began telling Nick that he was about to cum if he didn't back off for a moment. But, Nick was getting his ass fucked and told Jess he wanted to taste his cum. He was ready for the load and wanted to feel his cock erupt. I began to fuck Nick's ass harder as I heard them talking. Jess came first, in a huge eruption of cum, shooting into Nick's mouth and moaning, "Oh fuck!"

As Nick greedily sucked all of the cum from Jess's cock, he began to force himself back onto my cock in an attempt to match thrusts as Jess worked to make him deliver his load. As Nick's body shook, Jess told him to feed him everything he had. Nick erupted moments later. I kept pounding away even as Jess let Nick's cock slid from his lips. Jess had a great view of my balls slapping Nick's ass as I fucked him hard.

I felt my orgasm coming on and announced it to both of them, "I going to cum deep in your ass!"

I did. And, I came a lot. I kept myself buried in his ass until my cock finally went soft and began to slide out with very little help. We all separated, giving each other a little space and allowed us to catch our breath. Nick rolled to his side and looked at Jess and I and said, "I can't believe I've missed these kind of erotic fuck sessions all my life."

I looked at Nick and smiled. "Since you now see what you've been missing, you will take it to another level on Saturday night. You and Holly will be the guests of honor as our new orgy virgins. You will have one heck of an experience.

"Oh yes Nick. You and Holly will really enjoy our group." Jerry noted. "By the way, you learned how to suck cock pretty well there."

Nick, still wowed by Jessica responded. "You look so, so, real. Damn. You look so fucking hot."

"Why thank you. I never would have guessed you and Holly would be looking to play with other couples. Your wanting to explore the bi experience was a shocker. Glad Jennifer told me about Friday night."

I filled up our glasses with the remaining wine in the bottle and we sat back and chatted and cracked open a second bottle of wine. Nick couldn't keep his eyes off Jerry as Jessica and kept rubbing his nylon-clad legs. "You are so fucking hot in that outfit. You have a killer body."

Jerry responded, "So do you and Holly."

"Hey guys," I said. I want to be drilled and filled tonight too you know. I gave them both a sly grin. I want to have cock in my ass and one in my mouth. I don't care who is where but please, fuck me," I pleaded.

Nick slid over and leaned back into the pillows against the headboard, spread his legs and started to massage his cock. I crawled between his legs and began to suck on his cock helping him bring it back to life. As he grew in my mouth slowly, Jerry slid behind me and spread my legs giving him access to my ass. I felt the cool dollop of lube added to my ass as I anticipated to be mounted by Jerry. I looked in the mirror at the three of us and smiled as Jerry's cock began to rise to the occasion and I worked Nick's love muscle.

Nick was watching Jerry as he lined up behind me and slowly began to ease his cock in my ass. Nick commented, "Damn, that is so hot, a chick with a cock and getting to see it live right before my eyes."

I loved the sensation of Jerry's cock in my ass as he began to slowly fuck me. I could feel his head as he would nearly pull out of me before sliding slowly back into me. I began to slowly try to match his rhythm. My cock began to spasm leaking precum each time he slid deep into me. Nick moved to slide out from underneath my grip and moved around to the nightstand and lubed his cock before moving in behind Jessica's ass. He slid a finger into Jerry's hot ass. I could feel Jerry's cock spasm. He didn't cum, but you could tell Nick was hitting the right spot.

Nick lined up behind him and finally slid into Jess's hot ass. I looked over at the mirror to see the erotic sight. We got into rhythm and the three of us had quite a fuck fest. Both of them had more stamina the second time around and controlled themselves quite well. My cock began to spasm first as Jerry began to slam into my ass hard. My body shook as Jerry kept slamming into my ass until he finally unloaded deep in me. I love it when he does that.

Jerry's cock remained buried in me, still hard, as Nick grabbed him by the waist, and bent him over me while continuing to pound away at Jerry's ass. Finally, Nick erupted in his ass sending an eruption of hot cum deep into his man pussy.

It took some time for Jerry's cock to lose its hardness and begins to slip out of my ass and the same for Nick and Jerry. We lay back on the bed, satisfied. Nick had quite a grin on his face. He still couldn't get enough of Jerry as Jessica. I knew we had him hooked.

"You know Nick," I said. "You and Holly will be in for quite an initiation to the group Saturday evening. We expect you two at Jerry and Jennifer's promptly at nine. Remember, we and I mean all of us, will enjoy both of you. Any reservations?"

"None at all. I still can't believe what I've been missing all these years. I wonder how Holly and Jennifer are doing?"

Jerry smiled as he grasped Nick's cock, "Don't worry about it. Go take a shower and come back to bed. I'm not done with you yet tonight."

Jerry went into the bathroom to clean up and rework his makeup. Nick followed him into the bathroom to take a shower. I smiled knowing we had expanded our inner circle and looked forward to Saturday night knowing what was in store for the two of them. That is another story.