tagGroup SexPleasure Island Ch. 02

Pleasure Island Ch. 02


The creators and core group of Pleasure Island meet and start building their lifelong relationship.

Please note: All characters in this story are over 18 years of age and all sex between the characters are carried out in a safe and consensual manner.

Chapter Two

Angelique - October 2005

Evelyn Simon burst into Stephen's office late on a Thursday afternoon, apologizing profusely for being so late. Her captivating beauty took my breath away and for a long moment, we were both speechless. Getting myself back together, and drawing my eyes from her magnificence, I let her know she was either in the wrong office or had a wrong date and time.

Almost like she hadn't heard me, she continued on and handed me her business card giving me her basics; her name, phone number and the puzzle fitting piece - she was a pharmaceutical rep. I immediately knew she was using the harried/apologetic approach as an attempt to get her foot in the door. I'd been around the medical profession long enough to know every trick most of the pushy sales reps used.

"I'm sorry," I said, "but Dr. Westminster isn't here." ...but, I thought to myself, I'd be more than happy to help you out.

I couldn't decide if she was hypnotizing me with her seductive eyes, ultra-feminine appearance or perfect large breasts I'd ever seen or if she was simply laying it on thick as part of her sales tactic. Whatever it was, at that very second I could have spent a lifetime getting lost in her. My one-track mind was hoping she enjoyed women because I had images of the things I wanted to do to her with my mouth and tongue.

My attraction to Evelyn surprised me. I'd never been so unexpectedly drawn to a complete stranger before but I wasn't going to let it deter me at one bit. It had been a long time since I felt such raw desire.

It hit me like a bolt of lightning when I took one of those brief frozen seconds in time to let my thoughts wander to the last time I felt such excitement over meeting someone. It was the night I met Stephen at one of David and Nancy's get-togethers...


That fateful and wonderful sex filled night with Stephen happened six months after I joined Nancy and David's group of friends. Stephen and David met during their medical school days at Harvard where they discovered their bisexual sides together. It was a lucky 'planned' coincidence they were able to get their residencies at the same hospital in San Francisco since neither was ready to give up the comfortable relationship they'd developed over the years. Regardless of the fact David was head over heels in love with Nancy, he also cherished his man time with Stephen. Fortunately for them, Nancy was bisexual too and didn't mind David's flirtations.

Nancy gaged her pleasures on the women she enjoyed outside the confines of her marriage. The only man Nancy ever slept with was David, which totally surprised me. Stephen was such a big part of their life and he was so sexy and gorgeous.

Even though I didn't know it at the time, I quickly found that in some cases size did matter and Stephen was miles ahead of David. I'll never forget the spasms I felt the first time his full length and thickness slipped into me. I loved feeling so full.

Like his wife, who never slept with the men, David rarely fucked other women. I was one of the rare exceptions and it was something we never talked about or did on Booty Call nights. David totally reserved those nights solely for men. Up until the night I met Stephen the few liaisons I had with David were normally dinner and sex with him and Nancy on Tuesday or Wednesday evenings and if our schedule permitted, which wasn't very often, one other night during the week. He normally preferred to watch Nancy and I together but knew I had my needs and dutifully stepped up to fill them.

The added fact that he always came the hardest right after I soaked him with my plentiful juices kept him coming back for more. I was an anomaly for them. Not only was I youngest and most eager woman to come to their bed, I was the only woman in the group that squirted and they both found that deliciously hot and sexy.

It was through their collective love of their bisexuality they founded the 'Booty Call Group'. The group of people who shared a common thread, they were all bisexual and enjoyed having safe, consensual, and more importantly private sex liaisons. Depending on the time of year the group normally met every other weekend on Saturday nights which normally carried over to Sunday brunch. During the holidays and summers sometimes the parties were delayed an extra week or two but they normally never went more than three weeks without meeting.

Stephen wasn't a frequent visitor to the group. He preferred his time with David to be one-on-one or with Nancy. He told me after we met he woke up the Saturday we met hornier than a Bonobo chimpanzee and even though he masturbated twice before getting out of bed he still wasn't satisfied.

The attraction between Stephen and I was instantaneous. So much so, it took every ounce of restraint not to invite him to have me within minutes of being introduced. I knew it was proper decorum to wait a respectable amount of time before seducing him. I bided my time until the dinner, the 'clothed' socializing part of the evening came to end, an interminably long hour and forty-five minutes. We were both more than ready after I spent a good part of the dinner with my hand in his lap teasing and torturing his horny cock. The moment people started moving to the living room to begin shedding their clothes, I led him by the hand to the nearest bedroom. We didn't even bother stripping our clothes off, I unzipped his pants and pulled my skirt up and in one swift move was on him. We both moaned in unison over the most perfect fit we ever felt.

Stephen was the total opposite of David, something I wasn't aware of until the moment Stephen and I came together in a screaming orgasm that left us panting and only wanting more. I truly cared for David, especially everything he did for my mother and me, but as a lover, I discovered I was doing most of the work and the only time he contributed was after my orgasms he would flip me over and fuck me until he reached his orgasm.

I was spasming the minute Stephen went deep inside of me and he made sure I orgasmed repeatedly before he even thought about his pleasures. He loved playing with my clit and especially loved when I soaked him with my abundant squirts. He also wasn't shy about going down on me, a totally different feeling than having a woman at my pussy. It was when he took me doggy style, however, that I was thrown into a bliss I'd never felt before. I loved him thrusting his hard cock into me and even liked when he played with my ass, something I'd never experienced before. The moment he slipped a finger into my tight little virgin anal hole I felt my pussy tighten around his cock and a moment later I let out a loud groan and came hard against him, setting him off into an earth-shattering orgasm. Stephen took what was I thought was good sex with Nancy, David and Booty Call Group, to fantastic no holds barred sex and I loved every minute of it.

I knew the moment I felt Stephen's touch there was something special between us. It was a unique first night together. Not only was the sex we shared the best we'd ever had but we spent hours talking and telling each other about our lives. Early the next morning, when most people were getting ready to go to sleep Stephen and I slipped out to the backyard and with only a large comforter wrapped around us watched the sunrise.

"May I tell you a secret," he said in a low voice almost like he was afraid someone might overhear us.

"I hope you will always tell me your secrets."

He drew his arms tighter around me. "When I normally come to these parties, which isn't very often, it's always been mainly to get me some man-sex. You are the first woman from the group I've ever been with."

"Mmmm...and such a beautiful first it's been." He was hard again and I didn't hesitate for a second to move to his lap and take his thickness in me again. "The same holds true for me. I've only been with women at these gatherings."

"When can I see you again." He asked kissing me lightly down my neck until he got to my breasts.

"Is tonight soon enough?"

"It is...but it still seems like an eternity..."

I never slept with David again and five years later, Stephen has been the only man I've desired. My relationship with Nancy continued on and off for another year until she and David became involved with a bisexual couple and they decided to move to Palm Springs full time to try a polyamorous relationship. Stephen always let me know when he received emails from David. The two couples are deliriously happy and have dropped out of the group sex scene altogether and were getting ready to make a permanent life commitment to each other.

Stephen and I never went back to the Booty Call Group. We have called an occasional woman from the group here and there, but for the most part, Stephen has been my 'go-to'. The reverse held true for him too. He and David enjoyed each other's company until he moved away, but since then I've been his primary woman, with an occasional three-way throw in every now and then. To satisfy his bi-sexual needs, he's never had to go any further than my roommate Thomas' bed. The two of them, from the moment they met, was that perfect yin/yang coming together of souls.


Evelyn was a goddess, all six feet three inches of her. I had a particular fondness for large breasted women, especially when their nipples were overly sensitive and loved to be chewed on for hours on end. Nancy had a decent chest but they weren't all natural and her nipples weren't overly sensitive. I acquired my love of large breasted women from Maureen, one of Nancy's best friends. Maureen, had a scrumptious set of natural breasts with long thick nipples that when sucked had her pussy dripping like a broken faucet, something that Nancy also lacked and became a delicacy for me.

Intuitively I knew, or at least imagined, Evelyn's nipples were going to be so sensitive I could bring her to orgasm just sucking on them. They were straining against her white silk blouse and had me licking my lips uncontrollably wanting to taste them. My eyes went from her breasts, back up to her lovely face and back to her breasts again. There was no way I was going to be shy or coy about my desire for this magnificent woman.

It would have been easy to say I'd been horny all day but the truth was, I was always horny when it came to women. Don't get me wrong, Stephen filled my needs wonderfully, there was just a part of me that felt more satisfied when I was with a woman.

Between school and Thomas and I traveling so much it had been a while since I'd taken the time to relax with a woman in my bed. For weeks Stephen and I talked about calling Maureen for a three-way, but we just hadn't gotten around to it. Now my only thoughts were of the stunning beauty standing opposite of me hoping she would open to the womanly pleasures I could give her. I was immediately wet thinking of different sexual scenarios involving the two of us...and yes, I even allowed one errant thought go to a three-way with Stephen.

"But I'm sure we had an appointment today." She bemoaned while she pulled her day-planner from her expensive leather briefcase. She was a seasoned pro at the pharmaceutical game, keeping up the farce even if it was starting to move past its expiration date.

"I'm truly sorry. You must have gotten your days confused. Dr. Westminster doesn't have office hours today, he teaches at the University on Tuesdays and Thursdays." I smiled sweetly and licked my tongue over my top lip. Evelyn's eyes were glued to me, giving me hope she was just as enticed with me as I with her. I was more than ready to pounce, all I needed was any type of indication she was interested.

I stood to go through the motions of showing her out, yes and to let her see my total package, which today was dressed in an above the knee grey pencil skirt and a fitted white shirt that showed off my ample breasts and cleavage. I had no intention or desire for her to leave but was gathering if we had any chance of getting together I would need to make the first move. I felt like we were already half-way into the dance even though we'd only met minutes ago. I stood next to her, and even in my heels, felt overshadowed by her towering height, and breathed in her clean, feminine and lightly perfumed essence.

"And you are?"

Oh, thank goodness, she engaged me in conversation! She didn't want to run off.

"I'm Dr. Westminster's intern. I watch over his domain when he's not here." I smiled halfheartedly, even if it was only for twelve more days.

"Ahhh...his protector so to speak," Evelyn said smiling.

Yeah, you are correct about that...he's my lover also.

Her eyes fluttered briefly and for the briefest second, I noticed she too was taking deep breaths and I prayed she was doing the mating dance with me as well. Whatever she smelled or felt or did, her entire demeanor changed in a blink of an eye. She was no longer agitated and appeared more than content to remain in close proximately.

"Would it be too much to ask for a glass of water? I've been on the run for hours."

I didn't give a flying fig what stall tactic she'd chosen to use on me, I wanted this woman and hoped she was feeling the same about me.

"Not at all. Please come this way." I took a moment to lock the office door before we retreated to the breakroom, with its comfortable sofa, in the back portion of the office.

"I appreciate this," Evelyn said drinking deeply from the chilled bottle of water. "I've been doing pharmaceutical sales for over ten years but only recently transferred to San Francisco. I still can't judge how long it takes to get from place to place." She was still holding out hope I was going to believe she had an appointment with Stephen and was late for it.

"Where were you before here?" I asked more than happy to engage this beautiful woman in conversation. Socializing then sex...

We were sitting on the small sofa, our bodies turned to each other. I had crossed my legs, letting my skirt ride up a little. Evelyn was dressed in a confining pantsuit that was keeping her body hidden from me. Like hers, my nipples were straining against my tight blouse. Every part of my body was engaged in letting her know I wanted her. I was in my positive thinking mode we would end up naked and enjoying each other sooner rather than later.

"Minneapolis. Born and raised. The cold winters were taking a toll on me. On a whim, I posted for this job and somehow, I got it. I was more than willing to trade the snow for rain. I've only been in the Bay area three weeks." She looked around, taking in the relaxing, minimalist décor of the small room. Stephen sublet the space and the previous tenant was into Feng shui and believed in bringing harmony to occupied spaces.

"Our company philosophy is hit the ground running. They gave me the list of drugs I need to sell along with a disorganized list of doctors. Apparently, the person who had this position before me wasn't a great record keeper. I spend most of my time researching the doctors on the list. Either they aren't the type of doctor they are supposed to be or their office isn't located where the printout says it is. It's been the most frustrating three weeks I've ever had."

"Or they no longer see patients and don't require pharmaceuticals," I added with a smile. She looked at me oddly. This truly was news to her. There wasn't a sale to be made here, no matter what tactic she tried.

I was being hypnotized with her rhythmic breathing watching her large breasts swell each time she took a measured breath. I wanted so badly to feel her skin against mine.

"It's things like that, that make my blood boil." Her exasperation was written all over her lovely face. "There are days I feel like I'm being set up to fail." Tears filled her eyes, "In Minnesota the job was moderately stressful, having to make your quotas every quarter but here seems impossible," she took several deep breaths to squelch her tears, "plus to make matters worse, I can't find a place to live. It's so damn expensive here, I can barely afford to eat, let alone find anything but a closet to live in. The company gave me thirty days in a residence type hotel...and to prove I can handle the territory. I only have one more week left before I have to foot the bill myself if I don't find a place to live."

My next words fell out of my mouth with no hesitation whatsoever.

"I know this is going to sound strange...especially because we just met moments ago...but if you don't mind going into a roommate situation, I have an extra room at my house, it's in a nice suburban neighborhood and centrally located. It's a large house and you could have all the privacy you need. The only caveat to that is it's only available for the next six to seven months. It would give you plenty of time to find a place with no stress."

"That's very sweet of you to offer..." Her voice drifted and for the first time, we both realized I'd never told her my name.


"Oh, what a beautiful name, it fits you perfectly...an angel sent from heaven." Evelyn smiled and in that moment, I knew she felt the exact same way I was feeling.

"So, does that mean you are interested?"

"I would like to see it. I'd love to be out of the hotel, but I also don't want to take something where I might not be happy." A moment later she leaned her body just a titch closer to me and took a deep breath.

Oh baby, I'll make sure you are happy...twenty-four hours a day, seven days a week in my king-size bed that has a spot reserved just for you.

My house had five bedrooms but in my mind I was already rearranging my extra-large walk-in closet and made room for her in my dresser. My bathroom wouldn't be a problem, it had a His and Hers (or Hers and Hers) separate sinks, with more than enough room for both of us.

"If you'd like to see the place you can follow me when I leave...it's close to here...the only problem is I can't leave here until five if you don't mind waiting."

I didn't want to wait another hour and a half to have her. If Stephen wasn't in class I would call him and tell him I was leaving. The more I was with her the more my desire for her grew. I was being irresistibly drawn to this magnificent woman.

"I don't mind at all." There seemed to be an unspoken: 'There is no place I need to be other than right here with you' in her voice.

Normally, in my women-on-women flirtations, I customarily preferred the woman to be the seducer. It didn't mean I was submissive, far from it. It was just part of my narcissistic nature. I enjoyed having my pleasures met first before I played.

Evelyn, however, was the exquisite exception. I was more than willing to put my sexual satisfaction on the back burner to please this alluring woman. I wanted so badly to strip her top off and bury my face in her lovely globes that were sitting so high on her chest and silently calling out to me.

My eyes moved from her enchanting face down to her breasts. Evelyn followed my eyes and without warning let out a loud gasp, grabbed her suit jacket and pulled it tightly closed around her chest.

"I'm so sorry," she gulped fighting back some kind of unrecognizable emotion.

At first, I thought I'd offended her by being so overt, but the more I looked at her it appeared to be something else. Jumping up from the couch she pulled her jacket as tightly as she could over her breasts and moved to a corner facing away from me.

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