The Assistant

The first Saturday that the weather cooperated, I was nervous about seeing my boss in a bikini or swimsuit. We finished around twelve thirty and Jennifer brought out a tray of sandwiches, snacks, and a bottle of white wine. The fruit of the vine lowers my inhibitions and can make me downright horny.

"I'm hesitant to serve wine since this is work related...but I'll keep an eye on you...make sure yer sober when you leave." She said with a smirk.

We ate and drank heartily until,

"Hey, it's hot out here. Ready for dip or swim?"

"Ah, yeah...where can I change."

Jennifer showed me to what looked like a charming miniature Victorian cottage but was a changing room. My nerves were on edge and when I walked out and saw my boss in a red, white, and blue striped bikini, my jaw hit the deck. My god, I was stunned. She looked like a lesbians dream with a lean hard body. Her suit fit her to perfection and looked painted on her body.

"Paige? Are you ok? You're staring."

"Oh...ah...sorry."

Hastily I looked away, but I was busted! I futzed around with my beach bag and heard Jennifer in the water.

"Hey, are you coming in?"

Slowly I walked to the pool ladder and lowered myself in. I did notice that Jennifer was giving me the once over from head to toe.

She was quite the accomplished swimmer and did laps with ease.

"You make it look so...effortless."

"Oh, it seems like a hundred years ago, but I swam competitively in high school and at university."

By now we'd been spending a lot of time together practicing yoga, hanging out afterwards for a coffee and a sweet treat, time permitting we'd go shopping even though I couldn't afford to buy anything. I had just enough after payday for rent, food, utilities, a cell phone, and the expenses for everyday living. Any frivolous needs were off the table. If I wanted to buy clothes, I exclusively shopped sales with deep discounts.

Jennifer Dell'Angelo was my straight gal pal and a joy to be with. Our good times were peppered with laughter but also intelligent conversation. Little by little, my infatuation grew to puppy love. That's the best way to describe it.

Then one very hot Saturday I forgot my bikini top.

"Shit! I only brought bottoms." I said with the changing room door open. Of course,

Jennifer heard me.

"That could be a dilemma but..."

My boss had a twinkle in her eye.

"Since its just us...who needs a top."

Before I had a chance to say anything, my boss took her top off and the sight of her breasts took my breath away. She was no larger than a "B" cup, they were round, rode high on her chest and the nipples, long cylinders with a flat top. I'm very fond of tits, especially ones like Jennifer's. They were mouthwatering and I couldn't stop staring.

"Paige?"

I snapped out of my brain fog.

"Oh...ah...sorry."

Jennifer dove in the pool and I gazed longingly at my beautiful boss swimming laps. While I sat on edge next to the pool ladder, feet dangling in the water, I fantasized about having a relationship with her. She was straight and while I thought I could seduce her, I wanted more than just sex. The yearning in my heart was clear evidence.

Eventually, Jennifer stopped and ascended the ladder with water dripping from her awesome body, particularly her breasts. Again, I gawked at the amazing sight and again I was busted! After she reached for a towel and was drying off with a quizzical expression, she sat on a chair and waved me over.

"Have a seat..."

I sat next to her with, I'm sure, an embarrassed look.

"Can I ask you...ah...personal question?"

"Sure boss, fire away."

"Hmm...I wish you hadn't called me boss but...since we're not in the office and not officially on company time...are you attracted to me?"

I felt my face grow ferociously hot. We'd been working together for six months.

"I see..."

"I'm sorry...please don't be mad."

I genuinely feared for my job.

"I'm not mad, far from it...very flattered actually."

Then she hit me with a bombshell.

"...because I'm attracted to you."

I think my jaw must have hit the pool deck.

"You are?"

"Since the day of your interview. You shook my hand and sparks shot up my arm."

She smirked.

"I felt the same thing!"

"Please don't think I'm being forward, and I have no right to ask, but are you gay?"

"Yes, I prefer women...

"I must admit...this is a new experience for me. I've always found women's bodies to be fascinating and I have a genuine appreciation for the feminine form but not in a sexual way...until now."

Jennifer looked very thoughtful with a serious expression.

"You mean...you find me..."

"Yes, I do. Surprised the heck out of me but I've often wondered what it would be like to kiss you, to run my hands over your naked body...and that butt...baby got back."

"Jennifer if you only knew how many times, I've wanted to make love to you."

"Paige, we have a big problem...I'm married."

Her last statement was like a bucket of ice water in the face. I lowered my head and gazed forlornly at the ground as tears rimmed my eyes.

"Hey, why the tears?"

I spent the next ten minutes telling Jennifer my sorry track record with straight married women. After I finished, I sat there like a naughty child waiting for a reprimand.

"I just...oh...I should probably go..."

"Go where? Just when things start getting interesting, you want to leave?"

"Boss, I don't want to create any problems for you..."

"I'll let you know when that happens but let's go in the water, it's way too hot out here..."

In the pool, Jennifer turned, put her arms around my neck and held me very tenderly. The intense look in her eyes reduced my insides to jelly.

"Now, where were we? Ah, yes, the problem...his name is Ray."

I was at a loss for words. What does one say in that type of situation? But I felt like the ball was in Jennifer's court.

"What I'm going to say may sound like a justification but it's not. I've been true blue since Ray, and I started dating. We've been married eleven years and dated for four. That's fifteen years and I honestly never considered cheating on him until you came along. You're sweet, kind and have this innocence that is very charming. I guess it's your mid-western roots, growing up in a small town.

You've been my friend as well as a colleague. Introduced me to yoga and quite frankly, your presence in my life has filled a void that was growing larger and deeper by the day. I've had the hots for you for quite some time and was in a quandary about how to handle it.

On a professional level, it's inappropriate, and it could cost us both our careers, mine for sure. I did feel that there was some mutual attraction, but I really wasn't positive. However, working with you here, I saw how you looked at my body in a bikini and while it surprised me, it reminded me of how guys would give me the once over in college. And it was clear that you really liked what you saw.

But it's more than that, much more. You have this affectionate nature that I adore. The way you look at me with soft, warm eyes and behind them I believe that you have some deep feelings for me."

Jennifer's soul-searching gaze bore into heart.

"Our life, mine, and Ray's, has grown stale and predictable. We are married to our careers as well as each other but the fun, the spontaneity has disappeared. We're more like roommates. I had a premonition that if the right person came along, I'd wind up cheating on him. It could have just as easily been a man. But, to my astonishment it was you, Paige Gallagher, a woman, and it makes no difference to me."

My half-naked boss put her hand behind my neck and pulled my face toward hers.

"Kiss me...please kiss me...I've waited long enough..."

Our lips met in a sensual embrace, and it felt so right, so good. After many closed mouth smooches, her tongue snaked past my lips, and we frenched like mad until my pussy was creaming. Finally, we took a breather, both panting like two racehorses that just ran the Kentucky Derby.

"Damn, girl...you sure know how to kiss." She said breathlessly.

"So do you..."

That started another titanic make out session. Finally, with her breasts against my breasts, her nipples felt rock hard.

"The way you were looking at my ah...chest earlier. You really like my tits?"

"Yeah...they are so hot."

"I've always thought they were small."

"Not at all...they fit your body perfectly."

Jennifer beamed with pride.

"Wanna feel them?"

My hands with a will of their own cupped her breasts. They were simply superb in every way.

"Hmm...yer hands feel soft."

"They're so firm..." I moaned.

I ran my thumbs over her stiff nubs, flicked back and forth eliciting a groan from Jennifer. Very lightly, I pinched the swollen protuberances between my thumb and forefinger.

"That feels soo good..."

Completely mesmerized by the length and hardness, my will was not my own as my lips closed over Jennifer's left nipple. Gently I suckled, drawing on the protuberance until it was diamond stiff. My boss arched her back.

"Oh my god...don't stop...it feels fantastic!"

I tongue whipped the end skillfully as my lips exerted the right amount of pressure. My sexy boss held my head as I hungrily fed from her nipple. Back and forth I went, trying to get my fill. Most of her small breast was in my mouth, as I lashed the end, sucking hard then soft. I suckled and suckled until I was delirious with desire.

"Oh yes...suck!"

I switched and clamped my lips on her right nipple, suckling like there was not a tomorrow. My fingers pinched the nipple I just vacated, and the added stimulation was having an effect as she started humping her pussy against my thigh.

"Oh...oh...oh..." she moaned constantly.

My hungry mouth sucked harder, drawing the nipple in until it was distended and granite hard, tongue lashing the flat top mercilessly. Her humping was more intensive, grinding against me as I stiffened my thigh muscle.

"Oh...oh...oh god...oh god!"

Quickly I switched and buried my mouth over Jennifer's left nipple again. Sucking wildly, squeezing, and stroking her beautiful breasts. With my lips gripping the taut flesh, I sucked hard, hollowing my cheeks like a nursing infant.

"Oh my god...I'm gonna cum!" she wailed.

As I ravaged Jennifer's tit, sucking hard, then soft, varying degrees of pressure, tongue whipping the end, she soared to an orgasm.

"I'm cumming...oh god...I'm cumming!" she wailed.

Holding my head tight to her throbbing breast, she ground her vagina on my thigh. Then her body grew rigid, and she was lost in the throes of an intense orgasm. I suckled gently until I felt her body relax. When she slumped against me, her breathing returned to normal. We were silent, locked in an embrace.

"That was soo intense...I haven't cum like that in...I can't remember if I ever did..."

Jennifer looked sexually satisfied, at least for the moment.

Suddenly I felt sheepish.

"Hey, you give me the best orgasm of my life and now your shy. That is some talent you have!"

Jennifer pulled her bottoms away from her flat tummy and looked down.

"Thanks to you, I made a mess in there."

In the worst way, I wanted to plunge my hand inside and extract her juices for my hungry mouth. Instead, I settled for cupping and tenderly squeezing her vagina.

"I wanted to make you feel good..."

"Feel good? That is the understatement of the year. My nipples are very sensitive, especially the left one but Ray doesn't pay much attention to them."

With my arms around Jennifer, we kissed again like two very horny teens.

"Hey, I hate to break up the party, but Ray will be home soon. He's taking me out to dinner. I'm sorry because I'd really like to reciprocate. In case you haven't noticed, you have a hot chest too!"

"Do you feel guilty?"

Jennifer looked very pensive.

"Right now? No, maybe later after it has sunk in, I might. But something tells me I won't."

We kissed some more as I got the feeling that Jennifer did not want to let go of me.

"I wish you could stay; I really want to return the favor, but I know he'll be home any minute...I'll see you Monday."

When I arrived at my apartment, I masturbated like a mad woman. In fact, I jilled until I was literally exhausted and wanted Monday to arrive in the worst way.

JENNIFER:

By the time I cleaned up out by the pool and changed into more formal attire, Ray pulled in the driveway. My nipples still tingled from the most intense sexual experience of my life, and I masturbated in the shower, bringing myself to another breathless orgasm.

At dinner, I was quieter than usual, and Ray noticed.

"You seem distracted. Anything happen I should know about?"

His question caught me off guard, but I quickly recovered.

"No, just work is taking up a lot of my time..."

"Well, it'll pay off in the long run."

After dinner, we sat in the den and watched TV with a glass of wine. The entire time I kept thinking about Paige. I hungered for her...it was a resounding desire in my body. Although I was clueless about girl sex, I knew all the female parts and what would make her feel good.

The next morning, sex with Ray was dull and practically lifeless. He ignored my breasts, even when I put his hands on them. There was a minimal amount of foreplay, and it was wham, bam, thank you ma'am. I can't honestly remember the last time he went down on me, but I'm expected to give him head. That morning was the first time, I refused him the pleasure.

When it was over, instead of lingering in bed, I immediately went to take a shower. In the middle of bathing, I saw the door open, and Ray sat on the toilet lid.

"I'm almost done, then you can get in."

"That's not why I'm here."

"Well...?"

"What's wrong Jen? You seem distant."

"I've been thinking, our sex life is dull, and I don't get much out of it. Do you even care that I rarely have an orgasm when you get your rocks off every time?"

"I don't have an answer for you."

"Doesn't it seem very selfish on your part? I thought we were equal partners but not between the sheets. There is zero spontaneity, every Sunday the same old, same old." My tone was scathing.

"Jen, we have very busy lives. Sunday morning is just about the only time we have for it."

"All right Ray, if this is how it's going to be, then I'll pass on the sex. You can masturbate for all I care. Your answers are piss poor. Instead of trying to confront the problem, you give me lame excuses."

"Jesus Jen, what the hell is wrong with you?!"

"Nothing but I'd like to have some spark back in our marriage. It's the same tedious, and I mean tedious routine, week in and week out! Saturday night we go out for dinner, Sunday morning sex, if you want to call it that, then the movies or a museum and its back home to "Dullsville!"

"I just don't understand Jen where all this is coming from..."

"Oh, you don't! Think hard Ray, think hard about what I said. I'll be out the rest of the day, by myself."

With that I left the bathroom in a huff. I dressed casually and called my sister.

"Hey sis, got some time for a bitch fest?"

"Yeah, what's wrong? you sound stressed."

"I rather do it in person. How about the Eagleville Taphouse, say in an hour?"

I met my sibling in the bar, and we sat at a corner high hat table.

"Thanks for doing this."

"Pete's playing softball with the girls in the backyard. He loves doing it."

My sis was the proud mother of four girls with loads of talent in sports.

"So? Spill!"

For the better part of an hour, I related my dissatisfaction with Ray and our marriage.

"What brought this on? You always seemed satisfied with the situation."

Anna had a curious expression that suddenly changed to surprise. She worked as a psychologist for the school district, and she could be very insightful.

"You met someone."

I simply nodded my head.

"Damn, I'm shocked! What's he like?"

"I didn't say it was a man..."

"Oh my god! A woman?"

"Yes, and she's a lot younger..."

"Did you have...sex?"

"Yeah, and it was fantastic!"

"My god Jen..."

"Here's the bad part...she's, my assistant."

Anna was smiling and shaking her head in disbelief.

"From day one, I've had a crush that just kept getting worse and worse. Turns out she had the hots for me too. Finally, yesterday..."

"Oh my god...girl. So, what's next?"

"I dunno but I'm going to take it one day at a time. See where it goes...All I can say is, she rocked my world!"

Anna insisted that I go home with her and have dinner with the family. I couldn't refuse. My nieces greeted me very warmly and there were hugs all around. I was helping Anna prepare dinner when she talked about something that I never suspected.

"I thought you had the perfect life. Both of you are accomplished professionals with a big house, expensive cars, pool, vacations to the Caribbean and Europe. I've always been jealous, but I have Pete, the girls and I wouldn't trade that for anything. I guess money can't buy everything... but it sure does help!"

"Anna, I had no idea you were envious of me. You hid it well!"

"Jesus, Jen, yer my sister and I love you a heck of a lot."

Her words brought tears to my eyes, and I hugged her from behind.

"Thanks, that means a lot to me. I love you too big sis!"

To break the sadness, I cupped her big breasts and squeezed.

"I'm envious of these...damn! They are huge!"

"Yeah, I lucked out in that department!"

While we were talking, my cell phone went off several times with texts from Ray. I ignored them. After dinner, I lingered for a while, but it was time to go home and see if he wanted to talk.

When I walked in the house, he was in the family room, drinking wine and seemed tipsy.

"I see you decided to come home." He said angrily.

"Are you drunk?"

"Yep...sure am."

"When you're sober, we'll talk."

I walked out, leaving him to his own devices. As I sat in den, I wondered why I failed to see this side of him. It wasn't like this in the beginning, and I blamed myself for not doing something about it much sooner. Why was I blind to this? Why did I let it deteriorate for so long? Why was I so complacent?

Paige opened my eyes to what was missing in my life. My marriage was in trouble, it was plain to see. Could it be fixed? I was doubtful unless Ray changed his attitude. We needed a marriage counselor.

Monday, I arrived at the office early and waited for Paige. When she put her purse away and opened a file, I called her into my office. She had a worried expression on her pretty face.

"Please close the door, we have something very important to discuss." I said with a stern expression.

Paige had a hangdog look as though the axe was about to fall. I walked out from behind my desk and as soon as she turned to face me, I took her in my arms and kissed her hard several times, driving my tongue past her lips. I held her very tightly and whispered in her ear.

"Oh god, I want you, Paige. I want to make love to you...I've been dying since Saturday...please say you'll let me."

"Yes, yes! I want you too...but how?"

"We'll take a long lunch and I mean LONG lunch and go to the Four Seasons down on JFK Boulevard."

Paige kissed me with deep passion and my body responded, nipples hard as a rock and vagina creaming.

Trying to work through the morning was a joke and at eleven thirty, we left. I insisted that we eat and took her to La Petite Maison, probably the best French bistro in the city. The food was exceptional and before the first course arrived, I took her hand and wouldn't let go. We exchanged fond glances but just before dessert, I saw tears in her eyes.

"Is something wrong? Are you having second thoughts?"

"Noo, noo. I'm just so happy that I can't help it. I had hoped that I didn't ruin anything. I felt like I came on too strong and I wanted to text or call you Sunday, but I was afraid..."