The Business Trip Part III: Tanya's Story free porn video

The following story is a work of fiction. It contains sexual themes and descriptions. It includes Transgender themes and depictions of Bondage, Domination and Submission. It is meant purely for entertainment and no endorsement or condemnation of the subjects is implied or intended. IF YOU ARE BOTHERED, REPULSED OR OTHERWISE OFFENDED BY THIS SUBJECT MATTER DO NOT READ THIS STORY. The Business Trip III: Tanya's Story By Bootlover Tanya and I had agreed to meet for dinner. As much as last night had been a first for both of us tonight would really be breaking new ground. We weren't going back to the club. We were going out to dinner at a restaurant downtown. We both fervently hoped that San Francisco was as tolerant as it's reputation where acceptance of alternative lifestyles was concerned. Instead of the relative safety of the club where everyone in attendance had their own slant on life we were venturing out into the community at large. On a real date, for dinner. I dressed in a pair of khaki pants, loafers a button down shirt and a blue blazer. I hopped into the rental and sped up to San Fran. I arrived at Tanya's condo and buzzed her on the intercom. "I'll be right down." she said. She must have flown because she appeared on the stairs and toward the door in a flash. I was really stunned by her appearance. She was wearing a very nice black dress that showed some cleavage but nothing racy. The hemline was cut below mid thigh showing enough of her beautiful legs but nothing like the mini skirt and mini dress of the previous two nights. She wore a pair of (I later learned) Anne Klein II pumps, black with a 3" fashion heel. What really set her apart though was her hair and make up. Her hair was up in a French braid and looked lustrous. She wore beautiful pearl earrings and a pearl necklace. Her makeup was perfect. Lightly shadowed eyes, highlighted cheeks and muted lipstick. Even her eyes had changed, with no contacts in they were a light shade of brown. In the most complimentary way all I could say was she looked like a beautiful soccer mom dressed in Anne Taylor fashions in town to meet her husband for dinner. "You look beautiful," I said, hoping the simple, direct statement of the truth was enough to let her know how good she looked. I escorted her down the stairs and held the car door for her. When I ran around and got in the other side her sweet perfume was lightly filling the air. Her dress rode up just a little, exposing a few precious inches more of her thighs. "I really mean it," I said, "you look beautiful." "Thank you," she said and I thought there was a bit of a blush on her face. We held hands most of the way to the restaurant and parked the car. We walked up the street hand in hand not talking just being together. As we approached the restaurant other people looked our way. Most glances were quick, though a few men and one woman took long looks drinking in Tanya as she walked by. Most of the looks appeared lustful, if anything, to me, not judgmental. Inside we were seated at a booth in the back by happenstance. When I made the reservation I had not asked for anything special. I wanted tonight to unfold on it's own. We were seated, ordered a drink and looked over the menu. We ordered when the drinks arrived, sitting side by side in the booth. "Tell me your story," I said, looking into her eyes. "I had two older sisters;" she began, "who were five and a half and four years older than me. Growing up my sisters did not play with me all that much since they were considerably older. Usually the only time we played together was when we were stuck in the house on a rainy day. The game we played most often was dress up, and I was dressed up in women's clothes just like my sisters. I never really minded or put up any fight." We continued on as a normal family with usually sibling squabbles and happy memories of vacations and birthday parties. One day stands out though. I was nine and my older sister was turning 15. Over the course of a few months she had developed breasts and they had really become noticeable of late. My younger sister had the beginnings of breasts but Jenna really had them. My mother was pretty busty and it looked like my older sister got her genes. One afternoon I was alone in the house. I snuck into my sister's room and open her drawer. I pulled out a bra, a Playtex 34C, I still remember it. White, no design and under wired. I stripped to my tighty whities and put the bra on, I couldn't resist. I stuffed a few socks in it and was looking at it in the mirror when Jenna and her friend walked in! Her friend started to laugh as I tried like crazy to pull off the bra. 'Don't rip it!' Jenna yelled and I stopped. Jenna spoke to her friend and made her stop laughing. Then she turned to me. 'It's okay; if you want to try on some of my things we'll help you.' I tried to run but Jenna shut the door and her friend grabbed me by the wrist. Her nails dug into me, leaving marks in my skin. They stripped my underwear off and put on a pair of Carol's, my other sister. Then they stuffed a few more socks in the bra, and then they put me in a dress with knee sox and a pair of Carol's shoes with a 2 inch heel. Then came the make up. They used all the stuff they had. Jenna told me to sit still or she'd tell mom and dad. I looked in the mirror when they were done and, well, I looked like I was one of Jenna's friends. Except for my haircut I looked very femme. They didn't tease me, though I'm sure they laughed about it later. I wore the make up and the clothes for the rest of the afternoon. They stripped me and left me to wash off the make up and get back into my boy clothes when they heard my mom's car in the driveway. After that they would dress me up from time to time. Jenna even gave me an old pair of her panties to wear and I wore them to bed under my pajamas. As I grew I began to sneak my sisters' clothes and then my mother's to wear. My mother had a leather skirt that I wore every chance I could. My mom was not big and I could only fit in her shoes for a short time, until I was 11 or so. I got to wear her heels some but she never had any sexy boots. Eventually I out grew mom's size and had to rely on Jenna and Carol's clothes. My feet were too big for their shoes though. When Jenna was 18 she was beautiful. She was a blonde, blue-eyed cheerleader with a fabulous body. She was heading off to college in the fall and would be away until Christmas. Two days before she left she said, "Come on a ride with me." and we got in mom's car. She drove to the mall and we went to J C Penny. She made me follow her as she shopped. She picked out 2 new pairs of panties for me, she even asked which ones I liked, she picked out a camisole and then we went to the shoe department. She bought me a pair of knee-high zip up boots with 3" stacked heels. At this point I was jerking off furiously, twice a day at least and as many seven or eight times a day. My sisters took to calling me "Squirt", which everyone thought was reference to my being their little brother but it was because they knew what I was doing. I was so hard riding home in the car I couldn't wait to go put on the boots and jerk off. Jenna took me up to her room when we got home, she watched me change in to the panties, though I turned my back to her so she wouldn't see my erection. Then she told me to sit on the bed. She took some nail polish and painted my toes. While they were drying she applied makeup to my face. When they were dry she watched me put on the boots. I stood in front of the mirror in my new boots and fresh makeup. At 13 I had a very slight build though I was pretty tall. Jenna stood beside me and said, 'If you had tits you'd look pretty much like a girl. Well, except for this.' She reached down and touched the head of my penis, which was sticking up over the band of the panties. I jerked away but Jenna said not to worry and lead me over to her bed. She had me lay down and she began caress me through the panties. Eventually she slipped her hand inside and stroked me until I came. I looked and her and she just said, 'The cheerleading squad jerks off the football players all the time. It's easier and better than the alternatives. You better get cleaned up and hide your new things, I hear mom in the driveway.' She left for college two days later and gave me a huge hug and kiss. I cried that night because I knew I would miss her. I wrote her a note thanking her for the panties and boots, telling her I wore the panties every night and the boots whenever I could. She came home at Christmas but her schedule was too hectic for anything to happen. Carol was not really interested at all and she was too small for me to really wear her clothes. Jenna returned in May at the end of her first year in college. I hugged her a long time and then we chatted all night. It was as if we were sisters and she told me a lot about her first year. Late that night she had me dress for her. I had grown so much that I couldn't fit in the boots any more, I apologized to her but she said it was no big deal. I couldn't fit too well in her clothes anymore either. So she had me wear my panties, painted my toes and made up my face. She then stroked me until I came. I went back to my room and fell asleep in my panties. One day over the summer Jenna's boyfriend from college showed up. He lived a ways away and he drove to visit her for a few days. I came home that afternoon and found Jenna in her bedroom with him. She was naked and on all fours on her bed. He was kneeling behind her and fucking her very hard. Her face was all screwed up and red and she was breathing in gasps. Her hands had clutched the bedcovers into knots. I stood in the doorway, my mouth wide open, a fourteen year old boy watching his nineteen year old sister get fucked. I thought she was in pain but she smiled at me and then began to orgasm. She put her head down and moaned into the bed, muffling her sounds. She came for what seemed like a long time, but how would I know. Shortly thereafter her boyfriend began to grunt and then he threw his head back and pulled her by the hips tight onto him. Then they fell to the bed laughing and tickling each other. A little while later she came into my room. 'Please don't tell anyone about this. Chuck and I are being careful but mom and dad wood freak.' A day later Chuck left. That night Jenna and I had a long talk about sex and what she had discovered. I told her I thought he was hurting her and she laughed. 'It feels really good.' she said. She turned off the lights so that only the moonlight from the window filled the room. She showed me how she masturbated and I saw her face screw up in the moonlight, then her body shudder and then her release. I was shocked and amazed. She began to stroke me, working me very slowly. As she did she worked her finger into my rear. I came so hard I think I shot across the room. By the end of the summer I was really tan and my hair was quite long, to my shoulders. Jenna wanted to have some fun and she asked me to go to the beach with her. The night before she called me to her room. While there she showed me her new bikini she planned on wearing the next day. Then she held up her old one. 'Want to wear this one?' she asked me. I was stunned. 'How can I wear that' I asked. She put it on me but my erection was a dead give away. And I had no breasts. Still I liked how it looked and Jenna even said I had a girl's ass and hips. Jenna gave me a pair of her cut off shorts. The material was heavy enough to hide my erection but they were short enough to show my ass cheeks. She painted my toes and in the morning she made up my face a little and blew dry my hair so it had some style. We went to the beach and no guy noticed me because they were too busy checking out Jenna in her bikini. By now my sister was about a 38D. My flat chested top drew no attention. We spent the day at the beach laughing and talking like girlfriends. Fortunately for me I had enough tan already so no new tan lines appeared. A few weeks later Jen was ready to head back to college. She bought me some new panties from Victoria's Secret, where she was now buying hers. That night in her room she brought me off. I started crying because she was leaving and she cradled me in her arms like a baby, rocking me back and forth. Some how I started sucking at her breast and it was as if she were breastfeeding me. She had opened her shirt and offered me her nipple to stop my whimpering. I felt so good I her arms, so loved and so warm. I fell asleep sucking on her. Later she led me to bed. We talked on the phone a lot that year while she was away. Even more than she and Carol did. Carol had a wild group of friends, was always out or grounded. She was heading to college in a year and everyone was afraid of what might happen. I couldn't wait for Jenna to come home in May. I was 15 and I reacted to her return like a girl instead of a guy. I hugged and kissed her as soon as I saw her. She whispered in my ear, 'I have a cool new surprise for you!' That night she was out with friends and came home late. I waited up for her and snuck into her room. We talked and talked and then she jumped up. 'I almost forgot your surprise!' She rummaged through one of her bags and then presented me with a pair of 4" black spike heel pumps. They were used and scuffed but they were big, even a little big for my foot. I took off my pants, revealing my panties, and stepped into the heels. My ankles wobbled a little a first but then I was fine. I walked around the room a bit and I liked the feel of the heel hitting first and then the sole. 'Geez, those make your ass look great.' Jenna giggled and she grabbed my ass and gave it a squeeze. 'I got a surprise for me too.' she said. I watched as she pulled a vibrator from under her pillow. It was plastic and cream color and about 7 inches long. 'Wow!' was all I could say. 'What is it?' 'It's a vibrator.' Jenna replied. 'What does it do?' I asked. 'Watch.' she replied with a big grin. She lay back on her bed and turned the vibe on. She ran it over her breasts and around her nipples, then down her stomach to her crotch and thighs. She began concentrating it on her crotch and began to run it up and down over her panties. In no time she was breathing heavy and then orgasmed right there in front of me. After she rested for a minute she pulled me onto the bed she showed me how the speed was adjustable and then she ran it over my nipples. It was as if an electric shock went through me. My nipples got hard, as did other things, right away. She moved the vibe to my crotch and it felt wonderful. I remember thinking at that moment, as I lay there in my Victoria's Secret panties and 4" black pumps with a vibrator stimulating my crotch, this is how a girl feels, I'm just like Jenna. I started playing with myself and my sister used the vibe on my nips. I came quickly and very hard. A fabulous orgasm. A few days later, I was alone in the house. I had cleaned up and shined my pumps so that they looked pretty good. I snuck into my sister's room and found the toy hidden at the back of her lingerie drawer. I pulled it out and looked it over closely. It was totally smooth and shaped like a bullet. I turned it on and ran it over my nipples. Again it was like electricity going through me. I rubbed it all over my body; I mean everywhere, discovering where it felt best. I found that the biggest thrill was when it touched my bum hole. I knew, I just knew that it could feel even better. I pressed the nose against the hole. The feeling was tremendous but I wanted more. I used some of Jen's face cream on the tip of the plastic and put it at my hole again and slipped it in. It hurt a bit as I stretched but it also felt really, really good. I took about 2 or 3 inches in me before I came. Without even touching myself I came! I opened my eyes and there was Jenna standing there watching me. I didn't know what to say. She just said, 'We'll talk about this tonight. Clean up and get out!' I thought she was pissed. That night I went to her room. We talked for a while. She told me she was mad that I had gone through her stuff. She said she thought that I would have talked to her first, asked for her permission and help. In the end she said she understood. Then she asked if she could help. Of course I said yes. In no time at all she had me laying face down on the bed, legs spread as she lubed the vibe and my hole with oil. She slid it in slowly and easily letting me get used to it. Then she turned it on, and then she started fucking me with it! I couldn't believe how good it felt. When she pushed it in deep I came. We talked a lot that night afterward. She asked if I had a girlfriend, which was no, asked if I had kissed a girl, which was also no. We talked about a lot of things but basically she was asking me if I was gay. I was 15, confused and inexperienced. I didn't hang out with the guys much. I wanted to hang out with the girls but, of course, they weren't interested in me. I ran cross country, was on the swim team but wasn't very good and had tried tennis but only was a practice player, never good enough to be in a match. I told her how much I liked being with her. How she was the only person who was really nice to me and how I missed her when she was gone. She looked at me and said softly, 'You know, it's funny, you're more of a sister to me than Carol.' I almost had tears in my eyes when I looked at her and said, 'I wish I were your sister for real.' The flood gates had opened. We talked all night but I had finally admitted to her, and perhaps for the first time to myself, that I wished I were a female. I wasn't gay because to me that meant I wanted to be with another guy as a guy. That isn't what I wanted. For the rest of that summer Jenna did everything she could to make me feel like a girl. We bought a mastectomy swimsuit so I could go to the beach with her, she taught me how to select and put on my own makeup and we went shopping together. She even helped me change in the car before we went into the mall so I could try things on in the women's dressing rooms. My long hair and makeup helped me pass quite well and though a few people and sales clerk looked me over pretty good most people never even gave me a second look. We bought my own vibe; we bought more shoes, lingerie and a few outfits. My father was a surgeon and he was always at the hospital, or playing golf at his clubs when he wasn't at work. He was rarely home. My mom was an attorney and as we got older she was around less and less because of her work. By the time I was 10 she was back at work full time and by the time I was 15 she was working almost as much as my father. They just left money around for us to buy food, get gas and all that stuff. I spent a lot of time by myself. Carol was off doing what ever she did, drugs I think. When Jenna left for college in the fall we talked again. I cried again. Carol had left for her freshman year a few days earlier and I didn't even care. I was a sophomore in high school and basically alone. Jenna and I talked about once a week on the phone and that kept me sane. She didn't come home that summer because she had an internship with a professor. I had gotten my license and she suggested to mom and dad that I come to visit her for a weekend. Dad had bought me my own car for the summer and said, 'Sure, why not.' Jenna was at Columbia in New York. I drove most of the way and then took the train into the city. She met me at Grand Central and then we rode the subway to her apartment. On the way she proposed some thing to me. I would be Carol! She would introduce me to every one as Carol and I could spend the whole weekend as a woman. I was thrilled. We bought a few things to round out my wardrobe options and spent the weekend shopping, going to a musical and seeing museums all the while I was en femme. I loved it. She even took me to a salon in the village where they did my hair, my nails and me toes. I bought a pair of strappy high heels to wear out on Saturday night and I must admit that with the hair, makeup, long nails and heels I looked like a woman. I bought some breast forms to fill out a bra and that one illusion made my body look feminine. I was tall and thin, my waist narrow with small hips and a small, tight ass. I looked like a model actually. Only my voice, which wasn't deep but wasn't very feminine, threatened to reveal my true self. Jenna never came home to stay again. She stayed in the city full time and just visited us. I went down to see her as "Carol" 3 or four times a year. When it came time for college I went out to UCLA. I wanted a big school where I wouldn't be well known. I lived off campus from my second semester on. I went to classes as a male but spent almost all of the rest of my time in female attire. I met a professor in a psychology class and started talking to him. I became his patient and we began to work on my situation. Eventually we agreed that a transition was the right course. I began just after graduation. I started hormone therapy and laid out a course of surgical procedures. I went home after I started and with Jenna by my side told my parents everything. To put the best light on it, the reception was cool. My father was stone faced and said nothing. My mother was confused and kept asking me why. I don't speak with my father anymore and I don't go home. Carol wasn't there but I haven't spoken to her in several years. My mother has accepted my transition and she comes to visit me every year at Christmas. Jenna remains my best friend and we see each other several times a year. She's married to a nice guy and has two children. The kids are young and have only known me as Aunt Tina. I'm sorry but my real name is Christina and I go by Tina. When we first met I really never expected us to have more than a quick interlude together so I introduced myself as Tanya. Tanya is my club name, sort of a game I play with myself. Tanya dresses wilder and goes to clubs. Tina is who I am and I dress like this. I work for an insurance company here in San Francisco; I'm in charge of the Marketing Department. It's been a tough last five years. Hormone therapy was an initial thrill. Three good things happened rather quickly. First, my voice began to change. While still a bit smokier than most women it's a lot more femme than it was. I like to think of myself as a Beverly D'Angelo or Kathleen Turner type voice. Pretty deep and husky for a woman but still feminine and alluring. Second, my hair growth changed dramatically. Facial hair became almost non-existent. I never had much of a beard anyway but now I have essentially none. I need a little laser touch up here and there from time to time but it's no big deal. And the hair on my head is much finer and softer than is was. Almost a curse since it's a little harder to work with but I'll take the trade off. Finally, my body reacted beautifully to the hormones. My breasts began to bud and I was an A cup in six months. I was almost a full B in a year and a half. I got hips, which I thought was the best thing of all. And my ass filled out a bit. I was so excited with the changes. At the time I was working at another company and a few people even commented to me about the changes. Everyone there knew I was a transgendered person and except for a few, made no big deal about it. Most of my friends, then, and now, were either gay or transgendered as well. I didn't think I would be accepted in the straight world and so I didn't press the issue. A few years after all of this good progress I was in a car accident. The owner of the car had shut off the passenger air bag, why I'll never know, she had no kids. I hit the dash very hard and messed up my face badly. In retrospect it was a blessing in disguise because it gave me a reason for surgery that helped change my appearance but at the time and as I went through four painful surgeries it was no fun at all. After I fully recovered from the accident and the surgeries I moved here and took this job. For all anyone knows at my new job I'm a woman. I know I get a look or two now and then but I don't sense that anyone knows my secret. I talk a lot of basketball, even though I don't really like it just to hopefully explain my height. I had one last surgery, for breast implants, just before I changed jobs. The Tanya in me wanted a pair of 44DD boobs but I knew I really wanted to look right and in the end needed only a small pair of implants to bring me up a cup or so. I've spent the last year or so here just going to work every day, hitting the gay and TG clubs a few nights a month and worrying whether I would ever fully feel I was a woman. In my heart I know I am a woman, no matter how I started out in this world. Emotionally I've been a woman since I really knew the difference; probably back when I was 9 or 10. Physically I've made almost every change I could to become a woman. Socially and intellectually I hadn't quite finished the transition. Until three days ago. In these days with you I've done things I've never done. That first blowjob in the club wasn't my first. But the others were all just suck offs, both for me and the owner of the dick. At first it was just to see if I could stomach sucking a guy's cock. Then it was to get better at it. In talking to other women most all of them say the same thing. I don't hate it but I don't really like it. If they told me I could never do that again I wouldn't mind. But I like doing it if it makes my husband, lover, fill in the blank feel good and want to be with me. Last night was my first fuck though. I've never been made love to before. And tonight is my first real date with a man. I'm so happy right now I could sing." She had talked for a long, long time, through drinks, dinner and desert and coffee. I enjoyed every minute. I kept watching her eyes dance when she was talking about Jenna, look down at the table sadly when she spoke of Carol or her parents and reflect the pain of the years to get her to this point. There was no doubt in my mind that Tina was a woman in the heart and the soul. I stood up and held her hand to help her out of her seat. I reached to open the door for her but the Maitre'd beat me to it. I held the car door for her. When we stopped outside her condo she looked at me. "Will you come up?" she asked. "With pleasure!" I replied as I pulled into a parking place. I must confess I watched her ass under the dress the whole way up the stairs. I liked looking at it. An old phrase I had once heard, "like two babies fighting under a blanket," came to mind. She opened the door to her condo and I did something I didn't expect and I don't think she did either. I shut the door with my foot, spun her around and kissed her full, deep and hard. I pinned her against the wall and kissed her long and deep. When we broke our lips apart she smiled softly, then threw her arms around my neck, pulled me too her and kissed me just as passionately. Without saying anything we moved to the couch where I sat and she lay down in my lap. I played with her hair and her face. We kissed now and then. We didn't need to talk. She got up and led me to the bedroom. I slowly undressed her to her VS panties and I smiled upon seeing them now knowing they were an early part of her journey to womanhood. She undressed me as well and we slid into bed. We kissed and caressed. I slid the panties off of her as we played. Then I spread her legs and positioned myself between her thighs she rolled her hips and brought her knees to her chest. She handed me some lubricant and I took my time liberally applying it to her and me. She breathed in sharply as I slid a finger inside her. She reached down between my legs and took hold of me. She guided me to her and then used her legs to urge me inside. We slowly rocked and moved softly easing me into her. Unlike last night this was making love. When I was fully inside she wrapped her legs around me and held me there. I caressed her breasts and teased the nipples a little. I stroked her thighs and calves. Being in touch with her smooth skin was glorious. She rolled her hips again and loosened her grip with her legs. I began to slowly piston in and out of her. In time she looked up at me and whispered, "Please give it to me." Increasing my pace I felt the pressure build in a few strokes. I went as deep as I could for my climax. I felt as if I was pumping gobs of liquid into her for 10 minutes though it could never have been that long. Weakened and spent I dozed with my body draped over hers. I woke to her tracing my ear with her finger and playing with my hair. I pulled her into my arms and we both slept. I woke to go back to my hotel. I kissed her gently and left as quietly as I could. I left a note that I would call that morning after stealing a business card from her briefcase.