Gina Brings Pleasure To A Sweet Older Man free porn video

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I have an almost insatiable sexual appetite and am usually willing to have sex with someone after a few dates if I find them attractive and they treat me decently.  However, I never suspected I might find myself in a situation where I would be having sex for money.  That changed when I met a really sweet older man who just wanted someone to help him feel alive again. 

I am a very passable shemale who loves to dress in revealing clothing and get a lot of attention from men.  I have been told I am a very talented sexual partner, especially when it comes to oral sex.  I love to suck cock and love to have my mouth full of hot, creamy cum.  I like the feel of a thick, hard cock in my ass almost as much.    

I spend a lot of time in the outdoors and regularly hike the various trails near my home.  It was there I met the man who would make me his personal whore.  His name was Sebastian.

I met Sebastian on one of the local hiking trails near my condo.  I usually hike in very skimpy shorts, walking shoes, and skimpy tops because I like the attention I get.  At the time I met Sebastian I was in my early twenties and everything was firm and toned.  I am about five-foot-eleven and at the time I weighed about a hundred and fifty pounds.  I have long tanned legs and a round firm ass, with very feminine curves and a "Demi Moore" voice.  I used some mastectomy breast forms that give me a DD rack.  I have very small dangly bits that tape very flat. 

I had seen Sebastian several times on my various walks.  I always said "hi" as I walked past him and he seemed pleasant.  He seemed friendly and had an air of sophistication about him.  I had noticed him checking out my ass several times and he would look at me admiringly but was never creepy. He never spoke to me directly until one day when we unexpectedly met where two trails came together.  He introduced himself and asked if I would mind if he walked along with me.  I told him I would like the company and we continued on together.

"I've seen you walking here a lot.  Aren't you afraid to walk by yourself?" he asked.

"I've never had a problem here," I said.  "There are always people around so I feel pretty safe."

"I guess so," he said.  "My name's Sebastian.  What's yours?"  

"Gina," I replied.  "Nice to meet you."   

Sebastian and I made small talk as we walked.  He went on to tell me he was a widower and had lost his wife about three years before.  He was sixty three years old and lived alone in a house near the outer boundaries of the park where we were walking.  Sebastian was an attractive man, slim but not skinny, and seemed to be in pretty good shape.  As we walked he told me how pretty I was and commented on what great shape I was in.  I thanked him for his compliments.  As we walked, he asked me if I was dating anyone or was married.  I told him I wasn't in a relationship at the moment.  As we continued to walk on the trail, he asked me if I would come to his house for coffee.  

I hesitated for a moment, not sure if that was a good idea since I had really just met him and didn't know him from Adam.  For all I knew he could be a serial killer.  I think he thought he had been a little too forward and began to apologize profusely.  I assured him I wasn't offended.  I sensed he was lonely so I agreed to go with him. 

We walked for a few more minutes and came to a beautiful house just outside the park.  He invited me in and I immediately noticed the house was immaculate and there were photos of Sebastian and people I assumed were family members on the walls.  I noticed one photo of a much younger Sebastian with a pretty woman he identified as his late wife.  

We had coffee on his patio and chatted for awhile.  We sat close together at a bistro table in his yard and at one point, he brushed my bare knee with his hand as he talked.  I let it pass and he did it again, resting his hand on my knee for a second or two before moving it off.  I could see he was interested in more than coffee.  I smiled at him and said, "Sebastian, if you touch my leg again, I'm gonna think you like me."  

"I do like you, Gina," he said.  "I have been very lonely since my wife passed and have been starved for a woman's company."

For some reason, he looked so sad my heart went out to him.  "How long has it been since you have been with a woman?" I asked.  

"Since my wife died," he said.  "I just haven't met anyone who really seemed interested in me except for a few old grandmas who want someone to support them while they play with their grandkids." 

He went on to tell me how lonely he has been and how infrequently he had visitors.  He told me about his life and asked me about mine.  I shared some things but I didn't tell him I was a transexual.  I didn't want to embarrass him or make him mad when he realized he had made a pass at a shemale.

For reasons I can't explain, I stood up and walked up next to him.  I took his face in my hands and kissed him lightly on the lips.  He stared at me with a surprised look on his face and I kissed him again, this time a little longer.  This time he responded and his tongue slipped through my lips and met mine.  We kissed for a few moments.  His kisses were gentle and sensual.  

I pulled back and took him by the hand.  Right then I decided I would reach out to him and make him feel important and ease his tension. 

I led him back into the house and to the sofa in the living room, where I told him to sit down.  He complied.  I decided to deviate from my usual parameters for sex and had decided to do something that was unusual even for a cum guzzling slut like me.  I was going to sexually pleasure this total stranger if he let me.

I kneeled in front of him and looked into his eyes.  He held a steady gaze as I gently separated his legs.  He moaned softly as I undid his pants and released his penis from the front of his pants.  I noticed that in spite of his age, his cock was firm and substantial.  I looked into his eyes as I took his cock into my mouth, slowly rolling my tongue around the head and licking the shaft while I stroked him slowly.  I drooled saliva on his throbbing dick and began to suck him off deeply and slowly.  He moaned softly as I sucked him off, taking more and more of his cock down my throat until my nose pressed against his abdomen.  He gently ran his fingers through my long hair and pressed my head down on his cock.  He softly moaned my name as I sucked away.  

I sucked his cock like a street whore hungry for cum for about ten minutes, alternately taking him deep then teasing him with my tongue and teeth.  I could taste his pre-cum and noticed he was starting to tense up as if to cum.  Before he did, he whispered, "I want to make love to you Gina."  

"You may not want to if you knew the truth about me," I said.  

"You don't have to say anything," he said.  "I know you are not what you appear.  You were not born a woman."

I was floored.  At the time, I looked and sounded like a very sexy genetic woman.  I was totally surprised he could tell I was a guy. 

"How did you know?" I said.  

"Your hands," he said.  "A real woman's index and ring fingers are usually the same length.  Yours are not.  Otherwise, I might have been fooled.  It doesn't matter to me, Gina.  It would not be the first time I have been with a pretty man dressed like a woman."  

I was completely unaware of this detail.  "Sebastian, I don't usually have sexual relations with someone I just met.  I really feel you are sincere when you said you are starving for female company.  Today I am willing to do whatever you want to please you, as long as you don't try to hurt me."

"I would never do that, beautiful Gina," he said.  He walked out of the room for a minute and returned with a bottle of lotion.  He set the lotion down and took me into his arms and began kissing me on the lips and my neck, running his hands up and down my back and over my ass, squeezing my buttocks hard.  Our tongues melted together when we kissed.  He put his hand under my shorts and ran his fingers down my ass crack then began rubbing my dick.  I slowly pulled down my shorts and I removed the tape holding down my little dick and balls.  He moved down to my cock and kneeled in front of me, slowly licking the pre-cum off the tip of my dick before taking it into his mouth and sucking it slowly.  He did this for several minutes and I was shaking when he stopped.  

He lubed his cock and my ass with the lotion, fingering my asshole as he did so.  After he fingered my ass for a few minutes and licked up and down my spine, he had me kneel on the sofa facing away from him.  He moved behind me, placing one of his hands on my hip and grabbing my hair with the other hand, pulling my head back gently.  I felt the tip of his cock against my asshole as he pressed his cockhead against my tight man pussy,  His hard cock suddenly popped inside me.  There was no pain and I easily took him in.  It felt so good to feel each inch slide inside me.  He slowly buried his cock inside me until I felt his balls slap against my thighs.  

I hadn't planned on being fucked in the ass that day and had not prepared.  I guess I just happened to be clean because he began fucking me enthusiastically, grabbing me by the hip and pulling my hair at the same time.  There was no indication of smell or leakage other than lotion oozing down my ass crack and balls.  He pistoned his cock into me for some time as I felt my own orgasm starting to build.  

Sebastian suddenly moaned louder and his body shuddered.  I knew he had shot his load of cum inside my ass.  He pulled me against him and buried his cock deep inside me as he came.  I was stroking my cock while he fucked me and my orgasm let go.  It felt so good to have his cock inside me while I shot my load onto the hardwood floor.  Sebastian still gripped my hips while he buried his cock in me.  He stayed inside me for several minutes before pulling out. 

I went into the bathroom to clean up and when I returned, he was dressed and kneeling by the couch, cleaning up my man juice from the floor.

Sebastian walked up to me and extended his hand.  I saw he was holding a wad of twenty dollar bills.  He started handing them to me and I stopped him and said, "Sebastian, I'm no pro.  I just wanted to make you happy today.  You don't have to pay me anything."

"Please Gina, I know you were just being kind, and probably wouldn't do this again on your own," he said.  "I was hoping we could do this again.  In fact, it would be worth it to me to pay you not to be with anyone else, and just visit me once or twice a week.  Just tell me what it would take for you to be my girl until I can't get it up anymore."   

I told Sebastian I would think about it.  I really enjoyed having sex with Sebastian but had never thought about selling myself.  After thinking about it, the thought of being his sex slave kind of turned me on.  I decided I was willing to be his exclusive sex toy if he was willing to pay. 

I met him a few days later on the trail and we walked together.  I told him if he would give me $100 for a blowjob, or $200 for a blowjob and a fuck, I would be willing to be his concubine.  He readily agreed and we began an almost three-year relationship of regular sexual rendezvous.  We experimented with many different kinds of sexual activities, including bondage and role playing.  He especially liked it when he tied me up and he made me beg him to fuck me or let me suck his cock so he would release me.  He loved to cum all over my face and in my mouth as I swallowed his cream all down then licked him clean.  Although he would sometimes be domineering when I was being his sex slave, he was always sweet afterward and always paid in cash after our visits.  He would sometimes pay me much more for my services than we had agreed on. 

Unfortunately, he wasn't able to keep things going and eventually we stopped meeting.  He passed away about five years after we met.  I can only hope I made his final years more enjoyable.  

A few years later I again found myself fucking my boss and his friends for money but that didn't last very long.  I found that I liked being lusted after and used as a sex toy by otherwise straight-laced men with kinky fantasies.  As long as the clients didn't get too carried away and get violent, I was happy to bring their fantasies to life.

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Gina and her horsies1

It was a lovely warm August day, and little Gina had just woken up, thoroughly refreshed, from a lovely dream about big cocks and lots of fucking, and her little pussy was dripping wet, and gagging for some deep penetration, and a good, hard, pounding shag… She sat up in bed, and stretched, and let out a huge yawn. She then swung her legs over the side of the bed, stood up, and toddled off to the bathroom, where she had a pee, and attended to a few other things. After this, she...

2 years ago
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Gina and her horsies0

It was a lovely warm August day, and little Gina had just woken up, thoroughly refreshed, from a lovely dream about big cocks and lots of fucking, and her little pussy was dripping wet, and gagging for some deep penetration, and a good, hard, pounding shag… She sat up in bed, and stretched, and let out a huge yawn. She then swung her legs over the side of the bed, stood up, and toddled off to the bathroom, where she had a pee, and attended to a few other things. After this, she...

4 years ago
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Ginas Thank You Surprise

I get pretty excited when my company sends me to Cincinnati for the week. I think my wife can sense something and I have been getting a little nervous she might be catching on. Over the last year I have made the trip seven times and on the first trip I met up with Gina a nice 35 year old CD I friended on Xhamster. We started out slow and met for a quickie but the last couple of trips we spent the entire night together feeling more comfortable and excited with each meeting.Gina has always met me...

2 years ago
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Ginaacutes Gyno Club part four

Gina and Leslie are lovers. Both live at the campus of a small exclusive university. Tall and strong Leslie lectures there. Gina looked forward to a long hot Summer together in all privacy. However, first day of Summer holiday, Connie - the skinny teen sister of Leslie - came for a long stay. "Privacy lost", the lovers thought.Soon after her arrival the tasty teen got seduced and hot. She fell in love, came fast and lost her virginity. It happened all so beautifully, that a brilliant...

2 years ago
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Gina Ch 02

‘Scott, do you remember when we watched ‘Henry and June’?’ Gina’s question was as unexpected as it was oddly-timed. ‘I’ll never forget it,’ I replied, my mind flashing back to the night we watched the film for the first time. It was based on the erotic journals and real-life experiences of the famous writer Anais Nin and focused on her love affair with writer Henry Miller and his wife June Miller. ‘Well Scott, I think I’ve found my Henry and my June,’ Gina responded. As soon as these...

1 year ago
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Gina encounters stepdad again

Note: This story is completely fictional! Gina lie in her bed thinking about what just happened between herself and her step dad. She felt dirty, humiliated. Why didn’t she try harder to resist. She hated herself for enjoying the fuck so much. It was morning and Gina had not slept much that night, she lied in bed until late that morning and her mother had already gone to the office. She was waiting until Peter had also left but he seemed to be lingering in the house, perhaps waiting for her to...

Incest
3 years ago
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Gina

The plane was about to land. All I could think about for the last five hours was Gina. I kept thinking about what she would be wearing and what she said the last time we met. Gina is about 15 years younger than I. She worked for me a few years ago when I hired her right out of college. I will never forget her first day in the office. She was wearing an off-white blouse with a short navy blue skirt along with 2 inch heels. Her brown hair glistened and her smile could light up a room. I always...

3 years ago
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Gina

The plane was about to land. All I could think about for the last five hours was Gina. I kept thinking about what she would be wearing and what she said the last time we met. Gina is about 15 years younger than I. She worked for me a few years ago when I hired her right out of college. I will never forget her first day in the office. She was wearing an off-white blouse with a short navy blue skirt along with 2 inch heels. Her brown hair glistened and her smile could light up a room. I always...

Straight Sex
3 years ago
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Gina 3

It was mid afternoon when I arrived home. Gina and I had been together for six months and we’d decided it was time for my parents to know about us and we were going to go together, but on the way Gina had second thoughts. I stopped the car and we discussed the matter before eventually deciding it may be better if I went alone so that if things became nasty, Gina wouldn’t bear the brunt of any verbal abuse. I turned the car round and drove Gina home and then made the journey home alone. As I...

2 years ago
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Ginaacutes Gyno Club part zero

Gina´s Club is founded in part one. When we meet Gina she´s just 18. Graduated two weeks before. That was her biggest party so far. Now it´s her birthday early Summer. She invited all her best girlfriends, even Leslie, who´d already taken her MA last month. And some boys from class and sports of course. But after trying two of the most promising and being steady with them for a few months, she´d lost most of her interest for them. As always, Leslie stunned Gina with her looks, confidence and...

3 years ago
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Gina 3

It was mid afternoon when I arrived home. Gina and I had been together for six months and we'd decided it was time for my parents to know about us and we were going to go together, but on the way Gina had second thoughts. I stopped the car and we discussed the matter before eventually deciding it may be better if I went alone so that if things became nasty, Gina wouldn't bear the brunt of any verbal abuse. I turned the car round and drove Gina home and then made the journey home alone. As I...

Mature
4 years ago
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Gina the 55 year old submissive part 2

Currently on the couch in the tv room Jeff was facefucking his 50something mom Sharon for the 3rd time today , she hadnt swallowed yet so now was time for her dessert he smiled . Ummmh ummmh the blonde with saggy tits said as her pervert son/master used her face like a pussy. Sharon was collared , leashed,with nipple rings & 8inch spiked heels . She hadnt seen her husband in 48hours since Jeff & she had come down to her former basement. They had fucked, smoked some pot , drank some beer...

3 years ago
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Ginaacutes Gyno Club part one

Of course, Gina became a student at the small but very prestigeous and long time liberal - maybe even libertine - famous university in Ohio, where Leslie after her MA with honours, immediately was appointed as an assistent professor.Although they split up as a couple after her first year there, they were still best friends for ever and passionate lovers. Entering their third Summer as intimate girlfriends, they looked forward to another hot Summer of love between them and with their mutual...

2 years ago
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Gina

I love having sex with older women. I find they're usually so much better at it than their younger counterparts, plus they don't go gossiping to their friends after you've fucked them and quite a few of them are very grateful, especially the less attractive ones. I don't care myself, as long as they're over forty and not too fat, then they are fair game. My first oldie was a teacher from school. Miss Shaw was her name, Helen Shaw. She was fifty when I fucked her and still a miss. I was twenty...

Mature
3 years ago
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Gina

It all began in August, a couple of weeks before school started. I was going to be a senior, and while I understood the importance of that fact, I was unimpressed. First, I was not going to go off to college. My grades were good, but certainly not stellar, which they would have had to be for me to get a scholarship. Failing that, my parents could not afford anything more than community college. I was also seriously considering the military as a way of making enough money to go. Second, I was...

3 years ago
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Gina the Girl Scout and Pitbull PeteChapter 2

Gina Valentina is my younger sister by about eighteen months and I am almost eighteen but still shy of that magic moment when I had the right to say no and be an adult without need of supervision. I was still in the explorer scouts and was planning to enter the military as soon as I graduated which would be in less than ninety days. Enough of that this story is not about me. This story is about Gina and her constant companion Pitbull Pete. I have to tell you that Pitbull Pete is an ugly...

2 years ago
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Ginaacutes Gyno Club part two

In part one Leslie founded Gina´s Gyno Club. She came home from jogging to find her ten years younger sister Connie coming first time, by the continued kisses on her pussy of her own favourite love, feminine petite Gina. Leslie kisses Gina on her lips to smell her sister. "Hmmm, you taste so sweet, Connie honey! My dears, I´ll jump under the shower. Gina my love, please pull open another good Bordeaux. We have something to celebrate: our Club! ;-)". Obediently Gina opened a bottle of a good...

4 years ago
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Gina wants only anal

My lovely wife had travelled far away from town to visit some old friends; so I could enjoy home alone just for some days.I had been chatting during night time with a married lady.She loved to cheat on her husband, just because he was a loser.Then finally I accepted her invitation to meet at a restaurant.Her name was Gina. She was a sensual good looking woman in her late forties; red hair and nice green eyes. She had long legs to die for; round buttocks, tight waist. She looked as a perfect...

2 years ago
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Ginaacutes Gyno Club part three

After part two, the three dear girlfriends fell asleep in each others arms.Gina was so excited that she´s drank half the bottle of Bordeaux on the evening of their first threesome. Leslie had downed two large glasses and her ten years younger sister Connie drank only her first ever glass of Bordeaux.Saturday morning Gina woke up as last, from the sound of the sisters splashing in the shower. She soon joined them. Again they indulged in long loving mutual fondling till all were tired from...

1 year ago
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Ginas Retro Tit Torture

                                                                  GINA’S RETRO TIT TORTURE  Back in the late seventies my ex-wife spent a few weeks in the LA area. This was a couple years before we met and were married. Her older cousin had an apartment there and invited her out west, she was told there was a lot of work in movies and modeling and should get there as soon as she turned 18. Turns out the cousin was actually working for a sleazy escort service and Gina found out when she arrived...

3 years ago
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Gina gives the perfect blowjob

Gina and I were going to dinner so we had planned to meet at her apartment at six. I drove over and let myself in. "Hey, I'm here," I said as I entered but she was nowhere to be seen. Looking around her living room toward the kitchen I tried to spot her. "In the bedroom," she said, "I'm finishing something up that you might enjoy seeing." I stopped as I entered the bedroom. Gina was spread eagle on the bed. Her beautiful pussy visible from the door. Her black pubic hair was trimmed to extenuate...

Straight Sex
1 year ago
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Gina

As in my other story. Rudy my longtime friend was caught cheating by his wife,Gina. He paid the price of haveing to watch me fuck his wife and fuck her ass. Couple months have gone by, I keep in touch with Rudy, seeing if he is still fucking around on Gina. He swears he isnt,but is makeing excuses why he isnt comeing home on weekends for awhile. Gina is very suspious, cant blame her. So we decide to take a road trip,she wants to know if he is lieing! 3 hours later Gina and I check in to a...

2 years ago
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Ginaacutes Gyno Club part six

Gina´s Gyno Club waited for its first new girl, eager to earn membership by becoming a woman there. Young teen Connie was the first to lose her virginity at the hands and kisses of Gina. Her experience was the reason the Club was founded.Connie became first honorary member at age 15, at the start of Summer. After Summer holiday she would check among her girlfriends ... Tight tall Tina maybe? She felt warm for her class-mate, who shared her skinny long-legged locust´s looks. Before holiday Tina...

4 years ago
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Gina the 55 year old submissive

Chapter 1 Jeff was smoking a joint as a fifty year old blonde with large tits with a bit of a sag sucked on his 10 inch prick. He was casually watching a video where this 20 year old guy was dominating two ladies in their fifties. Tonight he was gonna do that , so he was watching to get some ideas. As his mom Sharon kept sucking his dick , he called out to his stepdad to get him a beer . Philip like Bill (Gina's husband ) was now also a cuckold and only got off by watching his wife...

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