Toni Encounters Greg free porn video

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Anthony Lorimer was aged in his early thirties. Over the last year or so, he had progressed from occasionally putting on his now estranged wife's underwear when she was not at home, to the stage that he was now at of going out fully dressed and made up as a woman. When dressed Anthony became Toni and, in part due to his build and bone structure, he became a very attractive female.

In the early days, he would wank whilst wearing his wife's knickers but now he had become so adept at becoming 'she' that he would go to a club in a neighbouring town and get picked up by males of varying ages. This often culminated in the male either getting a wonderful blowjob or ejaculating in Toni's asshole.

His wife had left him for another man but she, to the best of Anthony's knowledge, had and has no idea of his liking for 'becoming a woman'. Anthony himself had had a couple of nights of sex with women, as a man, since his wife's leaving, so he now classed himself as bisexual.

Anthony's progression to full-on Toni was gradual, through putting on skirts and blouses as well as underwear to adding make-up to venturing nervously outside and then to a first encounter with a male. This first encounter did not go well and Toni hurried away with the man yelling a load of not very complimentary expletives after the man discovered that 'she' was a he.

It took a couple of weeks or more after that before Toni was confident enough to go out dressed again. But in those days in between, the face that looked back from the mirror had become far more female looking. The second time was much better and Toni satisfied a middle-aged man with his/her mouth although at the end of that particular encounter Toni was unsure whether the man knew that he had just been blown by another male or not.

As confidence grew, Toni ventured further afield because although there was a bar that catered for quite a cross-section of sexual tastes in the local town, he/she did not want to risk coming across someone they knew. So he/she started using a similar bar in a nearby town. Over time, Toni became very popular with the clientele in that bar and there were a number of men that had snogged and groped this very attractive lady and a few of them had got to insert their penis into Toni's ass.

We are now nearly up to date, and Toni, looking ravishing, was cruising not too far from her home when to her horror she saw a workmate approaching from the other direction. The workmate was Greg Akers who was a similar age to Anthony and as the gap between them closed Toni started to panic a bit. She put her head down and hoped that Greg ignored her but, although married, Greg had an eye for the ladies and he looked at the attractive woman as they passed each other.

Greg did a sort of double-take before saying, "Tony, Tony is that you?"

Toni froze and could not respond even if she/he wanted to.

"Tony, it is you isn't it?" Insisted the confused Greg.

Toni got her voice back and blurted, "Greg, please don't tell anyone," as she blushed as only a woman could.

"No, no, I won't tell anyone, you look fucking gorgeous," said the workmate.

"Don't take the piss, Greg," said the slightly trembling Toni.

"I am not taking the piss, you do look gorgeous... look at that if you don't believe me," said Greg indicating the pronounced bulge in his trousers.

Toni was mesmerised because although whilst dressed many a bulge had been induced in a man's trousers, this was the first time that one had been induced in a workmate.

"Tony, you should know that I dress too but I never look as good as you," confessed Greg.

"Really, you dress? But you are married!" Said a shocked Toni.

"Yes, but so are you married, sort of," said Greg but by now another couple was approaching so, without further words, Toni and Greg continued their journeys in opposite directions.

Greg, however, was so turned on that he went into a nearby clump of trees and relieved his erection with a series of fast jerks.

The next day at work, Anthony and Greg were both a bit subdued and unsure what to say about the previous evening although they both had the feeling that something had to be said. At lunchtime, they got together although there was still a feeling of confusion and embarrassment.

"Well, last night was a night of surprises wasn't it?" Said Greg at last.

"Yes, you will not tell anyone, will you?" Insisted Anthony.

"No of course not mate. I have got my secrets too haven't I?"

"Yes, I had no idea," replied Anthony.

"Obviously, you really did look gorgeous, though," confirmed Greg.

"I still think you are taking the piss," said Anthony.

"Hardly, because after we parted I went into the woods and had a wank," confided Greg.

Anthony was not sure whether to believe him but any further discussion was curtailed by the arrival of another workmate.

At the end of the working day, Greg approached Anthony and said, "I have been thinking. Perhaps we could get together dressed? If you want to, of course."

Although Toni had frequently been in the company of other crossdressers and transvestites she had never been with one on a one to one basis.

"Well, I am not sure. You mean we just get dressed, or do you have anything else in mind?" said Anthony.

"I have never had sex whilst dressed but seeing you last night really turned me on. I don't know what I mean, really."

"I have been fucked by men several times but none of them was dressed and none of them was someone that I knew," said Anthony.

"We do not have to have sex, just get dressed and maybe see what happens," said Greg.

"Okay, but where and when?" Asked Anthony.

"My wife is away this weekend so I was wondering if I could come to your house?" Asked Greg.

"Um, yes sure, but I am still not convinced that it is a good idea."

Good idea or not Greg, dressed as a male but complete with a large suitcase, arrived at Anthony's house. Although Anthony was often Toni when at home, he decided to be in male attire for his guest's arrival. The two men had a swift drink before going to separate bedrooms to get dressed. 

"Take as long as you need, just give me a knock when you are done," said Anthony.

Anthony had far more experience of becoming Toni than Greg did of becoming Gina, which was the name that he liked to think of himself as when dressed. Greg had told Anthony that Gina was his girly name.

Toni was admiring herself in the full-length mirror and looking at how the tight skirt hugged her buttocks and how the blue eye shadow looked just perfect, as did the blonde wig.

Greg changed his mind several times before being happy that Gina had arrived and was pleased with just how feminine and sexy she looked. Feeling a mixture of apprehension and sexual arousal, Gina tapped on the closed bedroom door.

"Come in," said a soft voice from within.

Gina entered and each of the two occupants of the room gazed at the other.

"Fuck, you look amazing Toni," said Gina.

"You don't look so bad yourself, honey," replied Toni, surprised at just how sexy Gina looked.

For a moment, they were both motionless as they were unsure exactly what to do next. But then Toni, as the hostess, took a couple of steps towards her guest and gave her a light kiss on the lips. The two giggled in a girly way and then started stroking the other's arms and chests.

They could both feel their penises hardening rapidly in their panties but at this stage, neither was too sure about how far to go sexually.

"Give us a twirl, love," said Gina and as Toni twirled Gina touched her bottom which brought a bit more girly giggling.

The two stood close together looking into heavily made-up eyes and then seemingly by mutual agreement, their faces came together and a long, passionate tongue swapping kiss ensued. Both girls now had fully erect cocks which were rubbing against each other through panties and skirts.

"How far do you want to go?" Asked Toni breathlessly after the snogging finished.

"All the way, if you want to?" Replied Gina.

"Yep, I have got vaseline and condoms ready," said Toni.

"You slut," laughed Gina.

"I need to get into your panties," said Toni as she undid and pulled down Gina's skirt.

Now Toni had seen a few erect penises over the last twelve months or so, but the one inside the black lace panties that she was gazing at was as big as any of them. Toni kissed Gina's cock through the thin material and Gina sighed in delight. Toni stood and soon her skirt was down and another pair of panties stretched by a large erect cock was on display.

More kissing followed and hands were inside panties and erect cocks and bare buttocks were stroked. Toni was then on her knees and removing Gina's cock from her panties and locking her lips on it. Toni had sucked many a cock and was soon sending Gina crazy with the work that she was doing with lips and tongue.

"Fuck, Toni, this is so fucking good," said Gina who was now squirming as Toni played with her balls whilst sucking and licking her cock.

After a while of this Gina announced, "Oh god, I am going to cum."

This caused Toni to momentarily remove her lips from Gina's prick to almost whisper, "Do it."

With Toni's lips now back on the throbbing penis, Gina shot spurt after spurt of spunk into her throat. Toni took and swallowed every drop before standing and giving Gina a long deep kiss. Gina had never given head before but she was promptly on her knees with Toni's erect cock in her mouth and was licking, sucking and stroking it to the best of her ability and was taking Toni towards ejaculation.

"Let's sixty-nine," suggested Toni and soon she was on top with her cock back in Gina's mouth and was again bringing Gina's previously softened cock back to full erection with her mouth.

Toni felt her spunk rising and thought that she should warn Gina, "Baby, I am going to shoot soon," but that did not deter Gina who kept sucking and promptly took a mouth full of Toni's semen. She did not manage to swallow it all but took most of it and felt pleased with herself.

Gina's cock had been played so well by Toni's mouth that she was again not too far from cumming.

"Do you want to fuck me now, Gina?" asked Toni who, on getting confirmation, fetched the lubricant and contraceptive and handed them to her guest.

Toni was on the bed, arse in the air, as Gina teased her hole before spreading vaseline in and around it and then loosening it with a couple of fingers. Toni had by now taken a few cocks up the arse and Gina's condom encased one was now at the entrance.

Gina, who as a male had sometimes fucked his wife in the arse, slowly eased in and soon built up a rhythm. Toni sometimes ejaculated whilst being fucked and was getting close to it now as Gina's cock slid in and out. On this occasion, Toni did not cum with a cock in her ass but with a loud groan, Gina filled her condom with spunk.

With Gina being an anal virgin it took a bit of work before Toni's condom covered penis entered her but Toni then gave her a good fucking from the front with her legs on Toni's shoulders. Gina actually came again just before Toni emptied spurt after spurt of semen into the condom.

"Well that was fun," laughed Gina after they had regained their breath.

"It certainly was, we must do it again sometime," said Toni.

There was little doubt that they would indeed do it again sometime.

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When people think of a middle aged guy having an affair it is usually with their female secretary or yoga teacher… but I wonder how often it is with a younger guy at the pool. Which is what happened with my Married Guy (visit my blog to read about those experiences). Here is an experience that one of my new members sent to me. I’m not 100% sure if it is a true story or fiction but either way it is...

2 years ago
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Toni In The Park

This just happened on Wednesday and I felt I just had to tell you right away… There is a state park near us that has a pond and small beach. There are picnic tables and trees for shade close by on the grass. The park officially closes after labor day and there are no longer gate attendants or lifeguards but you can still go in. The weather here, a week after labor day, has still been unusually warm and sunny. I told Toni I was taking her to the park for our next adventure. I told her to...

2 years ago
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Tamara Greg

Tamara & Greg A story for Lush by EroticCop Hi. My name is Greg and I’m a high school senior. I live in a suburb of Minneapolis and play hockey, a lot. In fact, I’ve been playing varsity since I was a freshman. As a senior, I’m captain and have twelve different division I and II schools checking me out. I’m six foot four, and I weigh two hundred and twenty­-five pounds. I’ve been a gym rat since I got to high school, but that changed when a new girl came to school this year. Ok, since I’ve...

2 years ago
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PASsport Happening Encounters

8PHE0000 A note to the reader: (387 words) Hi. This is my first attempt at a story for this site. It's actually fan-fiction - if you can be a fan of something that was posted for just a few days but then removed. Inspiration for this story comes from a game on tfgamessite.com called Glitch in HAVEN, by SlayerKh. I tried contacting the author of that game before posting this. In that game, which was really more of bare-bones outline of an idea for a game, (pre-Alpha release), the...

1 year ago
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College Days by Greg

By Greg The college I attended was a well-respected engineering school on the east coast. The problem was that this attracted a majority of male students. The available females in school were mostly eggheads, or had some kind of issue to prove like; “I’m just as good as any man,” and they had the appropriate attitude to go with it. This really put a crimp in the sex life of a freshman. I was originally from a mid-western city. I was used to partying...

2 years ago
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CDay Of Greg

I still remember that day, clear as the waters of Mediterranean. 23rd of August, Malaga, Spain.---I am sitting on cold wet sand; several steps away from the sea, watching the moonlight glimmer on the calm water. It is a quiet night, only sounds of waves gently sweeping the coast and seagulls chanting far on the rocks. I am listening carefully, waiting for 'her'.The peaceful music of the waves is soon broken by a bitter creak of the dry wood. The sound comes from the old pavilion several...

Cuckold
4 years ago
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College Days by Greg

Introduction: To comply with this sites new censorship rules, all references to age have been edited. Readers should consider all characters to be at least 18 years old. Sorry for any confusion in the story line. College Days By Greg The college I attended was a well-respected engineering school on the east coast. The problem was that this attracted a majority of male students. The available females in school were mostly eggheads, or had some kind of issue to prove like, Im just as good as any...

3 years ago
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Random Encounters Ramyas Cousin Sister

This is a continuation of my encounters with Ramya. You can read the first part of it at Random Encounters 1- The Cute Bihari. Me and Ramya has been hanging out together for a while and we never really hooked up despite the lingering tension between us. I guess my efforts were half hearted and she was still hung up over her ex -bf. Anyway, it finally happened a few days before she was about to move out of the city and it was worth the wait. The long overdoses of the encounter spiced it up and...

2 years ago
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Caribbean Encounters More

I couldn't believe my luck. I had finally convinced my wife to leave the responsibilities behind and take a well deserved vacation. Just the two of us this time. We were heading for an adults only resort in Jamaica and I was excited. The resort was noted for luxury, dining and its au natural areas. Beth was smiling as we descended into Montego Bay. She was aware of the resort , but it was not her first choice. She loves the beach and the pampering, but she is not as thrilled with the exhibition...

1 year ago
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Random Encounters 8211 Ramya The Incredible

This is the third and last part of my random indian sex encounters related to ramya. You can read the last part in “random encounters – ramya’s cousin sister”. I met riya, ramya’s cute cousin sister in bangalore and she was well acquainted with me as I used to visit often. She apparently used to jerk off to hearing us fuck and it was quite a turn on to hear the pretty little thing talk dirty. As described in the previous story, I was at their place for a house party which ended with me and riya...

3 years ago
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Hot Encounters Parts 9 and 10

This is the next submission in an ongoing story. For author's notes and disclaimers and to be fully up to speed, please read the previous first. Readers be aware that this material contains lifestyles and sexual acts that may be a turn on for some may also be offensive others. I am my own editor so please forgive me for any typos. ******************************************************************* After Jen left, July was a long month for me especially coming home to Jen's bed, TV, and...

1 year ago
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Abroad Encounters With Anamika 8211 Episode 1

Dear Indian sex stories readers and authors !! I am back again Vijay, who at the moment residing in Nepal. I have already told about myself in my previous narration “Pune History with Sanjana”…You can read the below and please give the feed back to or Any girls or ladies who would like to have a great pleasure can contact me. Secrecy and respect is well maintained You can read for my intro and how am I. I have already informed in my previous narration that there are many more to come all my...

4 years ago
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Close Encounters of the Second time TheermS

Well this sucked!The whole situation stunk worse than 6 day old fish.I collapsed into my friend's couch. I had just come off the phone to Ronni for some reassurance.I took a few deep breaths and tried to settle my nerves.About 10 minutes before I had had to end a disasterous encounter with a ghastly little wastrel called Dan. It had gone badly....it could have gone worse, but it seemed bad enough at the time.What happened was...and its all laid out in probably too much detail in the first...

3 years ago
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Goa Encounters The Malvika Diaries 8211 Part 1

Hi Guys! This is Malvika Kapoor from Mumbai. I know you all might be waiting to read my encounters but I had to do them so that I can write it for you all. I am going to share my Goa encounters with you all which I have written with the help of my friend Chetan. I am sure you will enjoy it in his words. Hello all you amazing readers out there on ISS. This is Chetan back again with the next part of my sexual endeavors with Malvika Kapoor. For all those who don’t know me or Malvika, please refer...

1 year ago
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Tonia

One night I went to a different club to check things out. By now, Iknew what I was looking for and where to find it. I was cruising thearea with several bars for people with my kind of preferences youknow women with more to offer a man.I parked out in the lot and began to walk in as I did I noticed thisbeautiful brunette with long legs. I was very interested infollowing her into the bar. I rushed to open the door for her as shejust politely blushed and smiled at me. I tipped my head to her...

1 year ago
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Hot Encounters Part 1 and 25

The following is the first submission of a continuing story which chronicles an 18 year old around the 1980 time frame who, by his own choice, is introduced to sexual adventures beyond his wildest expectations. The events continue well into his early 20s. The sexual encounters are true; however, the character names have been changed and most locations and dates noted are intentionally vague as to not directly reflect any historical or geographical reality. This is about sexual encounters not...

3 years ago
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Random Encounters 1 The Cute Bihari

It’s somewhat strange to write regarding my sexual experiences. But having been an avid sex story reader of Indian Sex Stories dot net for a long time, I feel this is the right time to talk about my encounters. I am 36, 5”5 and educated at one of India’s best institutes (Indian women love fancy educational qualifications, trust me). Looks do land you girls, but then in India, so does being well educated and being nice. I lost my virginity fairly late when I was 25 and I always felt that the...

2 years ago
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Abroad Encounters With Anamika 8211 Sweet Sweat Session

Hi everyone, I am back, Vijay with another hot encounter with Anamika. For the readers who does not know, i am 34 years old, Chennai boy now working in Nepal. Athletic built, with a tool of 7″ which is good enough to satisfy the partner. Very genuine and have never touched any one without their full consent and respects the partners feelings. Always maintains confidentiality, secrecy if any girl, divorcee, widow and unsatisfiable soul if required pleasure, sheer pleasure. Will ensure that the...

2 years ago
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FIRST SEXUAL ENCOUNTERS

Do remember your 'first time'?The first time that someone paid sexual attention to you. The first timethat someone looked at you with a look in his eyes that thrilled andterrified you at the same time. The first time that someone else's lookmade your penis harden and lengthen. The first time that you knew someonewanted to touch you... down there.Of course you do.Go back to that person, that place, that moment. Your cock is stiffeningalready.I admit I've always been fascinated by first time...

3 years ago
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PASsport Happening Encounters Day 6

8PHE0006 Word Count 5007 ******** Day 6, Sunday Kinny woke up. Someone was in his room. He had a headache. His teeth hurt. Even his hair hurt. "Up, up!" Joi shook him. "Time to hit the gym." Kinny groaned. She poked him in the ribs. "You've been drinking Cactus Jack and eating corn gorillas for three days. Time to work off the pudge." "Pudge?" "You're getting man boobs." "I am?" Kinny sat up. He checked under his shirt. "Denied." Although his nipples were sore...

3 years ago
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Tonis Baby Girl

Toni's Baby Girl By Pamela ([email protected]) It's interesting when a husband or wife finds something new about their spouse after being married a few years. Take my marriage for example. I've long suspected that my wife, Toni, has sensitive nipples that she enjoys having sucked on or caressed. What I hadn't realized was exactly how powerful this pleasure is for her. One day after we had made love together in our typical way she said in frustration, "Greg, you're welcome to...

3 years ago
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True Confessions Intimate Encounters Part 1

Something miraculous happened to Frank that first morning he tasted Linda’s sweet nectar. Whatever was holding him back sexually magically disappeared. Linda preferred oral and under her tutelage Frank became an expert lover, his fingers and tongue never failed to satisfy us or any girl he made love to. Neither did his cock. Suddenly, at 49 he was walking around with a perpetual boner, just like some randy 16 year old. Many of our most satisfying sexual encounters were with complete strangers...

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