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Click here"Come on Dan, you know I've been carrying you for nearly a year." She was right, I could try to deny it, but we both knew she was right. My performance at work had fallen off the past year but Caroline had been there to cover for me. I never knew why, but it was quickly becoming very clear to me.
"I think you should take a seat Dan. We have business to discuss." Caroline reached over and pressed the button on her intercom, "Cindy, no disruptions please." That done, she returned her look to me. Caroline sat back in her leather chair, crossing her hands in front of her. "Dan, I know it's been a tough year."
I started to speak but she held up a finger to stop me. Recrossing her hands, she continued. "I know it's tough having your first child. I'm sure it's been chaotic for the past eight months, helping out with your daughter and running your group here." She paused for effect, I could only smile sheepishly. "And then to have Kristine cut you off from sex. That's tough on a man." She grinned wickedly.
I'm sure my face flushed, "Now wait Caroline ... what are you talking about?" I was shocked.
"Oh? Am I wrong? I understand it's been over a year since you and Kristine fucked. Are you going to deny it?" I wanted to ... I so wanted to, but I couldn't. She was right. Shortly after Kristine learned she was pregnant, we stopped having sex. And since the baby was born, I've asked many times but she has always told me no.
"Who told you those lies, Caroline?"
"Lies? Are you sure?" I sat in silence, not knowing what to say to her. "Well Dan, I'm tired of carrying you and getting nothing for my efforts. I have always found you to be an attractive man and now I would like to find out just how attractive." I looked across her desk with a look of amazement.
"What are you saying Caroline?"
"Dan ... don't be so silly. I know you think I'm an attractive woman. You've never wondered about me?"
I shifted in my seat, trying to mask my rising arousal. I've always thought Caroline to be an extremely sexy woman and had even fantasized a few times about her when Kristine would give me the cold shoulder and I needed relief.
Caroline stood and walked around her desk, never once looking at me. She walked to her office door and locked it. She next walked to the overstuffed leather couch and turned to face me. Unzipping her skirt, she pushed it over her hips and it slid to the floor. My mouth gaped. She stood six feet from me wearing her white blouse and a navy blue thong and heels. Caroline fell backwards into the couch. Smiling at me, "Now Dan, do be a dear and come over to the couch and eat my wet pussy."
I could feel myself perspiring all over my body. I thought of Kristine and my marriage. I thought of my job. And I thought of Caroline and the incredible body she was now showing me for the first time. "Caroline ... you may think I'm not happily married, but I am."
She raked her nails over her inner thighs. "Dan, I know you're not happily married. And honestly I really don't care. I do know you've only kept your job because of me. And without my continued support, you will lose your job. I'm giving you the opportunity to keep your well paying job and your happy marriage." She grinned as she said the word 'happy'. I do still love my wife, but I have become so frustrated as she has shut me out of parts of our former life. She was never a crazy person in bed, but we did have a pretty active sex life until ...
"So Dan, when I told you to eat my pussy it wasn't a question. Now crawl over here on your hands and knees and get between my thighs. I do hope you are good at eating pussy!" I was shaking. I was so aroused and scared at the same time. I had never really even contemplated cheating on Kristine. And now Caroline is holding my job over my head. I stood and took a step. "I said to crawl. You haven't earned the right to walk." Stunned, I dropped to my hands and knees in my suit. I crawled the six feet to the couch.
Caroline spread her legs wider, reached down and pulled her thong to one side of her pussy. She was nearly hairless, her lips engorged with blood from her arousal of being in control. Her scent was intoxicating. "I'm waiting." I moved forward and lightly brushed her lips with my tongue. She grabbed the back of my head and pressed my face to her crotch.
"Eat me, I said." I quickly flicked my tongue up and down her pussy and she relaxed her grip on my head allowing me to breathe. I soon got into a rhythm and began to enjoy myself. From her moaning, I could tell Caroline was pleased with me. Her pussy was so intoxicating and it had been so long since I'd been with a woman and I found myself quickly getting lost in her sex. My tongue stroked her pussy lips with intensity. I reached up and stroked her clitty, wagging my tongue from side to side across it.
Caroline began to wrap her thighs around my head as she neared her orgasm. She was moaning as my tongue slid between her lips. Then finally her body shuddered violently as Caroline's pussy covered my face with her cum. She tasted so good and sweet. My tongue licked at her juices wanting to drink them all down. As she caught her breath, she pushed me backwards onto the floor. Covering her pussy with the skant blue thong, she bent over and pulled her skirt up her long legs as she stood.
"I think it's time for you to go home to your wife now. We'll continue this another time." I lay on my back looking up at her. My erection was bulging my slacks. I was so aroused and confused and angry.
"Caroline, what do you mean?"
"You heard me. Now leave," as she walked to the door and unlocked it. I stumbled to my feet and adjusted my cock before exiting her office. She did hand me a tissue before I left and I hurriedly wiped my face before I met anyone in the halls. I hustled to my office, grabbed my car keys and left for the night.
I drove home in a daze. I still wasn't sure what had happened or how my life had changed. Fortunately Kristine was her quiet self and I quickly settled in front of the television and watched Monday Night Football with a couple beers.
#
The next morning I checked my voicemail as I rode up the elevator. The fourth and last message sent a chill down my spine. It was Cindy, Caroline's admin telling him that Caroline needed to see me as soon as I got in the office. I could feel my pits sweating. The elevator stopped on the ninth floor and I slowly walked down the hall. Cindy looked up, "She's expecting you." I tried to smile as I knocked on Caroline's door and walked into her office. Caroline was on the phone, but she motioned for me to close the door and take a seat. A couple minutes later she hung up the phone and smiled at me. "Good morning Dan. Sleep well?"
"What happened last night Caroline? I really don't understand."
"Well Dan, you gave me the best oral I've received in a long time." And then she let a devilish grin cross her face.
"Well thanks, I guess but that can't happen again. Kristine would kill me if she found out."
"That's great Dan but we've just begun to have fun." And with that she flipped something in a baggy across her desk at me. It contained a razor.
"I don't understand."
"I want you to shave." I rubbed my chin, it was smooth. "Uh-uh," as she pointed at my crotch.
"Now just wait. I can't do that. Kristine will wonder the hell I'm doing."
"From what I hear, she won't even notice. And if she does, you'll think of something."
"I can't, I won't!" I stood up to leave.
"Dan, this is not a choice. I will want to see proof my lunch time tomorrow. I'll have Cindy put something on the calendar for us. Have a nice day."
#
That evening, I stood naked in front of the mirror. I looked down at the black pubes covering my genitals and then at the razor in my hand. I knew this was the moment of truth. If I gave in to Caroline on this, I was hers and she knew it. As much as I wanted to resist, I feared for my job. And I was strangely aroused by all of this. I sprayed a blob of shaving cream into my hand and generously covered my genitals with the cream. Within five minutes time, I hopped in the shower to wash off the excess cream and let the hot water rush over my body. As I dried, I couldn't help but stare at my newly smooth crotch and saw not a hair on my sac.
I had an 11:30 meeting in Caroline's office waiting on my calendar when I arrived the next morning. I waited until ten minutes prior to accept the meeting but I knew all morning that I would go. Cindy was not at her desk so I breezed on in to Caroline's office with just a knock. As soon as I entered the office, Caroline told me to lock the door behind me if I was staying. As I closed the door, I realized Cindy was sitting on the leather couch. "Cindy's my assistant and I keep very few secrets from my assistant. That's part of what makes me so successful."
I looked over at Cindy and she merely smiled at me. She wore a short grey skirt, her legs crossed and dangling her left heel. "Caroline, I thought this was just between you and me."
"You thought wrong. And like I said, I keep few secrets from Cindy." As she said this, I looked over at Cindy just as she uncrossed her legs. She now sat on the couch with her already short skirt riding high up her thighs. My cock jumped as I could see her smoothness between her thighs.
Cindy spoke for the first time, "I understand you like the smooth look Dan. Is this true?"
"That's right Dan. I believe the point of this meeting was for you to show me you did your homework. I'm ready to see when you are ready to show."
I pulled my eyes from between Cindy's thighs long enough to look into Caroline's eyes. The combined effect of seeing Cindy and being in this position had me standing tall. I was embarrassed and couldn't wait to show myself all at the same time. I stood and unfastened my each button on my dress shirt, standing so both girls could see. Then my belt and the zipper. With that, I let my slacks drop to my ankles. Wearing basic whites, it was still obvious that I was aroused by my situation. I thought I could see a slight smile across Caroline's face. In one motion, I pulled the waistband away from my body and pushed my whites down my legs. The dark hair from my legs stopped at my upper thighs. Sparse dark hairs that trailed below my belly button stopped just below my tan line. All the space between was white and smooth.
Caroline stood up and walked around the desk. She stood between me and Cindy but was careful not to block her view. Her right hand reached out and cupped my smooth sac. Her fingers softly caressed my smooth sac sending shivers through my body. Her touch was electric to my skin. Caroline looked over her shoulder at Cindy, "I told you he would comply. Dan loves his job and he loved burying his face between my thighs and he doesn't want either to go away. And look how big he is, I bet he's at least eight inches!"
Her hand slowly circled my base and slid up my skin to the crown. Bending over, her tongue snaked past her lips and stroked my pee hole. I gasped at her touch. She worked her lips around my crown, just covering it but going no further. I could feel her lightly humming, causing sensations down my cock. I looked over at Cindy and she was touching herself between her thighs. Just as I thought she would continue, Caroline straightened up. "You can put that away now. I expect you to keep that area smooth at all times." I quickly pulled myself together and hurriedly dressed. "That's all for now. Our meeting for today is over." Cindy pulled down her skirt as I opened the door and left Caroline's office.
I continued to keep myself shaved and worked to improve my job for the next week without any 'extracurricular' meetings with Caroline. I so wanted her attention but was also afraid to say anything to her for fear of what might be next. That fear was realized that afternoon when it was mentioned in a meeting I'd need to take an overnight trip the following day to Chicago to see a client. And Caroline would go too for backup. I could feel my pits begin to sweat and the jump of excitement in my slacks. As the meeting broke up, Caroline walked by and said "I'll have Cindy take care of the travel arrangements. She'll let you know in an hour what time to be at the airport tomorrow. I do hope you've been diligent." I knew what she meant and I would be sure to shave in the morning.
#
We had a nine a.m. flight getting us to Chicago a little after two that afternoon. We didn't say much to one another either in the airport or the flight. Of course, Caroline was in First Class and I rode Coach. As we entered the hotel lobby, Caroline handed me a small package. "Open this when you get to your room. I'll expect you to be wearing it when I call you at 4."
My eyes opened wide in wonderment. She got checked in first so we rode separate elevators. I opened the door to my room and dropped my bags. Tearing open the small box, I wasn't quite sure what she had given me or how I was supposed to wear it. Inside was a photograph printed from a website. I looked at the picture in shock. It was a close-up photo of a cock and balls with a cock ring and ball separator. I looked at the clock, it was 3:45p.
Remembering what Caroline said, I quickly stripped off my clothes and stood there holding this device. The ring was shiny metal and all else was black leather with a number of snaps apparently for sizing. Looking again at the picture for guidance, I brought the ring to my tip and slid it over my flaccid member. It was difficult but I was able to finally get it snug against my body as the picture depicted. Looking at the clock, only three minutes, I fumbled with the leather straps to get it secured around my cock and separating my balls. Just looking down, I could feel the blood rushing. My silence was broken by the phone ringing. I expected to hear Caroline, but it was Cindy on the line.
"Hello Dan."
"Hello, Cindy?"
"Yes, silly. I trust you figured out how to wear your toy?" I could feel my body turn red with embarrassment. "It's a good thing Caroline had you shave. I understand those things can really pull the hairs. Caroline is expecting you in Suite 1517. Get dressed and go see her." I could hear her laughing as she hung up the phone. Pulling on my pants, it felt like the whole world would notice the lump in front. I so hoped no one would be on the elevator as I opened my door and left.
I knocked on the door and heard Caroline tell me it was open. "Caroline, this is crazy! Why are you doing this?" Looking down at my crotch, she reached out and could feel the straps and smiled.
"Well I must not be the only crazy one since you are following instructions. I must tell you that Cindy is so jealous that she is not here to see you." Again, I could feel my skin burning with embarrassment. "Do you know what this little toy is used for Dan?" I shook my head no. "Well get undressed and let me see if you did it right. Then I will tell you." I unbuttoned my shirt and kicked off my shoes and socks. And then stripping out of my pants and briefs, I stood before Caroline totally nude for the first time.
Her eyes opened wide as she saw me. By now, my anticipation had gotten the best of me and I was quite erect. My balls were separated by the quarter-inch wide strip of leather and bulging. "MMM, you are quite the healthy specimen." I tried to cover myself but she motioned for me to put my hands behind my back. Her fingernails lightly scratched my bulging left ball and my erection twitched causing her a giggle. "So Dan, this is a cock ring and separator. It's purpose is to confine you, allowing the blood to flow into your genitals but not allowing you 'satisfaction' without some amount of effort. It's designed to enhance the pleasure and make the pleasure last much longer." I looked down at myself and couldn't believe how hard I felt at this moment.
"I knew you would have a big cock. I bet you are at least eight inches long and so very thick. Trust me, you will love fucking with the ring on you. We need to fuck, I'm so turned on and I see you are as well. Now go get on the bed and wait for me." Caroline went into the bathroom and I pulled the covers back on the bed. She didn't keep me waiting long as I lay on the bed. Caroline emerged around the corner totally nude.
I could feel my heartbeat quicken, seeing her sexy shape for the first time. Her breasts were so big and full and pubes neatly shaved. She climbed on the bed and straddled my chest, sliding her pussy up over my chin. Quickly her musky pussy was pressed down firmly over my mouth. My tongue hungrily lapped at her pussy, sliding up and down the length as I struggled for air. I couldn't see anything, her body covering my face. I tried to quickly please her and I soon tasted her juices as my tongue probed her pussy. Without warning, Caroline lifted herself off my face and quickly positioned herself over my rock hard cock.
Holding it straight up with her left hand, she dropped her body around my cock. She slid all the way down, burying my thick cock in her moist pussy. She looked so damned good riding my cock. I found myself thrusting upwards to meet her body. She was right, my cock was so rigid and hard yet I felt like I couldn't cum if I my depended on it. Caroline bounced up and down on my cock. Moving around, having it rub different parts of her pussy as she came down on me. At one point, Caroline raised up so my cock was barely inserted in her pussy. She reached over and grabbed her cellphone. And took a picture of my cock in her pussy.
"What are you doing?"
"Cindy felt left out so I told her I'd send her a picture." Her fucking continued for ten minutes, then fifteen minutes. My body was covered in sweat, fucking this beauty on top of me. "On Danny, I'm ready to cum. You're sooo fucking good." She buried herself deep onto my cock and I could feel her muscles tense then relax as her body orgasmed on my cock. As she did, she bent over and crushed her lips to mine. Caroline lifted her sopping pussy from my cock and shifted around on the bed. Her lips surrounded my cock and slowly she began to suck her juices from my cock. Her fingers played with my throbbing balls, squeezing them lightly but feeling like she was using pliers. I moaned and groaned from her mouth on my cock. I so needed to cum and could feel it rising. Caroline could feel it to and replaced her mouth with her hand. She pumped me as a few small spurts of cum landed on my belly. I wanted to cum more, but the cock ring just wouldn't allow.
For the next two weeks, Caroline found ways to have us fuck three times each week. Each time she made me wear the cock ring. I loved the fucking, but was growing so frustrated not being able to cum with her. I began asking her about letting me cum but she would just dismiss me with a laugh. The next time we got together was a Monday afternoon. "Are you ready for me," Caroline asked.
I dropped my pants to show her the cock ring in place. When I did, she tossed me a condom. I caught it and looked at it. Given the past couple weeks, I didn't really think I needed it as it was so hard to cum. "I'll make you a deal. You can remove the cockring and wear the condom while fucking me." My eyes lit up and I quickly tried to get it off me as quickly as possible. "Not so fast. I said a deal."
She waited until I looked at her before she finished. "You can fuck me with the condom, but you'll have to drink the contents when you're finished."
"No Caroline! I can't do that. I won't do that."
"Then get on your back because I'm ready to fuck that big cock!" I stood there confused. My cock was throbbing, I wanted to cum inside her but this was just so weird. She quickly got naked, "I'm waiting," as she crawled onto the bed.
I couldn't get the cock ring off in my present state but I did unfasted the ball separator and remove it. I rolled the condom down onto my hairless cock. It had been years since I'd worn one of these. Caroline got on her back, "I want you to fuck me hard with that big cock." I knew this meant she wanted no foreplay and I moved between her thighs. The ribbed condom slid into her pussy and I began to fuck her like a crazy man from the start. My cock slid in and out as I lay on top of her. Our lips crushed together, our tongues dancing. My cock, hampered by the ring, but was still ready to blow. I could feel Caroline wrap her thighs around mine as my cock drilled her pussy. Soon we were both shaking, cumming nearly at the same time. I collapsed on top of her, my breathing heavy.