Chapter 3: Hailey visits the club and breaks new ground with Jake

Hailey

It was Tuesday night and Jake was coming over to see me. We’d had a wonderful evening the night before and it was almost as if I could feel our relationship growing stronger. I was still very hesitant about his club, but more than anything I was intrigued. I’d always had a high sex drive and I’d always thought of myself as being very adventurous, but only with one man at a time while being in a monogamous relationship. However, after meeting Jake and him relating to me what went on at his club I realized that maybe I wasn’t quite as open-minded as I’d thought I was. I’d had no idea that people exchanged partners and had sex in front of each other like he’d described.

Also, he’d told me that some of his members were into BDSM play. I had to admit I’d always been curious about that, but I was never with a man who was into it. Now that I’d met Jake, I wondered if that would be something we’d explore together as well. Even though I was a bit conflicted about BDSM, I looked forward to actually seeing it at his club so I’d possibly find out if there were things I’d want to try.

I’d thought about him all day while I attended my classes, and no matter how hard I tried I just couldn’t keep him off of my mind. When I got home that evening I ate dinner, did my homework, and then waited impatiently for his arrival. We’d talked about anal sex. It was something I’d really enjoyed in the past, but none of my other partners had been as... endowed ... as he was. His size was more than a bit intimidating, but my more adventurous side wanted to attempt it just to see if I could. It was about 8:00 when my doorbell rang and I answered it.

“Hi, how are you?” I said after opening the door and inviting him in. He closed the door behind him and I couldn’t help but notice that he’d brought a small bag with him. He was wearing tight black jeans and a very sharp polo shirt. I’d also kept my attire casual; I was wearing a red floral mini-sundress with a little white thong. The hem on the short little frock fell on my upper thighs and it made me feel very sexy.

“I’m doing great, how are you?”

“I’m wonderful, now that you’re here.” I slipped into his arms and we exchanged a hot, passionate kiss. “Can I get you something to drink?”

“I’d take a Jack Daniel’s, if you have it.”

“I do; neat or on the rocks?”

“On the rocks.”

“Have a seat on the couch and I’ll get it.”

As he was making his way to the couch I went into the kitchen, got two low-ball glasses, put two ice cubes in each of them, and poured two fingers in each glass. When I returned to the living room Jake was waiting on the couch for me, and I handed him his drink before sitting next to him.

“How did your classes go today?” he asked after taking a sip of his whiskey.

“They went really well and I aced a big test ... but...”

“But?”

“You were on my mind all day,” I admitted.

He grinned. “Good thoughts, I hope.”

“Very good thoughts.”

“I consider myself really fortunate to have met you.”

“I had to kiss a lot of frogs before our chance meeting, my handsome prince.”

“I know what it’s like. I’ve never been married, but I know how difficult it is to find someone that you’re compatible with.”

“I’ve always liked being in relationships and dating has never been easy for me.”

“Yet you found your husband.”

“I did. He pursued me with a vengeance when we met, and in the beginning we were both very happy.” I paused for a moment. “Then ... you know ... things weren’t that great in the end.”

“I know you said he cheated on you. Infidelity breaks down the trust of any relationship, especially a marriage.”

“Yes, it does, it destroyed our marriage,” I said honestly.

“That’s why I wanted to be honest with you from the beginning. I wanted everything out in the open and to build something solid with you where we were both being open and honest.”

“I want that, complete transparency.”

“You’ll have it, I promise you that,” he said a little more sternly.

Every word that came out of his mouth aroused me even further, and it was as if I could feel our relationship deepening. Even though I was anxious for us to become intimate again, I forced myself to lower my eyes demurely, and just as I’d hoped he put his fingers under my chin, lifted up so I was facing him, and moved in for a kiss. I eagerly opened my mouth as soon as his lips made contact with it and he slid his tongue forward to press against mine. I sighed and let him be as assertive as he wanted to be, and he took full advantage, pressing his mouth harder against mine and putting both of his hands on my breasts.

My nipples were already erect and they rose even longer and harder as he fingered them through my thin dress. Then he slid one hand up along my thigh under my dress and his fingers glided across the outside of my thong, which was already soaked through. I let out a soft moan when he gently pushed the thin material into my vagina.

“You seem to be awfully eager,” he teased.

It was increasingly difficult to form coherent thoughts as he sensually played with my body, but I wanted to be honest and open with him. “I haven’t had much sex in the last year since my divorce, but you’re definitely reawakening my desires and I feel like we’re establishing a strong emotional bond. So yes, I’m eager.”

“I agree about the emotions; I feel them also. But maybe it’s a good thing I won’t hold you to monogamy,” he said jokingly, “I may not be able to keep up with you.”

“I’m sure that won’t be an issue,” I said sensually before looking at the bag that he’d brought with him. “You know I want to know what’s in there, right?” I teased. He leaned in and we shared another hot, passionate kiss.

“I’ll show you.” He reached into the bag, opened it, pulled out a set of three glass butt plugs, and handed the smallest one to me. It was about the thickness of a man’s forefinger, roughly 7/8” in diameter. I handed it back to him and then he gave me the second one so I could examine it. That one looked to be about an inch and a half in diameter, about the size of two fingers side-by-side and somewhat bigger than my ex-husband as best I remembered him. Again, I handed it back to him, and he gave me the largest one. It was fat, two inches in diameter at its widest point, a little thicker than Jake’s cock.

While I examined the largest plug, he took out a bottle of Astroglide and held up a single-use emena kit. “There are several of these,” he told me, “and you should use them whenever you ... anticipate the possibility of anal sex.”

“This is all ... you know ... very new to me,” I admitted. “I’ve used lube, of course, but I ... ummm ... never played with these types of toys.”

“I think you’ll enjoy it, I’ll make it good for you.”

I sensually ran my hand across his chest. “I know you will and I want this,” I whispered sexily.

He pulled me to him and we shared another hot kiss. When he broke our passionate embrace I stood up, took his hand, and looked deep into his eyes. “I’m ready, let’s try this, okay?”

He smiled, grabbed the bag, and then stood up. Hand-in-hand we walked into my bedroom. When we were standing in front of my bed, I squeezed his hand. “I’ll go into the bathroom and try to figure some of this out,” I said teasingly while taking the bag from his hand. “Why don’t you get undressed and get into bed, and I’ll be back in a couple of minutes.”

“Sounds like a plan.”

We exchanged a hot little kiss and I went into the bathroom. After I undressed, I used a couple of the disposable enemas to clean myself out. Then I used a douche to ensure I was squeaky-clean down there. Once my preparations were complete, I thought of putting my little sundress back on but then decided against it. It didn’t make much sense to wear clothing when I’d be removing it in a couple of minutes anyway. The butterflies were churning nervously in my stomach. I’d never engaged in this type of anal play before but I was incredibly anxious to try. I already trusted him and I knew he’d make it good for both of us.

I stepped back into the bedroom carrying his bag and saw he was already undressed and sitting on the bed. When I came into his view, his eyes sensually traveled up and down my naked body, drinking me in. “So whaddya think?” I said shyly.

“You’re the most beautiful thing I’ve ever seen.”

I smiled. “Thank you, and I’m all yours.”

“Come here, pretty girl,” he said huskily.

I glided across the room and slipped onto the bed beside him, setting the bag next to me. He pulled me to him and we shared a long, hot, passionate kiss. As our tongues played inside each other’s mouth his hands roamed up and down my body, and already I could feel my vagina begin to moisten. His hands pawed at my large breasts and then he moved one of them lower and began to gently rub the lips of my pussy. “You’re already wet,” he said, whispering into my ear. He eased a finger inside me and then started slowly moving it in and out.

“Yes, I am, and I want more.”

“Tell me what you want,” he said a bit more commandingly.

It was getting increasingly difficult to concentrate and carry on a conversation with him, but I willed my mind to somewhat focus. “I want you to play with my body in whatever way that pleases you,” I said demurely. I’d never acted this way before with anyone. He seemed to love being in control, though, and I realized that more than anything I wanted to give him that control.

“Get on your hands and knees, Hailey.”

My knees went weak. “Yes, Sir.”

I pushed myself away from him and moved to the center of the bed. Then, just like he’d instructed, I got on my hands and knees. He grabbed his little bag and then moved in behind me. The anticipation of what he might do next was almost too much for me to take. My pussy was a warm wet tunnel and I could feel my secretions oozing out of my sex and dripping onto my inner thighs. He moved his fingers through my wetness, collecting some of it. When I looked over my shoulder, he was licking his fingers and making pronounced slurping sounds. “I love how you taste,” he said sensually. Just as I was about to respond, he slid two fingers inside me and I let out a little grunt.

“That feels so good,” I whispered.

He continued to ease his fingers in and out of me at a slow, tantalizing pace and it felt like I was slipping in and out of consciousness. “You’re so tight, I can feel your pussy gripping my fingers.”

“I love what you’re doing to me,” I said breathlessly.

“Put your head down and keep your ass raised as high as you can,” he said a little more sternly.

“Yes, Sir.” I grabbed two pillows, laid my head down on them, and then raised my ass as high as I could. He eased his fingers out of me and then wrapped his arms around my thighs. I felt a long string of his saliva land on my asshole and some of it dripped down into my vagina. Using the tip of his tongue, he gently lapped at my puckered little hole. Instantly, lighting bolts shot through my core and I let out a deep moan. Gradually, he used the tip of his tongue to push his saliva into me. “That really feels good,” I whimpered.

With his arms around my thighs holding me still he began pushing his tongue deeper into my ass. I’d never had a man do this, engage in this type of sexual act with me. It was different, having a man play with the most intimate part of my body in that way, but I loved both the sensations and the fact that he was so willing to do those kinds of things with me. I could feel my vagina moisten further, and I began to push my hips towards him in an attempt to get his tongue deeper inside me. A few seconds later, I felt his tongue probe into me as deep as it would go.

My breathing became shallow and ragged. Slowly, I eased my hand to my vagina to rub my clit, but he withdrew his tongue and gently grabbed my hand, arresting my movement. “I need to touch myself,” I whispered.

“You’re so needy, aren’t you?” he teased.

“Yes, I am, and I need more.”

“I know you do and I’ll give you more.”

I looked behind my shoulder and watched as he dug into his little bag and pulled out the smallest glass butt plug. A shiver coursed through my body when he ran the end of the piece of glass through the lips of my pussy, wetting it, and then slid it over my clit. Then he brought it up to my asshole and slowly teased the end of it in and out for several seconds. I took a deep breath and tried to relax as he eased the plug inside me. In an instant I felt very full, and the sensation was nothing like having my ex’s finger inside me. “Roll over onto your back,” he said smoothly.

I slid onto my back and then opened my long legs wide for him. He got onto his stomach and once again wrapped his arms around my thighs. Teasingly, he began licking my secretions off the inside of my thighs. My pussy felt like a hot, wet swamp. The feeling of his tongue on me in combination with the pressure of the butt plug was almost more than I could take. “Please ... please put your mouth on me,” I begged.

Using the tip of his tongue, he slowly licked up and down the swollen lips of my vagina, and instantly little eruptions went off in the pit of my stomach. My breathing quickened when he extended his tongue and sank it deep inside me in one swift motion. I began to moan and pant when he plunged his tongue into me over and over in rapid repetitions. Then he eased his tongue out of me and swirled it over my clit, and I was overwhelmed by the suddenness and intensity of my release. My body shook and quivered, and only his arms around my legs prevented me from lurching upwards.

He kept his lips and tongue moving and I climbed higher and higher, and then he quickly slid his body up and inserted his thick cock into me in one swift motion. The combined feeling of the plug in my ass and his cock in my pussy was incredible, and I screamed in extreme ecstasy and exploded into another massive orgasm. Just as I was coming down and my senses were returning he grabbed my thighs, lifted my ass up off the bed about a foot, and began pounding me hard and fast. The plug inside me only amplified the intense sensations that were coursing through my body. As he pounded me out, I could feel his cock rubbing against the thin wall that separated my pussy and asshole, adding pressure on the glass plug. It was a different feeling, but one that I couldn’t get enough of.

His body began to stiffen and his breathing began to change and I knew he was getting close. I slid my hand between my legs and began furiously rubbing my clit so I’d release with him. As I felt powerful spurts of semen flood my vagina, my body began to shake and convulse and my world went dark as another powerful orgasm overwhelmed me.

Just as my senses were returning I found that he’d collapsed on top of me and was trying to catch his breath. Then he slid off of me and gently eased the glass plug from my asshole. He pulled me tight against his body and held me, making me feel so safe and secure, and my world felt perfect. I let out a little moan when he slid his thigh between my legs, held them open, and pulled me even closer against his body.

“That was just amazing,” I said shyly.

“Yes, it was,” he said in agreement.

We lay together for a couple of minutes, just bathing in the afterglow. I felt so calm and comfortable with him. I really loved that we could enjoy a few moments of comfortable silence without saying a word to each other. However, there was something on my mind that I needed to share with him. “Maybe at some point you could ... you know ... take me to see your club,” I whispered.

His eyes widened. “Would you really like to see it?”

I was curious but also nervous. I didn’t know whether I’d be shocked or excited by what I’d see, but I had to find out. So I put on a brave face. “Yes, I would. I want to know everything about it.”

“If you’re willing, I’m more than happy to show you.”

“Thank you. What do people wear when they visit the club?”

“Mostly club-like attire.” He thought for a moment. “Women wear short party dresses, or skirts with tight tops, and high heels. The men wear nice pants and collared dress shirts.”

I had some clothes similar to what he was describing, but it had been a while since I’d been to one of those types of clubs on the Strip. I might have to do a little shopping, I thought.

“So you’d want me to dress sexy for you?” I whispered.

“I’d love that, but I also want you to be comfortable and feel like you ... fit in,” he said a little more seriously.

“If I’m with you, I know I’ll be at ease.” I paused, then asked, “What will we ... you know ... be doing once we’re there?”

“I have security that makes the rounds and ensures everyone is staying safe and abiding by the club’s rules, so mostly I monitor the CCTV and keep an eye on everything that’s going on.”

I giggled. “I have a feeling it’s not all about keeping everyone safe; you like to watch them, don’t you?” I gently teased.

He looked down shyly and then his eyes once again met mine. “I admit it, I’m a bit of a voyeur and I do enjoy watching the people in action.”

His words, all the things he was telling me, were very arousing. I’d never watched anyone having sex or allowed others to watch me. I’d always been very curious about exploring new things and being less ... ummm... vanilla in the bedroom. I couldn’t help but think that going to Jake’s club would open up new worlds for me. “When can we go to the club?”

“The weekends are the most active nights of the week. Do you have any plans for Saturday night?”

“Yes, I do.”

“Oh ... ummm ... I see,” he said.

I could tell how disappointed he was until I broke into a little laugh. “I’m going to be going to your club,” I said saucily.

He laughed. “You like messing with me, huh?”

“Yeah, I kinda do.”

“We’ll have a fun night on Saturday, I promise,” he said reassuringly.

“I know we will, baby.”

He pulled me into his arms and then I flipped over and he spooned me tight against his body. It felt so good being a part of something again, being in a couple and finding someone who thoroughly pleased me sexually. My world felt perfect, and I hoped that going to his club would only deepen our bond and strengthen our growing relationship...

Over the next few days I repeatedly lubed and inserted the middle-sized plug and then, slowly and carefully, the biggest one. By Saturday afternoon I was completely comfortable walking around my apartment with that huge plug in my ass, and I knew I would be able to take Jake’s big cock in there without any problems.

I spent most of the day on Saturday pampering myself with a visit to my favorite spa. After receiving a facial, I got my legs and my intimate areas waxed. Once I got home, I showered and douched and then performed my little clean-out routine with a couple of enemas.

After that, I ate a small salad and then put on a silky little black thong and a very short, sexy, spaghetti-strap club dress that I’d purchased the day before. The little frock had an exposed back, so I couldn’t wear a bra with it, but I didn’t need one; my big breasts were firm and perky enough that I could go without, and I wanted as few obstacles as possible in the way if Jake decided to be frisky with me at the club. I put on my tall ankle-strap stilettos and waited anxiously for him to pick me up.

Jake arrived promptly at 6:30, and after he rang the doorbell I opened the door and watched as his eyes traveled up and down my body, drinking me in. “You look good enough to eat, honey,” he said with a lustful little grin.

That’s the plan. “I’m glad you like it,” I said shyly. I’d worked so hard to look good for him and it felt great knowing that he appreciated everything I’d done. “You clean up very well yourself, kind Sir.” He really did look very handsome. He was wearing black dress slacks, a pressed white shirt, and a sharp black sports coat.

“Thank you,” he said smoothly. He pulled me into his arms and we shared a long, smoldering kiss. “Are you ready to go, honey?”

“You bet, let’s do this,” I said excitedly.

He took my hand in his and led me out to his Cadillac Escalade. He opened the door for me and then strapped me into the seatbelt. I had to admit I loved the very subtle control that he always exhibited when I was with him.

About half an hour later we arrived at his club on Industrial Road. He opened the door, turned on some lights, and led me a short way down a hall past a reception area to a big, nicely-furnished office. There was a big desk with a computer monitor and keyboard and an executive chair. A side chair stood next to the desk, and across the room a couch, an easy chair with a large ottoman, and a coffee table were arranged as a sitting area. An enormous big-screen TV was mounted on the wall above the couch, and he showed me his private three-quarter bath that included a big walk-in shower with a bench inside it along one wall.

Jake took me into the main club room and introduced me to the staff people as they arrived. Tommy came in first, then Felice, and then Sara and Darren walked in together holding hands. Both of the guys were the very embodiment of tall, dark, and handsome, and Felice was very attractive, but I was immediately drawn to Sara; there was just something so sultry, so damned sexy, about her, the way she moved, that was just amazing. I’d always appreciated how some women looked from afar but I’d never found the courage to actually act on any of those feelings. However, it felt like Jake was opening up new worlds for me, and I couldn’t help but wonder if at some point I’d have the opportunity to explore those feelings.

I was glad I’d dressed provocatively because the two women in front of me were wearing short, sexy little print dresses and high heels. I felt like I could blend in with them if I was able to move around the club later; that, of course, would be up to Jake.

I stood quietly and watched as they went through their pre-opening routines. Felice opened the snack bar and started coffee brewing while Sara went to the reception area and fired up the computer there. Darren and Tommy did a walkaround through the entire facility and then Darren went into the security office and Tommy took up station in the main room. I went back to Jake’s office and he joined me there a couple of minutes later.

Tommy unlocked the front door of the club promptly at eight o’clock, and soon thereafter the members started to arrive. Felice was at the reception desk checking them in. Jake pulled the side chair around for me and we sat next to each other at the desk in his office. I watched as he used the keyboard to switch from one CCTV camera to another in the main room of the club every 30 seconds or so. Most of the members were sitting or standing and chatting with others, but there was already one pair of couples on opposite couches starting to become ... erotically entwined. It was fascinating to see them casually start to make out and slowly undress each other while all around them other people either observed or simply ignored what was happening.

I asked Jake to keep displaying those couples and he complied. I had seen some porn over the years, but this was much different. These weren’t paid actors, they were real people. I’d never thought about the mind-set of either a voyeur or an exhibitionist, but these couples were obviously comfortable with being watched, and as an observer I realized that I was finding the scene, the whole idea of watching, highly arousing.

“This is amazing,” I whispered.

“It doesn’t appear to be turning you off,” he said with a grin.

“No ... it’s just the opposite,” I admitted. I already felt little tingles between my legs and I knew from past experience that moisture was building under my little thong.

“Really? You’re enjoying watching my members?”

“Yes, I am.”

Then one of the women stood up and removed her dress, and her partner quickly got out of the way as she laid herself out lengthwise on their couch. Her erect rosy-pink nipples were poking through her long red hair, and when she spread her legs wide, placing one stiletto heel on the back of the couch and the other on the floor, I could see that the her neatly-trimmed fiery-red pubic hair matched the hair on her head. While she rubbed her pussy in anticipation, the man stripped, and then he lay between her thighs and inserted his average-size cock into her glistening pussy.

The other couple had stopped kissing and turned to watch the action; her skirt was up around her waist, his fingers were in her vagina, and her hand was slowly stroking up and down on his stiff six-inch cock that was protruding through his unzipped fly. I stared at the screen, intently watching the two couples, and as the one man began pounding the redhead, slapping his chest against her large breasts faster and faster, my fingers slid under the short hem of my dress and I started edging myself, rubbing my hard little nub through my thin silk thong.

When it became obvious the two people sexually coupled on the couch had each reached orgasm, Jake put his hand on mine and held it still. “Not yet, honey, the night is young and there’s a lot yet for you to see.”

His taking control made me breathe harder and I really wanted to release. “Oh, please, just a little one,” I begged, but he just sat silently beside me, holding my hand and keeping me from climbing any further, and I relaxed against his body. “Okay,” I said in a voice that was half regretful and half respectful, “I’ll be good ... for now. Please resume changing the view; I want to see what else is going on.”

“Okay,” he replied, and he started shifting from camera to camera on the big screen again. After several more changes my attention was drawn to a young couple who appeared to be in their early 20s, so I asked Jake to stop again. They were dressed, as were most of the members, in club attire; she was in a sexy little Bodycon halter-dress and high heels and he was wearing slacks and an open-collar dress shirt. They were standing and conversing with an older couple seated on a couch. The seated pair looked to be in their 40s and they were wearing more conservative versions of the same kinds of clothing. The disparity in ages of the two couples kind of startled me, so I asked Jake what he knew about them.

He smiled at me. “The younger couple isn’t actually a couple in the usual sense; they’re a brother and sister.”

I gasped in surprise and burst out, “Do they have sex with each other? That’s incest!”

Jake gave me a funny look. “Yes, they do. They’ve been doing that since they were teenagers; he was 16 and she was 15 when they started, but they were both over 18 when they started coming to the club. And that bothers you because?”

I had to stop and think. “I guess it’s because I’ve always been told that incest is ... wrong, immoral, you know?”

“Some people think so, especially from a religious perspective,” he replied seriously, “and there are potential genetic risks to inbreeding if pregnancy should happen. But some people take precautions against that and have a loving relationship with their relatives to the extent of enjoying a physical as well as an emotional attachment to them.”

That answer gave me pause, and I had to carefully consider what he’d said. I’d always thought I had a very liberal attitude when it came to sex, but after what Jake told me I wondered if maybe I was a little more vanilla than I realized. Incest was obviously something that Jake accepted, at least to the extent of not objecting to it at his club. “I ... never thought about it until now; I suppose it’s ... okay if everyone is ... you know... okay with it.”

“It gets even more interesting,” Jake said. “The older couple pays for the young people’s membership.”

“Really? Why do they do that?”

“They do it because they are their parents.”

“You’re kidding! Do they all have sex together?”

“Yes, sometimes they do. They all swing with other people, but sometimes it’s father-daughter and mother-son sex as well, both at the club and, from what they’ve told me, at one of their houses.” He looked more closely at the screen. “I think the four of them are going to go at it now; let’s watch them.”

The older couple rose and the four people moved to a different part of the room where they found two unoccupied facing couches separated by a coffee table. I watched in breathless wonder as the father took his daughter in his arms and kissed her passionately. Then the mother clasped her hands behind her back and gave her son a lustful look, and he put his hands on her upper arms, pulled her towards him, and locked his lips possessively onto hers.

“Oh, boy,” Jake exclaimed. “Janice is in one of her submissive moods.”

“What do you mean?”

“Sometimes she likes to be ... handled roughly.”

Something else new to me. “And is that ... like ... part of your ... ummm ... other interest?” I asked warily.

“Yes,” he said without a trace of embarrassment. “I suspect Jim will take her to the dungeon before the night is over.”