Tales From Fantasy Island Ch. 09

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Ağu 8, 2022 // By:analsex // No Comment

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Author’s Note: This story is a collaboration with my friend and editor, Harvey. We both contributed equally to its content and we hope you enjoy it.

Chapter 9


I always dressed to please Jake even when it was just during the day and I was going out to buy groceries. So after my morning shower I put on a front-hook half-bra, a thong, a pretty pink lace top, a black pleated knee-length skirt, and four-inch heels. Without really thinking, I buckled on a matching leather collar. People might think that pink collar belonged on a female toy poodle, and I smiled at the twisted analogy. I’m not a bitch, I thought, but I am a kind of toy.

I got into Jake’s Beemer and drove to Whole Foods. As I was tooling through the store I passed a woman about my age standing in one of the aisles. She was in my economics class and we’d actually made a little small talk a few times before our class started. I found it interesting that she was dressed much as I was. We may have been the only two women in the place wearing skirts; I’m sure we were the only two in stilettos. A couple of aisles later, I stopped next to her and reached for a bottle of ketchup.

“It’s Hailey, right?” she said as her eyes traveled over me. She stared at my collar; then, when I turned toward her, she blushed and looked away.

“Yes, and you’re Heather, correct?”

“Yes.” She blushed even harder, then fought for composure. “I’m … ummm … very sorry,” she apologized. “I shouldn’t have stared at you like that.”

“It’s okay, I’m just trying to get the weekly shopping done.”

She gave me a friendly smile. “Yes, me too.” She paused for a moment as she looked into my eyes, then her glance moved just a little lower. After a brief pause, she said quietly, “May I ask you a question, a personal question?”

Now I was curious. “Yeah … ummm … sure.”

Her eyes dropped to the collar around my neck and she blushed again. Then she looked up and spat out, “Is that … you know … what I think it is?”

I was fairly certain that I knew what she was referring to, but I didn’t really know how to answer her. So I decided to answer her question with a question. “What do you think it is?”

“Is that … ummm … a … a … a slave collar?” she stammered.

Now a deep blush was breaking over my face. I always dressed very casually when I attended classes and I never wore a collar on campus. Had I known that I’d run into someone I knew I definitely wouldn’t have worn it today. My first instinct was to lie, but she’d always been very friendly to me even though I hardly knew her. In the end, I decided to answer truthfully. “Yes, it is,” I whispered.

“Oh, my,” she whispered back. Then she shocked me when she continued, “It’s been so long … I’ve fantasized about …”

This is crazy, I thought to myself, but now that I’m into this conversation I’m really curious. “It’s been so long for what?”

She started shaking a little, like she was holding back tears, and she nervously looked up and down the aisle to ensure there were no eavesdroppers. “Please,” she whispered, “can we find someplace private to talk?”

“Sure,” I answered. “Let’s check out and go somewhere else.” We went into a mostly-deserted Starbucks inside the shopping area of the Whole Foods. Once we got our coffee, we sat down at a little table and she told me her story.

“My husband’s name is Larry,” she began, “and we’ve been married for three years.” I sipped my coffee and listened intently as she continued. “We’d both … you know … been with other people before we met, and we had a very good sex life from the beginning. We still do … sort of.” she suddenly stopped talking, apparently embarrassed by what she’s just said.

I was a little taken aback. What she was sharing was going way beyond the small talk we’d previously exchanged. “Okay, I think having sex prior to getting married is fairly common,” I gently teased. “But what does sort of mean?”

“Well … ummm …”

I lowered my voice just a little even though I was fairly certain that we couldn’t be overheard. “Does this … you know … have something to do with my collar?”

She looked down at her cup, sipped from it, then looked up into my eyes. “The sort-of part and the collar are related. Ever since I was a teen I’ve read romance novels, and some of those bodice-rippers got me … aroused, got me … fantasizing about being overwhelmed by a strong-willed man.”

Now she’s arousing me. We obviously had a lot in common, more than I’d ever realized. “Being with a strong man can be intoxicating,” I admitted. Being with a strong woman is also a lot of fun, I thought, but I was in no way ready to admit my bisexual interests to her.

“I haven’t experienced that yet, but I love reading stories online and I even created an account at a website called Fetlife where I could do a little research and chat with other women who had similar interests.”

“Oh, I’ve never heard of that site.” The only times kurtköy olgun escort I went online were to complete my college coursework, and Jake was teaching me everything I’d need to know about the lifestyle.

‘It’s interesting, you should check it out sometime.”

“Yeah … ummm … maybe I could.” I took another sip of my coffee. “So, what does your husband … you know … think about all of this?”

“I’ve talked with Larry about doing some kind of role-play or something, but he’s just not interested. I won’t say I’m obsessed, exactly, but our … sex life has become really … routine and a little boring.” She paused for a moment. “Maybe even predictable.”

“I understand how that can happen; I think that’s partly why I’m no longer with my ex-husband.”

“So you know what I mean, right?”

“Yeah, I do.” I’d often wondered if that was one of the reasons that my ex cheated on me. I was fairly certain that he got bored and then looked elsewhere instead of trying to improve things with me.

“But you’re wearing that collar now, so something obviously changed.”

“The man I’m … with now has shown me, taught me, a lot about myself and about how some people … do things … differently.”

“Is he that kind of … powerful man?”

“Oh, definitely,” I said with a smile. “His name is Jake, and before I met him I never would have thought of myself as a … you know … submissive.”

Her eyes widened. “It sounds like you’re really deep into … this.”

“Yes, I am,” I admitted.

“I know some things about the lifestyle, not everything but some, and I know what your collar signifies.”

I could feel a little blush breaking over my face, but I quickly recovered and regained some of my composure. It was still difficult to admit this, especially to someone that I didn’t really know very well. “He owns me, I’m his property … basically, I’m his.”

Heather was squirming a little in her seat now. It was very apparent that everything I was telling her was turning her on. “He sounds very exciting.”

“I’ve never met anyone like him and I’ve never been so happy. I never thought I’d be doing anything like this, but now I … you know … I can’t picture my world without him in it.”

“I have to admit I’m more than a little envious of you.”

“I wasn’t looking for a man like him and it really happened by chance, but I’m so glad we found each other.”

She looked at her watch. “I have a pilates class in half an hour, but maybe we can exchange numbers and … you know … talk again sometime?”

“I’d love that, Heather.”

We pulled out our cellphones and exchanged them and added each other into our contacts. When we stood up, we exchanged a little hug. “I’m so glad we ran into each other today, Hailey.”

I smiled. “I’m glad we did too.”

– – – – –

When I got home I unloaded the groceries and put them away, then went into Jake’s home office. He got up from his desk, hugged me tightly, and we exchanged a deep passionate kiss.

“I think you might have missed me,” I said saucily.

He pulled me in even closer, and I loved feeling his hard body against mine. “Of course I did.”

“Well, we can fix that, but first I have something to tell you.”

He took a seat in the executive chair behind his desk and I sat in front of him in one of the other chairs. “Okay, what is it?”

“I ran into a woman from my economics class when I was shopping for groceries.”

“Ummm … okay …”

“I’m not sure why, but I wore my collar today and she knew enough about the lifestyle to know what it signified.”

He grinned. “That must have been interesting, then.”

“I was a little embarrassed at first, because most people have no idea what it is and what it means.”

“Yeah, I’m sure that’s true.”

“I guess my point is that she knew and it sparked an interesting conversation when we had coffee later.”

“Oh, you had coffee with her?”

“Yeah, we needed to find a place where we could have some privacy; it wasn’t something that we could discuss in the middle of the grocery-store aisle.”

He laughed. “Yeah, I can imagine.”

“So while we had coffee she told me that she was unhappy because she has submissive fantasies and her husband won’t act on any of them. From what she said, he’s really not into that.”

“That is interesting.”

“She’s obviously unhappy about it. We exchanged numbers and I told her she could call me if she wanted to talk. I think it helped her to get some of that out, but I have no idea if she’ll call me.”

“I guess we’ll just have to see if she does. Now get out of those clothes; I have something interesting I want to do with you.”

“Yes, Sir,” I replied enthusiastically; I was always up for Jake’s interesting ideas.

– – – – –

It was Monday evening and I walked up to the front door of Sara’s apartment. After I rang the doorbell, she opened the door. “Ohmigod, girl, there’s that dress again,” she cooed.

I tuzla escort blushed. Just as I’d promised, I was wearing the little cut-out dress that put a lot of my body on display. “I wore it just for you,” I said sensually. We exchanged a little hug and a deep kiss before she invited me into her apartment.

“Have a seat on the couch, I’ll get us some wine, okay?”

“That sounds great.”

I took a seat on her couch and watched her sexy bottom move as she sashayed into the kitchen. She was wearing tight little jean shorts and a tank top without a bra. When she returned with an opened bottle of wine and two glasses, I noticed that her nipples were hard and poking out into the thin material. She’s just as excited as I am about this, I thought. She sat down next to me and our thighs gently touched as she poured us each a glass of chilled Kim Crawford Sauvignon Blanc. “So how did your evening go with Jake and the other guy?” she asked.

I took a sip of my wine. “It went really well, I loved it.”

“You gotta start dishing, girl,” she teased. “Who was the guy?”

“His name was Richard, you know him?”

“Big-cock Dick Leadon, of course I do. All the women in the club know him.”

I giggled. “Yeah … well … he lived up to his reputation, that’s for sure.”

She laughed. “I know from experience that Jake isn’t small either; how did you manage all of that?”

“They went slow for me when I needed them to, but it was almost more than I could handle at times,” I admitted.

“And you took them … you know … together, or what?”

I could feel my face heat up. I was very close to Sara and we were always very forthright when it came to our sexual escapades. In the end, I didn’t have a problem sharing the intimate details of that experience with her. “Yeah, at the same time,” I whispered.

“Damn, girl, that’s slutty as fuck,” she quipped.

I laughed. “Don’t tell me that you wouldn’t try a little of that too if the opportunity presented itself.”

“Of course I would.” We each took another sip of our wine. “So like the same time as in your vagina and …”

“Yes, just like that.” I paused for a moment. “If I was going to try something like that, I wanted the whole experience.”

She was squirming in her seat a little now and her nipples were poking even more prominently into her little tank top. I could tell she loved hearing about all of this and it was really turning her on. She reached over and gently rubbed my exposed thigh. “You know I’m a little envious, right?”

“You and Darren could always talk to him, set something up.”

“He and his wife are very selective.”

“Yeah, I guess they are … but … “

She looked deep into my eyes. “Damn, you talked about that too?”

“He brought it up, actually. He said that his wife would like me and … you know … I got the feeling that he wanted to be with me again.”

She smiled. “Of course he did. How do you feel about that?”

“I’ve never met his wife, I’ve only watched her on the CCTV system, but she’s really pretty and …”

“And what?”

I took a deep breath. “Dick is big, even bigger than Jake, and … you know … I think I’d like to be with him again.”

She slid her hand up my thigh underneath the hem of the little dress and the tips of her fingers brushed over the wet lips of my pussy. “You’re thinking about him right now, aren’t you?”

“Yeah, talking about him like this … I am,” I admitted.

She eased a finger inside me and I let out a little moan. “What about his wife? Do you want to be with her too?”

“I’ve only watched her once, and she was taking on two guys.”

She gently moved her finger in and out of me and I was finding it increasingly difficult to concentrate on our conversation. “She’s really pretty, huh?”

“Yeah, she is. Almost as beautiful as you.” This was bringing up some important things that we’d never really discussed. I placed my hand on hers and slid it back so she wasn’t fingering me any more and I could focus a little better on her. “How do you feel about all of that?”

She took a deep breath. “Can I be honest with you?”

I squeezed her hand. “I expect nothing less from you.”

“Sometimes it’s a little difficult. I have … you know … feelings for you, Hailey.”

I took a deep breath. I was fairly certain I could see where this was going. “I have those same feelings for you too. You’re my best friend and I love being with you.”

“I love it too.”

“I want us to continue, but I’m … you know … since I met Jake it’s been like an awakening, a sexual exploration where I’m experiencing so many new things.”

She grinned. “Yeah, you’ve been running wild, girl.”

Just like Jake, she had a way of making me feel like a little girl. “I guess I have, honey, and more than anything I need you to be okay with that.”

“Sometimes it’s … you know … hard for me.”

“I know it is, but I don’t want to lose what I have with you, okay?”

“I pendik escort don’t want to lose it either.”

“Good, you won’t, but I need you to be understanding and accepting with me, okay?”

“I’ll get there, I promise.” She leaned in and we exchanged a hot passionate kiss. While our tongues urgently explored each other’s mouths, she slid two fingers deep inside me and I let out a little moan. “You’re so wet for me, aren’t you?” she said huskily.

There were little sloshing noises emanating from between my legs as she worked her fingers in and out of me. “I am and I need to feel more than just your fingers,” I said through little sips of breath.

Sara eased her fingers out of me and then brought them up to her lips and sucked my secretions off of them. “I love how you taste, do you know that?”

A little blush broke over my face. I’d loved that we had a chance to talk and reconnect, but now … I needed more. “Take me to your bedroom, Sara,” I said huskily.

She stood up, took my hand, and helped me up off of her couch. “C’mon, pretty girl.” We walked down the hallway and into her master bedroom. Once we got there, she sat down on the bed and her lustful eyes met mine. “Undress for me, Hailey.”

I slipped the little dress off, exposing my naked body to her. When I reached down to take off my heels she stopped me. “Leave them on for me, baby,” she purred.

My eyes widened and then I broke into a little smile. The whole vibe in the room was different from what it had been previously. She was being very subtle, but I could feel her taking more control over me. “Okay, I whispered. Then, slowly, she began undressing for me. She slipped off her tank top, exposing her large breasts. Then she slid her tight jean shorts down her thighs and opened her legs. The lips of her vagina were red and swollen with just a hint of moisture on them. She scooted back to the middle of the bed and I slid on top of her. Instantly, our lips fused together and we shared a deep passionate kiss. As our breasts sensually crushed together, she slipped her thigh between my legs and I opened them wider for her. I let out a little moan when she began grinding her thigh on my pussy.

“Put your mouth on me, Hailey,” she said huskily.

I slid a little ways down her body, took her erect nipple into my mouth, and began to suck on it. I loved hearing the little moans and gasps coming from above me. I moved further down her body and nestled between her legs. The lips of her vagina were wet and open and there was even some moisture seeping onto her inner thighs. Teasingly, I ran the tip of my tongue through the little stream of wetness and then gently bit her inner thigh. She wove her fingers through my long blonde hair and then guided my mouth to her vagina. “Please … baby … I need this so bad,” she whimpered.

I extended my tongue and sank it deep inside her. Her thighs closed around my head as I licked the walls of her vagina. Taking a little more control, she began grinding her pussy into my mouth, covering my face with her secretions. I kept my tongue out and flat and she rotated her hips forward, fucking her pussy with my tongue. I reached up and took her breasts in my hands, pawing them roughly. I eased my tongue out of her, took her clit into my mouth, and gave it a few hard sucks while pinching her nipples. Instantly her body began to quake and convulse, and I quickly withdrew my tongue from her. I gently licked and sucked on her inner thigh, which gave her time to recover and get her breathing under control. “God, girl, are you trying to kill me?” she teased.

“No, I’m not, but you liked it, right?”

“I loved it, every second of it.” I moved up her body and slid into her arms, and she pulled me tight against her. When our eyes met, we shared another hot kiss. I was slowly getting more comfortable being with a woman, and her liking what I did only helped build my growing confidence. “You know I’m going to want more of that,” she teased.

“I’ll give you as much as you can handle, honey,” I said softly.

She pulled me tighter into her body and I loved the way our sweat sensually mixed together. “Okay, it’s your turn, are you ready for this?” she said.

I giggled. “Yes, I am.”

She slid away from me and then got on her hands and knees. “I want to feel your mouth on me, pretty girl,” she said sternly. I moved in behind her and got onto my knees. I ran my hands over the globes of her cheeks and she let out a little moan.

“You have such a beautiful ass, do you know that?” I cooed. She was taking deep sips of breath and I could tell it was already difficult for her to respond to me.

“I’m glad that you like it, baby,” she purred.

I wanted to tease her just a bit more so I gently bit each cheek, leaving little teeth marks in her tanned flesh. “God, that feels so good,” she murmured. She rested her head on a couple of pillows, reached behind, and pulled her ass cheeks apart, exposing the most intimate area of her body to me. Her secretions were oozing out of her and were beginning to run onto her inner thighs. Sensually, I extended my tongue and ran it through the little stream, tasting her. She tasted tangy and just a little sweet. Without warning, I extended my tongue and sank it deep inside of her. “Oh, God,” she murmured.

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