Accidentally Samantha
My girlfriend and I were at the Dock in Keywest for a Snorkeling trip when Jennifer suddenly started complaining about how her stomach was bothering her. This was no surprise Jennifer never wanted to do anything but this time I thought she might go. She said "You go I don't want to spoil your fun ." What could I do, I went, As the 60 foot Catamaran pulled away from the pier she waved then headed back to the hotel.
I am about 28, 5'7" long Dirty Blond hair usually kept in a pony tail, Slightly overweight but not fat. I have been teased about my physic since I was a child. Wide hips skinny waist and heavy in the chest area so much so that the other guys always tell me I need a bra. And practically no body hair, Let me rephrase that. Thanks to Jennifer, No body hair. Yesterday we were over to Fort Monroe beach sunbathing when Jennifer decided that I was starting to burn and I needed Sunblock so she pulled out her bottle and totally rubbed me down with the lotion, Jennifer is one of those people who take things out of there original containers and put it in her own designer containers. Sun block is no exception. After about 5 minutes I felt a burning sensation and decided it was time to go into the water. As I entered the water all of my body hair just rinsed away. It was a good thing I stuffed the hair on my head up under my hat. My leg hair, My chest hair even the hair under my arms just rinsed away. I came back in and asked Jennifer what was in the bottle she took the top off and smelled it and giggling told me she had accidentally grabbed the bottle of Nair. She then had the giggles for most of the day. I was pissed off but that night she kept running her hands over me telling me how much my smooth skin turned her on, I do have very smooth and fair skin. We had the best sex we ever had.
Back to the Sail boat, On a snorkeling trip they sail you out to the coral reef for an hour then you have an hour of swimming and diving then you sail back, On the way back they provide you with all the beer and wine you can drink. It was a beautiful day the sun was shinning there was enough wind that the Catamaran was sailing at a nice clip. I had removed my shirt and was sitting with two middle aged couples, We were engaged in some nice conversation when a gust of wind took my Tee Shirt over the side. It was a nice day so I did not care and moved up front. When we finally arrived at the Reef I was more than happy to get in the water the swimming was wonderful I saw giant schools of parrot fish, Barracuda, Coral heads. All at once the waves and the wind kicked up a little. And we were asked to return to the boat. In the middle of the boat they drop a stairway down. You swim up and take off your swim fins and then climb on to the stairway then walk up on to the deck, That is what you are supposed to do, What I did was take off my fins and try to step on to the stairway when the boat shifted and the stairway moved in such a way that it totally ripped off my bathing suit which then sank like a rock. What was I to do, I covered myself with the swimfins and made my way to my beach bag as the crew giggled at me I looked into my beach bag hoping that Jennifer had packed me and extra pair of shorts. Much to my dismay all I found was a Postage Stamp size towel and one of Jennifer's frilly sundresses. While trying to cover myself with the fins I tried to arrange the towel in a concealing manner. Finally I gave up and decided to try on the sundress as I unfolded it and looked on a floral print that was beige and white with two rows of white lace around the bottom and another row around the top and two straps that went over the shoulders. The lady sitting closest to me said she thought I would look very pretty in it and they all laughed. I thought what the hell and pulled it over my head to my surprise it fit perfectly, To perfectly, Just below the breasts was an elastic that acted like a bra pulling breasts up and out. From there it hugged me finally flaring out with my hips dropping in a very feminine flattering manner. I pulled my pony tail out from the back and stood up to pull it down and felt my breasts being shaped in a manner I was not used to. The hem line hung down and I felt the lace caressing my thighs. I looked down thinking how much it turned me on when Jennifer wore this dress and started to get quite aroused and sat back down. The Couples near me were just staring at me. The lady who had heckled me earlier Said "I told you that you would look very pretty in it". Only there was a different tone in her voice the others just nodded. Just then one of the crew came by giving out beer and wine. When he came to me I could see that he did not recognize me as the one who had lost his bathing suit. What he did do was look me up and down and say "Darling what can I get for you". I said "beer" he responded "If I can get you anything else just holler and walked off to serve the others. The lady next to me said "He did not treat us like that". I blushed and decided that I would take my brush and go up on the front to dry my hair and drink my beer. I got up front and undid my pony tail and started brushing out the hair. I do get lots of compliments on my hair, Jennifer once told me if I cut my hair she will break up with me, She don't have to worry. I started to brush it out.
I was standing up against the railing and my hair was dry in no time, With the salt water and the sun and the breeze it dried very soft and flowing. So I stood there with my hair tickling my shoulders in the breeze and the lace tickling my thighs just watching across the boat at the beautiful water and sky when this guy walked up on the other side of the boat and smiled at me. I smiled back not really thinking anything when he raised his camera and took my picture. I was surprised not really comprehending when I looked back and noticed I had drawn Quite a few male eye's looking at me in a way that no male had ever looked at me before. I thought, they must know I am a guy after half the boat had seen my parts and the other half saw me put on the dress and I could not look like a girl. I looked down and saw a very pretty dress, Long slender hairless legs and long blond hair flowing in the wind. And thought these guys are strong swimmers and would still have been in the water looking at the fish and would not have witnessed my depanting, One look back at them and I decided, Yes they do think I am a girl and they want me. Even the guys who were sitting there and knew were looking at a guy. I was embarrassed and looked around and yes a few of them seemed to be aroused. I had dressed as a girl for Halloween before with some success, I had worn my mothers old bathrobe and bathing cap, It was fun. I have also seen pretty girls wearing pretty dresses and fantasized about dressing up like that and flirting with guys wondering how the clothes would feel, But that was just fantasy. I was startled out of my reverie by another guy with a camera, This one the boat photographer the same guy who had served me beer earlier. He said "Excuse me beautiful but could you take just two steps back" He looked in the camera and said "OK now look into the wind, Perfect" he took the picture. Stepped closer and said "That is prettiest picture I have taken all week, Can I have your name" I was horrified and said "Sam". He said "Glad to meet you, your picture will be available one hour after we land at the dock you should come look, Your very pretty". As he left I looked toward the other side of the boat and saw we were starting to get near shore. There were three guys and two girls standing there. The two girls were wearing bikini's and looked away when I caught them staring. The guy in the middle who looked to me to be the unattached one. Borrowed the camera from one of his buddies and walked towards me asked if I would smile for him, I had no choice I also blushed. He then snapped the picture. He also asked if one of his buddies could take a picture of him with me. He did not wait for an answer and walked up and put his arm around me and kissed me full on the lips as his buddy snapped the picture. I was ready to punch him when he got on his knees in front of me and begged for forgiveness and kissed my hand. He then offered to buy me a drink. I was laughing as were his friends by this time and told him that the drinks were free. He said "That's OK I will buy it for you if that will make you happy". I decided to play along for a while then tell him of his error to embarrass him in front of his friends besides much to my surprise I decided that he was cute. He had the body that I always wished I had, Broad shoulders and a skinny waist and a big happy smile, If I were a girl I would think he was Cute. He returned with my drink and said "That was expensive, But well worth it. Did anyone ever tell you that you are beautiful ? And are you here with anyone ?" I replied " I am not on the cruise with anyone, But my girlfriend is back at the hotel room." This cheered him up a bit as he inquired " Would you go to dinner with me after the cruise, And depending on how dinner goes out for a drink after that and depending on how the drink goes maybe back to my place for a nightcap and maybe to spend the night and possibly the rest of your life ?" I said " I guess you believe in love at first sight, You don't know anything about me, Maybe I have a Deep dark secret that will scare you away." He replied "How could anyone as cute as you have done anything evil ?" I responded "I did not say evil, I just said deep and Dark." Just then a breeze came up that almost exposed me for what I was, I then realized this was my fantasy, I was dressed as a pretty girl flirting with a cute guy. He then said " My name is Dave and I have to tell you I have been looking for a girl like you all my life you are a perfect 10 in my book so tell me your secret and then marry me". So I told him" I can tell you my secret, But I cannot marry you. My secret is that when I came aboard the cruise earlier I was a boy". Dave responded "A boy ?" I said "Yes a boy, Or let me rephrase that, A male." Dave said "That's impossible. I need proof." I said "Proof I have, There is always the Crocodile Dundee test." Dave said " I am not quite ready for that yet, But How did you arrive as a boy and end up as the girl I now see in front of me ? Inquiring minds want to know." I related to him the Lost the bathing suit, Girlfriends sundress story, Finishing up by saying that I moved up on the bow to comb my hair because they were embarrassing me below. When suddenly all the males started taking my picture and wanting to marry me. Dave asked " why are your legs and chest shaved ?" So I told him about the Nair incident at the beach the day before.
Dave responded "So your telling me you have never dressed as a girl before and you accidentally ended on the front of a sailboat looking like a centerfold ?" I said " I might have phrased it differently but yes." Dave looked me up and down shook his head and said " You are still one of the prettiest girls I have ever seen, Knowing you are actually a guy turns me on even more, I am not gay and have never been with a guy before but I want you, Would you still have dinner with me ?" I told him I was very flattered but all the money I had went down with my shorts. And I wanted to change." Dave smiled at this and replied "Dinner is on me and I do not want you to change I love you just the way you are." I felt his hand move over and grab my butt. His friends were looking on and winking at him. Dave leaned close and whispered in my ear "if only they knew" I suddenly thought what would Jennifer and everyone else think if they knew I was making a date to go out dressed as a girl. I dismissed the thought thinking this is just to much fun this is the stuff fantasy's are made out of.
The boat docked, Dave insisted on carrying my beach bag. We made our way down Caroline St. the Jimmy Buffet song Woman going Crazy on Caroline St. Ran Through my mind. We walked past Sloppy Joes up on to Duval St. I stopped and called Jennifer and told her that I was going out for a drink with one of the guys I had meet on the boat. Dave said he wanted to take me to Blue Heaven for dinner. We were about to pass a store when Dave suddenly grabbed my arm and pulled me into the store and there in front of me was a full length mirror. The guy I recognized but the pretty blond girl standing next to him in the frilly dress had my face but could not be me ! I moved my hand up to touch my face and the Pretty girl moved her hand up at the same time. I now understood Dave and the other guys reaction, Why I would have gone after me. Dave who had been watching intently said " I now believe you, That reaction could not have been faked and yes you do look like a wet dream." We turned around to find we were in a lingerie shop I looked at the stuff and Blushed, I could not believe what I was thinking I was getting horny thinking about wearing this stuff. Dave pulled me over to a table and lifted up this virginal white skimpy nighty and held it up to me and said "You would look hot in this. By the way if you don't mind my asking what type of Panties are you wearing as he started to tug at the hem of my dress. I told him that all I had was the dress I had nothing on under it. Dave steered me over to a rack and said "A pretty girl like you needs sexy underwear. He picked up a white pair of lacy panties that looked like they would fit and said "how about these ? " I blushed and said "I have no money." Dave responded " I do, This is the most fun I have had in years allow me to buy them for you." A sales girl walked over and Dave asked her "I want these and a matching bra. " I blushed again " The girl turned to me and asked what size." I responded " Uh, I don't know ." Dave smiled and laughed. The sales girl said if you will allow me and she pulled out a tape measure and proceeded to take chest measurements in the process managing to totally feel my breasts up. She finally announced, A thirty six C. I was amazed. She then went to a rack and produced a very frilly white bra that matched the panties. Dave nodded his approval and said "Why don't you try them on.?" the girl pointed to the dressing room in the back and asked if I needed assistance, I declined the assistance and proceeded back I was quite turned on by the whole thing and I did not want the girl to see. Dave said" If they fit good just leave them on. I closed the door and took off the dress. I looked at the mirror as I pulled up the panties, They felt wonderful as I tucked my parts away. The bra I put on backward as I had seen my Girlfriend do and turned it around I put the straps on and adjusted them and pulled my breasts up into the cups, It felt very natural and comfortable as sexy and silky. I looked in the mirror and could not believe the feminine aspect I had assumed. I heard Dave outside say " Can we see ?" I told him, later. I pulled the dress back on. The Bra made the dress look even more Feminine and the panties helped to hide that tell tale bulge. I stepped back out Dave looked on with hungry eye's he passed me some sandals with heels on them and said try these. They fit perfectly as every other thing had today. The sales girl walked over and said Dave explained the situation and you look awesome. If you don't mind I want to try some makeup on you. I agreed, She used a little Eye liner and some lipstick and a little blush.
We all turned and looked in the mirror, The illusion was complete. To all appearances I was not only a girl but a very nice looking one. I said Why can't I get girls that look as good as I do to go out with me ? The sales girl was looking at me with the same hungry eye's that Dave was. She informed me " I will go out with you, You turn me on more that you can imagine." She gave me her business card and said call me. I was a little unsteady on the heels at first but soon got used to them. All the guys were staring at me especially the ones with girl friends. Dave grabbed my hand an I moved over next to him and he put his arm around me to steady me. I found I liked this. He said " Do you realize how easily you have fallen into the feminine roll ? I really do feel like I am walking down the street with my girl friend." He then moved his hand down and caressed my bottom.
I thought if a guy had done that yesterday I would have smacked him, Or would I have ? We reached Blue Heaven and took a seat out side Dave sat next to me and ordered. With all the chickens running around I was glad he did not order Chicken. We sat and talked and had a few beers. After a few minuets I felt Dave rest his hand on my leg. He commented "You have such smooth skin are you sure your not a girl ?" I said " At this moment I am not sure." He moved his hand higher up under my dress caressing my thigh, Finally he reached his target. He looked at me and raised one Eyebrow in a Spock like fashion and said "Fascinating!" As he caressed me through the silken panty material. I thought I would cream right then. At this moment the waiter brought our food and Dave removed his hand from the forbidden zone. As we ate Dave said "You don't know how turned on I am." I said "You do know how turned on I am." For the first time all night Dave blushed. I leaned over to him strategically placing my hand on his lap and kissed him on the lips while grabbing a handful and yes Dave was as excited as I was.
We walked back over to Duval St. And went to Captain Tony's I ordered a Pirates Punch and we sat down to watch the band. David's friends showed up, One of them had stopped and picked up our pictures unknown to me at David's request. We looked at them, I could understand why Dave had thought I was a girl. After a while we got up and danced, Some things are easy being a girl dancing in heels is not one. It took a while to get used to the heels as well as getting used to not leading. I got the hang of it soon. Dave was groping me all over . Eventually we were up near the bar I was leaning back against Dave, He had his arms around my front holding my tits I could feel him pushing my dress between my legs when he leaned down and pulled my hair back and nibbled my earlobe and suggested we adjourn back to his room for a nightcap.