Tammy's Transition free porn video

Tammy's Transition My name is Tom and I have been a cross-dresser for years. Like many of us it began in my early childhood. I tried to suppress my urges by dating girls, participating in athletics and just trying to be your general macho man. I would go for weeks even months without trying on female attire only to find the draw back would become overwhelming at times. I would get that sexual buildup, dress in something pretty and then after pleasuring myself would feel guilty. This vicious cycle went on for many years. Two years after I graduated from college I met a wonderful woman, fell deeply in love and were soon married. We were happy in love and had made plans for our life together. Although I loved Cynthia immensely it was a double bonus that we were very close in size. I'm only 5 feet 7 inches tall and weigh 130 pounds so meeting a girl similar in size wasn't hard. I pursued a career as an office manager in the headquarters of a large retailer while Cynthia was a clinical psychologist. After a couple of years it all started to unravel when Cynthia caught me secretly cross-dressing. She was devastated and after a few months started having an affair. The marriage ended peacefully and after time Cynthia and I became close friends. Then, Cynthia and Brian, her new husband, moved away. Brian took a job at a prestigious company. We soon lost touch of each other. After I turned thirty I took stock of my life. I was working, I liked my job and I had many friends but something was missing and I just didn't feel fulfilled in life. I lived alone and dated occasionally but I just couldn't find the right person to start a relationship with. I had a small wardrobe of woman's clothes and I continued to dress on occasion but even that was boring after a while. I would dress up but felt I had nowhere to go. I wouldn't dare venture out dressed. I was too scared to get caught again. But the thought was exciting to me. Often my dressing would subside for day's even weeks until I would see a pair of shoes, or that perfect skirt or that must have handbag. I would surf the internet and started to correspond with several cross-dressers. A few of the girls urged me to set up a personal web page. After I learned how to do it I took a few photos of myself and opened up my web page. I liked the way I looked in the photos and it became apparent others admired my look as well. I quickly compiled a list of gentlemen admirers. Many were just down right sick and most were creepy but a few of the men were very polite and we corresponded regularly. Of course many of these men wanted to set up dates and I was not interested in that. I still had not even ventured out of the house dressed. Unlike my cross-dressing sisters, something about the attention from these men started to pique my curiosity. I loved the attention I was generating and I pushed my goal of looking female further. The attention was exhilarating and soon I began to fantasize, when dressed, what it would be like to date and have a relationship with a man. Always my fantasies revolved around faceless men that would completely sweep me off my feet and shower me with romance, attention, love and affection. I found myself thinking about what it would be like to be the wife in a relationship. I began to question my thoughts. I grew confused and frightened about where this might lead too. Then out of the blue I got a call from Cynthia. It had been a couple of years since we spoke, so it was good to catch up on our lives. She and Brian recently moved into a new house and were ready to have kids together. Cynthia set up a practice and was beginning to build a list of clients. Brian quickly moved up in his company and was recently selected as a partner in the business. We talked for hours and it felt good to get re-acquainted again. At one point, Cynthia asked how my cross-dressing has progressed. I was surprised by her candor, but she was genuine in her questioning. I told her it was pretty much the same, except only now I don't have to sneak around the house since I lived alone, I can dress when I please. She informed me that as a result of her relationship with me, she had become interested in cross-dressers and transsexuals and had several clients in her area. She apologized for not being more understanding during our relationship. As we were saying our goodbyes she urged me to come and visit and stay a few days with her and Brian. I said thanks for the invitation and I'll give it some thought and get back to her. It felt good to talk to Cynthia and I began to think about her consulting with girls just like me. I have been feeling a little confused about me lately so I decided to take her up on the offer to visit. A couple of days later I called her back and she was delighted to hear my plans. She assured me that Brian is delighted to have me as their guest as well. Finally after a few weeks I flew out to visit Cynthia and Brian. Cynthia met me at the security exit and we laughed and hugged for several minutes before we departed for her house. She looked great and was dressed very well. Of course I was dressed in my male clothes and had not brought any female clothes. We barely had a pause in the talking as we drove to her house. As we pulled up I couldn't believe the size of their home. It was massive. They were obviously a very wealthy couple. I let her know how proud I was of her for what she has made of herself. We went inside and after showing me the house for almost an hour Brian came home. It was good to see him again. He asked if I wanted a scotch and Cynthia quickly responded with "we'll both have a white wine." I was impressed that she knew exactly what I wanted. She smiled and winked at me. We sat and talked for hours and finally retreated for the night. The next morning we had a light breakfast. Cynthia cancelled her appointments for the day so we could hang out together. At breakfast she asked if I would like to do a little shopping with her, she needed a few things for her and Brian's upcoming cruise in a month. It was a beautiful day and we headed for an exclusive shopping area close to where they live. Cynthia sure honed her skill in selecting the right clothes and accessories. As she shopped she would occasionally hold something up and say "you would look just darling in this." I was now getting excited from being around and eying all of the woman's fashions. I laughingly told her to stop teasing me. She said "oh we'll just have to take care of that later." We spent a few hours shopping and had a car load of bags. It took two trips to carry all the bags up to the master bedroom. We talked as we put away the clothes in her huge closet. She literally had rows and rows of dresses, skirts, blouses and at least a hundred pairs of shoes. She said "you know I was going to bag up some of last years fashions for charity but while you're here feel welcome to take anything you want from that side," pointing to an area almost overstuffed with clothes and accessories. I said, "I wouldn't dare take these from you they are worth more than all the clothes I ever had." These were top designer labels like Prada, Dolce & Gabbana and many others. Cynthia said, "don't be ridiculous girl, take them, I'm just going to give them away." She grabbed a skirt and held it up to me. She said, "This one will look so good on you, here go try it on, I insist." After several minutes of urging, I found myself in a skirt, cashmere sweater and 4 inch heels. She said, "That looks so feminine, let's find some more." We put together several outfits, so much that she even had to give me a large suitcase to carry all my new things home. There were a couple of dresses, skirts, pants, blouses, sweaters, purses, belts and a few pairs of shoes. As we were sitting talking I heard a door slam downstairs. I panicked, since I was still wearing a pair of gray pants, a pink silk sweater and 4 inch black peep toe pumps. Cynthia told me to calm down, it's only Brian home from the office. My heart was racing as Brian stepped into the room. He looked around and quickly asked "so, what are you girls up to?" Cynthia replied, "oh I just purchased several new things and as we were putting them away Tammy here found a few old things she liked so were just seeing how she looks. What do you think?" Brian answered, "That looks great and good enough to go out for dinner." I was shocked, and responded quickly with a "no way." Cynthia grabbed my arm and smiled, "yes way, you look adorable, we'll get you fixed up and I'm not taking no for an answer." Brian said, "great, one hour ok?" Cynthia said, "this should only take a few minutes." Cynthia grabbed a cute bra and matching panties and said, "here slip these on; I have to start getting myself ready too." She also picked out and handed me a bottle of red nail polish. "You wear peep toes to show off your painted toes honey. Quick, go get them done." I rushed into the guest bath and quickly did my toe nails. Next, I slipped on the bra and panties and re-dressed in the pants and sweater. I just completed dressing when Cynthia appeared at my door. "Good your ready, follow me and we'll get some make-up and a wig on you." Brian had already dressed so we had the master bath all to ourselves. Cynthia and I then indulged in putting on our faces. She gave me a few pointers on eyes and lips that I really liked. After about twenty minutes Brian grew restless and walked in. "How long are you girls going to take? We have reservations in fifteen minutes," he exclaimed. "We're done honey," Cynthia said as she grabbed and handed me a beautiful shoulder purse. We quickly piled into Brian's Land Rover and made our way to the restaurant. I was a nervous wreck and we pulled up to the valets stand. A cute young man about 18 opened my door, offered me his hand and said, "good evening ma'am, welcome to Renaldo's." I reached out and he took my hand helping me out of the vehicle. I was now totally out in the cool night. I was in subspace, as I made my way into the restaurant entrance. I barely noticed as we made our way by dozens of couples waiting for their seating. Brian made his way to the hostess, who quickly ushered us to our waiting table. We walked by tables full of people talking, laughing, and generally enjoying their dinners. I then realized for the first time in my life I just walked by a crowd of people who were unaware of what I am, a male, wearing make-up, lipstick, mascara, a bra, panties, a pink sweater, female pants, in high heels carrying a purse. We sat down. Cynthia looked at me and asked, "first time, right?" I answered, "yes, this is very exhilarating." She leaned over smiled and secretly whispered, "so, tell me does this make you hard? I'm just curious." I was surprised by her question but thought about it briefly. I replied, "no it just feels good and so natural." She smiled and said, "girl you are more woman than you know." We enjoyed our dinner and drinks afterward. We snapped several photos, laughed and had a great time. Brian was such a gentleman and treated us girls as though we were the only one's there. The next day Cynthia and I sat and talked for hours. This time I was dressed in male mode. As we talked she probed my cross-dressing and delved deeper into my psyche. She was really interested in what turned me on as a woman. I told her it was no longer just the act of dressing that aroused me. The dressing merely relaxed me. I told her I was aroused about the thought of being a woman to a man. She asked if I ever thought about hormones. I exclaimed that up until last night no one has ever seen me dressed as a woman so there wasn't any thought of hormones. An hour after I poured out my deepest thoughts, desires and fantasies Cynthia then began to speak. She said I display all of the signs of a classic case of a secondary transsexual. I was a woman trapped in a man's body just waiting to be let out. She told me that I would definitely be much happier if I accepted myself as a woman. I sat and listened as she told me how she has studied and worked with hundreds of transsexuals. She had become very proficient at diagnosis and treatment of transgender identity. She was very sure in what she has witnessed and found in our conversations. "What I saw yesterday was very compelling. Just look at yourself, you have very feminine facial features and bone structure, soft skin, dainty hands, small feet, which are not common with men, a light voice, you have a very feminine deportment and mannerisms. You enjoy looking and dressing as a woman. You like women's fashion, home d?cor, cooking and other female activities. You have never really been into sports or athletics or any other manly activity. I know you wouldn't disagree but you definitely lack in size down there as well. You like talking about feelings, relationships and are genuinely interested in nurturing others, a female trait. You've mentioned that you would enjoy being a wife and would love taking care of a man. You would like to be pampered, loved, adored and I am sure as well be made love to." Tears welled up in my eyes as I knew she was right. She said, "see honey you know it's the right thing for you." She said, "I really think you need to start living completely as a woman. Your health and future well being depend on it. So I hope you consider making the transition. You see, Tammy I care deeply for you and this is the best advice I can give you. I want you to go back home and think seriously about it. You do not need a complete sex change since I don't feel that it would benefit you at this point, perhaps later, but you definitely need to start living as a woman." She added, "you have heard what I have to say, but only you can make the decision." After I arrived at home I was relieved that finally I had found the reasons why I was miserable as a man. I began to plan my eventual transition. A few weeks after my visit with Cynthia I started to make some progress on my transition. Per her advice I visited a local endocrinologist who gave me a prescription for female hormones. She also gave me a few tips on how to make a smooth transition. I immediately felt the effect in how relaxed it made me feel. I began to gradually change my wardrobe starting with a more androgynous look. I purchased female clothes that looked like male clothes. Flats, pants, and a male looking blouse became the normal attire for work. The fact that I was wearing female attire helped immensely. I began to slightly apply a little make-up on occasion. I was now becoming very comfortable in going out after work and weekends slightly en femme but never completely feminine looking and never a dress or skirt. Usually it was slacks or a pant suit with a low heel. Of course normal attire at home alone was a very feminine casual top, skirt or jeans, usually a high heel and of course lots of make-up. At night a pair of high heel slides, a chemise or a sexy baby doll was always worn for bed. After a couple of months of hormones my breasts gradually developed. My breasts were now starting to get sensitive and began to protrude. Not wearing a bra was becoming a problem. Luckily for me it was the time of year for sweaters and thicker clothes. I started wearing a bra full time. I also became a little bolder in increasing the amount of make-up. I added a light coat of lipstick and a light amount of mascara. My hair was now down to the bottom of my neck but I kept it neat, full and managed. My nails were always long and well manicured. I used a coat of clear gloss polish for my fingers and a coat of red or dark color for my toes. After time my skin softened and most of my male fat disappeared. I worked out weekly so I felt good about my body. As spring neared I again took stock of my situation. I was able to conceal my breasts with thicker clothes but as the weather got warmer I had to think about my next move. I was still dressing androgynously but had really pushed towards the side of looking more like a woman. Pierced ears, more make-up, higher heels and a small purse were now more common. Also, during this time my correspondence with men went >from internet chats to phone calls and eventually some video monitoring. Everyone I met welcomed my coming out completely including Cynthia and Brian. I was still nervous about taking that final step. Finally, in late March I couldn't resist any longer. I had to make a decision. My biggest hurdle was my job. I had moved up the ranks over the years and was well respected and liked. I made good money, lived comfortably and enjoyed my work. I risked everything if I came out at work and wasn't accepted. I approached a gal in human resources I've know for years. I explained to her that I had a personal issue that has been bothered me for many years. I began to explain my desire to come out of the closet. She stopped me cold saying, "honey, we've know about you for over a year." She added, "it was pretty obvious when you started wearing those clothes and the make-up last year. We just were waiting for the day you revealed yourself." She went on to explain that the company was an equal opportunity employer and very liberal minded. A few satellite offices already had transsexual employees. Several years ago company representatives attended seminars related to the acceptance of transgender employees. She looked at me and said, "darling welcome to our club. I'll make the proper changes to your personnel file." She asked me, "so what can we call you now?" "My name is Tamara or just Tammy," I replied. I was completely overwhelmed with emotion. I cried as I left her office. At work that night, just before I left, I received a company wide email. It was posted to all employees. It was a memo announcing my change in gender and for everyone to please welcome the new Tammy. The memo went on to re-iterate the company's policy towards the acceptance of transgender employees. The next day I dressed just like I have been because I was uncertain to the company reaction. Little by little people would stop by my office to offer their congratulations and support. At one point several girls gathered in my office and we chatted about my transition. They laughed and said there was a small pool going around betting on the month I would come out. They also offered to include me in their lunches from now on. I told them, "the first lunch is on me," in which they all broke out laughing saying that men should come out more often. As the days went on, little by little I began to dress more feminine. I didn't want to rush it. Besides, I still didn't have enough clothes for work yet. I slowly began to build my wardrobe and wear more feminine clothes. I completely discarded my male wardrobe months ago. I now started wearing higher heels, mostly pumps and sling backs but occasionally I wore sandals if the weather was nice. I started to show more color in my outfits especially my tops. My hair was now shoulder length and after my coming out, I had a very feminine cut. I now wore a moderate amount of make-up and really spiced up my look with pretty necklaces and earrings. Soon I began wearing skirts and occasionally a dress. I now felt confident and was completely comfortable. My career really took off. I was quickly promoted and rose to an assistant vice president. I had a window office, on a lower floor. It was a big boost for my new female ego. My contemporary office was feminized as well with soft colors, flowers, scented candles and pretty figurines. After a couple of months from coming out, the men in my office were still reluctant to approach me. I remained cordial to a few, but it wasn't the same as in the past. I think they were afraid of what others would think if they associated with me. However, the ones I had normal business contact with treated me with compassion and respect, which I greatly appreciated. The women really opened up and I became good friends with several girls. I pretty much continued to correspond with my internet buddies. By now they were completely taken with me as I became more of a woman. I had many propositions and a few proposals but nothing really attracted my interest yet. As I transitioned further, the quality level of the men improved proportionally. These men were more professional, good looking, successful and confident. All of which were traits that I found attractive in a man. I found that there is a large following of men that are attracted to transsexuals. I was attracted to one particular guy named Rick. He really poured on the charm. We spoke on the phone many nights. He became a good friend but something about him really attracted me. He had everything I found appealing in a man. Best of all he was local to me. Finally, after many weeks of persistence of asking me on a date, I accepted. Due to our hectic schedules, we decided to meet for drinks at a hotel on a weeknight. This was a very upscale hotel that had a posh lounge. The place had a mostly business clientele. The afternoon of our date, I decided to leave work a few hours earlier to get ready. It was nerve racking selecting the right outfit to wear. I didn't want to wear something too sexy. I just want to wear an outfit that looked more casual but dressy. I considered wearing a skirt but decided on a nice pair of white slacks instead. I chose a really feminine sleeveless top that had a lot of different colors. Next, I selected a new pair of green snakeskin sling back sandals with a 4 inch stacked heel. They were really tall but I remember Rick saying he was about 6 feet 3 inches tall. After I laid out my outfit I took a long hot bath. I just love taking a long bath. It relaxes me from the daily grind. I usually light several scented candles, turn on some soft music, turn down the lights and pour myself a glass of red wine. I'll just lay in the tub for a long time relaxing. This time I applied an avocado facial mask and even had cut a couple of cucumber rounds for my eyes. It helps reduce puffiness. After I soaked for a while I had to shave my legs and then wash my hair. After a bath I like to slip on a heavy terry bathrobe, wrap my hair up in a big towel and a turn up all the lights. I then sat down and did my nails. Since I already had a French manicure applied to my fingers at a salon, I only did my toes in a deep red. I then moisturized my body with a very sexy lotion I like. I just love Victoria Secret's Breathless collection. I'll then start to get my hair dried which takes several minutes. After my hair, I'll put on my bra, panties, pants and top. I then began to apply my make-up. Since I had plenty of time to get ready I really laid on the make-up. This is a girl's playtime so I had to be careful to not overdo it. After the make-up I styled my hair a bit. Next, I slipped on my heels. I just love the way my painted toes look peeking out the front of my shoes. I was a pretty contrast to the white pants and green sandals. I then found a darling pair of colorful dangle earrings with a matching necklace. After a quick spray of cologne and a check in the mirror I grabbed my white patent leather shoulder purse and headed for the door. I felt very feminine as I made my way to my car. Once in the car my cell phone rang. It was Rick. He just walked into the lounge and asked how I was doing. I said, "Just give me a few minutes," as I was on my way there. I pulled into the parking garage and with luck found a spot across from the side entrance. A quick coat of lip stick and I was heading for the door of the hotel lobby. Heads were turning from everywhere as I walked through the lobby. I know from experience that the click-clack sound of high heels on marble flooring will draw the attention from every man in the room. Alas, I recognized Rick from his pictures. He is tall, handsome and was very neatly dressed. He was all smiles as our eyes met. He quickly headed towards me and me towards him. We embraced with a big hug. I knew he was tall but I still had to stand on my tip toes even in heels. I broke the silence saying, "it is so nice to finally meet." He said, "likewise, and may I say you look absolutely adorable." I blushed without a comment as we made our way to a waiting table in the lounge. It was more of a booth seat with a small table. I sat down close next to Rick facing him and quickly crossed my legs. He then said, "I really love your outfit and especially your shoes." I replied, "thank you so much, that is so sweet of you," as I held up my right shoe admiring my foot. A waitress then stopped at our table to take our order for drinks. Rick ordered a scotch and I ordered a glass of white wine. We sat and had drinks for a long time. We laughed and talked about dozens of topics and I found that we both had similar likes. I told him all about my transition to a woman and he talked all about his recent divorce. He explained why he became attracted to transsexuals. He is looking for a woman, who appreciates being a woman and one who knows how to use it in a relationship to please her man. What really attracted me to Rick was his sense of humor. I just love his little jokes and comments and he never lets you forget how important and desirable you are. As the night wound down and the lounge gradually emptied we found ourselves looking into each others eyes. We looked at each other and smiled for a long time. My heart was pounding as I knew what he wanted. I wanted it too. He leaned in close to my face. I closed my eyes as our lips lightly touched. We held a kiss for several seconds. The kiss broke and I just melted. He quickly repeated it with a second. This time it was longer and I really felt the firmness of his lips. They felt manly which made me feel warm and secure. He scooted closer to me and was gently rubbing the top of my thigh. I sat content with my hands in my lap. We kissed and broke several times over the next few minutes. It felt like it was happening all night. I briefly wished he would slip his tongue into my mouth but quickly thought why rush it. After a few minutes later we gathered our composure together. Otherwise we would have continued making out all night. Now I knew why woman like kissing so much. There are many thoughts that go through your mind in this act such as warmth, closeness and sweet surrender. I broke the silence saying, "I would love to continue this longer but It's getting late and " He quickly interrupted saying, "no need to say anything else I understand." We both stood up, I grabbed my purse and headed for the hotel lobby. Rick had his arm around me and I felt special as we walked together. "Can I walk you to your car?" he asked. "That would be great," I replied. We headed into the parking garage and over to my car. I opened my purse and found the remote door lock and clicked it. He opened my door and I stopped and looked up into his eyes. He leaned down and I lifted and wrapped my arms around his neck. We kissed and looked at each other for a minute. He broke the silence. "Can I call you tomorrow?" he asked. I replied, "I can't wait," and sat in the driver's seat and pulled my heels into the car. He closed the door and backed away. I started the car and began to back out of the space. We waved at each other as I slowly drove away. I didn't remember the drive home but when I got there I was breathless as I fell into my bed reminiscing about my first date and kiss. The next day I woke and was giddy with excitement. It was a beautiful day and I couldn't wait to get into the office. I wore a pretty halter top, silk skirt and a pair of brown t-strap high heel sandals. I felt great all morning and everything seem to flow with ease at the office. About mid-morning, after a meeting, I received a large vase full of pretty flowers and everyone gathered in my office as I opened the card. "Read it, read it," everyone urged. I opened the card and briefly read it to myself. It read, "hope you enjoyed yourself last night as much as I, Love Rick." The group let out a simultaneous cry of "Oh la la." I had to explain who Rick was and all about our date. A while later, after things calmed down, Rick called and asked how I liked my surprise. I said, "oh I just love the flowers and yes I did enjoy myself last night." He said, "great would you like to have dinner this Saturday night?" "Oh, I would love to," I replied. He added that the restaurant he had in mind is an elegant place so plan to wear something dressy. I asked, "so does than mean little black dress?" He said, "I can't wait to see you in it, I'll pick you up at seven." After we hung up I reflected to myself. This is what I like about being a woman. Having a date on Saturday night, all dressed up with somewhere to go, someone to share it with and having fun. "Oh no, I haven't a black dress," I thought. "No fear honey, you have a few days and you love to shop," I said to myself. The next few days I shopped and tried on many dresses. I finally found a cute sleeveless black dress that was simple but elegant. This dress made me look thin and I loved the way it fit. It was loose and comfortable but looked like it followed all of my curves. The length was slightly above my knee. I had lost a few inches recently and now weighed about 120 pounds. Having lost a few pounds off my belly was redistributed to my breasts which were now about a "C" cup. As I shopped, I also found a pair of black patent high heel sandals. When Saturday arrived I cleaned house a little in the morning but decided to relax that afternoon. After a short nap I decided it's time to start getting ready. I took my usual long hot soothing bath which I just absolutely love. I almost drifted off to sleep in the tub until I caught myself thinking about Rick. I tweaked my nipples as I dreamed. It was a weird feeling of contentment and excitement at the same time coupled with a few hot flashes. I couldn't get an erection anymore, due to the hormones, but I could swear it felt like I was having an orgasm. My focus was no longer on my penis, it didn't work, but more on my feelings. I wanted more of this new found feeling. I gathered my senses and got out of the tub. I felt fresh as I proceeded to get myself ready. After drying my hair and moisturizing I got into my black lace panties and bra. I then applied my make-up. As usual I played and made sure I had just the right candlelight make- up look. After putting on my face I slipped the dress over my head and it fell gracefully into place. I reached back and pulled up the rear zipper. Next, I opened the box housing my new shoes and removed them from their protective dust bag. I sat on the edge of my bed as I slipped into the sandals and fastened the ankle straps. They were so tall and I just towered as I stood up. I walked over to my dresser and opened my jewelry box. I searched for my faux diamond necklace and matching earrings. I slightly tilted my head to each side as I fastened the back of the earring to the posts. I applied a light amount of perfume behind each ear and down the front of my chest from my neck towards the cleavage of my breasts. I transferred the things >from my day purse to my evening clutch. After a touch up of lipstick I was ready. I took a breather as I sat and waited for Rick to arrive. I worried he might have trouble finding my apartment but he arrived on time. The door bell rang and I quickly hurried to the door. I peeked through the peep hole and saw him standing there. I opened the door slowly and smiled as our faces met. He looked simply gorgeous in his suit and tie. He stepped in with a serious look as he scanned my body head to toe. I held my smile and turned about 180 degrees saying, "So how do I look?" He smiled and said, "Darling you look ravishing." "Great, let's go," I said as I grabbed his arm stepping through the doorway. I locked the door behind me and we headed for his car. The night was warm but a cool breeze found my legs as we walked. There was silence except for the click clack of high heels echoing through the court yard as we walked my two steps to his one. He held my waist as we walked. Not knowing which car was his he guided me towards a stunning black BMW 760 sedan. He opened the door and held my hand as I elegantly sat down. He waited and gazed on my legs as I slowly swung my heels into the passenger side. The door closed and he quickly hurried in. As we rode to the restaurant we chatted while listening to a light jazz CD. We arrived and pulled up to the valet. We got out and made our way in. This place was full of high class people as we found our table in a quiet corner. He faced me and I faced the crowd of tables around us. We dined, laughed and had a great time. Again, he was an absolute prince and I felt like I was a princess. After a seven course meal I was full. I tried to not overeat but the food was just fantastic and the service was superb. After he took care of the check we headed to the piano bar adjacent to the restaurant. We found an open seat close to the piano player. We talked for awhile and Rick made a request for the piano player. When Rick's request started playing he stood up and offered his hand. "Let's dance darling," he said. I rose to my feet and he led us to the dance floor. I didn't know how to dance very well, especially in heels, but Rick was a great lead and he made me look like I was an expert on the dance floor. We danced for several songs when a slow song began to play. I reached up and wrapped my arms around his neck and I felt our bodies pushing back against each other. As the song progressed I felt firmness pushing back against my stomach I looked up and he smiled. I titled my head up further and he leaned down and kissed me. As we danced we kissed on and off. After several minutes I was getting warm even though we were slowly dancing. I knew he wanted me and I felt content and safe. He made me feel so sexy. I was in a daze as we headed to his house. Sometime in the last thirty minutes he offered to go back to his place and I accepted. We entered a gated community and pulled up to a large house. We circled the long drive up to the main entrance. He parked, walked around to my side of the car and opened the door. He took my hand, helped me out and led me up a set of stairs leading to the main door. The house was quiet as we entered. Lights automatically lit as we headed up a staircase. We walked a long hall way and I noticed all the furnishings were very elegant. We continued through a set of double doors. Dimly lit ceiling lights lit as we entered a large bedroom suite. As we made our way into the room I was amazed at its size and decor. Rick closed the double doors behind him. He casually walked up to me and we kissed. I then broke the silence asking him if I could use the bathroom. He said, "absolutely by all means," and pointed to a door. I walked in and a set of lights immediately lit up the room. I approached the huge vanity and looked at the mirror. I wanted to make sure my make-up was fresh and everything appeared to be in order. It was. I walked through the door back into the bedroom. Rick was standing at the foot of the bed holding his hand out. I walked toward him and he gently grabbed me pulling my body to his. We kissed. I looked up to him and I was still in a slight daze. I spoke; "I can't wait to make love," were the words out of my mouth. He smiled and gently turned me around. He slowly unzipped my dress and then turned me back. His hands moved up to drop my dress. It fell to the floor. I stepped out of the pile at my feet. I then reached up and began to untie his tie and unbutton his shirt. As his shirt opened I could see a hairy chest. I ran my long nails through his chest hairs as I took in his manly cologne. He reached behind and grabbed my hips pulling them into his. We continued to kiss. I heard him slip out of his shoes. I lowered myself to the floor to help him remove his socks. I was on the floor in front of him. I proceeded to unbuckle his belt and unzip his pants. It was a bit awkward, due to my long nails, but his pants dropped to the floor. He stepped out of the pants and stood there as I glanced up to him. He had an obvious erection tenting his boxers. I slid my fingers through the waistband and slowly slid them down. Inch by inch I saw his erection emerge in sight. As I slid the waistband over his erection it sprang abruptly up. It was big, straight as an arrow and pointing slightly up. Probably the biggest cock I have seen. It was definitely at least eight inches long and very thick. I could now smell his musky scent. I looked at the cock and placed my hands on the front of his upper legs framing his cock. I slowly inched my hands towards my prize reaching his well trimmed pubic hair. My hands found the base of his cock and slowly opened to hold it. I grabbed my prize, first one hand then the other. I slowly stoked it as he closed his eyes. I continued to softly stoke it with one hand. It was soft and hard as a rock. I stroked it for a minute or two and then licked my lips and moved closer. The head practically hit my nose as I moved closer. I opened my mouth slightly as the tip reached my lips. My painted lips parted as I pushed them down on it. The head entered my mouth and I proceeded to insert his cock further in my mouth. It felt like a large cucumber filling my mouth as I slowly withdrew from it. Then just as quick as I withdrew it I plunged back down on it. Within a second or two I was bobbing up and down slowly on it. I looked at his cock and could see a distinctive lipstick ring around it. I felt a rush of pride. I wanted to please him with my mouth so bad now. Over the next minute or two I progressed quicker and quicker and I felt his hands on the side of my head. He said "slow down baby." I stopped abruptly and looked up afraid I was doing something wrong. He said, "You're a good little cocksucker honey." I smiled and stood up. He quickly grabbed me and we fell onto the king sized bed together. We moved up toward the pillows and he laid me down on my back. He laid close to me on his side and held me firmly. We kissed passionately and I felt him caressing my body. He moved his hands towards my breast and began to feel me up. He slid the lace edge of my bra back exposing my nipple and proceeded to tweak it with his tongue. The feeling was fantastic and I was forced to arch my back in ecstasy. I sat up and he unfastened and then removed my bra. He now had a full access to indulge on my nipples. He got back to my nipples in quick time going back and forth from one to the other. As he did this, I slid off my panties. I was almost unaware I still had on my heels. He helped me remove my panties throwing them across the bed on the floor. As all of this was going on I continued to rub and stroke his cock. He was excited and I was excited. After this teasing, groping and stroking for several minutes he sat up to reach for a tube of lubricant on his night stand. He sat up next to me on his knees and applied a generous amount to the shaft of his cock. I help him rub it around. He then spread my legs apart and got between them. I felt helpless as he climbed over me. I lay on my back, pulled my legs up and lifted my ass. He had full access to my ass now. I felt so vulnerable in this position. He slowly moved in for the insertion. I felt the tip probe my opening. I looked up scared and said, "please be gentle." He smile and said, "let me know if you feel any discomfort." I then felt him slowly begin his penetration. It was like crapping only in reverse and out of my control. The tip made its way in and I felt some pain. I bared the pain because I didn't want him to stop. Slowly the tip went in. He used little strokes of pressure to slowly insert it deeper and deeper. It went in and in. I felt the shaft on the walls of my ass. The thickness felt like my ass hole would rip open. When he reached the end of the insertion he paused and slowly withdrew it. He withdrew as long as it took to insert. When I felt the tip emerge it was a feeling of emptiness. He pushed in again only a little quicker this time. Within a few moments he was slowly pumping in and out. My legs relaxed enough to clamp onto his legs just below his ass. I was careful not to poke him with my heels. My nervousness began to subside. He relaxed on top of me and continued to slowly pump. I felt close to him and overwhelmed with emotion. He looked down at me briefly and quickly put his cheek next to mine. He turned and we kissed deeply. He was pumping me good now and the pain was turning to pleasure. I couldn't believe it. I was getting fucked by a man. I began to meet his stokes with my own and we soon developed a rhythm. I wasn't timing this but I swear it was going on at least twenty minutes. He would stop, pause and then begin again. I realized he was teasing me and I shot back with a "fuck me baby, don't stop." We continued almost to the point of my ass getting sloppy. Here and there I would feel a warm shivering rush pulse through my body. It was like a content closeness with my lover. It was a full relaxation and tensing all in one. Later I realized I was having small girlie orgasms. I pulled his ass in with my hands digging my nails in his skin. He said he was close to orgasm. I told him to let it go. He continued pumping hard and fast. Then he stopped and paused. I could feel him pulse inside of me. He was shooting his load inside me. It was a great feeling. I was just thoroughly fucked like a woman and it felt wonderful. There was semen all over me and the bed. I didn't care as I lay in the wetness. After and hour more of kissing and lovemaking we fell asleep exhausted. My ass felt like it was inside out. The next morning we woke together. He asked if my ass was sore and I told him I hurt but not too bad. We slipped on matching white robes and headed to the kitchen. Rick wanted to make me breakfast. He then gave me a tour of his house and estate. Yes, it was a huge property. He said he really enjoyed our time together and he would like to continue seeing me. He said, "let's just take this slow and see where it leads to." I agreed, but I secretly planned on being the lady of this house in the very near future. We repeated our dates and lovemaking scenarios many times over the next several months. We would stay sometimes at his place and sometimes at my place. He surprised me a few times at my office. One night I was working late and for some reason was really horny. Rick showed up with candles, a bottle of wine and takeout. We fucked on the couch in my office. We became a real couple. There was a never ending stream of dinner and office parties, weddings, vacationing and social gatherings. We were very much in love and I loved being his woman.