The Break Up 5

"I'm lying alone with my head on the phone, thinking of you till it hurts..."

Why does that damn Air Supply song have to come on the radio now?

It's been a month since the love of my life Cara left me when she caught me fucking my new hot boss Jill.

Let me go back to the beginning and tell you this whole story.

My name is Greg, I'm a 45-year-old, 5-foot-7, 190 pound, a 38-inch waist - so yes, more fat than muscle - brown hair, brown eyes, glasses, and a small-to-average sized cock. I work as administrative assistant for a small company. Weird job for a guy, but it's something I fell into after getting downsized out of my previous job as a legal assistant. I was having trouble finding work in the legal field and decided to make what I viewed a lateral move. I liked working as an assistant, taking ownership of my work, helping the manager make the company run effectively and profitably. Liked it that is until Jill came along. More about her later, for now I want to focus on Cara.

Her personality was just as beautiful as her looks. She's 5-foot-4, 150 pounds, curves in all the right places, 36C breasts, short black hair, blue eyes, with a laugh and smile that simply made her more attractive. She had a great sense of humor and a heart of gold caring for me deeply.

We had met through Match.com and hit it off pretty quickly through e-mails. We met and there was a special spark between us. I was smitten with her. Two days later we had a wonderful second date. On our third date Cara and I were sitting around in my apartment making out. We were kissing passionately in a tight embrace. I got bold and moved my hand under her skirt and started rubbing the outside of her panties. She moaned softly and started licking my neck. I took that as a positive sign and slid a finger inside her panties and started to finger her pussy.

She responded by moving a hand to my crotch and rubbing my cock through my jeans.

"Can I stroke it?" she asked.

"Of course you can, you don't have to ask permission," I said.

"Good," she replied and started stroking.

I leaned in and kissed her neck while continuing to rub her pussy as she moaned. I moved my fingers up a tiny bit and started to rub her clit.

"Yes!" she moaned. "My clit is so sensitive."

I used my free hand to unbutton her blouse and moved my mouth down to her cleavage.

"Do I have permission to stop stroking for a minute?" she asked.

"You can do whatever you want, you don't have to ask permission, I'll tell you if I don't like it."

"Good," she said as she stopped stroking and removed her blouse and her bra before moving a hand back to my cock.

"Your tits are beautiful," I said before lowering my mouth to them, alternating between sucking the nipples into my mouth.

Her grip on my cock intensified and she started stroking harder.

I continued to rub her clit and suck on her tits as her moaning grew louder.

"My God you feel so good," she said. "Do I have permission to cum?"

"If I'm that good, you better cum," I said. "You don't need to ask."

"Oh God!" she shrieked as her body started to shake in orgasm. "Yes baby you feel so good."

"Tell me what you're thinking about when you stroke my cock."

"I'm imagining I'm on all fours and you're slamming into me hard and fast."

"Let go and get on all fours," I said.

With a grin she let go and quickly got on all fours.

I quickly got behind her and started slamming into her hard and fast like she wanted.

She felt so good and so tight and her moans of pleasure were growing louder with each stroke, that I didn't last more than a few minutes before pulling out and shooting my load all over her back and ass.

"Thank you sir," she said as she looked over her shoulder at me with a sexy smile.

"What's all this asking for permission and sir talk about?"

"I'm sorry. It's just that my last two boyfriends were very controlling, very dominant in telling me what to do. So when we started and you kept telling me I don't have to ask for permission I could just be me, it was relaxing. But at the end when you started to take charge, a switch in me flicked on and I got extremely turned on by it. So I'm not sure what it all means."

"It means we can have a lot of fun," I grinned.

We laid down next to each other with her head on my shoulder, one arm wrapped around her while the other was at her side so my hand could caress her face while I looked into those baby blues.

"So you really like it when the guy takes charge and tells you what to do?" I asked

"In some way, yes, I do," Cara replied. "I'm not a true sub, because I hate the spanking and pain that one ex tried using on me. But I like when a guy takes control in telling me what he wants."

"In that case, lick me clean and get me hard again because I want us to have a long passionate fuck," I said.

"Your wish is my command," Cara laughed as she slid down my body to my cock and started to lick and suck on it.

Her eyes were closed as she ran her tongue around the head.

"Open your eyes," I said as I put my hands on either side of her head. "I want to be able to see your eyes, your passion, as you lick me."

She opened her eyes and started tracing her tongue up and down the length of my shaft before lowering her head and taking all of it in her mouth, maintaining eye contact with me the whole time.

She lifted her head off my cock for a moment and smiled at me.

"How's that?" she asked.

"Wonderful, now alternate that with sucking on my balls while stroking me."

She moved her head so she could look up at me while licking and sucking my balls as her hand encased my cock and started stroking.

I was moaning in pleasure as I began to get hard. The look in her eyes, the sensation of her tongue and hand, and the sight of my cum on her back were all a major turn-on.

My moaning ignited something in her as she took my cock in her mouth and tickled my balls. She was bobbing up and down with an intensity I've never experienced before while rolling my balls in her fingers.

I was hard in no time from her treatment and I told her she had to stop.

"Why?" she asked. "Was I not pleasing you?"

"You were pleasing me too well and I have other things in mind. Now get on your back and spread your legs."

She eagerly complied, smiled, and motioned her finger in a 'come get me' motion.

I moved my face between her thighs and licked. Amazed at how wet she was and how sweet she tasted. I licked and sucked on her juices for several minutes, listening to her moans and sighs of pleasure.

"I'm getting close," she whimpered. "Do I have permission to cum?"

"Not until my cock is inside you," I replied. "I want to see if you can experience multiples by waiting."

"I think I can, but please hurry"

"Patience my dear," I said as I began to lick my way up her body. Running my tongue along her tout belly and then pausing to suck on her perfect breasts.

When I got to her face where we engaged in a passionate kiss, our mouths open and tongues intertwined.

I reached a hand down and lined my cock up with her wet pussy and pushed myself in.

Her warmth and folds enveloped my cock in a nice, tight fit. It was like heaven. I started to thrust a little harder and a little faster.

"That feels so good," she moaned. "Can I cum yet?"

"Not yet, wrap your legs around me."

She complied and I started slamming into her harder.

"Now?" she cried.

"Not yet, thrust your hips up to meet my thrusts."

When she started doing that it pushed me to the edge.

Our eyes were locked in the heat of passion.

"Almost there," I grunted.

"Now?" she whined.

"Now!" I said I pushed myself into her with one final thrust sending spurts of cum deep inside her.

"Oh God!" she cried as her body spasmed and her pussy clamped down tight on my cock.

"Please keep thrusting," she begged.

I started to thrust again with a slow steady stroke despite having already came.

"Yes, yes, yes," she cried. "I'm going to cum again."

With that she let out a loud satisfied moan.

I laid down on top of her, holding her tight, keeping my cock inside her pussy, looking into her eyes.

"That was amazing," I said breathing hard.

"That was one of the most intense orgasms I've ever felt," she said while holding me tight. "But why did you pull out the first time and stay inside me the second time?"

"I don't know," I replied. "The first time I think I was afraid of shooting inside you, it was just a wild spur of the moment thing. The second time we were more passionate and you felt so good I didn't want to pull out."

We kissed tenderly, agreeing we had to keep seeing each other.

She stayed over and we fell asleep in each other's arms. The next day we did it again in the shower and then later on the kitchen table. Each time I took charge of the action, telling her what to do.

We talked about it and she explained that she gets off on doing whatever I want to do, as long as I'm getting pleasure out of it. I told her that I'm similar, that I get off on hearing her orgasm from doing the things that she wants to do, but we haven't done that yet.

Over the next few months our friendship and love grew and the intensity of our sex remained high. Through lots of practice and lessons, the sex changed from me being in charge to a mutual affair where we would tell each other what we wanted.

One of my favorite times was the weekend before she stormed out of my life.

We were at a couples only resort and surprisingly the indoor Jacuzzi was empty. I was in my bathing suit and she was in a string bikini that left little to the imagination. I admired her ass as she climbed in before I walked over and turned on the timer. The jets started to flow and the water was bubbling, hiding everything beneath the surface.

I slid in next to her and we engaged in a tight embrace our tongues dancing in the other's mouth. Her hand was stroking me and I was fingering her. She began licking my neck and moaning softly while stroking my cock harder.

"I want this inside me and I don't care if we're caught or not," she said.

I let out a low growl as I moved her head so I could kiss her neck. I felt her hand come off my cock and she tugged my bathing suit down to my legs. Then she resumed her stroking. I reached underneath the water and undid the strings of her bikini bottom and removed it from her.

"I want you riding me," I said as I pulled her to me and forced her down onto my lap.

She got up slightly, grabbed my cock to reposition it before sliding herself onto it.

She started to slowly slide up and down on it, grinding her hips into my groin as she rode. She wrapped her arms around my neck and her tits were bouncing on the surface of the water as she rode.

Since they were on the surface and not above the surface I wasn't able to suck the nipples without getting a mouthful of water as well. So I didn't suck them.

As she rode me harder her tightness amazed me.

Soon we were both moaning loudly from the sensations of the jets and how good the fucking felt.

To her surprise and disappointment, I lifted her off me. But she smiled big when I stood her up, turned her around and entered her from behind, grabbing those perfect tits as I pumped into her.

The jets from the Jacuzzi had stopped and we were standing in the thigh-deep water fucking wildly, trying not to splash too much.

A few minutes later I leaned over and asked her if she wanted me to cum in her or on her.

"I'm thirsty cum in my mouth," she said as she turned around and sat down in front of me. She was looking up pleadingly with those baby blues, mouth open and tongue sticking out.

I frantically stroked my cock for the next 10-15 seconds before unleashing a torrent of cum. The first shot hit her face before she got her mouth over it. Her mouth and lips were wrapped tightly around my cock as I came, shooting five or six shots into her mouth, holding onto her head as I unloaded.

When I finished, with my bare ass and limp cock fully exposed we heard voices and the door to the pool / jacuzzi area open.

I quickly sat down and we snuggled close, trying to cover each other up.

A very attractive couple in their late 20s-early 30s walked in. I was playfully splashing some water onto Cara's face to get trying rid of the cum.

"The jets just shut off as you came in, could you save me the trip and turn them back on," I called out.

"Sure thing," the guy, whose name was Adam replied.

His girlfriend, Ava, came to join us in the Jacuzzi. After looking at us for a minute, an evil grin broke out on her face before Adam got the jets going again.

"I can see what you two have been doing and it looks like it was hot," she said.

"It was," I replied.

When Adam climbed in, Ava whispered something in his ear, likely about what we had been doing.

He grinned and asked if we were going to be getting out soon.

Simultaneously we replied "no"

Adam and Ava hugged and kissed for a minute.

"Honey, do you mind performing for an audience?" Adam asked.

"Not all at," Ava replied. "Maybe they'll stay and watch or join in."

With that Adam and Ava resumed making out and minutes later their swimsuits were on the pooldeck.

Adam was standing in front of Ava receiving a blowjob while Cara was stroking me beneath the surface and I was fingering her.

"My God, he's huge," Cara whispered to me. "I could never get all of that in my mouth and it would probably hurt like hell trying to take it in my pussy."

A few minutes later, Adam was sitting in the water and Ava was riding him hard.

I sat transfixed by the sight of Ava's CCs bouncing on the surface of the water.

Cara slapped me hard on the arm.

"Stop watching, they're distracted, it's our chance to get out of here," she said.

With that we quickly climbed out of the pool naked, grabbed our towels to cover up, held our swimsuits in hand and ran back through the hallways to the elevator.

In the elevator, I pushed her against a railing, opened her towel slightly and thrust into her for a couple of strokes until it stopped on our floor. Luckily there was nobody waiting to get on.

After we got off she said she wanted to race me back to the room.

As we ran back to the room our towels fell and we ran the last 50 feet or so naked.

I had the key in my hand and quickly opened the door.

We stumbled into the room and fell onto the bed. We spent the next 30 minutes frantically fucking each other.

Some cuddling was followed by a shower and dinner.

We returned to our room and spent the rest of the night passionately making love, not fucking, experiencing countless orgasms.

It was the greatest day and night of my life.

We had the perfect relationship, we were friends, we were in love with each other, and had great sex. I wouldn't dream of cheating on her and thought I never would. The only decision in my mind was when would be the right time to buy an engagement ring and pop the question.

However, that changed when a new executive came into the office. Jill Kelly was her name and insisted everyone call her Ms. Kelly. She was 5-foot-8, long blonde hair, light brown eyes, thin hips, 32E breasts, a shapely ass and well-toned legs. She liked to wear business skirts that showed off her stocking-covered legs and business jackets over loose blouses that showed off some cleavage. Her attire was a mix of professional and seductive. She was hot and I surprised myself by lusting after her at first sight. I can be a sucker for blondes and seeing a woman's legs in stockings is a turn-on. She was hotter than any porn star I jerked off to before meeting Cara. I would give anything to fuck her just once. On her second day she came into my office wanting to meet with me. Her first day had been filled with management meetings. She asked me if I could stand working for a take-charge woman after working with men for the last few years. I told her it shouldn't be a problem as long as we listened to and respected each other, like it's been with my previous supervisors.

"I'm the type of boss that likes employees to just do what I say without asking questions," she said. "Can you do that?"

"I'm sorry Ms. Kelly, but I can't. I've always viewed my position as one of being a co-operative, where I can offer advice and insight."

"I see you checking me out," she said, catching my eyes wandering over her body. "If you don't do what I say, when I say it, I'm going to file a sexual harassment suit against you. So what do you think of that and how I look."

"If I'm going to file sexual harassment against me, I might as well give you cause. In terms of looks, you're hotter than your porn star namesake. In terms of your work attitude, it sucks, but I'll comply as long as I agree with the order."

"Good," she said as she sat on the desk in front of me and spread her legs. "Your first order is to fuck me to orgasm."

I stood up and stared into her eyes.

"Ms. Kelly, I can't do that without asking two questions."

"What?" she asked annoyed. "You better get busy quickly."

"Sorry Ms. Kelly, I can't fuck on demand. The two questions are one, are you going to use your mouth or your hand to get me hard enough to fuck and two, condom or bareback?"

"Those are my kind of questions," she said with a laugh, grinning broadly. "Number one, get your pants down and your cock near my mouth, two, bareback."

I quickly pulled down my pants and boxers and moved my cock to her mouth. Although Cara's blowjobs are heavenly what Jill was doing was other-worldly.

She was giving me a prime blow job when I put my hands on her head.

"Do that again and you're fired," she said. "I'm the boss. You don't do anything without asking my permission first."

"I thought Bruce Springsteen was The Boss," I joked.

"Not funny," she said. "No cracking jokes during sex either. Are we clear?"

"Crystal," I said and thought about what Cara had said about her exes taking charge like this. I also realized I didn't like to be bossed around during sex. Then again I've never had a lust-fueled fuck like this one. There's always been some romantic connection when I've been with a woman, so this was something new.

In no time she had me as hard as steel.

Then she sat up on my desk and commanded me to get inside her.

I was inside her in one quick thrust.

"Put my legs on your shoulders and really power-slam me," she said.

I put her legs on my shoulders and started slamming into her hard and fast.

I pushed her onto her back so I could go even deeper and she moved her legs down around my waist and started moaning in pleasure. I had started to pant in pleasure from the intensity of the moment.

It was at this precise moment – balls-deep inside Jill with her legs wrapped around me - that my office door opened and Cara walked in wearing a long raincoat.

"Son of a bitch!" she shouted. "Who the hell is this?"

I pulled out and stumbled backwards, trying to cover myself.

"Cara, honey, it's my new boss," I said. "Jill meet my girlfriend Cara."

"I don't care who it is!" Jill shouted. "I didn't say you could stop fucking me."

"I can't do this," I said nervously. "I shouldn't have done this."

"You're right! You shouldn't have done this! I can't believe you'd fuck around behind my back! We're through!" Cara cried as she ran out the door.

I pulled up my boxers and pants and started running after Cara begging her to come back, leaving my office door open.

"Get back here now or you're fired!" Jill shouted.

I don't know what happened with Jill after that, if anyone saw her sprawled out my desk with her puffy pussy lips on full display or not.

I tried catching Cara but she beat me to the elevator and by the time I ran down the stairs I saw her car speeding away from the parking lot.