Sailing Into Uncharted Waters free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
Synopsis: A young man with a deep secret finds himself in an exciting, yet precarious position when persuaded by a male photographer friend to fill in for an absent female model on a photo shoot aboard a charter yacht in Florida. Sailing into Uncharted Waters Day 1 - Morning Walking down the shop lined street, I'm wondering exactly why I had to awaken and get going so early this morning. I mean, I really enjoy sleeping in when I get the chance, just letting my body wake up whenever. I was only asked, last night, with no other details, to be at a certain nearby store by a specific time this morning. Since it was by a friend and I do live within walking distance, I sort of reluctantly agreed. As I reach the door to my destination, I think, 'Oh, yeah, to just wake up and know I don't have to get up, just lay there and enjoy the bed, the pillow, the covers, the morning...maybe somebody next to......' "Hey, Mark! There you are! Good morning. Great you could make it in this early, come on back," a voice I recognize calls out interrupting my little moment of reverie. "Hey, yourself and good morning," I say as I close the door behind me to the photography shop where I have just arrived. A sign on the door had said 'Closed' but I had been told it would be unlocked, so I had gone in. The shop is still dark although there's a single light on over the back counter. As I walk back, I glance at the various pictures that line the walls and shelves of the small front room, displaying the quality of work of the shop owner who has just welcomed me. The owner, Steve Thompson, a young man a little older than me is standing there working on a camera but he's looking a little anxious as I approach him. He's smiling, but it looks familiar. He's thinking of something that involves me, no doubt. It'll probably be okay, I decide, so I return the smile as I walk over, "So, what's up? Why did you ask me to come by now? You don't open until 9, right?" "Yeah, usually. Got a job this morning, very promising. Could be the big job I need to get profitable. And, I was, um, wondering, well, uh, hoping actually...." He pauses with a funny look. "Wondering and hoping...actually, what?" I'm still thinking a little on some of the framed photographs at which I had glanced. Most are scenes of city or country life, family portraits, yearbook pictures, weddings, a few more boating scenes than I remember from the last time I was here. However, a few are of attractive women. My private thoughts associated with the last of those make me inwardly sigh, but the man's voice brings me back to reality. "You see, I need a little favor, and, like, I think you'd be perfect for it." "You need a favor and I'd be, uh, perfect for it? What kind of favor? I mean I'll try to be helpful if I can, but I really need to know a little more." I try to banish the previous thoughts from my mind as I focus on Steve, across the counter. He's a good friend, and we enjoy one another's company. "Well, I had an agency model lined up this morning for this photo shoot job I've taken on. However, I got a call late yesterday afternoon, that the person couldn't make it and the agency doesn't have anyone else available who'll fit the part until Monday. I promised my client I'd have something by this evening." It's Friday now, just a little after 8 AM and I know how that is, having been part of a few group projects in college and one or two where I work now which were due on a Friday. Of course, someone screwed up some important part and wouldn't have it available until Monday. I can sympathize. Steve is a semi-professional photographer. Well, he could be a fully professional one if he could get some highly profitable assignments. I can imagine if something like this falls through, it'd make it that much more difficult, maybe even cause him to lose the shop. He called me late last evening and asked me to be here early. Now I think I know why. Well, I suppose I could help out, depending of course on what exactly he's looking for. "A model? Why do you think I'll be perfect?" As I'm asking, I'm thinking of the several theater plays in which I have appeared. I suppose posing as a male model wouldn't be that difficult - stand in awkward or unnatural positions and appear terribly bored. He sort of looks me over rather intently while nodding his head, which makes me a little nervous, "Well, you're right about the right size, height, weight even, and I've got the outfit, well, outfits, all ready, and just a little touch up here and there, and whatnot, and you'll look great, just what the client's looking for." "Okaaaay..., but I'd like to know a little more about what I'll be modeling. Clothes?" "Well, partly, see, you'll be positioned on a large sailboat, yacht, really fancy, as the client wants some pictures with at least one person in them, you know, to sell the picture, rather than just a static and empty boat. I've got two more people coming in the afternoon, but I really need one for this morning, going into this afternoon. The client is marketing Florida, Caribbean and beyond sailing cruises, like 5 and 7 day ones, or longer even, and needs some pictures for their glossy brochure." We're on the southeast coast of Florida, near Stuart, it's September and the weather is really nice, 80's during the day and sunny, with no hurricanes or other inclement weather on the horizon. Charter businesses are starting to get ready for the winter tourist season. He continues, "And, they absolutely have to have several to look at over this weekend as the brochure has to go to press bright and early Monday morning. There's a boat show starting next Thursday and they have to have them there when the show opens. And then for other shows in the next several weeks as well as displays around the area. So it's a very tight window." "That sounds about right, wait until the last minute and all that. Couldn't you have asked to get it going earlier?" "See, that's the problem, this just came up for me on Tuesday as their usual photographer quit on them, after putting them off for a while. Supposedly he found other more lucrative jobs I was told. They went looking quickly for someone to replace him and meet the deadline, and so far I'm the only one nearby that they found who was willing to do it. I thought I had everything ready by Wednesday evening, everyone lined up, until the agency called late yesterday. So, yeah, I could have asked, but it would have been about an hour earlier, at best. I tried some possibilities right after they called, with no luck, and then I thought of you." "I get it, sorry. So what kind of shots are you looking for? Yo, ho, ho, and a bottle of rum? Me as the captain of the ship behind the wheel, a deckhand would be all right, I guess?" He has taken a few portrait shots of me, a month or two ago, nothing special, but I sort of wanted them and he wanted to see how it worked in the studio here. It was right after he opened it, so I had the pictures taken, got some wallet sized prints and reimbursed him for his costs, so I am familiar with his work. Usually I don't like to see pictures of myself, they always make me look...unflattering, at least to my thinking. But the ones he took actually looked decent, well, more than decent, best I'd ever seen. To my surprise, the few young women I happened to show them to, each wanted a copy, and they were just casual friends! "Um, the ones I've got coming in the afternoon will cover that, not the pirate or rum for sure," he laughs a little at that and continues, "It's not that you're bad looking, but you really don't have that rugged, experienced, male captain look, and the deckhands are muscular and super tanned, and maybe have some beard." I smile, "The ones in typical brochures, you mean." I'll admit, I'm not exactly a man's man. I'm slight, about 5 foot 8, soft features, almost dimples under my cheeks, dark hazel brown eyes, medium brown hair, thick, though. Body on the thin side, not muscular in the least, but reasonable, very light beard, and I definitely look younger than my age of 25. I am in pretty good shape having been a runner in high school so I got used to exercising and eating right. I wasn't state champion material but I placed in some races, got my 'varsity letter', and was looked at as a reasonable approximation of a male. College was college, as I only ran for exercise. I dated some, as I do now, nothing long term. Steve is a little older, just over six feet, dark hair, medium beard, clean shaven, decent looking - perhaps a little handsome...in a way... I suppose....okay, so, maybe not quite as fit, but still in reasonably good shape. He was married but it didn't last even a year, which is now way behind him, and he dates some, but isn't involved with anyone at present, as far as I know. I'm not either, which I do know. "Uh, yeah," he shakes his head a little in irritation. "So what do you want me to be, cook? Steward? Passenger?" I suppose I can see this type of cruise having a full complement of crew or maybe he just wants a body. "Well, not exactly a passenger. I, uh, need some, um," he takes a breath looking right at me, then lets it out, "cheesecake. " I look back at him directly sort of wide-eyed, slightly gaping mouth, with a double take and a growing frown, "Cheesecake? You mean like a...girl model? Curvy figure? Swimsuit? Is that what you're asking for?" "Well, maybe not the swimsuit, although, hmmm, looking at you this close, that might actually now work," he nods to himself after again glancing at me all over, then continues, "but yes, the rest of it. Please? I really need someone, and with some little touch-ups, you'd definitely look that part." I shake my head, got to say something, "Are you sure you're talking to the right person? Me? I'm a guy. You know, no boobs, shortish hair, beard, light though it is, a lump or three between my legs." I gesture towards those parts as I mention them, although inwardly I'm starting to get a little excited. I should probably work on calming down, and finding out some more. "Yeah, I know all that, but, you're just about model thin for what I'm looking for, you have definite model features, a great smile, you're not too tall, light to non-existent body hair, and we can easily hide what little beard you do have. And besides, I've seen you before, you know, the theater, and then I have those proofs I took of you and I can tell that the camera really likes you. So, I know how the camera can see you. Please? Just this once? For a friend? I really need this job." As I'm trying to understand all that he's asking, I think back to yesterday when Steve asked me to come down to his studio shop. I actually started my vacation today, two weeks, with a paid holiday in there, so I'm having today and then the next ten weekdays off plus weekends. I sort of had plans, interesting plans, actually, although they can be changed, but I hated to get up this early the first day. On the other hand, I'm sort of glad now I came in as those plans could be modified to my private enjoyment, if what Steve is serious about asking, is what I'm pretty sure he wants. Steve's a good guy, he's been a decent, no, a good friend and he does seem to like me, which means he'll probably try to make it okay for me. And I do...um, like, yes, him. Friends help friends, with which I fully agree. Well, at least to some extent from what he's asking. The problem with all this which I can't really tell him, is that I'm a closeted cross dresser, with fantasies of becoming a woman, which is why some of his photos on display appealed to me. I mean it's all I can do to keep this masculine appearance up what with the body and inner desires I seem to have been 'blessed' with - which considering how my life is going, I have little choice but to remain looking male. When I put on weight, more of it seems to go right to my hips than a guy's normal place of his gut. And some also seems to go my upper chest. And, yes, I'm familiar with the phrase for that. I don't spend a lot of time at the beach because I think my body looks a little out of proportion for a male, thin though it is. But for a female! If I had better breasts, and more rounded hips, well, that's another story. Besides my body structure, like every so often, without warning, it's like there's a whoosh throughout my body, and I get all flushed with a kind of inner warmth or heat quickly spreading around, even causing a bit of a sweat. Yeah, I can guess what that sounds like. I don't usually like wearing watches or rings or neck chains, like they irritate my skin, but somehow, when I slip into some of my closeted clothes, jewelry like rings, bracelets, necklaces, earrings even, they all feel so right and very comfortable. And heels! I was a little worried at first when I bought some decent heeled women's shoes and slipped them on. But, once on, it was like, okay! These feel really good. 3" or 4" they're fine, I can handle. The higher ones, well, they do take a little getting used to. But, when I dress, it's like I feel I'm sort of a different person, or more likely there's this different person, female, inside of me, who was longing but is now totally thrilled to get out. And different in how I think, walk, act, talk even. There's more, like brassieres, I mean I find it so much easier to slip one on putting my arms through, bending over to make sure the 'girls' (what I do have right now) are snug and then reaching behind and fastening it with the two, three, or four hook and eyes, than it was to be with a girl in the backseat of a car, in the dark, and with one hand try to undo her bra. And boots! I could go on....wait, how could I forget? Chocolate. Okay, okay, enough said. So, what's the problem I'm facing now? I know if I really jump at this chance, it'll make me look rather odd, raise eyebrows, but how can I turn it down? I had the same problem with this little theater group of which I'm a member (in good standing, btw) and after appearing in a number of shows in small roles, several times I've been asked to audition for and have taken on gender bending/female roles. My size, features, and young appearance most likely have had a good deal to do with that. Or maybe I can even 'act' a little. Eh. I had the lead in 'Good-bye Charlie', which was well received, more or less. The one review stated that the reviewer was pleasantly surprised to find out the same actor played both the before and after parts. He was sure, like in the movie version where some unknown actor played the male and then Debbie Reynolds played the female who the male turned in to, that our presentation would be the same. To keep the illusion, the play staff used just my first name initial in the playbill with my last name and wrote my little bio with no specific gender references. The reviewer wrote that having the same person for both roles lent authenticity to the entire production and that the lead was believable in many ways, especially since the characterizations and even appearances were somewhat different. It made me feel good...and, of course, made me worry that I'd be labeled as some kind of deviant, as there are very vocal haters of the transgender community most of whom I've been able to usually avoid by just staying private. I've had to be really careful not to enjoy it too much, or complain too much either, just outwardly treat it as an actor's role. Especially when I was told how cute I looked in some of the costumes and make-up - which could have been teasing, but I suspect not entirely - and which secretly thrilled me. That was where I met Steve who had been hired to take publicity stills and we've been friends ever since. We met at a full cast rehearsal during the final days before opening, as he was taking publicity photos of the leads which included me in female costuming and make-up where he just assumed from what he saw, that I was a young woman. He surprised me by asking me out, after we talked some, before I changed back, I suppose possibly because I did sort of flirt with him a little - which I decided later was just practicing for my role. Yeah, uh huh, that must have been it... Anyway, I was inwardly flattered of course, which probably didn't show. Or did it? Hmmm. I mean, here was the first man who, not knowing me at all, thought I was a woman. Who wouldn't be flattered? Really? I then let him down gently and we laughed about it later as I bought him a beer at a nearby pub. Since then, we've kept up the friendship; become closer, even. Hung out, even double dated. Yes, I do date girls, and I do like them, and they do like me. Yes, like me. Maybe they, um, see something...No, I wouldn't think...so...anyway... However, trying to get his business really going in the past several months, such as renting this shop, he hasn't had as much time to get together with me although we do still have a beer now and then. I understand...I guess. As he said, the theater meeting and the photo shoot were probably where he got the idea of my filling in for the missing model. I suppose that makes sense. Our theater group has had other moments where the public just assumed we were using actual specialized furniture as props, and asked to borrow pieces, not knowing they were slapped together, almost sticks, and painted to last about a week or two. I sometimes wished my costuming and make-up could have lasted as long...or longer. I'm wavering, but I feel I have to put up some kind of macho show, "Yes, I know you have, but that was theater, and actors sometimes do those things, and everybody understands. Besides, we never had huge crowds or lots of publicity, even with your photo shoot, which did help. And now you want me to be dressed up again, but instead of slowly working into it and having help getting ready and all, what? You need me to be looking great by sometime later today? And in front of strangers? Who may or not think highly of cross-dressers? In public?" "If you say 'yes', I have that all worked out. You'll change and get ready here, a car will pick us up and take us to the shoot at 11." I can see there is some time available, but I do know how long it takes to effect a decent transformation, if I had all the right supplies, equipment, and so on. He continues, "And you will be introduced as a young woman model who'll, um, be...leaving right after the, uh, shoot. Yeah. And from what I understand, there will be practically nobody else there, most of the day. Nobody'll know, except me, who you really are." I vaguely pay attention to what he's saying as I'm thinking of how to handle this. Do I want to do it? Well, maybe, yes, I do sort of miss doing things with Steve. I think I'd like to do this for him and maybe if it's successful, he might have more time to hang out, you know, maybe even do other things....okay, get focused. I do want to do this, but I also do still have some concerns. "Okay, Einstein," I say in mock sarcasm, "I can still see several problems. First, I did learn to do some of my own make-up, but it was stage make-up, not the real world of women's cosmetics. Second, I had several weeks to get used to appearing as, well, being a woman, you know, rehearsals, with help from the other women actors. Third, the audience was never closer than about ten to twenty feet from me, and they were sort of in on it. On this boat, who's ever there will be like about six inches from me at times, I can imagine, and have no idea of who I am except what they can see. And besides, how do you know that when I'm dressed, I'll photograph well, and be the model you're looking for?" "So, let me finish, okay?" I nod and he continues, "First, if you say 'yes', you'll have my undying gratitude," at which I roll my eyes, "but I also have a couple of women friends who I use as assistants occasionally, who will gladly help us out here, help you dress, get made up, be around to assist you, and I'll make sure you don't have to say much of anything, or be near most of the other models later in the day, more often than not. There will only be a few shots of you with them, most of the shots I'll be doing with you will be just us two. And about being a model, I know what I want, and if I'm as good as I should be, I'll be able to guide you through it all. This isn't a New York runway, or catwalk, where they expect perfection; this is for the average Joe, who likes seeing pictures of attractive girls." "Yeah, the average Joe who has a spare couple of thousand or more to blow on a sailboat cruise." He grimaces for a second as I'm now thinking that he's getting a little exasperated, but he forces his smile and goes on, "They're just males like half the population and they like certain things. You know that. And you'll be well clothed for some of the shots because the client wants potential women customers to know that it's luxurious not just for a bunch of beer-guzzling hot-chick-leering men but for them too. Come on, please?" I ponder this for a moment, as that hidden part of me is saying, 'Go ahead, this is exactly what you've dreamed about being able to do', while the rational part of me is saying, 'You'll be found out, outed, humiliated, you'll have to move as you'll never be able to show your face.' I can see he really wants an answer, and I have to admit, I do like his arguments, and the thought itself of dressing up is appealing, and it'll probably help our relation..ship, um, okay, I, uh, suppose. So I take a breath.... "Okay, I guess I'll do it...for a friend" I sigh as his demeanor starts changing, "but, it has to be like you said, minimal to no contact with the others." I can see his eyes immediately light up and he almost jumps up like he might want to hug me. He doesn't but he does get this really happy look on his face, one I find rather appealing, in a way, as he replies, "Great," he takes a breath seeming to try to calm down and finishes, "that is so great. I'll do what it takes." And he takes another breath, I'm not sure why, probably, I would think, because he really needed someone, before finishing and looking serious again, "Okay, this will be a fully professional shoot, and I'll expect everyone we come in contact with to respect that. It should be only us in the morning, the other two models later in the day, and possibly the crew coming on board near the end. But, we have a really tight schedule, so now we have to get you ready, and quickly if possible. You didn't drive here this morning, did you?" "Nope," I reply as I'm starting to wonder if I did the right thing. I'm also wondering how I'm going to get all changed before 11, as I do know it takes a while. I also can't guess where we'll do the changing. "Good, no car to worry about," he says as he turns and goes to a side door, "Okay, Jeannie, Sue, here's your project for the morning." I'm taken aback a little, as two young women, probably a few years older than me, reasonably attractive, a medium brunette and a dark blonde, wearing slacks and tops quickly come through the door, barely nod at Steve and come right over to me and start looking me all over. And immediately, both of them agree, "This will be pretty straight forward, very doable. Your girlfriend, here, looks like she has a lot of good features." They turn to me for a moment, as the brunette says, "Hi, I'm Sue, and this is Jeannie." I reply, "Hi..." But before I can say another word, Jeannie says, "Hi. Now don't say anything more, we've all got to get into the right mood for this. Right frame of mind." Steve asks, "Can you have our girl here ready by 10:30? That's a little over two hours, like we talked about?" Jeannie finishes looking me over, and after getting a nod from Sue, glances back at Steve, "It'll take some doing, but I think so. Yes, but it'll be close." She then turns back to me while Sue has been looking me all over to my embarrassment, and says, "Come on now, sweetie. We've got a lot to accomplish, got to get started on you right away." Each woman takes one of my hands and they lead me into the back room from where they came out. I'm still in a little shock by how quickly this has all happened. And I shake my head looking back at Steve as we walk out. I wonder if I'm now a lamb being led to slaughter. Steve calls after us as we're going through the door, "We have to be at the dock at 11 to start the photo shoot, so get her ready as soon as you can. Oh, and her name is Rachael Ann Walsh." Sue pipes up as the door closes behind us, "Ooh! Rachael! Pretty name. Now, no peeking, Steve, until we're ready." Once the door is shut Jeannie says to me as they're leading me into the room, "Come on Rachael, this is going to be a lot of fun. And a photo shoot, you lucky girl. If the right people see it, and you look great, which we'll make sure you do, you could get all sorts of offers." That's an interesting thought, I imagine, but so unlikely as to not even briefly consider it. Sue looks at me again and turns to Jeannie, "I think when we're done, Rachael will be just as cute as any runway model. And a real heartbreaker for the guys." I roll my eyes again, "Just what I need." They just smile at that, as I can see they are getting serious about what they have to do. This room we're in is the changing room for when customers bring in particular clothing for photo shoots, of which I now remember noticing. It has chairs, clothing hooks, a table against the wall with a mirror, a smaller table, and I can see that they are quite ready for me, with all sorts of bottles and tubes of things, combs and brushes, some packages, several wigs, and some women's clothes on hangers. There's a bathroom adjacent and it has a shower. I'm wavering between almost overwhelming fear and anxious elation about what will shortly be taking place. With the door shut behind us, as we get to the tables and chairs, Jeannie continues, "Now you are to do exactly as we say, we don't have time for discussion or disagreements, there's barely enough time and you did volunteer. So, the first thing is, smile, let's see those teeth." I do and they say, "Your upper teeth look good, your bottom, they're okay, but models need a bit whiter teeth, so let's get these strips in there." They put on those whitening strips on both upper and lower. I understand the need for a whitener and I have been blessed with a pretty nice upper set of teeth, the bottom ones, not quite as neatly aligned but decent. "Good, next, please take off your clothes so we can see a little better what we're working with." "Now? Here?" I have become quite embarrassed, of course. I mean, I've never, at least since the days of being an infant with my mother, just undressed myself in the presence of two women strangers. "Absolutely, and we'll help a little," Sue replies as they both begin unbuttoning my shirt and undoing my belt. They are much faster than I can respond and in seconds I'm standing nude in front of them. From that moment on, it's like me as a male person doesn't exist to them, I'm almost some kind of girl mannequin that needs to be updated. Except on rare occasion when they have me turn around or bend over or lean against something. They spend a lot of time discussing rather intimate parts of me as if this living part of me isn't there at all. "Very good, a lot there to work with. I think this body can easily be shaped, with some additional help, into a nice curvy figure. Don't' you think?" "Definitely, now stand up very straight, Rachael, dear, learn to keep those shoulders back, your tummy tucked in, and breath from the chest, not your stomach. Girls definitely don't hunch like guys." Which they get me doing, and I continue trying as they remind me for the next two hours. They poke around and take some measurements, and push around parts of my body. "Yes, I think our girl here has some definite possibilities. Here, let's see how some of these add-ons might fit." They pull some fleshy looking material out of several bags, sort of partial breast forms and what looks like fake butt cheeks, and place them around me, seeing how they will fit. "Uh huh, I think these will be perfect, she'll be very curvy without showing all that much. She does have a very nice waist." They leave some out and put some back. I'm now thinking that Steve might have been more than just hoping I'd say 'yes', to have these two young women ready to go, with them having a selection of accessories that seem made to order for someone my overall size, and skin shade. Sue brings over a glass of water and several pills, "Here, Rachael, you need to take these right now." "What are....." I start to say, but Jeannie puts a finger to my lips to quiet me. "Uh, uh, uh, you don't get to ask anything, you just do as instructed, but what we'll be giving you is some help to keep your extra parts down there from being a problem. The effects eventually wear off, but these will keep you nice and small for the time you'll be needing them. Bulges for girls especially in the wrong places are not welcome at all. We'll keep them handy in case the shoot goes longer." "I...." "Quiet now, sweetie," Jeannie again puts a finger to my lips. As I swallow them, Sue says, "Okay, time for a quick shower, and we'll be joining you." And again to my slightly less embarrassment which becomes less and less as the minutes tick by, they both strip and join me in the shower. With both not much older than I am, they have very lithe and supple bodies. Most likely they work out and eat right, like I do. I try not to do the macho thing of staring at their bodies which isn't that hard as they become very busy lathering me all over with soaps, oils, and who knows what, which keeps me otherwise occupied. They also tell each other, upon carefully looking me over, that they will make me a little more full figured than either of them. I find their figures certainly attractive. It is a rather quick shower as they use several lotions all over my body, and when I glance down, I can see a fair amount of body hair circling the drain. "We don't have time for a waxing which would be far more efficient, but this will do...until we can get you done." I'm not sure what they mean as I would have thought this would be it, so I try to ask, "What do y...." "Again, sweetie, no asking, no talking, just do what we tell you." I nod with a slight smile and sigh, resigned to letting them do what they will. At the end, they also use some kind of cream on my face, rubbing all around where my very light beard is. I can feel a slight burning sensation on my cheeks, chin, neck and above my upper lip. They use a very warm, wet washcloth to wash down my face. "Okay, all done, now out and dry off." Which they do, with both toweling me which feels really nice, followed by drying themselves, and putting their clothes back on. And where I can feel parts of my body, they're all very smooth, even my face. All this attention and handling by two attractive young women, and yet when I look down at my genitals, my penis is quite small and extremely flaccid. I mean, I still have some testosterone in me, and it does cause certain expected male reactions at times. Of course, in my imagination, I would often be visualizing myself as a girl doing something with a guy, but my body still reacts in some ways (although not all) that you'd expect from a male. Some parts of me still like what they're doing, but while I'm feeling rather internally excited, there is surely no neural or glandular message being received down in my external organs. I guess those pills work. Once I'm out of the shower and now quite damp dry, they rub some kind of moisturizing lotion over most of my body, as Jeannie says, "We shouldn't have to color her hair. She will look very attractive with brown hair with some blond or reddish highlights." "I agree," the other replies as they help me on with a rather short and silky feeling robe, just barely coming down to my groin, open in the front, "We'll just pull a lot of it through to give her more body and make it less wig like. You know, a weave or extensions would really work out well, just not enough time." I don't have really long hair but it is lengthy and full, but a weave would certainly be interesting. "But first, we have to get her curves attached just right." And they begin working on the prosthetics to give me a more womanly figure. "She definitely has some feminine genes somewhere it would appear, as she has the beginnings of some breasts....and even some decent hips." I consider telling them that I just might have a lot more feminine genes than they realize, but I was instructed to keep quiet, so I do. "I noticed that too," Sue replies looking at my chest area, "so it should be fairly straight forward to push her breasts up as much as possible and attach these underneath, covering her natural nipples with the ones on these. " "I agree," and turning to me, she continues, "So, Rachael, you will definitely have decent sized breasts, and if you keep them covered at least just above half way, everyone will fully believe they're all yours, because what they will see will be you. The clothes, outfits, we helped Steve pick out for you, will display them very nicely." They begin working on attaching the partial breast forms as one tells me, "We're using an adhesive on these that requires a special solvent to remove which we will keep here in the office. Once on, they will be almost impossible to remove without the solvent. And besides the adhesive, which is skin friendly, we'll use some body blending creams to add more smoothness to the attachment lines so if your dress breast line were to drop a little, people would have to look very closely to realize what was going on, and of course, these are scalloped and very tapered edges so that there will be no obvious straight line or ridge." I can only shake my head as this is getting very involved. As they are attaching them, Sue mentions, "Have you looked at her eyes? They really pick up light quite well, almost like they're lighted within. That flashing look and her skin tones, gives me an idea of giving her a slightly latina look, like a grandparent or great grandparent was Hispanic. What do you think?" "I noticed them, too, and I completely agree. Looking at her and imagining the finished product, she's going to have a little resemblance to that American model and actress from like 30 or 40 years ago. Raquel something or other if I remember." I'd tell them that I've researched my family history a little and I do have one set of great-grandparents from somewhere in the western Mediterranean region. Maybe I'll mention it later. "You're right, I can see that now. Rachael here might turn out to be our best creation yet." "You've done this before?" I almost whisper thinking they may get mad at me. They both giggle, "Well, usually with just young women who want to change their looks, but don't feel they're ready for things like plastic surgery or Botox or silicone or saline breast enhancements. But we do have experience doing cross-dressing males, and sometimes a transsexual male. Of course if you like the finished product, we know a doctor who can do those things. Are you interested? We can give her a call, if you'd like, set up an appointment." "Um, no, I...maybe I should, um, get used to all this first? And, uh, anyway, it's like only just for today, and for Steve, so, um, I don't, uh, think so." Oh, my, are they asking what I think? This is confusing and how did I answer them? I don't know. Both young women glance at me and then look at each other and smile, with Sue replying, "Okay, sure, but if you change your mind, just let us know. She's very good, and very private. Only takes referrals from a few people. And we're on that short list." I'm not sure I want to be thinking of things like that. I mean, today will be interesting enough, and maybe sometime later, I can think things out, but surely not now in my life, where I am, and all. I guess. Jeannie says, "Okay, the parts are attached; now Sue will do your toenails and I'll be working between your legs to give you something resembling a vijayjay. So, lie down over here." I wish I had more time to look over these breast forms. Attached to me now, my full looking breasts do look a lot more real than any forms I've ever used, they have a weight and feel to them that seems to be quite natural. I'd love to spend some time in front of a mirror looking them over as well as those on my butt. But they keep moving and keep me moving. I guess some time later today. I hope. She points to the table which has a sheet on it, and I get up on it, lying on my back, and sure enough, Jeannie begins manipulating my genitals, saying, "First we give you a little shave leaving a teeny bikini cut, besides making sure other places are quite smooth," Which she does. "Now we push these ball-ee things up into you, and then gather the loose covering, slip a band around it at the base, and tuck your man part back into it. From a distance it has an appearance close to what a girl has. Oh, and I'm attaching a little soft tube to the end so that you can still decently relieve yourself, but of course, you'll have to sit on the seat like the rest of us gals do, no standing for sure. Finally, I've attached a little bit of special tape to each side to keep everything fitting right and tight. The tape is almost transparent and has a skin like cover texture." As she manipulates my penis and ball sac, Sue goes to work on my toenails, filing them, adding small extensions, and then adding polish. "We're going to put some lotion on your legs that will give them a little more tan, also. Hardly anyone wears hose anymore, so your legs will have to look great." After they finish, they go to work on my fingernails, one girl on each hand, filing, gelling using small l.e.d. lamps, and painting. When finished, I look at them and they are so perfectly manicured, and look very feminine with attractive looking, longish but not super long nails, as do my toe nails. I mean I've attempted polishing my nails and using press-ons, but these look so good! And I can even glance between my legs and I touch down there and it's just a small slit opening. I've often considered just giving up on my dream of becoming a woman. To do it right - or following all the standards, I suppose - it takes a lot of time, a lot of dedication, and especially a lot of money. The last part is probably what I'll never have. I've heard there are places that will do the necessary operations in less time possibly for less money, but the chances of severe problems are very real. So, maybe I should just purge my closet (like I've done several times before, and if I keep doing this, probably more times in the future!), find some nice young woman who I can love in a way and will love me back in a way, get married, raise kids, work at a hopefully half way decent job, retire, enjoy the family, grandkids...and wonder whatever happened to my life. Or maybe this can be the push I need to at least make a decent decision. I love what these women are doing. I can imagine for the rest of today, I'll have at least a slight chance, better than any previous time, of living part of my dream. Maybe this will be the only chance I'll get. Or maybe use this to keep it going for the next day or two, or even two weeks, and then...I can only hope. It's now closing in on 10 and they start on my face. Sue says, "Steve told us you've had theater make-up on, and appeared as a girl?" "Yes," and I think, oh great, Steve is telling everyone. "Did it go over well? Do you think it was successful?" "Um, yes, I think so. The reviews were good, well, the one review was. The audience clapped at the end, and responded to some of the humor, so I think it went well. And some people actually mistook me for a young woman as they congratulated us in the hallway after the show. They actually thought I was a female masquerading as a male in the opening scenes. "Good, you've had some experience it seems. So, this make-up is a little different, but will really make you look even better, I should expect. First we'll pluck those eyebrows to give them a nice shape." "Uh, not too much," I'm also not going to tell them I have tried real cosmetics several times. I just never thought I was that good at getting it all together. Well, girls do start at a pretty young age, experimenting, in front of the mirror, with friends, and all, before getting really serious. I've had no chance at that, for sure. "No, just enough to give them a little feminine look, a nice arch, but take off the make-up, put on jeans and a white tee, spit and chew, slouch, saunter when you walk, use crude language, be a regular male, and nobody'll really notice." We all three laugh a little at that. They then go to work, applying foundation, blush, eye shadow, eyebrow pencil, eye liner, a little mascara. While they are doing that, they are explaining much of the steps, both what they are doing and why. I try to take as many mental notes as possible. I can hope to remember some of it for tomorrow at least. "Her lashes are okay but they need a little more body, not that much longer, but fuller, let's put these on," one says as they attach false eye lash extensions and proceed to put a slight curl in them. I say, "With all you're doing, I'll bet you could turn any male into a very attractive woman." They both sigh, and Jeannie responds, "I wish that were the case, sweetie, but sadly, it doesn't work that way. You have a lot to work with, most guys don't. Their beards are darker and thicker, they have lots more body hair, their jawline is square, some of their features are oversized. But you have so many good features that we have easily just enhanced. You know, we have tried to make over a guy or two who really didn't have any good features at all, and although they said they liked it, we were pretty sure, right, Sue? That they would be seen immediately as a guy dressing up. You are going to look all woman." Sue adds in, "Absolutely." "I hope so, but I wonder if I'll be able to pass in my movements, reactions, body language, things like that. I do know that men and women are different in so many different little ways." Sue responds nodding appreciatively, "I'm glad you understand, Rachael, that will go a long way to help in your passing as you'll be aware of what you have to be like. But you have done theater, so I think you already have a head start on many of the cross-dressers we've done, and you'll pick up the rest, just give it time, and besides, we'll be there to help you, as needed. Now hold still, we have your lips to do." They finish up and look at me, "Well, except for the hair and a few minor things, you're looking really good." "Can I see?" I ask as I can feel lots of little differences to my face, as well as to my body. "Not yet, sweetie, not until we're ready. So let's get you dressed and then we'll get the wig on you." "How did you two get together with Steve?" I ask as they start working on my clothes. Jeannie responds, "Well, we do make-overs as we mentioned besides standard beauty shop treatments. We're both licensed cosmeticians and met in a shop and decided to go out on our own. Around here, the Gold Coast, our regular clients are mostly older women of course, and most of it is now by referrals. But as we said, we do younger women and some gays, too, and a few transgendered. During the winter months we have almost more of all types than we can handle at times. Often they want their picture taken, and Sue here happened to meet Steve some time ago, and in exchanging information realized we could help each other out." "So you've known each other and Steve for some time?" "Yes, thankfully all three of us have gotten beyond the dating stage so we can now be very professional about our relationship and still be friends. And this is a slow time for us, so this job is perfect." Now I understand why he never mentioned them to me before, it being a professional relationship. Obviously from what they just said, he dated both of them, probably sometime after his divorce and meeting me. Yet, only once or twice with each of them, I'm guessing. Besides, Steve and I only double-dated a few times. They help me on with panties, and then Sue says, "We're going to start you out in a waist cincher, see how you do. It'll help learning how to breathe right, and get you started with a good figure. Depending on what you're wearing later, especially after lunch, we may have you remove it and see how you look." After they help me on with that, it's followed by a low cut bra, and a purple-ish peasant type dress with an elasticized breast line, up over my shoulders with full sleeves down my upper arms and a modified empire waist coming to a flowing skirt in slight ruffles to well above my knees. The front neck line is significantly low across my breasts, riding just above the attachment line, which makes them quite noticeable. "Now we have to do something about the ears. We could do clip-ons, but they get noticed rather quickly. Almost every model these days has pierced ears, so we're going to do yours." Sue notices my grimace and continues, "Yes, we know some worry about that, but remember, lots of people of both genders wear studs these days, and if you leave your earrings out, it will be noticed far less than if you used clip-ons." I gulp as they use the alcohol, needle and ice cube method, and soon I'm wearing earrings, simple hoops, but very light so my ears can heal properly. They ask, "In your theater role, did you wear heels?" "Yes, about an inch and a half, maybe two." I don't tell them I've had a little more practice in higher heels, on my own, in private. "Okay, that's a good start. We'll give you three or so inch strappy sandals to start with." And they place them on my feet. "They will take some getting used to, but you shouldn't have to wear them all the time. Of course, if they are too comfortable, we may exchange them for 4 inch or more." "I don't know..." I still feel the need to show some concern. "Don't worry, we'll just have to see." And in a moment, I'm in heels, which looking down at them, I find I like, especially with my now polished toenails. "Okay, let's see you walk." I do, taking a few steps and then turn and come back. They approve sort of glancing at one another, but waste no time, as Jeannie says, "Now the wig. It's rather involved much more so than theater wigs. We'll be bringing some of your own hair through, to give it more underneath body, and get it really close to your scalp, and attaching it all around. It's not the same adhesive as your breast forms, but it will be firmly attached. Just simple rubbing alcohol should be able to loosen it." The wig is sort of medium to dark brown with a reddish tinge and some blondish highlights, and long, falling easily to my breasts and down my back. After attaching it all over, they loosely pull it back into a rather modified ponytail with a clip that lets it all fall spread over my shoulders front and back. They have given it a little body on top of my head, not too much, though, and finish with loose bangs with a slight part across my forehead as well as a slight wave or very relaxed curl at the ends. Jeannie mentions, "If I remember, that actress we were comparing you to had a lot of 80's big hair, we're giving you a more relaxed current look." Sue adds, "I think this should work quite well. Like we mentioned earlier, if we had more time, we'd try to get you a weave, just like getting you waxed. But this will work for the next day, maybe two or three." 'That's interesting,' I think but I don't have time to really consider that as immediately Jeannie says, "Let's get a simple necklace on you, a bracelet, a few rings, and one for a toe, and a little ankle bracelet." I'm now realizing that I'm absolutely loving how it's all coming together, especially with the jewelry as I've longed to go all out like this, but always seemed to hold back a little. The feeling of the various items on me has me more than a little excited. I'm also inwardly thrilled about the make-up as they have a lot more experience than I do on just how to apply it all. I've tried to make a lot of mental notes on what they are doing or have done so that if after today's shoot, I want to try dressing up, I'll know how to do lots of various things. Or at least make better attempts. They finish me up, spraying me very lightly with pleasant fragrance, and then say, "Okay, Rachael, you can look now." And they hold up a mirror with my back to the big mirror so I can see all of me. I am astounded at the reflection peering back at me, as I turn my head and body this way and that. It's what I would consider a very attractive looking young woman, someone I barely recognize, with significant visible breasts and cleavage, decent waist, rounded hips, long beautiful hair, heels, smooth supple legs, fully manicured nails, and make-up and jewelry. I felt a little passable in the theater, not so much in privacy, but now! Is that really me, I see? "I don't know what to say! This is, you both are amazing with what you've done!" I mean, hearing the click of my heels on the floor, feeling my hoop earrings dangle against my head, feeling my hair coming down across my forehead and around my shoulders, and down my back, and onto my breasts. And my breasts! Seeing my manicured fingers and toes, feeling this dress on me. There's a moment when I have to remember to actually breathe. As I open my mouth, they say, "Let's get those strips off." And quickly I see my teeth are a little whiter. As they look me over and touch up a few things, Steve knocks at the door, saying, "We need to be going in a little bit, how much longer." Sue says, "Come in and look at your model." He does and I can see the shock on his face. "She's...you're beautiful, like...oh, my, go...," he pauses, and seems to try to think what to say, then continues, "exactly what I was, um, hoping to...hoping for, but to tell the truth, way more than I would ever have expected. Rachael, you are...unbelievably pretty. I mean everything about her." He looks at Sue and Jeannie, "You, um, didn't substitute...." Both young women get a little irritated, "This is Rachael who you gave to us to make over, and we have done it. We would never ever consider fooling anyone with a substitute." "Then you are both fantastic, I just can't get over how she looks like I...I mean how good, how absolutely gorgeous she looks." "Give her some credit too, please, she had all the necessary features. There are a lot of girls who would die for her high cheekbones, her sleek jaw line, her eyes, her nose." "Is she...are you all, ready to go?" "How about five or so more minutes, we just have to check on some things." "Okay, ten at the most, and then we really, really have to go as the car should be here any moment. Rachael, you look....great, better than I re...um...just great." I just smile at that, not exactly sure what all he seems to be trying to say. And I give a little nod, not wanting to break the illusion. After he leaves, the girls say, "Okay, we need you to walk around, remember to keep your shoulders back, don't hunch, breath from your chest, work on keeping your stomach in, and be just a little deliberate until you get used to walking. Keep those thighs to the front." I do, and they seem to be satisfied that I know how to handle heels when dressed, as Sue says, "You're actually doing quite well in those, we'll bring some higher ones with us, but those should be fine for now. I'm impressed." Jeannie takes over, "Now the sort of hard part, your voice. To do it right would take several intense hours, if not more, of training, so we think you should barely talk, whisper if possible, maybe claim a sore throat or something, but we can give you some tips." "Um, let me try once, I did practice a little for those theater performances and I may still remember some of it." I know for some there's a way to manipulate the larynx and throat to give a higher pitch. It's a lot more than that, I also know. But I try. Of course, I don't tell them that I have practiced at home since then. I focus on what I've practiced and remember and then say, "Hi, I'm Rachael, and you are....?" "Oh! Not bad. Um, Sue, and this is Jeannie, hi!" "Hi, Rachael." "Oooh, it's so nice to meet you two, I just know we'll be good friends. I'm heading off to a photo shoot in a little bit and I just can't wait. Would you both like to come with me? I'd love it if you would." I smile at both of them, trying to show that I can be friendly if I want. And I flutter my eyes a little. Sue turns to Jeannie with a huge grin and a nod, "That's pretty good. I think our girl is on her way to getting it. And I'm not going to ask about where it might have come from, that theater gig is a good enough excuse." Jeannie nods in agreement. I'm not sure what she means so I just ignore it as she turns back to me, "Rachael, I'll be coming with you until lunch break, and we'll bring your changes of clothes, and then Jeannie here will take over after lunch, maybe bringing some more. We'll make sure you continue to look great throughout the shoot. Okay?" "Oh, my yes, I'd like that, a lot. This is going to be such a fun day and all?" I had to think about how to do this, talk like a girl, a lot before I just opened up. I had that training with the several theater plays, but I kept it up in my own room, just for fun I guess, not ever suspecting I'd actually be able to use my feminine voice in this kind of situation. I had always hoped it was okay, but it's really good to have these young women give their affirmation. Yet, I certainly don't think I'm ready to tell them about my secret desires. But if I did open up to anyone, I think Sue and Jeannie would be towards the top of the list. "Rachael?" Sue says, "You've got a decent voice now, hopefully you can keep it for the shoot." "I think I can, I just have to concentrate until it becomes a little more natural?" "Good girl," they both nod in agreement. "Oh, one last thing, here's a little clutch that Steve apparently got for you. We put some things in it you might need later, lip gloss, a little mirror, hair brush, those sorts of things, and it looks like it already has some identification cards, I think in your name, Rachael Ann Walsh." "Oh, thank you." "Do you have a wallet? Give it to me and we'll have Steve put it in his safe for when you return. You should only have cards in your model name, just to be on the safe side. Maybe your cell phone, too, unless you're expecting calls." I hesitantly give them up as I wonder for second, while we're busy getting ready, exactly how much Steve assumed I'd be agreeable, but I suppose having my ID's in a safe is a good idea, and maybe he made these new ones up for whoever he could get. I can also see getting cell calls to Mark, and having to change voices and such. Probably a good idea to give that up, too. I don't have more time to think on it. We walk out to the main room and Steve again gives a sigh, "She really does look great, just like... I'd never kno...." Jeannie cuts him off, "You'd never know what, Steve? How nice our girl is here, how cute she looks, how she cleans up so well? As you said when we went into the changing room, she is Rachael Ann Walsh and nobody else. Please don't forget her name or who she is. Okay? She deserves every bit of respect and consideration that you can offer, and maybe some more. She is, to you, a model, whom you have hired and we have helped get ready." I'm seeing something in his eyes, the way he's standing there and looking at me, it's not at all like he's leering at me or staring. It's something deeper, but before I can think any more on it, he continues, "I...I'm sorry. Rachael, I meant to say that you are even more gorgeous than I could have imagined. You are just perfect for this modeling job, I'm very happy you accepted. But, I'd like to get a few head shots right now, I think it will be important later and I'll tell you why when we're in the car." "That's better." Finally putting those thoughts I just had out of my mind, forcing myself to understand that this is a job and it's only for a few hours at best, I say, "Thank you, Steve, and thank you for asking me to do this, I think this will be a very enjoyable day. How would you like me to pose?" He gets several shots in and uploads them to his computer. Between shots as he's fiddling with his camera, reviewing the pictures, he asks, "So, Rachael, do you have any plans for this weekend? Anything really great?" I reply, "No, I don't think so? I started my two week vacation today, so this is really working out. I was going to catch up on chores, and thinking of maybe going to see some friends later next week. Perhaps just sleep in the first few days. Why do you ask?" He pauses a second before responding, "Well, as attractive as you look, and if, um, today works out like I'm now thinking it will, I'd imagine there could easily be some more modeling jobs. If you're interested?" Oh, my, I hadn't really thought about that possibility, as I reply, "I don't know, I..I'll have to see how it goes, I guess?" "Okay, so now I need you to look over there and a big smile." As he finishes and is packing up his equipment, a limo pulls up and Steve says, "Our ride is here, the client sent around a car to make sure we get there on schedule. Let's go, girls." I say a quick good-bye to Jeannie, thanking her for her help this morning in getting me ready, but, of course, we will see each other later this afternoon. We three get into the limo with Steve holding the door for me and Sue, with Jeannie heading off to where she has to be. The limo is quite fancy with a well-dressed driver and an intercom radio between us and him which we can turn off our side, although still hear him. On the way, Steve explains the head shots, "Just to be on the safe side, and protect Rachael, I created two web sites. The first from a while ago, for the Johnson/Martin Group, which is an actual registered small talent agency out of which Rachael here is from, with whom I do business, so that she'll show some representation. It's a very small agency and still relatively new. Then, I also created a Facebook page for you, Rachael, where I'll put the headshots, so it looks like you're an up-and-coming model. That way, anyone doing a search, will find you on the internet. I just have to transfer the pictures from my cloud storage to the site to get it started. Oh, and I see you have your clutch, I put some ID's in it for you, and a little cash, in case you might need something. " "Thank you, so much. My goodness, you're thinking of everything!" "Yep, in case someone wants to know a little more about you. They expect a model from an agency, even a small agency, and now you're that. I have a contract back at the office that I'll give you a copy of when we get back, which is just a standard boilerplate one, nothing unusual I haven't told you. Which means you'll be paid standard hours for the shoot. The agency has been around, just newly on the internet." "That's so smart of you, Steve. I do hope this shoot goes well and gives you the chance for more business?" "I do, too. But looking at you, and thinking of how I'll do the shoot, I really think the client will love it. Just to brief you two, and I'll let Jeannie know, starting when we get there, we're just shooting you, Rachael, in several poses and outfits. I think the one you're wearing will work as a starter, as well as several of the more summery, nautical themed ones, and maybe the swimsuit. You did bring it, Sue?" "Yes, I did, and a number of other changes depending on what you're looking for." "That's good, thanks. Sue here, now, and then Jeannie later will be the set assistant, helping me and you, Rachael, as needed. The client was only willing to pay for me and one full time assistant besides the models, so it has to be just me and one of the two girls to help you through the day." Still thinking on what Steve said a moment ago, I say, "That should be fine, I'd think. I just know I shouldn't have suggested a swim suit." "No, I'm glad you did, now that I see you, I think it'll look great on you, and be perfect for the setting. Anyway, we'll break for lunch around 1, Jeannie will replace Sue, and then at 2 the other models will show up, the men, and we'll get the rest of the shots. I want to get some at different times of the day because the lighting changes, and you can never be sure of the weather by the water." "Um, what time do you think we'll be finished?" I ask. "Well, probably after sunset, as that's the last shots I want to get in. So, that's a little after 8 or so, I think this time of year." "Oh, my, that's a little later than I thought, but I guess it's okay? Where will I be when you're not needing me?" "Of course, you'll need to stay close, because even though I don't think I'll need you for a lot in the afternoon, it may be here and there. Anyway, I asked for two changing rooms on board, one for the guys and one for you, which of course includes Sue and Jeannie. I hope that's all right with you both?" Sue readily agrees, so I do also. He continues, "So you can stay there or if you want, you can hang out on deck and watch. I'm, um, glad that you're okay about staying a little later. We may finish up earlier, though probably not, it'll just depend, I guess. Are you okay with all that?" "Yes, I am. I'm so glad I can help you out, and I hope this will all work out for the best. Just, please remember our agreement, little if any contact with others?" "I'll remember. And Rachael, I just can't get over how attractive you look. I'll say it again, if you are interested in picking up some extra money as a model, please let me know, at least first before you go with anyone else. If I don't have a need for you, I'm sure I can contact others who will easily." "Um, maybe we'd better see if I actually work out? I am doing this as a favor to you, I don't think I'll really want to go anywhere else. Well, at least at this moment, anyway," I sigh and continue, "And if this does work out, and there's no embarrassment anywhere, I guess I would consider doing this again...but most likely only with you and only on a very limited basis." "Okay, I can understand, we'll see how this shoot goes and then take it from there." "I guess that will work. Oh, I do have one question?" "Okay." "Sue, here, and Jeannie besides, are, um, both attractive; couldn't either of them have filled in for the model that couldn't come? I would think it would have been a little easier than getting me?" Steve takes a breath as both women smile at him, "I did ask both, but Sue here as an appointment she can't break later this afternoon, and Jeannie has some engagements around noon but would have gotten out of them, as a last resort, only if you hadn't volunteered." Sue takes my hand and says, "Rachael, dear, when Steve showed us the pictures he took of you, in your acting role and then when you had changed back, Jeannie and I both agreed that we wouldn't even be in the same league with you if we got the chance to work on you. And we were absolutely right. This is so you. You are perfect." I can barely say with an embarrassed smile as I nod my head, "I see, thanks." This is putting me in a little bit of a daze, to have such positive confirmation that I'm passing as a young woman. Soon enough, we get to the docks, right at 11, and are dropped off near a slip with a quite large sailboat, very shiny and new, a real luxury looking boat with two

Same as Sailing Into Uncharted Waters Videos

2 years ago
  • 0
  • 28
  • 0

Sailing with my daughter and friend by bstrbrwn1

Sailing with my daughter and friend by bstrbrwn1Fantasy, Cheating, Consensual Sex, Cum Swallowing, Exhibitionism, First Time, Male / Female Teens, Oral Sex, Virginity, YoungIntroduction:It's mostly innocent out on the water.Most people understand how mistakes happen and how things can easily get out of control.If you're a guy and there's a beautiful woman trying to seduce you, sometimes our moral compass gets stuck.I am a pretty happily married 44 year old man. I married a wonderful woman 18...

2 years ago
  • 0
  • 22
  • 0

Sailing with my daughter and friend pt2

Here is a quick recap for "Sailing" part 1. I had a one-time tryst with my daughter’s best friend before we learned that she was moving out of town. After Sara left, my family went sailing a few more times before fall set upon us and forced me to take the boat out of the water for the winter. The sailing was still enjoyable, but I will admit I missed it being just the 3 of us for our special sailing times. My wife was always delighted to be on the water with us and tried to cheer...

2 years ago
  • 0
  • 22
  • 0

Sailing with my daughter and friend

If you're a guy and there's a beautiful woman trying to seduce you, sometimes our moral compass gets stuck. I am a pretty happily married 44 year old man. I married a wonderful woman 18 years ago and have a wonderful 17 year old daughter, April. As with most marriages, there are good days and bad days. Sometimes we feel neglected and other times the king of the world. Though, for the past several years, a certain area of my marriage has been diminishing, Sex. Though my wife and I...

1 year ago
  • 0
  • 13
  • 0

Whiskey JackChapter 5 Uncharted Waters

Zelda awoke from a troubled sleep and lay still for a moment longer to enjoy how great it felt to wake up in a bed that felt good to lie in. She stretched her firm body and soaked the comfort up from the luxury of a bed with no lumps or sags. The caress of the silken nightwear Jack had insisted she buy felt wonderful to her skin. No, it was beyond was beyond wonderful. Zelda felt pampered for the first time in her life. "Oh yes, Jack was right," she whispered to herself and smiled. The...

3 years ago
  • 0
  • 23
  • 0

Sailing With My Daughter and FriendChapter 2

Here is a quick recap for “Sailing” part 1. I had a one-time tryst with my daughter’s best friend before we learned that she was moving out of town. After Sara left, my family went sailing a few more times before Fall set upon us and forced me to take the boat out of the water for the Winter. The sailing was still enjoyable, but I will admit I missed it being just the 3 of us and our special sailing times. My wife was always delighted to be on the water with us and tried to cheer April up....

3 years ago
  • 0
  • 22
  • 0

Sailing Adventure 1

Dave and his wife, Marsha, are attending an afternoon cookout one Memorial Day weekend. Dave is twenty-seven and Marsha is twenty-six. She is a vivacious five-seven with medium-length blonde hair and nice full kissable lips. He’s a few inches taller at five-ten. They have been married for a couple of years.The cookout is taking place at a large house in an upscale neighborhood. Out by the pool, with beer in hand, Dave is talking to Kurt, the CEO of a local tech company.They are admiring Dave’s...

Wife Lovers
4 years ago
  • 0
  • 22
  • 0

Sailing Lessons Pt 3

I walked into the dining room of the lodge, and hung my raincoat up on the coat rack. Albert and Edna were sitting at the table next to the kitchen and waved at me to come and join them. Judith was sitting to the left of Edna, working on a plate of pancakes. I grabbed myself a cup of coffee and sat down across from the three of them. Albert was just finishing a bowl of cereal, and Edna was just sipping coffee."Pretty drippy day today, eh?" Edna observed."Yeah," I replied, stirring some cream...

Taboo
2 years ago
  • 0
  • 34
  • 0

Sailing Date

Julie glanced out the window and saw a vision walking toward the restaurant. He was tall, with long black hair, and well-defined muscles with the body of a gymnast rather than that of a weightlifter. He had the dark complexion of one of the Mediterranean countries. He was the hottest guy she had ever seen. “Sally, if ‘Mr. Bangable’ comes up, seat him in my section,” Julie told her coworker.She and Sally were two of the three girls on staff today. The small lakefront town had a shortage of...

Teen
4 years ago
  • 0
  • 32
  • 0

Sailing Lessons

I had taken two weeks off to vacation at the lake. It was going to be sort of a working vacation, since I would be working on Uncle Ed's cabins. Uncle Ed is my wife's uncle, who has more money than he knows what to do with. He owns a whole resort on the lake, complete with about twenty cabins. He usually sets aside ten or so cabins in the middle of the summer for all of the shirt-tail relatives to use and a sort of loose family reunion ensues every summer.This summer was a little different for...

2 years ago
  • 0
  • 26
  • 0

Sailing Into Adulthood

I got my love of sailing from my Dad; after he and Mum split up when I was about seven, he moved out to the coast and returned to his first love, sailing.Now I'm seventeen, for me it is perfection. An apartment on a marina complex, so you are right by the ocean. It's got a big supermarket, ship’s chandlers, a few tourist shops because it’s a local attraction and a bar-restaurant.I saw one of the other residents, Cass, staring up has her first-floor apartment.“Hi James, you don’t have a ladder...

First Time
3 years ago
  • 0
  • 20
  • 0

SAILING SURPRISE

aI Am Turned On By Wife Sharing Sailing Suprise I'm at the helm of a 60 foot racing sailboat on a bright sunny day with a gentle southwest breeze blowing across the deck and filling the sails. I have always dreamed about doing this and now here I am steering this vessel while the ships crew and captain are in the cabin having lunch. I really need to start from the beginning so you will understand the SURPRISE. Karen (wife) and I were living in PNCLA while I was in school training for a job...

2 years ago
  • 0
  • 44
  • 0

Sailing

Sailing It had been a long winter and I was looking forward to sailing my sixty foot sail boat out into the Caribbean Ocean as in the last month I had filled the water tanks, shopped for food for a three week supply and made sure all the sails were in excellent shape. I needed at least one other person to help me get the “Lucky 13” out into open water as I would use the engine to power out past the jetties. The “Lucky 13” and I went back a few years as I bought it as a project and a place to...

3 years ago
  • 0
  • 19
  • 0

Sailing

Drew and Teri are our neighbors. I’m Jim and my wife’s name is Linda. We’d been married for two years when these events took place. I’m an attorney and Linda worked part time at a plant nursery back then. Drew is retired from the airline industry and Teri stays home or goes and does what she wants. Sometime during our first week here, Teri and Drew appeared at our door to introduce themselves, and Teri brought us a nice apple pie. She invited us to dinner with her and Drew the following...

4 years ago
  • 0
  • 26
  • 0

Sailing Lessons Pt 2

She started down the ladder and then looked back to see if I was coming. I started after her. As I stepped down into the cabin, Audrey was in the galley at the bottom of the stairs, searching through her backpack. She turned around as I reached the bottom of the stairs, which put her nose to nose with me. She looked me right in the eye and smiled.“That was really close.”“Yeah,” I said, “That might have been a little embarrassing.” (That was an understatement.)She leaned forward and gave me a...

Taboo
3 years ago
  • 0
  • 21
  • 0

Sailing Adventure 2

The next morning Dave and Marsha get up early and drive down I-95. They start to relax as soon as they leave the interstate and take the road leading down the Northern Neck between the Potomac and Rappahannock rivers.Marsha tells her husband, "It is so great to get away. I am already feeling more uninhibited."Dave replies, "I am too. This is going to be a great weekend." He glances at his wife's full breasts in her top and fantasizes about Marsha showing Kurt more of her body in her bikini.They...

Wife Lovers
2 years ago
  • 0
  • 26
  • 0

Sailing to Australia

We were now the three musketeers, that would be me, David Miller, Carol my wife and our business partner Ted Williams. On this truly gorgeous spring day in southern California we walked hurriedly down the wooden dock toward the object of our desire, to the temporary slip where she awaited us We walked in hurried eager steps along what seemed to be a never ending path, until we finally rounded that last turn. And there she was. God she was beautiful, and sexy, a 51 foot Beneteau, a French built...

2 years ago
  • 0
  • 35
  • 0

Sailing Lessons Pt 1

I had taken two weeks off to vacation at the lake. It was going to be sort of a working vacation, since I would be working on Uncle Ed's cabins. Uncle Ed is my wife's uncle, who has more money than he knows what to do with. He owns a whole resort on the lake, complete with about twenty cabins. He usually sets aside ten or so cabins in the middle of the summer for all of the shirt-tail relatives to use and a sort of loose family reunion ensues every summer.This summer was a little different for...

Taboo
3 years ago
  • 0
  • 23
  • 0

Sailing

Sailing Janet L. Stickney [email protected] My friend Bill and I were as close as brothers, having virtually grown up together, and we each thought we knew everything there was to know about the other. Because we rarely held a secret from each other, I felt very secure in the knowledge that I held one thing very secret to myself. Bill has a sister that is two years older than we are, and is a total pain. On the other hand, I have two sisters, Karen, and Kathy, both older than I...

2 years ago
  • 0
  • 30
  • 0

Sailing Quiet Romance

Sailing – Quiet Romance This is a little tale about an experience I had a while ago. But first, let me introduce myself, and also mention that all characters herein are consenting adults. The names have been changed in an effort to circumvent unnecessary persecution. I’m an ‘older’ guy, recently retired, living on a barrier island in the Gulf of Mexico, off the southwest Florida coast. I enjoy leading an active life, and try to stay fit by walking, bike riding, swimming and sailing on the...

Mature
3 years ago
  • 0
  • 27
  • 0

Sailing Lessons Pt 4

Judith stretched out beside me and propped her head up."So are you," she said, and leaned in to give me a kiss. And what a kiss it was! It started out a little tentative, but she turned up the heat in seconds. In no time at all, Judith had wrapped her arms around my neck and pressed her warm body to mine.Instinctively, my left hand had found its way to her back and was caressing her smooth skin, sliding downward and cupping the firm cheek of her ass. I rolled a bit to my right side so I could...

Taboo
4 years ago
  • 0
  • 17
  • 0

Uncharted Territory

As Matt sat there dreading this horrid day that was inevitable his thoughts came crashing back down to reality by the sound of his mother’s voice calling for him from the kitchen downstairs. “Matt your breakfast is getting cold, get a move on or you will be late on your first day.” Giving out a huge sigh he rolled out of bed and made his way to the bathroom where he took a shower and went through his usual morning routine in getting ready for school. He made his way down stairs and sat...

2 years ago
  • 0
  • 23
  • 0

Sailing Lessons Pt 8

Holy Crap! There was a boat pulling up next to the Princess! I jumped up and pulled my shorts on and tugged the t-shirt over my head. I ran up the steps and out onto the deck to find Aunt Edna and Uncle Albert idling towards the Princess in their fishing boat.Holy Crap!In an inspired move, I grabbed both Audrey and Judith's packs without Edna and Albert seeing them and pitched them down the stairway. Then I went to the stern and waved at Aunt Edna and Uncle Albert."Hey!" I yelled. "What are you...

Taboo
4 years ago
  • 0
  • 31
  • 0

Sailing Adventure 4

Enflamed with lust after her husband offered her pussy to the captain, Marsha tells the crew, “I know the captain wants my pussy, since this is his boat, he gets the first turn.”Marsha slides over to Kurt. "Captain do you like my pussy? Did the crew tell you I have a nice little bush? I know you felt it this afternoon. Play with my tits like you did before."Kurt starts fondling her breasts again. She is very vocal and starts talking dirty. She leans up against Kurt and spreads her legs for the...

Wife Lovers
3 years ago
  • 0
  • 24
  • 0

Sailing Sweethearts

My neighbor’s two daughters have gone from giggling girls to young women during the time I’ve lived here. We’ve always been friendly since I even babysat for them when they were younger. They’re always welcome to use my swimming pool and I’ve enjoyed watching their young bodies develop, especially with the swimsuits which kept getting briefer and briefer as they matured. I’d gone half with a friend on a 35-foot sailboat in a big lake about an hour away. It had been years since I’d been able to...

3 years ago
  • 0
  • 25
  • 0

Sailing Chapter Three

Sailing Chapter ThreeThe next morning I awoke to find Linda and Janice no longer in bed and the covers were no longer on the bed as I lay there naked in the middle of the bed. The sounds of the boat resting in harbor as the sunlight streamed through the portholes helped bring me fully awake as well as the erection between my legs. I rolled off the bed and walked out into the galley not to find them and I went topside through the cockpit and found Linda sitting spread eagle on the cushions with...

2 years ago
  • 0
  • 24
  • 0

Sailing Weekend

It was an old building and the south facing windows reached from just below the ceiling to about two feet off the floor. The manager's secretary, Susan, a very pretty natural blond with a good figure, was twenty eight and single I was forty six. She used to dress well and demurely but she obviously didn't wear petticoats under her long summer dresses and skirts. It was a real treat when she was standing in front of the windows as the outline of her body showed through her dress so that it...

3 years ago
  • 0
  • 22
  • 0

Sailing Sun and Sex Part 3 Erotic Sex in the

It's Monday and we have a wee lie in after the previous days travel and sexual exertions. Eventually rising at 10, we shower and have a light breakfast before climbing up the hill to the old village which clings precariously on the edge of a steep wooded hillside. It's a twenty minute haul but well worth the effort. The views from the small taverna's veranda are spectacular taking in the many beautiful islands dotted around the crystal clear sea and the mountainous mainland.Drinking fresh...

3 years ago
  • 0
  • 28
  • 0

Sailing Lessons Pt 7

I spent the next forty minutes getting all the connections made in the North cabin, and went back to my cabin to clean up. I put on a clean shirt and shorts and headed down to the marina. When I got to the Princess, I found Audrey on the boat, tidying things up. "Welcome aboard Captain!" she said. "I think we're all ready to go.""Great!" I said. "Just let me check the engine, and we can cast off.""I think Judith already did that." Audrey said. She went to the door of the cabin and yelled down,...

Taboo
1 year ago
  • 0
  • 19
  • 0

Sailing We Will Go

Copyright© 1995-2003 "There was a young sailor from Brighton Who remarked to his girl, 'You're a tight one.' She replied, 'Pon my soul, You're in the wrong hole; There's plenty of room in the right one.'" -author unknown The slight westerly breeze promised a wonderful start to a week of sailing. The six-year-old sloops sails caught the wind only moments after leaving the breakwater. The forty-eight-foot ship creaked as the wind pressed it to starboard and the few...

3 years ago
  • 0
  • 26
  • 0

Sailing Lessons Pt 6

As I approached the door of Uncle Ed's cabin, I noticed that all the shades were drawn and the interior was dimly lit. I knocked on the door and Audrey answered it and let me in. I was stunned at the sight. Audrey was dressed in a tiny little French maid's costume, no doubt something she'd found in the bottom drawer of the dresser. She was stunningly beautiful. She had put her hair up and had applied makeup that transformed her already pretty face into drop-dead gorgeous.The costume fit her...

Taboo
2 years ago
  • 0
  • 20
  • 0

Sailing Lesson

"Now, what would you do if you were in mid Channel and one of your crew is taken ill, he's in a lot of pain, can't move, has difficulty breathing and his face is very red?" She asks "I'd send out a 'Mayday' on the VHF," I promptly reply, looking smug. "Your electrics are down and it won't work," she replies Ah, now that's a bit of a bugger... let's see. "Well, um... I'd ask one of the other crew if they were a doctor?" I hazard. "Don't be facetious, on a boat this size...

4 years ago
  • 0
  • 23
  • 0

Sailing Sun and Sex

We board my 50 foot yacht, 'Adios', at lunchtime after a long early morning flight to Levkas. It's quite hot, 32 degrees, and instead of staying put we decide to sail down to Spartakhori, one of my favourite spots. After shopping at the mini-market and a quick snack at a teverna on the quay we return to the boat, cast off the lines and motor southwards down the Levkas Canal to the Ionian Sea.There are just the two of us, Suzy, my new girlfriend, and me. This is Suzy's first sail, she's a little...

2 years ago
  • 0
  • 30
  • 0

Sailing With Mom

My name is Kyle and I'm 20 years old. I've recently taken up sailing. When I told my mother about it, she was very interested in my new hobby. "I think we should go sailing, just the two of us. It'll be great!" she told me over the phone. "But, Mom, you're nine months pregnant. Are you sure your stomach can handle the open waters?" I asked. She hadn't had a child since giving birth to my twin sister and me when she was only 16. After talking to my father, they agreed to have another...

2 years ago
  • 0
  • 32
  • 0

Sailing Holiday

This happened a few years ago and is completely trueWe were on a sailing holiday and had chartered a 36 foot yacht in Croatia. I don’t like wearing clothes and sailing in a warm climate is great for naturist.Our normal plan is to sail to a lunchtime swim spot and move on to a more sheltered anchorage for the night, planning our lunch departure to arrive in daylight. Normally there is time for another swim then get showered, Gin and Tonic evening meal out or on board depending on where we are....

4 years ago
  • 0
  • 22
  • 0

Sailing away

Somewhere in the Mediterranean Sea, close to any of the thousand Greek islands, a white silhouette breaks the waves. My old sailing boat, not too big, not too small. The sails fully extended and the wind is gentle but constant. I'm at the steering wheel and you are mixing us some drinks. I look at the horizon while you take off your dress and try to get some sun. Your white skin is too sensitive you ask me to apply some cream on your back. I put the boat automatic pilot on and proceed to grab...

Straight Sex
2 years ago
  • 0
  • 24
  • 0

Sailing Quiet Romance

Sailing – Quiet Romance This is a little tale about an experience I had a while ago. But first, let me introduce myself, and also mention that all characters herein are consenting adults. The names have been changed in an effort to circumvent unnecessary persecution. I’m an ‘older’ guy, recently retired, living on a barrier island in the Gulf of Mexico, off the southwest Florida coast. I enjoy leading an active life, and try to stay fit by walking, bike riding, swimming and sailing on the...

3 years ago
  • 0
  • 26
  • 0

Sailing Chapter 2

Sailing Chapter TwoWe spent the next two days out at sea and the weather had become overcast as we sailed on into the open ocean waters. The soft breeze filled the sails and sitting back in the cockpit with Linda as we sailed out into the open waters I had plotted on the charts our path to another small island I knew had fresh water and a place to drop anchor. The island had a small community of open minded people who lived like natives, but had shelters built to survive any massive storms...

2 years ago
  • 0
  • 19
  • 0

Sailing in the Gulf

As I readied the boat, I couldn’t help but hear your entrance to the docks. Voices quieted and men watched with approval as you walked down the dock. Women were barely envious and some were attracted to your stroll on the pier. I raised my head to watch you for a moment. The curve of your legs in those 3 inch sandals was fantastic. I caught a brief glimpse of your neon yellow bikini bottoms as the wind caught your thin coverup. The coverup was more of a tease, but I enjoyed the view of your...

3 years ago
  • 0
  • 26
  • 0

Sailing Adventure 3

Kurt comes back on top with a beer. Marsha is still sitting with her shirt open and breasts partially exposed. She feels so free and uninhibited.Dave stands up and stretches. "I'm going down below for a while.""OK, honey. Why don't you take a little nap? I'll stay up here and relax with the captain."She feels the heat and intimacy of being alone with Kurt. Marsha takes off her shirt. "There, that's better, don't you think? You can look at my tits all by yourself.""Come here.""That sounds like...

Wife Lovers
2 years ago
  • 0
  • 29
  • 0

Deep Waters

Deep WatersChapter One        Charlotte Elizabeth Waters stood at the prow of the ship, near the bowsprit, enthralled with the azure seascape before her.  The crystal blue expanse of the Caribbean turned to froth as the ship cut through the sapphire waves, the creaking timbers and taut rope that held the booming sails flashing whitely behind her.  She breathed deeply, filling her lungs with the salt breeze and she vibrated with the barely contained excitement of youth’s first step upon the path...

4 years ago
  • 0
  • 19
  • 0

Sailing away

Somewhere in the Mediterranean Sea, close to any of the thousand Greek islands, a white silhouette breaks the waves. My old sailing boat, not too big, not too small. The sails fully extended and the wind is gentle but constant. I’m at the steering wheel and you are mixing us some drinks. I look at the horizon while you take off your dress and try to get some sun. Your white skin is too sensitive you ask me to apply some cream on your back. I put the boat automatic pilot on and proceed to grab...

3 years ago
  • 0
  • 24
  • 0

Sailing out of Oyster Bay

We chartered a sailboat out of Oyster Bay, leaving the channel markers behind us and headed north with the wind in our sails. The next course of action was refreshments and letting the wind gods grace our bodies. Anne went for the beers and I kept the boat on course while taking off my clothes. Anne returned with the cold ones and handed them to me so she can follow suit or should I say suitless… We spent the mid morning sunning ourselves and working on our allover tans while enjoying the...

2 years ago
  • 0
  • 19
  • 0

Sailing out of Oyster Bay

We chartered a sailboat out of Oyster Bay, leaving the channel markers behind us and headed north with the wind in our sails. The next course of action was refreshments and letting the wind gods grace our bodies. Anne went for the beers and I kept the boat on course while taking off my clothes. Anne returned with the cold ones and handed them to me so she can follow suit or should I say suitless… We spent the mid morning sunning ourselves and working on our allover tans while enjoying the...

Exhibitionism
4 years ago
  • 0
  • 19
  • 0

SailingChapter 2

Sailing: the Coast Guard Bored? ... I am. Every Saturday it's the same thing. Start when they tell you. Politely curse because one of the Chicago rich kids cut you off. Sail up the lake, turn at the buoys. Tack back and forth into the wind. It's always the same ... over and over. What happens if you win? Is there money in your pocket? A trophy for the shelf? No? Your crew picks you up and throws you in the water. Never race with your wallet in your pocket ... if you win it's sure to get...

4 years ago
  • 0
  • 21
  • 0

Sailing out of Oyster Bay Part 2

We were relaxing in the cockpit. Anne heared a splash and turned around to see the other boat close by. It turns out that one of the guys dove into the water. She looked at me funny and asks how long have they be there. I smile and indicate a while. Anne turned red in the face and asked if they saw anything. I suggest that I wasn’t sure with a quirky smile on my face. (Anne loves nude sailing but she is a little shy when others are around) The guy in the water throws his swim suit onto the...

4 years ago
  • 0
  • 22
  • 0

sailing baseball and TS dates

Shelly and I had been chatting online for almost two years. We had share a great deal of personal information and shared in each others personal triumphs and tragedies. She lived in Seattle Washington and I was in Oregon in the sleepy hamlet of Lewisburg. Often we had talked about meeting and each of use has passed close but not arranged to meet. My issue was long term relationships are always prone to fail and she was , by her admission , looking for someone closer to home as well. I have a...

4 years ago
  • 0
  • 23
  • 0

Sailing out of Oyster Bay Part 2

We were relaxing in the cockpit. Anne heared a splash and turned around to see the other boat close by. It turns out that one of the guys dove into the water. She looked at me funny and asks how long have they be there. I smile and indicate a while. Anne turned red in the face and asked if they saw anything. I suggest that I wasn’t sure with a quirky smile on my face. (Anne loves nude sailing but she is a little shy when others are around) The guy in the water throws his swim suit onto the boat...

Exhibitionism
2 years ago
  • 0
  • 27
  • 0

Uncharted territory chapter 3

A few weeks went by and nothing more than a few awkward glances happened between the two as James was around more often now. This frustrated both Sally and Matt beyond what words could explain as neither of them said it but both felt the uncontrollable desire to ravish each other on site. Their frustration grew as the days passed which caused Sally to get tired of being a house wife waiting to get fucked by the stud so she went out and found a part time job being an office temp. She really...

1 year ago
  • 0
  • 21
  • 0

Uncharted territory chapter 2

6:30am the alarm goes off… Matt woke up to the sound of his alarm. “Oh crap, not another day coming to knock me down.” Matt was not enthusiastic about his new school to say the least. His first day had progressed without incident but he knew his luck would run out sooner rather than later. It always circled back to the same old story of him being the new kid and being beaten up by the football players when teachers weren’t looking. Matt knew he should’ve told someone about being...

3 years ago
  • 0
  • 18
  • 0

Uncharted Space

Tony Gibson started heading down the corridor to the docking bay as he wore his dark blue jumpsuit that had a pair of yellow stripes at the end of both sleeves as he was 6'1" tall with light brown wavy hair that was just past shoulder length. As he passed up other crew members along the way as Tony Gibson approached the silvery white metallic sliding door as his right reached up for the scanning device as each crew member had a small chip within the palm of their hand that controlled the...

1 year ago
  • 0
  • 18
  • 0

Uncharted Territory

Of all the activities that Cal Markus imagined he'd be doing on his summer vacation, this was not one of them. Here he was in his longtime friend John's attic wearing an almost sheer pair of black silk panties over a pair of black crotchless pantyhose and seated in front of a large lit makeup table as his friend was busily bustling around the room depositing items of makeup on the table.The sensation of the silky panties against his skin was unbelievable as was the sight of his cock pushing...

Crossdressing
3 years ago
  • 0
  • 26
  • 0

Uncharted Territory Part 2

Cal couldn't believe what he had done, he just tongue kissed his best friend and he liked it. Maybe it was a result of the makeup and lingerie that his friend had dressed him. Whatever the reason. Cal really liked it."So are you ready to fuck this pretty girl in the butt?" His friend, John asked and Cal asked himself the same question.When his friend John suggested it, Cal was not put off as he thought he'd be. He knew about anal sex from the videos on the internet but was he ready to do it for...

Crossdressing
2 years ago
  • 0
  • 16
  • 0

Uncharted Territory The Conclusion

Cal was up earlier than normal for a vacation day and was in and out of the shower long before his parents woke. As he waited for the coffee to finish brewing, he wondered what the day would bring. He also thought about the dreams he had last night and hoped it was a premonition of things to come.In his dream, he was clad in the softest and silkiest lingerie imaginable. Cal saw himself in a black bra trimmed with delicate black lace and a garter belt that matched. The garter belt held up a pair...

Crossdressing
3 years ago
  • 0
  • 49
  • 0

Uncharted Drakes Demise

“Keep on ‘em, men! Do not let those Spanish dogs escape!” Standing at the helm of his beloved ship, Sir Francis Drake sailed with the skills and determination befitting the most seasoned veteran of the British Navy. The Spanish galleon he now trailed was fast, faster than most, but was still no match for the legendary Golden Hind. As the winds remained in his favor, Drake was easily able to keep his ship directly on course, constantly gaining ground on the Spaniards. All the while, his men...

4 years ago
  • 0
  • 17
  • 0

Donjeta and the SeaThe Uncharted Isles

Any direction was fine that the wind might blow, as long as it blew. We had no idea where we were or where safety might lie. It came from the west, strong and steady. We set our sail and let it speed us along. We passed among rocky islands, but we did not beach our ship. We had too few men to work the oars and put to sea again. One of the sailors, the oldest, Agapios, carefully steered us, keeping to the free channels. We studied the coasts, looking for a harbor, other ships, a village, any...

3 years ago
  • 0
  • 13
  • 0

Happy EndingsChapter 2 Uncharted Lands

"Fine, not a problem, I'm over at the Gibbons place now, it won't take me long to finish and I'll head right over." Kevin said into his cell phone. "Entire place?" Rick on the phone explained what he wanted surveyed and Kevin promised to head over right away. It was an ungodly hot day. Make that week, he thought. He'd get this job done and that would be it. It was hard to believe sometimes that he did this for enjoyment! He was done for the week, hell for the month. An hour later he...

4 years ago
  • 0
  • 25
  • 0

The Reflecting Waters

Dave had recently purchased an apartment with his new Fianc?e Kim. The building was in the historic district of their city and was nearly 140 years old. A recent developer had remolded the building and added central air, new wiring, and new flooring, but it hadn't completely destroyed the building's classic appeal. The developer changed the plumbing, but didn't change fixtures, including the unique Spanish bronze fixtures and pitch black bathtub in apartment 3C. It was Kim who noticed the f...

3 years ago
  • 0
  • 36
  • 0

Back To The HaremLiving Waters

Tuning out in last period, ReligionTeacher, "...blah blah blah blah class... now... this would be the most significant difference between the Old and New Testament..."GonePlease, Sirs, please don’t take me away from the Harem. You desire me in the baths, wet and wanting? I am smooth, like the oils that dance atop the hot mineral baths, perfumed with rose petals, glistening with flakes of gold and silver. The tubs are carved from solid gemstone. Mine is of rose quarts, pink like my gem. My gem...

Lesbian

Porn Trends