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Holly and Nicks Group Initiation

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On Thursday afternoon, Jennifer sent me an e-mail telling me simply that the boots were thigh high leather and Holly and Jennifer had quite an evening together. Holly sent an e-mail at the end of the day telling me that she and Nick looked forward to Saturday night. I smiled, as I looked forward to Saturday myself.

Saturday afternoon, Jennifer dropped the kids off at her parent's house at noon and the three of went off to the grocery store for food, snack items, beer and liquor for the night. After shopping, we were busy arranging the down stairs family room for this evening's pleasure. We were finished around six and guests would begin arriving around seven. I went home to shower, shave, and change for the evening and left Jerry and Jennifer to get ready.

Having showered, I dressed casually in a yellow Polo shirt, black slacks, socks, and black loafers. In addition, I wore a pair of black silk briefs. I knew I wouldn't get to join in right away, but eventually, I would get to share in the fruits of the evening. I walked over to Jerry and Jennifer's just before the first of the regulars arrived.

Tonight, Jerry was dressed similar to me with a blue Polo shirt instead of yellow having decided not to role play as Jessica this evening. Jennifer wore a royal blue satin nightgown that revealed her cleavage down to just above her belly button. She also wore a similar color garter belt and nude hose. You could see the tops of her hose and the garters as she moved due to the slits in the sides of the gown up both legs nearly to her hips. Her red hair was down and her ass was perfectly displayed since she wore her black stiletto heels with straps and locks. She looked exquisite and extremely hot. As she opened the door for the first guests, the cool all air hit her nipples, which hardened so erotically under the satin gown.

The first guests to the door were Tom and Gloria. We welcomed them in and pleasantries were exchanged. Gloria wore a tan trench coat, cinched at the waist, a pair of black stiletto heels, and hose. When Jerry helped her out of her coat, she was wearing a black corset that barely contained her breasts and covered her nipples in the shelf top, and a black leather mini skirt. Tom wore khaki Dockers and a pale blue Polo shirt. Jennifer leaned in to kiss both on the cheek. As Tom bent down, Jennifer stroked his cock and noted, "You are going to have a very good time this evening."

Pleasantries aside, they moved down stairs. It wasn't but a few minutes later and another couple showed up at the door and then the steady stream of our regulars. Cars were parked in their driveway, mine, and along the street. Tom was helping with the bar and we all had at least an hour before our guests would arrive. We hadn't had an initiation in a while and Jennifer chose the light BDSM theme for the evening. We had set up the hand restraints attached to the doorsill in the hallway that led back to two down stairs guest bedrooms and the full bath with a shower for at least six. The doorway was extra wide with two doors that opened back into the hallway allowing room for someone to be cuffed in the doorway and for those to walk around them.

The spreader bar for the legs was also attached to the bottom of the doorway. There was ample room to lengthen the hand and arm restraints and bend the subject forward and over a rail and bench for better access. Only those of us who were part of the group knew what we would do to initiate the new couple to the group. Jennifer had a drink in one hand and was explaining to Gloria what she did to Holly Wednesday night, pointing to the Ramp and Wedge in the middle of the room causing quite a few smiles in the group.

Nine o'clock rapidly approached and everyone was excited. The three of us went upstairs to wait on our special guests. Just before nine, the doorbell rang. You could hear the music downstairs but everyone became quiet knowing what was to come next.

Jennifer opened the door for Holly and Nick. As they walked in, Nick had the biggest grin on his face and Holly was smiling almost a big. Jennifer greeted them warmly and kissed both Holly and Nick on the mouth, a little French kiss thrown in. "Ok you two, we will explain the rules for this evening. First, we will bring one of you down at a time. You both will go through the initiation alone. But, whoever goes first does get to watch the other get theirs."

Holly and Nick looked at each other as they took off their coats. Nick wore a nice button-down pale pink shirt with a pair of gray slacks. Holly wore a black version of Jennifer's satin gown and looked nearly as stunning. I put their coats in the closet and smiled. This was going to be quite an evening.

Jennifer pointed to two sets of Bose noise canceling headphones on the living room sofa; both connected to its own portable CD player. Next to the headphones were two black satin eye covers and two sets of hand and ankle restraints. Jennifer asked, "Ok, which one wants to go first?"

Holly stepped forward and said that she would be first. We sat Nick down on the sofa, helped him with the headphones, and fastened the blinders to cover his eyes so that he couldn't remove them. Jerry and I got him comfortable on their soft tufted leather sofa and placed the hand and ankle restraints on him. We then attached the restraints to the lashings that were secured at each leg of the sofa and over the back of the sofa's back. He had just enough room to recline and wait to be brought down. The music on the DVD player was set to repeat over again since we didn't know how long we would be with the first guest.

Holly watched as we completed each step of securing her husband to the sofa. Now, it was her turn. Jennifer helped to put the blinders on Holly as Jerry and I attached the restraints to her ankles and wrists. Jennifer then placed the headphones on her and we were ready to walk Holly down the stairs. The soft music in the noise canceling headphones was a mix of Enya, Kitaro, and Yanni, all three great mood music for heightening the mood for erotic sex.

We guided Holly down the stairs, Jennifer holding the portable CD player while Jerry and I each held on to an arm. Once downstairs, the oohs and aahs from everyone anticipating this evening's main entertainment approved of what they saw. Holly was a gorgeous woman. We moved her into position and Jennifer hung the CD player on the hook on the door jam. As we presented Holly to the group, Jennifer stepped in front of her and gave her a long deep kiss before slowly slipping one shoulder strap off and then the other to reveal Holly's massive and firm breasts. That allowed Jerry and I to hook up Holly's wrist restraints to their tethers.

Jennifer teasingly slid the gown down to Holly's hips taking the time to suck on each nipple and then down her tummy. When Jen slipped the gown over Holly's hips to expose the black garter and no panties showing off her shaved pussy with the small tuft of hair neatly trimmed at the top. There were a lot of smiles in the room. Jen let the gown drop to the floor and leaned in to lick at Holly's pussy getting a moan from Holly. Jerry and I got down on our knees to move the gown from under Holly's heels and to hook up the spreader bar. Once we connected the bar to Holly's ankle restraints, we were able to secured her ankles to the lower tethers. Holly was now ready for everyone to enjoy. Standing there, her arms over her head and spread wide, legs spread exposing her ass and pussy, wearing only a garter belt, hose, and heels, her nipples pointed out hard and needing attention. She was a gorgeous sight to see.

I stood back to watch as Jerry and Jennifer invited others up to start in on Holly's initiation fuck session. Jennifer went back to paying attention to Holly's left breast and nipple while Jerry took over the right side. Tom and Gloria moved in front of Holly and both slowly began to run their tongues from Holly's inner thighs up to her gaping pussy alternating between who got to run their tongue over her clit. Others watched from around the room as they began to undress. Everyone would have a turn at Holly and everyone would have a turn at Nick tonight. Then, everybody could have anybody who wanted to fuck, suck and fuck some more.

I watched one of the regulars, a long legged brunette named Rachel and her husband Chris moved in behind Holly and began to play with her ass. Now, she had six sets of hands and tongues massaging her body and both accessible lower orifices. Tom's cock was standing at attention, its full 12 inches and massive girth swayed around and I knew at some point, Holly as well as Nick, was going to get fucked silly by that massive cock.

It was Chris and Rachel who made the first move. With help from some lube, Rachel had inserted one finger and then two into Holly's ass and began to slowly fuck her. Holly moaned as Rachel's fingers began to loosen her ass up. Chris stood back and unwrapped a condom and slowly rolled it down onto his throbbing cock. He added some lube and lined up to replace Rachel's fingers. Chris pulled Holly's hips back just a little to give Chris an angel to fuck Holly's ass. Chris was a little larger than average but had excellent stamina. He slowly eased the head of his cock into her ass and began a slow ass fucking while Gloria now had the main control of Holly's clit and pussy. Jerry and Tom now suckled on Holly's nipples and tongued her breasts.

Gloria drove three fingers into Holly's pussy as she sucked on her clit. Holly was withering in ecstasy and moaning as her body began to shudder through her first of many orgasms to come. There was no sense of time. Chris continued to fuck Holly's ass and partners began to swap out, tag teaming her breasts and her pussy. Chris began to deliberately slam into Holly in his prelude to his own climax slipping his cock out and pulling the condom off to shooting his load on her ass. It was quite a sight.

Tom was next. Gloria affectionately rolled a condom onto Tom's massive cock playing with him as she did so. He wasn't after Holly's ass but was going to fuck her pussy with his massive meat. Pushing her over, fingers separated Holly's pussy lips and helped to guide Tom's massive member into Holly's waiting pussy. I always marvel at how something so big can be accommodated into something so tight, sooner or later. Something I would remember later.

Holly began shaking again as Tom eased into her. Everyone was up and gathered around to watch their performance. Holly's moans turned into, "Fuck, fuck, fuck, that is... Oh my, shit!" Then she bellowed, " Fuck me with that massive tool, who ever you are!"

Tom eased in as much as he could on his first attempt, not quite half way and began to ease back out. Holly continued to shudder. Tom then slid in a little deeper with each penetration until he hit home and nearly had his whole cock buried in Holly. At that point, Tom began to slowly fuck her and Tom definitely has stamina.

Gloria dropped to her knees in front of Holly to suck on her clit and try to lap up some of Holly's love juices that were slowly trickling down her legs when someone pushed the fuck bench into position in front of Holly. Gloria got up from Holly's pussy as the bench was lined up. There are two adjustable poles, one on each side, with a carabiner attached to rings at the top of the poles. This allowed Jerry and I to unhook Holly from the door jam tether hooks and hook her wrists to the poles.

There was an adjustable bar that allowed us to move Holly forward to bend her over the bar. We moved the CD player to hang on the one pole. There were gynecological stirrups for someone to lay back on the bench, head on a pillow and place their legs spread wide open in the stirrups and nudge forward for their pussy, ass, or cock to be made accessible. In this case, one of our female members, Michelle, took the opportunity to climb onto the bench and settle in. Once in position, Jerry and I guided Holly forward enough for her mouth to come into contact with Michelle's spread pussy lips and waiting cunt. Holly didn't have to be prodded further. She dove in as Tom continued to plow into her.

Gloria didn't miss a beat and moved to climb up on the end of the bench for Michelle to have access to her pussy as she watched Holly receiving and giving. This is always some of the hottest sex action when the guests of honor are totally immersed in sex.

Tom continued to fuck Holly, Gloria swapped out with Linda so that Michelle would have yet another pussy to eat. The guys were all standing around waiting for their turn to fuck Holly's ass or pussy. When Tom finally began to slam hard into Holly, you knew he was about to cum and cum big. Holly kept trying to meet his thrusts and moaned into Michelle's pussy when Tom slid his massive cock out of Holly, her pussy left gapping, and pulled off the condom pumping his massive cock looking for a place to deposit his load. Jennifer dropped to her knees and opened her mouth to let him shoot his load in her mouth and over her face.

Nearly thirty minutes had elapsed and I needed to walk upstairs and check on Nick as members changed positions and another began to fuck Holly. I touched him on the shoulder to let him know I was there and pulled the headphones to one side for a moment just to let him know it would be a little while yet. He just shook his head. I let my right hand slide down his chest and to his crotch to check on his cock status. He was semi erect when I first touched him but began to harden as I massaged his love tool. Once hard, I retracted my hand to leave him wanting more and went back down stairs to check on Holly's fuck session.

Returning to the action, another session was in action and Holly continued to get drilled. It was more like forty minutes, not thirty, before everyone had a round with Holly, one way or another. Even Nancy fucked Holly with a strap-on. Finally, with Holly still shuddering from her last climax and nearly satiated, Jerry and I unhooked Holly and led her to the sofa. Jennifer brought her a glass of ice water and a glass of wine. Holly looked around the room at all of the members who had their way with her and smiled, "I have never been fucked like this, ever! Wow!" Holly received a round of applause from the group.

Jennifer smiled at Holly and commented, "Now, its Nick's turn and you get to watch."

"I sure hope someone got my session on tape because I want to see that after having felt it all."

Jerry pointed to the two video cameras set up in the room and smiled, "You were awesome. And, you'll have Nick's initiation into the group recorded as well, once Tom works his magic with the recordings."

Tom sauntered up to Holly, his massive cock hanging down between his legs. "I'll have it done for you by next weekend."

Holly's eyes grew wide as she pointed to Tom's cock, "I took that?"

Jennifer smiled and replied, "Yes dear, you did. And it gets much bigger than that. Don't worry; just think of Nick having Tom fucking him soon. He's going to pass out."

After five minutes, Jerry and I went upstairs to get Nick and bring him down for his turn with the group. He had waited over an hour as his wife was fucked again and again. He was about to have an experience some only dream of having with a group of likeminded people.

At the bottom of the stairs, Jerry and I waited for Gloria and Jennifer to unbutton Nick's shirt and pull it off one arm at a time before we attached his wrists to the restraint tethers. Then we let the girls unbuckle his belt, unbutton his slacks, and slowly slide down his zipper before letting his pants drop to his ankles leaving him standing there in a blue thong with a raging hard on. Michelle stepped forward to slowly pull it down to his ankles letting his erection spring out of its casing. She slid the thong off and pulled off his shoes, socks, and slacks before helping to connect the spreader bar to his ankles and then to the lower restraint tethers. Holly smiled as it was now her husbands turn to get thoroughly fucked and used until he could no longer stand.

David first went to work on Nick's ass by standing behind him and gently massaging Astroglide on his ass working a finger, then two, into his ass. Michelle dropped to her knees and began to lick Nick's cock like a lollypop. Nancy walked up to David, her strap-on cock bouncing around as if it were an epee, and rolled a condom onto his throbbing eight-inch member after which she then help to guide him into Nick's well lubed ass. By this time, couples lined up around Nick to have their turn at him.

David thoroughly fucked Nick standing up, his cock sliding in and out of his tight ass. Michelle watched with extreme interest until David was nearly ready to cum. David pulled out and left Nick's ass gaping open. Tom wasn't about to lose the opportunity and slid in position to help bend Nick forward while his ass was still open and began to impale Nick on the twelve inches of pleasure meat. You could hear Nick say, "Oh shit, that is so fucking filling. You're stretching my ass out."

Nancy pulled the condom off of David's pleasure stick and pumped it for all she was worth letting David cum all over Nick's side and ass with three hot jets of cum. Holly got up close to watch her husband take all of Tom's cock and was mesmerized at how Tom was able to impale Nick on his cock. Jerry pushed the bench up and we hooked Nick up, bending him over for Tom to have a better angle at fucking his ass while another one of our male members climbed up onto the bench. Holly then guided Nick's head to the stiff cock and placed his lips on the head. Nick got the hint and began bobbing his head up and down on the thick cock before him.

Both Jerry and I had been guides up until this point and we began to peel our clothes off take part in the fun. Holly grabbed me and pulled me close and spread her legs and looked over her shoulder, "Take me. No fucking rubber, just fuck my pussy and let me feel you cum in me!" I didn't have to be told twice.

She arched her ass back to me grabbing hold of one of the bench poles giving me open access to her hot pussy. I slid right into her hot pussy. I grabbed her hips and began to slowly fuck her as she watched Tom fuck Nick.

Gloria pulled Nancy over to the sofa and guided Nancy's strap-on into her waiting pussy and Jennifer climbed aboard Gloria's tongue, straddling her facing forward. This allowed Jennifer to be a fluffer for cock getting ready to fuck Nick once Tom was done. Nicks cock was oozing precum, almost like a faucet with a bad seal as Tom continued tapping that ass with every inch of his cock.

When Tom was finally ready to cum, he pulled out of Nick's ass leaving it agape, and another cock quickly replaced Tom's. Tom pealed the condom from his cock and shot a huge load onto Nick's back giving everyone a show of the load he would have deposited deep in Nick's ass if he had been bareback.

Holly nearly passed out watching Tom's cock erupt with his massive load. Her pussy clamped down on my cock as she reached yet another orgasm. I felt her knees begin to buckle as she quivered and convulsed. Her pussy continued to milk my cock for all it was worth.

Nick continued to suck Jerry's cock and finally was able to make him cum. Nick attempted to suck all of the cum from Jerry's member allowing only a small amount to escape from his lips and down his chin. Regardless, it is always an erotic sight to see.

I felt my first climax of the evening coming along as Holly continued to milk my cock with each stroke. There was another shift change to tap Nick's ass as another cock slid deep into his ass while a women replaced Jerry on the bench spreading her pussy lips for Nick to dive into her folds. I grabbed ahold of Holly's swaying breasts and began to slam into her hard as I began to erupt, depositing several spurts of cum deep into her cunt. She felt awesome. Her pussy milked my cock of every drop. As I pulled out, Jennifer moved in to suck the cum I had just deposited in Holly's pussy.

I took a break and walked over to the bar to get a drink and watch Nick continue to get fucked. After about ten minutes of watching the action, one of our regulars, a doctor named Brian, walked over and commented on the great additions to the group. We chatted about the others in the room as we watched several couples including Brian's wife, Susan who was laid out on her back on the floor on a blanket with Gina spread over face offering her a juicy pussy. Between Susan's spread legs, was Gina's husband, Rick, going to town tongue deep into Susan's pussy. I noticed Brian's cock regaining its hardness as he began to slowly stroke it while we watched the group.

I dropped to my knees and placed my cup on the floor. I allowed my tongue to slowly trace along the head of his member. It flinched with each flick of my chilled tongue as his hand gave way to my mouth. I sipped my drink again and took a small ice cube in order to add a little more of a chill to his cock. He moaned out loud and his cock throbbed even more while continuing to stiffen. I put my glass down and placed my hands on Brian's ass cheeks pulling him closer allowing his cock to fill my mouth.

My own cock began to stir as I worked on Brian's tool. I had a great angle to see his wife and the others as I enjoyed his engorged cock. Brian continued watching them as well. As Brian fucked my mouth, Susan made Gina cum hard. Rick then moved over to the group working on Nick and left Susan's pussy wide open. Brian noticed and commented, "Let's move over to Susan."

I reluctantly let go of his cock, letting it slide out of my mouth teasing the head. We moved over to Susan who noticed us pleaded, "One of you suck my pussy! I was close to cumming before he left me hanging."

I dropped to my knees in front of her bare pussy. Her pussy lips were pulsing and gaping wide open beckoning me to finish what Rick started. Her lips were slick and when my tongue tickled them, I could feel her body shiver.

In no time, I dipped my tongue deep into her pussy and tongue fucked her while moving up and down to take the opportunity to suck on her clit before diving back in again. I slid my right hand under her ass to get an angle to let a finger dip into her tight asshole. She moaned as I slid in one finger and her hips pressed harder onto my tongue. I had lost track of Brian until I felt the lube being applied to my ass and a finger slide into my tight ass making my own cock jump.

He slipped his finger out after giving me a good prostate massage and I heard a condom wrapper being ripped open knowing that it was meant for Brian's cock and for me to receive a good ass fucking.

Susan peeked out from under Gina's pussy to see Brian lining up behind me. "Oh baby, that looks so hot. I'm going to cum."

She did as Brian's cock penetrated my ass. Damn, he was filling me up slowly and it felt so good. Susan came with a shudder and very loud moan giving me pleasure knowing I was instrumental in helping her climax. I continued to work on her as Brian worked my ass.

He had grabbed ahold of my hips and guided my ass on his cock. He fucked me slowly and deep. I could feel his cock throbbing with each stroke. I loved the sensations of feeling her pussy throbbing from my tongue and the feeling of being fucked. To top it off, I had a view of Nick bent over the bench, sucking a cock, having his ass drilled with Holly watching her man up close while she straddled Nancy's mouth and tongue. Oh my.

I lost track of time. The sensations were incredible. I knew my ass felt good to Brian. He kept saying it out load. "Milk my cock with that tight ass, that's it. Oh, fuck!"

Susan came again for me as I had opened her ass with three fingers plunging deep into her while sucking on her clit. It sent her over the edge. As she moaned, Brian pulled out of my ass and peeled off the condom, letting a huge load shoot out onto my ass and back. I felt someone behind me again as Brian slid away. I felt pressure on my ass knowing it was being stretched further than Brian's cock could open me up. It was Tom. I was about to be drilled in the ass by the largest cock of the group.

My ass gave way. I am glad I was still loose but his cock about had me seeing stars. "Relax, I'll let you get used to me," He said in an attempt to sooth me.

The sensation was so incredible and I was now feeling how massive his cock really was as he began to enter me. I had shared sucking him off with Gina before he mounted her in one of our previous sessions but I hadn't had him fuck my ass yet. He loved fucking Jerry's ass and Jerry always said it was quite an experience. I was about to have my own.

Tom pulled me away from Susan's pussy and rolled me on my back. His cock never left my ass and he was only half way in me. He slid a pillow under my hips and pulled my legs up spreading them wide and giving him an angle to penetrate me further. I almost passed out as he bottomed out in me. I could feel his balls against my ass. "Damn, Brian was right. Your ass does milk cock. You are so tight and fucking amazing feeling you have milking me."

All I knew was I was so incredibly full of cock before he began to pull out of me. He reached over to grab the lube bottle and squirted some on his cock and around my ass lips before sliding back into me. He was slow and deliberate with each stroke allowing my ass to get used to his massive size. He kept on fucking me as my own cock oozed precum. Did I say it was incredible?

I grabbed my legs as he pushed them wide open and back giving him unabated access to me. I looked him in the eyes and said, "Fuck me! I want your cock without that damn rubber and I want to feel you cum in me. Pump your cum in me!"

It didn't take Tom but a few moments to pull out leaving my ass gaping wide open, needing him to fill me again, before he slipped off the condom and applied more lube and jamming his cock back into me. I wanted him to fuck the daylights out of me. He didn't disappoint.

I tried to milk his cock each time he would bottom out in me and milk him as he slid out to the head before easing back into me to the hilt. He moaned each time and told me how good my ass felt. I wanted to give him as much pleasure as he was giving me.

The incredible sensations running through me were indescribable. I felt the cum continue to flow from my own cock as Tom fucked me. I swear I nearly passed out from the feeling. When Tom was finally ready to unload in my ass, he told me he was going to fill my ass.

He did as he said. As I milked him, I felt his cock begin to shoot load after load deep into me. What a feeling. He stayed buried in me until he emptied his load and then pulled out, leaving my ass gaping wide open and cum draining from my wide-open ass. I had never had my ass fucked like he fucked me. I loved anal before but never thought I could handle a massive cock like Tom's.

It was quite an evening that lasted well into the early morning hours. Some of the guests remained over night. I woke up in Jerry and Jennifer's bed with Holly sucking on my cock. Needless to say, we started Sunday off with a good slow fuck. Holly and Nick's initiation into the group was a total success.

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