OK. This my first attempt at adult writing. Be kind and constructive and you will motivate me to post more of the story.
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Chapter 1
Background
My name is Caine. I first read about sex in Cuba on the internet. I hooked up on the internet with a guy who had made the trip three times and could only brag about the great times he had every time. Sammy and I wrote back and forth enough that I figured I had to give it a try.
Learning about Cuba
Doing my own internet search I was able to research, finding most everything Sammy had told me was correct; and more. It seems that I can hook up with a young lady with an apartment for a night, or a month if I wish, if I pay for the food and our meals out!! What’s more, if I get tired of her she will refer me to any number of her girl friends and I can swap out. Seems almost too good to be true! Well, reality was something different. The key is to understand that the Cuban government does not allow the internet in Cuba, and then understand what Cubans do to get around that ban. You dig deep enough and you find websites in Mexico and Canada that advertize Cuban ‘vacations’. It is all veiled to prevent Government reprisals against those who use the system.
First I didn’t need any swap outs. Second, Maria kept me well entertained. She even liked my ideas and caused me to have one of the best months of my life. It seems that young ladies are commonly ‘available’ as young as 14 or 15. As long as there is no violence against them, the police look the other way. I guess the cops just look at them as ‘working girls’.
Cuba boasts the lowest rate of Sexually Transmitted Diseases [STD’s] in the world. I still packed a case of assorted condoms since I couldn’t find any data as to their availability. You see, I can only use the EX-Large size. Anything smaller acts like a tourniquet and only covers my cap and about first one third of my length anyway.
If you go to any of the large ‘clubs’ you will pay around $10US in cover charges. However, the ‘clubs’ are mainly populated with women out looking for a ‘date’. It’s not unusual to find 150 to 175 women, and only 25 or 30 male tourists. These women will charge you anything they think you will pay, but never less than $50US. Maria did much better for me.
The United States is still quite stuffy over Americans going to Cuba. There are no direct flights. You can fly there, though, via Cancun, in Mexico, or through Ontario (or maybe Toronto), Canada.
I talked my boss into letting me take most of Friday off. I hoped he’d go along with it, as I had made reservations to leave my hometown on a 2PM flight to Cancun. I made my connecting flight OK and arrived in Havana before dark. Maria and I had set it up that I would be met at the airport by her brother, Roberto, who drove a cab. He took me to Maria’s place, and wouldn’t take any money. He said, “Maria has already paid me, and she would be very mad at me if I even take a tip from you.” He came inside with me and introduced me to his sister. I think I said that Maria is 17. She is about 5’4″ and must weigh all of 110 pounds. She greeted me with a big smile, a bigger kiss, and a quick goodbye to her brother.
We ate a light meal of great fresh fruits and fresh baked bread. Maria asked if I would like to watch a video with her. I said, “Sure.” We settled in for some preliminary ‘get-to-know-you’ time.
Maria’s apartment is fairly small. When you come in the door you are looking straight through the living room and out some picture windows at beautiful scenery. To the left is an efficiency kitchen with a small one burner stove and a small dining table for two or three, but a large, very new refrigerator. I remarked on the new fridge. Maria is very proud of it. It is the first thing she has bought on her own with her own money. Looking to the right from the door is a half-wall with a bedroom nook behind it, and the bath beyond it. Her living room has one chair, and a small couch and assorted end tables and some tasteful lamps. We snuggled on the couch, but I don’t remember the movie. The couch is just big enough for me, sitting straight on the right side, and Maria sitting with her back my left side. She soon placed her right hand on my thigh. I responded by draping my left arm over her. Gee, that put my hand on her left breast! Maria responded by snuggling even tighter against me. I nuzzled her neck and she giggled, and turned her head slightly. This placed my lips in line with her ear. I blew lightly in her ear and then tongued it. This sent shivers from her head to her toes. While she was turning toward me she remarked, “It looks like this is going to be a great week!”
We kissed a full, complete, and long kiss. Both exploring the others mouth with our tongues. Her turning moved my hand from her breast. So I used my right hand to continue what my left had started. After a bit Maria asked if I would like to move to the bedroom. I told her I really needed to take a shower before we got serious since I had not had a shower since I caught my plane from home. Maria said, ” Showers are always a good thing. We can both take one. Then we will both be fresh for what comes after.” We held hands as we walked into the bedroom. We didn’t discuss it. We just both began undressing each other, interrupting often to hold each other and kiss. Maria went in the bathroom first to do ‘girl things’. When I heard the shower come on I went in. The shower was fairly small so we had to stand close together. We started with me lathering up Maria’s arms, then her back, followed by lathering her very nice breasts. I then slid down with back against the wall and my knees out in front of me. This way I could pick up one of her feet and place it on my knee so I could wash her foot and ankle. Once done there I washed her calf and thigh. My hand just naturally went up the inside of her thigh and put my fingers up into her pussy. Maria jumped and said, “OH!” when she suddenly felt me inside her. “I wasn’t ready for that!” “Sorry”, I said. “No-No. Don’t be sorry. It feels good. It just came as a surprise.” “Oh good. I like to provide surprises.” , I grinned. So I finished up that leg and put it back on the floor of the shower and picked up her other foot. She helped placing her foot on my other knee and I started washing it, just like the other leg. When I reached her pussy this time she was expecting me and I didn’t disappoint her. But, after I had washed that side of her pussy I put my hands around her hips and pulled her clit right into my mouth. “Wow, I wasn’t ready for that, either!” “I was just taste testing. It wouldn’t do to leave any soap in there. We wouldn’t want a soap rash, would we?” “Oh of course not. I guess I have never been taste tested before! I’m supposed to be the ‘pro’ here but you seem to be doing the teaching.” “Well, I guess it’s because I get as much enjoyment out of seeing my partners cumming as I do cumming myself.”
“Well, I guess it’s my turn to lather you up.” And, she did. Maria even tried my method of scooting her back down the wall and putting my foot on her knee and washing me from my foot to my crotch. She did a great job of washing my balls with the first leg. On the second leg she worked her way up to the top and saved washing my cock to the last. After a thorough washing she held my now steel hard cock in her hand and slipped it into her mouth. At first just the cap went in. But after a couple of short strokes she plunged my rather substantial cock to the back of her throat. She could take about a third of my cock. “I know I don’t do this very well, but I gag whenever I try to throat a cock.” “It’s OK. I think I only know one woman that can throat me”. She withdrew my cock so she could take a breath, took my cock back in her mouth. Her hand kept stroking the rest of my cock. Maria was an expert. I said, “If you do that one more time I will cum so hard I won’t be of any use for you ’til later.” She withdrew my cock completely and said, “Well, I wouldn’t want to do that.”, and she laughed. We toweled each other off and moved into the bedroom.
We shared the double bed that took up most of the bedroom.
Maria’s English was very good. I asked how see became so proficient. Maria said, “Well, most of my ‘dates’ are from North America. So I study in the English as a Second Language group.” I asked, “What is this study group?” “Since most ‘dates’ come from over sea’s nearly all working girls are learning or already speak a second language. Besides English there are study groups for Russ, Estonian and Portuguese. There are probably more. These are just the ones I know of.” “Your level is good enough to be teaching English.” She kind of blushed, “Well, I am a tutor for new girls just coming into the ‘business’.”
It was Sunday morning. We were laying in bed recovering from our latest ‘sexual exercise’ when Maria asked, “Will I be able to satisfy you for a whole month? You are using up most of my bag of tricks in the first three days!” I said, “Well, to tell you the truth, I have a fantasy I would like to share with you. Would you like to hear about it?” Maria sat up in bed and turned toward me allowing the sheet to drop to her waist exposing her beautiful petite breasts, “Yes. Tell me!” “Well.” I hesitated, “I would like to fuck a virgin.” “Caine, maybe you haven’t noticed, but there aren’t many virgins in Havana.” “I know, but, you told me yesterday there were many still in your home village.” Maria had shared with me that it took about a four hour bus ride to her home village. It was quite isolated and a very poor place. “Tell me how much does it cost for a family of four to buy enough food for a year?” Maria thought about it, and said, “It depends a lot on the current prices of food. They vary all the time. But, I think that $50US would usually do it.” I already had this information, but I wanted Maria to confirm it for me.
“Hmmm, how about if you took the bus home Tuesday, the stayed with your mom for a couple of days. If I gave you $100US, do you think you might be able to find a family that might trade a daughters virginity for $50US?” “Maybe, but, you said you would give me $100US?” “Yes, you spend what you need to on bus fares, clothes, I don’t know, any other ‘expenses’, and you get to keep the balance. I’m thinking maybe you could take the Thursday bus back maybe with a friend in tow for me?”
Maria thought about my offer. She said she knew of at least two girls that might work with. Both of them were younger than her, and lived in single parent families. Their dad’s had both been killed, and their mom’s could hardly make ends meet. Maria asked, “Do you have any other ‘requirements’ other than they be virgins?” “Not really, just that they won’t get me in trouble with the law. I think they ought to have the beginnings of some tits, you know I like them small.” Maria looked down at her barely B cups and blushed. “Hey, I’m not trying to make you feel bad. You have just what I like. Hmmm, maybe I should say they need to have at least a little bit of pussy bush growing, too.”
“OK. As long as their parents are OK with it, they have the beginnings of some tits and pussy hair they will be acceptable to you?” I thought for a minute and said, “Oh, YES!” Maria thought for a minute, “I am certain that the police will look the other way as long as the parents don’t complain, and they have the beginnings of a woman’s body. I know a couple of other girls here in Havana who started out when they were 9 and 10 years old. The law never hassled them. Their parents did not file any reports since the girls were both bringing in the only money the families made.” “Well, I’m not looking for anybody THAT young.”, as I got a mental picture of a nine year-old with hazelnut sized breasts and a little fuzzy pussy.
“OK. If I leave on the Tuesday morning bus I should be back Thursday late afternoon. The only thing is what are you going to do for those three days?” “I can just look after myself. I can go out and buy some food and bring it back here to cook it.”, I said. Maria was adamant, “No. That won’t work.” “Why not?”, I asked. “Because your Spanish is not good enough. You might get what you want, but probably not. And, if you do, it will be way over-priced if you try and buy it. No, I have another plan.”
Monday morning, after we had shared wake-up exercises, and our shower Maria said she had some errands to run and she would bring back some fresh fruit and things for lunch. We kissed and she headed out the door. Now I knew from my research that most girls did not have apartments but relied on their ‘dates’ to pay for hotel rooms for them to have a place to stay. Since I had found Maria I had not worried about that situation much.
About an hour before noon, I heard a key in the lock. When the door opened not only Maria came in, but another girl, too. She was a little shorter than Maria and could not weigh over 85 pounds. While there was no doubt of her womanly attributes (Her narrow red tube top and black, skin tight short shorts made that plain enough to see.) she had to be younger that Maria. Maria said, “Caine, I want you to meet Charlotta. Charlotta, this is Caine.” I greeted Charlotta not completely understanding what was going on. “Charlotta will be your maid, housekeeper and ‘companion’ while I am gone. She will do your shopping, laundry, and anything else you would like.” Maria smiled when she repeated, “…and anything else you would like.”
“Hmmm, does that mean I can’t go out in public while you are gone?” “Oh, No. Charlotta will just be your escort and ‘friend’ when you are out and about. By the way Charlotta likes to go out to a special swimming beach she knows about.” “What goes on there?”, I asked, already having a pretty good guess. Maria shocked me when she grinned and replied, “I don’t know! I have never been there. You will just have to ask Charlotta. By the way Charlotta is taking English as a Second Language class and wants to make sure that you tutor her and correct her English mistakes.”
‘Well, this certainly looks like a great situation both ways.”, I said, holding my arms out to Charlotta. She immediately set down the two shopping bags she was carrying, grinned, and came into my arms. As I hugged her, she returned the hug with a true full-body hug!!
After lunch, Charlotta gave me a hug and a kiss, and said, “I’ll come back tomorrow after Maria has left. You will have to let me in because Maria doesn’t have another key. I’ll bring about two days of food that I think you will like.” “Do I need to give you any money to buy the food?”, I asked. Maria broke in and said, “No Caine. I have that already taken care of.” After Charlotta left I asked Maria about the food, and other expenses that Charlotta and I might need to spend. “You can pay her public expenses. Bus fares, taxis, and food that you eat if you dine out. The deal I have for her is, she gets a place to crash and an English tutor. That and I am paying for the food she brings here and cooks for the two of you. Beyond that you could buy her a small gift, but not too often. Does that sound OK?” I thought for a few minutes then said, “Wait here a minute.” I went into the bedroom and dug through my backpack that served as my suitcase. I found what I was looking for and took it back out into the living room. I sat beside Maria I opened the small box. “I bought these in Cancun even though I didn’t have any particular use in mind for them.” I opened the box so Maria could see its contents. A dainty sterling chain with a single pearl drop was the first thing that caught her eye. Then, as I shifted some tissue paper around and you could see the set of earrings, again, in sterling. They had pearl drops that matched the necklace. Finally, in the bottom of the box was the bracelet. It too was sterling and pearls. All the pearls matched. “I could give her these. What do you think?”, I asked. “They’re beautiful! Were they for me?” “I bought them before I had ever met you. At the time I bought them I thought they might be for you, but not anymore.” Maria’s face fell, “You mean you wouldn’t have given them to me?” “Nope. They aren’t good enough for you.”, I said. Maria thought about that. Then gave me a big hug and a long kiss. She giggled like a little girl, and said, “Caine, I think this is the first time I ever hugged and kissed someone for not giving me a gift!”
“I think these would be very nice for Charlotta. Give her the necklace first. Then the second week the earrings, and finally the bracelet, but keep the ones you haven’t given her a secret so each new piece will be another surprise.”
Maria gave me a nice departing kiss and hug as she hurried out the door, “I must hurry so I can get a seat on the bus.” I ask, “I thought you said the bus doesn’t leave for another hour?” “I did, but all the seats will be taken a half hour before the bus leaves. Everybody else has to stand.” An hour later there was a knock on the door. I open it and greeted Charlotta. She had her hands full of shopping bags. I took some from her and we put everything in the kitchen. Then I got a great hug and kiss.
“What shall we do first?” , Charlotta asked. “Well, I haven’t taken my morning shower as yet.” , I respond. Charlotta grins, “How would you like someone to scrub your back?” “Only if I get to scrub your back!” , I answer. “OK” We go into the bedroom and I turn and kiss her again, “May I undress you?” , I ask. “Sure. Then I get to undress you though.” , Charlotta says. I start with her blouse. I unbutton it from the top down. The blouse material was thick enough that you could not see the her bra through it, but with the buttons undone I could see it is a very pretty rose color. I remark on its color, and I ask, “Do your panties match your pretty bra?” Charlotta giggled and said, “You’ll just have to undress me down there to find out, won’t you?”
I slip her blouse off her shoulders, fold it and hang it over the back of a chair. I can see that Charlotta has a bit more size to her tits than Maria has, even before I take her bra off. Sure enough, They are just about perfect B+ cups. I turn her around and unhook her bra. Then I put my hands on her back with my thumbs hooked on both shoulder straps. As I move my hands around from her back then under her arms both shoulder straps slide off. As I continue to move my hands around her chest I cup both her breasts in my hands and pull her back against me in a snug hug. Charlotta responds by backing her tight ass up against my dick. As she gyrates against me she can feel my beginning erection.
Roberto had made it a habit to stop by sometime each day to check on me and make certain all was well. I mentioned to him, (His English wasn’t as good as Maria’s or Charlotta’s, but very good enough for driving Norte Americano’s around.) that Charlotta and I were going to a beach to swim the next day, if this fine weather held. Roberto had a short conversation with Charlotta, then turned back to me. “OK, I will pick you up at 2 pm tomorrow and drive you to Charlotta’s beach, then I will come back at 6 pm to bring you home. I asked Roberto if he would get into trouble taking up so much time and gas running us around. He smiled and said, “No, my boss thinks I am really working hard when I tell him I have booked customers in advance. We do it all the time with arrivals at the airport. But, maybe, you could give me a little gas money, just so Maria doesn’t find out.” I laughed and said, “It will be our little secret.”
Roberto was good to his word and was right on time. The drive to the beach took about half an hour. Charlotta had packed us a little food and some canned juices. She also packed two beach towel apiece. Roberto dropped us off, getting our hamper out of the trunk and handing it to me to carry. Waving cheerfully, Roberto got back in his cab and drove away shouting, “Have a good time!!” and laughing until we couldn’t hear him anymore. The parking lot was small and rather unkept. Charlotta took me by the hand and led me over to a path through the trees and undergrowth. “The beach is out of sight from the land, and only people who want to see come close from the water. After about a five minute walk we came out of the undergrowth and onto a sandy beach. The beach curved around in a crescent shape with two tiny headlands of rock out in the water. The crescent beach was probably a mile long. There were couples and small groups scattered all around. Some people were swimming, all were nude. Charlotta said, “Come on. I see some people I know over this way.” Still holding hands we made for her friends, who, when seeing Charlotta, began to yell and wave to us. When we got to their spot everyone stood up as Charlotta introduced me around. Each lady there came up and gave me a full-body hug. I said, “This is rather embarrassing to be being hugged by all you beautiful women and me with all my clothes still on.” Two of the ladies laughed and said, “Well, well. We need to take care of that, right now!”, and with that they relieved me of all my clothes in something around fifteen seconds. The guys were eyeing Charlotta, but she knew what was coming and stripped off her clothes even before I was naked. However, in my case, all the ladies came back and re-introduced themselves, complete with ‘new’ hugs!
Charlotta explained that I was a ‘friend’ from ‘the country to the north’ and that I only spoke a little Spanish, but that I was helping tutor her in English. This brought positive nods from the group. Two girls and one guy said they, too, were studying English and would I please correct them if they made mistakes.
Charlotta asked me if I would like to go for a swim with her? I got up from where we were sitting, took her hand and we walked down and into the water. I guess I had not thought about what the water temperature might be in this part of the world. I certainly didn’t expect it to be as warm as it was. Charlotta and I splashed, swam and played in the water for about a half hour. We were both getting a little tired. I was standing on the sandy bottom with water about up to my armpits when Charlotta swam up to me, put her arms around my neck and her legs around my waist. A great kiss punctuated Charlotta’s question, “Can we fuck out here in the water?” “Well, the water has made me a little soft. Do you suppose you could do something about that?” “Oh yes!”, and she took a large breath and lowered herself down into the water, using her amazing mouth and started me on the path to real ‘hardness’. We spent about another half hour out in the water. When we came ashore, holding hands, Charlotta’s friends immediately began teasing us even before we were all the way back to our towels. The girls all wanted to know if Charlotta had left any for them. While the guys all wanted to know if I needed any help ‘satisfying’ Charlotta. One girl didn’t wait for answers. Anna jumped up and ran to us, and practically jumped into my arms, planted a big kiss on me and asked, “How about me next?” I looked over and said, “Charlotta?” She responded with a big smile and, “It’s a free country.”, and everybody laughed at the big joke. Anna grabbed a beach towel in one hand, and my hand with her other hand, and said, “Come on, we need a little part privacy.” “Do you mean, ‘A little more privacy?” “Sí, and thank you for correcting me.” We headed for the tree line, but not toward the trail we had come in on. Anna took us to a little nitch in the undergrowth. It was a very private little spot about ten feet in diameter. The only way anyone one would even see in was by coming in. Anna spread out the large beach towel on the smooth sand and sat down on it. She then extended her arms up to me. I took her hands in mine and let her guide me until I was sitting beside her on the towel.
Anna was a little older than Charlotta. She was 19, about 5″ 5″ and probably about 125 pounds She had long blonde hair. Her eyes were a very pale blue and her skin was the lightest shade of brown that I had seen on the island. “Are you from Scandinavia?” “No. I’m Cuban, but my father was from Norway. I never knew him.” There was no fat showing anywhere on her body. Just muscles. When Anna leaned toward me I met her and we shared a nice kiss. Anna took my right hand and pulled it up and onto her right breast, “I like to have these massaged. Do you give good massages?” “I’m not a professional, but people say I do a good job.” With that I laid her back on the towel and began a true massage of her right breast. I started at the base, squeezing and kneading her. As my hand would slip toward her nipple I would move my hands and start a her breast base. After about five round trips I was clear up to her nipple. Holding her breast tightly I brought my mouth down and sucked her nipple into my mouth, using my lips to hold it as I pulled up and away with my mouth. By the third cycle of this and Anna was wreathing on the beach towel. I let my hands slide off her right breast and slid them across to her left breast, and started all over again. Anna reached down and began massaging her clit. “Oh, you really are good. Maria told me you were also big and long.” “Well, I don’t know about now. Charlotta just drained me about ten minutes ago.” Anna said, “Hmmm. Just let me worry about that.”
I finished her left breast and she sat up, pushing me into the down position on the towel. She moved to her knees placing her mouth over my dick. I understood that some women could actually ‘throat a man’. I had only been throated once. And not very deeply. However, I didn’t think I ever expected to meet someone who could ‘accept me’ since I am known as ‘quite large’ [I have to be careful here. Others have told me this. I do not wish to be consider a bragger.], and didn’t think anyone would attempt it on me. Anna was about to prove me wrong. She took my semi-limp dick into her mouth, and began swallowing my cap. I had never felt anything like that before. Anna was good for 30 to 45 seconds before she would withdraw me from her mouth and take a breath. By the third cycle she had me hard as a steel bar.
The amazing thing was, she was actually swallowing almost half my cock! I said, “Anna, another cycle or two and I’m gonna cum!” “Oh no! I get you in my pussy for your load!” At that point she moved very fast. In a single motion she positioned herself over me and lowered herself onto my shaft. I was concerned about her not being wet enough yet. Not an issue. Anna impaled herself on my cock in one great thrust. Then began a leisurely pumping of my dick. “Caine, how long can you hold out?” “What do you mean?” I didn’t understand if she was trying to rush me, or get me to hold on longer. “I would like to cum first, Caine. But I want you to cum soon after me.” “Oh. Ok. I think I can hold out for a couple of minutes, if that’s what you mean.” “Yes, yes, yes. Hold out for me.”, as she kept moving up and down my shaft. Shortly thereafter Anna screamed, “I’M CUMMING!!” Which was a good thing, because her muscle contractions just about pulled my cum out of me. I mean, I was pumping, but I never had a woman who’s vaginal muscles were so strong as to milk me.
And that’s where Charlotta found us. Anna on top of me with my arms around her. Both of us sound to sleep. “Come on my lover boy. It’s time to pack up and meet Roberto in about ten minutes.” I woke up and tried to remember what had happened. After just having Charlotta, then Anna, I realized I had never been drained this completely in my Life. We had to wake Anna up so I could get out from under her. As she awoke I asked her a question, “Anna, I think I heard you mention Maria when we were just getting started. Did I hear you correctly?” Anna smiled and said, “Maria and I have been friends for years. She told me how big you were and she thought we might have a good ‘fit’. I will have to thank her. She is correct. And, thank you for one of the greatest fucks I have ever had.” “No, I must thank you I have never been throated like that, and I’ll probably never have it topped. Thank You.”
Charlotta cut in, “OK. Enough thank you’s. Caine, we have to go.” We went, waving to the rest of Charlotta’s friends as we walked passed them, and got to the parking lot with five minutes to spare to find Roberto waiting for us. On the way into town I asked Roberto if we were late? “Oh no. My last fare took me almost half way to the beach, so I just came out here and took a little nap, but, don’t tell my boss.”
I laughed and said, “It will be our little secret.”
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