Accidently Samantha free porn video

Accidentally Samantha BY Karen Flynn [email protected] 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 and heavy in the chest area so much so that the other guys always tell me I need a bra, 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 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 them 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, chest hair even the hairs 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 t-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 Parrotfish, Barracuda and 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 an 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 hemline 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 mother's 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 cloths 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 bikinis 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 too much fun this is the stuff fantasies 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 guy's 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 Eyeliner 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 also 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 eyes 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. We stepped outside of Captain Tony's and David flagged down a Taxi. Once we were in the Taxi David's hands were all over me. I told him to stop. He said "Just like a girl". I responded " You are behaving just like a guy." The Taxi drivers Eye's were glued to me in the mirror, For the first time tonight I felt a little nervous. David sensed this and backed off a little. The Taxi pulled up in front of the Blue Marlin hotel. He paid the Driver and we walked into his room. As soon as the door was closed he pulled me to him for a full body kiss. After we broke I felt a little weak in the knees. He turned me around and pulled my hair to one side and started to kiss me on the neck and nibble my ear lobes while holding my breasts and pinching my nipples. I could feel his cock pressing against my backside reaching around I felt him through his shorts. He murmured in my ear "Oh baby, It's so hard to believe you are not a girl." I went to turn around he removed his Tee Shirt as I turned to face him. I reached down and undid his shorts and dropped them to his ankles. His cock was pointing straight at me. I looked down and it was longer and thicker than mine I reached down with both hands and grabbed hold of him. For the first time in my life I was holding another mans cock in my hands. It was silky smooth and hard yet kind of spongy a lot like mine only bigger. I had another momentary lapse of guilt, What would my parents think. I pushed this thought away. This was too much fun and too horny to be bad. David asked " Do you like it?" I said, "No I love It. " and stroked his cock while I cupped his balls with my other hand, He let out a little gasp. Using his cock like a handle I steered him back to the bed and had him lie on his back. I straddled him covering his midriff with my skirt I moved up rubbing my panty clad cock against his cock. I leaned down and kissed him full on the mouth licking his lips. I then moved down stopping to nibble on both of his little nipples then I dragged my tongue from the center of his chest down to his belly button. David separated his legs slightly and I moved down again until I was face to face with his cock. I looked up straight into his eye's as I grabbed his cock around the base and stroked it up to the head a look of pleasure appeared on his face as a drop of clear fluid appeared on the tip of his cock. I reached out with my tongue and tasted the drop and proceeded to lick his entire cockhead finally taking the whole cockhead into my mouth. I looked up to see those big blue eyes's just smiling at me. I wrapped my hand around the base of his cock again and stroked. I took as much of his cock into my mouth as I could and started sucking up and down while I stroked the part that I could not get into my mouth. David was breathing heavily. I reached up with the other hand to tickle his balls while swirling my tongue around his cockhead. I was now feeling little spasms as his cock grew even bigger and he started to buck his hips up off the bed. I could now taste his salty taste as he reached down and grabbed two hands full of my hair and drove his cock all the way down my throat. My first impulse was to gag but I swallowed instead. His pubic hairs were touching my nose as I realized I just deep throated and swallowed all 9 inches, He still had my hair and started fucking my face as he said "Take that cock sweetie take the whole thing." I grabbed his balls As he let go of my hair and screamed out" I am going to cum!" I felt his balls tighten as his cock grew even bigger I pulled up until only the tip was in my mouth and stroked the jerking shaft as I sucked on the head and swirled my tongue around the tip. I thought I was ridding a bull the way he bucked up and down. Spurt after spurt of molten lava pour forth. I sucked it all down. I loved it. I kept caressing those balls and stroking that shaft and sucking that cockhead until I had every ounce he could give. Finally he stopped moving and jerking and spurting. I looked up at his glazed eyes with his Cockhead still in my mouth. He smiled that big smile of his as I pulled my mouth away and looked down as I milked his cock from the base to the tip. He shuttered a bit as one last drop of white cum appeared on his cockhead. I licked it off with the tip of my tongue. I looked him back in the eyes. He said "That was the best orgasm of my life, Are you sure you never sucked cock before. " I said, " Never before but I will again, That was the most erotic thing I have ever done." David stood up after a minute and pulled me to my feet removing my dress he reached down and stroked my cock through the panties then pinched my nipples as he said, " You are on fire." He unclasped my bra and pulled down my panties, grabbing my cock as I had his he guided me back on to the bed. He looked me over and said " I cannot believe you have never done this before, I would say that you have to take hormones or something, You have the body of a girl. Hasn't anyone ever said anything? Look at those tit's and those leg's, and that pretty hair, You are beautiful." I said " I have been teased about it since I was little and normally dress and behave quite masculine, As to the hair I just like long hair. I did not think that the absence of body hair and the addition of a dress would make that much difference. But I have to tell you that I have always had a fantasy about dressing up like a girl and I have always wanted to try sucking on a cock." Dave reached out and caressed my tit's and pinched my nipples then tickled his way down to my cock saying" I have always fantasized about having sex with a pretty crossdresser. But I primarily like girls and you are the perfect embodiment of the perfect girl I have been searching for all my life." He stopped for a minute to lean down and lick the head of my cock, And then continued "I thought you were a girl and you were just playing with me until I actually touched your cock in the restaurant, You played the part so perfectly." He leaned down again, this time licking and biting my nipples while stroking my cock. Finally moving down until he engulfed my cock in his mouth sucking while he bobbed his head up and down. I could feel my balls churning. I was ready to explode, I bucked up my hips driving my cock all the way down his throat. I could tell he was starting to gag but recovered and started wrapping his tongue around my cock. I thought this is it when. He stopped and pulled totally away from my cock leaving me there twitching on the verge of the best orgasm of my life, How cruel. He looked in my frenzied eyes. Reaching down he grabbed his own once again erect cock and smiled an evil smile while stroking his own cock. He moved up beside me rolling me on my side. After a moment pushed his cock between my legs he reached around and started stroking my cock lightly with a mysteriously lubricated hand, Only to late did I realize what he was up to. He had managed to lubricate his cock and grabbed hold of my cock pulling me back to him he drove his slippery cock into my unsuspecting butt hole. The pain was incredible for his first few strokes. After that the ecstasy of the agony almost caused me to cream again. They say there is a fine line between pleasure and pain and I was riding it as he fucked my asshole the pain suddenly subsided. He kept stroking my cock as he fucked my asshole it was almost as if his cock was sticking all the way through me and he was stroking his own cock. Without missing a stroke he pulled me up into a kneeling position. Reaching around with his free hand he started pinching my nipples then ramming his cock into me as far as it would go gripping my throbbing member he leaned down on my back and started nibbling my neck. Sticking his tongue in my ear he said " I Just love fucking beautiful virgin little girls, This is exactly what I pictured when I saw you on the front of the boat." I felt like a little virgin girl getting fucked for the first time. I was for all purposes a virgin girl being fucked for the first time. He started fucking me in earnest. I felt long powerful lust driven strokes as his cock slide in and out of my ass. He kept time stroking my cock to every thrust of his cock. The excitement I felt building was like none before. I reached the brink just as I felt David's cock grow another inch. He started jerking uncontrollably inside of me he squeezed me close and continued to stroke me while I thrashed uncontrollably in a fit of ecstasy. I could feel his cock jerking and a warm wonderful feeling as he pumped his white-hot load into my quivering asshole. I pumped what seemed to be a gallon of passion into his still stroking hand. After what seemed like an eternity we collapsed in to a satisfied sticky heap. He finally pulled his still semi erect but totally drained cock from me and went to the bathroom. He returned much cleaner with a warm wet towel and proceeded to clean me off as I lay there and watched him with lazy eyes. He finally lay beside me and started to stroke my breasts. He said, "That was the most incredible sexual experience of my life, Wow." I reached down to fondle his balls and replied "I have never felt so thoroughly fucked and satisfied in my life." He turned and looked me in the eyes and said once again "Will you marry me? Do you know I have never had a virgin before tonight?" I replied " I ain't no virgin." Dave replied " Maybe Sam ain't no virgin but I am pretty sure Samantha was." I smiled and said "Samantha, I like that." I moved up and kissed him and said " I need to get back to my girl friend before she misses me." I got up and slowly did a reverse striptease for David. By the time I was done he was standing at attention again. I started brushing out my hair. David asked " What are you going to tell your girl about your new under things?" I responded " I don't think this is the appropriate time to tell Jennifer about this, It was a wonderful experience. I will think of something." Dave got up as I put on my new shoes. He gave me the picture from the boat and then he gave me his card, I looked at the address and was surprised to find he lived in Sarasota only 45 minutes from where I lived in Tampa. He said " Call me if you are in the area, I will be in Key West for three more days." He then grabbed hold of me and kissed me long and hard. I left with mixed emotions. I arrived back at the room at about 11pm. Jennifer had the key so I knocked momentarily forgetting how I was dressed, She came over and asked "Who is it?" I replied "SAM". She opened the door and just stood there staring at me for a moment without saying a word finally I moved past her into the room turning on a light. She was wearing a very sexy black silken nighty and was looking at me strangely When she spoke up and asked " Not that I mind but why are you wearing my dress?" I related the day's story to her leaving out a few of the more intimate details. As I got further along in the story I could see that my recital was turning her on in a major way, She moved over and started pinching my nipples through the dress and feeling my butt, I was starting to get turned on again. When I finished she stood back and looked me up and down and said "I can see why they thought you were a girl, You look fabulous." she pulled me to the bed taking charge in a way that was very unlike her but very arousing. She sat on the edge of the bed. I moved in front of her dropping to my knees. I pulled up the skirt to her nighty spreading her legs. I started licking her pussy. She orgasmed almost instantly grabbing my hair she pushed my face tightly to her pussy and started saying "Lick that cunt you little whore." By the time I was done she must have orgasmed 20 times. I could see that tonight was the night for me to satisfy everyone's homosexual fantasies including my own. As I got up and kissed her, she licked her own juices from my face and said, "You make a great lesbian." Pulling off her nighty, She just about threw me on the bed. Pulling up my dress she looked at me strangely and said," Just where did you get the bra and panties?" Smiling shyly I replied," David bought them for me." She looked at me appraisingly and said," You little slut." She then mounted me in a very masculine manner and started fucking me as if it were her cock instead of mine, I once again felt myself building to another earth shattering orgasm. Jennifer was looked as though she was having one continuous cum, I finally came with an earth shattering bang bucking up into Jennifer so hard I almost threw her off the bed, It seemed to last for hours. I was jumping around and Jennifer hung on and rode me like a wild stallion, or should I say a wild filly. Finally she rolled off of me and helped me take off her dress. She looked at me with an amused look while she removed my panties and bra. She held me close and started caressing my tits and nipples. She said " I could get used to this." I told her " You know, They called me Samantha tonight." She said "Samantha I like that "You became Accidentally Samantha." We both drifted off into a deep-satisfied sleep. We woke up late that morning, I turned toward Jennifer and kissed her. She pulled close and asked me "Did you like being a girl for the night?" I responded "Yes it was a lot of fun". She then asked me " What did you like about it, You are always so masculine?" I responded " A lot of People paid attention to me and bought me drinks and presents and flirted with me. That was quite fun and I got to see life from the eye's of a pretty girl that was very interesting I now see how pretty girls get the way they are. I felt sexy and everyone treated me sexy that was arousing. And clothes were soft and felt good the way the lace around the skirt tickled my legs how could I have not liked it." Jennifer said, "If you think that dress was soft a silky wait until you try some of the other things." She then asked me "Would you dress like a girl again?" I said "yes". I then got up to go into the bathroom. When I walked back out of the bathroom Jennifer intercepted me. She pulled a white silken nighty over my head I put my arms through the arm holes as the cool silken material caressed my body as it drifted down causing instant tity nipple hardons. It came to rest around my upper thighs. Jennifer then pulled my long blond hair out from under the back of the nighty. Feeling my soft hair against the silken material was wonderful, How come these delights were only reserved for woman? She then led me toward the bed. As she laid me on the bed she rubbed against me and said, "Now this is soft." She then reached down and grabbed my half erect cock through the silken material and asked me "Could I dress you up as a girl tonight and take you out on the town, My lesbian part wants to know ?" I asked "What do you plan on dressing me in ?" Jennifer responded "Nothing other than your favorite outfit !" I said to myself, "My favorite outfit!" I had bought this for her two months ago, A little black velvet dress with sheer stockings a black garter and the softest and sexiest black bra and panties I had ever seen or touched with a matching silken slip. When I saw Jennifer in this outfit I got and instant erection. Now the thought of wearing this outfit caused an almost instant hardon as well as goose bumps all over my body. Jennifer then started stroking my cock with the silken material as she cupped my balls with the other hand and said "The thought of dressing you up as a girl just turns me on completely." As she pressed herself to me I could feel the silken material as she squirmed. Fighting to control my voice I said "maybe". As she pulled up the silken nighty and impaled herself on my raging hadon. I said "YES". Again we had the best sex we had ever had. About two in the afternoon Jennifer decided we must start to get ready. First she applied some more of the hair removal creme although this time more accurately and sparingly. Next I did the closest shave I had ever done, After that we took a shower together and Jennifer spent a lot of extra time washing and conditioning my hair after which she placed rollers in my still wet hair. I could tell she was having the time of her life as she told me, "I have wanted to do this since the first time we meet but I did not think I would go for because you act so masculine most of the time." I said, "before yesterday I would not have wanted to but this was to much fun." She then put the bra on me and was surprised when it fit almost perfect. She adjusted the straps and pulled my boobs up and adjusted them. Fondling me through the silky material unable to control herself She pulled down the cups and nibbled on my nipples making them bigger and more erect than I thought possible if not a little painful, sensitive and swollen From her bites. Next the Garter belt and sheer stockings were heaven caressing my legs all over and adding an ever so feminine appearance. I could not stop running my hands over them. Jennifer who had been dressing herself at the same time spent the next few minutes fondling and rubbing our silken covered tits together. The next were the panties, They were so soft I almost creamed them as soon as they wrapped themselves around my cock and balls. Jennifer wanted to tape me but I declined saying that the flared skirt would hide any incriminating bulges. I pulled on the silken slip and went to look in the mirror but Jennifer would not let me until we finished. Next she pulled out the makeup case and went to work telling me that I had so little facial hair and such a pretty face not much was required. A little lipstick some eyeliner and blush. She then told me to put on the dress while she did her own makeup and then she would finish my hair. This was what I was waiting for this was the cutest sexiest dress I had ever seen. I unzipped the back and stepped into it pulling the straps up around my shoulders. Stepping over to have Jennifer zip it up I straightened the hem line and turned around, Jennifer's mouth just fell open as she said, "My god you are just the prettiest girl, I am in lust." She pulled me over to the chair and undid the rollers. Using a curling Iron, hair spray and a few different types of brush's she went to work after 20 minutes of work she stepped back shook her head and said, "Sit there one second." She went to the suitcase returning with a pair of black shoes with wide 4" heels saying, "I hope these fit." She placed them on my feet and did the little straps. I stood up, Jennifer said, "twirl." I did almost falling. Jennifer said, "You look awesome, That was the most fun I have ever had. Come look." We walked into the bathroom in front of the full-length mirror I was stunned, Looking back at me was the prettiest girl I had ever seen. I could not move. I just stared. Jennifer said " Breath" I had been holding my breath. Jennifer stood back and watched me first I touched my breasts and then ran my fingers down my sides to my legs. That beautiful tangle of golden curls that framed my face. I then pulled up the skirt to make sure it was me. The dress and pretty silken slip just slid up my legs over the silken stockings and the pretty black garter belt and those sexy panties about to burst from my raging hardon. I slowly stroked myself through the silken panties a few times while gazing in the mirror. I heard Jennifer moan and looked in her direction She had slid her hand into her panties and was rubbing herself as she said, "That was incredibly sexy, I could not control myself. I wish you could have seen yourself." She walked over in front of me sliding to her knees she pulled down my panties and started sucking my cock. I watched in the mirror. I saw what looked like a very pretty girl in a sexy black dress getting her pussy licked by a very pretty brunette girl in a garter belt on her knees. I creamed immediately. Jennifer stood up licking her lips and kissed me, I could taste myself on her lips. We both looked in the mirror. Jennifer said " I don't want you to take this wrong but you make a better looking girl than you do a guy. Where I had thought you might have had a little extra weight in the chest and hips was just a few misplaced chromosomes. You always dressed and acted so masculine that I never noticed you have an awesome figure you have a skinny waist but it is a females waist. I bet you have the same measurements as I do, We have always been able to wear each other's clothes. Jennifer started to get dressed again. I watched more closely than ever before. Normally I was impatiently pacing by now. This time I watched closely as she curled her hair in much the same manner that she had curled mine. Some black eyeliner a little blush, Lipstick and a Navy blue dress that hugged her hips where mine flared. She put some silver clip-on earrings and a pearl necklace on me. She got out a black purse that she gave me along with lipstick and powder. A blue purse for her and some blue pumps she looked awesome we both went to look in the full length mirror the two girls I saw looking back would be any mans wet dream. Jennifer said " Now there are two hot babes !!!"