Damsel In Dis-Dress free porn video

Damsel In Dis-Dress I was finally packed and ready to head home. I finished my last exam a few days ago so my summer was starting now. My name is Sam and I am a 19 year old college student. I just finished my second year at college. I was heading home, it was about a five hour drive, but luckily my friend Kimberly was coming with me. She lived a few hours away from me, but I was going to drive her to my place where she would stay for a few days then her parents would pick her up and she would make the trip home. Kim was not my girlfriend we were just friends, Infact I would say she's my best friend. She knows me so well almost too well, she knows all about my crossdressing. I've been dressing as a girl ever since I was a little "boy" still not sure why but I just love it. I am a bit on the feminine side but looking at me you wouldn't think I'm a crossdresser or a flaming homosexual or anything, but truth be told I'm leaning that way. I told Kim about my dressing in our first year of college. She's totally cool with it and she has really helped me further my dressing. We actually moved in together in our second year and I've been dressing up like a woman a couple times a week. Kim and I are similar in size, she's actually a bit taller than me but it's great we get to share clothes just like sisters. No one else at school knows about Sabrina, the name I go about when dressed. I've been fairly careful about that but in the past year I've been getting much more comfortable being Sabrina in public. That's enough background information for now...on with our story. We made the trip in about seven hours, I know I said I lived five hours away but Kim and I stopped at the outlet mall a couple hours away. We made it to my parents' house at about 6pm. My parents were away, they would be away for most of the summer so I would have the summer to myself. As we drove through my neighborhood Kim was impressed with all the homes, we were pretty well off, heck we were rich or at least my parents were. I started to pull into our driveway when we noticed my neighbour Mike out cutting his grass. Mike was cutting the grass and was shirtless something Kim noticed right away. "Hey now who is that?" I laughed. "That's my neighbour Mike, he likes to do his own yard work and of course he likes to do it without a shirt." Kim quickly replied, "Woah, Woah, wait, is THAT your neighbour you, well you know." I cut Kim off quickly. You see one drunken night at college when we were talking, she told me about a time where she made out with another girl, so the conversation turned to me and I told her about what kind of men I would like and I guess I went on about my neighbour Mike. I have only fooled around with one guy before and he was a gay guy at college and we'll I didn't really like it, it just didn't feel right. I think the problem was that I was not dressed as Sabrina and the other guy was gay and I think I'm only attracted to masculine straight men. Mike, my neighbour was indeed a masculine man. He was older, close to 50, he was a big guy as well and he was quite well build. That night back in college I told Kim that if I was going to be with a guy again it would be with a man like Mike. I don't know him too well. His daughter who was about ten years older than me use to babysit me. Mike and his wife were friends with my parents. I was always a bit intimated by him, when I was younger I was a bit of a trouble maker and I don't think he liked me much. I actually broke into his car a few times when I was younger and we egged his house on Halloween one time, and one time when I was drunk, a friend and I stole one of his Santa Claus's from his lawn at Christmas. He never knew it was me but I was still a bit scared of him. Anyways we got out of the car when I realized that I didn't have my house key. I knew that Mike's wife had our extra key so I walked over to ask him. Kim stayed at my car. As I approached him he saw me coming so he shut off the lawnmower. "Hi Sam, how are things?" "Hi Mr. Walker, things are good, thanks. Listen I can't seem to find my key, would you know if Mrs. Walker would babe our spare key?" Mike wiped the sweat from his forehead, he was quite hot, his chest was glistening with sweat. "Um yak, not sure, Shelly (Mrs.Walker) was out of town for a couple of weeks, but let me check." Mike went into his house to look for the key. I waited outside and I turned to see Kim was making kissy faces at me, teasing me about Mike. I gave her the finger, but then I turned around and Mike was there. He handed me the key. "There you go, hey who's the girl?" I grabbed the key from Mike. "That's my friend Kimberly, she'll be staying with me for a few days." Mike smiles at me. "Ah I see, well you and your girlfriend have a good time." I told him that Kim was just a friend. He smiled again. "Ah okay that's cool with me." I thanked him and I started to walk away when he called back at me. "Listen Sam, I know your parents are away so if you ever need anything just let me know, and um Sam, no parties over there." I told him not to worry about that, it will be quiet. When I was about 15 I hand a house party and we'll like most house parties it got out of control. There was actually some damage to Mike's yard and two people were caught having sex in his pool, needless to say, he was not happy. I made my way back to Kim and we started to unpack my car. Kim had a big smile on her face. "You were certainly chatty with your neighbour, were you making dinner plans for later?" Smiling back at her. "Nope he just gave me the key, you can shut up now you slut!" She replied, "You're the slut." This went on for a while. The next day we were just laying out by the pool when Kim suggested that we do a little shopping. I was getting bored so I was up for some shopping. Kim then suggested that Sabrina should go shopping. I was intrigued, I do like to shop, and Sabrina really likes to shop. Kim and Sabrina have been shopping a few times before, but this would be different, someone might see me dressed up and leaving the house. I did go out dressed a few times when I was younger and had the house to myself, and one time I did go shopping, I was so scared but I did it. I still wasn't sure, but eventually Kim talked me into it. So we jumped out of the pool area and started to get dolled up. I needed to shave my legs so I hit the shower first, when I got out and I was nice and smooth Kim was butt naked shaving her bush. Remember I said that we were just like sisters so seeing each other naked wasn't a big deal. We both decided to wear dresses, I was going with a cute peach colour summer dress that I would wear a short feminine Jean jacket over top of. I've been growing my hair out for over a year so it wasn't really long but with Kim's help I was able to style it into a cute dirty blonde bob. My makeup was subtle, but I always go heavy on the lip gloss. I added some hoop earrings. I painted my nails a pale peach colour. I couldn't decide on shoes, I wanted to wear heels but I could also go with a cute pair of flip flops. I then convinced Kim to wear heels if I did, she agreed. So I grabbed a cute pair of white 3.5 inch pumps. I added some of Kim's perfume then grabbed a purse and I was ready. As always during girl time we take plenty of pictures. I decided to take my mom's convertible, it was much nicer not to mention cuter than my car. I always fun it somewhat difficult to get used to driving in heels. We left the house without a problem, the sun was just starting to go down. Shopping is always fun, but it is especially fun shopping for Sabrina. Shopping with a girlfriend is so much fun as well. I'm at a point where I'm pretty comfortable out in public as Sabrina, my voice still needs a little work but confidence is the key. Kim and I went to a bunch of stores, I decided to get a new bikini so that was a lot of fun. It was a bit difficult finding one that would make my figure look good. We stopped at the food court and grabbed a latte. There were plenty of boys and me. Checking us out. Truth be told, most of them were checking out Kim, but some liked what they saw in me :) As we sipped our lattes I noticed a few people that I recognized. There was a former teacher, and my old tennis coach was here with his wife. I really should go say hi :). After a while we were getting tired, shopping in heels takes a lot out of you. We made our way home and as I pulled into our driveway we noticed Mr. Walker walking his dog. I tried to park in the garage but the opener would not work. I really didn't want to get out of the car now with Mr. Walker nearby. Kim could tell I was upset, so told me to relax and we could just park in the driveway and walk in, no big deal. I calmed down and parked and got out of the car. I looked back but didn't see Mr. Walker. I grabbed our bags from the trunk and when I closed it I noticed Mr. Walker's dog was running towards us. Kim started to pet the dog but before I knew it there was Mr. Walker. "So sorry girls, Cooper is friendly he just wanted to say hi." I kinda froze but Kim replied, "Oh no worries, Cooper is very cute." Mr. Walker introduced himself. "By the way I'm Mike I live next store." "Hi Mike, I'm Kim and this is my friend Sabrina." I just gave Mike a little smile. "Okay you ladies have a good night, say hi to Sam for me." Then he grabbed Cooper and walked down the driveway. I grabbed Kim and we rushed inside. I closed the door and we both started to laugh. "Oh my god, really! I need some wine." As we tried on the clothes we just bought and drank our wine, Kim joked about how I was going to fantasizes about "Mr. Walker" tonight...she wasn't wrong. Over the next few days with Kim I decided to stay in girl mode. We had no real plans so why not. I've been wanting to be Sabrina some more so here is my chance. We spent time at the pool, in fact I got a bit of a bikini tan which is pretty funny. We went to the movies one night and we went for a Rollerblade one day. A few neighbours saw us, including Mike, we just smiled and waved as we passed by. I was getting really comfortable being a woman. Alas Kim's time was up and her parents were coming up to get her. I went back to Sam mode and saw her off. I was going to miss her, like I said we were like sisters. But I would see her when school starts up. The next day or two I just kinda moped around the house, I was already bored. I decided to check out my mother's closet. When I was younger I would wear her clothes every chance I had. She loved her clothes, she is still very good looking and took pride in her appearance. I was a very lucky "boy" to have all these gorgeous feminine things around. I decided just like old times to have a little fun in my mother's closet. That night trying on dress after dress, I realized just how much fun it was. I was taking a lot of photos and I looked pretty good. I decided to spend a few days again as Sabrina. The next week I lived as a woman. I went grocery shopping, mostly junk food. I ran errands as Sabrina and I spent plenty of time by the pool. I really like my new bikini, plus my mother had a few nice one piece bathing suits. It was now Saturday and I decided to go to one of the TG clubs in town. I've never been to one but I wanted to give it a try. I had a few online friends that were going to go as well. That afternoon I decided to work on my tan a bit so that I would look good that night. I laid down by the pool, put my ear buds in and soaked in some rays. After an hour I decided I had enough sun. I got up and took my ear buds out and I could hear nailing going on. I looked up and it was Mr. Walker working on his roof. As I looked up I noticed he looked down towards me. He was looking right at me. There was no hiding on my part. Here I was with a little pink bikini on. Since he was looking I decided to give him a bit of a show, I walked the length of the pool making sure to wiggle my ass for him, then I dropped my towel and slowly bend over to pick it up. When I turned around and looked up Mr.Walker was looking right at me. The power women have over men is incredible. He actually gave me a little wave and I gave him a little wave back. So once again Mike has seen me in girl mode. I wasn't too worried, he still didn't know it was me, at least not for sure. As I hit the shower I thought I should have went over to his house with my bikini on and brought him a cold beer, I'm pretty sure that's how some pornos start. Anyways I played with myself as I showered. My plan was to get dolled up and head to the club for 10pm. I've never been to a club before so I decided to dress up a bit. I went with a little black dress with a bit of ruffles around the neckline. I was going with a pair of nude four inch pumps, actually they were my mother's. With my corset and my breast forms I had a pretty cute little figure going. I've gotten pretty good at tucking so there wasn't even a tiny hint of a bulge. I did my hair, not as well as Kim could do it but it was pretty good. I put on some false nails, I went with a French manicured look. I worked on my cleavage a bit, the girls looked great! I took some time on my makeup. I went with simple earth tones, a shimmering metallic eye shadow, some simple blush, foundation, I did a little bit of shading but luckily I have my mother's nose :) lastly I went with a burnt almond shade of lipstick adding some lip gloss of course, what gurl doesn't love having shiny lips? Since I was wearing my mom's heels I figured I'd check out some of her jewelry. I picked out a cute white gold necklace with a diamond heart pendant. I also grabbed a matching bracelet. I used my own hoop earrings. Next was some perfume, I don't like using a lot but I do like to smell pretty. My mother has some pretty expensive perfumes, but then I thought what boy who is dressing up like a girl want to smell like their mother, good point so I grabbed my J-Lo perfume and sprayed on a bit. I packed my purse I put in some makeup, my women's wallet, some gum, and some condoms. I also put my phone in a very cute and very pink case. Now I wasn't planning on using the condoms, but hey a gurl has to be prepared. I put the purse around my elbow and took a good look in the mirror. I was pretty happy with my look. I did wish my hair was a bit longer but it was close to shoulder length and I didn't really want to wear a wig. Looking back at the mirror it amazes me how happy I look when I'm all dolled up as Sabrina. I never smile this much. So, I was ready to go. I decided to drive, and to take my mother's car again. This way I know I can't drink too much and get into trouble. So, I was off, the car was in the garage. Since I've been spending so much time as Sabrina I wasn't really worried about the neighbours seeing me, besides it was dark now. It took me about 20 minutes to reach the club. I parked in a well-lit parking garage. I had to do a short five-minute walk to the club. I made sure I put my keys in my purse. I was pretty good at walking in my mother's heels, heck I've been doing it since I was like ten years old. I've practiced enough that my walk doesn't stand out. The street was fairly busy but no one really bothered me. I got a few looks from the guys and some of the women gave me some not so nice looks, must have been because of the heels. There was no line at the club, so I just went in. I was doing pretty well, my confidence as Sabrina was at an all-time high, but my confidence would be tested right now. There was a very big bouncer inside the club and he asked me for ID. I wasn't worried about showing him my male ID after all this was a TG club, but I was still only 19, and the club was 21 and over. I sheepishly handed him my driver's license. He looked it over and smiled at me. "What's your name sweetheart?" I replied. "Um well my ID says Sam, so ya, my name is Sam." He laughed. "Sweetie I know what your ID says, I can read, but do you go my Samantha, or something?" Finally clueing into what he was getting at. "Oh sorry, Sabrina, my name is Sabrina." "Sabrina, hey I like that, I've never dated a Sabrina. Listen Sabrina, your ID says you are only 19 and you need to be 21 to get into the club," he said with a grin. Okay so I was hoping to avoid this, but I knew it was a possibility. I planned on giving him a $20 as a bribe. I guess I'm not very smooth, so I reached into my purse and pulled at the money. "Would this help me get in, this is my first time hear and I'm meeting friends." He smiled again and took the money. "Well that's a start, but maybe we can work something out. You are a fine looking white girl, you know. I'm on break in a couple of minutes, maybe you and I could..." Just then, I heard someone else's voice. "Now Carl you leave that poor little girl alone, you know better than that! Beside's she's with me!" Turning around I saw one of my friends, Sherry. Carl laughed and said it was nice to see Sherry again. He said he was sorry and that we ladies could go in. I smiled at Sherry as we walked past Carl. Sherry went to grab the $20 but I just said he could keep it. Carl winked at me and we entered the club. The club was pretty busy, I sat with Sherry and some other Tgurls. The people watching was fun. I guess I wasn't trying to be too judgement but like I said before I can be a bit of a dick, or in this case a bitch. There were plenty of "men in dresses" meaning they were not passible at all and kinda gross. There were also plenty of transsexual escorts, which I found kinda gross. Of course there were plenty of men in the club but most were old, out of shape, again kinda gross. I bought Sherry a drink for helping me out and I went with a rum and diet coke, my go to drink. Sherry was very nice she was older I would guess in her 40's but she was well put together, another online friend, Emma was there and she was very nice as well. We chatted for a bit then we decided to hit the dance floor. It was so much fun to dance as a woman. The dance floor was busy, and eventually there were men hitting on us. I had a young Latino man grind up against me a few times. He wasn't my type so I kinda just moved away, but he would move with me. Eventually Emma saw this and grabbed my hand and said, "Let's go to the ladies room." Inside the ladies room is always fun for me. Normally I'm in there with Kimberly, but I always love an excuse to touch up my makeup. This "ladies" room was a bit different. There were a couple of real ladies in there, along with Emma and myself. We started to fix our makeup, and we joked about the guy in the dance floor. The other women left and it was just the two of us, so we thought. We heard some noise coming from one of the stalls, then we heard and loud moan. Soon enough we saw a rather heavy man exit the stalk along with one of the tgurl escorts. He walked past us and said. "Hi ladies, looking lovely this evening." We waited a bit then both started to giggle. The escort then left the stall, smiled at us and fixed her makeup. After all blowing some fat hairy guy in a bathroom stall sure can mess up a girl's makeup! She left and we laughed again. Emma joke that I'll be in the stalk with some dude by the end of the night. I told her to fuck off. We went back out and sat down and had another drink. This would be my last. Emma told me that when she is feeling particularly girlie and horny that she likes to stand alone at the bar and wait until a guy comes hit on her. I told her that I'd love to see that. She agreed but said that I would have to go next. Watching her she was at the bar for a few minutes then before a guy started talking to her, she just smiled back at me then she waved her finger at me gesturing for me to get my ass to the bar. I grabbed my purse and stood at the bar. The first guy that came up to me was a short Asian man. He offered to buy me a drink but I told him no thanks. He left then the same heavy guy from the ladies room came up to me. He was plenty drunk. He put his hand on my ass and slurred something, I kinda just walk away at that point. Emma was smiling at me, and she was doing quite well, she was sipping her drink and her new friend's hand was comfortably resting on Emma's ass. Then the bartender brought over a drink for me. "This is from the gentleman at the end of the bar." I said thanks and looked over to the end of the bar. There was a nice enough guy looking back at me, he waved and I waved back. He then started to walk towards me. Not being used to being hit on my men I guess this is a thing that happens. He was nice enough, tall, slim, maybe in his 30's. We chatted for a bit. He seemed really nervous, I guess so was I but he was uncomfortably nervous. I see why women like a confident man, and ya I too liked a confident man, but hey I was having fun so I just went with it. I was trying to decide if I would ever have sex with this guy, I wasn't quite sure. As we chatted he started to talk about sex and that he liked to be tied up and spanked. He then told me he like the tranny (a big no no) to take control and fuck him in the ass. It was at this point I quickly finished my drink and told him I was leaving. There's one thing I can't stand is when a guy hits on a tgurl like me and wants me to plan the man roll. I mean what the hell, I'm the woman here, I'm the one wearing a dress, makeup, high heels, I'm the one who will take the woman's roll. I headed back to the dance floor and danced with the other gurls for a while. Then it was starting to get late and Sherry already left and I saw Emma leaving with her new friend Steven. I actually decided to walk out with them. Steven seemed pretty nice, he definitely wasn't my type but I'm sure he and Emma would have fun tonight. They actually walked me back to my car. I have Emma a big smile before getting into my car. The drive home was pretty uneventful, I had three drinks but I wasn't drunk so I decided to drive slow just in case. I was about five minutes from home when I heard a loud pop and new right away that something was wrong. I pulled over to the side of the road and got out to discover I had a flat tire. Shit, this was the last thing I needed. I've never changed a tire before but I knew to look in the trunk for the spare. I saw the tire but I didn't know how to do this. There were a few cars driving by but I didn't really want to ask for help, not with the way I was dressed. Just then a car pulled up behind me. A guy got out and asked me if I needed help. I was nervous at this point and unsure if wanted his help. He asked me if I had a flat and I told him yes it must have just happened. He said he would help me out. He told me his name was Jason, I told him I was Sabrina. Now at this point I think I was doing pretty well with my voice. He asked me if I ever changed a tire before when I said no he suggested that I walk back to the trunk so that he could show me the tire and Jack. When I went to the trunk he showed me the jack in the trunk and asked me to get it for him. I reached in to grab it when I felt his hand on my ass. I quickly stood up and he then placed both his hands around my hips. "Ah you like that baby, you need some help, well maybe you can help me." I kinda froze not knowing what to do. I started to pull away but he grabbed me tighter. "Don't fight it baby, you are all dressed up tonight, let's have some fun." Then I push myself away from him. "Leave me alone you assholes," I shouted at him, but his face got really serious, the jig was up, when I raised my voice there was no hiding that I was not a woman. He then grabbed me by the wrist. "What the fuck, you're a dude. That's fucking sick you little faggot. Your dressed up like a woman, you little sissy you can't even change a tire." He then pinned me to the car and asked for my keys. They were in my hand and when he went to grab them I through them into the bushes. Just then a motorcycle passed us by I tried to wave him down but Jason grabbed my wrist and pulled me towards him. "Listen you little sissy, that was a dumb move. I was just going to steal your car but now I'm going to have to beat the shit out of you." I tried to push him away. "Fuck off asshole, just take the car and leave." He then put his hand around my neck. "It's kinda hard to steal a car without the keys bitch?" I tried fighting him then he pulled out a knife and turned me around pinning me to the trunk. "You like being a little cunt so much why don't I give you that little cunt you've been dreaming of." He then put the knife under my dress up against the front of my panties. At this point I started to scream. Just then the another motorcycle came by in the other direction. He got off his bike and approached us. "Is everything okay here, do you guys need any help?" It was dark so I couldn't really see who it was, but Jason just told him that we were fine to just leave us alone. Then the man looked me straight into my eyes and I could see it was Mr. Walker. He took off his helmet. "Ma'am are you sure you are okay?" With that I yelled for help and Jason pushed me to the ground and lunged at Mike. The two of them started to fight. I wanted to help but I felt so useless. I ran to the front of the car to grab my phone from my purse. I tried to dial 911 but I dropped my phone. By the time I found my phone Jason was back in his car and he started to drive off. Mr. Walker was running after the car. I yelled at him that I was calling the police. He started to walk back and told me to hold off. I walked towards him. "Oh my god are you okay thank you so much you totally saved my life." He was holding his arm I could tell he was cut. "Nah I'm fine, it's just a flesh wound, what a psycho that guy was." I apologized to him and asked if I should call for help. He told me I was fine and asked me if I was okay. I told him I was scared and shaken but I was okay. He then said he would fix my tire so that I could get home with my mom's car. So now there was no denying that Mr.Walker knew who I was. I told him that I through the keys away. We both looked for the keys but it was no use the bush was too dense. I told him my house key was on the key chain as well. While looking through the bush I tripped and fell, when I tried to get back up I noticed I had broken one of my high heels. Mike grabbed my hand and helped me to my feet. "Are you okay did you twist your ankle?" Trying to balance myself. "Hum I'm ok, I think I just broke my heel on my shoes, actually my mother's shoes, she's going to kill me." Mike decided to call of the search for tonight. "Listen it's too dark and the bush is too thick, let's call off the search tonight, come on I'll give you a ride." Mike noticed I was having a hard time walking with the one broken heel. I was simply going to take both heels off but before I could he reached for my hand. "Here let me help." He then carefully picked me up and carried me. I was a bit shocked by this but with what was going on tonight I just let it happen. He was carrying just like a newlywed Husband would carry his new wife into their home on their wedding night. He put me down beside his bike, he handed me his motorcycle helmet. "Here out this on, let's get you home." I grabbed the helmet but I couldn't do up the straps so he had to help me. He got on his bike and told me to hop on. I grabbed his hand and he helped me up. We were about to leave when I told him I forgot my purse. So, I hopped off grabbed my purse and got back in the bike. This was especially embarrassing for me. Not only did Mr. Walker discover that I was a crossdresser but I also had to run back to my mom's car to retrieve my purse. We started to ride off but I asked him if I should hold onto something, he replied. "Ya you probably should." Then we took off. I put my hands around his waist to hold on. We didn't speak a word on our way home. Once we got to my place I told him that I didn't have another house key. He suggested that I should probably stay with him tonight and that in the morning he would find my keys and take care of my mother's car. As I walked with him towards his house I noticed my high heels were broken, or at least one of them. My mother would be pissed. When we got inside I asked him if I should call the police. He said I could do what I want but things may get a bit embarrassing for me seeing as I was dressed up like a woman driving my mother's car. He also asked me if I was drinking. I told him I had a few drinks. I decided not to call the police. He asked me where I was tonight and I told him I was at a club. He didn't say anything. He then told me he was going to take a quick shower and to clean himself up. He told me that I could grab something to wear from his wife's closet or that there are still some clothes in his daughter's room. I wasn't sure what he was getting at. Why wouldn't he just give me a pair of his shorts and a t-shirt, I mean sure it would be too big for me but wouldn't that make more sense. I guess he clued in that I was confused. "You can wear whatever you want but I figured you like to dress like a woman and well hell you are dressed like a woman so you might want to grab something from their closet." Then he walked away. I was even more confused now but I waited till he was gone then I went up to his daughter's room. His daughter Lyndsay was a few years older than me, she used to babysit me. She was going to school over seas. Here room was still there, her bed, dressers, etc. She had a nice walk in closet. It wasn't fully as she had some clothes with her but there was still plenty of clothes. My dress wasn't ripped but it was dirty. I got out of the dress leaving my breast forms and corset on. Looking through her closet I wasn't sure what to wear or why I was going to wear her clothes. Finally I decided on a red and white polka dot summer dress. It tied at the waist. I put it on and it looked good I gave it a twirl. It wasn't short just a couple of inches above the knee. I went back downstairs to the living room but Mr.Walker wasn't down there. I waited a bit then I got a look at the mirror and my hair and makeup did not look good. So I grabbed my purse and went to freshen up in the washroom. As I was fixing my makeup I was thinking how fucked up this night has been, and why was I fixing my makeup now! Weird. I heard Mr.Walker walking around, I put everything back in my purse and went back to the living room. He looked at me and smiled. "Well that looks good, her dress fits you well." I shyly thanked him. He said he was grabbing a beer and asked me if I wanted a drink, I told him sure. He then noticed that I wasn't wearing any shoes, and suggested that his wife had shoes that should fit me, he commented on how small my feet were. I said okay then I went back upstairs to look at shoes in his wife's closet. There weren't plenty of shoes, not the same selection as my mother's but I did find two pairs of white heels that would go well with my dress, there was a two inch strappy sandal and a three inch pump, I went with the pump. As I was walking down the stairs I saw Mr.Walker standing there he was drinking his beer and he had a glass of red wine for me. He handed me the wine, I thanked him. He sat down and so did I. He asked me how the shoes fit, and I told him they fit pretty well. He shook his head and said he doesn't know how we are able to walk in heels like that. I laughed and said it just took practice. He then asked me just how long I've been practicing, just how long I've been dressing up. I told him since I was about ten years old. He then asked me what I was doing out tonight by myself. I told him about the club, and he shook his head telling me it was a dangerous game I was playing. I just went quiet. Mr.Walker then finished his beer, and then asked me if I could get him another one from the fridge in the kitchen. I thought that was a bit odd but I got up and headed to the kitchen. As I walked, I could feel Mr. Walker's eyes all over me. I grabbed a nice cold beer from the fridge and when I returned to the living room Mr. Walker was now standing. I brought him the beer, he took a swig and smiled. Then with the beer in the one hand, he grabbed me by the waist with his other hand and pulled me to him. He grabbed me tightly and kissed me. I was caught of guard I started to push away when he grabbed me even tighter and kissed me again. This time I didn't fight it I kissed him back. He broke off our embrace. "Wow you even kiss like a woman." I shyly thanked him. While still holding me he said, "So you are having a lot of fun pretending to be a woman, you are tricking a lot of people, you are taking a lot of risks." He moved his down from my lower back to my ass and he pulled me closer. "Your ass is nice and tight, do you feel that, do you feel what you are doing to me?" He was taking about his now hard cock poking me in the stomach from within his jeans. I didn't say a thing, I just nodded in agreement. He smiled. "Good, now that you want to act like a woman, why don't you get on your knees and take care of this for me just like a woman." He took a step back and I was just starting at him, I was kind of shocked. He was starring right in the eyes. "Well?" I looked down at the floor and I slowly began to kneel. Soon I was in front of Mr. Walker as he looked down on me. He put his finger under my chin and lifted my head. "Listen, I'm not like that asshole tonight, I'm not going to force you to do anything." He undid his belt and unbuttoning his jeans. "It's just me and you here right now, I'm a man and I have needs. You are playing the role of a woman so I'm treating you like one." He then unzipped his fly and pulled down his pants. His dick sprung out from his underwear and it was spectacular. He was big, way bigger than me. Here I was on my knees dressed as a woman in Mr. Walker's house, kneeling in front of him with his erect cock just inches away from my face. What the hell did I get myself into? Was Mr. Walker going to rape me? He started stroking his cock. He then looked at me with a very serious face. "We'll go ahead what are you waiting for." I licked my lips took a deep breath and reached up with my hand and wrapped my hand around his throbbing member. He smiled. "Now that's a good girl, keep going." I started to stroke his shaft. He moaned. "that feels good, listen sweetie what do you call yourself when you are all dressed up like this?" I whispered, "Sabrina." He told me to speak up. I said Sabrina a bit louder. "Sabrina, hey, ya I can see that, that's a good name for a woman like you. Now Sabrina keep going." I reached in and gave his cock a kiss. I started to kiss up and down his shaft. I kissed my way down to his balls then I ran my tongue from the base of his cock all the way up to his head. He started to rub my head. "That's it Sabrina." I opened my lips and slowly engulfed his cock into my mouth. I wrapped my lips tightly around is cock and I began to go up and down on his shaft. Mr.Walker was indeed enjoying this as he let out a few moans. "That's it Sabrina, keep sucking. You should not probably call me Mike instead of Mr. Walker." He kept talking as I sucked his cock. "You know when I saw you out by the pool this afternoon and you were shaking your ass for me in that tiny bikini, I know you were teasing me, I know how some of you bitches are. You know you should really be more careful when you flirt with men. See when you tease a real man this is what happens to you, you end up on your knees sucking cock. But obviously you enjoy it. Don't you?" I looked up to him and I just kept sucking. "Don't you Sabrina?" he asked again. I obviously couldn't say anything with Mike big fat cock in my mouth so I just nodded yes as I looked up at him. Mike just smiled down upon me. "Something tells me that you've sucked cock before, that pretty little mouth of yours has tasted dick before?" Once again I nodded yes. Like I said earlier I did suck a cock before, in fact two cocks, one was with a guy from high school and the other was with the gay guy in college. Both were more like boys than like men. Mike was indeed all man and so was his cock. With my lips wrapped tightly around his shaft I could feel every vein in my mouth. This was a very big piece of meat in my mouth, if I had to guess I would say that Mike's cock was about nine inches, but it was also very thick. Slowly but surely I was starting to relax and started to actually enjoy sucking Mike's cock. Sure the circumstance I found myself in wasn't my ideal Fantasy when I had thoughts of Mr.Walker, I always pictured something more romantic. He was being forceful but he wasn't forcing me, he has told me a few times that we can stop. I was about ten minutes into this blowjob when Mike stopped his moaning. "Okay baby you are doing a fantastic job, you got me so fucking hot, but soon I'm going to explode in that pretty little mouth of yours. Once I do that you will truly be my woman, my seed with be inside of you. I don't want you to stop but if you do want to stop and chicken out like a little bitch, well you should do it now." I was looking up at him the entire time, I didn't nod, I didn't say a word, I just closed my eyes and started sucking even harder. Mike obviously enjoyed this as his moaning and breathing tempo increased. Soon I felt his cock tense up between my lips, then I tasted a little fluid in my mouth, then even though I knew was has coming next, he shot a big load into the back of my throat. This was it, he was cumming in my mouth. I kept sucking and Mike kept cumming. I knew all men want their women to swallow their load, so I started to swallow as much as I could. At one point while swallowing and while accommodating his fat cock in my mouth I started to gag. I was fighting my gag reflex, I didn't want to fuck this up, I wanted to show Mike that I could handle his cock like a pro. I kept swallowing and soon his tap was off and there was no more cum. I kept sucking just to make sure he was done. Looking up again at Mike as he smiled again. "Oh that was great baby, you and I should have been doing this a long time ago. Now be a good girl and clean this up for me." I took his cock out of my mouth it was still slick and wet. I licked it good and clean. He knelt down and kissed me on the top of my head. He then took a step back then told me to get up and to go to the washroom to clean myself up. I grabbed my purse and headed for the washroom. My knees were a bit wobbly from kneeling. Looking in the mirror my face was a mess. My makeup was looking rough. In the past after blowing a guy I had feelings of guilt but tonight was different. I felt used but I didn't feel horrible about it. I've been fantasising about Mr.Walker for some time now and we'll this wasn't what I had in mind, I was able to be a woman with him. I fixed my hair and fixed my makeup. I was in there for about ten minutes and I was beginning to think I was taking too long. I put everything back in my purse and headed back to the living room. Mike was standing in the living room he took a sip of his beer and held out a fresh glass of wine for me. I took it and thanked him then took a sip. "You clean up well. You know you really do make an attractive woman. How long have you been pretending to be a woman?" Mike asked as he took another sip of beer. I took another sip of my wine. "Well I would wear some of my mother's things when I was around ten or so, then when I was 13 I started to dress more often. When I was around 15 I started collecting some of my own clothes and makeup. (Actually, I did steal a few things from Mike's daughter, I would sneak in their garage and take some clothes, I think they were mostly being donated, but I didn't darn say a thing now.) When I was 16 I would dress every chance, I had. I would go out sometimes. It wasn't until I went off to college that I got more into it and started getting more serious about dressing." Mike smiled at me and walked up behind me and started to rub my arm. "well I'm glad you truly found yourself in college. I find it wild that the little annoying neighbour boy is here in my living room dressed as a little slut. I wish I knew earlier that you were a little sissy, I mean once you turned 18 we could have had a lot of fun together." Mike stood closer to me, I could feel the fabric of his jeans rubbing up against my dress. He leaned in and kissed me on the neck. "You smell good to. You know I really can appreciate special girls like yourself. Back when I was I the Marines, we were stationed in the Philippines, anyways it was a shit hole of a place and of course we wanted to have a little fun. I ended up hooking up with a Filipino Ladyboy, she was pretty hot, she had real tits and she gave the best blowjobs. No offense to you Sabrina, but you can get a lot of practice. A lot of the guys had a Ladyboy on the side, it was no big deal." He moved even closer and he was grinding against my ass. He put his beer down on the table and grabbed my wine glass and also put it down. He then grabbed my hand and walked me towards the couch. He turned me around and kissed me, I kissed him back. I thought we were going to take things to the couch but he then turned me around and slowly bend me over the side of the couch. I wasn't sure what the fuck was going on her. He then stood right behind me and started grinding on my ass again. "Hum, you have a mighty find ass on you. I know watching you this afternoon I was quite impressed with that little ass if yours, you know when you were out by the pool teasing me in that little bikini of yours, isn't that right," as he pushed my back down on the couch really exposing my ass. I didn't say anything and he started to rub my ass. "Sabrina I asked you a question, you were teasing me weren?t you, you enjoyed the attention from me didn't you?" I quiet relied yes, but then he insisted I answer loader. "Yes I knew you were watching and I was flirting with you, I liked the attention." Mike then put his hands up my dress and took off my panties. "Ah that's fine, I'm glad you were flirting with me, but you should have been more careful, if you did that with the wrong man you could have been in trouble. You like the attention of men, well tonight you've got my full attention." I could then tell he was taking off his clothes, he then threw them on the floor beside me. He then reached into the side table and pulled something. I was starting to get nervous but I didn't dare move. He then stood me up and spun me around. He was completely naked. He handed me a condom and to me to be a good girl and to slip the condom on him. I fumbled with the condom and I dropped it. He told me to pick it up, which I did. I then ripped the packaging open and slowly rolled the condom down the shaft if his cock. "Make sure it's on there good and tight," he said to me with a smile. I rubbed his cock making sure the condom was properly on. He kissed me and turned me around and bend me over again. He grabbed something else from the table. "Now Sabrina, I'm going to give you a proper fucking, cause I could tell you could use a good solid fucking. I'm going to use a condom because I don't want to get your sweet little ass pregnant." I could feel his cock head brush my ass cheek. I felt something wet and cold on my ass, he was lubing up his ram rod getting it ready to penetrate me. I could feel his cock head touching my asshole, he was running his cock in a circular direction on my hole. He then shifted his weight onto me and I could feel his cock starting to enter me. He took a minute or so and he still wasn't inside me he then whispered, "Hum baby you ass is mighty tight, have you ever been fucked before?" I quietly said no. He stopped. "Wow you are a virgin, that is so sweet. We'll I'm honoured to be your first Sabrina. Listen this is probably going to hurt a bit, at first, but I can promise you it will get so much better. I'll try my best to be gentle." With that he pressed his cock head harder against my hole. He still didn't penetrate me. Then he pressed even harder and with a pop he was now inside of me. I let out a loud, "Fuck, fuck, for fuck sakes," and it was not in my most feminine voice. Mike laughed. "Ah there we go. Now that wasn't very girlie of you. Remember you are the one who started this, first by shaving your legs, putting on a bra and panties, then slipping on a dress, doing your makeup, painting those nails, strutting around in those heels. If you wanted to look and act like a woman, well this is all part of being a woman." I left his cock head just inside of my asshole. After a minute or so the pain was still there but it was less. Slowly he started to push further into me. It felt like hours but after about five minutes I think he was completely inside of me, I could feel his balls brushing my ass cheeks. He then moved his hands into my hips. "Fuck you have a tight pussy. I hope it doesn't hurt too much now, I'm trying to go slow but I'm fucking horny babe. I'm going to start fucking you, I suggest you just go with it. If it hurts too much just let me know." He then pulled his cock out a bit then slowly rammed it back I to my ass. It did hurt but not as much as earlier. He started to get a pretty good rhythm going as he picked up the pace. Soon I could hear his balls slapping on my ass cheeks. Now he was really fucking me, we were both starting to get sweaty. My cock was rock hard and pinned underneath me on the couch. Mike then moved his hands from my hips and placed them in my breast forms and he continued to fuck me. This is it, I was being fucked just like a woman, I had to admit I was starting to enjoy it, it still hurt but the very idea I was being fucked like a woman was such a turn on. Without warning I let out a loud gasp as I creamed myself. Mike thought that was pretty funny. "God dam baby did you just cum?" I knocked yes. "That's hot, good for you I want you to enjoy this as well." He kept fucking me. My feet were getting sore, I've been in these heels for a while and now I was on the balls of my feet. After about ten minutes, he grabbed my hands and locked his fingers between mine. He let out a loud groan, and pounded my ass even harder until he slowed his pace. Mike came, he came inside of me. Of course he was wearing a condom but still the idea of a man cumming inside of me was quite a turn on. He collapsed his weight onto of me and whispered. "Thanks babe that was fantastic, you are a great may, I'm glad I was your first." He then slowly took his cock out of my ass. He stood up and helped me to my feet. He turned me around so that I was facing him and he gave me a little kiss. I was completely exhausted. Mike said I could stay in Lyndsay's room or the guest room upstairs. He also said to help myself to something to sleep in. I decided to stay in Lyndsay's room. It was fairly nice, it was a girl's room, something I would have liked as my room. I got undressed and slipped on a simple pair of pajamas. I laid down on the bed but everything seemed to be spinning. What the hell happened tonight, I was through a lot not physically and emotionally. My jaw was sore as was my ass. I tried to sleep but I couldn't. I got up to pee, if course like a good girl I sat to pee. When I got up I looked in the mirror and I looked kinda rough. I looked like a woman who just had sex all night. I fixed up my hair a bit and put on some lip gloss. I walked back to Lyndsay's room, but just stood at the door. Then I walked down the hall to Mike's room and I stood in the doorframe. Mike noticed I was there. "What's wrong sweetie, can't sleep?" I quietly replied, "No I can't sleep, it's been a long night." Mike stood up, he was completely naked. He walked over to me and wrapped an arm around me and pulled me closer and gave me a gentle kiss. I kissed him back. He then grabbed my hand and walked me to his bed. "Go ahead sweetie," motioning for me to enter his bed. We both got into the bed, he laid on his back and he told me to rest my head on his chest. So I laid down beside him with my head resting on his hairy masculine chest. He wrapped his arm around me resting in my lower back. I was asleep in minutes. The next morning I woke up early for some reason. I think it was because I was in an unfamiliar bed. Mike was still sleeping. I got up to use the washroom. I decided to go downstairs to make Mike some coffee, to be honest I've never really made coffee but it seems like a good idea. I decided I would bring him the coffee in bed, but that I should change out of these pjs. I looked through Lyndsay's closet but I couldn't find what I was looking for. I quietly went into Mike's room and into his wife's walk-in closet. Now this was more like it. I was looking for some lingerie. I found a black silky camisole short dress, then a lacy black short robe. I looked around and found a pair of black patent pumps about four inches. I quietly walked out of the room. Back in the washroom I brushed my hair and reapplied my makeup. Quietly I walked down the stairs to the kitchen. I found the coffee maker but I had to google how to make coffee, how embarrassing. I made us each a coffee but I've only really had lattes or French vanilla coffee so I had no idea if it was any good. I put some cream in and some sugar then made my way up to Mike's room. I'm sure my clicking of my heels would wake Mike, and sure enough he was still in bed but he was awake. "We'll hello beautiful, well don't you look nice this morning," he said with a grin as he sat up on his elbows. "Thanks, I actually borrowed it from your wife's closet, I hope you don't mind," I replied. "No not at all, in fact I believe I bought that for me wife, but it looks great on you," Mike said as he was checking me out. "I made you a coffee, but I've never actually made coffee before, so I won't be offended if you do not like it." I handed him the coffee. As he took a sip I couldn't help but notice just how naked he was. He really had a great body for someone his age, fairly muscular and hairy but not too hairy. I also couldn't help to notice his big fat cock was semi hard as he laid there. Morning wood I would guess. "Wow, this is really strong coffee," as he let out a chuckle. "Oh no, I'm so sorry, I can make some more if you like" I tried to explain. "No it's fine sweetie, I appreciate the effort we'll make a good little housewife out if you some day." As he put the coffee down on his side table. I was a bit embarrassed by the coffee but I was a bit turned on by the idea of being a housewife. He patted down on his bed motioning for me to sit down. "How is Sabrina feeling this morning?" I sat down beside him. "I'm feeling ok, I'm a bit sore, still tired, but not too bad." I can't believe we are talking about me being sore after all the reason my ass was so sore because my older male neighbour rammed his cock in my butthole last night and we were talking about it as if it wasn't a bit deal, weird. Mike out his hand in my knee. "Ya sorry about that, the first time can be kinda rough, don't worry it will get much better." We both had an awkward smile, I apologized again for the coffee. "Sorry the coffee was so bad, him maybe I can make it up to you some other way," as I reached behind me and gently began to stroke his semi hard cock. He smiled at me and I gave him a devilish grin back. "Well that's a good girl, you are really learning how to be a woman, please enjoy yourself." I turned towards him and continued to stroke his cock. I've given a hand job before but he was just a boy compared to Mike's cock. His cock quickly went from semi to completely rock hard in seconds. He pulled my head closer to him and kissed me. We continued to French kiss, while all the time I kept jerking him off. After a few minutes, he told me he was close to cumming. I kept stroking him and moved my face closer to his cock. I could see the precum slowly ooze out, I quickly swallows his cock head and let Mike cum in my mouth. I sucked down every last drop of Mike's goodness. After licking his cock clean I looked up at Mike and he was smiling at me. "God damn girl that is one awesome fucking way to wake up in the morning. Listen why don't you hit the shower and I'll make us some real coffee." In the shower I used Mike's wife's razor to give myself a good shave both my face and legs. I'm not very hair but Sabrina needs to be smooth. When I got out of the shower I could smell Mike cooking us breakfast. It smelt really good. I started to get dressed, I wasn't sure what to wear. Lyndsay's closet had a few items, but I decided to go with a cute pair of jeans shorts, they would show off my ass nicely. Lyndsay was a bit smaller than me so the shorts were a bit tight. I went with a light pink peasant top that went off the shoulders. I was going to wear a pair of flip flops, but this girl does love her heels, so I decided on a white strappy sandal with a three-inch chunky heel. I went with a simple makeup finishing off with a light pink lipstick. My hair looked OK, but I could have done better. I grabbed my purse and headed downstairs. Mike was just finishing up breakfast. "well don't you clean up nicely, please have a seat. We sat and are breakfast, it was nice conversation, nothing really awkward, you know considering. He actually made me a latte since I didn't drink regular coffee. After breakfast we decided on a plan, actually Mike decided. We would take his motorcycle back to my mother's car and we would look for the keys. If we didn't find them then Mike would call someone to help, he had a friend who was a mechanic. Mike handed me a black helmet with a pink butterfly on the back, he helped me do it up. He joked that if we were going to go riding enough then I would have to learn how to buckle my own helmet. He put my purse in the side compartment and told me to get on. It was a nice bike, a Harley. I didn't really appreciate it last night but with the roar and the vibration of the engine it is quite the feeling when a gurl is tucked. As we started to drive off Mike told me to hold on to something. I wrapped my arms around his chest. When we got back to the car, we looked for the keys, actually Mike looked through the bushes while I stood around. I was getting plenty of looks from men driving past, I credit my short shorts for that. After 30 minutes he found them. I thanked him and gave him a big hug and a kiss on the cheek. He said we could go home or we could go from a ride up the coast a bit. I figured why not, when's the next time I'll be dressed as Sabrina and get to go on a motorcycle. We drove for about 20 minutes, and we stopped at a nice look out. Mike suggested he take some photos of me with the nice background. I agreed. I was trying to be as girlie as possible for the photos, it was fun. As we were leaving, a nice couple offered to take a few photos of the two of us. I thought that was pretty funny, but Mike said sure and we got some good photos of the two of us. Alas it was time to go. We had to drive back so to my mother ?scar. On our way back, I did reach around with my hand and gave Mike's big cock a squeeze in a few occasions. He didn't seem to mind. Once we arrived at the car I gave Mike back his helmet. I told him thanks for everything. He told me no problem and that it was nice to finally meet Sabrina. He also told me to be more careful bout there. As he started to walk away I called out his name. "You know Mike, I'm going to be alone in that big house for a while, you should probably come check up on me from time to time." He smiled and walked back towards me. He grabbed me again and pulled me close to him and this time I kissed him first. We kissed for what seemed like minutes. We actually got some honks from passing cars. Then Mike whispered to me. "Ya I can drop by, but maybe you'll feel safer if you stayed with me at my house, I miss having a woman around." I smiled back. "Ya I'd like that, it will give me a chance to perfect my coffee." I gave him a wink. I turned and walked away and he slapped my ass as I walked away. I got in the car, I watched Mike ride off and I just started laughing in the car. I started the car and was about to drive off when I put the car back in park and decided to text Kimberly. Sam: So, I had one crazy Fuckin' night!!! I uploaded three photos to her. One of me dressed as before hitting the club, one with me on Mike's motorcycle, and the last one was with me and Mike. This was one of the photos that nice couple took of us. It was actually a good photo, Mike had his arm around me. Kimberly is going to shit herself when she sees them. End of Part One.