Life Goes On - 5. Chapter 5 Key West - Meet Juan, the Cuban

Key West Florida, February 1966

With an early start the next morning they planned to be in southern Florida by the late afternoon. Since sections of I-95, the north-south interstate highway that would travel along the east coast from Maine to Florida were not completed their trip would include a combination of country roads when leaving Daisyville to sometimes congested long distance highways and then sections of high speeds on I-95. By dinner time they were in Fort Lauderdale where they stayed at one of the new ‘Holiday Inns’. With the exception of congestion around Miami the drive to Key West would hopefully be an easy drive.

The final part of their travels that day was on the ‘Overseas Highway, a 113 mile (182 km) journey along US Route 1. This scenic road goes through some very ecological sensitive areas while passing through interesting villages. The highway jumps from key (a small low island) to key. The impressive Seven Mile Bridge (11 km) seemed like an endless roadway skimming the ocean between Knight’s key in Marathon to Little Duck Key. They were told the best beach near Key West was on Bahia Honda Key. They stopped at the Bahia Honda State park for a break from driving and most important seeing the ‘boys’ on the beach providing memorable ‘eye candy’.

Finally by mid-afternoon they arrived at the Rainbow Guest House located on a narrow street just off Duval Street, Key West’s main street lined with bars, restaurants, galleries and tourist traps. The guest house had been recommended by a friend of a friend of Reg as a place where men with men could enjoy a relaxing vacation.

The property was surrounded by a fence six feet (1.8m) high and thick tall shrubs that gave total privacy to the property. The flowering bougainvillea and hibiscus included in the shrubs gave color that truly represented the name, Rainbow Guest House. The property consisted of a house with six guest rooms on the second floor and an L shaped one story building containing eight guest rooms. The rooms in the L had sliding glass doors opening to the pool area. The property was beautifully landscaped. There were chaise lounges with thick comfortable pads as well as wrought iron tables and chairs around the pool. . A deck on the second floor of the house could be entered from the house or by a stairs near the pool. A wall about four feet (1.2m) high surrounded the upper deck giving it privacy yet plenty of sun. The upper deck had seven chaise lounges. The street entrance to the guest house, pool and pool area rooms was through the guest house. The door to the street was always locked. To enter a person had to push a door bell or use the key given to each guest.

Arriving at the guest house Reg pushed the bell. A voice from a speaker at the door answered. Reg gave the voice his name stating he had a reservation. With the sound of the lock being released Will pushed the door open and the two entered the reception area. A man of about forty greeted them. “Hi, I’m Jason, welcome to Rainbow Guest House.” Tall, thin Jason was barefoot wearing only a pair of torn cut off tight Levis. The treasure trail leading to the bulge in his shorts was the only hair on his torso. He smiled as he discussed the atmosphere at the guest house. When Reg had called to make the reservation he was told the guest house only accommodated men and that nude sun bathing was accepted. He had been asked if he would be offended or uncomfortable if he saw someone nude lounging around or swimming in the pool. Reg assured Jason that neither he nor his friend would object and they would enjoy seeing men au natural. He further stated that they would probably also sun bathe nude. Jason repeated the possibility of nude sun bathing and swimming. He also stated that while officially guests were to be discrete sometimes they displayed their happiness. Assured that these new guests would enjoy the ambiance of the guest house Jason completed their check in and took them on a tour of the facility.

They were first shown to their room overlooking the pool. They entered through the double sliding door. The room was not luxurious. It contained a queen size bed, small table with two chairs, a low dresser with a TV, bathroom with a shower and rack for hanging clothes. Just outside the door there was a platform with two padded chairs. There was one step down to the pool deck. They noted three men were lounging around the pool either sleeping or reading. All wore brief, Speedo type, bathing suits. Jason led them up the stairs to the upper deck. Two men, both naked, were on chaise lounges. One was lying on his stomach with an incredible ass enjoying the sun. The other, about fifty with a pot belly, was lying on his back reading a muscle magazine (Popular in the 1960s, contained pictures of handsome, not necessarily muscular, men wearing g strings or naked standing in a position so their dicks were hidden). His unimpressive cut dick was hard. He looked over the top of the magazine when they entered the deck and said, “Welcome to the Rainbow,” as he scratched his balls.

They then were escorted back to the main house where Jason guided them to the living room with sofas, lounge chairs, a TV and a bookcase with books that they were welcome to borrow during their visit. They noted muscle magazines on the table. Jason also pointed out a small kitchen area where hot water for instant coffee and tea was available as well as cookies. He told them a continental breakfast buffet would be set up at the end of the pool or in the living room on rainy days. He also pointed out a bulletin board and brochure display case where information about Key West entertainment and restaurants was posted. Jason then told them that massages were available. Juan, a young man who had escaped Cuba, was the Rainbow’s maintenance man. Juan also had magic fingers and was available to give massages. Jason gave them a card with the prices and explained not all types of massages were listed. The basic massage was thirty or sixty minutes with a price listed on the card. However, Juan would give a special massage for double the price. Jason then said with a smile and wink, “Juan knows how to make all of your body feel good!”

As they walked back to their room Reg and Will saw Juan watering plants around the pool. The handsome dark skinned Cuban, about 5’ 6” (1.67m) wore only a pair of gym shorts and sandals. The black curly shoulder length hair matched the thick thatch on his chest. As they passed him he smiled while saying in broken English, “Welcome gentlemen, I hope you enjoy your visit here.“ Both Reg and Will had erotic feelings as they returned the greeting observing his macho, rough face, deep seated almost black eyes, full lips, defined chest, six pack, muscular arms and legs. The large hands on this small but mighty man seemed out of place. Both men assumed a huge uncut dick that matched the large hands was creating the bulge in the shorts.

Entering their room Reg said, “If getting the special massage gives me a close up and hopefully hands on his dick it will be worth the price. I think it would be nice to have relaxing massages before dinner. My body needs loosening after our drive.”

To which Will replied, “That Cuban is a total package of male sex. Did you see the size of his hands? I want them on me. But, do you really want a relaxing massage designed to sooth your body? While the ‘Special’ might not be relaxing or soothing I want all I can get. Let’s go talk to Jason and set up a time for massages.”

Jason told them that Juan was available that afternoon. They booked two thirty minute ‘Specials’ with the understanding that the one not getting a massage would stay in the room and watch. Reg and Will returned to their room to unpack and wait for Juan’s arrival. They each took a quick shower and put on the robes provided by the guest house.

Juan knocked on their sliding door. After entering he closed the curtain and then set up the folded massage table he carried in. Being sweaty from having worked in the garden under the hot Florida afternoon sun he asked, “May I take a shower to clean my body?”

The men agreed. Juan, standing in the middle of the room dropped the shorts he was wearing exposing the part of the body Reg and Will had not had an opportunity to ogle. Juan then stretched raising his arms. He then scratched his balls and adjusted the skin covering his uncut dick. Soft the dick was not impressive. On the way to the bathroom he stopped and leaned over to remove his sandals exposing his perfectly formed round ass cheeks. Both men gasped at the beautiful sight. Juan then turned around and said, “Do you want to watch me shower?”

Juan left the glass door open to the small one man shower. He took a wash cloth and generously soaped it. After washing his face he raised his arms and scrubbed each black thatch filled pit. He then moved to his fur covered chest taking time to scrub each nipple. Then turning around he handed Reg the wash cloth and asked him to wash his back. As Reg scrubbed the lower back Juan leaned forward to indicate the ass should be washed. Reg washed the round cheeks and into the crack. As he rubbed the cloth in the crack Juan moaned, “That feels great.” Putting the washcloth into his left hand Reg began to explore the crack with his right. Finding the anus opening he massaged the rosebud with his finger. “Maravilloso” moaned the Cuban. He shoved his ass back toward Reg which was interpreted that he wanted more than just a massage on the surface. Reg easily inserted his soap filled finger into the opening. “Maravilloso, muchas gracias,” Juan was now grinding his ass against Reg’s hand. Reg finger fucked a few strokes being sure to touch that special spot. Hearing the pleas of pleasure he pulled his one finger out and inserted two. The Cuban continued to respond with pleasure. Reg then inserted three. “Senior, you must stop. I am here for your pleasure. I will be creaming on the shower wall if you continue.” Juan turned around and wrapped one arm around Reg’s neck pulling him down to his shorter level. They deep kissed. Juan then turned to Will and pulled him in for a kiss. As they kissed Will reached down for the uncut dick that had not been impressive when soft. It was VERY impressive when hard, more than six inches (15 cm), thick and with skin covering the head when hard.

As both Reg and Will dried off the short Cuban he looked up to them smiling. “How can I give you super pleasure?”

Reg who really enjoyed topping led him to the bed and asked him to lie on his back. He then kneeled between the spread legs. Leaning forward he moved the Cuban’s arms over his head. Reg then leaned in kissing each finger on the right hand. He then kissed the hand moving down kissing until he reached the right nipple. Then he moved forward doing the left fingers to the left nipple. Still kneeling he continued to kiss the hard abs, the dick thatch, each ball, the inner left leg then on to each toe on the left foot, then from the right ball to the right toes. While Reg kissed the lower body Will moved in and after deep kissing and tongue probing kissed each nipple, he then lightly nipped each nipple, then bit each nipple. Juan squirmed with pleasure. Still kneeling between the legs Reg placed Juan’s legs on his shoulders. He pulled a pillow from the head of the bed and placed it under the ass. The ass was high with the rosebud fully exposed. Will moved in and using oils from a bottle Juan had brought greased Reg’s hard shaft, around the rosebud and then fingered oil into the waiting hole. There was no resistance as Reg slowly pushed in. With a smile on his face Juan uttered, “Fuck me Gringo.” And Reg did.

Will, who was not into topping as ardently as Reg stood next to the two. Reg pulled out, “I need a break.” Having greased his dick Will moved in and mounted the happy Cuban. He could not restrain himself and soon shot into the eager ass. Reg remounted and finished. With Reg upright on his knees still inside Juan, Will leaned in and took the handsome uncut dick in his mouth. He was soon having his first taste of Cuban cream.

While Reg snuggled next to Juan, Will went to the bathroom and moistened three wash cloths. Returning, he cleaned Reg’s dick, Juan’s ass and then his own dick. Will then crawled onto the bed where Juan was now happily sandwiched between the two tourists. After about fifteen minutes Juan said, “Now I give you each a massage.”

Reg lay on the special table. Normally a masseur placed a towel over the lower body (ass area) when giving a massage to provide the receiver privacy. Obviously no towel was necessary to protect the modesty of Reg. After ten minutes of pleasuring every inch of Reg’s back side from forehead to toes including some asshole probing Juan helped him roll over on the narrow table. To no surprise the mature man spouted a raging hard on despite having cum earlier. Juan professionally massaged all body parts and unprofessionally stroked the eager dick. Reg reached for and then stroked the masseur’s hard and dripping dick. Reg announced, “At my age I’m a once a day cummer, but that sure feels good. Juan then gave Will the same pleasures. At the conclusion of Will’s massage Reg kneeled in front of Juan who thrust into his mouth while holding Reg’s head forcing himself deep into the experienced throat. “Suck it Gringo, Suck it, Suck it, Suck it.” Will stood behind Juan and played with his nipples as Reg sucked. Soon Reg was getting his first, but not last, taste of Cuban cream.

When Juan left they noted he had been there over an hour and a half for their one hour ‘Special.’ The very contented men lay on the bed in each other’s arms and napped for an hour.

After dinner in a nearby restaurant they strolled along Duval Street, Key West’s main tourist street. Stopping at Sloppy Joe’s Bar they lingered over a beer at a corner table admiring the good looking patrons. As a result of the nearby Navy Base and Key West Navy Air Station there were always single young military men enjoying life off base. Also Key West was developing a reputation as a gay friendly vacation destination. In fact many businesses, especially art galleries, listed summer locations in Provincetown, Massachusetts on Cape Cod, another gay friendly beach destination.

They visualized Earnest Hemingway who had passed away a few years earlier sitting at the bar also enjoying the ambiance of men. Reg had read that Hemingway had suggested the name for the bar in the 1930s and was a patron for thirty years.

After the intensity of the loving session with Juan that night the two men had a cuddling but sexless sleep. The following morning they began their exploration that continued for six days of the many art galleries, tourist shops, interesting back streets, small beach, museums and piers. Evenings usually included visiting a bar with entertainment. Drag shows with foul mouthed comedians and queens of various beauties were always entertaining and sometimes produced beautiful male eye candy.

Most afternoon they lounged around the pool. As they returned to the guest house after lunch their second day they saw Juan leaving a guest room carrying the massage table. They knew this was the room of Arnie, the older unattractive man who was playing with his little dick when they visited the sun deck during their introductory tour of the place.

As they lounged next to the pool wearing the Speedo bathing suits they had just purchased Reg stated while watching Juan carry the massage table to a storage room, “I sure did enjoy our interlude with the hot Cuban yesterday. Would you consider me a ‘dirty old man’ if we had another session today?”

Will replied, “As one ‘dirty old man’ to another I would say let’s go for it. I’m not sure I have the stamina to do all we did yesterday but I would sure enjoy felling those hands rubbing me all the right ways.”

They talked to Jason and booked Juan for a ‘Special’ one hour massage later that afternoon. Juan again arrived hot a sweaty. This time Reg did not probe the willing Cuban with his finger. Instead he lubed his dick with soap and to the delight of the younger man shoved him against the shower wall and mercilessly rammed in his dick. While this was not Reg’s usual style, he was positive it was what Juan wanted. He was correct as he heard Juan calling out in Spanish with words that indicated pleasure. Following nearly two hours of sex, rest and massages Juan folded his board and prepared to leave. Will commented, “I admire your vitality. We saw you coming out of Arnie’s room right after lunch. Then you soon arrived at our door for an energetic and vigorous session. Your ability to keep it up, even at your young age, is amazing.”

Juan got serious, “That bastard. He has booked me for a thirty minute special every day, today being the fourth. When I enter the room that ugly man is naked. He just wants that little prick sucked. The first day and every day as soon as I enter he pushes me to my knees and shoves his little piece in my face. As he shoves it in his mouth he says, ‘Suck me Pedro.’ As I take the stinking thing in my mouth, he does not shower before I arrive, he says stupid and insulting things like, ‘You love it, don’t you, you little dago.’ I give him the best sucking I can. Not because I want to or he deserves it. I do it to make him cum fast. He is fast to shot his load. I spit it out. Since the sucking takes only a few minutes he is finished in less than five minutes from when I arrive. I then offer to give him a massage although I really do not want to touch his sweaty stinking body. Do you know what that total ass hole says? ‘You can leave. You have had the pleasure of my dick and cum’. So for five minutes of nasty work I am well paid. When I leave I clean my mouth with mouthwash and take a long hot shower. I always take a shower before I visit him. No way do I want him to watch and help me shower.”

“When I saw you two the day you arrived I said to myself, ‘You are two hot men.’ That first time I purposely came to our room dirty and sweaty as I hoped you would help me shower. Never did I expect to receive the pleasure you two gave me in the shower.” With that Juan pulled Reg and Will into a three way kiss and then departed.

Both Reg and Will, who had only met for a few days in Ohio and didn’t know each other well, had each been a little concerned about traveling a long distance over a couple of weeks with a new friend. By the end of their week in Key West they had developed a tender and loving friendship. They booked Juan for an hour every afternoon which Juan always extended to almost two hours.

During an interlude in their third session Will asked Juan about his background and life in Cuba. Juan seemed eager to share his tale. “Prior to the revolution I worked in a fancy tourist hotel starting at the age of fifteen. First I was a janitor’s helper where I did the dirtiest cleaning. I studied English and was soon promoted to be a bellhop which consisted mostly of taking luggage to rooms. On occasion the customer would ask me where a woman could be found. Usually a nice tip in dollars was given when the question was asked. My ‘unofficial’ instructions were to refer such questions to the head bellman who discretely made arrangements. One time a handsome traveler of about forty asked if I knew how to arrange time with a boy for fun. I offered myself. The man gave me a quick blow job and asked me to return when I got off work. This was strictly against the rules, but I was not going to miss such an opportunity. I went to the room that evening and spent the night having wonderful sex. It was my first sex with an American. The man was there on business for three days. I was with him every night. He gave me tips that equaled more than a month’s pay. About two or three times a year I had the pleasure of earning a little extra. One of the other bellhops discovered my transgression and threatened to report me if I did not give him blowjobs on demand. He was straight and claimed he got it from his girlfriend but that he never had enough. This went on during the time of the revolution. Americans who were very generous in tipping stopped coming to the hotel. Our customers now were from countries such as the Soviet Union where tipping was not done. Everyone became very unhappy. I shared a room in the basement with other workers including the guy who demanded blowjobs. One night he had been drinking and came for the usual. I refused. He was a strong man and threw me on the bed on my stomach. He pulled down my pants, pulled out his dick and shoved it in my ass. This was the first time I had ever had a dick in my ass. Two other drunk workers were in the room and watched. They got excited and joined in. For over an hour they held me down each having pleasure more than once. When they finished they all fell asleep. I realized I was now going to be raped frequently by these co-workers. Since I had no way to defend myself I decided to escape. While they slept I searched their lockers and found where two hid their money. The amount of money, mostly in American dollars, hidden in the back of the locker of the man who demanded blow jobs was more than he could have saved from tips. He must have been involved in some black market business. I also took what money they had in their pants. I had carefully hidden any extra money I had earned. With their money and mine I left the hotel. I took nothing with me except a plastic bag with necessary possessions. The bag was the type someone would take to a store since you needed to have a bag of your own if you bought anything. Walking down the street carrying a small bag was very natural. It did not look like I was planning a long trip. I had heard of places where you could find boaters to take you to the USA. I searched for three days and finally found a fisherman who would take a group to Key West. The distance from Cuba is less than 100 miles (160 km).”

“When I arrived in Florida I was taken by military police to a place where I was kept for a month. Finally I was released. Eventually I met Jason who hired me to work here at the Rainbow Guest House. He told me that if I worked for him I was required to sleep with him when he wanted me to. Actually, Jason is a good person and someone I enjoy having sex with. He is very gentle and loving. He wanted to fuck me and I felt I should do it to keep my job. When I lied and told him I had never been fucked he told me he would go easy. That first time with him started very painful and ended with me having marvelous feelings I had never had. I soon looked forward to our time in bed. He told me I could make extra money if I gave visitors massages. He bought a book on massage and I practiced on him and some very willing inn guests. When one of the guests I was practicing on asked for more than just a massage, Jason who was watching my massage skills stated that if I was willing there would be a fee for a ’Special’ massage. Every time I give a ‘Regular’ or ‘Special’ massage Jason gives me my share of the fee at the end of the day. Here most of the massages are ‘Special’.

“Most of the men I service are kind and just want to receive or give a fuck or suck. Sometimes it is just by hand. Sometimes I have a wonderful experience as I have had with you two. Sometimes it is a bad experience like the smelly Arnie with the little dick. I feel safe having sex here. Twice the guests have gotten rough with me. Once I ran out of the room naked and went to Jason. He visited the guest and threatened to call the police. The other time I could not escape so I screamed. One of the other guests ran to Jason and reported the screaming. That time Jason forced the person to checkout. He made the guy pay for the two days remaining on his stay. Some people would say I am nothing but a whore and Jason is my pimp. Maybe it is true?”

Both Will and Reg placed their arms around Juan. “You are not a whore. You are a young man in a difficult situation. While Jason is probably taking advantage of you, he is also providing you with a safe place to live and work. We are positive that as you get more Americanized you will be able to support yourself in a more traditional way.”

Three days later after their session on the last full day Juan asked, “Friends, may I sleep in your bed tonight. Usually I sleep with Jason. Tonight he has a friend from Miami visiting. I would much prefer to sleep with the two handsome Americans rather than alone. Reg and Will not only invited him to spend the night they invited him to go out to dinner and to a drag show. Juan had never visited an expensive restaurant or gone to a drag show in Key West. His reaction to the food, drinks and events of the evening were extremely pleasurable. Not having the endurance of the younger man Reg and Will were soft during the evening and all night. However, the ever ready Juan enjoyed a two man blow job from his friends prior to snuggling together for a good night’s sleep. By morning both Reg and Will had rejuvenated and gave Juan a hearty farewell with the deepest and longest fuck of the week.

They felt a great affection for this young man who had escaped Castro’s Cuba. They did not know how much of the fee they paid for the daily ‘Specials’ Juan received. They assumed most of the fee was kept by the inn. They wanted to help Juan improve his life in America. They handed him an envelope with $100 (close to $1,000 in 2017 money). Juan cried when he realized what he had been given. Receiving money when none was expected or required made him feel like a friend, not just a Cuban whore as some treated him.

Their four day drive back to Washington included stops in Savannah, Georgia and Charlestown, South Carolina. While both of these cities had excellent restaurants, hotels and sights to see there was no comparison to the memories, beauty and ambiance of Key West.