Dear Diary Part 11: Burgundy Wine And Moonlight/Date Night free porn video

Dear Diary, How did I get here. Someone please pinch me. I was asked on a date from a real sweet guy I met online a while ago. I didn't know what to make of it all and got swept up into an electric current pulling me into the unknown. I have always been drawn to the idea of dating a guy but I never in my wildest dreams thought it would actually happen. I've only ever dated girls before so when Dalton asked me to a date, I was as excited as I was petrified. He expected me to be the girl on the other side of the table. How should I act and react to things from the female perspective. I had no experience until now. A day after I called him back, he sent me a text telling me that he was looking forward to meeting me and that he had already made the reservations to a classy restaurant in our little gay-borhood. I heard of the restaurant before. It was a local place that many gay couples frequented. I had never been but knew about it through magazines and internet articles. I was happy he picked that particular place because I could feel safe knowing that I probably wouldn't run into anybody I knew. I could "hide" as it were. It was sweet of him to pick a place he thought I would feel comfortable in. He's already earning points! I felt safer already. And taken care of. The next day at work the thought came over me. I needed a date night outfit! I didn't get much done at work that day. I was distracted by this idea. I kept thinking about all the pieces I have in my wardrobe. What was I gonna wear? My leopard print mini? Too clubby. Shorts and cute top? Too young and not classy enough for the place we were going. Nothing seemed perfect. Truthfully, I didn't just want to blend in, but I wanted to impress Dalton. So I decided I needed to hit the shops and see if I could find something that was sexy and said to Dalton that I put in the effort, too. If he was going to meet me for the first time, I wanted to make lasting impression. I wanted to look and feel sexy, yet classy, but I also wanted something that screamed "take me and don't let go!" I had the day off so I decided I'd drive to the next town and do a little shopping for a new dress. Monday's at the mall, during the middle of the day, have always been this cross dresser's safe haven. It was barely crowded and I had time to roam the shops. I've always been a little hesitant at first so when I first got there, I just passed by my favorite shops, casually window shopped, mostly trying to work up the nerve and courage to go in. I love this mall because it has a lot of cute stores but also the big brands as well so there were a ton of places to look. After about 30 minutes of playing the courage game, I walked into one of my go to stores called The Closet. I love this place. It caters to the young and fun girl in me. No doubt I'd find something appropriate here and at a nice price. So I walked in and am greeted kindly by the sales girl at the counter orangizing hangers. "Let me know if you need any help," she said. "Thank you," I replied. Slowly, I begun my search. There was only like 2 or 3 ladies in there but I was still trying to get my legs. But as more time went on, once I got more comfortable in my skin, I found my shopping groove. There were so many cute things there that I could build an outfit with. Tops, shorts, skirts, jackets, etc. I picked out a few things and walked around like I belonged. With an armful of cute items, I turned towards a wall and saw this really simple yet sexy ensemble hanging in a mannequin. It was a deep red, burgundy color, which was different than the rest of the pastel and black items I usually would wear. It was sort but still had a slit on the side for the leg. I would be showing all kinds of leg power in this and to be completely honest, I've always felt that those were my strongest assets to my feminine image. I loved its 3/4 sleeves, too. Those always made my arms and shoulders look more feminine. It defined sexy. I had to try it on. I checked through the rack and found my size! Yay! I grabbed a bra from the rack and headed to the dressing room. I waited a bit before the sales girl saw me. "Hi," she said kindly. "Can I help you?" "Do you think I could try these on?" I asked shyly. "Yeah! Sure go ahead!" she said with a big smile. She hands me a number and takes me to a room. This whole process was still exciting to me. I stripped off my male drabness down to my panties. I put on the bra and stuff my socks in it to emulate the breast forms I have back at the apartment. I needed to see if the dress was bra friendl or would I need to glue on my forms. I unzipped the dress and stepped in, pulled it up over my thighs, then over my bra, put my arms in and zipped it up. It fit beautifully! Like it was meant to be. It had a soft stretchy fabric and sat on my body really nicely. And that leg slit was the selling point. I immediately felt sexy. I unzipped it and put it on the hanger and walked out the fitting room with a glaring confidence. I even picked out a nice gold necklace to pair with the dress. I walked out of The Closet beaming, proudly holding that cute pink bag they put your purchases in. Sprung with confidence, I walked straight to Victoria's Secret. There weee quite a few ladies shopping when I walked in, but they didn't really seem to care so I felt more comfortable and kind of blended in. I picked out one of those new seamless bras in a flesh colored tone. On my way to the cashier I saw a table with a really sexy pair of black lacy cheekies that I had to have. The girl working there didn't even bat one eyelash at my stuff. She rang me up with a smile and told me to have a great day. It was a very positive day which I took as a sign. I still love how cute the Victoria's Secret bag is. Marchesa was home when I got home. She must have got off early and she greeted me as I came over in. "Hey babes! You went shopping I see." "Is Michelle home?" I asked. "No she's at work still." Marchesa followed me into my room. She pulled the dress from my bag. "Oooh is this for your date?" she said with a coy smile. "This is very nice hon." I pulled out the accessories from the bag and showed Marchesa. "I thought this would look nice with it too." "Wow I'm impressed with your taste," she said. "Thanks M." I grabbed a pair of my patent nude pumps, closed toed, from the back of my closet where I kept all my shoes. "I think these would look nice with it. What do you think?" I asked. She held up the shoes to the dress. "He is going to love you in this," she said. She put the dress and shoes down on the bed and picked up the Victoria's Secret bag. "Is this for the date, too..?" she coyly gave me a look. I grabbed the bag from her. "We'll see M." "Oookaaay!" she exclaimed with a big smile. I scheduled an appointment at a local salon for a full body wax. I had never done it before and called around to find the right place to do it for me. I called this one local place and told them about my situation. They were really accommodating and told me not to worry and that is be well taken care of. Before I booked, I asked if they have taken trans customers before. She responded without hesitation, "Yes absolutely!" If I was going to go through with this date thing, I had better do it right. I wanted to look nice and clean and feel smooth to the touch. Plus my curiosity got the better of me and all the girls I've spoken to in the past raved about it. So I booked it for the day of the date so I would be soft and silky not just for Dalton but for my confidence to step out as a woman. The week dragged on and on. I kept daydreaming how the date would play out. I used my free time to work on the finer details of being a woman. I watched tons of videos trying to practice feminine body movements, feminine etiquette, and practicing Kimberly's voice. I was committed to the art of being a woman. I also wanted to make sure I got every detail perfect. I already learned a lot over the years but I learned a lot more in my little crash course. I had a strict beauty regimen that included masks and moisturizers and face washes that I bought at Ulta. Every night and every morning I took care of my face. And of course got plenty of hours of beauty sleep. I also tried out different tucking methods. I didn't want anything popping out at the wrong time. Heaven forbid! Saturday morning finally arrived. I woke up with a spring in my step, giddy with anticipation but wrapped with frenetic anxiety. I had to get to my waxing appointment. I was so scared I didn't know what to expect. I wore a pair of non-descript black bikini panties under some generic sweats and a tank top. I was welcomed in the salon by a wonderfully made up woman whom I spoke to on the phone earlier in the week. "Hi I'm here for my appointment?" I said shyly. "The full body?" she replied. "Yes," I said. "Ok hon follow me," she walked me to a room in the back. She introduced herself as Maria. She told me she had been doing this for a long time and told me not to worry that I was in good hands and that she's seen it all. I felt immediate relief at that moment. Since I asked for the full wax, told to strip down. All. The. Way! With all my delicate parts out display. "Get yourself comfortable and I'll be back in a sec with my materials," she said as she closed the door behind her. I have never been naked in front of anybody before let alone a woman so I was a bit nervous. So there I was standing in the room about to get naked. First my shirt, pants, then panties. I got on the table which was a bit cold on my bare body. A few moments later there was a knock at the door and it was Maria with the stuff to get rid of my ugly body hair. She explained that she was going to use the sugar wax technique. She instructed me to lay on my back. "Now you said on the phone that this was your first time getting a wax?" she asked as she applied the wax to my leg. "Yep," I exclaimed. "Ok you might feel some pain," she said. "You ready hon?" "Ok," I said with a heavy breath. "I'm ready." She ripped it off and to be honest, it wasn't that bad. I had survived the first of many rips. While it wasn't exactly relaxing, it wasn't crazy painful like I had built it up in my head. About a half hour went by when she told me she was done with the legs. She then moved on to my arms. That hurt a bit more than the legs. She then did my underarms. I've always shaved, and that hair seems to be the first that comes back, so I was looking forward to getting that removed. She was great at talking to me during to keep my mind distracted from the pain. She kept the conversation going throughout, mostly her explaining to me what she was doing. She told me that she's done waxes for women, men, crossdressers, everybody. She also said she's been friends with people in the drag community for years and that nothing bothered her. "So what do you got going on tonight hon?" she asked casually. "I'm going to dinner with a friend," I answered. "Is this like a date or?" she asked. "Yeah we're seeing if it goes somewhere," I said. "Don't worry hon he's going to love you," she said. "I hope so," I replied. Sneaky sneaky, girlfriend! It was time for the Brazilian wax. I watched a ton of videos and read articles online on what to know and do before. I was a bit nervous but he explained to me what she was doing as she was doing it to distract my mind. The first tear was unbelievably painful. She waxed everything, and I mean everything. Oh. My. God! I had a few tears well up in my eyes. I even let out a minor grunt. The more she did it, the more numb I felt. I had gotten used to it after a bit. I was trying to distract myself as well. I kept telling myself that it would all be worth it, to feel as smooth as I would about to feel, feeling sexy and lighter, and hoping that Dalton would also appreciate the effort. After an hour or so, I was completely waxed for the first time. Maria oiled me up and down with jasmine oil all told me to avoid direct sunlight for the rest of the day. The waxing was all done and I felt like a new woman. I've never been completely free of hair down there before and the feeling was exhilarating. I felt like a feather floating on air. I walked with a different sashay. I had a date to get ready for! It was an all day extravaganza getting myself ready. He was going to pick me up at my building at 7 so I only had a few hours to get prepped and ready. When I arrived back home, the place was empty. I checked my phone and Marchesa said she would be staying at her friends that night. With Michelle also out of town for work, I had the whole place to myself. I sat in silence for a moment, contemplated all that work I just went through. I was really going through with this. At that point I felt 100% committed. But still anxious. I put my girl jams on and started the femme extravaganza. I got my dress out and hung it on the door of my closet. I pulled my heels out of their box. My new vickys secret sexy little things spread on the bed with my new bra. I took my soft silky kimono out of the closet. I got my make up box out and set that and my hair extensions on the big vanity in the bathroom of our condo. Looking at all of my stuff, it was time. I disrobed out of my sweat pants and put the silky kimono on. I tied my hair up in a tight bun and tried my best to get all the flyaways so not to mess up with my make up. I sat down in the vanity chair and looked at my un made up face in the mirror. I took a long look at myself. I examined my skin to see if there were any stray hairs left behind from when I shaved earlier. My face was smooth. An empty canvas waiting to be painted. The scent from my make up box was so intoxicating, like a pink drug that released all that pent up feminine energy I had built up for the past week. I realized that it had been a while since I have completely transformed into Kimberly. I was so excited to start to long, beautiful process again. Primer, foundation, concealer, my base was set. Blush and brozer, highlights whereever necessary. Got those brows on fleek. My eyes were next. Just enough shadow and liner to compliment my brown eyes. I used false lashes on both the tops and bottom lashes so if I wanted to blink prettily, Dalton would notice how cute my eyes are. I used a nude toned pinkish lipstick. My lips looked absolutely kissable. It all came flowing back with ease. It was all so natural feeling. I was an artist using my face as her canvas. Throughout this, I would be practicing my pitch in my voice, practicing what I would say to Dalton, and all the other feminine behavior. After about an hour or so, there was just one more thing to to, set my make up. Like Christina says "lips, eyes, cheeks, face, give it style, grace." Just as I was about to start my hair, I got a text on my phone. It was from Dalton. He said he was leaving soon and that he couldn't wait to see me. Omg! I was getting so nervous at that moment. It was really going to happen and very soon too! I replied saying that I was getting ready and that I was excited to see him. Clip by clip my hair, my hair transformed into a luxurious, soft, bouncy do, layered with light brown waves that perfectly accented my real hair. It almost looked like the new princess', Meghan Markle's, do. OMG I just love her! She's so pretty.. but enough about her this night was about me. With my hair and make up all done, I had my hands free to begin the tucking process. Earlier in the week, I had found a fantastic tucking method to hide away the parts downstairs. I put on my nude gaff over it and then slid my sexy new black Victoria's Secret undies over. Now that I had that part hidden away, I grabbed my C cup falsies and took off the adhesive strips and stuck them to my chest. I put on my new bra from Victoria's Secret and clasped that closed. The girls were set. I seldom do my nails, but tonight felt special and I wanted to go all out for this date, so I applied some cute press ons in nudish pink. Usually when I dress, it's all about the process of getting ready. I love all the tiny details of getting dolled up. But tonight was all about the final result. I had to look perfect, for Dalton, and for myself. I needed to see if I could pull it off entirely from head to toe. I had just started to actually get dressed when I heard my phone beep. It was Dalton telling me he was on his way. That mean he'd be at my place soon! I hung my kimono in the bathroom and grabbed my dress and in its beautiful fabric I went. It went on so smoothly, as if the burgundy dress was made specifically for me. Inch by inch it found its way to all the right parts of my body's frame. The material was luxurious. I loved the way it felt on my body. I stood at the full length mirror in my closet, and just admired for a minute how nicely it sat on my as I made a few adjustments. I thought it looked gorgeous on me. I accessorized with the beautiful gold necklace I bought with the dress earlier in the week. The look was almost complete. My phone beeped. It was Dalton again, telling me he was outside. OMG! I wasn't finished yet so I told him that I would be a few minutes and that's I'd text him when I was done. He told me to take my time. So sweet. I didn't want to keep the boy waiting too long. I quickly put my nude heels on. I packed a clutch with a the essentials in it like ID, credit cards and cash, compact and lipstick, keys, and phone. A little spritz of Daisy purfume of my wrists, behind the knees, and nape of my neck. I did some final touches and adjustments, made sure my dress looked nice on me, that my make up and hair looked primed and ready for our first face to face meeting. Then I texted him, "I'm ready! Come get me." My doorbell rang. Eek! I tried not to panic but the bell sound tightened my stomach and my heart was racing. I clipped to the door. He was literally standing on the other side of the door. I took a few deep breaths to calm nerves. Then I opened the door. I felt a cool wind caress my knees. The door must have opened from some force other than my own. It revealed a nicely built boy, dressed in really tight jeans, a white V neck tee, and a black blazer. His hair was put up in a small bun and he looked freshly shaved. One thing I didn't notice on our previous Skype sessions is how deep blue his eyes were. Also a lot taller than I imagined. He was a couple of inches taller than me and I was wearing high heels! I managed to get out a single word through baited breath. "Hi." He returned the greeting with own, "Hi." He lifted up a beautiful bouquet of flowers. A boy bought me flowers! How thoughtful was he? "I got these are for you," he said as he handed me the bouquet. "They're lovely!" I exclaimed. "Come in while I put them in water." I put the bouquet in a violet vase and put it on the kitchen table. "I hope I'm not being too forward but you look gorgeous in that dress," he said staring longingly. "Oh! Thank you," I smiled. "It's new!" I said. I continued to arrange the flowers. "These are really nice. This is the first time anyone's given me flowers." "You should get them all the time," he responded. He was already dropping lines on me. But I did not mind it at all. I enjoyed the compliments. What girl wouldn't? I grabbed my clutch from the kitchen table. "Ok," I said. "I'm ready now." I closed the door behind me and locked it. I was fully committed at that point. On the way to the car, there was that awkward moment where the two of us didn't know how to act or which boundaries were ok to cross. Do I hold his hand? Does he put his arm around my waist? You know, the little things like that. Nothing major. He did open the door for me, which I thought was very sweet. He had a very nice car, too. Clean, leather seats, a BMW. The drive there was quiet but peaceful. I think he was nurvous too. It was also strange because we could go hours talking online about stuff but I chalked that up to first meet butterflies. We found a great spot near the restaurant. He turned the car off. It was a moment of truth for me. A moment I didn't plan because I was so wrapped up in everything else. Before we left, my confidence was sky high, but the closer we got to the place, I felt that confidence wane. I was scared to the point of shaking. My heart was racing too. I was about to make my debut on a busy night on a busy street in the city where I live! So much was going through my head. What if someone I know notices me? He was about to open his door. "Uhm, Dalton-" I started. He stopped his motion and turned to look at me with those deep blue eyes. "Everything ok Kim?" I was about to tell him I wasn't ready but looking at his eyes, I just couldn't. I needed to do this for him and for myself. Exasperated, I asked Dalton, "Do I look ok? Like, do I, you know... pass?" "More than that," he said. "You look beautiful." I don't know what he did but my confidence meter rose again. I felt lighter. I just looked into his eyes as he said that and I just believed him in my heart. He got out of the car first. I took a couple more heavy breaths. He opened my door and took my hand like a gentleman. I adjusted my dress as I got out. I didn't want to be flashing people my black panties there. He then wrapped his arm around my waist lightly and we walked like that to the restaurant. It was the first time we made physical contact. It felt really nice and I felt protected. I get to the restaurant and it's a romantic setting that's dimly lit. The hostess was sweet and took us to a table immediately never batting one eyelash. It's a table for two and we sat across from each other. He even took my seat out for me! OMG! He really treated me like a princess. We stared at one another for a moment. It was surreal to be sitting across from someone I've met online while being completely dressed to the 9s. Dalton broke the momentary silence. "I'm so happy you called me back. Can I say again how beautiful you look?" I smiled and thanked him. "You can say that as many times as you like." The waitress came over and took our drink order. Dalton ordered a seltzer and I got the house Port burgundy wine. She asked to see my ID! Normally I wouldn't mind being carded, but I didn't want Dalton to see my license picture. I reluctantly gave it to the waitress but she was sweet and didn't bat an eyelash. I think this place is used to seeing us girls, as I read in the reviews. We got our drinks and we were talking about how we heard of this place. He said he never knew until I told him that I'd like to try it out. He listened! We chatted for a bit about the menu and what our favorite things were, being a little flirty as well. My confidence was really high and I could tell by the way I was interacting with my environment. "So what's your favorite color?" I asked him as I took a sip from my wine. He stared at me with those blue eyes of his. "I'm liking red a lot," he said. "What about you?" I flirted right back. "I love all shades of Pink, but I'm really loving Blue these days." And I gave him a seductive stare right back. The whole dinner was filled with these flirty moments and innuendos. I had a lot of fun playing the role of a woman. It was such a rush. We laughed and I felt a bit of a connection to him on a more deeper level. I forgot where I was and how I was dressed. We shared a plate of oysters. I got another wine. We flirted some more. He told me again how beautiful I was. "What do you find most attractive about us girls?" I asked. "The androgyny, and that you are often more girlish compared to other girls," he said. "And more forbidden." "That is sexy, isn't it?" I said. "Yes, yes it is," he said. "I like to think I'm forbidden," I joked. He just sat there and smiled at me. I was having so much fun that the evening became a blur. It could have also been the wine. I went to use the ladies room, once again could be blamed on the wine, and adjusted my make up whilst in there. When I came back, he asked if I was ready to go. He told me he already took care of the bill! We left the restaurant and walked along the harbor. I held his arm along the way. The man was quite fit! The night was quiet and I could hear the water splashing along the rocks. We walked by other couples enjoying their nights out. I asked him if we could sit for a bit as my feet started to tire from wearing high heels. I don't remember the last time I wore them this long. We found a bench overlooking a pretty part of the harbor. We chatted some more but it became more serious in nature. The moonlight reflected off the surface of the water and bounced off his lovely blue eyes. He asked what changed my mind. "Why did you call me back? Don't get me wrong I'm happy you did, but I'm just curious." "I wouldn't forgive myself if I didn't," I said. I was feeling a bit chilly so I inched closer to him. We sat for a moment. He then put his hand over my cold, exposed upper thigh. It was probably one of most intense feelings I've ever felt. I quivered and my skin got all goose pimply. "You ARE cold," he said. He moved closer and put his arm around me. I looked at him and thanked him. I gently leaned my head forward. His also moved towards me. I closed my eyes. Our lips delicately met. Before I know it, our lips were pressed firmly against each other's! I didn't know what came over me to do that but it was a very hot moment. It was my first time kissing a guy. At that moment I was really feeling it. The tuck started to unravel a bit. "Let's go back to my place," I told him. "Are you sure?" he said as our foreheads leaned against one another's. "A thousand percent yes!" I said. We couldn't get there fast enough. On the way home, we'd smile at each other, excitedly pondering the naughty thoughts running through our dirty minds. He gently kissed my neck as I unlocked the front door. OMG I couldn't open the door fast enough. I couldnt believe I actually invited a guy over! As we walked in he turned my body towards his and kissed me deeply. I'm talking DEEPLY. Tongue and all. I accepted his lips with pleasure. I dropped my clutch on the ground and it made a big sound. It stopped us for a minute just long enough for me to lock into his gorgeous blue eyes and lead him to my bedroom. "I got something for you," I told him. "Sit here and don't look." Dalton sat on the bed with his eyes closed. I took my heels off and tiptoed to my wardrobe. I pulled out my sexy red chantilly lace teddy bodysuit I had bought from Victoria's Secret. It is a very cute and sexy piece with a plunging neckline, keyhole cutout in the back and a thong bottom. I turned to see if Dalton was behaving only to see him peeking out the side of his eyes. "I said no peeking!" I threw a bra at him. "You wait here like a good boy. I'll be right back for you." "Yes ma'am!" he exclaimed. I snuck the lingerie with me out of my room and into the bathroom where I disrobed. I took my dress off carefully as to not mess up my hair or makeup. Then I took off my bra. Amazingly, the girls were still stuck on my chest firmly. I kicked off my knickers. I used some of Michelle's Rose oil lotion on my body to give it a seductive fragrance. I let it sit for a bit before I stepped into the lacy lingerie. I made some adjustments to those lower parts as I slipped it on. Since I'm not naturally large in that department, it can sit nicely in the lacy front panel. While not flat, it's still pretty cute. Never in my wildest dreams did I ever think I'd be standing in a bathroom wearing lacy lingerie about to show it off to a guy who was in my bedroom. I was scared but the more scared I got, the more sexually awoke I got. So I said "eff it girl, you look hot tonight and deserve to have a little fun!" I tied the kimono around my waist, made some adjustments to the girls to make sure they didn't fall off, and back to the bedroom I sashayed. I found Dalton sitting on the bed minus his pants and shirt. He was wearing white spedo like undies and he was FIT! I'm talking 8 pack fit girls. That doesn't normally do it for me but that night it did. His body was also smooth like he gets waxed. This was really going to happen. I was a little bit scared but the more scared I felt the more turned on I got. "Ok you may look now!" I said. "Wow, you look so beautiful Kim," he said. I let out a short giggle and did a tiny turn to show him the kimono. "Would you to unwrap me?" I asked as I walked toward him. He immediately "rose" to the occasion if you get what I mean. I placed my hands on his knees and stood in between his spread legs. It got very warm very quickly. He pulled on the belt and undid the knot and the kimono swung open, revealing the lacy red lingerie. My heart was beating so hard I could feel it in my head. I shimmied my shoulders and the kimono fell to the floor. My entire ensemble was exposed. I moved my hands up his rock solid abs and laid on him. He kissed me on my chest. I could tell he was very excited because he was very hard under his manties. He turned me over so I was laying on my back. He kissed me up my neck and moved slowly to the mouth where he placed his tongue. He gently stroked me then I got hard. He removed his underwear. He was pointing straight towards me. OMG! This was crazy. Then he placed his firm manhood, and that's putting it mildly, over my lace covered cute little one and methodically gyrated on top of me. It had awoken this wild sexual energy inside of me. There was lots of heavy breathing action, especially from me. What he did after was just magical. He spread open my legs. He softly kissed my knee, up my thigh, then my lace covered penis. He unfastened the fastener that hooked the bottom part of my teddy and it flew open, and it exposed my bare bottom and anal opening. I was fully erect. He played with my bottom, gently and softly teasing the area between my bottom and penis. It was enchanting. He "accidentally" put his finger in. "Oops," he said. "Do that again!" I said breathing heavily. He did it some more. Then added another finger, kind of doing the walking man thing with his fingers a bit and continued to tease me. He stopped and looked at me in my eyes. "Kim, would it ok with you if.. you know.. I went inside?" he asked. "I don't know," I said shyly. "I've never.. done that before." "Me neither," he said. "I can wait until you're ready." He went back to work, kissing my penis, playing with me down there. "Dalton," I stopped him. He sat up and looked me. "Yes Kim?" I couldn't deny it any longer. I wanted it badly. I had been fantasizing about this for the last year and now I'm finally in the position, in more ways than one. Who was I to say no? "I'm ready." He flashed a nice smile and leaned down to kiss me on my mouth. It was firm and tender. He knelt on top of me with my legs spread open and I'm on my back. I was about to get plugged and it was with my consent too! OMG! He placed the tip of his head and slid it over my taint region, down to my anus. He softly carresed my legs. "You're so smooth Kim," he commented. Then in he went. It was a tight fit, seeing is how I've never had anything enter me there before coupled with the fact that he was not a small man by any stretch. Quite large in fact. He pushed it in methodically. Little by little he was in until I felt his balls touching my bottom. He went in and out. It was so hot! I moaned a few times. He called my name out and that got me nice a boiled. "Kim!" he yelled out. "Oh my god yes!" I cried out. He went faster and harder. The sound of his naked pelvis smacking my naked ass was turning me more on. I didn't feel any more tightness or pain just pure pleasure. He looked at my in my eyes and I looked back into his. I can feel the feeling like he's about to go. I let out another feminine moan. I grabbed his strong pecks. His body was sweating. "Oh Dalton!" I cried out. He let out a grunt. Then I could feel him explode inside me. It was a different feeling but such a beautifully intense feeling. His stuff was dripping out of me and down my ass crack. Then I came, his penis still firmly planted inside of me. He kissed me as he pulled out. He laid next to me. I was still reeling from my first time trying anal. It was the best orgasm I have ever had in my life. I was still breathing heavy. "That was amazing!" I told him. "It was!" he said. "Hey Kim, can I tell you something." "Sure hon." He turned towards me and spoke softly. "You were my first." I couldn't believe this! He was so experienced. His first what? "Your first?" I asked. "Ever," he said. "And you were mine too," I said. He leaned and we kissed again. We cuddled together then we eventually fell asleep. A short while after, I woke up next to this naked man, and wanted to clean up, change into something more comfortable, take off my girls, etc. I got up and felt him move, but I didn't want to disrupt him.I whispered in his ear that I'd be right back. I put my girls away for the evening and jumped in the shower. I washed him out of me. I was actually ok with keeping his stuff inside because it reminded me of a very sexy time, but I want to be clean. I replayed the evening in my head while in the shower. I was even more confused about myself. I really enjoyed myself, all aspects of being Kimberly that night, but I wasn't sure if I was ready to commit to that life. I slipped into a champagne colored slip and my new black cheekies and went back into the bed with him. He turned over and held me as I closed my eyes and went back to sleep. The day was dawning and the light was shining through the cracks of the blinds. My eyes opened up to an empty bed. I sat up and noticed I was still in my slip and had my hair extensions still on when I remembered that my roomies would be coming home soon after. I got up to go clean the bathroom when I saw Dalton in the kitchen making tea. He had his clothes back on. "Kim! I'm happy you're up. Is green tea ok?" he said. He placed the cup on the coffee table and I sat down all girl like and crossed my legs and held my tea. He sat next to me with his cup. He put his hand on my thigh and took a sip from his cup. I started to get all turned on again. "I like this look, too, Kim," he said. I felt flattered that he liked my just waking up look. He told me he had a great evening but that he needed to get to the office. "Oh no!" I said. "Don't leave me here all alone like this," I leaned over on the couch all sexy like, teasing him by stroking my tip toes over his manhood. He leaned over me, sliding his hands up my smooth legs and up my slip. "Mmmm, I wish I could stay!" he lamented. He stood up and kissed me on my forehead. I walked him to the front door and he told me he wanted to see me again. Then we kissed again. I couldn't stop doing that! He told me he wanted to see me again and I told him that I would like that. We said bye to each other. I blew him a kiss before I closed the door. I already miss him. But I had some cleaning up to do before the ladies get home and ask questions.