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Havana Club

By Strickland83 


Chapter 1 – A Dangerous Proposal

Boarding Pass

The desk phone rang. I knew the extension number by heart. It was Ross Crider, the company president. I picked up the handset and heard Ross’ strong voice.

“Chris, get up here right away. I have something to discuss with you.”

“I’ll be right there,” I answered. I hung up the phone and saved the spreadsheet I was working on. It wasn’t unusual to be called up to Ross’ office. The company, in spite of its size, was run on a very informal basis. I took the elevator two floors up to where the partners’ offices were located. Ross, being the company president, had his own secretary and reception area. I was used to walking right into his office. Today, his door was closed. That was unusual. It was a rare thing for him to close his door. I looked over at Agnes, his secretary.

“You can go right in. They’re expecting you,” Agnes told me with her usual smile.

I was curious, but not apprehensive. I tentatively opened the door as I knocked lightly. When Ross saw my head peaking in, he told me, “Come on in, Christopher. Have a seat.”

I entered, closing the door behind me. My boss, Mike, was seated on the sofa. One of the two chairs in front of the desk was occupied by William Hanes, the corporate attorney. Ross was directing me with his hand to the other chair. Now I was getting apprehensive. This did not look good. I was summoned to the president’s office to meet behind closed doors. My boss and the company attorney were waiting for me. I took my seat warily, sinking into the fabric but still remaining on the edge of the chair.

Ross leaned back in his maroon leather chair and looked at each of us in turn. “I want to make it clear right now that everything said from this point on is privileged information. Nothing said here is to be discussed with anyone except the people present. This is for the protection of everyone present.”

His words did nothing to comfort me. I was sure I was in big trouble. I just didn’t know what I had done. Instead of waiting for condemnation, I took the initiative.

“What did I do?” I asked in as level a tone as I could muster under the circumstances.

My question caught Ross off guard. He looked confused. “Do? You haven’t done anything wrong, if that is what you’re worried about.”

“Then what is he doing here?” I asked, pointing to William.

“Bill is here to answer any questions that come up. Let’s get right to it. We’ve called you here to make an offer. I realize this is going to catch you off guard, but it has to be done this way.”

“An offer?” I asked.

“Yes, an offer. Your record with the company is exemplary and we want to be sure you stay around. You are valuable to us and we want to use you to our greater advantage. We, I, have a special request to make of you. If you accept, there will be benefits. First, you will be groomed for a branch manager’s position.”

I relaxed. I hadn’t been called in because of something I had done wrong. I was being offered a promotion. A big one.

“We need someone to do the legwork in preparation for opening an office in a country we don’t currently serve.” Mike grunted at these words. An alarm went off in the back of my mind. Something wasn’t right with this. Ross continued. “I want to send you. There is a risk involved. I can’t deny that. You are the best man for the job. If you take the assignment, you’ll get the manager’s post when we can open that office. In addition, you’ll be offered a partnership when you return from the scouting trip.” Now something was really wrong. The risk would have to be substantial to merit such an offer. “In light of the risk, we’re going to do things a little differently. Your service will be considered in lieu of the price.” He saw the look of confusion on my face and explained with a smile. “We’re giving you the piece of the pie. You will buy in by doing this for us.”

“OK, what’s the risk? Where do I have to go? The Middle East? Haiti?” I couldn’t think of any other dangerous places where we didn’t have an office. The single word Ross spoke next marked the moment when everything changed. From that point on, things were never again the same.

Ross said, “Cuba.”

I was stunned. There was silence in the room. Nobody moved. Nobody said anything. This wasn’t a joke. They all looked too serious. I took a deep breath, then another. The sound of my breathing seemed amplified because of the silence.

“You want me to go to Cuba?” I asked, unsure I had heard him correctly.

“Yes. You’re perfect. You speak the language. No close family to ask questions, you have experience in –“

I cut him off. “You can’t just go to Cuba. It’s illegal, isn’t it?”

Ross looked to my left and asked, “Bill?”

William spoke up for the first time since I entered the room. “Technically, it’s not against the law to enter Cuba. It is illegal to spend any money there. Unless you have a license from the Commerce Department, or have all your expenses paid by a foreign national, then engaging in any monetary transaction is a crime.”

“So I just don’t buy anything. Is that it?”

“It’s not that simple,” William continued. “You have to eat. You have to rent a hotel room. You have to pay the exit tax to leave the country. You can’t go to Cuba without spending any money. That puts you in violation of the Trading With the Enemy Act.”

I asked the obvious question but I already knew the answer. We wouldn’t be having this conversation otherwise. “Do we have a license?”

“No,” Ross answered. “We made some confidential inquiries. We were told in no uncertain terms that licenses were not issued by this administration for the purposes we had in mind. No license, period. So you’ll have to sneak into the country.”

“Sneak?” What the hell did that mean?

“Yes, sneak. You can enter covertly through Mexico, posing as a tourist. The Cubans will let you in and you can do the research. At the end of the week, you return to Mexico, and then reenter the U.S. posing as any other tourist returning from a week in Cancun.”

“Tell me about this ‘risk’,” I asked, not feeling any more relaxed.

William took over again. “It isn’t all that risky.” Mike snorted again. He must be there to look out for my interests … and he didn’t sound like he had much confidence in the plan. “As long as the U.S. government doesn’t find out about your little trip, you come home without incident.”

“And if they do find out?” I wasn’t sure I wanted to know the answer.

“They won’t,” Ross said.

William continued. “If they would – and it is very unlikely they will – then you could be fined or possibly even arrested.” His voice trailed off as he said the last part.

“Arrested?!! I don’t like the sound of this.”

Ross leaned forward in his chair. “Bill can explain it better, but it is easy to get in and out of Cuba without being noticed.”

“You want me to sneak in! Don’t people try that all the time and fail?”

William spoke up again. “People have trouble sneaking out. The Cuban government will welcome you. They’ll even issue you a visa. They want American tourists to come in and spend dollars.”

“And what about the Cuban stamp on my passport? Do I just hope customs won’t look at that?” This was sounding like a really bad idea.

“They won’t stamp your passport.” William was trying to sound calm, but I could hear a note of alarm in his voice – not a good sign. “Our government issues about 20,000 licenses a year for citizens to enter Cuba legally. The Cuban government says they admit over 200,000 American citizens annually. A lot of people are doing this.”

“So, if it is so easy, what is this risk you keep referring to?” I wasn’t convinced.

Ross again took the floor. “First, you have to do this quietly. Nobody knows where you’re really going. Nobody. Second, no paper trail. Everything is done with cash. Finally, you must not get into any trouble in Cuba. No run-ins with the police or the government at all. You have to be very careful. If you get into trouble, you don’t want to call in the U.S. government for help. If our government even finds out you’re there, when you do get out, you can be arrested at the border.” Now, Ross looked me right in the eye. His expression was the most serious I have ever seen him use. “I give you my personal word. If anything goes wrong, I will personally go down there and get you out. We won’t leave you there. Whatever it takes, you’re coming home.”

That made me feel a little better. Still, there were risks. “So I slip into Cuba and look into opening an office there. Then I get back home. For this, I get to be a partner? The reward is big. Why is this so important, and why me?”

Ross answered my questions. “Cuba is an untapped market. We want to be postured to move in when things change. Castro is old. He has to die someday. In the meantime, there is a lot of pressure on the President to change our policy towards Cuba. Either way, soon it will be possible to do business there. We want to walk in with the groundwork already done. We want to setup shop – fast. Cuba has potential as a vacation spot, exports of agricultural commodities, cigars, music. Cuba is a market that is waiting to explode. In return, they need just about everything. That’s the way we see it. You will be our eyes and ears. You will find out for certain. Why you? Because, as I started to say before, you speak the language. You can make a covert trip because you don’t have any close ties to ask questions. You already do a lot of business in the Caribbean basin so you know what to look for. You really are the best man for the job. You are our best option for heading up the Cuban office. When things open up, we want you on our side, so we’re making you a partner. Do the job. Be careful. In a week, you’ll have earned your share.”

Mike spoke up for the first time. I jumped when I heard his voice. I had forgotten he was still back there on the sofa. “If he doesn’t get caught. He’s taking a hell of a risk. He could face a big fine, loss of his passport, or even jail time. He –“

Bill cut him off. “No, jail time is only for repeat offenders who are trafficking in Cuban goods.”

Mike broke in with, “Let me finish. He can never get a government clearance. Do you realize how that will look on your record, Chris? Going into Cuba without permission. For God’s sake, what if you do something, anything, that gets you arrested? You might serve years in a Cuban prison, then face jail time here when you get back. I think this is too risky. There has to be another way.”

“There is no other way,” Ross responded. “We’ve looked into this as well as we can from the outside. We need someone on the street. Someone we can trust to do a good job. Chris is the man for the job.” Now Ross shifted his gaze from Mike directly to me. “How about it, Chris? Will you do it?”

My mind was awash with the possibilities. If I got caught, I could lose everything – even my freedom. If I pulled it off, I would be a partner. My future would be set. “You made an attractive offer. I need some time to think about it. Can I give you an answer in a day or two?”

“Sure,” Ross smiled. “Think it over. Feel free to talk to any of us about it. Just remember, talk to no one else. This is mostly for your protection. Let us know what you want to do. You’re a valued employee and we want you on our team, whether or not you make the trip.”

“OK, I’ll think about it.” I stood. I felt a little unsteady. So much had changed since I sat down.

Ross stood and walked around his desk to clap me on the back. “I’ll be waiting for your answer.”

I nodded and headed out the door. Agnes looked up as I closed the door behind me. She looked concerned.

“Christopher, are you alright? You look a little pale.”

“I’m fine. I just… I need some time to think, that’s all.” I hurriedly left, returning to my office. I sat down and thought. I couldn’t even talk this over with anyone. This was a once in a lifetime chance. I knew I should take it, in spite of the risks. It was a great opportunity, not just the promotion but the experience in Cuba as well. I would have first hand knowledge. This would help with my dealings in the other markets in that region. While I was thinking it over, Eudora chimed. I had a new e-mail. I pulled up the window and saw it was from Ellen. She was inviting me for dinner tonight. She had been trying to get me to see her for a few weeks. She was cute – she just wasn’t someone I wanted to have a relationship with. I hadn’t been able to find anyone I wanted to have a relationship with for a long time. I didn’t want to take a chance. Thinking about the situation with Ellen made me think again of Ross’ offer. It was a once in a lifetime opportunity. Sure there was risk, but the rewards were immense. If I didn’t take this chance, would there ever be another? If I didn’t take this chance, would I spend the rest of my life wondering What if? That did it. My mind was made up. I bolted from my chair and headed for the elevator. I punched the up button and it lit up. I was hoping the elevator got there before I changed my mind. I didn’t want to back down. I wanted to do this. I needed to do this.

After what seemed hours, the door opened. I got in and pushed the button for Ross’ floor. The doors closed and I felt that heavy sensation as the car moved upward. The only other person in the elevator was Hank Jenkins. He was babbling about the basketball game some of us had gone to see last week. I tried to be polite but I am sure it was obvious I was preoccupied. I guess it was good he was there because he kept me from dwelling on what I was about to do. I felt the elevator stop. The door opened. The desk where Agnes sat was opposite. I got out and marched to the office door, ignoring Agnes entirely. This was not like me. I always at least acknowledged her with a smile. I stood in the door to Ross’ office, my left hand on the doorframe. Ross was sitting behind his desk, reading a paper. I took a deep breath.

“I’ll do it,” I announced.

Ross looked up, saw it was me and broke into a grin. He quickly got up from his chair and walked around the desk to where I was still standing, still being held up by the doorframe. He put his arm around me and pulled me into the office, closing the door as he said, “Come in, Chris. Let’s talk about this, partner.”

There. I had done it. I had committed myself. Maybe I needed to be committed. Ross didn’t give me time to dwell on the darker aspects of what I had just done. He sat me down on his sofa and sat next to me.

“Are you sure about this?” he asked me.

“Yeah, I’m in. When do I do this?” I hoped I didn’t sound as nervous as I felt.

“I’d like for it to be as soon as possible. There are a few external forces we can’t control. First, our current president has been hinting he might start seriously enforcing the travel ban. We need to get you back before that happens. Then, and this is the main reason we’re doing this now, there are rumors that Castro is sick. He might have Parkinson’s Disease or other problems. Once he dies, the game changes. There will be a power struggle. Who comes out on top can determine if the country opens up to us or not. I’d really like our base to be established before that happens – so we can be first in. Do you follow me?”

“Sure, Ross. So, when do I go?”

“How about Friday?”

I stared at him. This Friday? He saw my reaction and countered with, “Is that too soon? Do you need more time?”

“No, I might as well get this over with. I’m just surprised. I thought it would take more time to set it up.”

“We need to start briefing you with the procedures. Whatever you’re working on, pass it on to someone else. For the rest of the week, you’re focusing exclusively on this project. Oh, and no one – I mean no one at all – is to know where you’re going. We’ll arrange a cover story for the other employees. It would be best that you don’t talk about this, even when you get back.”

I noticed that he said “when” and not “if”. That served to reassure me a little.

“Bill has already been doing some research on how to do this.” Ross, as if just realizing that I had agreed, reached over the arm of the sofa to the telephone on the end table. He hit a button, then said into the receiver, “Agnes, I need a first class ticket for a flight to Cancun on Friday morning. No, it’s for Christopher. Returning the next Saturday. Call me back when you get it setup.” He hung up, then hit another button. “Bill, he’s agreed to do it. Bring the file in here so we can start working on strategy.” He hung up and turned back to me. “You’re flying first class because you’ll be hassled less that way. It helps to get you through customs easier.”

“Thanks,” I said with a lump in my throat. I was still nervous. I had just agreed to commit a federal crime.

William Hanes came right over, carrying a thick brown folder. We spent the rest of the day sorting through all the material that had been collected. Agnes picked up lunch and we ate in the office. The door had stayed closed the entire time, except for Agnes bringing in lunch. I was somewhat nervous about the whole idea. It seemed that I made more trips to the bathroom than usual. Ross made his executive restroom available to us. I guess that is one of the privileges of becoming a partner. I just hoped I returned and got to be a partner a little longer than the rest of the week.

During the afternoon, Agnes called in to say my ticket had been delivered by a courier. Now it was official. I was going to Cuba. William had done a lot of preliminary research. There were basically two sets of documents. One was how to safely get in and out of Cuba. The other was about doing business there. We focused the first day on how to get me in and out. Maybe that was to relieve my stress level. To his credit, Ross seemed as anxious as I was about my safe passage.

By the end of the day, the plan for my arrival was set. I would meet a travel agent in a village south of Cancun. He would make all the Cuban travel arrangements. At the end of the day, William pulled a battered copy of Frommer’s Cuba from the folder.

“I found this at a used bookstore. I didn’t know they made one, and it’s a few years old. Still, it’s a pretty good guide. Take it with you.”

I leafed through it. There really was a guidebook for Cuba. I planned to spend a lot of time reading it over the next few days. I had to keep it concealed. I felt like Winston Smith in 1984, carrying The Book in my briefcase.

By 4:30, we were worn out. The stress was taking its toll. Ross told us to call it quits and start again in the morning. I went back to my office to turn off my computer. When I sat in my chair, I saw the e-mail from Ellen. I decided that I shouldn’t pass up any opportunities that presented themselves. If things went badly, she might be the last woman I would be with for a long time. I called Ellen at her office. She was delighted to hear from me. I asked if she wanted to get together that night. She invited me over for dinner and a movie. I told her that it sounded great and I would be over after I showered and changed. With that, I turned off my computer and left the office.

At home, I cleaned up and dressed very casually. With any luck, I wouldn’t be back until morning. I was out of the house and on my way to Ellen’s place in about half an hour.

I pulled into the parking lot of Ellen’s apartment building and parked next to her car. The night was warm and muggy. The crickets were singing as I walked to her door. I didn’t feel like singing. I still felt like I was on my way to my execution. First things first – I was going to enjoy this. After all, it might be my last. No regrets. Onward and upward from here. I stretched out my hand and rang the doorbell.

It took Ellen a minute to get to the door. She opened the door, looking lovely in a blouse and jeans. The blouse was low cut (that looked promising). She hugged me as I stepped in. I had been here before. We had dated in the past, but nothing serious had developed. At this point, I felt I had nothing to lose. After shutting the door, she led me to the kitchen where she was finishing a meal. She confessed that she had picked up most of it at the market.

“That’s fine. I’m amazed you had time to do any of this when I called you so late,” I reassured her.

“I was so happy you called. I’ve wanted to get together with you for so long. You sounded like you had a rough day at the office,” she said.

“I did. We’re working on plans for a new office,” I half lied.

“Do you think you’ll get a shot at the manager’s post?”

“Maybe. There have been a lot of hints.” That part wasn’t a lie.

“I hope you get it. You deserve it. You’ve worked hard for it. Do you think you will have to move?”

“I don’t know yet. There are a lot of details to work out before we get to that point,” I answered.

By then, dinner was ready. We dined by candlelight. She looked radiant in the softly glowing light of the candles and I told her so. She accepted the compliment graciously. After dinner, we took our wine glasses into her living room. She had picked up a DVD of Like Water for Chocolate.

“I know you’re good at Spanish. Maybe you can explain the nuances to me,” she suggested. I smiled.

We started watching the movie. She curled up next to me and I put my arm around her. She smelled wonderful. She always smells wonderful. It’s not just perfume. Her shampoo, her clothes, they all smell wonderful. I hoped to find out if she smelled that nice beneath her clothes. I bet even her sheets smelled nice. Before long, she laid her head on my shoulder. I was getting more interested in her than in the movie. By the time Gertrudis took her shower, I was ready to see more of Ellen. She was into the movie, but her body language indicated she was being swept up by the romance. I kissed the top of her head. She moaned softly and lifted her face up to mine. I leaned down and kissed her lightly on the lips. She put her arm around my neck and pulled me down. As we kissed again, I felt her tongue on my lips. I opened my mouth and our tongues met. As we parted to take a collective deep breath, I glanced at the screen and saw Gertrudis being carried away naked by the soldier on horseback.

“Mmm, I’d like to do that to you,” I suggested.

“That’s so romantic,” she said in a dreamy kind of way. She looked from the screen to me as if coming to a decision. Then, “Do it.” It wasn’t a command or a request. It was simply a statement. I wasn’t going to pass up an opportunity like that.

Ellen stood up in front of me and began undressing. I watched, mesmerized, as her blouse drifted to the floor, followed by her jeans, then her bra. By the time her panties softly settled to the top of the pile on the floor, the movie was forgotten in the background. Ellen was backlit by the screen as if she was glowing. She took two steps back and looked at me suggestively. I stood and took her in my arms. I kissed her deeply, inhaling her scent through my nose. She pressed her body against mine in such a sensuous way that I was sorry I was still wearing my clothes. I longed to feel her skin against mine. I reached down and put my right arm behind her knees, my left behind her neck, and easily lifted her slim body off the floor. As I carried her in my arms to the bedroom, she kissed me. I could see her nipples becoming even more erect. I hit the light switch with my elbow as we entered the bedroom. I bent over the mattress and delicately set her down. Her slight weight barely dented the soft surface. Her eyes lit up as an idea was suddenly born.

“Wait here,” she said. “I’m going to get the candles. Take off your clothes and wait for me on the bed.” With that, she got up and padded off to the kitchen. I undressed and slid onto the sheets to await her return. I was hard, anticipating the feel of her body. I heard her returning. Just before she entered the room, she reached in with one hand and turned off the light. Instantly, the room was illuminated by an orange glow as she entered with two candles in each hand. She set them down on the dresser and nightstands, surrounding the bed with warm light. Her naked body was so erotic in that light. Her dark blonde pubic hair looked darker in the light, but still it was apparent she was a natural blonde. Her breasts rose and fell as she took in deep breaths. I was breathing heavy as well. We were awash in anticipation.

Just before she got into bed, I noticed a slow trickle of fluid down the upper part of her left thigh. She was so wet for me that her juices could not be contained by her lips. I was mesmerized by the sight.

Ellen broke the silence as softly as she could. “You are so excited that I can see a trickle of your precum flowing from the end of your dick.” Her whisper was as if she was breathing instead of speaking the words. I just smiled. We wanted each other so badly.

She bent one knee and crawled onto the bed, on top of me. As her body grazed across mine, she bent my dick back to my stomach - first with her mouth, then her neck, then my dick brushed the skin between her tits. Next, the smooth skin of her stomach rubbed me. Finally, her soft pubic hair brushed across the center of my excitement, signaling the completion of her movement. She was lying on top of me now, kissing me deeply. I encircled her slender waist with my arms, letting them wander of their own accord down to her ass. As we kissed, my hands roamed down to the tops of her thighs, up across her ass and lower back, then back down again. I reveled in the feel of her warm skin. Between kisses, I drank in the vision of her face illuminated by the soft glow of the candles.

After six or seven kisses, she smiled a little broader as if she had a secret. I felt her body begin to slide down mine. She didn’t get up and move down. She slid across me, her nipples grazing my skin, her mouth kissing its way down my torso. All the while, she maintained eye contact. When she arrived at my dick, she looked at me with an impish smile. Then her mouth gingerly kissed the head and shaft. I was leaking so much precum that strands of fluid were connecting to her lips as she moved back from each kiss. The strands shined in the candlelight. My dick was starting to throb. I couldn’t take too much of this and she knew it. Once she had bathed the entire surface of my dick with her lips, she started at the base and ran her wet tongue in long strokes to the tip. She only licked upward. As she pulled away from the tip to move back to the base, strands of the mixture of her saliva and my precum remained connected for a moment before breaking away. All this was revealed in the golden glow of the candles. Only when she had completed licking all around me did she return to the tip. Planting an open-mouthed kiss on the head, her mouth opened as if in a French kiss. Her mouth descended, taking my dick into her. The feeling of warm wetness was all encompassing. I knew I was going to cum in her mouth. There was no avoiding it. She watched me as her mouth moved down over me. Her cheeks pulled in as she sucked on the upstroke. I felt powerless to break the eye contact. I watched as I was helplessly drawn to my impending climax.

When I felt my dick start to throb to announce the arrival of my orgasm, I saw her eyebrows move upward slightly in sync with the ends of her mouth. She was smiling, but my girth prevented her face from completing the gesture. I rested my hands lightly on her head, then ran one hand down her cheek. I pushed my hips upward as I felt the first contraction. We looked into each other’s eyes as my sperm was forcefully splashed into her mouth, the invasion aided by her suction. I saw her neck delicately swallowing, my erection filling her mouth too much for there to be space to contain my ejaculate. Once my orgasm was complete, she lifted her mouth gently off me, not wanting to over stimulate me when I was most sensitive. We didn’t say a word, just smiled at each other in the light of the candles. She again slid up my body. As she approached my face, I could smell my sperm on her breath. When she leaned to kiss me, I didn’t resist. I was too captivated by her spell to resist tasting my cum in her mouth. We kissed, my tongue exploring her mouth even as I tasted myself. It wasn’t a turnoff. Instead, it added to the sensuality, reminding me of what I had just done in her mouth.

As the kiss broke, I slowly rolled her onto her back. “I’m going to return the favor,” I breathed. “Then, after you’ve cum and I’m hard again, I’m going to fill you with my hardness.” She gave a little moan. I kissed my way down her body, the sensitive spot below her ear, her neck, the top of her shoulder, each of her breasts (holding each nipple in my lips as I pulled away, watching the base of each nipple stretch), her stomach, exploring her navel with my tongue, until I was brushing my face against the hair around her pussy. Her hair was so soft, only slightly abrasive because of the curls. She was wet, her juices flowing past her lips to start forming a small puddle on the sheet beneath her. I could smell her before I could see the gloss on the bottom of her lips. Pushing my nose through her hair, I enjoyed her smell. As I pushed lower, I extended my tongue, parting the hair that grew on her lips. My tongue ran along her slit, wet with her arousal. I tasted her here first as I ran my tongue along her outer lips. Finally, I settled between her legs as she eagerly spread them to make room for me. I reached down to each knee in turn, dragging my tongue along the smooth inside of each thigh as I traced a wet path back to her pussy. Finally, I used the fingers of each hand to gingerly open her outer lips, revealing her pink wetness. I could see her hole oozing her special wetness. I also easily found her clit, erect now and sticking out from under its hood. I extended my tongue to touch the tip to her clit. She jumped, her hips trying to pull away from the sudden touch. I extended my tongue to remake the contact, now sliding my tongue across the sensitive nub of flesh. She pushed her hips against my mouth this time. I looked up through her bush to her face. She was watching me and it seemed that she was not even breathing. After a minute, I finally saw her breasts rise and fall as she took a breath. I slid my tongue lower to her opening and she took a deeper breath. I lowered my mouth further. I rolled my tongue to make it stiff and pushed it inside her. I was rewarded with a big taste of her juices. The smell and taste were overpowering. I breathed into her pussy and she let a moan escape her lips. I began licking her pussy in earnest. The middle finger of my right hand entered her fully. When it pulled out and reentered, it was joined by my index finger. On the next trip, my ring finger joined in. Each time, her moan was louder as I stretched her and rubbed against the sensitive ridges of her entrance. Her eyes were closed now and her hands were clasping her nipples. I watched as her first orgasm of the evening washed across her face. Her legs closed against my face. I concentrated now on her clit, my fingers caressing her from the inside as well. I felt her hips lift off the bed and she gave a moan that became a scream. I pushed all three fingers inside her as far as they would go and held them there, feeling her pussy contract around them as she came.

When she could open her eyes, I moved off her cunt, gently removing my fingers from her slick hole. I rested my chin on her mound, her soft hair around my chin. I smiled and she returned the gesture.

“Oh, wow. That was so incredible,” she said after swallowing hard and licking her lips.

“I was just returning the favor,” I said slowly with a grin.

She reached down and pulled my face to hers. She kissed me, tasting herself in my mouth. Then, she held my face in her hands as she licked her juices from my cheeks. When she had finished, she kissed me again.

“I’m hard again,” I said loudly.

She smiled a little broader. “Is that a threat?” she asked.

“I’m just trying to warn your neighbors that it’s going to get noisy.”

“You’re so smug when you say that. Do you really think you can make me scream?” she asked.

“I didn’t do so badly a moment ago – and that was with only a few fingers and a tongue. I’m saving the most devastating weapon for last.”

“Devastate me,” she offered as my sides felt her legs spread further.

I lifted myself up, looking down at her pussy. I guided my dick to her slit, using my hand to rub up and down her lips and spread her ample moisture. She was starting to softly moan as I dragged the head of my dick across her sensitive flesh. It looked as if she was just about to protest having to wait as I positioned my dick at her portal and pushed. She was so wet by now that there was almost no resistance. She was tight. It was only because she was so slick that I easily slipped through the tightness to stretch her enough to admit my cock. In one stroke, I felt the hair at the base of my shaft pressing against her lips. She gasped.

I lay on top of her, feeling her hard nipples against my chest.

“You’re so big,” she breathed.

“You made me so hard. I want you so bad,” I explained.

“Take me,” she offered.

With that, I pulled my dick out until only the head was still captured by her lips, then slowly but firmly pushed my way in again. Seeing the look of ecstasy on her face, I knew she was able to take more stimulation. I knelt at the juncture of her thighs, still embedded in her. I lifted her legs and placed them over my shoulders. Then, I leaned forward until my chest was against hers, separated only by her thighs. I pushed harder and my dick penetrated her as far as was possible.

“Oof,” she grunted. Then, catching her breath, she softly spoke. “I think I can feel your dick pressing against my cervix.”

I tried to press harder, but I couldn’t go any further. Instead, I pulled out fast and pushed in just as fast. My flank thumped against her pussy. She let out a small yelp.

“Am I hurting you?” I asked.

“I don’t think so,” she assured me.

I did it again.

“No, that doesn’t hurt – yet. Don’t stop,” she urged.

I complied. With each thrust, her yelps became a little louder. Before they became full-fledged screams, I needed to stretch my cramping leg muscles. I moved up again and let her legs slide off my shoulders. She took a deep breath and focused her eyes on me.

“Need a break?” she asked. “I can get on top.”

“Sure,” I said, sliding around to the pillow next to hers. She deftly mounted me, sinking that blonde-haired snatch onto my shaft. Now it was my turn to gasp as she forcefully impaled herself on me. She was truly a vision of loveliness, the bouncing of her breasts delicately illuminated by the candles. I watched her face as she concentrated, now fully in control. I intended to lie there and rest, but my body reacted to the stimulation of her pussy and began thrusting up to meet her downward thrusts. The bed began issuing forth rhythmic squeaks as our pounding intensified. Tiny beads of perspiration were forming on her chest. I could feel that I was sweating as well, making the sheet beneath my ass damp. Out of the corner of my eye I could see the alarm clock on the nightstand. I knew that I would last a long time after that blowjob she just gave me. Ellen was athletic so it would be a race to see who gave in first. We both made modifications to the position as time passed – she adjusting the angle of her hips to rub her clit against the base of my dick or sitting upright and rubbing her clit with two fingers, me leaning up on my arms to capture one or the other nipple in my lips, or reclining to watch the vision of her riding me as I let her nipples rub up and down against the palms of my hands. Not wanting to relinquish the position of control, Ellen even got up and turned around for awhile, facing my feet as she rode me. In this position, I could fondle the globes of her ass. If I sat up a little, I could just about reach around her waist and let my fingers explore the top of her hairy slit to search for her clit. She turned back around and I could see sweat on her temples now. Her hair was getting damp. I looked at the clock. We had been in this position for twenty minutes.

“You must need a break by now. How about a change?” I suggested.

It was apparent she wanted to continue, but she was getting tired. She managed to pant out, “OK… doggy?”

I nodded. She lifted off me. The hair around the base of my dick was saturated with her juices. She leaned over and moved onto all fours. I got up on my knees and thrust my erection through her slippery lips, seating myself in one stroke. She leaned forward on her elbows as I started thrusting. I reached around to encircle her waist, then slid my hands up her body until I gripped a breast in each hand as a handle. I squeezed the nipples to put extra pressure there as our thrusting caused me to tug at her sensitive cones. She was beyond moaning now. She was screaming. In this position, her entrance was putting pressure on the bottom of my dick and I knew I couldn’t last much longer. I was ready to cum. I was getting tired. I was also worried that she was getting sore. I thrust harder to push her over the edge. She lost her balance on her elbows and fell forward, now fully face down on the mattress. I moved a little further over her. I put both hands on her ass cheeks to rest my weight there. Now my dick felt as if it was going straight down into her body. I knew the head was rubbing against her G spot. She couldn’t speak intelligibly now. Her words were muffled moans verging on screams. Regardless, I could tell she was enjoying this as much as I was. I crossed the point of no return and thrust into her particularly hard. My hands tensed, the fingertips digging into her ass. I felt myself erupting inside her, adding to the already ample slickness. I shot five or six spurts really hard, then the tension eased and I leaned more over her. The eruption of sperm inside Ellen’s body was now a dribble as I moved to rest on her back, my softening dick sliding out of her channel. She let out a slow groan as I slid free of her confines. I held my dick against her pussy as I rested my face against the back of her neck. I could feel that her hair was wet with sweat. I could also feel a flood of warm fluid bathing my dick. I knew it was the combination of lubrication my dick had held inside her pussy mixed with the sperm I shot in her. We were making one enormous wet spot on the sheet. I knew she would be feeling it as well, against her front. Neither of us moved, whether because we were basking in the glow of what we had just done, or out of sheer exhaustion. The only sound in the room was our heavy panting as we each caught our breath.

After a few minutes of this, I rolled off her. I didn’t want to move away from her warm flesh, but I knew she must be uncomfortable with my weight against her. I slid to the side, one leg still between hers, an arm around her waist, and my side against hers. I turned my head to her and kissed her cheek, right in front of her ear. She shivered.

“Ooh, you know I love that. I’m so sensitive there,” she said in a voice that told me she still wasn’t fully there.

“I’m sure you’re sensitive in a lot of places right now,” I responded. She gave a happy grunt of agreement.

I held her like that for a time. Her heart was still beating so hard that I could feel it with my arm on her back. At last, she turned over. The hair around her pussy was matted with our juices. I could see that she had been lying in a wet spot. It must have been a puddle at first, until the bedding soaked it up. She looked at me sleepily and grinned. I smiled back. Her smile turned to a frown.

“I need to pee, but I don’t want to get up.”

“I’ll help you,” I offered.

“Ordinarily, I’d be too embarrassed to accept, but I don’t think I can make it there without your help.”

I helped her into a sitting position on the side of the bed, then helped her stand, supporting her with my arm around her waist and her arm around my shoulder. Together, we shuffled to the bathroom. I eased her onto the toilet seat. I turned to leave.

“Stay,” she said. “You’ve come this far with me. I don’t have any more secrets.”

We both smiled. I leaned against the lavatory, the porcelain feeling cold against my bare butt. She looked at me as she peed. When she was done, I helped her back to bed.

She spoke. “I am going to be so sore tomorrow. Stay here with me. We’ll both call in sick and spend the day in bed.”

“I can’t,” I told her. “I have an important meeting tomorrow that I can’t miss.” She pouted. “I really can’t miss it. Sorry.”

“OK,” she said as her pout softened. “Then come back tomorrow night.”

“You’re already sore. I’ll do real damage.”

“No, you won’t. I’ll just walk funny tomorrow, then I’ll call in sick the next day to rest.”

“I’ll spend the night. Maybe you’ll be up to another time in the morning.”

“You can have me now, but you’ll have to do all the work. I’m worn out.”

“That’s alright. Rest now. Maybe I’ll wake you up during the night.” With that, I got up and blew out the candles. In the darkness, I pulled the covers over her and crawled into bed next to her. “I’m tired, too. Later, we’ll do it again.”

We were both asleep in minutes.

It was early morning when I woke. She was still face down next to me, breathing deeply in the sleep of the fully sated. The sun had not yet risen. I had a morning erection and I wanted to use it. I felt a little guilty because I knew her pussy would be sore after last night’s marathon session, but not that guilty. I pulled back the covers and gently rolled Ellen over until she was on her back, then spread her legs. She looked so inviting, even though she was unconscious. I slid one, then two fingers into her. She was very wet, lubricated from the mixture of her juices and my sperm. I leaned forward and tasted her pussy. When my tongue passed over her clit, she gave a slight moan, but it didn’t disturb her sleep. I grinned, thinking about what I was going to do. I crawled over her, supporting myself on my arms and positioned my dick at the entrance of her pussy. I used one hand to guide the head into her and very slowly worked my way inside. I was fully seated and she was still asleep. This felt so naughty, like I was stealing something from her. I wanted to just stay there, inside her for a while and watch her sleep, but instincts got the best of me. My dick was hard and inside a warm, wet pussy. I started thrusting and managed to keep it slow and gentle. My eyes were fully adapted to the darkness so I could just make out her face from the glow of the clock. After about five strokes, she started to stir. It was fascinating watching the feeling of pleasure cross her face, mixed with confusion. She must have been unsure if it was a very vivid dream, or she was really being fucked. Her eyes remained closed as she moaned louder, accompanied by a movement of her legs. It was like she was positioning herself to intensify the pleasure of the penetration. Then, realization hit and she opened her eyes. She tried to focus, then reached out and touched my face. Recognition showed on her face as she smiled.

“Wow, what a way to wake up,” she said very quietly, very softly.

“I was worried you were still sore, but I couldn’t resist your naked body,” I confessed.

“I’m not too sore for this,” she said, squeezing her pussy muscles around my cock for emphasis. Then, she squinted. “Ow. Maybe I’m a little sore.” Barely able to see my concerned expression, she continued, “I’m OK, we just need to take it slower than last night.”

“Yeah, last night was wild. I’m surprised your neighbors didn’t complain.”

“Me, too.” She giggled.

That was the extent of the talking as we now concentrated on fucking. It was a slow, gentle fuck. The feeling of her skin, the look of her face (what I could see of it), her gentle breathing were all so sensual. We came together, joined at both ends, kissing as sperm was passed from one to the other. After, I pulled out and she hugged me. We fell asleep like that, our bodies wrapped around each other.

  When I woke again, it was barely daylight and I knew I had to get up. I needed to shower and change before I went to work. She woke up as I was dressing.

“Don’t go,” she called, mournfully.

“I have to,” I answered.

“Then come back tonight.”

I thought about that. I was tempted to refuse. I thought about commitments. I also thought about my decision to not pass up opportunities. “OK, I’ll be back tonight.”

“And the next?” she asked.

“No, I have a business trip.”

“Oh. Where are you going?” she innocently inquired.


“Ooh, sounds nice. Can I come?”

“No, it really is business.”

  “Aw,” she complained. “When will you be back?”

  “Probably a week – if everything goes alright.” Yeah, if.

  “Well, we have to make tonight good enough to keep you satisfied for a week,” she mused.

  “If it’s any better than last night, I’ll be dead,” I teased.

  She smiled. By then, I was fully dressed. She got out of bed and hugged me. She followed me to the door, completely naked. I kissed her, a lingering kiss. Then I turned and opened the door. Just as I felt the chill of the morning air, she turned me around and kissed me again standing in the door.

  “You’re naked,” I warned.

  “It’s OK. Almost no one is up this early. The worst I’ll do is give some jogger a hardon.” She gave me one more quick kiss, then waved goodbye as I walked to my car. I blew her a kiss as I buckled my seat belt. She closed the door as I drove away.

  When I was getting in the shower at home, her juices drying on my dick reminded me of last night. I was going to miss Ellen - after tonight.

  When I got to the office, I spent the day with Ross and William again. We were discussing what I needed to look for in Havana. This was full preparation for opening a branch. I needed to evaluate the business opportunities. I needed to scout locations for the office. I also had to try to look for office staff. This was difficult because I didn’t know if we would open the office in weeks, months or a year or more. Either the U.S. would change its position about doing business with Castro’s regime, or Castro would no longer be in power and a new government would be more palatable to our government. Either way, a change would necessitate rapid action. Once things changed, I could expect to be back in Cuba in days. The day flew by. Before I knew it, I was back at Ellen’s apartment.

  We decided to go out for dinner. It wasn’t anything fancy, just a quiet meal together. After, we went back to her place. The sex was more subdued, in deference to her soreness. It was loving, tender. We enjoyed each other’s bodies. The touches, the tastes, the smells were each savored. Finally, we joined. We made love a few short times instead of one long time. Each time, I pushed myself deep inside her to shoot my cum. I loved looking into her eyes as I came. Looking into her eyes as my body tried in vain to impregnate her added to the thrill. We finally fell asleep around midnight, with Ellen’s legs wrapped around mine. The next morning, we made love again. I had brought along a change of clothes so we showered together before I left. I loved the feeling of our soap slicked bodies sliding against each other. We parted, both fully satisfied.

  As I was driving to the office, I thought how (if things turned out badly) she might have given a last meal to a condemned man. She might be the last woman I would be with for a long, long time. At least I had superb memories to carry with me.

  The last day at the office before my departure was spent going over the procedures for entry and exit. I had my ticket to Mexico. A credit card had arrived, concealed in a stack of papers in a FedEx envelope from our small Ontario office. One of the managers had opened a credit card account in my name. I held the Scotiabank card, its glossy red surface and gold printing glistening in the light. I hoped I didn’t have to use it. It had a credit line of $5,000 and it was for emergencies if I needed more money. My credit cards were drawn on U.S. banks so they wouldn’t be accepted in Cuba. I would also be carrying $2,000 in cash. I would be keeping in touch by telephone with our Ontario office. We had setup an elaborate code so I could appear to be making a routine call while I was in fact reporting on the progress of my mission. There was an awful lot of cloak and dagger to this trip. I kept trying to bury my nervousness.

  My flight was early on Friday morning, so I left the office early Thursday afternoon to pack. Word had been leaked around the office that I was going down to Cancun for a week of checking on business conditions and contacts. A few people kidded me on my luck at landing such a sweet assignment. The time I spent hidden away making preparations kept them from seeing how nervous I was. Only the four of us who were in the meeting in Ross’ office knew what was really going on, along with that one manager in Ontario who would be receiving my telephone calls. Agnes probably had an idea something else was afoot, but she was used to seeing things she couldn’t talk about.

  Following my instructions, I emptied my suitcase and checked the lining for anything that may have slipped in there. I needed to be sure of what was in the bag in case I was inspected in Havana. I decided to rely on casual clothesshorts, jeans, polo shirts. I figured tropical colors would fit in better. I avoided t-shirts with printing. I certainly didn’t want to call attention to my U.S. citizenship. I also went through my wallet, leaving behind most of its contents. I wasn’t comfortable carrying so much cash, but travelers’ cheques were useless where I was going. Once I got to Mexico, everything I did would be on a cash basis to avoid leaving a paper trail of evidence.

  I didn’t sleep well that night. I kept waking up. Finally, I got up and showered. I ate a small breakfastI was too nervous to do more. I got my bags together. I wasn’t bringing too much with me. At 4:30, I heard a knock on the door. The driver was there to take me to the airport. I took one last look around the house. I seriously wondered if I really would be back in a week. It was too late to worry now. I was on my way.


To Be Continued in

Chapter 2 – The Back of a T-Shirt


This story is Copyright © 2004 by Strickland83. All rights reserved.

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