The Cougar and the Anaconda

A huge thank you to ngnx and lumberjackme99 for their help.

*****

This is the second chapter of The Cougar and the Anaconda. Candace is a 49-year-old partner in a Dallas law firm who is having an affair with Jeremy, a 24-year-old law student who will be starting at another big firm, Parker & Hanson, when he graduates. Candace's husband and Jeremy's wife are oblivious to the affair. Enjoy!

*****

DAY 6: PLANNING

My cock twitched in anticipation as the train pulled into the station. As usual, I waited at the end of the platform to get the same car Candace rode. My eyes were drawn to her when I got on. She was wearing a red dress with a white necklace draped not-so-innocently between her breasts. She looked sensational. And even more, fuckable. I sat down next to her.

"Hey there, sexy."

She placed a hand on my thigh. "Hi, young man."

"Not so young for much longer."

My birthday was coming up. As was hers, since we were born a day apart. Well...a day and 25 years.

"I know: 24—you're practically retired. Speaking of birthdays, I'd like to spend some of this one with you."

"How can we make that happen?" If I was honest with myself, celebrating our birthdays together wasn't just about getting my rocks off. I wanted to be with her because I cared about her. But with my very pregnant wife, Britney, at home, and Candace and I having demanding jobs, we struggled to sneak away. Making excuses to Candace's husband, George, added to the challenge.

"Our birthdays fall on Friday and Saturday. It would be impossible to sneak away from George and Britney on the weekend. What about Friday lunch?"

"Parker has me in a hearing all day. I won't even make the train, much less lunch."

Candace had gone to law school with Parker. "I should call him and bitch him out for interfering with our fuck time."

Candace was so sexy when she got possessive of me. "I have an solution. Can you come to happy hour?"

"Is it hosted by your firm?"

"Yes."

"I don't want to show up as a married man's date at another firm's happy hour."

"Since I'm a summer associate, the partners expect me there."

"What about dinner? George will be out of town, so I'm free Friday night."

"I don't have that excuse with Britney."

"Text her from happy hour and tell her the guys decided to take you out on the town."

"You're devious."

"No, I'm horny."

"Me too."

"Do you want to reserve a room?"

"Absolutely. Are you OK with room service dinner again?"

"Perfect."

Shortly before my train stop, Candace caught me off guard.

"Jeremy?"

"Candace?"

"Let's assume that you're going to be faithful to your wife for the rest of your life. So this is it, your chance to sow your oats. Is there any one thing you've been wanting to try that you know you won't get to do with her?"

"There's a laundry list. Britney has never been adventurous in bed, and anything that isn't vanilla is off the menu."

"What's number one on your list? And don't say threesome or gang bang or orgy."

I could be a smart-ass. "Well, you just gutted my list."

Candace taught me two could play at this game. "OK, we'll stick with missionary."

I realized the error of my ways. "Whoa, let's not be hasty. Ruling other participants out, I'd go with anal."

"Of course you would, that's exactly what the biggest guy in the city goes for."

"Sorry, not trying to be greedy, but no woman has been willing to try."

"For good reason, stud."

"Do I need to find an option behind door B?"

"Not necessarily. Your birthday is coming up, after all...Get that grin off your face. This goes in the 'maybe' category."

"Well, 'maybe' isn't 'no.'"

She rolled her eyes at my exuberance.

I kissed her on the cheek and hopped off the train, distracted for the rest of the day with thoughts of Candace's cute little ass.

I was also torn: in a couple months, we would be moving back to New York, where I was going to law school and presumably would join a firm. That didn't bode well for seeing Candace again. I was going to miss her, and not just her cute ass.

DAY 7: AN OFFER I COULDN'T REFUSE

On the Thursday before my birthday, Monica, the managing partner at Parker & Hanson, called me in to her office. A painting that looked like a male torso hung on the wall—kind of erotic for a professional setting. A similar sculpture of a reclining male nude sat on her bookcase, penis on show. I didn't consider myself a prude, but it seemed inappropriate for a law office, especially one belonging to a top lawyer in the city. Other than those pieces of art, it was sterile and decked out in shades of black and gray.

She shut the door, which was the first clue that something significant was up.

Slinking toward me, Monica looked very much like her office, dressed in grays and blacks, but with distracting gold jewelry and overblown make-up. She looked like she had been busy working her way to the top in her 40s and forgot to get married, have a kid, or do anything in her free time besides drink martinis and prey on young male associates. I was feeling like the next mouse in her talons.

Sitting on the corner of her desk, Monica launched into a spiel about how happy the firm was with my performance. Her skirt was hiked up, and I struggled to pay attention as I was at eye level with her red lace panties visible beneath her navy suit.

"We're thrilled with your performance and think you'd be a good fit with the culture of our firm."

Should I tell her about her underwear showing?

"Obviously, we're aware that you're at school in Columbia, you went to undergrad at Harvard, and we have no doubt that you've received offers from top-tier firms in Manhattan. But we also know that your wife is from Dallas, and with your firstborn coming, you might like to stay closer to her family. And you have to be carrying some serious college and law school debt."

Thank goodness, she moved to sit next to me, taking away the awkwardness of peering at her panties.

"We'd like you to be a part of Parker & Hanson."

Gold bracelets jangled as she put her hand on my upper thigh, which was a little close for comfort.

"We're willing to do whatever it takes to keep you. We're prepared to match your highest offer from any other firm, including in New York and including all bonuses, and beat it by five percent."

I gulped. That was a sweet offer. But she wasn't done.

"Your debts likely run in the hundreds of thousands of dollars. We'll take over those loans for you, law school and undergrad."

I was starting to get suspicious. This was too good to be true.

In an awkward move, Monica ran her hand down my arm and rested it on my hand.

"All we ask is that you agree to work for us for five years. Most lawyers stay seven years or more, so I think you'll want to stay well beyond five anyway, especially since you'll be on partner track."

"This is a generous offer. May I have some time to talk it over with my wife?" Maybe mentioning my wife would get Monica to back off.

Monica didn't take the hint. Ramping things up, she reached over and stroked my cheek.

"Of course. Take all the time you need. Jeremy, my door is always open to you. Anything you need, whether work-related or private, I want to be here for you."

I stood to leave and put out my hand for a polite handshake. Ignoring my hand, Monica wrapped her arms around me in an embrace. She smashed her breasts against me, and for the first time I understood what guys meant when they said they could feel the difference.

"You're a handsome young man, and we would love to have you here."

I was uncomfortable that my looks had anything to do with the deal. "Um, thanks for the offer."

"Swing by Parker's office before you leave."

"OK. Thanks again."

***

Parker had the nicest office I'd ever seen, including those on TV. The firm was in Fountain Place, designed by the architect I. M. Pei. He had a corner office that could have fit a conference room, in addition to the pool table that he was so proud of. He had spectacular artwork, including an original Andy Warhol. Unlike Monica's, his office was plush, with Chinese rugs and multiple sofas. It was easy to feel at ease, if a little jealous.

"Hi Mr. Parker, you wanted to see me?"

"Jeremy, call me Parker. Have a seat. I gather Monica spoke with you?"

"She did. Thank you for the generous offer."

"We want to keep you. We're willing to do what it takes. If there's something else you and Britney need, let us know. If we can make it happen, we will."

"I'm honored, sir, thank you."

"Our pleasure. Why don't you take the day off so you and Britney have extra time to talk this through?"

"Sounds great. Thank you."

I'm glad he couldn't read my mind, because he would have figured out that all I wanted to do was see Candace, not go home to my previously-loving wife to talk his offer through.

Britney and I had decided to wait to have kids after I was out of law school. Without telling me, she went off the pill, got pregnant, then decided we wouldn't have sex or any other affection during the pregnancy. It had been a long eight months and had put a tremendous strain on our marriage. I was falling out of love with her, especially for her betrayal. With the baby coming, I felt enormous guilt about that.

Unlike Britney, Candace was proving to be an honest, adventuresome lover. If there was one reason to stay in Dallas, Candace was it. Little did I know, she was about to make it even harder for me to want to leave.

DAY 8: BIRTHDAY GIFTS

Friday finally rolled around, and we met up at ZaZa. The music was loud, the drinks were plentiful, the place was packed. Candace pointed out that she was ten years older than the next oldest person, and she complained that the 20-something-year-old women were checking me out like I was a piece of chocolate cake.

For me, there was only one woman in the room. She had come straight from the office and was still wearing her suit—a gorgeous red number that made my mouth water. Most of the other women at the bar had painted their dresses on with miniature brushes. Candace said she felt self-conscious and old. I tried to tell her she was the sexiest woman there, but she dismissed my compliment.

I flashed the room key. "Let's go."

That brought a smile to her face.

We barely made it in the room and our clothes were off. My eyes widened when I saw her black crotchless lingerie, garter belt, and stockings. She left her red high heels on for full effect. Not what I was expecting. But a nice surprise.

While drawing my teeth down her neck, I pressed her breasts against the door and rubbed my swollen cock in her crack. I pushed it toward her pussy, nudging the crotchless fabric out of the way, and appreciating how wet she already was.

"Is this sweet cream all for me?"

"That's what you do to me."

"I love it."

Spinning her around, I slipped my tongue into her mouth then slid it in and out. "This is how I'm going to fuck you with my cock." We both moaned in anticipation.

I played with her like a child with a new toy. I bounced her breasts, grinning as I appreciated their weight. I took turns running my fingers on their undersides and moving higher to fondle her nipples. They tightened into firm buds eager for my mouth, which I sucked through the sheer fabric of her lingerie.

I reached between her legs and smiled when I felt the juice leaking out.

"Candace, you're a dirty woman."

"I am?"

"You are. And I'm the man to clean you up."

Sliding onto my knees, I brought one of her legs over my shoulder. She leaned back against the inside of the hotel room door and balanced on me.

She had that sharp, aroused woman scent that drove me insane. I pulled the thin crotchless fabric apart so I could taste her sex, thick and musky with desire. Dragging my tongue along her sopping slit, I smacked my lips.

"Delicious. I don't need strawberries for that pussy."

I stabbed her wet hole with my tongue and ran it in and out, gathering her nectar in my mouth. I slid my slick mouth up to her clit, which I teased to Candace's pleasure.

"You're good at that for a man so young."

I raised my eyes to hers in appreciation. Sometimes I was self-conscious about not being experienced enough for her, so I was grateful anytime I could satisfy her.

Her leg on the ground trembled, and she fumbled for the door handle to brace herself. As I pleasured her clit, I ran my finger along her taint and stopped before her puckered hole.

I was caught off guard. "What's this?"

"It's a butt plug."

"Seriously?"

"Yes. I want to give you what you want."

"You're a little woman. I'm not sure we can do this."

"We can give it the old college try. You're still in school, right?"

I grinned. "And you're playing professor?"

I swooped her up and laid her on the bed. "First, though, I need to be in your pussy."

I dragged my dick along her wet slit, running the excess moisture up to her clit. She grinned and moaned every time my tip stroked her sensitive bud. I ran it in circles, teasing her entrance as my head pushed her lips to the sides. She thrashed around like she was desperate for my cock.

"Jeremy, fuck me already!"

I was crazy about this woman and could never tire of hearing my name on her lips.

I eased myself into her, lifting her legs to find the perfect angle. I started slow, not wanting to hurt her.

"Speed it up. I need you to fuck me."

"I don't want to hurt you."

"You won't. Let's go. Fuck me already."

"Yes, ma'am."

I wrapped my arms around her shoulders to anchor myself to her, then I pulled back and drilled into her as hard as I could. Her entrance stretched beyond its limit and her channel expanded to accommodate me. Her breath caught when I pushed against her rear wall with my head.

Candace lost control, yelling all sorts of nonsensical words. The only word I could make out was the one that shot straight to my cock—my name.

Her pussy contracted to fight me out, her legs locked up to squeeze me away. That pressure added to the feeling of fullness and put the right pressure on her clit, causing Candace to rake her fingernails down my back. Staring into my eyes, she was disintegrating into me as I claimed her.

Her pussy vibrated around me, fastening onto my shaft like an undulating vise. I clenched my teeth in a desperate bid to hang on through her orgasm.

Even as she cried out, I didn't slow my thrusts; they grew harder and faster, filling her need and sowing my own. My balls tightened against her ass as my cum drove through my shaft and out into her, stuffing her with warm, milky syrup. Tingles of pleasure shot up my spine and down my legs, rendering them numb and unstable. I pulled out and fell to her side. A feeling of calm, almost Zen, washed over me.

We laid on the bed, panting, laughing at what we had done. I loved fucking her. She was fun. She wasn't afraid to come unglued with me, and I felt the same with her.

Parker & Hanson had no idea about the biggest selling point of their offer: If I stayed in Dallas, I got to keep seeing Candace. That was worth more than all the bonuses they could offer me.

But I had more pressing matters to attend to.

"Tell me about this butt plug."

She was still gasping for air as she laughed. "It's supposed to help widen me. I also have lots of lube that should help, well, lubricate things. So hopefully, between those, and some creative play, we can get you back there."

As she described the toys, I was hardening again. Candace looked down at me. "My husband would kill to be able to get an erection again so fast. The perks of being 23."

I smirked. "Almost 24. Almost too old for you."

She slapped me on the arm. "I might keep you around anyway."

"Back to the butt plug."

She asked me to pull out the plug, which intrigued me. It had a fancy "gem" that stuck out the end which made us both laugh. Nothing like a bejeweled asshole.

I rubbed a generous amount of lube on her hole and played around with my fingers.

"Easy, big boy, I don't do this every day."

I teased her, running circles around her tight hole. I tickled her, causing her to laugh and loosen up. When she seemed ready, she urged me to insert one finger. "Slide it in circles and in and out. But go slow."

I rubbed my finger in and out then circled it around and around, trying to stretch her out as I went.

"That feels intense. Maybe I'm crazy to think I can do this."

I wanted this more than I could remember wanting anything in a long time. I needed to convince her to try. "We can stop at any time. And I will stop the second you tell me to. Let's try."

I know she was determined to give me this gift, and no one makes it through law school without determination. "OK, add a finger. But do it slow."

I lubed up my next finger and slid it in with the first.

"How's that?"

"The fullness is less overwhelming, but more bearable after the first finger."

I scissored my fingers back and forth, opening her still further. I was getting turned on. "Fuck, I want in there so bad."

"You want some of that ass?"

"More than you know."

"You better prepare me good if you want me to take you."

"I'm doing the best I can."

I scissored my fingers wider and more vigorously, causing her to catch her breath. I hoped I wasn't making her question our plan. But I was a man on a mission, and she was a woman hell-bent on pleasing her man. We were going to make it happen.

"Add a third finger and twist them all around."

I added another finger. I twisted them all in her ass, scissored them back and forth, and ran wider circles around her asshole.

"Put them all in."

I slid the fourth and fifth fingers in, filling her up and taking her breath away when I spread my fingers apart. I played with her hole, stretching it open further and further until I could see into her channel.

"Fuck, that's hot. I need to be inside you."

"Jeremy, if you want me to take you, we're going to need more than your fingers."

She walked over to her briefcase and pulled out two large vibrators. She handed me the purple one. "Tease me with this."

I put the tip inside her asshole. "I can't believe I'm doing this."

I could hear the smile in her voice. "It gets more intense from here."

Once I had it half way inside her, she told me to turn it on. "Oh god, that feels good." I glided it in and out, further in each time.

"You have to get it all the way in."

"All the way?"

"If I can't get that in, then I'm not going to be able to get you in."

Logic and the desire to fuck her up the ass were powerful motivators. I pushed further until I saw the end of the vibrator against the rim of her hole.

"Now turn it up." I did as she asked, and she started rubbing her clit. Almost immediately, she flew into orbit, wracking her body and loosening her hole. She pumped her ass back against the vibrator. It was slick with lube, and I scrambled to hold it in her ass as she bucked against it in ecstasy. Screaming out my name and a handful of profanities, she reached back to shove the vibrator further in her ass.

"Fuck, Jeremy, fuck my ass, fuck that tight asshole baby. Fuck it deep. Oh god, yeah."

After an orgasm like that, she was as ready for me as she would ever be.

"You can take it out now."

I slid it out.

"I'm ready. But go slowly."

She got on her elbows and knees, a pillow cradling her full breasts. I took a deep breath. I wanted this to happen so bad. No other woman had ever even let me try. But I did not want to hurt her.

I placed my head against her stretched hole. I started to push, and she expanded for me, allowing me to punch through her ring of muscle. I was already in ecstasy.

"Oh fuck, Candace, oh fuck."

Candace struggled with my size. All the preparation in the world couldn't get her ready for my girth, and once I was in, my length would be a challenge. She took deep breaths, which helped me slip in a couple inches of my shaft. I looked down at my cock, my mind exploding at the sight of it in her ass.