Sherry’s Caribbean Cruise

Taboo
2003-07-13

You do the math. Yes, Lauren was16 when she lost her virginity, got pregnant her first time and had Sherry. Notwithstanding, she was an all around great woman and when in her presence I felt myself losing that playboy attitude. I was top salesman in the company and the reward was a “family” five day Carribean cruise. Problem; I didn’t have a family. Solution; I’ll invite Lauren and Sherry. I knew Lauren would love it and for Sherry it would be a new experience. I thought this might be an opportunity to perhaps get closer with Sherry, if I were to get serious about her Mother. Several weeks later we are on board and headed for some tropical destination. Following the lifeboat drill and orientation, the girls into their bikinis and headed for the pool. I wish Sherry had gone to the pool by herself, because Lauren looked so inviting in her pink floral bikini. I was horny and my penis stiff as iron rod, but no such luck. “Love you girls. Meet you back here before dinner,” I casually said. In unison Lauren and Sherry replied, “Love you too. ”I steered a course to the bar for a cold Heineken’s.

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  About two hours and 4 or 5 green bottles later, I returned to cabin. On my way, I met the girls in the passageway. I walked with one arm around each of them, to our accommodations. My affection for both of them felt so natural. Sherry seemed to enjoy the physical contact. Once inside I excused myself, as my bladder was about to burst. “Hey ladies, I need to get rid of some of this liquid,” I said and stepped into the bath or more properly referred to on a ship as “the head. ”They chuckled and Lauren replied, “Yeah, pee for me too, cause I got to go. But, we need to get out of these damp suits first. ”After relieving myself I stepped out into the cabin. To my shock both mom and daughter were in the process of taking off their swim wear. I immediately turned my back not wanting to embarrass them and particularly not Sherry. “Oh excuse me, I am sorry. I didn’t mean to catch you disrobing. ”“It is not any big thing.

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   Turn around we wont blush,” Lauren said, “we are going to be in close company for the next five days, so lets not worry so much about the modesty. Sherry is Ok with it and so am I”“What’s the matter,” Sherry giggles. “Haven’t you ever seen a naked girl before?”As I turn, she continues, “I know you have seen Mommy naked plenty of times. ”I didn’t know whether to be embarrassed or play Mr. Cool. Wow! What a sight. Two naked girls standing before me. Yes, I had seen Mom naked many times, but never had I caught a glimpse of Sherry. Man oh man, they had nice hard bellies, not at all like mine. Mine was showing the early stages of a beer tumor. Oh yes, I had seen plenty of panty shots of Sherry before, but this was awesome. I could not help but stare at her little bitty tities and more than what I would expect in peach fuzz accentuating her pussy. Mom looked terrific as well. She always kept her pussy shaved and the rest trimmed, but it appeared as if she had shaved a bit more this time and it looked very inviting. Why she had done so I did not know.

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   I didn’t figure I was going to be going down on her with Sherry around. I had planned on celibacy for a few days or jacking off in the shower. Knowing I had to get dressed for dinner I said to myself, “What the heck,” and took off my shorts and tee shirt. Not realizing it, I had a tent in my briefs. It was quickly call to my attention. “Oh Mother,” in her all grown up voice says, “ I think Dave has an erection. ”“Yes Sherry, naked women seem to have that effect on men,” she grinned. “May I see it,” Sherry ask me, again in her most mature dialect. I was in shock and in disbelief as to her request. And to my even further amazement, Lauren nonchalantly says, “ It is OK by me, if you don’t have any hang ups. Dave, I have tried to make sure Sherry is informed more about sex than I was. Your anatomy may further her knowledge. ”Sherry had seen me numerous time in just my brief’s, but to my knowledge never in the buff. The thought of getting naked in front of her, I must admit, did kind of present an air of excitement and arousal. “Go ahead and take your underpants off,” she instructs me and gives me a big grin.

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   And then taunts me with, “ I dare you. Show her your penis if you are man enough. We have together viewed penises on the Internet, but she has never seen one for real. ”I could not believe this was actually happening. It seemed so surreal. I had planned to put on a fresh pair of briefs after I took a shower anyway. Hell’s fire they were both naked so why not. I cautiously, casually and slowly slid them down on my waist until they dropped to the floor. Once I was in the nude all of my self conciseness seemed to evaporate. I actually even felt pretty macho standing there before them. Fortunately, my cock had returned to a semi-hard state. “Woweeeeee, Sherry exclaims. “That is so cool” With an elevated degree of excitement she jumps up and down on the bed and in her now little girl voice says, “That is oh so rad, let me see. Let me see. Please let me.

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  ”By now my embarrassment was diminished and my modesty nonexistent as she jumps naked from one bed to the other so she could get a better look. Her close attention and her little pussy staring me in the face re-induced my erection. Not only did she have red hair on top, but red angel hair on her pussy as well. God, it looked good enough to eat. I would have loved to have grabbed he little butt and pulled it to my tongue. “Oh Dave, you are hard again,” Sherry says. Hell yes, I was hard again and if Mom wasn’t standing right there I is hard to say what might have happend. In an effort to keep things under control, I immediately said, “I need to take a quick shower so we can get dressed for dinner. ” The proverbial cold shower was in order to take to get rid of my erection. “If you need in the bathroom first just let me know,” I offered out of courtesy, hoping she would not take me up on the proposal. “No Sweetheart, we’ll get in there after you,” Lauren replies. I think she sensed my urgent need to change the surroundings. I enter the shower and no sooner had I adjusted the water, when the door opens. It is Lauren. She closes the door behind her and pulls the curtain to the side then proceeds to get in with me.

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   The dimensions were hardly enough to accommodate one let alone a second. Nevertheless, snug as it was, there we were. It was kind of romantic, but rubbing my already hard cock against her totally naked body was making me so damned horny. I knew that Lauren could tell it. “Hey I hope you were not upset with our nudity,” Lauren says while at the same time reaches down and wraps her hand around my stiff cock. She continues to both stoke my cock and talk. “I am so sorry if I made you mad. It is just that I felt as long as I were there it wouldn’t be a concern. We are very open. Thanks for giving her the opportunity to see a fully naked man. ”“Sweetheart I am not mad,” I said. “It was kind of fun and I probably now can do it without hesitation. It is just that I was caught off guard when I saw your naked daughter. God, she was good looking with her clothes off. It made my stick stand at attention.

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   She gave me a hard on just as you can. ”“It was obvious she was turning you on,” in a giggling voice says. “Hey buddy, look all you want, but don’t touch,” she jokes with a grin on her face. “If you do, I will castrate you with a rusty razor blade. ”“Don’t worry Lauren. So help me God I would never ever do anything sexual to Sherry,” I replied. “I respect her as if she was my own daughter. ”“Oh by the way,” I say, “What is my prize or reward for taking your dare?” With the water running over us we lather each other and gently kiss repeatedly. “Hey, speaking of rewards did you bring any condoms with you. ” she says. “I meant to make sure you packed some before we left. ”“Yeah, I did, but when the hell will we have the opportunity with Sherry around?”“We’ll find the opportunity, I’m sure,” she replies. “Plus Sherry knows we have sex regularly. She even confessed to me she once peeked in and saw us. ”“I suppose you have told her all about our bedroom encounters.

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  ”Lauren, quickly responded, “Yep, you bet I did. She asked and I answered. ”We exited the shower and dried each other off. Gently rubbing her all over with a soft towel was so sensual. Both of us stepped out of the bathroom. Sherry was laying naked on the bed, flat on her back and her legs spread slightly apart, listing to her Walkman CD. I would have loved to taken a picture. “Get in and take your shower,” Mom conveys to Daughter. With a grin on her face Sherry replies, “Did you guys have fun in there?”Sherry proceeds to take her shower as we begin to get dressed. I quickly put on some briefs, a pair of slacks and a dress shirt. Lauren is not in as big of hurry so I watch her put on a pair of red lacy bikini panties and matching bra. My God she looked so sexy and alluring. It seems like every where I look something is getting me aroused. Lauren was getting me more than aroused. “Snap me in back,” she asks.

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  I hook her bra, gently kiss her on the neck. Looking at our reflection in the mirror, I wrap my arms around her and cup her breasts. My body pressing against hers. It looked aw so sexy and romantic. I can feel my penis pressing against her butt. “Do we have time for a quickie,” I plead. “Not now, but maybe later,” she says. I’m thinking sure. There is no damn way with Sherry in the same room. Oh well I am going to enjoy myself even if I have to jack off. I reclined on the bed, grabbed the remote and turned on the ships TV. Shortly, Sherry walks into the room with a towel wrapped around her. Standing in front of the floor to ceiling mirror she drops the towel and picks up a pair of white sheer panties. Truthfully, I think she liked that big mirror as she could see the development of the pubescent body. As she slowly pulls her panties up I can clearly see her pussy from the rear as well as the string to her tampon.

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   She must have just started. That answers why she was so bitchy earlier in the week. I am already hornier than hell and now some kid is flashing her pussy at me. She sees me observing her form the mirror. As she continues to raise her panties she then quickly pulls them down in the front, for just a second, as a tease and waves in the mirror to me. I’d been caught admiring her body. She knew it and liked the attention. After putting on some panty hose that made her look like pure sex, I then observed her struggling with her bra. I doubt she could have been much more than a 32B max but in nevertheless her little breasts would have been a good mouth full. I nearly offered to help, but thought it might be inappropriate and piss Mom off. Damn it this was unadulterated torture. Lauren in her panties and bra pulled on a short red dress. “Zip me up,” she says and I graciously oblige. “Me too, get my zipper” Sherry says sweetly, so I accommodate her as well. She was wearing a most attractive white on white dress which made her look very lady like.

 

  I must say I was damn proud when we walked into the main dining room. Two good looking girls. One on each arm. Coming down the grand staircase I felt like royalty, as seemingly everyone cast their eyes on us. At dinner I could not quit relishing Lauren. She was not the prettiest girl I had ever dated, but there just something about her. Maybe it was the dim lighting, the soft music, and a radiating candle on the table that made the ambiance romantic. Shit, I was falling in love for real. About that time an older couple passed our table. The gentleman said with a West Texas accent, “Son, you’ve got a mighty fine wife and daughter. Now you take good care of them. ”“Sir I truly appreciate your complements. And yes, I’ll take good care of them. I just realized how important they were to me,” was my sincere reply. Neither Lauren nor Sherry said a word, nor did they seem the least bit disturbed having just been referred to as my wife and daughter.

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   They simply smiled as the couple departed. Looking at Lauren and Sherry again, I said to myself, yep I think I could handle a wife and daughter. They say that when love strikes it is like a bolt of lighting. I could feel the voltage tingling throughout my body. On our way back to the cabin we took a stroll around the deck as we admired the glistening water catching the reflection of the lights from the ship. The moon was bright. It seemed like something from a movie. I had the strangest feeling. I turned, wrapping my arms around Lauren and gave her a kiss. I could feel her tongue in my mouth and I reciprocated. A most wonderful sensation had come over me. It wasn’t an orgasm, but almost as good. We continued to kiss and exchanges I love you’s. Hell, I felt like a sixteen year old on his first date because I had not felt like this since I was a teen. “Ok time’s up.

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   Knock off the smash mouth,” Sherry jokingly says. “I want to go in some of the shops before we go to the room. ”Proceeding to the deck where the shops were, Lauren excuses herself to go to the restroom. Sherry and I drift into the jewelry shop where she wanted to look at a necklace. After picking out a gold necklace that set me back $100, we causally looked at the ring case. “Why don’t you buy Mommy one,” she asks. “Oh I don’t think your Mon is ready for one of those,” I reply“Why don’t you ask her,” she questions. “I’ll bet she would like this one,” pointing to a white gold diamond ring. ” “Maybe someday,” I respond and we step outside just as Mom is approaching. On returning to the room we found the Cabin Steward had prepared the beds for us which is customary. There was one made into a double and the other a single. I assumed Mom and Daughter would be in the double and me on the single. I laid down and turn on the TV while the girls started to shed there clothes. It really did seem like it was a family. I had just recuperated my last erection or more like the plural, erections.

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   Lauren left her bra and panties and was parading on back and forth. Sherry just her skimpy white sheer bikini panties on. She had discarded her bra, exposing those magnificent little tits. Every time she faced me and she did many time, I could clearly see her red pubes an little clit through the translucent fabric. I was stiff again and by now my balls were beginning to ache. Sherry went into the bathroom I presume to change her firecracker before going to bed. I took the occasion to lay Lauren on the bed. I wrapped one arm around her holding her tightly as I kissed her. My other hand I placed in her panties and ran my fingers to her clitoris. Within seconds I could feel her getting moist. Likewise I knew I was discharging some pre cum. About that time I heard the door to the bath open. Damn. I quickly roll over as if nothing was going on. Sherry however says in a smart ass, but cute voice, “Hey Dave what’s you and Mom doing?”She was no dummy so she probably figured I was playing kissy face and feeling Mom up.

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  Still being fully dressed I said, “I think I am going to go to the bar and have a beer. ” I figured if I got away for a while my sexual desires would dissipate. “That’s fine,” Lauren replies. On my return to the Crow’s Nest Bar I pass by the jewelry shop again. What the heck it won’t hurt to just look. So I enter. The clerk greets me, “Good evening Sir. Is there anything I might show you?”“No, I am just looking,” was my response. “But just for curiosity how much is this ring. ” pointing to the one Sherry had picked out. “Oh Sir that is one of the prettiest ring we have. It has a 1. 25 ct diamond and is 18 kt white gold. That ring is only $2, 950. And there is no tax or duty.

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  ”“Yeah, you are right. I don’t know anything about rings, but that one is truly sharp,” I say. I don’t know what grasp me, but I felt like I had to have that particular ring. What the heck, I tell myself, diamonds are a good investment so they say. I figure I can hang onto it until the time is right. Out of the store I come with a tiny little box and $2,800 on my America Express. Being a salesman myself I was able to get the clerk to take a little less. After being mesmerized by the sparkles reflecting the light off of at my purchase, I snapped back and realize what my original intentions had been. After finishing my beer I returned to the cabin. When entering I found Lauren in the double bed reading a book and Sherry laying in nothing but her panties in the other bed. Her panties had slid down far enough that it was exposing the very top of her peach fuzz, the sight of which caused pulsations between my legs. Just one more thing to get me turned on. She was sound asleep and out like a light. We had got up at 4:00 to catch the plane. The kid was beat.

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   Lauren had on a plain white midriff tee shirt and her lacy red panties. I could plainly see her nipples pushing through her shirt. “How was the beer,” Lauren very quietly says. “Oh it was relaxing,” I replied as I stripped to my black Tommy Hilfinger briefs. “ If you are ready to go to bed I’ll turn the lights out,” I said. But, I am going to leave a light on in the bath incase anyone needs to get up during the night. ” The one light in the bath left the cabin with slight glow. I got into bed and placed my investment under the pillow for safe keeping. I’ll put it in my suitcase in the morning, I thought to myself. Snuggling up to each other we passionately kissed. One thing led to another. I fingered her and she pumped my cock. She was getting wet and so was I. There was something so sensual about making love and trying to be so quiet as not to awake Sherry. Knowing, to fuck with your kid in the same room was taboo and I was trying to keep my animal instincts in check.

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  Oh, I wanted to put my penis in her so bad and it was obvious that she wanted it just as much. We were both very aroused. Our heart rates must have doubled I am sure. I very cautiously slid down and carefully pulled her pulled her panties to the side. The faint light from the bath gave me a ravishing view. Running my tongue across her clitoris, the flowing of her sweet juices intensified. Lauren was doing all she could to not make a sound. I was so stimulated knowing Sherry was sound asleep just feet away. It seems like it is always better when you doing something you shouldn’t with the element of being caught. “Dave quit, I can’t take it” she says in a whisper. “Come up here. ”I raise myself between her legs and move forward. My chest rubbing her breasts, I can feel her stiff nipples even through the cotton shirt she was wearing. I embrace her and place a kiss on her open lips. She responds in acceptance with her tongue.

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  My rock hard cock rubbing against her, she slowly moves her pelvis. I reach down and pull my cock through the fly of my brief’s. Touching my penis brings me closer to an orgasm. “Honey, we shouldn’t be doing this,” Lauren whispers. “What if Sherry wakes up. But I want you in me so bad. ”Without further word we kiss again and again. I reach between her legs an softy place my hand in one leg opening. I move her panties to the side. Lauren lifts her legs slightly and spreads them further. As I gently advance I can feel with my penis touching the outer most partitions of her feminine anatomy. She reaches down and takes my cock guiding it to her pussy. Ever so carefully I insert myself into her waiting vagina. She receives me with obvious pleasure. The feeling likewise to me was absolutely sensational.

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  Immediately, we are in harmonious rhythm. The sensation and passion intensifies. Being so quiet and moving so delicately as to not wake Sherry was so erotic. “Oh my God, I am going to cum,” she whispers. “Oh Dave I can’t hold it any longer. ”Her body becomes ridged and I can feel the contractions from within. They feel as if they are pumping the semen from me. Oh it feels so good as I explode within her. My orgasm is so intense. I kiss her once again as the stimulus lessens and we relax. “Oh my God Dave we didn’t use a condom,” She whispers in near panic. “What if I get pregnant?”I was initially stunned as well when I realized my error. The passion of the moment had clouded our judgement. While still coupled with my still erect penis inside her. For reason unknown to me I reach under my pillow and find the ring.

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  Giving her the ring of my affection, I whisper, “Will you marry me?”A voice brakes the silence. “Say yes Mommy, say yes. Maybe if you are pregnant I’ll get a little brother”.