Gina's New Life free porn video

It was a cool fall evening. The leaves were in the full glory of their autumn colors and in the half light of the sunset they seemed ever more marvellous than in the brightness of noon. Gina was preparing to go out again. Born Claude Eugene Monet he had decided long ago that he really should have been a woman and now lived and worked as a young woman and had changed his name to Regina Melody Monet. Though it was never totally legal, with the help of some less than reputable friends she'd secured a driver's license and other documents in the name of Regina. She was still genetically a male and had all the components with which she was born. She really didn't want to go through the surgery for a sexual reassignment. She did take hormones though and through them and exercise, she had developed a very sexy figure. At 5 foot 6 inches she weighed 110 lbs, had long strawberry blonde hair, hazel eyes, and measured at 34c-24-34. Perhaps a little thin but then she liked being able to dress like a fashion model and slim hips and a smallish bust sure helped. Now she was going to meet a new friend. Well not really a friend, at least not yet. Sonny, the person who had secured the fake ID for her needed her to entertain a guest from out of town. Gina really hated these 'dates'. Sonny paid her for these nights out and she got to keep any gifts she might receive but she didn't like the feelings she got from them, the feeling that she was a hooker, which on these nights she was. She did protest to Sonny but he threatened to cancel the identification arrangements he had set up for her. So until she could come up with something else she had to endure these "dates" that he set up. All she knew about her date tonight was that he was a businessman from England and he liked transvestites. Sonny, told her that she was to meet Sean, in the lobby of the Hilton so she should dress accordingly. Gina had just stepped from a scented bubble bath and had shaved her body except a small patch above her clitty (as she referred to her penis). She loved the way she smelled and the smoothness of her skin. Her pert breasts seemed so right as she looked at them in the full length mirror as she powdered her body. It was hard to believe that she'd worked as a firefighter for three years and had even been married to a woman for a short while. Now after a messy divorce where her wife had told the world about her crossdressing and her luck at the state lotto, she was able to live as she had always wanted. She quit her job with the fire department after she hit the lotto for $100,000.00 and invested most of it. She now worked at a fashion boutique as a salesperson and did these little favors for Sonny about once a month or so. She finished setting her shoulder length hair in spiral curls and went to her bedroom to start getting dressed. She had already laid out her lingerie for the night. She sat on her four poster bed with the pink lace canopy and began the ritual that she still never tired of doing. She fitted the boned bustier around her chest and fastened the hooks up the front. It was black with red trim and the cups of the demi bra had lace trim. Her small breasts filled the cups nicely and formed a very sexy cleavage. She pulled a pair of black lace panties up her sleek, long legs and worked the garter tabs through the leg openings. She wore pantyhose a lot, especially at work but she knew that guys really loved garters and stockings. She was hoping for a nice gift from this Sean as she pointed her red tipped toes into the rolled, black stockings and worked each one up her legs. She kept checking to make sure the seams were straight before she attached the garter tabs to the lace trimmed tops of the hose. Then she stepped into a pair of black heels and fastened the ankle straps. She smiled to herself as she thought back to the early days of her crossdressing when she had to wear pumps with five inch heels. That was foolish and these had a modest 3 1/2 inch heel. They were easy to walk and dance in and didn't attract a lot of unwanted attention. She went to her dressing table and carefully applied her makeup. Dark sultry eyes and red lips to match her nails. Not overdone but provocative to say the least. As she finished her makeup her mind wondered again, this time back to the boutique where she worked. A young guy, a teenager, had come in earlier that day looking for something for his 'sister'. Gina knew, nearly from the start, that he was buying for himself, especially after he refused her help. Then she saw him hold a dress up to himself casually as he took it from the rack. Gina remembered how difficult those times had been for her when she was a teen. She was going to ask him if he wanted to try it on but decided not to risk frightening him away. She did make a note of his name and address when he paid with his credit card. He was 19 years old, oh to be 19 again she had thought. Perhaps she would call him sometime, probably not, but she would watch for him in the store. Her makeup done she took her hair out of the rollers and combed it out. It looked fabulous! The spiral curls were very sexy and they bounced on her bare shoulders. She went to her closet and picked her dress for the night. It was a black sheath cocktail dress, very sleek and form fitting. Thin straps held up the top as the shimmery material clung to her lithe body and the hemline was about 3 inches above her knees. She added a few items of fashionable jewelry and checked the time. It was just 8:30 and she still had a lot of time so she walked to her patio. She sat in the cool autumn air and watched the lights from the traffic on the street below. She really hoped the Sean was not like the last guy Sonny had set her up with a few weeks earlier. He wasn't her type at all because he wanted her to fuck him. Although she did what he wanted because he was paying it was not something she liked doing. She would much rather have a hard cock sliding into her ass than the other way around. She had been bisexual since she became sexually active in junior high school, though she never had a bisexual experience till her senior year in high school. Sex with girls, though quite fun, never really seemed fulfilling. Passive by nature she loved to be cuddled, caressed and made love to. The first time she had sex with a guy was at a costume party where she was dressed as a harem girl. The guy never realized that Gina was a guy and she gave him a blowjob in the back of his car. Hardly an earth shattering experience for her but gratifying none the less. Now she was going to meet a guy who knew what she was and wanted sex with her. Oh well, she thought as she lit a Virginia Slim, you've come along way baby. It was 9:15 now and she was to meet him in 45 minutes so she gathered her purse and checked its contents. There was some money, her ID, lipstick, blush, and of course condoms. Like American Express, she never left home without them. The night air had been chilly, her nipples were erect under her bustier, as she grabbed her leather coat from closet on the way out. She walked into the parking lot and to her car. She loved the way the cool air swirled around her legs as she walked and after all these years she still loved the thrill of being out in public dressed to kill. There were several teens loafing about in the lot, not bad types, but kids who lived in the building. They yelled hello to her and one ran over to hold her door for her. As she slid into the driver's seat of her flame red Corvette she heard the boy sigh as her dress slid up to reveal her stocking tops. She shooed him away as he blushed after being caught sneaking a peak. As much as she would have liked to introduce this young stud to the joys of sex, he was much too young for her. The 20 minute drive downtown was totally uneventful as usual. She remembered how much of a thrill it was years ago just to drive around while dressed. Something she did every chance she got back then. Now it all seems so silly although she still liked to flash a little thigh to the truckers she passed, she would probably never grow out of that little quirk. She arrived at the Hilton with time so spare and the valet opened her door. He offered his hand to assist her from the seat and she graciously accepted his offer. She loved being treated this way. He gave her the parking voucher and then climbed into her car. Gina looked over her shoulder as she walked away and just as she thought he was still staring at her ass so she winked at him. She walked into the lobby and surveyed the room. There he was, standing next to the payphone and he was wearing the gray suit and smoking the hand carved pipe just like Sonny had told her. He looked at her and then looked toward the door again. Obviously he didn't think she was his date and that was usually a good sign because he was probably looking for someone who looked more like a man in a dress. She walked over to the payphone and pretended to make a call. He was watching her as she leaned against the wall. Her perfume had captured his attention. When she was sure he was totally consumed by her she hung up the phone, turned to him and introduced herself. The password phrase was for her to say, "Hi Sonny sent me". She said the words and his mouth fell open. He stammered his disbelief that she was so beautiful and she thanked him for the compliment. Then he asked if she would like a drink before dinner. She accepted and hooked her arm around his as they walked to the hotel lounge. Shortly after they sat down in a booth and ordered drinks the waiter came over to the table with a portable phone. Sean took the call and after a few minutes hung up. Then he asked Gina if she would be upset if he excused himself for a few minutes. Something had gone wrong with a business deal and he had to go back to the office. She told him it would be OK as long as he came back. He handed her some money and said he would be back as soon as possible and that she should have a few drinks till he returned. He left and the waiter brought Gina a glass of wine. As she sipped the wine her mind again began to drift, back to when she was married. Her ex-wife Judy knew about her crossdressing and didn't mind it too much. She let Gina dress at home as long as she promised never to go outside. That was a promise Gina could not keep. Judy also had no idea that Gina was bisexual, at least not till that fateful day. Several months before that day Gina came home early from work one day and as she pulled into the driveway she noticed the Fed Ex van parked across the street. She walked in the back door and as she moved into the living room she heard voices from the den. She crept up to the door then thought it would be better if she should go outside and look in the window. When she looked in she saw something she couldn't believe. Her young wife of less than a year was bent over the back of the desk chair getting royally fucked by the Fed Ex man. The man's cock was at least 9 inches long and as he rammed it into her she cried out with each thrust. Gina watched as the man fucked her hard for a while then pulled her off his cock and pushed her to her knees. She then eagerly took the man's huge cock into her mouth and sucked him off. The man came in great gobs of cum that splashed onto her face and ran down her chin. She lapped up his cum and sucked him till he was hard again. Then he fucked her again. Gina left before the man was finished and parked down the street where she waited for the van to leave before she went back to the house. Her wife had that freshly fucked look about her when she walked inside. She could smell the sex on her. Gina told her what she'd seen and Judy was shocked and started to cry. Gina too was shocked in that she was not jealous, just concerned as to what had led to this day. Gina told Judy how she felt. Judy confessed that she needed more than Gina could give her. Gina realized that she wasn't much in the sex department and told Judy that if she felt the need, she could take a lover sometimes. The irony of the situation was that on the fateful day. It was Gina's day off from work and as usual she was dressed up. She was wearing a black spandex mini dress, black hose and heels. Her hair was not very long back then and she wore a long, curly, blonde wig. She finished the house work and was just relaxing, watching the afternoon soaps when the door bell rang. As usual she peaked out the window to see who was at the door. If it was someone she knew, or even thought she knew, she just wouldn't answer. But if it was a stranger or especially a salesman she would answer the door and try out her Gina persona. Those experiences never led to anything, they were good practice for when she went out dressed. This time it was the same Fed Ex man that she'd seen screwing her wife. She thought, 'this could be interesting'. Judy had really been having a orgy since Gina had told her she could take other lovers. She was out at least 3 times a week and would come home reeking of sex. Gina didn't really mind because Judy really seemed happy and Judy still had no idea that Gina was attracted to guys. Gina answered the door and greeted the Fed Ex man with a bright, sexy smile. She stepped back from the door and asked him inside. He handed her his clipboard for a signature and set her package down on the floor. It was a new outfit Gina had ordered from a kinky fashion catalogue. The man's photo ID tag said his name was Robert and he asked her if Judy was home. Gina smiled and said that she was at work but that Judy had told her all about him. Gina handed the clipboard back to him and noticed a rising bulge in his pants. He then asked Gina if Judy was related to her. Gina said Judy was a close friend and had told her all about her encounters with him. She then asked if he could stay awhile and Robert said he could. It seemed he always delivered to Judy as his last stop so he could "visit". Gina walked to the living room with Robert right behind her. He was watching her ass wiggle in front of him and was thinking that this would be fun. He sat on the sofa and Gina sat directly across from him. As she sat her short dress slid up her sleek legs revealing the tops of her stockings. She did nothing to correct this and could tell by the look in Robert's eyes that he liked what he was seeing. They talked for a few minutes when Gina got up and sat on the floor in front of him and looked into his eyes as she laid a manicured hand on his thigh. He needed no further encouragement, he smiled at her and told her to go for it. She unzipped his pants and took his cock in her hand. It was even bigger than she remembered as she kissed the tip as Robert moaned his pleasure. Gina licked the sides of the veiny shaft to lubricate it and then took it into her mouth. It felt fabulous as she began to suck his cock. She'd not had a lot of experience at this but did what she knew felt good. It was obviously working since Robert was moaning and fucking her face with blind passion. Gina stopped and looked at him so he told her to please continue. She said to him that there was something he should know about her. Then she told him she was a transvestite. Robert looked surprised for a moment, just a moment though, then looking at his swollen cock he said he didn't care and told her to finish what she'd started. Gina now sucked with renewed passion since now she'd nothing to hide. His shaft was nearly touching the back of her throat with each thrust. Robert grabbed the back of Gina's head and pulled her off his cock as he began spurting cum over her face and into her gaping mouth. Robert lifted Gina to her feet and hugged her, kissing her passionately over his fresh cum. His still hard cock nestled nicely between Gina's naked thighs so she began sawing back and forth on his cock. She asked him to fuck her and he didn't need to be asked twice. He pulled her panties down and pushed two fingers into her ass. She was glad she had douched and put some lotion on her ass earlier. He lifted her up a little and lowered her onto to his cock while still standing. Gina wrapped her sexy legs around his back and pulled herself down onto his cock as far as she could. He had glorious stamina. He fucked her hard and ruthlessly. She loved it and couldn't believe how great it felt. She had used a dildo many times but a rubber dildo could never compare to the feelings of a warm hard cock in her ass. Robert announced that he was going to cum again and Gina readied herself for her first cum injection. He started to cum and fucked her even harder. She could feel the love juice filling her ass and it was the best she ever felt. Robert had just pulled his cock from her ass and was kissing her again when Judy walked in the front door. Well, envision this, Robert, standing with his cock pointed toward the ceiling with sexy Gina, and her panties down around one ankle. There was cum running down the inside of her legs and yet more in her hair, on her neck and breasts. Judy went ballistic. She called Gina a faggot and screamed at Robert to leave so he left in a hurry. Gina couldn't believe she was acting this way because it had been Judy who had fucked him first. Well, the next day Judy left but before leaving she mailed some photos of Gina dressed as a girl to all Gina's relatives. The divorce was settled out of court because Gina had a few witnesses of Judy's activities too, so to avoid any further embarrassment she agreed to a modest settlement. Gina's brother disowned him but his mother said she didn't care and she still loved her very much. That had been 2 years earlier. Now as she sat in the lounge of the Hilton, dressed to the nines and waiting for her date for the night, she realized it was all for the best. Sean returned a short time later and he kissed her on the forehead and apologized for having to leave. He'd only been gone 30 minutes and Gina didn't really mind. He sheepishly asked her if she would mind another change of plans. When she shook her head, he asked if she would mind going with him to a meeting with a few clients. After the meeting they would come back to the hotel for the night. Gina said she didn't mind because he was paying for the night and whatever he wanted to do was fine with her. They walked outside the hotel and there was a black limo parked at the curb. The chauffeur got out and opened the door for them indicating that Sean was better off than Gina had thought. Once on the way Sean pulled Gina close to him and kissed her again telling her she was the best date he ever had. She placed her hand on his leg and thanked him with another kiss. Sean was rubbing her thigh and toying with her garter tabs as they cuddled on the ride across town. Gina's mind wandered and she thought back to the first time she'd been picked up at a bar. After the divorce, Gina rented the apartment she lived in now and went wild. She met a couple of local transvestites through a local computer bbs and together they would go to a local gay bar called The Alternative. It was accepting to all lifestyles and there Gina could really be herself. The second night she was there with her new friend and older 'sister' Kathy. She was sitting on a barstool sipping a drink when a guy sat next to her and offered her a refill. She accepted and chatted with him for a while. Kathy excused herself and went to a talk with some other "girls" as he and Gina got acquainted. He was married and good looking so Gina told him up front that she was not a real girl. He said that he knew that and he'd been asking around about her ever since he saw her walk in the door. He said he always fantasized about sex with sexy passable TV and would like to try her. Gina blushed at his frankness and asked what his wife would think. He said she might be interested too since she was a closet lesbian and then shocked her as he pointed her out. His wife was across the room sitting in a booth with three other decent looking women who were obviously more than just friends. Gina told Chad that she really didn't enjoy straight sex with women. He then asked if she would consider eating out his wife's cunt while he fucked Gina. That sounded like it might be fun to Gina. After a couple more drinks, Gina agreed to go home with them so she made sure Kathy had a way home and met them at the door. So Gina found herself going with Chad and his wife Rachel. Rachel then kissed Gina and thanked her for accepting their offer. Rachel drove home while Gina and Chad got to know each other better in the back seat. By the time they arrived at their home in a classy section of town, Gina's leather skirt was off and Chad's cock was dribbling pre-cum over his leg. They got out of the car while Gina was trying to pull her skirt back on but Rachel told her not to worry about it and helped her from the car. Rachel then kissed Gina and drove her tongue into her throat. Chad said that they'd better go inside before they all got naked in the driveway. Gina and her new friends walked into the house with Chad feeling her ass the whole time and once inside things really started to go wild. When they got to the huge living room, Rachel dropped to her knees in front of Gina and slowly lowered her panties. Chad was kissing her and feeling her breasts as Gina was palming his cock through his pants. Before long Gina was on her back on the rich plush carpet with Rachel sucking her "clitty" as Chad straddled Gina's chest feeding his cock to her. Chad was fucking her face furiously and soon Gina could feel his cock twitch and fill her mouth with hot slick cum. Gina swallowed it all as she began spurting into Rachel's mouth. Rachel lay back and Chad, who quickly recovered quickly slid his cock into Rachel's waiting cunt. Gina sat back, smoked a Virginia Slim and watched them making love. After she finished, she put out the cigarette and moved over to them. She managed to get her head between them and was flicking Rachel's clit with her tongue as Chad continued to fuck her. Rachel soon began shaking with an impending orgasm. Chad then pulled his cock from Rachel's cunt and Gina ate her to a glorious orgasm. Chad moved around behind Gina and slid his cock into her upturned ass. Gina gasped as it entered her because it felt so good. She went back to eating Rachel's pussy as Chad pounded her ass relentlessly. In a short time he filled Gina's ass with his cum as Rachel had another shuddering orgasm. This went on most of the night till Chad could not get it up anymore. So then they finally fell asleep in each others arms. Sean and Gina arrived at a downtown office building and went to the meeting room where Sean's business associates were assembled. Gina sat in a corner of the room listening to the banter between the men who were all "type A" businessmen. The stress of the dealings was showing on them all as she looked around the room at each of the men. Several were definitely not her type. Two were old, overweight bald guys and she would not really like being with either of them. One was a Middle Eastern guy and although he wasn't bad to look at, her experience with these guys was that they were too demanding of their women. The others were good looking guys and she found herself fantasizing about them, in particular the tall black man who seemed to be running the meeting. He was stealing glimpses at her legs occasionally as he talked and when someone else was speaking he was blatant with his stares. Gina, enjoying the attention let her dress slide up to reveal that she was wearing stockings and not pantyhose. He noticed so Gina excused herself to go to the ladies room as all this fantasizing had made her a little uncomfortable. She got Sean's attention and asked where to facilities were located. He handed her his key to the executive washroom and she left the room. She was in the restroom for several minutes when she heard someone else walk in. She stood, arranged her dress and walked from stall. There stood the black man and he smiled at her. He said he was sorry for walking in on her. Gina said it was OK that she would be done in a minute. She walked up to the mirror and started to fix her makeup. She looked through the glass and saw him standing behind her watching her ass and legs so she asked him in a sexy voice what he was looking at. He told her blatantly that he was looking at her fantastic ass and Gina then noticed the rising bulge in his slacks. She turned and smiled at him, blushing she thanked him. He then moved toward her and she stopped him. She told him that she was not all she seemed to be. He looked confused at first as she told him she was a transvestite then she noticed his cock had grown even larger than before. He pulled her into his arms and kissed her as his hands slid down her back and fondled her ass. He asked if she was a hooker so she told him that she did take money for these special dates that Sonny set up but that she worked in a boutique. He kissed her again and this time Gina was eagerly undoing his pants and freeing his cock. She looked down at it as she pulled it from his pants. It was true about black guys she smiled to herself as he pushed her to the tiled floor and grabbed his cock by the base, rubbing it against her cheek. She responded by licking and kissing the tip. Then he forced it into her mouth and her mouth stretched to accept it all but couldn't swallow more than half of it. She grabbed the remainder with her delicate hands and jacked it off as she sucked and licked the tip. In a matter of minutes he filled her mouth with a hot load. Gina licked his cock clean and he pulled her to her feet and kissed her again. He said they had better get back before someone got suspicious. Gina turned back to the mirror and re-did her dishevelled makeup and clothes. When they walked back into meeting room everyone looked up and Gina got the feeling they knew. She settled back into her chair and reached into her purse for a cigarette. In her purse she found a crisp one hundred- dollar bill with a phone number written across the top. She looked up at the black man, she didn't even know his name, and he smiled and winked at her. It was going to be a productive night indeed. Back in the limo on the way to the hotel, Sean asked what had gone on when she was out of the room. She told him that the guy walked in on her in the restroom and she ended up blowing him. Sean smiled and said that he had a feeling that had happened. He wasn't upset he apologized for the inconvenience of making her go to the meeting. When they arrived back at the hotel they went straight to Sean's suite. Gina then went to the bathroom to freshen up and Sean called room service for a bottle of champagne. When Gina came out Sean was sitting on the edge of the bed smiling. She asked him what was so amusing. He told her he was thinking about her and Raymond, the guy from the meeting, screwing around in the restroom. She asked if that turned him on and he said it did. He then told her room service was bringing up some champagne and she should try to seduce the boy that brought it up. He would hide in the closet and watch what happened. She agreed as long as he was attractive to her. A few minutes later a knock came to the door so Gina looked out the peephole and seeing the room service guy was a hunk she turned to Sean and told him to hide. Taking another look the guy was blonde and tanned, and looked to be in his twenties. Sean hurried to the closet as Gina undid the zipper on the back of her dress to the waist. She answered to door and turned so the guy could see her sexy lingerie under her dress. He followed her into the room and set the bucket and bottle of champagne on the nightstand. As he turned for his tip, Gina shrugged her shoulders and her dress fell to the floor. He stood there in amazement as Gina stepped from the dress and walked over to him and reached for his crotch. Without saying a word she pushed him to a sitting position on the bed and she got on her knees on the floor and unzipped his pants. She pulled his thickening cock from its confines and kissed the tip. She asked if he minded and of course he didn't. She licked the sides and nibbled the tip. Then she heard the closet door open and Sean walked out stroking his cock. The guy was shocked and tried to get up. Sean told him to relax and enjoy himself. Sean walked over to them and knelt behind Gina as she continued to suck the stud to full hardness. Sean worked a finger into her sexy ass not removing her panties but by sliding them to the side. She moaned around the cock in her mouth. Then she felt Sean's cock pressing against her puckered hole. She pushed back against it and it slid into her ass all the way. This was fantastic. Sean began to fuck her ass as she went back to work on the stud's cock. Gina's world had narrowed to two things, the cock in her ass and the one in her mouth. All she cared about at that moment was to have them spew forth their juices into her willing body. She was not to be disappointed. She felt the bellboy's cock stiffen in her mouth and start to gush cum into her mouth. She pulled it out of her mouth and let it spray into her face and hair. Three or four jets of cum shot out into her face. She used his cock to rub the juice into her skin. At nearly the same time Sean filled her ass with his load. He came a lot and it was leaking around the sides of his cock. Then it began to run down the inside of Gina's thighs. She felt great that she had cum herself. It was such a good feeling to cum without even touching her clitty. Just like a girl. The bellboy thanked her for the tip and left. Gina climbed onto the bed and Sean snuggled next to her, they fell asleep in each other's arms. It had been quite a night for Gina. Sean was still sleeping when she left and she crept from the room so as not to wake him. He had left her another little gift in her purse sometime during the night. It was a check for $200 and a gift certificate to a downtown fashion shop for $300. When she arrived home there was the envelope in her mailbox that was always there every time she did these dates for Sonny. Inside was another $400 so it had indeed been a good night, though Gina still wanted to find a guy to settle down with and end these nights of being a hooker. The remainder of the weekend was really uneventful. Her mom called and asked her to come home next weekend. Gina told her she would think about it, though she knew in the end she would. She asked her mom if she could come home as Gina this time instead of acting the part of the male. Her mom hesitantly said it would be OK if she wanted to be Gina around her but preferred her to stay at the local motel in case someone from the family should stop by. Although Gina was really growing tired of those Bible belt attitudes she said she would stay at the Holiday Inn when she came home. The week at work literally flew by. The guy who had been in the store before was in again. Gina sold him a cute little sapphire blue velvet dress for his "sister". Gina wished she could see him in it. Finally on Friday afternoon she loaded the 'Vette and left the city to drive to her mom's home and to drive back in time. At least that is how it seemed. ******************************************************************* If you enjoyed this story, let me know and I will contribute more. [email protected]