Judge Not
by GinaB33
Copyright© 2019 by GinaB33
Romantic Sex Story: Young woman enters into a unique relationship with her doctor boss.
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual BiSexual Heterosexual Fiction Sharing Analingus Cream Pie Exhibitionism Oral Sex .
It was a beautiful day, and I was enjoying a leisurely swim in our pool. I glanced at the clock on the wall of the pool house. It was almost two p.m., so I decided to go upstairs to check on Darren, my husband of two months.
After drying my naked body, I made my way to the wet bar in the den. I mixed a Jack and Coke and a mild Screwdriver. When I got upstairs to our bedroom, I was somewhat surprised to find our bed empty, so I peeked into the bathroom. The shower was running, and I could hear giggles over the sound of the water.
I walked closer and said, “I brought you fresh drinks.”
Darren called back, “Just put them on the bedside table, please.”
“Thank you, Gail.” Linda called out.
Two minutes later, I was once again in the backyard and soaking up the warm sun.
I was somewhat disappointed. I would have preferred to walk in on them while they were fucking or engaged in some other hot sexual activity. I would have loved to watch for awhile. “Oh well.” I sighed, “Later perhaps. We have all weekend.”
A year and a half earlier, I showed up for my first day of work as a licensed Marriage Counselor in Dr. Darren Wilshire’s office. His last words to me before I saw my first couple were, “Remember...”
I cut him off, “Money or Sex.” I said with a wide grin I hoped would disguise my nervousness.
“Find out which one it is, and let that dictate how you proceed.” He told me with an encouraging pat on my back. “You’ll be fine.”
When Mr. and Mrs. Gibson were seated in my new office, I could see how uncomfortable they were. They were a middle-aged couple, fairly affluent, and I sensed that my age was a problem. I was twenty-seven.
“Before we get started, I feel we should clear the air. First, I understand that you are here under court order prior to your divorce being advanced.” When they both nodded, I continued, “Just so you know, you are my first ‘official’ clients. I understand that my age and lack of experience may give you pause, but Dr. Wilshire has complete confidence in me. I hope you will reserve judgment on that until after this first meeting. Then, should you decide you’d prefer someone older and more experienced, I will completely understand, and I’ll even help you with the arrangements.”
And with that, my chosen career was underway.
Dr. Wilshire had a very successful and growing practice, despite his being only thirty-one. He had some advantages going in though. He came from a very wealthy family, so finances weren’t a problem when it came to setting up his new practice. His name didn’t hurt either. His father was a very prominent psychologist in the city, so he got plenty of referrals to get his practice off the ground quickly.
That worked out well for me too. I was the first Counselor he’d taken in. He was relieved that he was finally able to stop turning potential clients away.
Every day, after our last appointments, I would sit in Dr. Wilshire’s office, and we’d review my notes on the patients I’d seen that day. During one such meeting, he read my notes about an earlier session. A middle-aged wife had complained that her husband didn’t pay enough attention to her sexually. I’d already seen her husband separately and listened to his complaints. I told her, “He’s not seventeen anymore, and you’ve been married a long time. You need to start seducing him, dress sexy, act sexy, whatever it takes to get him in the mood ... you need to start that long before bedtime.”
When she asked me, “Why’s that my job instead of his?” I told her, “Because you have the tits.”
Dr Wilshire sat back in his chair, intertwined his fingers across his chest and said, “Please tell me you didn’t really say that to her.”
“I did.” I answered him with a giggle.
Dr Wilshire just shook his head and started laughing. He didn’t stop for over a minute.
“My, my, Miss English. If I didn’t know better, I’d think you’re trying to seduce me.” Dr. Wilshire chuckled when I showed up at the restaurant for supper on my birthday.
I was wearing a skirt that hit me just above my knees, a thin tank top with a light bra, and small scarf. The tank top was cut low enough to show a little cleavage, but not blatantly so. Of course, he’d never seen me in other than work clothes.
In truth, being around him turned me on greatly. I’d had a crush on him since long before he’d hired me. Now, after months of working in his office, it was driving me insane.
“Would that be a bad thing?” I teased him.
“Not if you want to get fired.” He shot back, but with a wide grin on his face that told me he was kidding.
“Oh my, Doctor, does that mean you’re afraid you can’t compartmentalize work from pleasure?”
He stared me hard in the eyes, but before he could answer, they called us to our table. “Saved by the bell.” I teased him again.
After we were seated and our drinks ordered, he looked right at me with a raised eyebrow and said, “I can.”
His comment and expression made his meaning clear. He was concerned that I couldn’t. I nodded and smiled at him. “I’m great at compartmentalizing.”
The following Friday, after our post appointment meeting, I was just about to leave his office when he asked me, “Do you have dinner plans?”
I considered my words carefully before answering. “No, in fact, I don’t have any plans at all ... for tonight ... or in the morning.”
After letting my meaning soak in, he smiled, “Do you like Chinese?”
“Very much.” I beamed a smile back at him.
“I make a wonderful Hunan Shrimp with Shrimp Fried Rice.”
“Very nice. I love that, but how are you with breakfast?” I asked boldly.
“If you want more than coffee and a bagel, you’ll have to bring something and do the cooking.”
I walked to his desk and held out my hand, “Your address?”
When he scribbled it down and handed me the slip of paper, I turned and walked out of his office, calling to him over my shoulder, “I’ll bring something for breakfast. See you at eight.”
When I arrived at Darren’s home, I was blown away. It was obvious he wasn’t paying for a place like that on his earnings from the clinic. It was huge, with a long drive that ran between two rows of tall pines. The drive ended into a wide circle around a beautiful fountain.
“No maid?” I asked him when he answered the door himself.
He stared at me hard and then smiled, “Her quarters are in the back. I gave her the night off.”
“Then you’ll have to put these away yourself.” I said in a flippant tone as I handed him the plastic grocery bag. And then I strode by him to see the inside of the house.
“Hang on. I’ll give you the nickel tour.” He called after me.
“Aren’t you supposed to be cooking? I have your cell number. I’ll call you if I get lost.”
I could still hear him laughing as he made his way into the kitchen.
Even after making my way up the large winding staircase, it took me a while to locate the palatial master bedroom. Once there, I glanced into the bathroom before heading out onto the balcony. It didn’t come as any surprise when I found myself looking over acres of groomed lawn, an Olympic-size swimming pool with a fountain in the middle, and a nice hot tub near the pool house. And yes, there was a separate maid’s quarters to one side of the house.
“You’re way overcharging our patients.” I teased Darren when I finally went back downstairs and found the kitchen.
He sloughed off my comment. “Family money. Sorry, I should have warned you.”
“No, you wanted it to be a surprise. You were hoping I’d get all weak-kneed and it’d be easier for you to get into my pants.”
“Busted!” He said with a wide grin. “I was worried you might play hard to get.”
It was obvious he didn’t need the paltry sum he got from the clinic. “Seriously though, you must really love your work.”
He glanced around at me and smiled, “I do, very much.”
Supper was wonderful. He wasn’t kidding about his cooking skills. “You’ll make someone a great wife one of these days.” I teased him.
I helped him clear the table, rinse the dishes and load them into the dishwasher. “I don’t like leaving her a mess.” He explained.
I was impressed.
“Jack and Coke?” He asked me.
“Oh, so now you’re going to try to get me drunk, huh?”
“Only if I have to.” He replied with a smile.
“You don’t.” I said as I stepped up and gave him a warm kiss on the lips, “But put it in something plastic. I’m heading to the pool.”
“Did you bring a suit?” He grinned.
“Do I need one?”
“Not on my account.”
When he followed me instead of heading to the wet bar in the den, I teased him, “Aren’t you forgetting the drinks?”
He chuckled, “The plastic glasses are at the bar in the pool house.”
I laughed, “Of course there’s a bar in the pool house. Every pool house that’s worth anything has a fully stocked bar.”
While Darren was making our drinks, I began undressing. “Don’t look.” I called to him with a giggle.
“Yeah, right! Now you’re being delusional.”
“Is that your professional diagnosis, Doctor?” I teased as I stepped out of my panties. I didn’t wait for his answer. Instead, I just walked the few steps to the pool and jumped in.
The water felt wonderful on my naked body. I hadn’t been skinny dipping since I was thirteen in our uncle’s farm pond with my brothers.
After setting our drinks on the edge of the pool, Daren began undressing and placing his clothes neatly on a lounge chair. I made a mental note, first the dishes and then the way he folded his clothes. He wasn’t accustomed to being pampered, but rather, he was used to taking care of himself. I was a little embarrassed that I’d just thrown my clothes haphazardly onto a chair.
When he was finished undressing, I was on his side of the large pool, sipping my drink. He walked right up to me and said, “Hey, you’re looking.”
“Like you didn’t?” I teased.
And then he dove over my head and into the water. A few seconds later, he surfaced beside me and reached for his drink. “You know.” He said, “By this time, I’ve usually at least gotten a good kiss.”
I turned and looked at him, drink in hand. After taking another sip, I asked him, “Oh, does the good doctor want me to be like all the other bimbos he entertains out here?”
“There hasn’t been that many, you know—not nearly as many as you might think.” He told me in a serious tone.
I raised an eyebrow, “Oh, and what happened to them?”
He shrugged, “Mostly, once they see this place, they start hearing wedding bells and dreaming of living a life of luxury.”
“Can you blame them?” I asked.
“No, but I want more than that.”
“Oh, please, do tell. I’m serious. I’d really like to know.” I told him in a serious tone.
“Sex or money, remember?”
“Well, it appears that you have the money part covered, so what was it about the sex?”
“Do you really want to know?” He asked me skeptically.
“Yes, I really do.”
“So far, I haven’t found one that can separate sex from fun—the physical from the emotional. That’s about it.”
I looked him straight in the eyes without blinking, “Darren, I’ve told you before, I’m great at compartmentalizing.”
He didn’t break our eye contact, “Be careful, Gail, I might just fall in love with you.”
I laughed out loud, set my drink on the side of the pool, and pushed off with my feet. “You don’t even know if I’m any good in the sack ... yet.”
He swam after me and caught me in deeper water. He struggled to keep himself and me above water when he put his hands on my waist. “If the way this evening has started is any indication, I’m sure that’s not going to be a problem.”
I put my arms around his neck and helped him dog paddle as best I could. “I do have a serious question for you.”
He seemed to sense that I was going to tease him some more. “Okay, shoot.”
“Does the pool house have bathrooms, or do I have to dry off and go into the house?”
He chuckled, “It just so happens, it does.”
“Silly me, of course it does.” I giggled, and then I gave him another warm kiss on the lips. When I pulled away from him and swam over to the steps, I called over my shoulder, “Don’t look.”
“You’re still delusional.” He called after me.
When I came out of the pool house, Darren was sitting on the side of the pool sipping his drink. I walked over to him and spread my arms out from my sides, “Okay, I guess you can look now.”
He took full advantage of my offering, his eyes slowly making their way over my body. He seemed pleased, as well he should have been. I knew I still had the body of a girl younger than my twenty-eight years. My thirty-six C cup breasts were full and perky, my tummy flat, and my legs long and toned. I kept my pussy trimmed very tightly.
Finally, he looked up at my face, “Very, very nice. Thank you.”
I sat beside him and took up my drink. “So, did I pass your inspection?”
He let out a loud laugh, “Oh, so now you’re gonna fish for compliments, huh?”
I giggled, “Of course. Now get with the program.”
He turned to me and pulled my chin around with his fingers. Looking deep into my eyes, he said, “Gail, I love the whole package, but I love this the most.” He said, tapping his finger on my temple.
God! I really, really, really wanted to fuck him right then. “Oh?” I tried to maintain my composure, “Anything in particular?”
He smiled, “On your birthday, the way you teased, the way you let me know you were interested. And then today in my office, how bold you were. And even when you got here, you weren’t overwhelmed, right up to this minute. You’re just different, and I love it.”
“Hell, it’s just sex, Darren, remember? I’ve just been jacking off your largest erogenous zone.”
He laughed, “And you’re damn good at it.”
“I’m going to need a shower to wash off the chlorine.” I told Darren.
“I’ll join you.” He said, helping me to my feet.
I put my hand on his chest to stop him, and after leaning in to give him another warm kiss on his lips, I said, “No. I don’t want that. I want time to wash and dry my hair and get myself ready for you. I trust this place won’t run out of hot water. If you don’t mind, take your shower in one of the other bathrooms. You’ve only got like a half a dozen to choose from. I’ll call your cell when I’m ready. Okay?”
“Whatever you want.” He responded with a smile.
“I would appreciate having a fresh drink waiting for me when I get out of the shower, though.”
And then he pulled me in for another warm kiss. To his credit, he didn’t try to make it a passionate kiss. He seemed to understand that I wanted to keep things light-hearted.
The shower in the master bathroom was incredible. It was large enough for several people, and it had half a dozen adjustable shower heads on three sides and at different heights.
There was a choice of several soaps and shampoos. I found a scent I liked and took my time washing and conditioning my hair.
When I got out of the shower, I dried myself in front of the large concave mirrors, and then my hair. I took a sip of the drink that was waiting on the counter for me, and reflected on how sexy the whole setting made me feel. And too, knowing that Darren was somewhere in the house, that he was waiting patiently to have sex with me, made my whole body tingle.
“Hello, is this Dr. Wilshire?” I asked into the phone.
“Yes,” He answered.
“Your next patient is waiting for you in your office, and she needs some major therapy.”
“I’ll be right in to give her the full shrink treatment.”
When Darren appeared in the master bedroom, I was lying naked on his bed, propped up on one elbow facing the door and sipping my drink. He was wearing a very nice bath robe, and he had a tray in his hand.
He sat the tray in the middle of the bed, and leisurely doffed his robe, folding it neatly and placing it on a nearby dressing chair. And then he crawled onto the bed on the other side of the tray and propped himself up on an elbow facing me.
“Strawberry?” He asked me as he took one from the bowl on the tray and held it to my lips.
I took a bite, and while I was chewing it, he asked me, “So, just how do you see this evening going?” And then he put the other half of the strawberry into his mouth.
I managed to suppress a laugh. He knew exactly what he was doing. He was teeing up the teasing ball for me to take a swing at.
“Hum...” I pondered as I reached over and extracted another strawberry from the bowl. I bit off half, and then put the other half to his lips. “Well, the way I see it, unless you’re gay—you’re not gay, are you?”
He chuckled and showed me a wide grin. He seemed delighted that I understood his question for what it was. “No, not gay.”
“Okay then, if you’re not gay, and if you didn’t beat off in the shower a few minutes ago—you didn’t, did you?”
“I thought about it, but no. I resisted the urge.”
“Good, now, if you’re not gay and you didn’t beat off in the shower, then you’ve got to be like really, really, insanely horny for me right now. And if I’m right about that—and I know I am—I mean, after all, what non-gay male wouldn’t be, then you’re probably not going to be good for more than one minute if I let you fuck me right now.”
He chuckled again and fed me another half a strawberry, “Assuming that your diagnosis is correct, what therapy do you recommend?”
“Well, with most patients in your condition, I would recommend masturbation prior to sex, but since you’re a ‘special’ patient, I think a blowjob would be more appropriate.”
“And your long-term prognosis?”
“Oh, if we can stay awake that long, and assuming you’re not a ‘once and done’ kinda guy—you’re not one of those, are you?”
“Uh, no, not one of those.” He said with a wide grin.
I could tell he was enjoying this. “Whew! I’m happy to hear that. So, my prognosis is a very long night of incredible sex.”
“And when should we start your recommended therapy?”
“When is only half the question.” I said as I offered him another bite of strawberry.
“Oh?”
“Where is also important.” I’d seen something in his downstairs den, and I wanted to take full advantage of it.
“Where? Not here?” He asked, seemingly intrigued about what I had in mind.
“I’ll show you.” I said as I rolled off the bed and offered him my hand. When he was standing, I led him downstairs and into his den. I had him stand in the middle of the room while I mixed him a fresh drink. After handing it to him, I walked over to his humidor, took out a cigar, clipped the end, and lit it.
The look on his face was priceless as I puffed on the big cigar to make sure it was burning properly. And then I walked over and put it into his mouth. “Enjoy” I giggled as I slid down his naked body to my knees, tweaking his nipples with my fingers along the way.
Darren’s cock had been hard and twitching since he’d entered the bedroom with the strawberries, so I knew not to dive right into sucking him. I wanted this to last.
First, I examined his beautiful cock. It was slightly longer than average, and it had enough girth to make my pussy wet with anticipation. I spent at least a couple of minutes licking up and down his shaft, swirling my tongue around the head, and smiling up at him.
I could tell he was enjoying much more than what I was doing. I knew it was my thinking of doing it here, like this, me setting the stage. I can’t imagine he’d ever had a woman who understood the male brain the way I did. I’d spent many, many college hours studying it. My degree was in Psychology, but with an emphasis on the Psychology of Human Sexuality. I often suspected that’s why he’d hired me for his practice.
As I licked up and down his hard cock, I made sure to maintain as much eye contact with him as possible. The only time he looked away was when he was taking a sip of his drink or enjoying a puff of his cigar.
And then I saw it. The ashes on his cigar were getting long. I hadn’t thought of that. Knowing how neat and meticulous he was, I knew he wouldn’t want to just flick them onto the carpet. “Hang on”, I giggled. There was an ashtray on a small table between two chairs, so I slid it over close enough for him to reach.
“Thank you.” He said with a huge smile.
And then I went right back to licking up and down his cock. Finally, I took him in my mouth. Still though, I didn’t hurry to get him off. I wanted him to really enjoy it. After all, I was.
It was another five minutes or more before I felt his urgency grow. His hips began ever so slightly moving forward when I slid more of him into my mouth. This wasn’t my first time giving a blowjob. I’d given many of them, mostly to my long-term boyfriend in college, but with several other boys too, going back to my high school days.
I tightened my grip on the base of his cock and increased the tempo of my tongue flicking the underside. It didn’t take long before I felt his thighs stiffen.
That’s when I pulled my mouth off of his cock, opened my mouth wide with my tongue extended and began stroking him in earnest, pointing the head of his cock at my open mouth.
I was looking up into his eyes when his face contorted and I felt the first forceful blast of his cum hit my cheek. I forced myself to maintain eye contact with him as I continued stroking him.
He came and came, but that wasn’t a surprise. I knew he was long overdo, and I’d done a great job of teasing him for a long time. Before he was done, my cheeks, my tongue, my chin, the inside of my mouth, and even my chest and breasts were splattered with his cum. When it was time, I put his cock back into my mouth and gently milked the last drops from it.
“I’ll get you a washcloth.” He said with a big grin.
“Okay, but not yet.” I stood up and looked him in the eyes while I used my fingers to gather up as much of his cum as I could and lick them clean.
When I was finished, he pointed to a big glob of cum on one of my breasts, “You missed some.”
I giggled, “No I didn’t. C’mon, I’ll show you.” I took his cigar from him and smashed it out in the ashtray. Then I made both of us a fresh drink and led him back upstairs. Once there, I took a strawberry from the bowl, rolled it in the glob of cum on my breast, and as seductively as possible, slid it into my mouth.
The huge grin on Darren’s face was all the reward I needed. “I’ll take that washcloth now.”
I would like to be able to report that the sex that night was incredible, that we fucked for hours and both came many times, so I will, because that is the absolute truth.
First and foremost, I’ve never laughed so much during sex in my life. I teased him while he ate my pussy, and my god, could he eat pussy! He teased me while I was sucking and licking him back to hardness, and I know I can really suck cock.
Once, while sucking him, I licked a finger and ran it over his asshole. His whole body tensed, which gave me leave to tease him over and over about it. In turn, he wasn’t a bit shy about licking my ass, and I loved that. I always have.
“Oh, someone likes that.” He teased me.
“Uh huh.”
“Just a tongue, or a cock as well?” He asked me.
“A tongue, a finger, a cock, a vibe, I like it all, but a tongue is my favorite.” I told him honestly.
Another time, while he was fucking me and I’d cum so much I was gushing, he excused himself to go get a towel. When he returned and dried me up some, I giggled, “That’s not how you’re supposed to do it.”
“Oh?” He questioned me.
“I’ll show you. Put your cock back inside me.” I was on the edge of the bed, and he was standing up, holding my feet in the air. When he put his cock back inside me, I made him stop. And then I pushed him back, sat up, and licked his cock clean. “A few more times like that, and I’ll be dry enough to do some more serious fucking.”
That got him so hot; he came a few minutes later. “Shit!” I exclaimed, “Now we have to dry me up again.” And then I sat up and licked his cock clean again. When he was clean, I began using my fingers to scoop his cum out of my pussy, licking them clean, and repeating until I was sufficiently dry to fuck again without chafing us both.
“Wow!” He exclaimed, “That’s the hottest fucking thing I’ve ever seen.”
“Oh, your bimbos didn’t like the taste of your cum mixed with theirs? I love it.”
He just shook his head with a big smile on his face.
“One of these days, I’ll have to let you watch me eat your cum out of a pussy.”
“Next weekend?” He asked me with a huge grin on his face.
I gave him a soft kiss on the lips, “I don’t happen to have a bimbo on call, do you?”
“I might be able to find a volunteer.”
I giggled, “When I get to the office on Monday, I’ll check my social calendar.”
When Darren walked me out of his front door and to my car after lunch on Sunday, I kissed him passionately, and then I told him, “I’d like to meet her first.”
“Who?” He asked me with a confused look.
I slid into the driver’s seat of my car and looked up at him, “The bimbo we’re both going to fuck next weekend.”
He looked totally shocked, “You ... you were serious about...”
“Darren!” I scolded him. “It’s just sex, right?”
“Right, okay ... okay then.”
I thought there might be some tension between Dr. Wilshire and myself at work on Monday—sexual tension, but both of us managed to maintain a very professional demeanor.
It wasn’t until the end of our after appointments review on Tuesday that he told me, “I’ve arranged a dinner meeting for tomorrow, if you’re available.”
“Oh?” I cocked an eyebrow, “Am I going to meet someone?”
“If you still want to.” He said with a little apprehension in his tone.
I chuckled, “I’m guessing you didn’t have to dig too deep into your little black book to come up with a willing bimbo.”
“Not that far, no,” He told me with a grin.
I was more nervous than I thought I’d be. I’d done a threesome with my long term boyfriend in college, for his birthday and a couple of other times, but I wouldn’t say it was second nature to me.
We were waiting in the restaurant bar when Linda entered. Darren hurried to greet her. On their way back to me, he informed the hostess that our other party had arrived, and we were ready to be seated.
I found Linda to be very personable. She was a cute blonde, around my height, five seven or eight. She had a beautiful smile and an infectious laugh. She was shapely and appeared fit. She was wearing a beautiful, sexy dress with a plunging neckline that showed off her prominent breasts, but not in a trashy way at all.
After some small talk and ordering our food, Darren took his drink back into the bar and sat where he could see when our food was delivered.
The instant he was out of earshot, Linda asked me, “So, what’s your secret?”
“Secret?” I asked.
She appeared to be trying to decide if I was for real or playing coy, “Darren and I dated for a couple of months. We got along okay, but we just didn’t click—or at least, I didn’t click for him. I tried everything, and I even offered to do a threesome with him, but he wasn’t interested. And then yesterday, all of a sudden, he called me out of the blue and asked me to join him for a night of fun with you. So naturally, I’m curious.”
I sighed, “I’m not sure how to answer that. We’ve known each other for almost a year, and we’ve been working together for six or seven months, but last weekend was the first time we’ve been intimate. I guess we just clicked.”
She seemed genuinely surprised. “Wow! And you’re already inviting a third into your bed? If you don’t mind me asking, was it your idea or his?”
“Actually, I may have planted the seed when I was teasing him during sex, but I didn’t really expect him to jump on it like he did.”
“But you have done it before, right?” She asked while staring straight into my eyes.
“Yes, three times, always with the same girl and my college boyfriend ... and yes, I did enjoy it.”
“All of it?” She asked me skeptically just as our food was arriving.
I looked toward the bar and saw Darren heading our way. He was there before they finished putting the food on our table.
I waited until the staff left, and then I told Darren, “Linda was just asking me if I enjoyed my limited experiences with threesomes. I was just about to answer when the food showed up.” And then I looked back at Linda, “Yes, as a matter of fact I did ... and yes, all of it.”
Linda looked at Darren, “I’m in if she is.”
“I’m more than in.” I told them both, and then I looked at Linda and winked, “I’m anxious.” Which was true. I was nervous about it, but excited too.
As it turned out, Linda wasn’t without a capacity for flirting and teasing herself. After our meal, she and I excused ourselves to the ladies room.
Once inside, and after exiting our respective stalls, we were at the sink when she said, “When we get outside, the two of you should walk me to my car.”
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