Pleasure Point: The Complete Series

by Evans, Jennifer

  Then there was Cassandra who liked me to wear an Armani raw silk suit with a red tie, meet her in the fine dining room of the Ritz, and enjoy expensive caviar and Dom Perignon champagne. From there, we’d steal away to her suite, where I’d remove that silk suit for some A-game hot sex. One time, when we were in the dining room, she removed a small battery operated remote control from her silver evening bag and handed it to me. Every time I pushed the button, it activated a vibrator implanted in her panties. Once I managed to make her come just as the white-coated waiter served our chocolate mousse for dessert. It was pretty funny to watch her try to hide her orgasm from him. Both of us had burst out laughing when the waiter walked away.

  There was Kimberly who liked to have sex in public. Once, she had me cover my body with fake tattoos, wear torn jeans and a black leather jacket, pick up a Harley Davidson that she had already paid for, and meet her at the Ritz where I sped away with her on the back, her feminine arms around me. She instructed me to drive to the beach just past San O where we parked on the cliffs overlooking the ocean at sunset. She lifted up her black leather miniskirt, and had me pull down her lace panties. Then she bent over the leather seat of the motorcycle while I slid into her as the sun set, and the surfers leaving the ocean strolled on the beach below.

  Jenna was a racy redhead who liked to meet me at the beach where I would be waiting with two stand up paddle boards. We would paddle out into the ocean where she instructed me to strip down while she did the same. It’s not that easy to have sex on a paddle board, but we did manage to have Jenna lie very still on her back with her legs spread while I kissed, licked, and sucked her to orgasm.

  Sandy must’ve had a special deal with the management at the Ritz-Carlton, I don’t know. I do know that I got to spend plenty of time there, which was fine with me because I quickly got into a routine of running on the bike path that stretched for several miles behind the resort, then did weight training, then surfed, and then took care of my very happy clients.

  Much as I’d resisted it, I’d found my niche working for Sandy. Servicing Sandy and her forty-something-year-old friends was like slipping back in time and making love to Rosalyn again. I was only eighteen when Rosalyn and I began our affair, and since she was the older one with all the experience, she taught me everything I knew about sex. I loved pleasuring Rosalyn with my body and her vast collection of sex toys. The things I learned from Rosalyn had come in handy with the sexy women I’d had the good fortune of making love to over the years, and being with this group of experienced women allowed me to recreate what it was like pleasuring Rosalyn.

  If I couldn’t have Rosalyn, well, at least I had my Janes and Holly.

  Word somehow spread throughout Sandy’s community, and I became quite popular.

  My clients ate me up.

  And then there was Olivia.

  The first time I met Olivia, she wore a red-and-black, plaid miniskirt, a crisp white, short-sleeved, button-down shirt, a pair of white knee high socks and black loafers.

  Olivia was the youngest of my clients, probably closer to my age than Sandy and her forty-something group. When I knocked on the door and she let me in, I immediately sensed her nervousness.

  “You must be Olivia,” I said. “Sandy didn’t tell me you were so pretty.” I gently touched her arm. “Want to go on the balcony and check out the surf?”

  She peered up at me through black bangs that hid her large brown eyes. “Okay.”

  It was my job to put her at ease. We walked outside and breathed the ocean air.

  “Would it be okay if I kissed you?” I asked. She barely made eye contact with me, but she said that I could kiss her. I tenderly kissed her mouth and stroked her silky dark hair then unbuttoned her blouse. Olivia had a tattoo on her upper chest, which spanned collarbone to collarbone, bearing the inscription, Forgive Me Father. We kissed for a few more minutes, and I slowly removed her blouse. On her inner waist was another tattoo with line after line of writing. It was the Serenity Prayer from Alcoholics Anonymous.

  Olivia’s heart felt like a hummingbird’s. Her palms were sweaty. “Why don’t we go inside?” I said. I stroked her face with a feather-soft touch, gazing into her exotic eyes. “You can relax with me. This is what I do.”

  When we moved inside, Olivia shyly reached into her handbag and removed a silver chain. It had a nipple clamp that looked like a roach clip on each end. Her large brown eyes wouldn’t meet mine, and I detected a hint of tears. “What is it you want, sweetheart?” I asked. “It’s okay, you can tell me.” I spoke in a soothing tone while gently stroking her arm. I could see relief flood through her as she realized I wasn’t going to judge her.

  It turned out that what Olivia wanted was for me to secure the nipple clamps on her cherry red nipples and slowly work a glass dildo in and out of her while massaging her sweet spot with my thumb. When she was ready to come, she wanted me to yank on the chain with my teeth. Her fingers dug into my hair as she arched her back, her head thrown back, her long dark hair a curtain.

  Then she wanted me to put her over my lap and tell her that she was a very bad girl while I spanked her. “Am I a bad girl, Jax?” she would murmur.

  “Yes, Olivia, you’re a very bad girl, and I have to do this,” I would say as my hand came down for another blow.

  “Are you going to spank me harder?” she’d ask.

  “Yes, Olivia, you’ve been bad again. I told you it would come to this, but you never listen, do you?”

  Olivia could actually orgasm just from me spanking her. Our session would end with her curled up on my lap, me kissing her face softly. “It’s okay now, baby. You try to be a good girl until next time.”

  Olivia was so sweet and vulnerable. She needed protecting and quickly became my favorite client.

  * * *

  All my clients loved me. If you were a female who had a thousand bucks cash, you could have a session with me, orgasms guaranteed. This new sideline funded not only my monthly expenses for rent, utilities, and food, but allowed me to travel to surf all the big wave spots without having to wait for sponsors to sanction the trip in the name of a photo shoot or contest. When the waves were good, I could pick up and, surfboard bags in hand, head out to the airport for any destination I wanted.

  My clients needed me, and I was happy to take care of them. This may sound odd, but I loved those women. They were trusting and loving, and I was providing something that they had been unable to find in their lives for various reasons. Some had husbands who were cheating on them; one was married to a man that had a secret stash with photos of him wearing a dress. Olivia had married the wrong man, was divorced with a hefty financial settlement, and was discontent with the BDSM scene. Or maybe she had read too many of those Fifty Shades of Grey books.

  Those women became my family.

  It was the first time in a long time I’d felt truly needed.

  And then there was Holly. She provided a calm in my life in the form of friendship, romance, and the stability of a girlfriend. In my more lucid moments, I was terrified that she was going to find out about my secret life because I had grown to care about her, but I reasoned, I didn’t have a ring on my finger. She never questioned how I earned my keep.

  Once I had enough money, I planned to quit. I tried to convince myself of this while I shopped for toys at the wholesale sex warehouse in downtown San Diego. Their clever slogan was Your Pleasure is Our Business. I even played around with the idea of making calling cards that said, “Your pleasure is my business” on one side, but I knew I didn’t want to be in that line of work forever. Calling cards were a commitment I wasn’t ready to make. On that shopping trip, I purchased special nipple clamps for Olivia. At the time, I thought nothing of it. They were just a gift for a friend.

  Holly

  The rest of the Mystic Seaweed reps and I were at our annual sales meeting. I would’ve much rather been out in the field selling, but the fact that the meeting was held at the Ritz-Carlton was a small consolation.
At least the lunch they provided was exceedingly better than the dried up sandwiches and stale cookies we were served during our meetings at the office. My eyes glazed over, and I felt the beginnings of a headache as I stared at the Excel spreadsheet displayed on the screen at the front of the conference room. More metrics and mind-numbing numbers to evaluate. I sighed heavily and unobtrusively inched my way to the back of the room then bolted for the restroom. Anything to get out of the sure-fire-cure-for-insomnia of a sales meeting.

  The bathroom featured marble floors, real towels instead of paper towels, and fresh flowers. I smiled in appreciation, thinking that if the bathroom was this luxurious, the rooms must be over the top. I entered one of the stalls, locked the door, and sat on the closed toilet, wasting time by checking photos of pro-surfers on Instagram. I’d been in there for a few minutes when I heard two women enter, use the facilities then wash their hands. They began talking in hushed tones.

  “He likes to wear a cock ring when he fucks me,” one of them said.

  “Remember when I told you about the nipple clamps? He even bought me a new pair,” said the other one.

  They both laughed.

  The first one said. “I told you it would work out. You’re happy? Worth every penny?”

  The second one said, “Stop. You’re making me blush.” She paused then said, “But, yes, you were right.”

  I tried to be as quiet as possible. I hopped up and pressed my ear against the door which featured slatted wood panels. Were they really talking about paying for sex?

  “And his cock,” said the first one, “I’ve never seen one so goddamn sexy. I laid my hand next to it when he was hard, and it’s got to be eight inches easily.”

  The second woman giggled nervously, and it sounded like they were winding up their conversation. I couldn’t wait to see what they looked like. I quietly exited the stall and, averting my eyes, headed straight to the sink to wash my hands. When they saw me, they both straightened, the younger one nervously toying with the zipper on her black leather bag.

  Out of the corner of my eye, I checked them out. The older one was a well-kept OC housewives type: expensive haircut, skinny jeans with a jeweled top, overpriced designer bag, lips that were tastefully plumped up by silicone. She hurriedly applied lipstick while not making eye contact with me. The younger one looked like a super-model version of Wednesday Addams; tall, slender, sleek black hair, large brown eyes, and what the hell? White blouse, plaid skirt and knee socks? Okay fine, to each his own. Where was her lunch box? I chuckled to myself then got the hell out of there.

  Back at my seat in the conference room, my mind wandered to Jax. Not that my thoughts were ever far away from the man. I was more than a bit concerned that he had lost his Mystic Seaweed sponsorship because I knew how men were about money. It seemed silly to me, but I guess with no dragons to slay, or animals to hunt and drag into the cave for their women, money had become our culture’s equivalent of how men proved themselves worthy to women.

  But Jax didn’t wallow in self-pity or seem overly concerned about money. In fact, he seemed content and happy. We’d been dating for about three months and he spent his days at the Mysto Spot Surf Shop where he gave surf lessons, and he was able to travel to surf big waves. He’d alluded to the fact that he had an inheritance from his brother’s death, but I didn’t press the point. If he wanted to talk about money, or Tyler, I would let him bring it up.

  Thankfully, the sales meeting ended early. Jax and I had planned to get together that evening. Jax and I had fallen into a pleasant routine of working out together, eating dinner together, walking the beach, watching dumb movies on Netflix, and having loads of hot sex. I was always excited to finish up my workday in anticipation of feeling his warmth inside me. He had texted me during the meeting saying, “Let’s stop by the Mysto Spot Surf Shop before we go surfing. I want to introduce you to Butch.” Since Butch was his best friend, I thought it was a big step in the right direction.

  Wanting to impress Jax’s best friend, I went into the restroom at the Ritz, freshened up my makeup and hair then sped off to Encinitas in my BMW.

  We met in front of Jax’s apartment and walked to the shop together.

  “Hey! Come on in,” Butch said. He stood up from his post behind the counter, and I saw his peg-leg. I was surprised that he didn’t walk with a limp. He was built similarly to Jax—broad shoulders, an erect stance, sun-bleached, tousled blond hair. He caught me staring at his leg. “Like it? Artwork was done by a local tattoo artist.” The leg was decorated in vibrant shades of turquoise and orange, depicting an ocean scene with perfect waves and a sunset.

  “Um, yeah, it’s cool.”

  He opened his arms to give me a hug. He was just as powerful as he looked. “You don’t want to hear about my leg. It’s great to finally meet you. But Jax didn’t tell me you were so good looking.”

  I glanced at Jax, and he smiled.

  “You surf big waves?” I asked. And there I went again with that stupid nervous habit of mine. I twisted a few strands of my hair and pulled.

  “Yep. Jax and I met way back when I’d first moved to Point Loma. Guess I was about eighteen.”

  I pulled my hair again. Jax squeezed my hand.

  “And then,” he continued, “we started taking trips down to Mexico for the bigger waves.”

  Jax said, “Butch out-surfs most of the guys with two good legs.”

  “Don’t know if I’ll ever be as good as you,” Butch said.

  “You’ll be better. You’ve got more legs than surfboards. It’s not fair.”

  Butch said, “Jax said you work for Mystic Seaweed?”

  “Yes.”

  “So, how come I’ve never heard from you?”

  I twirled and pulled another handful of hair. “I think you get to talk to Eva.”

  “Oh yeah, Eva. Guess they give you guys different accounts.”

  “Something like that.”

  We talked for a while longer about the surf, my job, how great the waves were at Swami’s that day.

  “Glad to see my man finally got himself somebody cool like you,” Butch said. “He needs somebody to calm him down. Don’t be a stranger.” He waved, and Jax and I walked, hand in hand, into the bright California sun.

  “Do you think he liked me?” I said.

  Jax turned to face me, his eyes sparkling on that perfect Encinitas day. “Honey, he loved you.”

  After that, we waxed up our surfboards, or should I say, Jax waxed both boards because he would never let me lift a finger. We surfed the perfect, glassy waves at Swami’s then went back to his apartment.

  We stumbled, happy and laughing, into his place. Jax peeled off my wetsuit then his, and we collapsed on his bed, our bodies covered with a fine layer of dried salt water. Jax held my hand and kissed it. “How was work today?”

  “Boring.”

  “Really? I thought you liked your job.”

  “I do, but today we had our annual sales meeting. At least it was at the Ritz-Carlton instead of the conference room at work.”

  Jax cleared his throat. “The Ritz! Oh yeah. That place looks nice.” His hand squeezed mine. “You mean the one in Dana Point?”

  “Yep. Luckily we only have those meetings once a year.”

  Jax stared at me, and I fell into the intensity of his mesmerizing eyes. One hand moved to my cheek, and he gently stroked then kissed me softly. “You taste like the ocean.” Then he sat up and said, “Hey, you want to try something out?” He hopped up out of bed like a little kid excited about Christmas morning and pulled open the third drawer of his dresser. I looked over his shoulder and saw a collection of more than a few sex toys. I was intrigued, always ready for something new.

  We leaned against the cushy pillows, the open window allowing the cool ocean air to caress our naked bodies. We sat in bed, reading the claims on the package of the Mini Nipple Suckers. The package contained two hot pink plastic devices that looked like thimbles. Heightens Sensitivity! Super Suction!
Soft and Pliable!

  “Let’s try it out,” I said.

  He ripped open the package, licked the inside of the Mini Nipple Suckers like an expert and applied them to my eager nipples. The sensation was immediate and arousing. Those things pulled and tugged at my nipples, engorging them with blood; my pelvis contracted in response. Jax spread my legs and gave me his patent pending oral sex until I screamed.

  And that’s the way it was with Jax. He knew how to surprise and delight me, and he treated me like a goddess. The man knew how to make me feel like I was the only woman in the universe.

  I had met my match. I was in love.

  Jax

  Butch and I were playing darts and throwing back a few brewskis at the Leucadian Pour House one night, a sports bar in the town next to Encinitas. The Pour House was a real local’s hangout with a surfer theme. There was a huge mural on one wall with a spectacular painting of the ocean with vibrant blues, purples, and oranges. And they had some pretty damn good spicy chicken wings and microbrew.

  I was creaming Butch at the dartboard and feeling mellow. Life was good. I had been surfing better than I’d ever surfed, I was having a great time hanging out with Holly, and I was making bank. A little joke that I’d been dying to tell anyone that would listen, but I couldn’t was, “I’m in a stable relationship. I have a stable of women.” When we were done playing darts, we sat at a table and ordered mugs of beer.

  “Why do you keep checking your phone, dude?” Butch said.

  My phone lit up with a text from Jenna. Hey stud, when are we going out on the paddle boards again? I get wet every time I think about it. Butch leaned over and read the text.

  He snorted with laughter, his hand covering his mouth full of beer. “Who’s Jenna?”